Proceeding
`Party
`
`Correspondence
`Address
`
`Submission
`Filer's Name
`Filer's e-mail
`
`Signature
`Date
`Attachments
`
`Trademark Trial and Appeal Board Electronic Filing System. http://estta.uspto.gov
`ESTTA514950
`ESTTA Tracking number:
`01/08/2013
`
`Filing date:
`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`BEFORE THE TRADEMARK TRIAL AND APPEAL BOARD
`92047741
`Defendant
`Belmora LLC
`MARSHA G GENTNER
`JACOBSON HOLMAN PLLC
`400 7TH ST NW, 6TH FLOOR
`WASHINGTON, DC 20004
`UNITED STATES
`trademark@jhip.com, mgentner@jhip.com, lweiss@jhip.com
`Testimony For Defendant
`Philip L. O'Neill
`poneill@jhip.com, mgentner@jhip.com, cchapman@jhip.com,
`trademark@jhip.com
`/Philip L. O'Neill/
`01/08/2013
`England Exhibit 5.pdf ( 3 pages )(1309358 bytes )
`England Exhibit 6.pdf ( 3 pages )(1215551 bytes )
`England Exhibit 7.pdf ( 5 pages )(311121 bytes )
`England Exhibit 8.pdf ( 14 pages )(1196139 bytes )
`England Exhibit 9.pdf ( 2 pages )(942189 bytes )
`
`

`
`TTAB Cancellation No. 92047741
`Belmora Notice of Reliance
`
`EXHIBIT B1
`
`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`
`England Deposition Exhibit No. 5 (Belmora LLC exhibit)
`
`Page 1 of 3
`
`

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`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`
`England Deposition Exhibit No. 5 (Belmora LLC exhibit)
`
`Page 2 of 3
`
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`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`
`England Deposi ion Exhi
`
`it No. 5 (Belmora LLC exhi
`
`it)
`
`Page 3 of 3
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`

`
`TTAB Cancellation No. 92047741
`Belmora Notice of Reliance
`
`EXHIBIT B2
`
`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`
`England Deposition Exhibit No. 6 (Belmora LLC exhibit)
`
`Page 1 of 3
`
`

`
`FLANAX
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`PAIN RELIEVER
`
`FEVER REDUCER
`
`’ HEADACHE ‘ BACKACHE
`' ARTHRITIS ' FEVER
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`' COMMON COLD
`
`NM 27554 10.1 04
`
`(9 FLANAX
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`PAIN RELIEVER
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`SODIUM USP (NSAIIJI
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`
`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`
`England Deposition Exhibit No. 6 (Belmora LLC exhibit)
`
`Page 2 of 3
`
`

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`
`Bayer Consumer Care AG v. Belmora LLC
`TTAB Cancellation No. 92047741
`England Deposition Exhibit No. 6 (Belmora LLC exhibit)
`
`Page 3 of 3
`
`

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`
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`__,»c..--'...._'_‘_...._...__)-G.?__‘.__..44.<__._J,
`
`
`
`THE
`
`MERCKINDEX
`
`AN ENCYCLOPEDIA OF
`
`CHEMICALS, DRUGS, AND BIOIOGICALS .
`
`TWELFTH_ EDITION
`
`Susan Budavari, Editor
`Maxyadele J. O’Nei1, Senior Associate Editor
`Ann Smith, Associate Editor
`Patricia E. Heckelman, Assistant Editor
`Joanne F. Kinneary, Assistant Editor
`
`Published by
`Merck Research Laboratories
`
`Division of
`MERCK & CO., INC.
`
`_
`
`Whitehouse Station, NJ
`
`EXHIBIT
`WIT:
`DATE:i
`REPORTER:
`
`. H RMONSON
`
`I
`
`Bayer v Belmora
`Cancellauon No. 92047741
`Petitioner's Exhibit
`
`'
`
`BAY 000136
`
`

`
`
`
`I
`
`I
`
`
`
`THE
`
`MERCKINDEX
`
`AN ENCYCLOPEDIA op
`
`CHEMICALS, DRUGS, AND BIOLOGICALS '
`
`TWELFI‘H_ EDITION
`
`Susan Budavari, Editor
`Maryadele J. O’Neil, Senior Associate Editor
`Ann Smith, Associate Editor
`Patricia E. Heckelman, Assistant Editor
`Joanne F. Kjnneaxy, Assistant Editor
`
`Published by
`Merck Research Laboratories
`
`Division of
`
`MERCK & CO., INC.
`
`Whitehouse Station, NJ
`
`1996
`
`'
`
`BAY 000137
`
`

`
`
`
`MERCK & CO., INC;
`Whitehouse Station, N .J.
`U.S.A.
`
`
`
`lst Edition-1889
`2nd Edition—1896
`3rd Editi0n—-—1907
`4th Edition-1930
`Sth Edition——1940
`6th Edition——1952
`7th Edition~—196O
`8th Edition-——1968
`9th Edition——1976
`10th Edition~—1983
`11th Edition——~l989
`
`Library of Congress Catalog
`Card Number 89-60001
`ISBN Number 0911910-12-3
`
`Copyright © 1996 by MERCK & CO., INC.
`All rights reserved. Copyright under the Universal Copyright Convention
`and the International Copyright Convention.
`Copyright reserved under the Pan-American Copyright Convention.
`
`Printed in the U.S.A.
`
`BAY 000138
`
`

`
`Firemaster LV~T 231’ [Michigan
`Chem.] see 9881
`Firemaster T 23P [Michigan Chem.)
`see 9881
`Firmacef [Firma] see 1967
`Firon [Beard] see 4094
`Fir—wood Oil see 6936
`-
`Fisalamine see 5964
`Fischer's Yellow see 2493
`Fisetin, 4129
`Fish-berry see 2518
`~
`Fish Glue see 5123
`Fisidenolon 1521 see 4129
`Fisiobil [S.A.L.V.A.T.] see 3248
`Fisiodar [Gcntili] see 3003
`Fisostina see 4334
`Fivent [Fisophanna] see 2658
`-FK-027 see 1975
`FK-176 see 10052
`FK-235 see 6637
`FK-435 see 3502
`FK-482 see 1971
`. FTC-506 see 9200
`FK-749 see 2000
`FK-1160 see 9564
`FL-113 see 5090
`FL-10.39 see 409
`FL-1060 see 408
`FLA-731 see 8301
`Flabelline see 6047
`Flagecidin [Pfizer] ree 708
`Flagentyl [Rhone-Poulenc] see 8562
`Flagyl [Sear1e] see 6242
`Flagyl I.V [SCS] see 6242
`'
`Flake Lead see 1034 ‘
`Flamasone [Norbrook] see 7901
`Flamazine [Smith & Nephew] see 9071
`Flamitajin [Teisan; Iwalci] see 4131
`Flammazine [Duphar] see 9071
`Flammex AP see 9881
`Flammex T 231’ see 9881
`Flanax [Syntex] see 6504
`Flanin F [Tokyo Tanabe] see 4131
`Flantadin [Lcpetit] see 2916
`Flatistine [Sanofi] see 1898
`Flavacidin see 658
`.
`Flavan [Pharmafarm] see 5477
`- 3,3’,4,4’,5,7-Flavanhexol see 5477
`3,3’,4’,5,7-Flavanpentol see 1950
`Flavaspidic Acid, 4130
`Flavaxin [Winthrop] see 8367
`Flavicin see 658
`Flavine-Adenine Dinucleotide, 41 3 1
`Flavine Yellow Shade see 8219
`Flavin Mononucleotide see 8368
`Flavitan see 4131
`Flavomycin [Hoechst] see 979'
`Flavone, 4132
`7-Flavone Ethyl Hydroxyacetate see
`3565
`7-Flavonoxyacetic Acid Ethyl Ester '
`see 3565
`Flavopereirine, 4133
`Flavophospholipol see 979
`Flavoquine [Rousse1-UCLAF] see 609
`Flavoxanthln, 4134
`Flavoxate, 4135
`Flavurol see 5914
`Flaxedil [Lcder1e; Davis &; Geck] see
`4361.
`Flaxseegl see 5532
`FLC-1374 see 9561
`Fleabane see 3708
`Flea Seed se_e 7674
`Flebopex [Profarma] see 3350
`Flebosan [Dukron] see 9738
`Flebosmil [Bonchara] see 3350
`ebosten [Bonomelli] see 3350
`meboaopin [Bago] see 3350
`Flecainide, 4136
`
`Flectadol [Maggioni] see 5668
`Flectar see 10205
`Flectron [Shell] _see 2836
`Fleishmilchsiiure see 5350
`Flemoxin [Paines & Byrne] see 617
`Fleroxacin, 4137
`Flesinoxan, 4138
`Flexal see 1889
`Flexartal [Clin-Comar-Byla] see 1889
`Flexazone see 7431
`Flexeril [Merck & Co.] see 2782
`Flexiban [Merck & Co.] see 2782
`Flexible Collodion see 2547
`Flexidol [Daker-Farmasimes] see 4052
`Flexidor [Elanco] see 5256
`Flexilon [McNeil] see 10328
`Flexin [McNeil] see 10328
`Fllndersine, 4139
`Flindix [Lusofarmaco] see 5245
`Flint ree 8637
`Flivas [Asahi] see 6443
`Flixonase [Allen & Hanburys] see
`4244
`
`Flixotide [Glaxo] see 4244
`Flobacin [Sigmatau] see 6865
`Flo-Cillin Aqueous [Bristol] see 7226
`Flociprin [1131] see 2374
`Floctafenine, 4140
`Flodil [Astra] see 3991
`Floganol [Zyma] see 2419
`Flogar [UCB] see 7048
`Flogencyl [Parke-Davis] see 3737
`Flogene [Polifarma] see "4045
`Floginax [Lifepharma] see 6504
`. Flogitolo see 7106
`Flogobene [Farge] see 7661
`Flogobron [Intersint] see 7078
`Flogoril see 7106
`Flogos [Gentili] see 9185
`Flogovital [Bago] see 6640
`Flogozen [SPA] see 4949
`Floionic Acid see 7478
`Flolan [VVel1come] see 8061
`Flomax [Chiesi] see 6620
`Flomoxef, 4141
`‘
`Flonatril [Specia] ieé 2466
`Flopion [Kyoritsu] see 4142
`Flopropione, 4142
`Florantyrone, 4143
`Floraquin [Sear1e] see 5063
`Floredil, 4144
`Flore! [Union Carbide] see 3777
`Flores Martis see 4061
`Florfenicol, 4145
`Florid [Mochida] see 6266
`Floridin see 4306
`Floridin [Coll] see 2025
`Florimycin see 10139
`Florinef [Squibb] see 4166
`Floripavine see 8493
`Florisil see 5727
`Flormidal [Galenika] see 6270
`Florocid see 8762
`Florone [Upjohn] see 3186
`Floropipamide see 7608
`Floropryl [Merck & Co.] see 5192
`Flosequinan, 4146
`Flosequinon see 4146
`Flosin [Erba] see 4999
`Flosint [Erba] see 4999
`Flou [ELEA] see 8090
`Flovacil [Andromaco] see 3190
`Flovent [Glaxo] "see 4244
`Flowering Dogwood see 2599
`Flowers of Antimony see 752
`Flowers of Tin see 8933
`Flowers of Zinc see 10279
`Flowerydieaded Spurge see 3949
`Floxacillin, 4147
`.
`Floxacin [Merck & Co.] see 6793
`
`Name Indet
`
`V.E
`
`-
`
`Floxapen [Beecham] see 4147
`Floxicam [Menarini] see 5258
`Floxil [Cilag] see 6865
`Floxin [J & I] see 6865
`Floxuridine, 4148
`Floxyfral [So1vay] see 4251
`Fluacizine, 4149
`Fluanisone, 4150
`Fluanxol [Lundbcck] see 4224
`Fluanxol Dé-pot [Lundbeck] see 4224
`Fluaton [Tubi Lux] see 4213
`Fluatox [Inpharzam] see 89
`Fluazacort, 4151
`Fluazifop-butyl, 4152
`Fluazinam, 4153
`Flubendazole, 4154
`Flubenisolone see 1226-
`Flubenol [Janssen] see 4154
`Flubenzimine, 4155
`Flubron [SS Phann] see 4248
`Flubuperone see 5870 .
`Flucam [Pfizer] see 629
`Fluchloralin, 4156
`Flucinom [Schering] see 4242
`Fluclorolone Acetonide see 4157
`Flucloronide, 4157
`Flucloxacillin see 4147.
`Fluconazole, 4158
`Flucort [Syntex] see 4173
`Fluctin [Lilly] see 4222
`Flucycloxuron, 4159
`Flucythrinate, 4160
`Flucytosine, 4161
`Fludara [Triton] see 4162
`Fludarabine, 4162
`Fludarene [Merck & Co.] see 2294
`Fludemil see 4174
`Fludeoxyglucose F“, 4163
`Fluderma [Farrnitalia] see 4270
`Fludestrin [Bristol] see 9321
`Fludex [Biopharma] see 4969
`Fludiazepam, 4164
`Fludilat [Thiemann] seé 1060
`Fludioxonil, 4165
`Fludrocortisone, 4166
`Fludroxycortide see 4232
`Fluellite see 351
`Flufenamic Acid, 4167
`Flugeral [ltalfarmaco] see 4179
`Flugestone Acetate see 4235
`Fluibil [Zambon] see 2096
`Fluibron [Chiesi] see 401
`Fluidane see 1414
`Fluiden [Lafare] see 4041
`Fluidil [Adria] see 2822
`Fluifort [Dompé] "see 1850
`Fluimucetin [Inphariam] see 89
`Fluimucil [Zambon] see 89
`Fluindione, 4168'
`Fluindostatin see 4250
`Fluitran [Shionogi] see 9754
`Fluixol [Ripari-Gero] see 401
`Flukanide [Merck & Co.] see 8280
`Flukiver [Janssen] see 2473
`’
`Flumadine [Roche] see 8390
`Flumarin [Shionogi] see 4141
`Flumark [Dainippon] see‘ 3625
`Flumax [Shionogi] see 1969
`Flumazenil, 4169
`'
`Flumazepil see 4169
`-
`Flumecinol, 4170
`Fltunedroxone Acetate,‘ 417 1
`Flumen see 2221
`Flumequine, 4172
`Flumesil see 1064
`Flumethasone, 4173
`-
`Flumethiazide, 4174
`Flumetholon [Santen] see 4213
`Flumethrin, 4175
`-
`Flumetramide, 4176
`
`BAY 00139
`
`NI-1'71
`
`
`
`

`
`~
`
`HI. Wu et a1.. Weed Sci. 23, 54 (1975). Toxicity study: T.
`{awada et aI., Niigata Igakkai Zosshi 87, 289 (1973). CA.
`:0, 5625711 (1974).
`
`
`
`Narbomycin
`
`6507
`
`CH
`
`CH3
`l/
`3
`O/i}rN\/CH3
`O O
`
`Light brown solid from n-pentane, mp 63-64“ (tech,
`9.5‘’). Solubility in water at 20°:
`70 ppm. LD5o in mice
`g"/kg): > 5 orally, >1 i.p., > 1 s.c. (Kawada).
`USE: Herbicide.
`
`
`
`Consult the Name Index before usingthis .section.= ‘
`
`Page 1-101
`
`BAY 000140
`
`FxIn:
`
`” OCOOH
`
`.
`
`Crystals from ethanol, d§° 1.40. mp 203'’ (technical grade,
`mp 175-180“). Soly: <0.02 g/100 ml of water. Sol in alka-
`line solns. but dec above pH 9.5. Slightly sol in ethanol.
`acetone. benzene. Hydrolyzed by strong acids and bases.
`Sodium salt. C,8H12NNaO3, ACP-332, NPA-3, Alanap.
`USE: Herbicide; as analytical reagent for thorium and
`zirconium.
`
`(4S)-4-Methylsalinomycin; narasin A;
`6506. Narasin.
`Compd 79891; Antibiotic A-28086 factor A; C-7819B;
`Monteban. C‘3H.,zOn; mol wt 765.04. C 67.51%, H 9.49%.
`O 23.00%. Main component of a polyether antibiotic com-
`plex produced by Streptomyces aureofaciens NRRL 5758 &
`NRRL 8092. Production: D. H. Berg et al., Ger. pat. 2,-
`525,095 corresp to U.S. pat. 4,038,384 (1975, 1977 to Lilly);
`L. D. Boeck et al., Dev. Ind. Microbial. 18, 471 (1976).
`lsoln
`and characterization: D. H. Berg’, R. L. Hamill, J. Antibiot.
`31,
`I (1978). Biosynthetie studies using ‘-"C—NMR study:
`D. E. Dorman et al., Helv. Chim. Acta 59, 2625 (1976).
`Structure:
`J. L. Occolowitz et aI.. Biomed. Mass. Spectrum.
`3, 272 (1976); H. Seto et al., J; Antibiot. 30, 530 (1977).
`Anticoccidial activity: M. D. Ruff et aI., Poultry Sci. 59,
`2008 (1980). Total synthesis: Y. Kishi er al, Front. Chem.,
`Plenary Keynote Lect. IUPAC Congr., 28th 1981, K. I. Laid-
`ler. Ed. (Pergamon, Oxford. 1982) pp 287-304. HPLC de-
`termn in animal feeds: M. R. LaPointe, H. Cohen, J. Assoc.
`Offic. Anal. Chem. 71, 480 (1988).
`
`
`
`Crystals from acetone-water, mp 98-100"; resolidif and re-
`melts at 198-200'. uv max (ethanol): 285 nrn (e 58).
`[a]§§
`~54’ (c = 0.2 in methanol). pKa 7.9 (80% aq DMF). So_l
`in alcohols, acetone, DMF, DMSO. benzene. chloroform,
`ethyl acetate.
`Insol
`in water.
`LDSO i.p.
`in mice:
`7.15
`mg/ kg (Berg).
`'
`THERAP CAT (VET): Coccidiostat; growth stimulant.
`6507. Narbomycin.
`12-Deoxypicromycin. Cal-I,7NO.,;
`mol wt 509.68. C 65.98%. H 9.29%. N 2.75%. O 21.97%.
`Antibiotic substance produced by Streptomyces narbonensis
`from soil near Cannes, France: Corbaz et al.. Helv. Chim.
`Acta 38, 935 (1955). Structure: Prelog et aI.,
`ibid. 45, 4
`(1962). Stereochemical studies: Riclcards, Smith, Tetrahe-
`dron Letters l970, 1025; H. Ogura et al., J. Am. Chem. Soc.
`97, 1930 (1975); eidem. Tetrahedron 37, Suppl.
`1. 165
`(1981).
`lsoln and structure of the aglycone narbonolide:
`Hori et al.. Chem Commun. 1971, 304. Synthesis of nar-
`bonolide: T. Kaiho et al.. J. Org. Chem. 47, 1612 (1982).
`
`N"'CHa
`
`/CH3
`
`H3C\
`
`Crystals from ether -1- petr etherrrnp 113.5-115". "=:[§;]7-0
`+68.5° (c =-== 1.35 in.chloroform).‘. uv.r'nax’ (ab’s'~ethano'l)l1
`
`'-
`
`6504. Naproxen.
`(S)-6-Methoxy—a —methyl-2-naphtha-
`rneacetic acid; d-2-(6-methoxy-2—naphthyl)propionic acid;
`INPA; RS—3540; Bony]; Diocodal; Dysmenalgit; Equi-
`roxen; Floginax; Laraflex; Laser; Naixan; Napren; Napri-
`m; Naprius; Naprosyn; Naprosyne; Naprux; Naxen; Nyco-
`ren; Pranoxen; Prexan; Proxen; Proxine; Reuxen; Veradol;
`fenar. C,4H,,O3; mol wt 230.26. C 73.03%, H 6.13%. O
`3.84%. Nonsteroidal anti-inflammatory.
`Prepn:
`J. H.
`ried, I. T. Harrison, S. Afr. pat. 67 07,597; eidem, U.S.
`it. 3,904,682; eidem, U.S. pat. 4,009,197 (1968. l975. 1977
`I to Syntex); I. T. Harrison et al., J. Med. Chem. 13, 203
`970). Pharmacology: Roszkowski et al., J. Pharmacol.
`xp. Ther. 179, 114 (1971). Activity may be due to the
`>i1ity to inhibit prostaglandin biosynthesis. Mode of ac-
`Jn studies: Tornlinson et aI., Biochem. Biophys. Res Com-
`un. 46, 552 (1972). Metabolism: Runkel et al., J. Pharm.
`:1’. 61, 703 (1972). HPLC determn in plasma and serum:
`J. Streete, J. Chromatog. 495, 179 (1989). Stereoselective
`nthesis: K. T. Wan. M. E. Davis, Nature 370, 449 (1994).
`.inical studies: Katona et al., Clin. Trials J. 8, 3 (1972);
`unkel. Chem. Pharm. Bull. 20, 1457 (1972). Review: An!-
`-imittel-Forsch. 25, 278-332 (1975). Review of pharmacol-
`:y and therapeutic efficacy: R. N. Brogden et aL. Drugs
`1, 241-277 (1979). Comprehensive description: F. J. A!-
`zammary et aI., Anal. Profiles Drug Subs. Excip. 21, 345-
`3.0992).
`
`‘?”s
`
`60 COOH
`
`H300
`
`[oz]D +66‘ (in
`Crystals from acetone-hexane. mp 152-154'.
`oroform). Sol in 25 parts ethanol (96%), 20 parts meth-
`. 15 parts chloroform, 40 parts ether. Practically insol
`water.
`LDSO in mice (mg/kg): 435 i.v.; 1234 orally; in
`8 (mg/kg): 575 i.p.; 534 orally (Roszkowski).
`’iperazine salt, (C,,,HuO3)2.C,HmN2, piproxen, Numidan.
`30dium salt. C"H,3NaO_.,. RS-3650, Aleve, Anaprox,
`ranax, Axer Alfa, Flanax, Gynestrel, Miranax, Primeral,
`‘flex. Crystals from acetone. mp 244-246°.
`[aln - 11° (in
`thanol).
`‘HERA? CAT: Anti-inflammatory; analgesic; antipyretic.
`‘HERA? cm“ (VET): Anti-inflammatory.
`6505. Naptalam.
`2-[(1-Naphthalenylamino)carbonyl]
`zzoic acid; N-I-naphthylphthalamic acid; a-naphthyl-
`Ihalamic acid. C,,H,3NO3; mol wt 291.31. C 74.22%, H
`0%. N 4.81%, O 16.48%. Selective pre-emergence herbi-
`_=. Prepn: A. E. Smith, 0. L. Hoffmann. U.S. pat. 2,-
`5555 (1951 to US. Rubber). Activity: 0. L. Hoffmann.
`E. Smith, Science 109, 588 (1949). Mobility in soil: A.
`Smith et al., J. Agr. Food Chem. 5, 748 (1957).
`
`

`
`
`
`THE
`
`MERCK INDEX
`
`AN ENCYCLOPEDIA OF
`
`CHEMICALS, DRUGS, AND BIOLOGICALS
`
`
`
`EXH|B|Tfi
`wn:
`44,2:
`DATE:~/SQ /
`’
`REPORTER: J. HARMONSON
`
`
`
`BAY 000141
`
`THIRTEENTH EDITION
`
`Editorial Staff
`
`Maryadele J. O’Neil, Senior Editor
`
`Ann Smith, Senior Associate Editor
`
`Patricia E. Heckelman, Associate Editor
`
`John R. Obenchain Ir., Editorial Assistant
`
`Jo Ann R. Gallipeau, Technical Assistant
`
`Mary Ann D’Arecca, Administrative Associate
`
`Susan Budavari, Editor Emeritus
`
`Published by
`Merck Research Laboratories
`
`Division of
`
`MERCK & CO., INC.
`Whitehouse Station, NJ '
`
`200 1
`
`

`
`MERCK & CO., INC-
`Whitehouse Station, NJ ‘
`USA
`
`
`
`lst Edition—~1889
`2nd Edition——— 1896
`3rd Edition—-1907
`4th Edition--1930
`5th Edition-—1940
`6th Edition—— 1952
`7th Edition—~ 1960
`8th Edition——— 1968
`9th Editio‘n—~ 1976
`10th Edition—— 1983
`11th Edition— 1989
`12th Edition——~ 1996
`
`Library of Congress Catalog
`Card Number 89~60001
`
`ISBN Number 0911910-13~l
`
`Copyright © 2001 by MERCK & CO., INC.
`All rights reserved. Copyright under the Universal Copyright Convention
`and the International Copyright Convention.
`Copyright reserved under the Pan~American Copyright Convention.
`
`BAY 000142
`
`

`
`lishing a concise, authoritative reference work designed primarily to serve the
`needs of chemists, biochemists, pharmacists and those in related professions.
`The information is assembled with today’s need for quick reference in mind,
`but the commitment to excellence in scientific scholarship and to enhancing
`scientific communication remains paramount.
`This edition contains a diverse collection of over 10,000 monographs. More
`than 4,000 monographs are devoted to a wide variety of drugs and pharrnaceu-
`ticals, over 2,000 describe common organic chemicals and laboratory reagents,
`and another 2,000 cover naturally occurring substances and plants. An addi-
`tional 1,000 monographs focus on the elements and on inorganic chemicals.
`Almost 1,000 pertain to compounds of agricultural significance, and several
`hundred describe endogenous substances and biological agents.
`A number of changes have been made since the Twelfth Edition. The mono-
`graph section has been extensively revised and updated. In response to requests
`from our readership, the Chemical Abstracts Registry Numbers for title and
`derivative compounds have been embedded within the monographs. The deriv-
`ative compound data presentation now mirrors the title compound such that
`registry numbers, molecular weights and literature references are included in
`addition to names and physical properties as in previous editions. Patent data
`has been reformatted using the two letter international country codes. The sec-
`'tion on Organic Name Reactions has been updated and revised; further, the
`schema have been standardized. The Miscellaneous Table section has been
`redesigned andreordered to enhance access to the ancillary monograph infor-
`mation.
`'
`To facilitate the use of the information in the electronic age, The Merck
`Index will be expanding its electronic offerings from THE MERCK INDEX ON-
`LINESM, and THE MERCK INDEX on CD-ROM to include a Web—accessible format.
`The latter two formats will be both text and structure searchable. Additionally,
`information that we are unable to maintain in print due tosize restrictions will
`appear as part. of the electronic versions.
`Changes in size, scope and publishing mechanisms have been made with
`each edition to keep pace with the progress in science and information tech-
`_ nologies in order to accommodate the diverse interests of an ever—broadening
`and sophisticated readership. In this environment, it is especially gratifying that
`- so many still refer to The Merck Index on a daily basis. We hope that this
`edition, published by Merck & Co., Inc., as a service to the scientific community
`and the public, will prove to be a valuable resource to all.
`'
`
`V
`
`BAY 000143
`
`

`
`EXPLANATORY NOTES
`
`The Thirteenth editionpof The Merck Index contains 10,250 monographs
`describing significant chemicals, drugs, and biological substances. The entries
`are not a listing of Merck & C0,, Inc. products, but rather cover a wide range
`of compounds, which have been selected on the basis of present or historic ‘
`importance and interest. Since the publication of the Twelfth Edition in 1996,
`over 5,000 monographs have been significantly revised and updated, while
`several hundred monographs have either been condensed or deleted from the
`manuscript to make room for hundreds of new monographs.
`Entries are generally limited to single substances and related compounds
`(isomers, salts, etc.). While multi-component drugs are, for the most part, ex-
`cluded, there are a number of monographs devoted to families of natural prod-
`ucts or biological substances. Monographs vary greatly in length. The length
`of a monograph, however, is not necessarily indicative. of the importance of a
`compound, but rather may simply be an indication of the amount of relevant
`published information available for the compound.‘
`For the purpose of illustrating the general monograph format, a typical mono-
`graph is depicted and the components are identified. While all possible cate-
`gories of information in a monograph are described below, it must be empha-
`sized that not all categories are present in every monograph.
`Monograph Number. Sequential accession numbers are assigned to mono-
`graphs which are alphabetized by title. Entries in the indices are referenced to
`these accession numbers, not to page numbers. (Note: Monograph numbers. in
`the Thirteenth Edition do not correspond to Twelfth Edition monograph num-
`bers.)
`Monograph Title. Titles are usually generic (United States Adopted
`Names——-USAN——or
`International Nonproprietary Names——~INN———in the
`case of drugs), trivial, or simple chemical names. Trademarks, designated by
`®, are used for a small number of entry titles, primarily when nonproprietar
`terms are not available.
`
`Chemical Abstracts Registry Number(s). The Chemical Abstracts Service
`(CAS) Registry Number appears following the title. These unique identifiers
`are provided for title substances and for selected derivatives; where appropriate,
`numbers for isomeric and unspecified forms of the compound are listed. CAS
`Registry Numbers and CAS Index Names are provided as aids for further
`searching of the compound of interest in Chemical Abstracts and elsewhere.
`Descriptors are appended to the entry if more than one registry number may be
`associated with the compound.
`Chemical Abstracts Name(s). The uninverted form of the CAS Index Name
`appears in native font following the CAS Registry Number. When a specific
`isomer is being discussed, stereochemical descriptors have been included to
`more clearly delineate that isomer.
`-
`Alternate Name(s). Other chemical names that identify the entry, trivial
`names, experimental drug codes, and current (and former) trademarks are listed.
`Listing of trademarks is for information purposes only and it should not be
`assumed that the trademarks are in current use. The first letter of each trademark
`is capitalized; absence of capitalization, however, does not preclude that a name
`
`vii,
`
`BAY 000144
`
`

`
`,
`
`
`
`
`
`
`
`Alternate names and/or
`trademarks (capitalized)
`of title compound
`
`
`
`
`
`,
`
`@ Chemical Abstracts
`
`
`
`(2R)—3,4—Dihy~
`[59—o2—9]
`ct-Tocopherol.
`9571.
`dro-2,5,7,8—tetramethy1—2—[(4R,8R)~4,8,12—trimethy1-
`tlidecyl]-2H- 1-benzopyran-6-ol;
`(+)-2,5,7,8—tetrame—
`thyl-2—(4’,8’,12’—trimethyltridecyl)-6—chromanol; R,R,—
`Percentage
`R-0:-tocopherol; d—'oz-tocopherol; 5,7,8—trimethyltocol;
`C0mP0Sili°D \Optovit; Tocovital. C29H5oO2; mol wt 430.70. C
`.
`.
`'
`f the
`naturally occurring forms of vitamin E .
`chest
`
`
`
`'
`°
`wheat germ: H. M. Evans et al., J. Biol: Chem. 113
`
`.
`
` 59, 1154 (1937); 60, 700 (1938). Synthesis of dl—form:
`
`Literature
`
`references
`
`P. Karrer et al., Helv. Chim. Acta 21, 520, 820 (1938);
`F. Bergel et al., J. Chem. Soc. 1938, 1382. Total syn-
`thesis of all 8 stereoisomers: N. Cohen et al.,‘ Helv.‘
`158 (1981). Clinical trial in Alzheimer’s
`disease. M. Sano et al., N. Engl. J. Med. 336, 1216
`
`
`
`
`
`
`
`
`
`
`
`A. Pryor, Free Radical Biol. Med. 28, 141-164 (2000).
`CH; . CH3
`
`1380 ( 1997). Review of bioavailability from vitamin
`E supplements: M. G. Traber, Bz'oFactors 10, l15—120
`(1999). Review of clinical trials in heart disease: W.
`
`CH3
`
`.
`[C\<l§36.l *3-0°
`
`CH3
`0
`Transparent needles, mp 2.5-3.5 .
`-
`-. e); [a]§26_1 +o.3_2° (ethanol).
`‘Acetate.
`[58-95-7] Spondyvit. C3,H52O3; mol wt
`472.74. Light yellow oil. Crystallized at —30° as needle-
`like crystals, mp 26.5—27.S°.
`[a],2,5 +o.25° (c = 10 in
`chloroform);_ fa]? +3.2° (in ethanol).
`dl—a~
`dl-ac-Tocopherol
`acetate.
`[52225—20—,4]
`Tocopheryl acetate; Detulin; Ephynal; Eusovit; Evion.
`Comprehensive description: B. C. Rudy, B. Z. Sen-
`kowski, Anal. Pr0files_Drug Subs. 3, 11l~l26 (1974).
`Pale yellow, viscous liquid. mp --
`~ 5°. dz” 0 9533.
`bP0.0l 134°? bPo.o25 194°? bPo.3 224°- "123
`~
`uv max (cyclohexane): 285.5 nm. Practlca
`water. Freely sol in acetone, chloroform, ethe
`readily so] in alc.
`USE: As an antioxidant in vegetable oils -
`ening.
`
`
`
`
`
`
`.
`
`
`
`THERAP CAT: Vitamin E supplement.
`THERAP CAT (VET): Vitamin E supplement.
`
`_
`
`.
`
`-
`
`Therapeutic category
`(veterinary)
`
`
`
`
`
`ix
`
`BAY 000145
`
`Molecular weight
`
`Molecular formula
`
`
`
`Chemical information
`
`.
`
` Biological,
`pharmacological,
`etc. information
`
`
`
`-
`
`Physical data for
`‘
`title compound
`
`'
`
`Derivatives of title
`compound
`
`
`
`
`
`Derivative Compound
`Literature references
`
`Physical data for
`derivative
`
`
`
`
`
`.
`Derlvatlve Compound
`_
`_
`Registry Number
`
`
`Alternate names and/or
`trademarks (capitalized)
`of the derivative
`compound
`
`
`
`
`Therapeutic category
`(in humans)
`
`1
`
`_
`
`-
`
`I
`
`

`
`may either currently be a proprietary name, or may once have been the subject
`of proprietary rights. If known, the company associated with a particular trade—
`mark (as a manufacturer, distributor or trademark owner) is listed alongside the
`trademark in the Name Index.
`A
`
`Molecular Formula, Molecular weight, % Composition. Elements in the
`molecular formula are listed according to the Hill convention (C, H, then other
`elements in alphabetical order). Formula and molecular weight are provided for
`all title compounds having a specific known structure. The 1999 IUPAC Stan-
`dard Atomic Weights have been used to calculate all molecular weights.
`Literature References. A concise reference history of each compound is
`provided. Frequently, there is a brief description or capsule statement, although
`in some monographs, particularly those on significant biological substances, a
`lengthier description is given. References to isolation, preparation or synthesis,
`patent information, and structural studies are cited. While reference is made to
`various methods of synthesis, the intent is to give a representative, but by no
`means exhaustive list. Patent numbers are provided merely as a source of pre-
`parative information; however, whenever possible, the product patent has been
`cited in monographs. Patents are cited using the two letter international country
`code followed by the number in boldface print; the year of publication and the
`assignee are included if known. References to pharmacology or biological ac-
`tivity, clinical trials, and toxicity studies may be included, where appropriate.
`Review articles, where available, are usually cited at the end of the references.
`Reviews pertaining to a group of closely relatedcompounds or to a family of
`natural substances are generally listed only in the monograph for the parent
`element or compound. Literature references are cited in the conventional man-
`ner; journal abbreviations (with notable exceptions listed in the Table of Ab—
`breviations) generally correspond to those in Chemical Abstracts Service
`Source Index (CASSI). The number of the first page of the reference is given;
`first and last page numbers are listed for reviews.
`Structure. For this edition, all structures have been drawn according to cur-
`rent conventions using CambridgeSoft’s ChernDraw‘”‘ software package. Struc~
`tural depictions, including stereochemistry, if relevant, are included in over
`6,500 monographs. Structures that do not correspond precisely to the mono-
`graph title have been labeled to identify the specific form depicted. Standard
`conventions of heavy wedges and dotted lines to show bonds directed above
`or below the plane of the paper are used where appropriate. Whenever possible,
`double bond geometry has been defined within the structure. Amino acid res-
`idues are assumed to be L unless specified otherwise. In addition, more than
`2,000 monographs contain line formulae showing molecular arrangements.
`Physical Data. Data are cited as found in the literature. When several alter~
`nate data values appear in the literature, the data is evaluated and representative
`selections are made. The values are then reported with the corresponding
`source. Whenever possible, the color of a substance is stated, but the absence
`of color (white or colorless) is often omitted. Temperatures are given in degrees
`Celsius (centigrade), unless otherwise noted. When solubilities are determined
`at room temperature (about 25°C), the temperature is generally omitted. When
`optical rotations are measured in water, the solvent is usually not specified. For
`ultraviolet absorption measurements, the solvent is given within parentheses.
`BAY 000146
`
`

`
`
`
`~r,>:¢ea,v::::-,5:2-‘
`
`
`
`:1;--,-,-,-,5.-.;;v».-»-pg‘:-,::
`
`Aneffort has been made to. provide toxicity data (e.g. LD50, LC50, et