EP 0 831 799 B1
`
`
`
`
`
`°°.?“P°uz2s1_:.35
`
`'
`
`'¢°;|IP°und 137-
`
`
`
`
`
`_Caurpound 13 9
`
` H;
`
`‘
`
`com-nouz~.'d 141
`
`
`
`carnuouna 1&5 .
`
`gbunound 143
`
`-CF
`Corigaaund 156
`
`H4-
`
`'.
`
`O
`
`Ccsgzound zu
`
`céwadnd 145 '
`
`80
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0501
`
`15
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`20
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`25
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`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0501
`
`

`
`EP 0 831 799 B1
`
`c N& . ‘c “%
`«of
`co”
`
`s .0.
`
`cémpouad 14:
`
`Compound :45
`
`20
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`25
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`30
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`35
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`45
`
`55
`
`’:°f©TV@:
`U
`
`Ccaxpdund 15¢ '
`
`, and phannaceutically acceptable salts and complexes thereof for the preparation of a pharmaceutical com-
`position for the treatment of a neurological disease or disorder.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 54-66,
`68-71, 75, 76. 78, 79, 81-90, 92-98, 100, 101, 103, 105. 106, 108, 109. 111, 114-122, 124-136, 138,139,141-144,
`148-150. and pharmaceutically acceptable salts and complexes thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 54-66,
`69, 70. 75. 76, 81-83, 85-97, 100- 103, 105, 106, 108, 109, 111, 115, 118-122, 125-133,135-139, 142, 144-150,
`and pharmaceutically acceptable salts and complexes thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 54-66,
`69, 70. 75, 76, 81-83, 85-90, 92-97,100,101,103,105,106. 108,109,111, 115, 118-122,125-133, 135,136,138.
`139, 142. 144, 148-150, and phannaceutically acceptable salts and complexes thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 54-66,
`69, 82, 83. 89-97, 103, 111. 118-120, 122. 126, 135-138, 142. 144, 145. 147-150, and pharmaceutically acceptable
`salts and complexes thereof.
`
`The use according to claim 1. wherein the compound is selected from the group consisting of compounds 54-66,
`69. 82, 83, 89-90, 92-97, 103, 111, 118-120, 122, 126. 135, 136. 138, 142, 144, 148-150, and pharmaceutically
`acceptable salts and complexes thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 60, 66.
`69. 103, 111, 118-120, 122, 136, 138, 142, 144, 148-150, and phannaceutically acceptable salts and complexes
`thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 118-122,
`137, 145, 148-150, and pharmaceutically acceptable salts and complexes thereof.
`
`The use according to claim 1, wherein the compound is selected from the group consisting of compounds 118-122,
`148-150, and pharmaceutically acceptable salts and complexes thereof.
`
`81.
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0502
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0502
`
`

`
`EP 0 831 799 B1
`
`10. The use according to claim 1, wherein the compound is selected from the group consisting of compounds 63 and
`64 and pharmaceutically acceptable salts and complexes thereof.
`
`11. The use according to claim 1, wherein the compound is selected from compound 119, and pharmaceutically ac-
`ceptable salts and complexes thereof.
`'
`
`12. The use according to claim 1, wherein the compound is selected from compound 144, and pharmaceutically ac-
`ceptable salts and complexes thereof.
`
`13. The use of compound 60, and pharmaceutically acceptable salts and complexes thereof for the preparation of a
`pharmaceutical composition for the treatment of a neurological disease or disorder.
`
`14. Use of a compound having the formula:
`
`
`
`wherein:
`
`X is independently selected from the group consisting of -Br. —Cl. -F, -I,-CF3, alkyl, -OH, -OCF3. -O-alkyl, and
`-O-acyl;
`R1 is independently selected from the group consisting of -H, C1-C4 alkyl, and -O-acyl;
`R2 is independently selected from the group consisting of -H. alkyl, and hydroxyalkyl, or both Rzs together are
`mine;
`'
`
`R4 is phenoxy which is optionally substituted with —F, -Cl, -Br, -I. -CF3, alkyl, -OH .- OCF3-O-alkyl, or -O-acyl; and
`m is independently an integer from 0 to 5; and phannaceutically acceptable salts and complexes thereof pro-
`vided that said compound is not:
`3-(p-isopropoxyphenoxy)-3-phenylpropylamine
`3-(2'-methyl-4',5’-dichlorophenoxy)-3-phenylpropylamine
`3-(p-t-butylphenoxy)-3-phenylpropylamine
`3-(2'.4'-dichlorophenoxy)-3-phenyl-2—methyI propylamine
`3-(o-ethylphenoxy)—3-phenylpropylamine
`3-(o-methoxyphenoxy)—3-phenylpropylamine
`3-phenoxy-3-phenylpropylamine
`
`for the preparation of a pharmaceutical composition for the treatment of a neurological disease or disorder.
`
`'15. Use of a compound having the formula
`
`wherein:
`
`
`
`82
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`10
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`15
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`25
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`30
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`35
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`40
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`45
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`50
`
`55
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0503
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0503
`
`

`
`EP 0 831 799 B1
`
`X is independently selected from the group consisting of-F. -Cl. -Br, -l, -CF3 alkyl, -OH, ~OCF3, -O-alkyl. and
`-O-acyl;
`R1 is independently selected from the group consisting of -H. C1-C4 alkyl, and -O-acyl;
`R2 is independently selected from the group consisting of -H, C1-C4 alkyl, and hydroxyalkyl. or both R25 to-
`gether are imino;
`'
`~
`R3 is selected from the group consisting of methyl and ethyl;
`R4 is phenoxy which is optionally substituted with -F, -Cl, -Br, -I, -CF3. alkyl, -OH. -OCF3, -O-alkyl, or -O-acyl;
`and m is independently an integer from 0 to S; and pharmaceutically acceptable salts and complexes thereof
`provided that said compound is not
`N-methyl 3-(o-chloro-p—tolyloxy)-3-phenyl-1-methylpropylamine
`N-methyl 3-(p-tolyloxy)—3-phenylpropylamine
`N-methyl 3—(o-chloro-p—iscpropylphenoxy)-3-phenyl-2—methylpropylamine
`N-methyl 3-(p-iodophenoxy)-3-phenyl-propylamine
`N-methyl 3-(3-n propylphenoxy)-3-phenyl-propylamine
`N-methyl 3-(p-trilluoromethylphenoxy)—3-phenylpropylamine
`N-methyl 3-(m-chlorophenoxy)-3-phenylpropylamine
`N-methyl 3—(p-lluorophenoxy)-3-phenylpropylamine
`N-methyl 3-(o-methoxyphenoxy)-3-phenylpropylamine
`N-methyl 3-(o-methoxyphenoxy)-3-phenylpropylamine
`N-methyl 3-(o-lluorophenoxy)-3-phenylpropylamine
`N-methyl 3—(m-fluorophenoxy)—3—phenylpropylamine
`N-methyl 3-(p-chlorophenoxy)-3-phenylpropylamine
`N-methyl 3-(m—fluorophenoxy)-3-phenylpropylamine
`N-methyl 3—phenoxy-3-phenyl-2-methylpropylamine
`N-methyl 3-phenoxy-3-phenyl-1-methylpropylamine
`N-methyl 3-phenoxy-3-phenylpropylamine
`N-methyl 3-(o-trifluoromethylphenoxy)-3-phenylpropylamine
`N-methyl 3-(m-rnethoxyphenoxy)-3-phenylpropylamine
`N-methyl 3-(o,p-difluorophenoxy)-3-phenylpropylamine
`N—ethyl-3-(o-iodophenoxy)-3-phenylpropylamine
`N-methyl-3-(o-chlorophenoxy)-3-phenylpropylamine
`N-methyl-3—(o-bromophenoxy)-3-phenylpropylamine
`
`for the preparation of a pharmaceutical composition for the treatment of a neurological disease or disorder.
`
`16. Use of a compound having the formula:
`
`
`
`wherein:
`
`(X)m is selected from the group consisting of meta-fluoro, meta-chloro, Ortho-O-C,-C4 alkyl, ortho-methyl,
`ortho-fluoro. ortho-chlorc, meta-O-C1-C4 alkyl, meta-methyl, ortho-OH, and meta-OH;
`R1 is H;
`R2 is H;
`R3 is selected from the group consisting of methyl and ethyl;
`R4 is phenoxy which is optionally substituted with -F, -Cl. -Br, -I, -CF3, alkyl, -OH, -OCF3. -O—alkyl. or -O-acyl;
`and pharmaceutically acceptable salts and complexes thereof. for the preparation of a pharmaceutical com-
`position for the treatment of a neurological disease or disorder.
`
`10
`
`15
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`20
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`25
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`30
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`35
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`40
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`50
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`
`83
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0504
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0504
`
`

`
`EP 0 831 799 B1
`
`17. The use of any one of claims 1 to 16. wherein the neurological disease or disorder comprises stroke, head trauma.
`spinal cord injury, spinal cord ischemia. ischemia- or hypoxia-induced nerve cell damage. epilepsy, pain, anxiety.
`neuropsychiatric or cognitive deficits due to ischemia or hypoxia such as those that frequently occur as a conse-
`quence of cardiac surgery under cardiopulmonary bypass, Alzheimer's disease. Huntington's disease, Parkinson's
`disease. or amyotyrophic lateral sclerosis.
`'
`‘
`
`18
`
`19
`
`20
`
`21
`
`22
`
`. The use of claim 17. wherein said stroke is global ischemic.
`
`. The use of claim 17, wherein said stroke is focal ischemic.
`
`. The use of claim 17, wherein said stroke is hemorrhagic.
`
`. The use of claim 17, wherein the neurological disease or disorder comprises Parkinson's disease.
`
`. A compound selected from the group consisting of
`
`Q
`
`Compound 54
`
`l ‘I
`. F g /
`
`‘CH’
`NH,
`
`F.
`
`Compound 55
`
`CH; F
`
`F .
`
`NH;
`
`ca,
`
`Ni-1,
`"F '
`Fm’
`
`Cori11l5ound' 58 7
`
`C°flPOu.nd. 57 ‘ '
`
`
`
`10
`
`15
`
`20
`
`25
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`30
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`35
`
`40
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`45
`
`50
`
`55
`
`84
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0505
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0505
`
`

`
`EP 0 831 799 B1
`
`OCH;
`
`NH;
`
`F
`
`Compound 61
`
`
`
`Campcund E4
`
`
`
`
`
`C;::.'.'.::aun.d 76
`
`C°I!P0I:!1-'1_d- 7a’
`
`10
`
`15
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`20
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`25
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`30
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`35
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`40
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`45
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`55
`
`85
`
`Patent Owner, UCB Pharma GmbH —’Exhibit 2007 - 0506
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0506
`
`

`
`EP 0 831 799 B1
`
`NH1
`
`\ /
`
`Cpqxpound 79
`
`2
`
`counpéund as
`
`0
`
`NH
`
`OH
`0
`
`Cémpound 84'.
`
`on
`
`:NH
`
`F ‘Diff
`OF
`Campounfi. 8 2
`
`NH‘.
`
`Compound 9 0
`
`NH;°
`NH
`
`O F
`
`nmnound '89
`
`F C
`
`B 0;./"Hi-[2
`
`W
`
`
`
`Compound 92
`
`
`
`compouna S3
`
`86
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0507
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`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0507
`
`

`
`EP 0 831 799 B1
`
`' Compound 94
`
`
`
`Compound 38
`
`
`
`Coruaaund 9 5
`
`
`
`
`
`Ccunbound 101
`
`'comuou.nd 102
`
`
`
`Ccunpqund 103
`
`
`
`Corisyound 105
`
`10
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`55
`
`87
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0508
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0508
`
`

`
`EP 0 831 799 B1
`
`
`
`C°l_1Do‘u.nd am 8
`
`
`
`Cpmpaund 107
`(mixture o£ 2
`o
`cacnaounds)
`
`
`
`Cornoound 3.09
`
`
`
`
`
`Compound 11_5
`
`Comnofind 116‘
`
`10
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`15
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`20
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`25
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`30
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`35
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`40
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`45
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`50
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`'55
`
`88
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0509
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0509
`
`

`
`EP 0 831 799 B1
`
`Cordpounci 113
`
`.
`.©’
`Compoimdl 119
`
`9w
`«G,
`
`Compound 12 O
`
`O - NH:
`
`‘Compound 124
`
`Coiupoulnld 1_i5
`
`Compound 127
`
`10
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`15
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`20
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`25
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`30
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`35
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`40
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`50
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`55
`
`89
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0510
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0510
`
`

`
`EP 0 831 799 B1
`
`“'5
`
`Compound 129
`
`%,n,,
`%%
`
`
`
`Eramaouha 130
`
`‘ Cémsmund 13:. -
`
`G
`
`Camppund 1.34
`
`NP»:
`
`uqco Q “'9-
`
`C6mpou:_u;I_ 135
`
`Compound 137.
`
`.
`
`
`camnouné 135 .
`
`
`
`conmaund 138 ~
`
`
`
`Compound 135
`
`10
`
`20
`
`25
`
`30
`
`35
`
`40
`
`.45
`
`50
`
`55
`
`90
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0511
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0511
`
`

`
`10
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`15
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`20
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`25
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`30
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`40
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`55
`
`EP 0 831 799 B1
`
`
`
`'
`"
`H;
`Comnound 142
`
`
`
`
`
`Cc:=ou:1d 143
`
`
`
`«GYW,
`“Q”.
`c°W°‘-‘Dd 149
`
`Con-pound in
`
`ccnqmund 150
`
`and pharmaceutically acceptable salts thereof.
`
`23. The compound according to claim 22, selected from the group consisting of compounds 54-66. 69. 76. 82, 83.
`
`91
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0512
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0512
`
`

`
`EP 0 831 799 B1
`
`88~90,92-96.101.102.103.105,108,109,111,115.118-122,125-127,129—131,135-139,142,144,145,148-150,
`or pharmaceutically acceptable salts thereof.
`
`24.
`
`25.
`
`10
`
`26.
`
`The compound according to claim 22, selected from the group consisting of compounds 54-66. 69. 82, 83, 89, 90,
`93-96. 103, 111,118-120, 122, 126. 135-138, 142.144.145.148-150, or pharmaceutically acceptable salts thereof.
`
`The compound according to claim 22, selected from the group consisting of compounds 60, 66, 69, 103, 111,
`118-120, 122, 136-138, 142, 144, 145, 148-150, or phannaceutically acceptable salts thereof.
`
`The compound according to claim 22. selected from the group consisting of compounds 118-122, 137, 145,
`148-150, or phannaceutically acceptable salts thereof.
`
`15
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`20
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`25
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`30
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`35
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`40
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`45
`
`50
`
`55
`
`27.
`
`28.
`
`29.
`
`30.
`
`31.
`
`32.
`
`The compound according to claim 22, selected from the group consisting of compounds 118-122,148-150, or
`pharmaceutically acceptable salts thereof.
`
`The compound according to claim 22, selected from the group consisting of compounds 63 and 64, or pharma-
`ceutically acceptable salts thereof.
`
`The compound according to claim 22, which is compound 119, or phannaceutically acceptable salts thereof.
`
`The compound according to claim 22, which is compound 144, or pharmaceutically acceptable salts thereof.
`
`Compound 60, or phannaceutically acceptable salts thereof.
`
`A compound of the formula:
`
`
`
`wherein:
`
`X is independently selected from the group consisting of -Br. -Cl, -F, -I,-CF3, alkyl, -OH, -OCF3, -O-alkyl, and
`-O-acyl;
`R1 is independently selected from the group consisting of -H, C1-C4 alkyl, and -O-acyl;
`R2 is independently selected from the group consisting of -H, alkyl, and hydroxyalkyl, or both Rzs together are
`imino;
`
`R4 is phenoxy which is optionally substituted with -F, -Cl, -Br, -I, -CF3. alkyl, -OH,- OCF3 -O-alkyl, or -O-acyl; and
`m is independently an integer from 1 to 5; and pharmaceutically acceptable salts and complexes thereof:
`
`33.
`
`A compound of the formula:
`
`
`
`92
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0513
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0513
`
`

`
`wherein:
`
`EP 0 831 799 B1
`
`X is independently selected from the group consisting of —F, -Cl, -Br, -I. -CF3 alkyl, -OH, -OCF3, -O-alkyl, and
`-O-acyl;
`R1 is independently selected from the group consisting of-H, C,~C4 alkyl, and -O-acyl;
`R2 is independently selected from the group consisting of-H. C1-C4 alkyl, and hydroxyalkyl, or both Rzs together
`are imino;
`
`R3 is selected from the group consisting of methyl and ethyl;
`R4 is phenoxy which is optionally substituted with -F. -Cl, -Br. -I, -CF3. alkyl, -OH. -OCF3, -O-alkyl, or -O-acyl;
`
`and m is independently an integer from 1 to 5; and pharmaceutically acceptable salts and complexes thereof
`provided that said compound is not N-methyl 3-(m-trifluoromethylphenoxy)-3-(4-fluorophenyl)propylamine.
`
`34. A compound of the formula:
`
`
`
`(X)m is selected from the group consisting of meta-fluoro, meta-chloro. ortho-0-C,-C4 alkyl, ortho-methyl,
`ortho-fluoro. ortho-chloro, meta-0- C1-C4 alkyl, meta-methyl. ortho-OH. and meta-OH;
`R1 is H;
`R2 is
`R3 is selected from the group consisting of methyl and ethyl;
`R4 is phenoxy which is optionally substituted with —F, -Cl, —Br. —I, -CF3, alkyl, —OH. -OCF3, -O-alkyl, or -O-acyl;
`and pharmaceutically acceptable salts and complexes thereof.
`
`35. A pharmaceutical composition comprising a compound which is selected from the group consisting of
`
`~
`
`‘H
`
`F Q only
`
`15
`
`20
`
`25
`
`30
`
`35
`
`40
`
`45
`
`50
`
`55
`
`Compound 35
`
`-
`
`NH:
`
`,
`
`H:
`
`F
`
`, 0
`
`F
`
`NH;
`@ CH3
`
`Compound 57 '
`
`93
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0514
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0514
`
`

`
`' EP 0 331 799 B1
`
`10
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`15
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`20
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`25
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`30
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`35
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`40
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`45
`
`50
`
`55
`
`Compound 84
`
`Compound 65
`
`.}ic,,?
`
`Compound 67 ’
`
`NW
`
`
`
`Cgmpound 70
`
`Compcund 71
`
`Compound 12
`
`94
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0515
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0515
`
`

`
`EP 0 831 799 B1
`
`C°mp0u§za 75 ’
`
` Compound 77
`
`
`
`Cmpound 21
`
`_
`NH
`
`.
`Q
`
`0 H
`O
`
`Coupauna. 84
`
`I
`s
`
`.
`- “"7
`
`
`
`
`
`Comaéund 75
`
`'
`
`NH;
`
`I \
`/
`
`F
`
`Compound 79
`
`10
`
`15
`
`20
`
`25
`
`30
`
`35
`
`40
`
`45
`
`50
`
`55
`
`95
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0516
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0516
`
`

`
`EP 0 831 799 B1
`
`
`
`Compound 85
`
`(mixture of 2
`
`<:oc.1oounc_T.s)
`
`'
`
`Compound 8.6‘
`(lnixture of 2
`
`com-sounds)
`
`‘ NH;
`an
`
`COmp_aur{d .37
`
`0 02;”,
`.
`
`F 8
`
`.'
`
`NH.
`
`S /
`
`'
`
`compound 88
`
`Comoouna .85
`
`compdund so
`
`G
`
`L@
`
`Q
`
`Cacnpound. 92-
`
`
`
`Canrsxouna 55;
`
`15
`
`20
`
`25
`
`30
`
`35
`
`40
`
`45
`
`50
`
`55
`
`96
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0517
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0517
`
`

`
`EP 0 831 799 B1
`
`‘ I->6-I,
`
`Ccmgaund 97
`
`Conpound $8
`
`O
`
`Camoou.nd' 100
`
`
`
`Compound 10:
`
`. me,
`
`HO
`
`an
`
`0
`
`Cumnound 101
`
`Conrnauna 1c;
`
`M:
`"
`
`Compound 1.05
`
`10
`
`15
`
`20
`
`25
`
`30
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`35
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`40
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`45
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`55
`
`97
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0518
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0518
`
`

`
`EP 0 831 799 B1
`
`
`
`Compound 106
`
`Ccmsound 1'0 3
`
`C,°m9oun:1 107
`fnnbccuxa of 2
`cozwaouncis)
`
`
`
`Comaaund 109
`
`
`
`Cfimnound 111
`
`CF?
`
`3!
`
`C°m9ou.nd 11¢
`
`15
`
`20
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`25
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`30
`
`35
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`40
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`45
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`50
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`55
`
`98
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0519
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0519
`
`

`
`EP 0 831 799 B1
`
`
`
`Compound 11$
`
`©E:T”"”’
`
`‘3°m1=ou::d 117
`
`Comaound 12 0
`
`
`
`Comuoxmd 3:21
`
`NH; .
`
`0
`
`Comno u_vaa~. 12 4
`
` "C°NP=:u.:v:1 3.115 .
`
`10
`
`15
`
`20
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`25
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`30
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`35
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`40
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`55
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`99
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0520
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0520
`
`

`
`EP 0 831 799 B1
`
`©
`
`re
`
`Campound 127
`
`
`
`_Ccmoot.'.nd 128
`
`M0
`
`Csocupou:-L5 129
`
`NH:
`0
`
`
`
`Compoimd 13 D
`
`COW-pcund 13:.
`
`“E:
`
`Compound .'L3_2
`
`%m 0
`
`éompound 133
`
`O
`
`NH:
`
`Carnpound 134
`
`O \/N“: W
`
`H:°HzC0
`
`""‘
`
`Q
`
`C.
`
`.K©,O
`
`Compound 135
`
`Compound 13 6
`
`Cnmpourid 1_37-.
`
`10
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`35
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`55
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`100
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0521
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0521
`
`

`
`10
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`15
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`20
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`25
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`30
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`35
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`40
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`45
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`
`C -
`a O
`
`Ccmpound 13 8
`
`EP 0 831 799 B1
`
`’“0 .
`
`Ccnipaund 135
`
`
`
`H;
`
`'
`
`compound in
`
`“Wmen a '
`
`Compouzid 1&5 .
`
`
`
`Cougaund 143 .
`
`" my
`
`0
`Co.-.:;:c\m:1' 14:
`
`;©T;a..,-
`‘U
`Couyofind. 14S_
`
`©,%
`
`Compound 1&6’,
`
`Ccupound 148
`
`101
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0522
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0522
`
`

`
`EP 0 831 799 B1
`
`36.
`
`37.
`
`38.
`
`39.
`
`40.
`
`41.
`
`10
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`20
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`25
`
`30
`
`42.
`
`43.
`
`35
`
`and pharmaceutically acceptable salts thereof in a pharmaceutically acceptable carrier.
`
`The pharmaceutical composition according to claim 35. comprising a compound selected from the group consisting
`ofcompounds 54-71. 73, 76-79, 81-84, 88-90, 92-98, 101-103,105,107-109,111,115,117-123,125-127.129-136,
`138. 139, 142, 144-146, 148-150. and pharmaceutically acceptable salts thereof, in a pharmaceutically acceptable
`carrier.
`<
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from the group consisting
`ofcompounds 54-66, 69, 70, 75, 76, 81-83. 85-90, 92-97, 100-103, 105,106,108, 109. 111,115. 118-1 22, 125-133,
`135-139, 142. 144-146, 148-150, and pharmaceutically acceptable salts thereof. in a pharmaceutically acceptable
`carrier.
`
`The pharmaceutical composition according to claim 35. comprising a compound selected from the group consisting
`of compounds 54-66, 69. 70, 76, 81-83, 88-90, 92-97, 101-103, 105, 106, 108, 109, 111. 115, 118-122, 125-127,
`129-133, 135. 136, 138, 139, 142. 144-146, 148-150, and pharmaceutically acceptable salts thereof, in a phar-
`maceutically acceptable carrier.
`
`The pharmaceutical composition according to claim 35. comprising a compound selected from the group consisting
`of compounds 54-66, 69. 82, 83, 89, 90, 93-97. 103, 111, 118-120. 122, 126, 135- 138, 142, 144, 145, 148-150,
`and pharmaceutically acceptable salts thereof, in a pharmaceutically acceptable carrier.
`'
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from the group consisting
`of compounds 54-66.69.82.133, 89, 90. 93-97, 103,111, 118-120.122. 126,135. 136,138,142, 144,145, 148-150.
`and pharmaceutically acceptable salts thereof, in a pharmaceutically acceptable carrier.
`«
`
`The phannaceutical composition according to claim 35, comprising a compound selected from the group consisting
`of compounds 60, 66, 69, 103, 111 , 118-120, 122, 136-138, 142. 144, 145. 148-150, and pharmaceutically accept-
`able salts thereof. in a pharmaceutically acceptable carrier.
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from the group consisting
`of compounds 118-122, 137. 145. 148-150. and pharmaceutically acceptable salts thereof. in a pharmaceutically
`acceptable carrier.
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from the group consisting
`of compounds 118-122, 148-150. and pharmaceutically acceptable salts thereof. in a pharmaceutically acceptable
`carrier.
`
`>40
`
`45
`
`50
`
`55
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from the group consisting
`of compounds 63 and 64, and pharmaceutically acceptable salts thereof, in a pharmaceutically acceptable carrier.
`
`The phannaceutical composition according to claim 35. comprising a compound selected from compound 119.
`and phannaceutically acceptable salts thereof, in a pharmaceutically acceptable carrier.
`
`The pharmaceutical composition according to claim 35, comprising a compound selected from compound 144,
`and phannaceutically acceptable salts thereof, in a pharmaceutically acceptable carrier.
`
`A pharmaceutical composition comprising a compound selected from compound 60, and pharmaceutically accept-
`able salts thereof. in a phannaceutically acceptable carrier.
`
`45.
`
`46.
`
`47.
`
`. A pharmaceutical composition comprising a compound of claim 32. in a phamiaceutilly acceptable carrier.
`
`49.
`
`50.
`
`51.
`
`A pharmaceutical composition comprising a compound of claim 33, in a pharmaceutically acceptable carrier.
`
`A pharmaceutical composition comprising a compound of claim 34, in a pharmaceutically acceptable carrier.
`
`The pharmaceutical composition of any one of claims 35-50 adapted for the treatment of a neurological disease
`or disorder.
`
`102
`
`Patent Owner, UCB.Pharma GmbH — Exhibit 2007 - 0523
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0523
`
`

`
`10
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`
`EP 0 831 799 B1
`
`52. The pharmaceutical composition of claim 51. wherein said neurological disease or disorder is selected from the
`group consisting of stroke. head trauma, spinal cord injury, epilepsy, anxiety. Alzheimer's disease. Huntington's
`disease. Parkinson's disease. or amyotrophic lateral sclerosis.
`
`53. The pharmaceutical composition of claim 51, wherein said pharmaceutical composition has neuroprotectant ac-
`tivity.
`
`. The pharmaceutical composition of claim 52, wherein said stroke is global ischemic.
`
`55.
`
`56.
`
`57.
`
`The pharmaceutical composition of claim 52, wherein said stroke is focal ischemic.
`
`The pharmaceutical composition of claim 52. wherein said stroke is hemorrhagic.
`
`The pharmaceutical composition of claim 52, wherein said neurological disease or disorder is Parkinson's disease.
`
`Patentanspriiche
`
`1. Vennlendung einer Verbindung, die'aus
`
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`Verbmdlmg 54
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`Verbindung S5
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`Verbindung 56
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`Verbindung 57
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`Verbindung 59
`
`Qr ~
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`
`.
`
`A Verbindung 60
`
`Verbindung 61
`
`Verbindung 62
`
`103
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0524
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0524
`
`

`
`EP 0 831 799 B1
`
`fin, .
`
`/
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`Verbindung 63
`
`Verbindung 64
`
`Verbindung 65
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`1‘
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`
`erbindung 68
`
`§./>
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`
`Vgrbindung 67
`
`Verbindung 69
`
`Verbindung 70
`
`Verbindung 71
`
`Verbindung 73
`
`ce—;
`_
`
`I '
`
`/ ’
`%_/
`
`Verbindung 72
`
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`104
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0525
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0525
`
`

`
`EP 0 831 799 B1
`
`
`
`C:-3
`
`3?:
`
`Verbindune 75
`
`Verbindung 77
`
`Verbindung 78
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`5-!
`I: (C 33152
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`Verbindung 81
`
`Verbindung 82
`
`
`
`Verbindung 85
`(G-emisch ans 2
`Verbindungen)
`
`O;/ O‘/-‘Hr:-.
`
`Verbindung 88
`
`Verbindung 8.,
`
`Verbindung 84
`
`Verbindung 86
`(Gemisch aus 2
`Verbindungeu)
`
`\ - CH;
`/
`
`NH;
`
`J; c:~:;
`
`Verbindung 87
`
`105
`
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`25
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`30
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`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0526 -
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0526
`
`

`
`EP 0 831 799 B1
`
`SIZZR/_\,z~::~:—;
`WC»
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`V10
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`Verbindung 89
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`Verbindung 90
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`Verbindung 9]
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`.
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`£5
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`Verbindung 94
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`Verbindung 93
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`Verbindung 95
`
`Verbindung 96
`
`Verbindung 97
`
`
`
`Verbindung 98
`
`Verbindung 100
`
`Verbindung I01
`
`106
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0527
`
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`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0527
`
`

`
`EP 0 831 799 B1
`
`I/§)
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`I
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`. Verbindung 103
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`Verbindung 102
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`Verbindung I06
`
`10
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`25
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`30
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`35
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`40
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`50
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`55
`
`
`
`Verbindufig I07
`(Gemisch aus 2
`Verbindungen)
`
`Verbindung 108
`
`(Eye?
`<5
`
`Verbindung 114
`
`Verbindung 109
`
`Verbindung 111
`
`107
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0528
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0528
`
`

`
`EP 0 831 799 B1
`
`-
`
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`Verbindung 123
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`
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`Verbindung 124
`
`Verbindung 125
`
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`
`Verbindung 126 J
`
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`108
`
`Patent Owner, UCB Pharma GinbH — Exhibit 2007 - 0529
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0529
`
`

`
`EP 0 831 799 B1
`
`N82
`
`
`
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`
`Verbindung 127
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`Verbindung 128
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`Verbindung 132
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`fa’?-._.
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`Verbindung 137
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`Verbindung 138
`
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`109
`
`Patent Owner, UCB Pharmé GmbH — Exhibit 2007 - 0530
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0530
`
`

`
`EP 0 831 799 B1
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`
`
`Verbindung 139
`
`
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`:-:,co
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`Verbindung 142.
`
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`30
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`35
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`40
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`45
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`Verbindung 143
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`Verbindung. 144
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`Verbindung H8
`
`110
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - G531
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0531
`
`

`
`EP 0 831 799 B1
`
`5Y\I
`5-
`
`K/\\ /G
`U2
`
`Verbindung 150
`
`und pharmazeutisch vertréglichen Salzen und Komplexen davon ausgewéhlt ist, zur Herstellung eines Arzneimit-
`tels zur Behandlung von neurologischen Krankheiten oder Stdrungen.
`
`Verwendung gemafl Anspmch 1,wobei die Verbindung aus den Verbindungen 54-66, 68-71, 75, 76, 78, 79, 81-90,
`92-98,100,101,103,105,106,108,109,111,114-122,124-136,138,139,141-144,148-150 und phannazeutisch
`vertréglichen Salzen und Komplexen davon ausgewéhlt isl.
`
`Verwendung gem§l3 Anspruch 1, wobei die Verbindung aus den Verbindungen 54-66. 69, 70, 75, 76, 81-83, 85-97,
`100-103, 105, 106, 108, 109, 111, 115, 118-122, 125-133, 135-139, 142, 144-150 und pharmazeutisch vertr§gli-
`chen Salzen und Komplexen davon ausgewiéhlt ist.
`
`Verwendung geméfl Anspruch 1, wobei die Verbindung aus den Verbindungen 54-66, 69, 70, 75, 76, 81-83, 85-90,
`92-97,100,101,103,105,106,108,109,111,115,118-122,125-133,135,136,138,139,142,144,148-150 und
`pharmazeutisch venraiglichen Salzen und Komplexen davon ausgewéhlt ist.
`
`Ven/vendung gem§8 Anspruch 1, wobei die Verbindung aus den Verbindungen 54-66, 69, 82, 83, 89-97, 103, 111,
`118-120, 122, 126, 135-138, 142, 144, 145, 147-150 und pharmazeutisch vertréiglichen Salzen und Komplexen
`davon ausgewéhlt ist.
`
`Verwendung geméfl Anspruch 1, wobei die Verbindung aus den Verbindungen 54-66, 69, 82, 83. 89, 90, 92-97,
`103, 111, 118-120, 122, 126, 135, 136, 138, 142, 144, 148-150 und pharmazeutisch vertréglichen Salzen und
`Komplexen davon ausgewéhlt ist.
`
`Verwendung gemafl Anspruch 1, wobei die Verbindung aus den Verbindungen 60, 66, 69, 103, 111, 118-120, 122,
`136, 138, 142, 144, 148-150 und pharmazeutisch vertréglichen Salzen und Komplexen davon ausgewéhlt ist.
`
`Vewvendung geméfl Anspruch 1, wobei die Verbindung aus den Verbindungen 118-122, 137, 145, 148-150 und
`pharmazeutisch vertréglichen Salzen und Komplexen davon ausgewahlt ist.
`
`Verwendung gemafi Anspruch 1, wobei die Verbindung aus den Verbindungen 118-122, 148-150 und pharmazeu-
`tisch vervéglichen Salzen und Komplexen davon ausgewfihlt ist.
`
`Verwendung geméfl Anspmch 1, wobei die Verbindung aus den Verbindungen 63 und 64 und phannazeutisch
`vertrfiglichen Salzen und Komplexen davon ausgewéhlt ist.
`
`Verwendung gem5B Anspruch 1, wobei die Verbindung aus der Verbindung 119 und pharrnazeutisch vertréglichen
`Salzen und Komplexen davon ausgewéhlt ist.
`
`Verwendung geméll Anspruch 1, wobei die Verbindung aus der Verbindung 144 und pharmazeutisch vertraglichen
`Salzen und Komplexen davon ausgewéhlt ist.
`
`Venrvendung von Verbindung 60 und pharmazeutisch verttfiglichen Salzen und Komplexen davon zur Herstellung
`
`10
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`15
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`2D
`
`25
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`30
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`35
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`45
`
`10.
`
`11.
`
`55
`
`12.
`
`13.
`
`111
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0532
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0532
`
`

`
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`
`EP 0 831 799 B1
`
`eines Arzneimittels zur Behandlung von neurologischen Krankheiten oder Stérungen.
`
`14. Verwendung einer Verbindung der Formelz
`
`
`
`wobei:
`
`X unabhéngig aus -Br, -Cl. -F. -I, -CF3, einem Alkylrest, -OH, -OCF3. einem -O-Alkyl- und -O-Acylrest ausge-
`wéihlt ist;
`
`R1 unabhéngig aus -H, einem C,_4—AlkyI- und -0-Acylrest ausgewéihlt ist;
`R2 unabhangig aus -H, einem A|ky|- und Hydroxyalkylrest ausgewéihlt is! oder beide Reste R2 zusammen eine
`lminogruppe sind;
`R4 ein Phenoxyrest ist. der gegebenenfalls mit -F, -Cl, -Br. -I, -CF3, Alkyl,-OH. -OCF3. -0-Alkyl oder -O—Acyl
`substituiert ist; und
`m unabhéngig eine ganze Zahl von 0 bis 5 ist; und pharrnazeutisch vertrfiglicher Salze und Komplexe davon
`mit der Maflgabe, dass die Verbindung nicht:
`
`3-(p-Isopropoxyphenoxy)-3—phenyIpropylamin
`3-(2'-Methyl~4',5'-dichlorphenoxy)-3-phenylpropylamin
`3-(p-t-Butylphenoxy)-3-phenylpropylamin
`3'-(2',4'-DichIorphenoxy)«3-phenyl-2-methylpropyiamin
`3-(o-Ethylphenoxy)-3-phenylpropylamin
`3-(o—Methoxyphenoxy)-3-phenylpropylamin
`3-Phenoxy-3-phenylpropylamin ist,
`
`zur Herstellung eines Arzneimittels zur Behandlung von neurologischen Krankheiten oder Stérungen.
`
`15. Venwendung einer Verbindung der Formelz
`
`wobei:
`
`X unabhangig aus -F. -0, -Br, -I. -CF3, einem Alkylrest, -OH, -OCF3. einem -O-Alkyl— und -O-Acylrest ausge-
`wfihlt ist;
`
`R1 unabhangig aus —H. einem C,_4-Alkyl- und -0-Acylrest ausgewéhlt ist;
`R2 unabhéingig aus -H. einem C1_4-AlkyI- und Hydroxyalkylrest ausgewéhlt ist oder beide Reste R2 zusammen
`eine lminogruppe sind;
`R3 aus einer MethyI- und Ethylgruppe ausgewéhlt ist;
`R4 ein Phenoxyrest ist, der gegebenenfalls mit -F, ~Cl, -Br, ~I, -CF3. Alkyl.-OH, -OCF3, -0-Alkyl oder -O—Acyl
`
`112
`
`Patent Owner, UCB Pharma GmbH — Exhibit 2007 - 0533
`
`Patent Owner, UCB Pharma GmbH – Exhibit 2007 - 0533
`
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`10
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`25
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`30
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`35
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`40
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`45
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`50
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`55
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`EP 0 831 799 B1
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`substituierl ist; und
`m unabhangig eine ganze Zahl von 0 bis 5 ist; und pharmazeutisch venraglicher Salze und Komplexe davon.
`mit der Malsgabe. dass die Verbindung nicht:
`
`N-Methyl-3-(o-chlor-p¥toIyloxy)-3—phenyI—1-methylpropylémin
`N-Methyl-3-(p-tolyloxy)-3-phenylpropy1amin
`N-Methyl-3-(o-chlor-p-isopropylphenoxy)-3-phenyl-2-methylpropylamin
`N-Methyl-3-(p~iodphenoxy)-3-phenylpropylamin
`N-Methyl-3-(3-n-propylphenoxy)-3-phenylpropylamin
`N-Methyl-3-(p-trifluormethylphenoxy)—3-phenylpropylamin
`N-Methy|-3-(m-chIorphenoxy)-3-phenylpropylamin
`N-Methyl-3-(p—fluorphenoxy)—3-phenylpropylamin
`N-Methyl-3-(p—methoxyphenoxy)-3-phenylpropylamin
`N-Methyl-3-(o-methoxyphenoxy)-3-phenylpropyiamin
`N-Methyl-3-(o-fluorphenoxy)-3-phenylpropylamin
`N-Methyl-3-(0-tolyloxy)-3-phenylpropyiamin
`N-Methyl-3-(p-chlorphenoxy)-3-phenylpropyiamin
`N-Methyl-3-(m-fluorphenoxy)-3-phenylpropylamin
`N-Methyl-3-phenoxy-3-phenyl-2-methylpropylamin
`N:Methyl-3-phenoxy-3-phenyh1-methylpropylamin
`N-Methyl-3-phenoxy-3—phenylpropylamin
`N-Methyl-3-(o-trifluormethylphenoxy)-3-phenylpropylamin
`N-Methyl-3-(m-methoxyphenoxy)-3-phenylpropylamin
`N-Methyl-3-(o.p-difluorphenoxy)-3-phenylpropylamin
`N-Ethyl-3-(o—iodphenoxy)-3-phenylpropylamin
`N-Methyl-3-(o-chlorphenoxy)-3-phenylpropylamin
`N-Methyl-3-(o-bromphenoxy)~3-phenylpropylamin ist,
`
`zur Herstellung eines Arzneimittels zur Behandlung von neurologischen Krankheiten oder Stétungen.
`
`16. Verwendung einer Verbindung der Formel:
`
`wobei:
`
`(X)m aus einem meta-Fluor-. meta-Chlotatom, onho-O-CM-Alkylrest, einer ortho-Methylgruppe, einem ortho-
`Fluor-, ortho-Chloratom. meta-O-C1_4AlkyIrest, einer meta-Methylgruppe, ortho-OH und meta-OH ausgewfihlt
`ist;
`
`R1 H ist;
`R2 H ist;
`R3 aus einer Methyl- und Ethylgruppe ausgewéhlt ist;
`R4 ein Phenoxyrest ist. der gegebenenfalls mit -F. -Cl, -Br, -I. -CF3, AIkyl,—OH, -OCF3. -O-Alkyl oder -O-Acyl
`substituiert ist; und
`pharmazeutisch vertréglicher Salze und Komplexe davon zur Herstellung eines Arzneimittels zur Behandlung
`von neurologischen Krankheiten oder Stérungen.
`
`17. Venn/endung gemafl einem der Ansprfiohe 1 bis 16, wobei die neurologische Krankheit oder Stérung Schlaganfall.
`Schédeltrauma. Rfickenmarksvedetzung, Rflckenmalksischémie, eine durch lschéimie oder Hypoxie bedingte
`Sch