Butenafine B 301 dimaleate RN: 1063-55-4 MF: C24H31N30S . 2C4H404 MW: 641.74 EINECS: 213-900-5 LD,o: 17.6 mgkg (M, i.v.); 296 mglkg (M, p.0.); 63 mglkg (R, i.v.); 264 mg/kg (R, p.0.); >50.7 mglkg (dog, i.v.) 1. NaNH, A - 1. sodium arnide 2. 1-methyl-4-(3- 2-butyrylphenothiazine chloropropy1)- Butaperozine piperozine Reference(s): DE 1 120 451 (Bayer; appl. 30.5.1956). US 2 985 654 (Schering Corp.; 23.5.1961; appl. 21.9.1956). Fonnulation(s): tabl. 0.1 mg, 0.25 mg, 0.5 mg Trade Name(s): D: Ostrogynal (Asche)-comb.; USA: Repoise (Robins); wfm wfm Butenafine Use: antifungal for topical use RN: 101828-21-1 MF: C2,H2,N MW: 317.48 CN: N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-N-methyl-1-naphthalenemethanamine hydrochloride RN: 101827-46-7 MF: CZ3Hz7N . HCl MW: 353.94 1. HZ. Roney-Ni, C,H,OH, methylornine (I) naphthalene-1 - N-methyl- carboxaldehyde 1 -nophthyl- methylamine (U) CZH,OH +I + 11 l-chlaramethyl- naphthalene (111) 302 B Butenafine 4-tert-butylbenzyl bromide 1. Na2C0,. DMF fl~, 2. HCI, C~H~OH , I1 + Br -, I CH3 Butenafine HCI 4-tert-butyl- benzaldehyde 1. Na2C0,. DMF 2. HCI. C2H50H IV + nr A N-methyl-4- tert-butyl- benzylamine (N) Butenafine 1 0 1. SOCI, H C H3 eCH3 I. AH THF , I CH3 2. HCI 1 4-tert-butyl- benzoic acid 1. SOCI, 2HCl - Butenofine Reference(s): a EP 221.78 1 (Mitsui Toatsu Chem.; appl. 3 1.10.1986; J-prior. 1.1 1.1985). b JP 03 200 747 (Kokai Tokkyo Koho; appl. 28.12.1989; J-prior. 2.9.1991). c,d EP 164 697 (Kaken Pharmaceutical Co.; appl. 6.6.1985; J-prior. 9.6.1984). preparation of N-methyl-1-naphthylmethylamine: Dalm, Zoller: Helv. Chim. Acta (HCACAV) 35 1348, 1353 (1952). Elslager, E.F; Johnson, J.L.; Werbel, L.M.: J. Med. Chem. (JMCMAR) 24 (21, 140 (1981). Baltzly, I.: J. Am. Chem. Soc. (JACSAT) 65 1984 (1943) Lutz et al.: J. Org. Chem. (JOCEAH) 12 760 (1947) Fnrrnulation(s): cream 1 %; sol. I % (als hydrochloride) Trade Narne(s): J: Mentax (Kaken; 1992) Volley (Hisamitsu) USA: Mentax (Bertek Pharms.) Butetamate B 303 Butetamate (Butethamate) ATC: SOlFA Use: antispasmodic RN: 14007-64-8 MF: C,,H2,N02 MW: 263.38 EINECS: 237-817-9 CN: a-ethylbenzeneacetic acid 2-(diethy1amino)ethyl ester citrate RN: 13900-12-4 MF: C,,H2,N02 . xC,H,O, MW: unspecified EINECS: 2-phenyl- 2-diethylaminoethyl bulyric acid chloride hydrochloride Reference(s): CH 291 375 (Hommel; appl. 1950). Engelhardt, A,: Arzneim Forsch. (ARZNAD) 11, 217 (1957). Forrnulation(s): sol. 14.5 mgI5 ml Trade Name(s): D: Baldicap (Giu1ini)-comb.; numerous combination I: wfm preparations; wfm Pertix-Hommel Liquidum GB: Cam (Rybar); wfm (Hommel); wfrn Pertix (Bonomelli Farm.)- comb.; wfm Butethamine ATC: NOlB Use: local anesthetic RN: 2090-89-3 MF: C,,H2,N202 MW: 236.32 CN: 2-[(2-methylpropyl)amino]ethanol Caminobenzoate (ester) monohydrochloride RN: 553-68-4 MF: C,,H2,,N202 . HCI MW: 272.78 LD,,: 36 mgkg (M, i.v.1; 28 mgkg (R, i.v.) ethanolamine isobutyl 2-isobutylomino- chloride chloride ethanol I 1 Butethamine 304 B Butibufen Reference(s): US 2 139 818 (Novocol Chem.; 1938; prior. 1935). Formulation(s): amp. Trade Name(s): USA: Dentocaine (Amer. Chem.); Monocaine formate wfm (Novocol); wfm Monocaine hydrochloride (Philadelphia Labs.); wfm Butibufen ATC: M02A Use: non-steroidal anti-inflammatory RN: 55837- 18-8 MF: Cl4HzOO2 MW: 220.3 1 EINECS: 259-849-2 LD,,,: 8 10 mgkg (M, p.0.); 1600 mgkg (R, p.0.) CN: a-ethyl-4-(2-methylpropy1)benzeneacetic acid sodium salt RN: 60682-24-8 MF: C,,H,,NaO, MW: 242.29 EINECS: 262-374-3 nitrile (cl. ibuprofen synthesis) 1. NaNH2 2. NaOH ~~c-1 k 1. sodium amide ethyl iodide (I) 1. NOH - 2. NaOH 3. HCI CH3 ethyl 4-isobutyl- phenylocetote DE 2 505 8 13 (Juste; appl. 12.2.1975). CH 573 89 1 (Juste; appl. 16.6.1975). US 4 031 243 (Juste; 21.6.1977; appl. 25.2.1975). I Butibufen alternative synthesis: EP 184 573 (Sanofi; appl. 28.11.1985; F-prior. 29.11 .l985). Formularion(s): cps. 350 mg; sachets 500 mg; suppos. 500 mg; tabl. 500 mg Butizide B 305 Trade Name(s): E: Mijal (Juste; 1992) Butizide (Buthiazide; Thiabutazide) ATC: C03E Use: diuretic, antihypertensive RN: 2043-38-1 MF: C, IH16ClN304S2 MW: 353.85 EINECS: 218-048-8 CN: 6-chloro-3,4-dihydro-3-(2-methylpropyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1 ,l -dioxide 4-amino-6-chlora- isovoleroldehyde Butizide 1.3-benzenedisulfomide (cf. chlarothiozide synthesis) Reference(s): GB 861 367 (Ciba; appl. 2.3.1959; USA-prior. 9.4.1958,9.6.i958, 29.7.1958, 29.9.1958). Werner, I.H. et al.: J. Am. Chem. Soc. (JACSAT) 82, 1161 (1960). Formulation(s): cps. 50 mg; drg. 50 mg Trade Name(s): D: Aldactone 50-Saltucin Saltucin (Boehringer Tri-Torrat (Boehringer (Boehringer Mannh.)- Mannh.) Mannh.)-comb. comb. Torrat (Boehringer F: EunCphran (Servier); wfm Modenol (Boehringer Mannh.)-comh. I: Kadiur (Boots 1talia)-comb. Mannh.)-comb. Saludopin (SIT)-comb. Butoconazole . ATC: GOlAFl5 Usc: topical antifungal RN: 64872-76-0 MF: C1,H17Cl,N,S MW: 41 1.78 LD,: >I600 mglkg (M, i.p.); ~3200 mg/kg (M, p.0.); 940 mglkg (R, i.p.) CN: (+)-1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-lH-imidazole mononitrate RN: 64872-77-1 MF: C,,Hl7CI3N2S . HN03 MW: 474.80 LD,: >3200 mglkg (M, p.0.); 1720 mg/kg (R, p.0.) * I f 'OH imidazole CI p-chlorobenzyl- epichloro- 4-(4-chloropheny1)- magnesium bromide hydrin 1-chloro-2-butonol 306 B Butoctamide CI 1. thionyl chloride 2. 2,6-dichloro- thiophenol 1 -14-(4-chlorophenyl)- 2-hydroxybutyl]-1 H- imidozole (1) Reference(s): Walker, K.A.M. et al.: J. Med. Chem. (JMCMAR) 21, 840 (1978). US 4 078 071 (Syntex; USA-prior. 28.7.1975). DOS 2 800 755 Formulation(s): vaginal cream 2 % Trade Narne(s): F: Gynomyk (Cassenne) USA: Femstat (Syntex; 1986); wfm Butoctamide Use: hypnotic, antineoplastic RN: 32838-26-9 MF: C,,H,,NO, MW: 215.34 LD,,: 476 mg/kg (M, i.p.); 2000 mglkg (M, p.0.) CN: N-(2-ethylhexy1)-3-hydroxybutanamide diketene 2-ethylhexyl- N-(2-ethylhexy1)-3-oxobutonamide (I) omine Reference(s): DOS 1 768 445 (Lion Hamigaki; appl. 15.5.1968; J-prior. 15.5.1967). US 3 639 457 (A. Sakuma et al.; 1.2.1972; J-prior. 15.5.1967). Hz, Roney-Ni I A Trade Name(s): J: Listomine (Lion; as hemisuccinate) OH 0 ButofiloloI B 307 Butofilolol Use: B-adrenoceptor blocker RN: 64552-17-6 MF: C,,H,$NO, MW: 31 1.40 CN: (~)-1-[2-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-5-fluorophenyl]-I-butanone phenol chloride butyrophenone tert-butyl- amine Butofilolol F hydride 5-fluoro- 1 -chlara-3-tert- salicyl- butylamino-2- aldehyde proponol F (11) propylrnognesium bromide chromium trioxide DOS 2 52'8147 (CM Industries; appl. 24.6.1975; GB-prior. 28.6.1974). Trade Name(s): F: Cafide (Lab. Labaz); wfm 308 B Butomhanol Butorphanol ATC: N02AFO1 Use: analgesic RN: 42408-82-2 MF: C2,H2YN02 MW: 327.47 EINECS: 255-808-8 CN: 17-(cyclobutylmethyl)morphinan-3,14-diol tartrate (1:l) RN: 58786-99-5 MF: C21H2yN02. C4HhOh MW: 477.55 EINECS: 261-443-5 LD,,: 36 mgkg (M, i.v.); 395 mgkg (M, p.0.); 17 mgkg (R, i.v.); 3 15 mglkg (R, p.0.); 10 mgkg (dog, i.v.); >50 mgkg (dog, p.0.) 1. NaH, tert-ornyl olcohol H~c.~~ . H,C-CN THF. -BO°C 0g butyl- b I n oceto- u lithium nitrile 7-methoxy- tetrolone 7-methoxy-2,2-tetro- methylenetetralone 0 v*O LiAIH4, THF H~~,~$ HC1, (C2H5)20 H~~*~~~~~ c!A0fic"3 pyridine, CH2C12 HO b H 0 b Ir ethyl NC "2N chloroforrnate benzaic acid v 0 N-ethoxycorbonyl-3-methoxy- 8.1 4-didehydromorphinon (N) IV 3 . cyclobutane- corbonyl chloride 0 3-methoxy-8.14- didehydromorphinon Butriptyline B 309 1. Pyridine * HCI or HBr I HO~ I 2. racemate resolution with (-)-tartoric acid V1 Reference(s): US 3 775 414 (Bristol-Myers; 27.1 1.1973; appl. 10.5.1972). US 3 819 635 (Bristol-Myers; 25.6.1974; prior. 8.9.1971, 13.1.1972). DOS 2 243 961 (Bristol-Myers; appl. 7.9.1972; USA-prior. 8.9.1971, 13.1.1972). DOS 2 265 255 (Bristol-Myers; appl. 7.9.1972; USA-prior. 8.9.1971, 13.1.1972). DOS 2 265 256 (Bristol-Myers; appl. 7.9.1972; USA-prior. 8.9.1971, 13.1.1972). US 3 980 641 (Bristol-Myers; 14.9.1976; appl. 31.7.1975). Monkovic, J. et al.: J. Am. Chem. Soc. (JACSAT) 95,7910 (1973). alternative syntheses: from 7-methoxy-2-tetralone: US 4 017 497 (Bristol-Myers; 12.4.1977; appl. 18.11.1975). from (-)-1-(4-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline: US 4 115 389 (Bristol-Myers; 19.9.1978; appl. 2.5.1977). Formulation(s): nasal spray 15 mgl2.5 ml Trade Name(s): I: Stadole (Bristol Europe; J: Stadol (Bristol; 1986) USA: Stadol (Bristol-Myers 1984); wfm Squibb; 1978) Butriptyline ATC: N06AA15 Use: antidepressant RN: 35941-65-2 MF: CZIH2,N MW: 293.45 CN: (~)-10,11-dihydro-N,N,~-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propanamine hydrochloride RN: 5585-73-9 MF: C,IHz7N . HCI MW: 329.92 EINECS: 226-983-8 LD,,: 48 mgkg (M, i.v.); 345 mglkg (M, p.0.); 700 mgkg (R, p.0.) 310 B Butropium bromide 10.1 1 -dihydro- 3-dimethylomino- 5H-dibenzo[o.d]- 2-methylpropyl- cyclohepten-5-one magnesium chloride Butriptyline BE 61 3 750 (Ayerst; appl. 9.2.1962; CDN-prior. 10.2.1961). US 3 409 640 (Schering Corp.; 5.1 1.1968; appl. 22.7.1959). Formulation(s): tabl. 25 mg (as hydrochloride) Trade Name(s): GB: Evadyne (Ayerst); wfm I: Evadene (Wyeth-Ayerst) Butropium bromide Use: antispasmodic RN: 29025-14-7 MF: C,,H,,BrNO, MW: 532.52 EINECS: 249-375-4 LD,,,: 6400kglkg (M,i.v.); 1500mgflcg(M,p.o.); 21 mgkg (R, i.v.) CN: [3(S)-endo]-8-[(4-butoxyphenyl)methyl]-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8- azoniabicyclo[3.2. lloctane bromide 4-butoxybenzyl hyoscyornine I Butropium bromide bromide L Reference (s): DOS 1 950 378 (Eisai Kabushiki Kaisha; appl. 6.10.1969; J-prior. 18.2.1969). US 3 696 I10 (Eisai Kabushiki Kaisha; 3.10.1972; J-prior. 18.2.1969). Fornmlation(s): amp. 4 mg Trade Name(s): J: Coliopan (Eisai; 1974) . RN: 204 3-3 8-1 MF: C, IH16ClN304S2 MW: 353.85 EINECS: 21 8-0 4 8-8 CN: 6-chloro-3,4-dihydro- 3-( 2-methylpropyl )-2 H-1,2,4-benzothiadiazine-7-sulfonamide 1 ,l -dioxide 4-amino-6-chlora- isovoleroldehyde. Butofilolol Use: B-adrenoceptor blocker RN: 6455 2-1 7-6 MF: C,,H,$NO, MW: 31 1.40 CN: (~ )-1 -[ 2-[ 3-[ (1,1-dimethylethyl)amino ]-2 -hydroxypropoxy ]-5 -fluorophenyl]-I-butanone phenol chloride. 21 mgkg (R, i.v.) CN: [3(S)-endo ]-8 -[ (4-butoxyphenyl)methyl ]-3 -( 3-hydroxy-1-oxo-2-phenylpropoxy )-8 -methyl- 8- azoniabicyclo[3.2. lloctane bromide 4-butoxybenzyl hyoscyornine I Butropium