EXHIBIT 1011
`
`

`

`
`
`“WM"*Wfinm/WfiwA_
`
`EDITION
`
`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
`
`

`

`Library of Congress Catalog Card Number 89-6000]
`ISBN Number 0—9l [910-00-X
`ISBN Number 978~0—9l l9IO-00-I
`
`
`
`For more
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`pamon
`course of thl
`
`to publish ar
`scientific exr
`
`Each editi
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`again, signif
`cine, agricul'
`of the reseai
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`tionaI physic
`new tools fr
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`panded and
`ganic Name
`
`The Suppl
`of hard—to—fi
`sections. Ne‘
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`in the prever
`in this refere
`
`acronyms en
`
`An impor
`that accompz
`the scientist ‘
`and CD in t
`
`Finder® soft
`
`1000 monog
`available in ;
`
`Merck &
`Merck is con
`continues to
`
`not-for-profi'
`this edition I
`use it.
`
`Copyright © 2006 by MERCK & CO.. INC.. Whitehouse Station. NJ. USA
`
`All rights reserved. No part of this book or electronic product may be reproduced or used in any form or by any means.
`electronic or mechanical, including photocopying, or by any information storage and retrieval system. without permission
`in writing from the Publisher. Inquiries should be addressed to The Merck Index Editorial Offices, PO. Box 2000. Merck
`& Co., Inc.. Rahway, NJ 07065.
`
`Primed in the USA
`
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`

`

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`
`2441 (1981). Pharmacokinetics in lactating sows: N. Cort er al.,
`Am. J. Vet. Res. 42, 1804 (1981). Use in regulation of bovine labor:
`2. Veznik et (11., ibid. 40, 425 (1979). Effect on milk let-down in
`sows: N. Cort e101,. 117111.43, 1283 (1982).
`
`CH2
`CH2
`
`CH2
`
`1800
`Carbitol®
`[22232-54—8] 2.3-Dihydro-3-mcthyl-
`1798. Carbimazole.
`2-thioxo-IH-imidazole-l-carboxylic acid ethyl ester: l—elhoxycar-
`bonyl-3-mcthyl-2—thio-4-imidazoline: ethyl 3-methy1-2-thio-
`imidazoline-1-carboxy1ate:
`l-methyl-3-carbethoxy-2-thio—
`glyoxalone; athyromazole: Neo-mercazole; Neo-Thyreostat. C7-
`11.01512025; mol wt 186.23. C 45.15%. H 5.41%. N 15.04%. 0
`17.18%, S 17.22%. Thyroid inhibitor. Prepn: Rimington eral..
`US 2671088, reissued as US RE 24505: US 2815349 (1954. 1958.
`1957. all to Natl. Res. Dev. Corp); BakerJ. Chem. Soc. 1958. 2387.
`Clinical efficacy in Graves' disease: J. Duprey et (11.. Presse Med.
`17, 1124 (1988).
`
`0:10HN
`
`
`
`IIe—Gln—Asn—Cys—Pro—Leu—GIyNHg
`
`H360
`
`Solid from methanol with ether [01],) ~69.0° (c 0.25 in [M
`acetic acid).
`THERAP CAT (VET): Oxytocic. stimulates milk let-down.
`1796. Carbic Anhydride.
`[129-64-61 3aa.4.7.7aa-Tetrahy-
`dro-4a.7a-methanoisobenzofuran-1.3-dione: eix-endo—S-norbor-
`nene—2,3-dicarboxy1ic anhydride; endo-eis-bicyc1012.2.1lhept-S-
`ene-2,3-dicarboxylic anhydride: 3,6-end0-methylene—1.2.3.6-tetra—
`hydro-cis-phthalic anhydride; 3.6—endo-methylene-A‘4etrahydro—
`phthalic anhydride; nadic anhydride. CgHEOS; mol wt 164.16. C
`65.85%, H 4.91%. O 29.24%. Prepd by the reaction of maleic
`anhydride with cyclopentadiene in benzene: Diels. Alder, Ann. 460,
`98 (1928). Crystal structure: Destro et al.. Acta Crystallogr. 253,
`2465 (1969).
`O
`
`O
`
`Shiny. orthorhombic crystals from petr ether. mp 164-165“. d
`1.417. Converted to equilibrium mixtures with exa-cis isomers
`when heated above mp. Sol in benzene, toluene. acetone. carbon
`tetrachloride. chloroform. ethanol, ethyl acetate. Slightly sol in petr
`ether. Reacts with water to form the corresponding acid. Forms the
`y—lactone of 5-hydroxy-2,3-norcamphanedicarboxylic acid in 50%
`also...
`
`(aS)-a-Hydrazino-3.4-di-
`[28860.95-9]
`1797. Carbidopa.
`hydroxy-a-methylbenzencpropanoic acid monohydrate; (-)-L-a-
`hydrazino-3.4-dihydroxy-a-methylhydrocinnamic acid monohy—
`drate; a~hydrazino~u-methy1-[3—(3.4-dihydroxypheny1)propionic
`acid monohydrate; L—a—(3.4-dihydroxybenzy1)-ct-hydrazino-
`propionic acid monohydrate; a—methyldopahydrazine: HMD'. MK-
`486; Lodosyn. C,(,H.4N204.H20; mol wt 244.24. C 49.18%. H
`6.60%. N 1 1.47%. O 32.75%. Peripheral decarboxylase inhibitor.
`Prepn of DL-form: Pfister. FR M1553 (1962 to Merck & Co.). GA.
`59, 12921e (1963); Sletzinger et al.. J. Med. Chem. 6, 101 (1963);
`GB 940596; Chemerda et al.. US 3462536 (1963, 1969 both to
`Merck & Co.). Synthesis of the L-form: Karady er (11.. DE
`2062285: DE 2062332 (both 1971 to Merck & Co.). CA. 75,
`118122t. 118120r (1971); eidem. J. Org. Chem. 36, 1946. 1949
`(1971). Inhibition of dopa decarboxylase: Porter 2! al.. Biochem.
`Pharmacol. 11, 1067 (1962); Moran. Sourkes. J. Pharmacol. Exp.
`Ther. 148, 252 (1962); Watanabe et al.. Clin. Pharmacol. leer. 1],
`740 (1970). Only the L-form is pharmacologically active: Lotti.
`Porter. J. Pharmacol. Exp. Ther. 172, 406 (1970).
`H0
`COOH
`
`H30 HN—NH:
`
`. H20
`
`HO
`
`Crystals from hot water. mp 203-205° (dec). [ado ~17.3° (meth-
`anol). Also reported as mp 208°.
`Combination with levodopa.
`com; Nacom; Sinemet.
`DL-Form. Tan fluffy crystals. mp 206-208“ (dec). uv max
`(methanol): 282.5 nm (e 2940).
`THERAP CAT: In combination with levodopa as antiparkinsonian.
`
`[57308-51 ~71 Co-careldopa; Isi-
`
`N
`N
`0
`CH
`H3C/ \n/ \n/ V 3
`s
`0
`
`Crystalline powder with characteristic odor; tasteless at first.
`followed by bitter taste: mp 122—125°. Sol (at 20°) in 500 parts
`of water; in 50 parts of ethanol; in 330 parts of ether; in 3 pans of
`chloroform: in 17 parts of acetone. uv max in 0.1N HCI : water
`(1:8): 291 nm; in 0.1N H2804: 227 nm and 291 nm(E12‘m 557).
`THERAP CAT: Antihypenhyroid.
`
`[486-168] 2-[(4—Chlomphenyl)-2-
`1799. Carbinoxamine.
`pyridinylmethoxy|-N,N-dimethylethanamine; 2-[p-chloro-a-(2-di-
`methylaminoethoxy)benzyl]pyridine; paracarbinoxamine. Cme-
`ClNzO; mol wt 290.79. C 66.09%. H 6.59%. C1 12.19%. N 9.63%.
`O 5.50%. Prepn: Tiiford. Shelton. US 2606195 (1952 to Wm. S.
`Merrell): Swain. US 2800485 (1957 to McNeil Labs). Prepn of [-
`form: GB 905993 (1962 to McNeil Labs). C.A. 58. 56443 (1962).
`Abs config of l—forrn: V. Barouh er al.. J. Med. Chem. 14, 834
`(1971). Pharmacology and toxicology: R. Cahen. Ann. Pharm. Fr.
`20, 463 (1962). GLC determn in serum: D. J. Hoffman et a1.,J.
`Pharm. Sci. 72, 1342 (1983).
`
`CH3
`1N
`o/\/ \CHa
`N
`l\/
`
`CI
`
`Liquid, bpm 158<162°.
`Hydrochloride. CmngClNZOHCl. Crystals from isopropa-
`nol + ethyl acetate. dec 162—164". 801 in water.
`Maleate.
`[3505—38-2] Allergefon; Clistin; Ciberon: Lergefin;
`Polistin T—Caps. CmngC1N20.C4H4O4: mol wt 406.86. Bitter
`crystals from ethyl acetate. mp 1 17-119°. Freely sol in water.
`alcohol. chloroform. Very slightly sol in ether. pH of 1% aq
`soln 4.6~5.1. LDSO in mice (mg/kg): 166 i.p. (Cahen).
`l-Form. Levocarbinoxamine'. rotoxamine: McN-R—73-Z. bpotfi
`143—144°. "5° 1.5522. [aiff —6.8° (c 2 in methanol).
`l—Form d—tartrate.
`[49746-00—1] Twiston. C16HI9C1N20.C4-
`H606: mol wt 440.87. Crystals from isopropanol. mp 1434445".
`[c1173s +37.2° (c 20 in methanol).
`THERAP CAT: Antihistaminic.
`
`[111.90-0] 2-(2-Ethoxyethoxy)ethanol:
`1800. Carbitol®.
`diethylene glycol monoethyl ether; ethyl digol. CGHE403; mol wt
`134.17. C 53.71%. H 10.52%. 0 35.77%. CHSCHZOCH1CH2—
`OCHZCHZOH. Prepn from ethylene oxide and 2—ethoxyethanol in
`the presence of S01: Britton, Sexton. US 2807651 (1957 to Dow).
`Toxicity data: Smyth. Carpenter. J. Ind. Hyg. Toxicol. 30, 63
`(1948).
`«135 0.9855. dgg 1.0273. ng’
`Very hygroscopic liquid. bp 196°.
`1.4273. Flash pt 96°C (Tag open cup). Miscible with acetone,
`benzene. chloroform, ethanol. ether. pyridine. etc: Jackson. Drury.
`Ind. Eng. Chem. 51. 1491 (1959). Also miscible with water. LDso
`orally in rats: 8.69 g/kg (Smyth. Carpenter).
`c133 1.0114.
`Acetate. CXH1604. Liquid. hp 2185". mp —25°.
`n%," 1.4213. Flash pt 110°C (Tag open cup). Miscible with water.
`alc. ether. most oils. LD50 orally in rats:
`1 1 g/kg (Smyth. Carpen-
`ter).
`
`Consult the Name Index before using this section.
`
`Page 291
`
`rngen succinate: 3-0-(fl-car-
`Z—en-3()-oic acid;
`l8B—glycyr~
`bcnoxalonc. Cul'15007: mol
`19.62%. Anti-inflammatory
`,q.1'. Prepn: Gottfried. Bax-
`960. 1961 to Biorex). Mono-
`Robson. F. M. Sullivan. Eds.
`pp. Symposium on clinical
`15. Suppl. 65. 1-121 ([980).
`1 in humans: J. Rask-Madsen
`'83): P. Minuz e! (11.. Pharma-
`‘omprchensive description]: S.
`by. (item. 24. 1-43 (1996).
`H3Q
`COOH
`
`
`
`[04.3,” +128” (chloroform).
`1°.
`lex: Bioral: Ncogel; Snnodin:
`:1 wt 614.72. Creamy—while
`n chloroform. other. pKa,
`26(1nm (E113 172). 1-11.0111
`; in male rats (mg/kg): 3200
`
`l-Phenylcyclopcntane-
`1-6]
`‘xy)ethyl ester. 2-(diethylami-
`tanecarboxylate; 2—(dicthy1-
`tyl- | -carboxylate: l-phenyl-
`hylaminocthoxyethyl ester:
`13, N03: mol wt 333.47. C
`9%. Prcpn: 11. G. Morrcn.
`., 1958 both to Union Chimi-
`). Wellens. Arzneim.vF0r.\‘('It.
`1g function: E. Krieger. ihid.
`
`3
`
`\/\N/\CH
`kCH3
`
`r: Antces: Calnathal: Carbo-
`:ct: Pcncal: Sedotussin: To-
`)3.C,,HK()7Z mol wt 525.59.
`.chloroform; sol in alcohol.
`£01 in ether. petr ether. bcnv
`
`l-Butanoic acid-2-(0—
`.1]
`-butyric acid-2-[3-( p-meth~
`nino-Z-O-metltyltyrosinc— 1 -
`:ntaazacycloeicosane cyclic
`'ba-[2-tyr(OMe) I-OT: (2—0-
`)cin: d(COMOT): DCCOmO'
`)1 wt 988.16. C 54.70%. H
`. Synthetic carhacanalog of
`leer. Czech. Chem. Commun.
`2 2732175 (1976 to Czech.
`pcrties: M. Lebl. Collect.
`:0). Utcrotonic and galacto-
`145: T. Barth el al.. ihid. 46.
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