Bicalutamide B 241 Bicalutamide (ICI- 176334) ATC: L02BB03 Use: non-steroidal antiandrogen, antineoplastic, anti(pr0state)cancer RN: 90357-06-5 MF: CI8Hl4F4N2O4S MW: 430.38 CN: (f)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide R-enantiomer RN: 113299-40-4 MF: C1,H,,F4N,O4S MW: 430.38 S-enantiomer RN: 113299-38-0 MF: C18H14F4N204S MW: 430.38 F 0 H202. NoOH 0 NOH. THF 0 H~c#~/~~~ , 0 4-fluoro- H3c?7+'cH3 - CH2 thiophenol (I) F methyl methocrylate methyl 2.3-epoxy- 2-rnethylpropionote methyl Z-hydroxy- 2-methyl-3-(4-fluoro- pheny1thio)propionote (11) aniline (Ill), thianyl chloride. D MA N-(4-cyano-3-trifluorcmethylphenyl)- 3-(4-fluorophenylsuIfony1)-2-hydroxy- 2-methylpropionomide (N) J-chloroper- benzoic acid (V) I Bicolutomide I methocryloyl chloride 4'-cyono-3'-trifluoro methylmethocryl- onilide NOH. THF H 4'-cyano-3'-trifluoro- methyl-2.3-epoxy-2- methyl-propiononilide (VI) 242 B Bietamiverine Reference(s): EP 100 172 (ICI; appl. 8.7.1983; UK-prior. 23.7.1982). active enantiomer (R-(-)-bicalutamide),for treating e. g. prostare cancel; acne: WO 9 519 770 (Sepracor Inc.; appl. 27.7.1995; USA-prior. 21.1.1994). combination with progesterone antagonists: DE 4 318 371 (Schering AG; 1.12.1994; D-prior. 28.5.1993). combination with sex steroid biosynthesis inhibitors: WO 9 100 733 (Endorecherche Inc.; 24.1.1994; USA-prior. 7.7.1 989). Formulation(s): tabl. 50 mg Trade Name(s): D: Casodex (Zeneca) GB: Casodex (Zeneca) USA: Casodex (Zeneca) Bietamiverine (Dietamiverin) ATC: A03AA Use: antispasmodic RN: 479-81-2 MF: C,,H30N202 MW: 318.46 EINECS: 207-538-7 CN: a-phenyl-1-piperidineacetic acid 2-(diethy1amino)ethyl ester dihydrochloride RN: 2691-46-5 MF: C,yH,oN,02 .2HCl MW: 391.38 EINECS: 220-262-1 LD,,: 55 mgkg (M, i.v.); 1247 mglkg (M, p.0.) a-chlorophenyl- 2-diethylamino- acetyl chloride ethanol c I 2-phenyl-2-chloroacetic acid 2-(diethylamina)ethyI ester (I) H 0 I + piperidine ICH3 w0-NVcH3 Bietamiverine Reference(s): DE 859 892 (Nordmark; appl. 1950). Trade Namefsi: D: Spasmaparid (Nordmark); J: Sparine A (Tokyo Tanabe) w fm Bietaserpine ATC: C02AA07 Use: antihypertensive RN: 53-18-9 MF: C7,HS3N3Oy MW: 707.87 EINECS: 200-165-0 CN: (3~,16~,17a,l8~,20a)-1-[2-(diethylamino)ethyl~-11,17-dimethoxy-l8-[(3,4,5- trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester Bifluranol B 243 bitartrate (1:l) RN: 11 11-44-0 MF: C3,HS3N309. C4H606 MW: 857.95 EINECS: 214-180-5 1. NOH 2. pH3 CIAJ'LCHs 0-CH3 -b 1. sodium hydride 2. 2-diethylominoethyl reserpine (9. v.1 chloride Bietoserpine i Reference(s): FR 1 256 524 (Dautreville et Lebas et A. Buzas; appl. 13.2.1959). FR-M 102 (Soc. Nogentaise de Prod. Chim. et A. Buzas; appl. 3.8.1960). Trade Namefs): F: Tensibar (Lefranca); wfrn I: Pleiantensin simplex (Guidotti); wfm Bifluranol ATC: G03HA Use: antiandrogen, treatment of benign prostatic hypertrophy RN: 34633-34-6 MF: C,,H,,F,O, MW: 292.33 CN: (R*,S*)-4,4'-(1-ethyl-2-methyl-l,2-ethanediyl)bis[2-fluorophenol] 3-chloro-2- trans-2.3-bis(3-fluora-4-methoxy- pentanone phenyl)-2-pentene (11) Bifluranol i___l 244 B Bifonazole 3-chloro-2- (R*,S*)-2.3-bis(3-fluoro-4-rnethoxy- pentonol pheny1)pentone Reference(s): DE 2 I10 428 (Biorex; appl. 4.3.1971; GB-prior. 16.3.1970). US 4 051 263 (Biorex; 27.9.1977; GB-prior. 16.3.1970). Formulation(s): amp. Trade Name(s): GB: Prostarex (Biorex); wfrn Bifonazole (Bifonazolum) ATC: DOlAClO Use: topical antimycotic (inhibitor of erg~sterin biosynthesis in yeasts and dermatophytes) RN: 60628-96-8 MF: C,,H,,N, MW: 310.40 EINECS: 262-336-6 LD,,: 57 rngkg (M, i.v.); 2629 mglkg (M, p.0.); 63 mgkg (R, I.v.); 1463 mgkg (R, p.o.); >500 mgkg (dog, p.0.) CN: 1-([1,1'-biphenyl]-4-ylphenylrnethyl)-lH-imidazole monohydrochloride RN: 60629-09-6 MF: CZ2H,,N2, HC1 MW: 346.86 sulfate RN: 60629-08-5 MI? CZ2H,,N,. xH20,S MW: unspecified biphenyl benzoyl chloride / / OH CI (2)-4-phenylbenz- (-4)-4-(chlorophenyl- Bifonazole hydro1 (I) rnethy1)biphenyl Binedaline B 245 1 -1'-sulfinyl- bisirnidazole Reference(s): DOS 2 461 406 (Bayer; appl. 5.12.1975; USA-prior. 24.12.1974). US 4 118 487 (Bayer; 3.1 1.1978; appl. 5.12.1975; prior. 24.12.1974). effective mechanism: Berg, D. et al.: Arzneim Forsch. (ARZNAD) 34 (I), 139 (1984). Formulation(s): cream 10 mg (1 %); gel 10 mg; lotion 1 %; powder 10 mg (1 %); sol. 10 mg (1 %) Trade Name(s): D: Bifomyk (Hexal) F: Amycor (Lipha SantC; I: Azolmen (Menarini; 1987) Bifon (Dennapharm) 1987) Bifazol (Bay ropharm; Mycospor (Bayer; 1983) Amycor onychoset (Lipha 1986) SantC)-comb. Binedaline (Binodaline) ATC: N06AB Use: antidepressant RN: 60662-16-0 MF: ClyHz3N3 MW: 293.41 LD,,; 54 mgkg (M, i.v.); 770 mglkg (M, p.0.); 27 mgkg (R, i.v.) CN: N,N,N-trimethyl-N-(3-phenyl- l H-indol-1 -yl)- 1.2-ethanediamine monohydrochloride RN: 57647-35-5 MF: ClyHz,N3 . HCl MW: 329.88 EINECS: 260-877-2 LD,: 54 mgkg (M, i.v.); 760 mglkg (M, p.0.); 26 mgkg (R, i.v.); 1160 mgkg (R, p.0.); >20 mg/kg (dog, i.v.) - 1. NaN02, HCI + H3C-MgBr 2. NH, b 2-amino- methylmagnesium 2-(1 -phenylvinyl)- benzophenone bromide aniline N-(3-phenylindal-1 -yl) ocetamide (11) \ "% 4-phenyl- cinnoline (1) 246 B Biotin 1. KOH methyl 4-toluene- NaH ___, sulfonote p3 C,~N\ . CH3 1. potassium hydroxide 2. 2-(dimethylomino)- ethyl chloride DOS 2 512 702 (Siegfried AG; appl. 22.3.1975; CH-prior. 29.3.1974). US 4 204 998 (Siegfried AG; 27.5.1980; CH-prior. 29.3.1974). Schatz, F. et al.: Arzneim Forsch. (ARZNAD) 30,919 (1980). synthesis of 1,4-dihydro-4-phenylcinnoline: Simpson, J.C.F. et al.: J. Chem. Soc. (JCSOA9) 1945,646. Scheifele, H.J. Jr. et al.: Org. Synth. (ORSYAT) 32, 8 (1952). Sternbach, L.H. et al.: J. Org. Chem. (JOCEAH) 26,4488 (1961). Formulation(s): tabl. 25.5 mg Trade Name(s): J: lxprim (Roussel-Uclaf) Biotin (Vitamin B7; Vitamin H) ATC: A1 lHAO5 Use: growth factor, vitamin RN: 58-85-5 MF: C,,H,,N,O,S MW: 244.32 EINECS: 200-399-3 CN: [3aS-(3aa,4~,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid fumoric ocid mesa-2.3-dibromo- cis-1,3-dibenzyl- succinic ocid 2-axo-imidazolidine- 4.5-dicorboxylic ocid (1) Biotin B 247 1. Zn. CH3COOH CH,COOH 2.H2S. HCI I 0 0 magnesium bromide 1.3-dibenzyl-4-(3-ethoxy- propy1idene)-cis-perhydro- thieno[3,4-d]imidozol-2-one (N) HBr, CH3COOH .v 1. silver D-comphorsulfonote. - AgBr 2. seporotion of diostereorners by crystollizotion b 1,3-dibenzyl-2-0~0-3a,8b-cis-per- hydrathieno[l',2':l .2]thieno[3.4-dl- imidozolium bromide (V) diethyl rnalonate 0 Biotin rnolonic acid diethyl ester 248 B Biotin cyclo- cis-1.3-dibenzyl-2-0x0- hexonol imidazolidine-4.5-dicorboxylic acid rnonocyclohexyl ester 4. H2, Raney-Ni 1. potassium thioacetote magnesium chloride 0-CH, (3oS)-1,3-dibenzyl-4t-(3- rnethoxypropyl)-(3or.60~)- tetrohydrothieno[3,4-dl- imidozol-2-one (VIII) 1. HBr Reference(s): US 2 489 232 (Roche; 1949; appl. 1946). US 2 489 233 (Roche; 1949; appl. 1947). US 2 489 234 (Roche; 1949; appl. 1947). US 2 489 235 (Roche; 1949; appl. 1947). US 2 489 236 (Roche; 1949; appl. 1947). US 2 489 237 (Roche; 1949; appl. 1948): US 2 489 238 (Roche; 1949; appl. 1948). US 2 5 19 720 (Roche; 1950; appl. 1948). US 3 740 416 (Roche; 1973; CH-prior. 29.1 1.1969). newer syntheses: DAS 2 331 244 (Sumitomo; appl. 19.6.1973; J-prior. 22.6.1972, 23.3.1973). DAS 2 534 962 (Teikoku; appl. 5.8.1975; J-prior. 5.8.1974, 6.8.1974, 8.8.1974). DOS 2 730 341 (Roche; appl. 5.7.1977; USA-prior. 12.7.1976). DOS 2 807 200 (Roche; appl. 20.2.1978; USA-prior. 23.2.1977). US 4 054 740 (Roche; 18.10.1977; prior. 24.12.1974, 5.9.1975). US 4 130 712 (Roche; 19.12.1978; prior. 12.7.1976, 17.6.1977). US 4 130 713 (Roche; 19.12.1978; prior. 5.8.1977). Lavielle, S. et al.: J. Am. Chem. Soc. (JACSAT) 100, 1558 (1978). Formrdation(s): amp. 0.5 mg, 5 mg; cps. 0.06 mg, 0.1 mg; drg. 0.15 mg, 0.5 mg; tabl. 5 mg, 10 mg Trade Name(s): D: Bio-H-Tin (Engelfried & Deacura (Dermapharm) Polybion (Merck)-comb. Bartel) Mediobiotin (Medopharm) Rombellin (Simons) Brodermatin (Engelfried & Multibionta (Merck)-comb. numerous combination Bartel) Piorin (Roche Nicholas) preparations Biperidene B 249 F: Alvityl (Solvay Pharma)- comb. Azedavit (Whitehall)- comb. Azinc complexe (Arkopharrna)-comb. Berocca (Nicholas) Biotine (Roche) Cemtvit (BaxtersaIClintel Parenttra1)-comb. ~ltvit Vitamine B9 (Nicholas)-comb. Lofenalac (Bristol-Myers Squihb)-comb. GB: Plenyl (0berlin)-comb. Soluvit (Pharmacia & I: Upjohn)-comb. Supradyne (Roche J: Nicholas)-comb. USA: Survitine (Roche Nicholas)-comb. Vivamyne (Whitehall)- comb. generics Ketovite (Paines & Byrne)- comb. Biodermatin (Lafare) Diathymil (Dermalife) Havita (Kakenyaku) Mega-B (Arco) Megadose (Arco) combination preparations Biperidene ATC: N04AA Use: antiparkinsonian RN: 514-65-8 MF: C21H2,N0 MW: 31 1.47 EINECS: 208-184-6 LD,,: 56 rnglkg (M, i.v.); 530 mgfkg (M, p.0.); 750 mglkg (R, p.0.); 340 mgkg (dog, p.0.) CN: a-bicyclo[2.2.1]hept-5-en-2-yl-a-phenyl-l-piperidinepropanol hydrochloride RN: 1235-82-1 MF: C2,HBN0. HCl MW: 347.93 EINECS: 214-976-2 LD,; 56 mglkg (M, i.v.); 530 mgkg (M, p.0.); 750 mgkg (R, p.0.); 340 mgkg (dog, p.0.) lactate (1:l) RN: 7085-45-2 MF: C,,H,,NO . C3H60, MW: 401.55 EINECS: 230-388-9 LD,o: 61 mglkg (M, i .v.) acetophenone poroform- piperidine 3-piperidino- aldehyde propiophenone (I) hept-5-en-2-yl- Biperidene magnesium chloride cyclo- methyl 2-ocetyl- 2-(3-piperidinopropiany1)- pentadiene vinyl ketone 5-norbornene 5-norbornene (U) 250 B Bisacodyl phenylmagnesium bromide Reference(s): US 2 789 110 (Knoll; 1957; D-prior. 1953). DE 1 005 067 (Knoll; appl. 1953). Formulation(s): amp. 5 mglml; powder 1 YO; S. r. drg. 4 mg; tabl. 2 rng Trade Narne(s): D: Akineton (Knoll) GB: Akineton (Abbott); wfm J: Akineton (Dainippon) Desiperiden (Desitin) I: Akineton (Ravizza; as Tasmofin (Yoshitomi) Norakin (Neuro Hexal) chloride) Tasmolin (Yoshitomi) F: Akineton retard (Knoll) Akineton (Knoll; as lactate) USA: Akineton (Knoll Labs.) Bisacodyl ATC: A06AB02; A06AG02 Use: laxative RN: 603-50-9 MF: C22HI,N0, MW: 361.40 EINECS: 210-044-4 LD,,: 17.5 glkg (M, p.0.); . . 4.32 glkg (R, p.0.); r 15 glkg (dog, p.0.) CN: 4,4'-(2-pyridinylmethylene)bis[phenol] diacetate (ester) pyridine-2- phenol 2-(4.4'-dihydroxy- carboxaldehyde benzhydry1)pyridine Reference(s): DE 951 987 (Thomae; appl. 1952). US 2 764 590 (Thomae; 1956; D-prior. 1952). alternative synthesis: DE 951 988 (Thomae; appl. 1952). Trade Name(s): D: Agaroletten (Warner- Drix (Hermes) Bisacodyl I ~imbert) Dulcolax (Boehringer Ing.) Bekunis (roha) Florisan (Boehringer Ing.) Bisco-Zifron extra stark Laxagetten (ct- (Biscova) Arzneimittel) Biscu (Biscova) Laxanin (Schwarzhaupt) Darmol (Omegin) Laxanin N (Schwarzhaupt) Laxbene (Merckle) Laxoberal (Boehringer Ing.) Mandrolax (Dolorgiet) Marienbader (RIAM) Mediolax (Medice) Pyrilax (Berlin-Chemie) . RN: 3463 3-3 4-6 MF: C,,H,,F,O, MW: 292.33 CN: (R*,S* )-4 ,4&apos ;-( 1-ethyl-2-methyl-l,2-ethanediyl)bis[2-fluorophenol] 3-chloro- 2- trans-2.3-bis(3-fluora-4-methoxy- pentanone phenyl )-2 -pentene. 20 0-3 9 9-3 CN: [3aS-(3aa,4~,6aa)]-hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid fumoric ocid mesa-2.3-dibromo- cis-1,3-dibenzyl- succinic ocid 2-axo-imidazolidine- 4.5-dicorboxylic. N-(4-cyano-3-trifluorcmethylphenyl )- 3-( 4-fluorophenylsuIfony1 )-2 -hydroxy- 2-methylpropionomide (N) J-chloroper- benzoic acid (V) I Bicolutomide I methocryloyl chloride 4'-cyono-3'-trifluoro