Bisantrene B 251 - Stadalax (Stada Chemie) Tempolax (Hommel) GB: Tirgon (Woelm) I: Vinco (OW) Vinco-Abfiihrperlen (0TW)-comb. numerous combination preparations F: Contalax (3M SantC) J: Dulcolax (Boehringer Ing.) Pilules Dupuis (SynthC1abo)-comb. Bisantrene (CL-2 16942) Prtpacol (Guerbet)-comb. Dulcolax (Boehringer Ing.) Alaxa (Angelini) Dulcolax (Fher) Fisiolax (Manetti Roberts)- comb. Normalene (Montefarmaco) Anan (Ono) Biomit (Sampo)-comb. Cathalin (Hokuriku)-comb. Ethanis (Taisho)-comb. Lax (Kanto)-comb. Satolax-10 (Sato) Telemin Soft (Funai)-comb. Vemas (Nippon Zoki)- comb. Vencoll (Maruko)-comb. USA: Dulcolax (Novartis Consumer) Evac-Q-Kwik (Savage) Fleet Prep Kits (Fleet) ATC: LO1 Use: intercalanting antineoplastic (against adult acute non-lymphocytic leucemia) RN: 78186-34-2 MF: C2,HZ2N8 MW: 398.47 LD,,: 245 mgkg (M, route unreported) CN: 9,lO-anthracenedicarboxaldehyde bis(4,S-dihydro-1 H-imidazol-2-ylhydrazone) dihydrochloride RN: 71439-68-4 MF: C2,H2,N8 . 2HCI MW: 471.40 onthrocene vinylene 9,10,11,12-tetrahydro- carbonate 9.10-[4,5][1 ,J]dioxolo- anthracen-14-one leod tetracetote 2-hydrazino- A'-irnidazoline 9,lO-dihydro-9,lO- ethonoonthracene- 11,lZ-dial (I) 9.1 0-anthracene- dicarboxaldehyde Bisantrene DOS 2 850 822 (American Cyanamid; appl. 23.1 I .I%%; USA-prior. 28.1 I. 1977, 5.5.1978, 19.9.1978, 2.10.1978). US 4 187 373 (American Cyanamid; 5.2.1980; appl. 2.10.1978). Murdock, K.L. et al.: J. Med. Chem. (JMCMAR) 25, 505 (1982). Formulation(s): vial 50 mg, 250 mg, 500 mg Trade Name(s): F: Zantrene (Lederle; 1990 as USA: Cyabin (Lederle; as dihydrochloride); wfm dihydrochloride); wfm 252 B Bisbentiamine Bisbentiamine ATC: ~11 (Benzoylthiamine disulfide) Use: neurotropic analgesic, vitamin B ,- derivative RN: 2667-89-2 MF: C38H42Nn06S2 MW: 770.94 EINECS: 220-206-6 LD,,: 194 mglkg (M, i.v.); 9 glkg (M, p.0.) CN: N,l\r-[dithiobis[2-[2-(benzoyloxy)ethyl]-l-methyl-2,l-ethenediyl]]-bis[N-[(4-amino-2-methyl-5- pyrimidinyl)methyl]formamide] NaOH 12/KI or K3[Fe(CN)6] I N-(4-omino-2-methylpyrimidin- 5-ylmethy1)-N-(4-hydroxy-1- methyl-2-mercaptobut- 1 -enyl)- formomide - CH, NH, thiamine disulfide (I) benzoyl Bisbentiamine chloride Reference(s): US 3 109 000 (Tanabe; 1963; J-prior. 1960). GB 922 444 (Tanabe; appl. 1961; J-prior. 1960). similar method: DOS 1 954 51 9 (Hitachi; appl. 29.10.1969). Formulation(s): cps. 50 mg Trade Name(s): D: Neuro-Fortamin (Axhe)- J: Beston (Tanabe) comb.; wfm Bisoprolol ATC: C07AB07 Use: beta blocking agent RN: 66722-44-9 MF: C,,H3,NO4 MW: 325.45 CN: (+)-1-[4-[[2-(1-methylethoxy)ethoxy]methyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol fumarate RN: 104344-23-2 MF: C,,H3,N04 . 1/2C4H,04 MW: 766.97 Bisoprolol B 253 0 DOH CI&~ . NaO* HO - 111 eplchlorohydrln (U) 4-hydroxy- 2-isopropoxy- 4-[(2-isopropoxyethoxy)methyl]- benzyl alcohol ethonol (I) phenol 2-[[4-(2-isopropoxyethoxy)methyl]- isopropyl- Bisoprolol phenoxymethyl]oxirane (111) omine (1V) phcnal phenyl glycidyl 1 -phenoxy-3-iso- ether propylomino-2- propanol (V) 1 (CH20), . HCI v + CH3 * VI H,C/"O 0-CH, poraform- diethyl carbonate 5-phenoxymethyl- "Idehyde 3-isopropyl-2- oxazolidinone 5-(4-chloromethylphenoxy~ methyl)-3-isopropyl-2- oxazolidinone (YI) 5-[4-[(2-isopropoxyethoxy)methyl]phenoxyrnethyl]- 3-isopropyl-2-oxazolidinone (YII) KOH. C2H,0H V,I Reference(s): Harting, J. et al.: Arzneim Forsch. (ARZNAD) 36, 200 (1986). a DOS 2 645 710 (Merck Patent GmbH; appl. 9.10.1976). US 4 258 062 (Merck Patent GmbH; 24.3.1981; appl. 30.5.1979; D-prior. 9.10.1976). b DOS 3 205457 (Merck Patent GmbH; appl. 16.2.1982). Formulation(s): f. c. tabl. 10 mg; f. c. tabl. 5 mg, 10 mg (as fumarate) Trade Namefs): D: Bisobloc (Azupharma) F: Dttensiel (Lipha Santt; GB: Emcor (Merck) Concor (Merck; 1986) 1987) Monocor (Wyeth) Fondril (Procter & Gamble) Soprol (Wyeth-Lederle; Monoxide 10 (Wyeth)- 1988) comb. 254 B Bitolterol I: Concor (Bracco) USA: Zebeta (Lederle) Ziac (Leder1e)-comb. Bitolterol ATC: R03AC17 Use: selective P2-adrcnoccptor agonist, bronchodilator RN: 30392-40-6 MF: C18H,,NOs MW: 461.56 CN: 4-methylbenzoic acid 4-[2-[(I ,I -dimethylethyl)arnino]-l-hydroxycthyl]-l,2-phenylene ester mesylate RN: 30392-41-7 MF: CZ8H3,NO5. CH403S MW: 557.66 EINECS: 250-177-5 LD,,,: 31.4 mglkg (M, i.v.);41 16 rnglkg (M, p.0.); 44 mgkg (R, i.v.); >6221 mglkg (R, p.0.) L1 J , I CH, 1. sodium ethylote OH 2. p-toluoyl chloride 2-chloro-3',4'- tert-butyl- 2-tert-butylamino-3'.4' dihydroxy- ornine dihydroxyacetophenone acetophenone Keference(s): DOS 2 015 573 (Sterling Drug; appl. 1.4.1970; USA-prior. 1.4.1969). Corrigan, J.R. et al.: J. Am. Chem. Soc. (JACSAT) 71, 530 (1949). Fuller, B.F. et al.: J. Med. Chem. (JMCMAR) 19, 834 (1976). H2/Pd-C or NaBH4 '43C CH3 2-teh-butylarnino-3'.4'-bis- (p-toluoyloxy)ocetophenone (1) For~ndation(s): aerosol 10 ml (0.8 %); tabl. 4 mg OH H &0@$:i3 H,C / 0 0 4 CH3 Bitolterol Trade Name(s): I: Asmalene (Firmaj J: Effectin (Shionogi- Tolbet (Corvi) Winthrop; as mesylate) Bleomycin ATC: LOlDCOl Use: antineoplastic (peptide antibiotic) RN: 1 1 11 6-31-7 MF: C5,H84N1702,S3 MW: 141 5.57 EINECS: 234-356-5 LD,,,: 100 mg/kg (M, i.v.) CN: N1-[3-(dimethylsulfonio)propyl]bleomycinamide Bluensomycin B 255 50 % Bleomycin A,, 20 7% 'oleornycin B,. Bleomycin 4 From culture of Streptornyces verticillus by ion-exchange adsorption and column chromatographic purification (on alumina) via the copper complex. Referencers): DE 1 217 549 (Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai = Microbial Chemistry Research Foundation; Tokyo; appl. 5.3.1964; J-prior. 5.3.1963). Formulation(s): amp. 15 mg (as sulfate) Trade Namers): D: BLEO-cell (cell pharm) I: Bleomicina (RhBne- Rleo S (Nippon Kayaku; as Bleomycinum-Mack Poulenc Rorer) sulfate) (Mack, Illert.) gencrics USA: Blenoxane (Bristol-Myers F: Bleomycine Roger Bellon J: Bleo (N~ppon Kayaku; as Squibb Oncology/ (Roger Bellon) hydrochloride) Immunology; as sulfate) generics Bluensomycin ATC: A07AA Use: antibiotic RN: 1101 1-72-6 MF: C2,H,,N,0,, MW: 585.56 LD,,: 2250 mgkg (M, i. v.); >2500 mglkg (R, p.0.) CN: O-2-deoxy-2-(methylamino)-a-L-glucopyranosyl(l+2)-0-5-deoxy-3-C-(hydroxymethyl)-~- lyxofuranosyl-(l~2)-1-[(aminoiminomethyl)amino]-1-deoxy-D-sc~llo-inositol 5-carbamate 256 B Bolasterone Bluensomycin From fermentation solutions of Strepto~nyces bluensis NRRL 2876 Reference (s): Mason, O.J. et al.: Antimicrob. Agents Chemother. (AACHAX) 1963, 607. Bergy, M.E. et a].: Antimicrob. Agents Chemother. (AACHAX) 1963,614. DAS 1 183 631 (Upjohn; appl. 19.7.1962; USA-prior. 7.8.1961). structure: Bannister, B.; Argoudelis, A.D.: J. Am. Chem. Soc. (JACSAT) 85, 119,234 (1963). McGilveray, I.J.; Rinehart, U.L.: J. Am. Chem. Soc. (JACSAT) 87,4003 (1965). Trade Name(s): USA: Bluensomycin "Upjohn" (Upjohn); wfm Bolasterone ATC: G03BA Use: anabolic RN: 1605-89-6 MF: C,,H,,O, . MW: 316.49 EINECS: 216-519-2 CN: (7a,17~)-17-hydroxy-7,17-dimethylandrost-4-en-3-one 3p.178-dihydroxy-170-methyl- 5-androsiene (cf. methyltestosierone synthesis) p-quinone aluminum tri-tert-butylate 178-hydroxy-17-methyl- andrasta-4,6-dien-3-one (I) 1. CuC12 2. isomer resolution b methyl- magnesium bromide Bolasterone Boldenone undecenylate B 257 Reference(s): US 3 341 557 (Upjohn; 12.9.1967; prior. 5.6.1961, 6.1 1.1960, 6.6.1958). Campbell, J.A.; Babcock, J.C.: J. Am. Chem. Soc. (JACSAT) 81,4069 (1959). Trade Name(s): USA: Myagen (Upjohn); wfm Boldenone undecenylate ATC: G03B Use: anabolic RN: 13103-34-9 MF: C,,HN03 MW: 452.68 EINECS: 236-024-5 CN: (17~)-17-[(I-oxo-l0-undecenyl)oxy]androsta-l,4-dien-3-one boldenone RN: 846-48-0 MF: C,,H,,02 MW: 286.42 EINECS: 212-686-0 pyridine ___, 0 Reference(s): BE 623 277 (Merck AG; appl. 5.10.1962; D-prior. 5.10.1961). boldenone 10-undecenoyi chloride starting material: CA 803 490 (Upjohn; appl. 1956; USA-prior. 1955). GB 922 525 (Loevens Kemiske Fabrik; valid from 6.1 1.196 1 ; prior. 9.1 1.1960). US 2 837 464 (Schering; 1958; prior. 1955). US 2 875 196 (Oh Mathieson; 1959; prior. 1956, 1955). Meystre, Ch. et al.: Helv. Chim. Acta (HCACAV) 39, 734 (1956). Baldenone undecylenote Trade Name(s): D: Vebonol (Ciba); wfm USA: Parenabol (Ciba); wfm Bopindolol ATC: C07AA17 Use: P-adrenoceptor antagonist, antihypertensive RN: 62658-63-3 MF: C2,H2,N20, MW: 380.49 LD,,: 17 mgkg (M, i.v.) CN: (&)-1-[(I,]-dimethylethyl)amino]-3-[(2-methyl-1 H-indol-4-yl)oxy]-2-propanolbenzoate (ester) (E)3-butenedioate (1:l) RN: 62658-64-4 MF: C2,H2,N2O3. C4H404 MW: 496.56 LD50: 17mglkg (M, i.v.) 258 B Bornaprine 4-hydroxy-2- epichloro- 2-methyl-4- methylindole hydrin oxironylmethoxyindole (cf. mepindolol synthesis) 4-(3-tert-butylomino- benzoic onhydride Bopindolol 2-hydroxypropoxy)-2- methylindole (I) Reference(s): DOS 2 635 209 (Sandoz; appl. 5.8.1976; CH-prior. 15.8.1975). GB 1 575 509 (Sandoz; appl. 13.8.1976; CH-prior. 15.8.1975). GB 1 575 510 (Sandoz; appl. 13.8.1976; CH-prior. 15.8.1975). Formulation(s): tabl. 1 rng Trade Name(s): D: Wandonorrn (Novartis J: Sandonorm (Novartis; as Pharma; 1989 as hydrogen malonate) rnalonate) Bornaprine ATC: N04AA11 Use: antiparkinsonian RN: 20448-86-6 ME;: C,,H11N02 MW: 329.48 LD,,: 26 mgkg (M, i.v.) CN: 2-phenylbicycl0[2,2,1]heptane-2-carboxylic acid 3-(diethy1arnino)propyl ester hydrochloride RN: 26908-91-8 MF: C,,H,,NO,. HC1 MW: 365.95 EINECS: 248-100-5 hydroquinone, cyclo- ethyl 2-phenyl- pentodiene ocrylole ethyl 2-phenyl- bicyc\o[2.2.1]-5- heptene-2-corboxylote (I) Brimonidine B 259 ethyl 2-phenyl- Z-phenylbicyclo- bicyclo[2.2. llheptane- [Z.Z.l]heptane- 2-corboxylote 2-corboxylic acid (11) Referencers): DE 1 044 809 (Knoll; appl. 16.6.1956). HO-N-CH, 3-diethylomino- 1 -propano1 Formulation(s): tabl. 4 mg (as hydrochloride) Bornoprine Trade Narne(s): D: Sormodren (Knoll) I: Sormodren (Ravizza) RN: 59803-98-4 MF: CllHl,BrN, MW: 292.14 LD,,: 160 mg/kg (M, p.0.) CN: 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine tartrate (1:l) RN: 70359-46-5 MF: C,,H,,BrN, . C,H,O, MW: 442.23 H~N-~~z bromobenzene 6-amino- ammonium 5-bromo-6- 5-bromo- thiocyonate thioureido- quinoxoline quinoxoline Reference(s): DE 2 538 620 (Pfizer; appl. 29.8.1975; GB-prior. 6.9.1974). we: WO 9 510 280 (Allergan; appl. 19.9.1994; USA-prior. 13.10.1993). WO 9 701 339 (Allergan; appl. 17.6.1996; USA-prior. 28.6.1995). WO 9 635 424 (Allergan; appl. 5.9.1996; USA-prior. 12.5.1995). Brimonidine I combinations: WO 9 613 267 (Allergan; appl. 20.10.1995; USA-prior. 27.10.1994). US 5 215 991 (Allergan; appl. 20.12.1990; USA-prior. 26.1.1990). 260 B Brinzolamide suspension formulations for controlled delively: WO 9 21 1 871 (Allergan; appl. 17.12.1991; USA-prior. 27.12.1990). WO 9 205 770 (Allergan; appl. 10.9.199 1; USA-prior. 27.9.1990). Formulation(s): eye drops 0.2 O/c Trade Name(s): GB: Alphagan (Allergan; as USA: Alphagan (Allergan; as tartrate) tartrate) Brinzolamide (AL-4862) ATC: SOlEC04 I Use: antiglaucoma, topical carbonic anhydrase inhibitor RN: 138890-62-7 MF: C,,H,lN,O,S, MW: 383.51 CN: (4R)-4-(Ethylamino)-3,4-dihydro-2-(3-me~namde 1,l- dioxide 0 3-ocetyl- thiophene v H3C CH, 3-(2,5,5-trimethyb 1.3-d1oxon-Z-yl)- 2-thiophene- sulfonomide (11) OH OH 2. so2 3. H2N-0-S03H b 11 W 3. hydroxylamine- H3C CH, 0-sulfonic ocid, HOSA 2.2-dimethyl- 3-(2,5,5-trimethyl- 1,3-proponediol 1 .~-dioxon-2-~l)- thiophene (I) 1. HCI. THF 3. NoBH.,. ethonol SH _____* 2. pyridinium perbromide OH 3. sodium borohydride (?)-3.4-dihydro-4- hydroxy-2H-thieno- [3,2-el-1,2-thiozine 1 ,l -dioxide (111) hydride OH 1,3-dibromo- (?)-2-(3-bromopropyl)- propone 3,4-dihydro-4-hydroxy- 2H-thieno[3.2-el-1.2- thiozine I ,1-dioxide (N) . (? )-3 .4-dihydro- 4- hydroxy-2H-thieno- [3,2-el-1,2-thiozine 1 ,l -dioxide (111) hydride OH 1,3-dibromo- (? )-2 -( 3-bromopropyl )- propone 3,4-dihydro-4-hydroxy- 2H-thieno[3.2-el-1. 2- thiozine. N,l -[dithiobis[ 2-[ 2-( benzoyloxy)ethyl]-l-methyl-2,l-ethenediyl]]-bis[N-[(4-amino-2-methyl- 5- pyrimidinyl)methyl]formamide] NaOH 12/KI or K3[Fe(CN)6] I N-(4-omino-2-methylpyrimidin- 5-ylmethy1)-N-(4-hydroxy- 1- methyl-2-mercaptobut- 1 -enyl )- formomide. Use: anabolic RN: 160 5-8 9-6 MF: C,,H,,O, . MW: 316.49 EINECS: 21 6-5 1 9-2 CN: (7a,17~ )-1 7-hydroxy-7,17-dimethylandrost-4-en-3-one 3p.178-dihydroxy-170-methyl- 5-androsiene (cf. methyltestosierone