EXHIBIT 1006
`
`

`

`
`
`THE
`
`MERCK INDEX
`
`AN” ENCYCLOPEDIA OF
`
`CHEMICALS, DRUGS, AND BIOLOGICALS
`
`FOURTEENTH EDITION
`
`Maryadele J. O’Neil, Editor
`
`Patricia E. Heckelman, Senior Associate Editor
`
`Cherie B. Koch, Associate Editor
`
`Kristin J. Roman, Assistant Editor
`
`Catherine M. Kenny, Editorial Assistant
`Maryann R. D’Arecca, Administrative Associate
`
`Published by
`Merck Research Laboratories
`
`Division of
`
`MERCK & C0., INC.
`Whitehouse Station. NJ, USA
`
`2006
`
`
`
`é,
`
`a§§
`
`,metwpw,,,M
`wwwmw«aw.FEM-40H“rxarl
`
`EDITION
`
`

`

`Library of Congress Catalog Card Number 89-60001
`ISBN Number 0-9l l9l0-OO~X
`ISBN Number 978-0-91 1910-00-l
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`ganic Name
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`The Suppl
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`Copyright © 2006 by MERCK & CO.. INC. Whitehouse Station, NJ. USA
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`All rights reserved. No part of this book or electronic product may be reproduced or used in any form or by any means.
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`Printed in the USA
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`

`1121
`
`Benztropine Mesylate
`
`in alkaline solns. L1)... in mice. rats (mg/kg): >5000. >10000
`orally: 410. 422 i.v. (P‘an).
`THERAPCAT: Diuretic. antihypcr’tensivc.
`
`1121. Benztropine Mesylate. {132-17‘21 3—(Diphenylmeth—
`oxy)-8-mcthyl-X-azabicyclol3.2.1 loctane mcthanesullbnate; 3a-(di—
`phenylmcthoxy)-1all,5(xlI-tropane melhanesull'onate: henztropinc
`ntethancsull'onatc: tropinc benzohydryl ether methanesulfonalc: Co.
`gentin;Cogen1inol. C23 H3.,NO4 S: mol wt 403.53. C 65.48%. H
`7.24%. N 3.47%. () 15.86%. S 7.95%. Anticholinergic. Prepd by
`the action 01‘ diphenyldiazomethane on tropine: Phillips. US
`2595405 (1952 to Merck & Co.). Crystal structure: P. G. Jones
`1'! a/.,/1r'ta (Tut's/allow: 1134. 3125 ( 1978).
`CH3
`
`
`
`
`
`
`
`
`
`
`
`
`CH3803H
`
`Crystals from acetone + ether. mp 143°. uv max: 259 nm (EM =
`437). Soluble in water. pH about 6.
`THERAPCA'I‘: Antiparkinsonian.
`
`I642-72-8] N.N~Dimethyl-3—ll l<
`1122. Benzydamine.
`(phenylmethyl)—lH-ittdazol-3~ylloxyl—l-propanarnine: 1-benzyl-3-
`[3-(dimethylamino)propoxy]~lH-indazole: l-bcnzyl-lH-indazol-3-
`yl 3-(dimetltylamino)propy1 ether: benzindamine. C19H33N3O:
`mol wt 309.41. C 73.75%. H 7.49%. N 13.58%. 0 5.17%. Prepn:
`FR 1382855: Palazzo. US 3318905 (1964. 1967 both to Angelini
`Francesco): Palazzo er (1].. J. Mm]. Chem. 9. 38 (1966). Pharma-
`cology: Lisciani (It (1].. Ell/1.]. I’lmrmuml. 3. 157 (I968). Metab-
`olism: Catancse (’l u/.. Armcim.~I-‘orxt'l1. 16. 1354 (1966): Kataoka
`«I (1].. Chem. l’hurm. Bull. 19, 151 l (1971). Toxicology: B. Silv
`vestrini (it (11., Ttt.t‘l('()l. App]. lernmt'ol. 10. 148 (1967). Series of
`articles on phannacology: /1r:m'im.—Frir.t‘t'/1. 37. 587-646 (1987).
`
`\N
`/
`
`CH
`O/\/\ N/ 3
`H3
`
`IC
`
`b130.05 [60°-
`
`Hydrochloridc. 1132-69-4] Ailoben; Andolex: Benzyrin: Dif-
`flam: Enzamin: ltnotl‘yl: Opalgyne: Riripen: Salyzoron; Sanitior:
`Tamas: Tantum: Verax. C..,1'13_.N30.1--1C1; mol wt 345.87. Crys-
`tals. mp 160". uv max: 306 nm (E13,. 160). Very sol in water:
`rather sol in ethanol. chloroform. n~bu1anol. LDSIJ in mice. rats
`(mg/kg): 110. 100 i.p.: 515. 1050 orally (Silvestrini).
`THERAP CAT: Analgcsic: anti-inflammatory: antipyretic.
`‘I‘HliRAl'CA'I’tVE'l‘i: Anti-inflammatory.
`
`| 140-1 1-41 Acetic acid phenylmeth-
`1123. Benzyl Acetate.
`yl ester: acetic acid benzyl ester. C.,Hm()3: mol wt 150.17. C
`71.98%. H 6.71%. O 21.31%. C6115CHZOOCCH3. Occurs in a
`number of plants. particularly jasminc: S. Arctander. Per/”tum: um]
`Flavor Malaria/.1: (:fNqurr/l Origin (Elizabeth. N.J.. 1960) pp 313
`314. Prepd from benzyl chloride. acetic acid or sodium acetate and
`triethylamine: Merker. Scott. .1. Org. Chem. 26, 5180 (1961 ): Hen—
`nis e! ul.. Ind. Eng. Clmu. Prod. Res. Dev. 6. 193 (1967). Toxicity
`study: P. M. Jcnner cl (1].. [’01er C(M‘flwl. Toxicol. 2, 327 (1964).
`(135
`Liquid: pear-like odor. bp 213°. bpmz 134°. mp —51°.
`1.050.
`",3," 1.5232, n}; 1.499s. Flash pt. closed cup: 216°F
`(102°C). Practically insol in water. Misc with alcohol. ether.
`LDg“ orally in rats: 2490 mg/kg (Jenner).
`
`ingestion can cause G.l. irritation with vomiting and
`Caution:
`diarrhea. Also irritating to skin. eyes. respiratory tract.
`USE: 1n pcrl'umery. solvent for cellulose acetate and nitrate.
`
`[1011-51—61 Benzenemethanol: phen-
`1124. Benzyl Alcohol.
`ylcarbinol; phenylmcthanol; a-ltydroxytoluene. C7H80: mol wt
`108.14. C 77.75%.“ 7.46%. O 14.80%. C6115CH3011. Constit-
`uent ofjasmine. hyacinth. ylang-ylang oils. Peru and Tolu balsams.
`storax. where it occurs in ester form also. Originally prepd by the
`Canninaro reaction from benzaldehyde + KOH: Cannizmro. Amt.
`88. 129 (1853): if. Hickinhottom. Reactions ofOrgunit' Cont/Ids.
`(Longmans. London. 3rd ed.. 1957) p 251: A. l. Vogel. Practical
`Organic Chemistry (Longmans. London. 3rd ed.. 1959) p 71 l:
`Guttermann-Wieland. Pruxis (l(’.\' ()rganisr'hen C/tcmikcrs (de
`Gruyter. Berlin. 40111 cd.. 1961) p 193. Produced on a large scale
`by the action 01‘ sodium or potassium carbonate on benzyl chloride:
`DE 484662: Chem. Zenrrulhl. 1930. 1. 1052: Frrll. 16. 426: cf. Kirk-
`Orlmwr Encyclopedia of Chemical Technology vol. 3 (lntersciencc.
`New York. 1964) pp 442-449. Toxicity: Smyth er al.. Art-I1. Ind.
`Ilyg. Ot'c‘up. Mal. 4, 1 19 (1951).
`tli0 1.04535:
`Liquid. Faint aromatic odor. Sharp burning. taste.
`dis 1.04156. mp -15.19°. bp7m, 204.7": bp.“m 183.0"; bpzm,
`160.0°; bplm, 141.7”; hpm, 129.3°: hp“, ”9.8"; bpm 105.8°: bpl0
`926°: hp5 8(1.8°:bp,_.,58.()°.
`".3,“ 1.54035; ".1: 1.53837: Dreisbach.
`Martin. Ind. Eng. Chem. 41. 2875 (I941). Absorption spectrum:
`Brodc. J. Phys. Chem. 30. 61 (1926). Vapor density 3.72 (air =
`100). Flash pt. closed cup 213°F. open cup 220°F. Autoignition
`temp 817°F. One gram dissolves in about 25 tnl water. One
`volume dissolves in 1.5 vols oli5()% ethyl alcohol. Misc with abs
`and 94% alcohol. ether. chloroform. LD_..0 orally in rats: 3.1 g/kg
`(Smyth).
`USE: Manul~ other benzyl compds. Pharmaceutic aid (antimicro-
`bial). Solvent for gelatin. casein (when hot). solvent for cellulose
`acetate. shellac. Used in perfumery and in flavoring (mostly in form
`of its aliphatic esters).
`111 microscopy as embedding material.
`THERAP (.‘AT (VET): Has been used for relief froth pruritis.
`
`[100-46-91 Benzencmcthanamine:
`1125. Benzylaminc.
`aminotoluene: phenylmethylamine: moringinc. C7H.,N: mol wt
`107.15. C 78.46%, H 8.47%. N 13.07%.
`l’repn from benzyl-
`chloride and ammonia: Mason. J. Chem. Soc. 63. 131 1 (1893):
`by redn oi‘ benzonitrile: Carothers. Jones. J. Am. Chem. Soc. 47,
`3051 (1925): froth benzyl bromide + acetamide: Erikson. Ber. 59.
`2665 (1926): from N-bcnzylphthalimide + hydrazine hydrate:
`lng.
`Manske. J. Chem. Sm: 129, 2348 (1926). Identity with moringine:
`Chakravarti. Bull. Calcutta Sch. Trop. Med. 3, 162 (1955): CA. 50.
`1681911211956).
`
`NHZ
`
`Liquid:strong1y alkaline reaction. bp 185°: hpI2 90°.
`",2,0 1.5401. Miscible with water. alcohol. ether.
`Hydrochloride. C7 H.,N.HCI. Crystals, mp 253°.
`Hydroiodide. C7 H.,N.H1. Leaflets. mp 162°.
`Caution: Highly irritating to skin. mucous membranes.
`USE: 1n organic synthesis.
`
`(11" 0.983.
`
`[1()3~32-2] N»Phenylbettzenemclhan-
`1126. Benzylaniline.
`amine: N-phenylbenzylamine: hen/,ylphenylamine. CnHHN; mol
`wt 183.25. C 85.21%. H 7.15%. N 7.64%. Col-15CH3NHChl-ls.
`l’repn from benzyl ale and aniline in the presence of KOH: Sprin-
`zak. .I. Am. Chem. Sm. 78. 3207 (1956): from benzaldehydc and
`aniline in the presence 01" NaBHJ: SchellenhergJ. Org. Chem. 28,
`3259 (1963).
`Prisms. mp 37-38°. hp 306307". Practically insol in water: sol
`in alcohol. chloroform. ether.
`
`1127. Benzyl Benzoate. 1120—51—4] Benloic acid phenyl-
`methyl ester: benzoic acid benzyl ester: benzylbenzenecarboxylatc:
`Acarosan: Antiscabiosum: Ascabiol. CHHuOg: mol wt 212.24. C
`79.23%. H 5.70%. 0 15.08%. COHSCOOCHZChHS. Contained in
`
`Peru and 'l‘olu balsams. Prepd by t
`benzaldehyde: Kamm. Kamm. 0
`ed.. 1941): by the dry esteriiicatior
`chloride in the presence of triethylz
`Chem. 39., 1300 (1947). Toxicity
`Phurmut'ol. Exp. Tltcr. 84, 358 ( 1‘.
`H.171.
`'I'lu't‘. 93., 26 (1948). Compr
`Hassan. J. S. Mossa. Amt]. Profiles
`Leallets or oily liq: faint. pleasa
`taste. mp 21°.
`(155 1.118. bp 3;
`156°. Sparingly volatile with stea
`glycerol. Miscible with alc.ch1o1
`mice. rabbits. guinea pigs (g/kg):
`l
`Caution: Direct contact may
`symptoms of overexposure by in?
`gressivc incoordinalion. CNS exc1
`'l‘n.\'it‘ol()g_v of Cmrmtcrt'iul Prod
`(Williams & Wilkins. Baltimore. 5
`USE: As solvent of cellulose ac
`musk: substitute for camphor in
`compds: perl'ume fixative: in con
`V013.
`THERAPCAT: Scabicide. pcdicu
`THERAP (.‘A'l‘ (Vi-71‘): Acaricide.
`C1115.
`
`|
`1128. Benzyl Bromide.
`zene: a-bromotolucne: w-bromott
`C 49.16%. H 4.13%. Br 46.72%.
`I
`of bromine on toluene in ultravio
`57. 679 (1924); Zelinsky. DE 47
`1216: Frdl. 16. 335: by the actio
`Lachman. J. Am. Chem. Soc. 45., 2
`Lacrimatory liquid. mp —3.9
`1.43801d'7 1.443: (13" 1.3886. 510
`Catt/ion:
`lnlcnsely irritating 11
`Large doses cause CNS depressiot
`
`l
`1129. Benzyl Chloride.
`zcne:tx-chloroto|1.1ene. C7H7C
`5.57%. CI 28.01%. CbHsCHZCl
`of toluene: A. 1. Vogel. Pl‘ut'liCfl
`London. 3rd ed.. 1959) p 538: (
`()t'gdltls('ltt’ll Chcmikt'rs (de Gru:
`Manul': Faith. Kt’yl‘x & Clurk'si
`enheim. M. K. Moran. Eds. (Wile;
`1975) PP 145-148.
`Very refractive liquid: rather
`1.100. bp 179°. mp —-48 to —-‘
`Miscible with alcohol. chlorofom
`in the presence of iron.
`Caution: Potential symptoms
`eyes. skin and nose: weakness: ir
`pulmonary edema. See NIOSII P
`
`(DHHS/NIOSH 97—140. 1997) p I
`US Manul~ benzyl compds. p
`dyes. synthetic tannins. artificial n
`1130. Benzyl Cinnamate.
`noic acitl phenylmethyl ester: 11
`cinnamein.
`le-lHOZ: mol wt
`13.43%. C(,H5CH=CHCOOC
`Peru and Tolu balsams: Tschit
`(1894); Tschirch. ()berliindcr. il
`J. Am. Chem. Soc. 43, 1672 (192
`(1952): Bender. Zerner. ihid. 84.
`M. Jenner m (1].. Font] Cusnwt. 'l‘t
`Crystals from 95% ethanol: sv
`reported as mp 33-34° (Volw11-
`ordinary pressure: bpus 154—15
`Practically insol in water. prop)
`alc. ether. oils. LDSu orally in rat:
`USE: 1n artificial flavors. in per
`
`1131. Benzyl Cyanide.
`phenylacetonitrile: or-tolunitrile:
`
`[
`
`Page 186
`
`Consult the Name Index before using this section.
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