WO 99/37630
`
`PCT/US99/01318
`
`20 / 50
`E
`o,
`
`Bu 0
`
`4
`
`F.
`'/ %
`
`O,
`
`Bu 0
`
`15
`
`0 X
`
`Kl/ 0
`N^N3
`
`1. Ph3P
`2. BAL resin, A
`3. NaBHaCN
`
`O X
`
`N'
`
`i
`
`H r*
`
`1. TMSCI, PhOH
`2. AC2O, pyridine
`3. PfpOCOCFs, pyridine
`
`F.
`// %
`
`O X
`
`it 0 Ac
`
`0,
`
`PfpO
`
`17
`
`CH(CN)2NH2
`TsOH, pyridine
`
`F
`O X
`NC^N ^ \\ M 0 Ac
`0
`H2N
`
`\\
`
`86
`
`TFA
`
`F.
`0 X
`// % N ? H
`"Ac
`
`NC^N
`ss
`\
`0
`
`H2N
`
`87
`
`FIGURE 20
`
`2357
`
`MYLAN - EXHIBIT 1004 Part 6 of 10
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`21 / 50
`
`O
`N 0
`
`AC
`
`'/ %
`
`o
`
`PfpO
`
`17
`
`HN(OCH3)CH3
`P/. DMF
`
`F,
`
`0
`
`O
`
`^0
`kj 0 Ac
`
`CH3O-N
`CH3
`
`88
`
`LiAIH^
`THF
`
`O
`M'' O Ac
`
`X
`
`Fv
`
`o
`
`89
`
`TFA
`DCM
`
`O
`
`X
`R
`0
`f % t r y H
`
`Ac
`
`90
`
`MeMgl
`THF
`
`F>
`
`0
`
`H3C
`
`O
`M 0 Ac
`^0
`
`91
`
`TFA
`DCM
`
`o
`H3C
`
`X
`0
`N ' 7 H
`
`Ac
`
`92
`
`FIGURE 21
`
`2358
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`22 / 50
`
`0
`Fv
`// \ IJ O
`^0
`
`Ac
`
`HjN
`
`/—CHO
`O
`
`CHO
`
`HC(OEt)3
`NaBH3CN
`
`79
`
`H(0)C,
`
`OCH3
`o
`
`OCH3
`AcOH, A
`
`0
`
`N—K
`
`O
`N' 0 Ac
`
`X
`
`O
`
`H
`
`Fv
`
`N—\ \
`
`0
`^0
`N O
`
`Ac
`
`93
`
`TFA
`DCM
`
`95
`
`TFA
`DCM
`
`Fx
`
`/—\
`N—('
`0
`w
`
`O
`
`\N
`
`N
`
`| H
`vAc
`
`94
`
`0
`
`H
`
`Fx
`
`O
`^0
`N
`| H
`N—K \
`
`Ac
`
`96
`
`FIGURE 22
`
`2359
`
`

`

`a
`o
`vO o
`V)
`S
`n H
`
`00
`
`O
`Ul
`OS
`OJ -a
`VO
`V0
`O
`5=
`
`O
`Lrt
`
`OJ
`NJ
`
`•
`
`Cleavage
`
`FIGURE 23
`
`R3
`
`.0
`
`16b
`
`15a
`
`Rx
`
`Acylation
`
`Q-o
`
`equivalent
`phosgene
`
`7a
`
`R2
`
`o
`
`R3NH2
`
`(^OYK^>RI2
`
`•
`
`formation
`epoxide
`
`R2
`
`6a
`
`o
`
`O
`
`Rio Rn o
`
`8a
`
`O
`R2
`II
`I Rio
`Y N ^rTy^ NH
`
`n
`
`m
`
`fio ^OH
`
`^ H
`
`16a
`
`R3
`
`R2 R12
`n
`Nv
`
`T
`
`m
`
`H2N
`
`2360
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`,0
`
`O
`
`12a
`
`PhNH(CO)OCH2Ph
`«-BuLi
`
`Q-4
`
`O OH NHPh
`)->
`HN—'
`
`19a
`
`CDI
`NMM
`
`24 / 50
`
`PhNH2
`
`LiOTCACN
`
`O A
`Q-i V
`
`_ O O NPh
`
`HN—
`
`20a
`
`TFA (90%)
`
`O A o NPh
`
`HzN
`
`21a
`
`acetyl chloride
`EtjN
`
`O A O NPh
`
`AcHN
`
`22a
`
`FIGURE 24
`
`2361
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`25 / 50
`
`p
`
`NH2CH2CHCH2
`
`0-C6H4N02
`
`23a
`
`wCPBA
`
`o
`
`p
`
`HN-
`
`%
`
`24a
`
`o
`
`p vO
`
`HN-
`
`12a
`
`NH2C6H3F(C4H8NO)
`
`F
`
`N
`
`O
`
`%
`
`//
`
`CDI
`
`F
`
`O OH HN
`
`^ //
`
`/
`N
`\
`
`\
`O
`/
`
`O A
`
`N
`
`Q 0
`
`O
`
`HN
`
`TFA
`
`26a
`
`25a
`
`F
`
`^ //
`
`/—\
`O
`N
`
`0
`A
`
`N
`
`O
`
`F
`
`\ //
`
`/
`N
`
`\
`0
`
`acetyl
`chloride
`
`O
`
`A
`
`O
`
`N
`
`HzN
`
`27a
`
`HN
`0=<
`CH3
`
`28a
`
`FIGURE 25
`
`2362
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`26 / 50
`
`O
`
`HO
`
`OMe
`
`CHO
`
`^ //
`OMe
`
`30a
`
`DIG
`
`Q-NI-U
`
`29a
`
`O
`
`OMe
`
`W
`
`CHO
`
`//
`OMe
`
`31a
`
`F
`
`O
`O-f
`/—\
`o
`^N~A // N
`H2N^.-
`32a
`
`NaBHjCCN)
`
`O
`
`Q-N
`
`H
`
`O
`
`N
`
`CN~\\ // N
`
`o
`
`OMe
`
`w //
`
`OMe
`
`33a
`
`FIGURE 26
`
`2363
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`27 / 50
`
`O
`O-7?
`^N-C6H3F(C4H8NO)
`
`Q-N
`
`R6S02X
`
`RfiNCO
`
`33a
`
`O
`R6"S02 o-f
`Q-N ^,^N-C6H3F(C4H8NO)
`
`R6C(0)X
`
`^HN^O O_^0 O-N^.i^N-W^HaNO)
`
`34a
`
`cleavage
`
`R^0 o-f
`^N-C6H3F(C4H8NO)
`
`Q-U
`
`36a
`
`38a
`
`cleavage
`
`R6"SO2 o-f
`(V^N-C6H3F(C4H8NO)
`HN
`
`cleavage
`
`R6HN
`
`Y0 p-f C6H3F(C4H8NO)
`
`35a
`
`39a
`
`R6^0 o-i
`(^N-CgHaF^HgNO)
`HN
`
`37a
`
`FIGURE 27
`
`2364
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`28 / 50
`
`O
`9-^
`/^/N-C6H3F(C4H8NO)
`
`Q-N
`
`33a
`
`H02CCH2Br
`
`v ?^0
`
`Q-N
`
`^N-C6H3F(C4H8NO)
`
`RfiSH
`K2C03
`
`SR 6
`
`V°-f
`
`Q-N ^N-C6H3F(C4H8NO)
`
`40a
`
`1. PPh3
`2. Base
`3. R^CHO
`
`R6R7NH
`K2C03
`
`NR,R,
`
`0 YM
`
`Q-N
`
`^/N-C6H3F(C4H8NO)
`
`41a
`
`R 6
`
`45a
`
`TFA (90%)
`
`Q-N
`
`^N-C6H3F(C4H8NO)
`
`TFA (90%)
`
`SR6 Vo-f
`
`HN
`
`^N-CeHaF^HaNO)
`
`42a
`
`Re
`
`43a
`
`TFA (90%)
`
`r*
`r 1
`HN
`
`o
`^N-C5H3F(C4H8NO)
`
`46a
`
`(^N-CeHgF^HaNO)
`HN •w^''
`
`44a
`
`FIGURE 28
`
`2365
`
`

`

`WO 99/37630
`
`F
`
`29 / 50
`
`N
`
`•N
`
`N—<\
`
`h NH2
`
`O2N
`
`PCT/US99/01318
`
`F.
`
`•N
`
`O
`
`N—(\ ri—NH2
`\ /
`
`(=N
`^ //
`
`F
`
`N
`\
`
`N—<\
`/
`
`/) NH2
`
`F
`
`NHx
`
`/ ) NH2
`
`F
`
`,N-\\ /r-NH^
`
`F
`
`\
`/
`O N~\ /)—NH2
`
`F
`
`S
`
`N—(\
`
`/)—NH2
`
`N'
`'J ^
`
`F.
`^ / / ™ 2
`
`F
`
`F.
`
`\
`N—(\
`/
`
`/
`R-N
`\
`
`/)—NH2
`
`0,
`
`H3C
`
`\\ /-NH>
`
`H3CO-y^
`
`O
`
`^ U
`
`N H2
`
`F.
`
`H3CO^/^
`
`O'
`
`H
`
`o
`
`^ /) NH2
`
`F
`
`^ /-nh2
`
`F
`
`F
`
`0:
`
`MX //-NH2
`
`N
`H02C~--/
`
`^ / ~ N H 2
`
`AcN-
`
`\\ //-NH2
`
`F
`
`S C
`
`N—(\
`/
`
`/>—NH2
`
`HO. •y N
`
`F.
`
`N
`
`\v / / ' N H 2
`
`FIGURE 29
`
`2366
`
`

`

`WO 99/37630
`
`O
`
`R-N
`
`30 / 50
`
`/^NH2
`
`PCT/US99/01318
`
`Br
`
`'I
`
`\N
`
`NH2
`
`S^NH2
`0HC"A /rAj
`
`c=N
`OHC-\\ /?-% rNH2
`
`H,C
`
`'/
`O
`
`N
`
`H3C-< o
`
`N
`
`NH2
`
`NH2
`
`NH2
`
`N
`
`NH2
`
`NH2
`H v
`
`//
`
`NH2
`
`FIGURE 30
`
`H3C
`J \
`N
`0=<
`s
`
`NH2
`
`•NH2
`
`CI
`
`Br
`
`•NH2
`
`SX N—'
`
`N
`H3C—^
`s
`
`N
`
`H3C—< o
`
`N
`H3CS—^
`S
`
`NH2
`
`NH2
`
`NH2
`
`H3C
`
`N
`
`NH2
`
`N=N
`\\ /r\ tNH2
`
`2367
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`N—'
`
`\\
`
`/) NH2
`•N
`
`31/50
`H3C
`J \
`N
`
`N
`
`NH2
`
`H3C
`N
`o=<
`N > NH2
`H3C
`
`R
`
`N
`
`%
`
`•NH2
`
`N
`
`N
`//
`
`H3C
`
`NH2
`
`H3CS
`
`N
`
`N
`//
`o
`
`NH2
`
`R
`0^ .N
`
`i
`
`R.
`N
`
`O
`
`N
`
`NH2
`
`N
`H3C ^
`
`N NH2
`
`O
`
`N
`
`RN
`
`\\ //-NH^
`
`RN
`
`\\ //-NH^
`
`RN\
`
`// \ /"NH2
`
`NH2
`
`NH2
`
`NH2
`
`N NH2
`
`H3C
`N
`
`O
`
`w
`
`RN
`
`\\ //-^
`
`N
`
`N-,
`
`/RNH2
`
`Br'
`
`FIGURE 31
`
`2368
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`32 / 50
`o
`
`H3C
`
`o
`A
`N O
`
`o A
`o
`
`•N
`
`// %
`
`o
`
`H3C
`
`•NH2
`
`•NH2
`
`t—s
`s
`N
`
`// ^
`
`o A
`o
`
`•N
`
`N'
`//
`
`^
`
`o A
`
`O
`
`•N
`
`•NH2
`
`•NH2
`
`o A
`
`O
`
`•N
`
`•NH2
`
`•NH2
`
`/
`—N
`
`N
`
`O
`
`\
`N- ^ //
`
`O2N
`
`// w
`
`RN
`
`N-
`
`o A
`
`O
`
`•N
`
`FIGURE 32
`
`2369
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`?
`
`s
`
`Z
`
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`
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`FIGURE 33
`
`2370
`
`

`

`34 / 50 ©
`o
`di
`Q i
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`K)
`
`Z
`X
`N
`
`WO 99/37630
`
`©
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`WO 99/37630
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`PCT/US99/01318
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`NHNH2
`
`N NH2 HO N OH O
`N
`
`y^NH
`AN
`
`H2N
`
`HOOC
`
`Ph
`
`N^NH2
`
`Vs
`X^NH A
`
`NH2
`
`1
`OH
`
`NH2
`
`NH2
`
`1
`N
`N
`R^NH2
`
`a
`
`OH
`
`"^N"
`
`H
`N
`
`6L
`o
`
`NH2
`
`NH2
`OH
`
`(J^T
`
`OH
`V^NH,
`
`5H
`^r^NHs
`
`HS
`)=N
`N^VsH
`2N NH2
`
`N NH2
`OL
`
`N-NH2
`
`N=/
`N^,
`
`NH,
`H2N
`0 k
`s^02 s-^s^N^ >NH
`M S>-NH
`RN
`CO2H
`i*
`N
`^-COz'Bu
`
`^VNH,
`
`H2N
`
`SH H2N
`
`irti N
`
`NH2
`
`s-^
`_^N
`H2N
`
`Ph
`
`NH2
`
`I
`
`N
`
`NH,
`
`NH2
`
`NH2
`
`rV1
`
`N
`
`N-N
`
`S
`'!>-NH2
`N
`
`NH2 COOH
`
`NH2
`
`s
`
`AcHN
`
`S
`>
`N
`
`O
`
`HO
`
`(T^N
`
`NHz
`
`H
`llNV>-NH2
`
`TMSONHZ
`
`SH
`
`N=C
`
`NH2
`
`NHBoc
`
`H2N
`
`r*
`JV"*
`
`F3C
`
`0^<<?
`0rs
`
`N COOH
`
`2N
`
`NH2
`
`2384
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`48 / 50
`
`LrO-0'
`
`<•>
`x
`O x
`o WO
`o-f
`
`I
`
`o
`o
`
`O
`Q:
`
`a: >=o
`x z
`O
`o z
`
`CO
`
`LLT
`o z
`(N tz
`
`i
`
`(& o
`
`^4
`
`z
`
`u.
`
`•O.
`
`_£J
`
`z 0
`
`x1
`Z
`
`X
`
`X^
`
`%
`
`X
`
`o
`
`z
`
`Z:
`
`x'
`
`^CNj
`
`A
`
`^ 2
`
`X
`
`tN
`
`z s
`o I
`o
`
`X
`
`CM
`
`z s
`os
`
`x.
`
`?
`
`CO
`
`UJ
`OH
`ZD <3
`
`I I
`
`^fN
`
`r
`
`z
`Z'O
`
`X
`
`<M
`
`z
`
`0}
`
`X
`z
`
`<~z
`
`z
`
`X
`Q:
`o:
`
`CO
`
`CM
`
`M
`X
`
`6
`
`? £
`&z
`
`tz
`
`o
`
`pg
`
`z
`
`o«
`
`z
`
`(Li
`
`z
`
`C.Z
`
`CM
`
`&
`
`n
`X
`o
`
`CM
`X
`z
`.o.
`' i
`^.z
`
`u
`
`o
`
`X
`
`z
`
`o
`
`X
`
`s
`o.
`
`z
`<0
`X
`z^o
`M -
`
`CN
`
`z
`,vV0
`o o
`X X
`
`£
`
`z s J0-X O.
`
`CN
`
`tj
`o
`
`&
`p
`
`X
`
`o
`I
`
`CM
`
`z r^o
`.43r Z^
`h
`
`IL
`
`CM
`X
`
`o.
`o.
`
`^z
`
`CM
`
`z 0
`
`o
`
`I
`
`^Z
`i
`o
`
`X
`
`x1
`
`If-
`
`X z
`NX
`z
`Q
`
`2385
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`OH 49 / 50
`
`X-f~V OH
`MM
`I
`V-^SVOH
`
`D=A
`
`COYs
`
`Y = leaving group:
`CI, Imidazolyl, etc.
`
`D
`
`CI
`X = COOR, NHR, SR;
`R = removable protective group:
`t-Bu, Boc, Trt, etc. as appropriate
`for a given X;
`A-D = one or two N atoms, S, CH, or
`substituent group at C atom, or one
`of these equal zero
`
`Q
`
`C-B
`
`o
`
`C-B
`
`I.CH3SO2CI
`NEt3
`2. NaN
`
`OH
`
`Q
`XHP"VN:
`D=A
`
`O
`
`R-IZ, base
`
`Q
`
`1
`
`Q
`
`o
`NH
`
`H <X
`1. PPh3t THF, A
`2. NaBHaCN
`
`Polymer is BAL resin
`
`Polymer is BAL resin
`
`1.TMSCI, PhOH
`2. Pfp02CCF3
`base, NMP
`3. R2NHR3 A
`4. TFA, DCM>/
`
`For X =
`t-Bu02C
`
`Q
`
`q. C-BK
`R2-NN D=A ^V-NH
`R1
`R-I =RftcO, RSO2, RNR'CO,
`ROCO, etc.
`
`Q
`
`Polymer is BAL resin
`
`For X =
`t-BuOjC
`
`1.TMSCI, PhOH
`2. PfpOzCCFa
`base, NMP
`3. TMSN3, TBAF
`4. FmOH, A
`5. Piperdine, DMF^f
`6. R2Z, base
`Q
`O
`R2-NH<^ V
`N VJV.NH^
`D=A
`R 1
`R i , R2 = RCO, RSO2, RNR'CO,
`ROCO, etc.
`
`1. R2Z, MeONa
`2. TFA, DCM
`
`Q
`
`For X =
`RCOS
`
`NH
`
`"R
`1
`R, = RCO, RS02, RNR'CO,
`ROCO, etc.; R2 = alkyl, aryl,
`heteroalkyl, heteroaryl, etc.
`
`FIGURE 49
`
`2386
`
`

`

`WO 99/37630
`
`PCT/US99/01318
`
`Synthesis from 5-(S)-azidomethyioxazolidinone
`
`50 / 50
`
`NaNa or
`BU4N+N3"
`
`O
`O
`Nti^x
`X = leaving group:
`CI, Br, I, OMs
`As described in preceding
`Figure 49
`
`Q
`
`N ^ N 3
`
`XYC:'B Vc,
`
`base
`
`Q
`C-B Ko
`x-c VK 5
`D=A
`
`Q
`
`Polymer is BAL resin
`
`X = COOR, NHR, SR;
`R = removable protective group:
`t-Bu, Boc, Trt, etc. as appropriate
`for a given X;
`A-D = one or two N atoms, S, CH,
`or substituent group at C atom,
`or one of these equal zero
`
`Synthesis from 5-(S)-(protected amino)methyloxazolidinone
`X
`
`V
`"tiX-
`X
`X = leaving group:
`CI, Br, I, OMs
`
`Trt-NH2
`
`Q
`
`V
`O
`NtiA^NHTrt
`Trt = (triphenyl)methyl
`
`TTf
`•..A
`
`CI
`
`base
`
`Q
`C-B Kr,
`*-4. D=A
`
`NHTrt
`
`H+
`
`e.g., AcOH
`
`o
`
`a
`H <X
`
`NH2
`
`1. NaBHsCN
`2. R^, base
`
`%
`
`Polymer is BAL resin
`
`X = COOR, NHR, SR;
`R = removable protective group:
`t-Bu, Boc, Trt, etc. as appropriate
`for a given X;
`A-D = one or two N atoms, S, CH,
`or substituent group at C atom,
`or one of these equal zero
`
`FIGURE 50
`
`2387
`
`

`

`INTERNATIONAL SEARCH REPORT
`
`Inte
`Jonal Application No
`PCT/US 99/01318
`
`A. CLASSIFICATION OF SUBJECT MATTER
`,
`,
`IPC 6
`C07D263/20 C07D413/12 C07D417/12 C07F9/653
`C07D413/04
`
`C07D417/04
`
`According to International Patent Classification (IPC) or to both national classification and IPC
`B. FIELDS SEARCHED
`Minimum documentation searched (classification system followed by classification symbols)
`IPC 6
`C07D C07B A61K C07F
`
`Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched
`
`Electronic data base consulted during the international search (name of data base and, where practical, search terms used)
`
`C. DOCUMENTS CONSIDERED TO BE RELEVANT
`Category0 Citation of document, with indication, where appropriate, of the relevant passages
`
`Relevant to claim No.
`
`X
`
`X
`
`X
`
`WO 97 30981 A (PHARMACIA & UPJOHN CO)
`28 August 1997
`
`see claims
`
`WO 97 21708 A (PHARMACIA & UPJOHN CO )
`19 June 1997
`
`see claims
`
`WO 98 01446 A (ZENECA LTD )
`15 January 1998
`
`see claims
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`m Further documents are listed in the continuation of box C.
`
`0 Special categories of cited documents :
`
`"A" document defining the general state of the art which is not
`considered to be of particular relevance
`"E" earlier document but published on or after the international
`filing date
`"L" document which may throw doubts on priority claim(s)or
`which is cited to establish the publication date of another
`citation or other special reason (as specified)
`"O" document referring to an oral disclosure, use, exhibition or
`other means
`"P" document published prior to the international filing date but
`later than the priority date claimed
`
`| Patent family members are listed in annex.
`
`T" later document published after the international filing date
`or priority date and not in conflict with the application but
`cited to understand the principle or theory underlying the
`invention
`"X" document of particular relevance; the claimed invention
`cannot be considered novel or cannot be considered to
`involve an inventive step when the document is taken alone
`"Y" document of particular relevance; the claimed invention
`cannot be considered to involve an inventive step when the
`document is combined with one or more other such docu­
`ments, such combination being obvious to a person skilled
`in the art.
`document member of the same patent family
`
`Date of the actual completion of the international search
`
`Date of mailing of the international search report
`
`21 April 1999
`
`Name and mailing address of the ISA
`European Patent Office, P.B. 5818 Patentlaan 2
`NL - 2280 HV Rijswijk
`Tel. (+31-70) 340-2040, Tx. 31 651 epo nl,
`Fax:(+31-70) 340-3016
`
`1
`
`Form PCT/ISA/210 (second sheet) (July 1992)
`
`03/05/1999
`
`Authorized officer
`
`Henry, J
`
`page 1 of 4
`
`2388
`
`

`

`INTERNATIONAL SEARCH REPORT
`
`Intt
`donal Application No
`PCT/US 99/01318
`
`C.(Continuation) DOCUMENTS CONSIDERED TO BE RELEVANT
`Category ° Citation ot document, with indication,where appropnate, of the relevant passages
`
`Relevant to claim No.
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`WO 98 01447 A (ZENECA LIMITED)
`15 January 1998
`
`see claims
`
`WO 95 14684 A (UPJOHN CO ) 1 June 1995
`
`see claims
`
`US 4 801 600 A (WANG CHIA-LIN J
`31 January 1989
`
`ET AL)
`
`see claims
`
`WO 93 09103 A (UPJOHN CO) 13 May 1993
`
`see claims
`
`WO 93 23384 A (UPJOHN CO )
`25 November 1993
`
`see claims
`
`WO 94 13649 A (UPJOHN CO ) 23 June 1994
`
`see claims
`
`WO 95 07271 A (UPJOHN CO ) 16 March 1995
`
`see claims
`
`WO 97 10223 A (PHARMACIA & UPJOHN CO )
`20 March 1997
`
`see claims
`
`EP 0 127 902 A (DU PONT DE NEMOURS)
`12 December 1984
`
`see claims
`
`EP 0 184 170 A (DU PONT DE NEMOURS)
`11 June 1986
`
`see claims
`
`EP 0 312 000 A (DU PONT DE NEMOURS)
`19 April 1989
`
`see claims
`
`7-9,
`13-43,
`60-82,95
`
`7-9
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`1
`
`Form PCT/1SA/210 (continuation of second sheet) (July 1992)
`
`page 2 of 4
`
`2389
`
`

`

`INTERNATIONAL SEARCH REPORT
`
`Inte
`.ional Application No
`PCT/US 99/01318
`
`C.(Continuation) DOCUMENTS CONSIDERED TO BE RELEVANT
`Category ° Citation of document, with indication,where appropriate, of the relevant passages
`
`Relevant to claim No.
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`X
`
`A
`
`A
`
`P,A
`
`EP 0 316 594 A (DU PONT DE NEMOURS)
`24 May 1989
`
`see claims
`
`EP 0 352 781 A (DU PONT DE NEMOURS)
`31 January 1990
`
`see claims
`
`EP 0 359 418 A (UPJOHN CO) 21 March 1990
`
`see claims
`
`EP 0 694 543 A (BAYER AG) 31 January 1996
`
`see claims
`
`EP 0 693 491 A (BAYER AG) 24 January 1996
`
`see claims
`
`DE 196 49 095 A (BAYER AG) 7 August 1997
`
`see claims
`
`DE 196 04 223 A (BAYER AG) 7 August 1997
`
`see claims
`
`W0 97 19039 A (N0VARTIS AG) 29 May 1997
`
`see claims
`
`"COMBINATORIAL
`BALKENHOHL F ET AL:
`SYNTHESIS OF SMALL ORGANIC MOLECULES"
`ANGEWANDTE CHEMIE. INTERNATIONAL EDITION,
`vol. 35, no. 20, 1996, pages 2288-2237,
`XP002065423
`see the whole document
`
`BUCHSTALLER H -P:
`"Solid Phase Synthesis
`of Oxazolidinones via a Novel
`Cycl1sation/Cleavage Reaction"
`TETRAHEDRON,
`vol. 54, no. 14, 2 April 1998, page
`3465-3470 XP004110492
`see the whole document
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`7-9
`13-43,
`60-82,95
`
`7-9,
`13-43,
`60-82,95
`
`1-6
`44-54
`
`1-6,
`44-54
`
`1-6,
`44-54
`
`1
`
`Form PCT/ISA/210 (continuation of second sheet) (July 1992)
`
`page 3 of 4
`
`2390
`
`

`

`INTERNATIONAL SEARCH REPORT
`
`Intt
`.ional Application No
`PCT/US 99/01318
`
`C.(Continuation) DOCUMENTS CONSIDERED TO BE RELEVANT
`
`Category ° Citation of document, with indication,where appropriate, of the relevant passages
`
`Relevant to claim No.
`
`P,A
`
`"Solid-Phase Synthesis
`HOLTE P T ET AL:
`of 3,5-Disubstituted 1,3-Oxazolidin-2-ones
`by an Activation/Cyclo-elimination
`Procpss"
`TETRAHEDRON LETTERS,
`vol. 39, no. 40, 1 October 1998, page
`7407-7410 XP004133693
`see the whole document
`
`1-6,
`44-54
`
`1
`
`Foim PCT/ISA/210 (continuation of second sheet) (July 1992)
`
`page 4 of 4
`
`2391
`
`

`

`INTERNATIONAL SEARCH REPORT
`
`luernational application No.
`
`PCT/US 99/01318
`
`Box I Observations where certain claims were found unsearchable (Continuation of item 1 of first sheet)
`
`This International Search Report has not been established in respect of certain claims under Article 17(2)(a) tor the following reasons:
`
`1. | X | Claims Nos.:
`95-100
`because they relate to subject matter not required to be searched by this Authority, namely:
`Remark: Although claims 95-100
`are directed to a method of treatment of the human/animal
`body, the search has been carried out and based on the alleged
`effects of the compound/composition.
`
`2. 1
`
`[ Claims Nos.:
`because they relate to parts of the International Application that do not comply with the prescribed requirements to such
`an extent that no meaningful International Search can be carried out, specifically:
`
`3. |
`
`| Claims Nos.:
`because they are dependent claims and are not drafted in accordance with the second and third sentences of Rule 6.4(a).
`
`Box II Observations where unity of invention is lacking (Continuation of item 2 of first sheet)
`
`This International Searching Authority found multiple inventions in this international application, as follows:
`
`\
`1
`
`j As all required additional search fees were timely paid by the applicant, this International Search Report covers all
`1 searchable claims.
`
`2. 1
`
`| As ail searchable claims could be searched without effort justifying an additional fee. this Authority did not invite payment
`of any additional fee.
`
`3. |
`>
`
`I As only some of the required additional search fees were timely paid by the applicant, this International Search Report
`1 covers only those claims for which fees were paid, specifically claims Nos.:
`
`4. |
`
`| No required additional search fees were timely paid by the applicant. Consequently, this International Search Report is
`restricted to the invention first mentioned in the claims; it is covered by claims Nos.:
`
`Remark on Protest
`
`| | The additional search fees were accompanied by the applicant's protest.
`
`|
`
`| No protest accompanied the payment of additional search fees.
`
`Form PCT/ISA/210 (continuation of first sheet (1)) (July 1998)
`
`2392
`
`

`

`INTERNATIONAL SEARCH REPORT
`Information on patent family members
`
`Intb
`tionai Application No
`PCT/US 99/01318
`
`Patent document
`cited in search report
`
`WO 9730981
`
`WO 9721708
`
`WO 9801446
`
`WO 9801447
`
`WO 9514684
`
`A
`
`A
`
`A
`
`A
`
`A
`
`Publication
`date
`
`28-08-1997
`
`19-06-1997
`
`15-01-1998
`
`15-01-1998
`
`01-06-1995
`
`US 4801600
`
`A
`
`31-01-1989
`
`WO 9309103
`
`A
`
`13-05-1993
`
`W0 9323384
`
`A
`
`25-11-1993
`
`Patent family
`member(s)
`
`1954797 A
`2243706 A
`0883611 A
`
`1407797 A
`2236677 A
`0868424 A
`
`3352097 A
`
`3352197 A
`
`698699 B
`8010394 A
`2174107 A
`1135752 A
`0730591 A
`9505582 T
`274966 A
`5652238 A
`9407885 A
`
`2350788 A
`1322001 A
`562888 A
`0311090 A
`884610 A
`1132569 A
`88713 B
`1616518 A
`4921869 A
`4985429 A
`5032605 A
`4965268 A
`5036093 A
`5036092 A
`5039690 A
`
`146783 T
`667198 B
`2689892 A
`2119556 A
`69216251 D
`69216251 T
`610265 T
`0610265 A
`3022340 T
`7500603 T
`5565571 A
`58