Aminocaproic acid A 9 1 5-0x0-l0,ll-dihydro- 5-hydroxy- l0,l 1 - 5-chloro-l0,l 1 -dihydro-5H- SH-dibenzo[o,d]cyclo- dihydro-5H-di- dibenzo[a,d]cyclohep(ene (I) heptene benzo[a,d]cycloheptene ethyl 7-aminoheptanoote I Amineptine I Reference (s): DOS 2 01 1 806 (Science Union; appl. 12.3.1970; GB-P. 27.3.1969). US 3 758 528 (Science Union; 11.9.1973; appl. 13.3.1970). US 3 821 249 (Science Union; 28.6.1974; prior. 13.3.1970, 30.10.1972). Fomularion(s): tabl. 100 mg (as hydrochloride) Trade Name(s): F: Survector (Euthtrapic; 1: Maneon (Poli; 1983) 1978); wfm 1999 Survector (Stroder; 1983) Aminocaproic acid ATC: B02AAO1 (Acide aminocaproique; Epsilcapramin) Use: antifibrinolytic, plasmin inhibitor RN: 60-32-2 MF: C6H,,N02 MW: 131.18 EINECS: 200-469-3 LD,,: 4900 mgkg (M, i.v.); 14.3 glkg (M, p.0.); 3300 mgkg (R, i.v.); >7 glkg (dog, p.0.) CN: 6-aminohexanoic acid &-caproloctom I Aminocaproic acid US 2 453 234 (American Enka Corp.; 1948; NL-prior. 1946). Formularion(s): inj. flask 250 mglml; syrup 25 %; tabl. 500 mg Trade Nanle(s): D: Epsilon-Aminocapronsaure F: Hexalense (Leurquin) Resplamin (Kyorin) "Roche" (Roche); wfm I: Caprolisin (Malesci) USA: Amicar (Immunex) Epsilon-Tachostypan J: Capusumine (Nichiiko) (Hormon-Chemie)-comb.; Hemotin (Hokuriku) wfm Ipsilon (Daiichi) 92 A Aminoglutethimide Aminoglutethimide ATC: JO4AAO1 Use: antineoplastic (aromatase inhibitor) RN: 125-84-8 MF: C,,H,,N,O, MW: 232.28 EINECS: 204-756-4 LD,,: 625 mglkg (M, i.p.) CN: 3-(4-aminopheny1)-3-ethyl-2,6-piperidinedione NO2 glutethimide 2-(4-nitropheny1)- Aminoglutethimide (q v.) 2-ethylglutorimide (I) methyl ocrylote " l.= 2-phenyl- butyronitrile 2-(4-nitropheny1)- butyronitrile Reference(s): US 2 848 455 (Ciba; 1958; CH-prior. 1955). racemate resolution: Finch, N. et al.: Experientia (EXPEAM) 31, 1002 (1975). Formulation(s): tabl. 250 mg Trade Name(s): D: Orimeten (Novartis F: Orimkthe (Novartis) USA: Cytadren (Novartis) Pharma) GB: Orimeten (Novartis) Rodazol (Novartis Pharma) I: Orimeten (Novartis) Aminophenazone (Amidophenazon; Amidopyrin; Aminopyrine) ATC: N02BB03 Use: analgesic, antipyretic, anti- inflammatory RN: 58-15-1 MF: C,,H,,N,O MW: 231.30 EINECS: 200-365-8 LDS,,: 78 mg/kg (M, i.v.); 350 mglkg (M, p.0.); 98 mglkg (R, i.v.); 285 mglkg (R, p.0.); 121 mglkg (dog, i.v.); 220 mglkg (dog, p.0.) CN: 4-(dimethylamino)-l,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one Aminopromazine A 93 ascorbate RN: 23635-43-0 MF: C,,H,,N,O . C6H80, MW: 407.42 ethyl acetoacetate phenylhydrazine . dimethyl sulfote (I) 4-amino-2,3-dimethyl- I Aminophenarone I 1 -phenyl-5-~3- pyrazolone Referencefs): DRP 193 632 (E. Scheitlin; 1907). Ehrhart, Ruschig I, 171. Formulation(s): suppos. 200 mg, 500 mg; tabl. 100 mg, 300 mg Trade Name(s): D: Compretten (Cascan); wfm Pyramidon (Hoechst); wfm numerous combination Dimametten (Hormosan); I: Farmidone (Farmitalia) preparations wfm Fugantil (Ghimas) J: Neophyllin (Nippon Eisai) Aminopromazine (Proquamezine) Use: antispasmodic RN: 58-37-7 MF: C,,H,,N,S MW: 327.50 EINECS: 200-378-9 CN: N,N,Ar,Ar-tetramethy1-3-(1OH-phenothiazin-lO-yl)-l,2-propanediamine fumarate (2:l) RN: 3688-62-8 MF: C1yHZSN3S. 1/2C4H404 MW: 771.06 EINECS: 222-987-9 a:?O phenothiazine 3. fract. crystallization of the hydrochlorides 1. sodium amide 2. 1,3-bis(dimethy1omino)- 2-chloropropane Arninopromazine 94 A D-Aminosalicvlic acid Reference(s): GB 800 635 (Rh6ne-Poulenc; appl. 1954). DE 1 034 637 (RhGne-Poulenc; appl. 1955; F-prior. 1954). Trade Name(s): D: Lorusil (Bayer); wfm F: Lispamol (Specia); wfm p-Aminosalicylic acid (Aminosalylum; PAS) ATC: J04AAOI Use: tuberculostatic RN: 65-49-6 MF: C7H7N03 MW: 153.14 EINECS: 200-613-5 LD,,: 3898 mgkg (M, i.v.); 4 glkg (M, p.0.) CN: 4-amino-2-hydroxybenzoic acid calcium salt (2:l) RN: 133- 15-3 MF: C14H12CaN206 MW: 344.34 EINECS: 205-095-4 LD,,,: 6500 mgkg (M, p.0.) monosodium salt RN: 133- 10-8 MF: C,H,NNaO? MW: 175.12 EINECS: 205-091 -2 qoH + CO, KHC03. 5- 10 atm NH2 3-amino- carbon phenol dioxide Reference(s): US 2 540 104 (Parke Davis; 195 1 ; prior. 1949). purijication: US 2 844 625 (Miles, 1958; appl. 1954). NH2 p-Aminosalicylic ocid Fo~-mulation(s): vial -1 3.49 g (as monosodium salt) Trade Name(s): D: Pas-Fatol N (Fatol) GB: Asacol (SmithKline F: B-PAS (Salvoxyl-Wander); Beecham) Salf-Pas (Salf; as sodium salt) wfm Pentasal (Yamanouchi) J: PAS Calcium (Sumitomo); PAS Elbiol Salofalk (Thames) wfm (Pharmacotechnie); wfm I: Eupasal sodico (Bieffe Sanpas Cal. (Sankyo); wfm Medital; as sodium salt) USA: Paser (Jacobus) Amiodarone ATC: COlBDOl Use: antiarrhythmic RN: 1951-25-3 MF: C25H2912N03 MW: 645.32 EINECS: 217-772-1 LD,,,: 178mg/kg(M,i.v.);>4g/kg(M,p.o.) CN: (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone hydrochloride RN: 19774-82-4 MF: C2,H2,I2NO, . HCI MW: 681.78 0 0 a+ doLcH3 H2N-NHl 0 H20 wCH3 H3C hydrazine ' hydrate benzofuron butyric anhydride 2-butyrylbenzofuran 2-butylbenzofuran (I) I 0. CH3 hydrochloride CH3 4-rnethoxy- 2-butyl-3-(4-methoxy- 2-butyl-3-(4-hydroxy- benzoyl chloride benzoy1)-benzofuron benzoyl)-benzofuron (11) 2-butyI-3-(4-hydroxy- 3,5-diiado-benzayl). benzofuron (C"3 "a Cti-0th ~~''~~3 \ OH P-diethylornina- ethyl chloride I Arniodarone I /'o - I Reference(s): FR 1 339 389 (Labaz; appl. 22.11.1962). US 3 248 401 (Labaz; 26.4.1966; prior. 24.1 1.1961). 2-butylbenzofuran: Buu-Hoi', N.P. et al.: J. Chem. Soc. (JCSOA9) 1964, 173. Formulation(s): inj. sol. 150 mgl3ml; tabl. 200 mg Trade Name(s): D: Cordarex (Sanofi F: Cordarone (Sanofi I: Winthrop) Winthrop) Tachydaron (ASTA Medica GB: Cordarone X (Sanofi USA: AWD) Winthrop) Amiodar (Midy) Cordarone (Sigma-Tau) Cordarone (Wyeth-Ayerst; as hydrochloride) Amiphenazole ATC: R07A Use: respiratory stimulant, morphine antagonist, antidote (barbiturate poisonings) RN: 490-55-1 MF: C9HyN,S MW: 191.26 EINECS: 207-713-8 LD,,,: 400 mglkg (M, p.0.) CN: 5-phenyl-2,4-thiazolediamine monohy drochloride RN: 942-31-4 MF: C,HyN3S. HC1 MW: 227.72 EINECS: 213-389-9 LD,,,: 372 mglkg (M, p.0.) thiourea a-bromo- phenylocetonitrile Reference(s): Davis, W. et al.: J. Chem. Soc. (JSCOA9) 1955, 3491. Chase, B.H. et al.: J. Chem. Soc. (JSCOA9) 1955,4443. Formulation(s): inj. flask 150 mg Trade Narne(s): 9 /+NH, N H2N Arniphenozole , . D: Daptazile 100 (Nicholas); Daptazile Injektion GB: wfm (Nicholas); wfm Daptazole (Nicholas); wfm Amitriptyline ATC: N06AA09 Use: antidepressant RN: 50-48-6 MF: C,,H,,N MW: 277.41 EINECS: 200-041-6 LD,,,: 16mgkg(M,i.v.); 140mg/kg(M,p.o.); 320 mgtkg (R, p.0.) CN: 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-l-propanamine hydrochloride RN: 549-18-8 MF: Cz0H2,N . HC1 MW: 313.87 EINECS: 208-964-6 LDSo: 21 mgkg (M, i.v.); 140 mgkg (M, p.0.); 14 mgkg (R, i.v.); 240 mgkg (R, p.0.); >27 mgkg (dog, i.v.) CH3 dibenzosuberone (I) 3-dimcthylominopropyl- 5-(3-dimethylominopropyl)- magnesium chloride l0,ll -dihydro-5H- I Amitriptyline Amitriptylinoxide A 97 I11 cyclopropyl- magnesium bromide 5-(3-bromopropylidene)- 10,l 1-dihydro-5H- dibenzo[o.d]cycloheptene (IU) CH3 dimethylomine Reference(s): a GB 858 187 (Hoffmann- .La Roche; appl. 24.3.1959; CH-prior. 3.4.1958). DE 1 109 166 (Hoffmann-La Roche; appl. 16.3.1959; CH-prior. 3.4.1958). BE 584 061 (Merck & Co.; appl. 27.10.1959; USA-prior. 31.10.1958). BE 609 095 (Kefalas AIS; appl. 12.10.1961; DK-prior. 12.10.1960). b Hoffsommer, R.D. et al.: J. Org. Chem. (JOCEAH) 27,4134 (1962). alternative synthesis: DAS 1 468 138 (Kefalas; appl. 12.3.1963; GB-prior. 23.3.1962,9.11.1962). US 3 205 264 (Merck & Co.; 7.9.1965; appl. 15.6.1962). Formulation(s): amp. 56.6 mg; f. c. tabl. 10 mg, 25 mg, 50 mg; drg. 11.32 mg, 28.3 mg; drops 40 mg/l ml; inj. 50 mg/2 ml; tabl. 25 mg, 50 mg (as hydrochloride) Trade Name(s): D: Amineurin (Neuro Hexal) I: Limbatril (ICN) Saroten (Bayer Vital) F: Elavil (Merck Sharp & Dohme-Chibret) Laroxyl (Roche) GB: Lentizol (Parke Davis) Triptafen (Goldshield)- comb. Tryptizol (Morson) Adepril (Lepetit) Amilit-ifi (IFI) Amitript (Formulario Naz.) Diapatol (Teofarma)-comb. Laroxyl (Roche) Limbitryl (Roche)-comb. Sedans (Ganassini)-comb. Triptizol (Merck Sharp & Dohme) combination preparations J: Tryptanol (Merck-Banyu; as hydrochloride) USA: Elavil (Zeneca; as hydrochloride) Etrafon (Schering) Limbitrol (Roche Products; as hydrochloride) Triavil (Merck; as hydrochloride) generics Amitriptylinoxide ATC: N06AA09 Use: antidepressant RN: 4317-14-0 MF: C,,H,,NO MW: 293.41 LD,,: 320 mg/kg (M, i.p.); 87 mglkg (M, i.v.); 330 mg/kg (M, p.0.); 120 mgkg (R, i.p.); 25 mg/kg (R, i.v.); 1800 mg/kg (R, p.0.); 330-460 mglkg (rabbit, p.0.); 330 mglkg (dog, p.0.) CN: 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-l-propanamine N-oxide 98 A Amixetrine ornitriptyline I Arnitriptylinoxide pH3 + HO-N, Br CH3 5-(3- bromopropy1idene)- N,N-dimethyl- 10.1 1 -dihydro-5H- hydroxylamine dibenzo[o.d]cycloheptene (cf. ornitriptyline synthesis) Reference(s): DE 1 243 180 (Dumex; appl. 15.2.1964; GB-prior. 20.2.1963). FR-M 3 222 (Dumex; appl. 20.2.1964; GB-prior. 20.2.1963). NL-appl. 6 51 1 947 (Merck & Co., appl. 14.9.1965; USA-prior. 14.9 1964). Fortnulation(s): tabl. 30 mg, 60 mg, 90 mg, 120 mg Trade Narne(s): D: Equilibrin (Rh6ne-Poulenc Rorer) Amixetrine ATC: N06A; R03BB Use: anticholinergic, antidepressant, antispasmodic RN: 24622-72-8 MF: C,,H,NO MW: 261.41 CN: 1-(2-(3-methy1butoxy)-2-phenylethyllpyrrolidine hydrochloride RN: 24622-52-4 MF: C,,H,,NO. HCl MW: 297.87 EINECS: 246-365-1 -CH, tert-butyl - codCH3 pyrrolidine hypobrornite Br styrene isoomyl alcohol a-isoomyloxy- phenethyl bromide Reference(s): DOS 1 81 1 767 (Mauvernay; appl. 29.1 1.1968; F-prior. 15.12.1967). Amixetrine Formulation(s): tabl. 50 mg Trade Name(s): F: Somagest (Riom); wfm Amlexanox A 99 Amlexanox (AA-673) ATC: R03DXO I ; R06AX Use: antiallergic, antiasthmatic RN. 68302-57-8 MF: CI,H,,N20, MW: 198.30 LD,: 2320 mgkg (M. p.a ): 10 @g (R. p.0.) CN. 2-amino-7-( I-methylethyl)-5-0x0-SH-[I ~henzopyrano[2,3-b]pyr1dine-3-carhc~xyl~c ac~d 2-hydroxy-5-isopropyl- dimelhyl- 6-isopropy-4-0x0- acetophenone formornide 4H-1 -benzopyran-3- corboxaldehyde (I) n NHIOH OVNH , DMF 1 - H3C hydroxylomine CN morpholinc . dimethyl- CHO CH3 * formornnde . CH3 0 6-ixopropyl-4-oro- 2-amino-6-isopropyl- 4H- I- benropyron- 4-0x0-4H- 1-bentopyron- 3-corbonitrila 3-carboxoldehyde (D) ethyl cyonoacetote I Amlexanox 1. pipcridinc 0 2. H2S0, + Ncdo~CH3 F Refcrerrrr(s): DOS 2 809 720 (Takeda: appl. 7.3.1978; J-prior. 8.3.1977,20.12.1977) US 4 143 042 (Takeda; 6.3.1979; J-prior. 8.3.1977, 20.12.1977). CIS 4 255 576 (Takcda; 10.3.1981; J-prior. 8.3.1977, 10.12.1977). US 4 299 963 (Takcda; 10.1 1.1981; J-prior. 8.3.1977. 10.12.1977). Nohara, A. ct al.: J. Mcd. Chcrn. (JMCMAR) 28.559 (1985). sydiesis of6-isopropyl-4H- 1 -benxopyran-3-carbonitri1e: H3C aNH2 COOH CHJ 0 US 3 896 1 14 (Takeda Chemical Ind.; appl. 22.7.1975; J-prior. 12.4.1972, 14.4.1072). DE 2 3 17 898 (Takeda Chemical Ind.; appl. 25.10.1973; J-prior. 12.4.1972). Funn~rlr~rion{s): cream 5 %o; tabl. 100 mp Trade N(~me(a ): J: Solfa (Takeda: 1989) USA: Aphthasol (Block Drug Company) Amlodipine ATC: COZDE: CORCAOI Use: calcium antagon~st. antianginal. antlhypcrtensivc RN: 88150-42-9 MF: C,H,,C1N20, MW: 408.88 CN: 2-i(2-aniinoethoxy )methyl]-4-i2-c21lorophenyl)- 1,4-di hydro-6-methyl-3.5-pyridinedicarboxylic acid 3- ethyl 5-methyl ester 100 A Amlodipine rnaleate (1:l) RN: 88150-47-4 MF: C20H,5ClN20, . C4H404 MW: 524.95 ethyl 4-chloro- ocetooctote CHO +&I+ 2-chlora- benzaldehyde methyl 3-omino- crotonate ethyl 4-(2-ozidoethoxy) ocetoocetote (1) 3-ethyl 5-methyl 2-[(2-ozido- ethoxy)methyl]-4-(2-chloropheny1)- 1.4-dihydro-6-methyl-3.5- pyridinedicarbaxylote (U) Arnlodipine Reference(s): EP 89 167 (Pfizer; appl. 8.3.1983; GB-prior. 11.3.1982). EP 599 220 (Lek; appl. 19.11.1993; SI-prior. 26.1 1.1992). CA 2 188 071 (Apotex; appl. 17.10.1996; NZ-prior. 1.1 1 .l995). besylate salt: EP 244 944 (Pfizer; appl. 31.3.1987; GB-prior. 4.4.1986). racemate resolution: . EP 331 315 (Pfizer; appl. 16.2.1989; GB-prior. 27.2.1988). Arrowsmith, J.E. et al.: J. Med. Chem. (JMCMAR) 29, 1696 (1986). combination with ACE-inhibitors: WO 9 628 185 (Pfizer; appl. 26.2.1996; USA-prior. 16.3.1 995). Formulation(s): cps. 5 mg, 15 mg, 20 mg; tabl. 2.5 mg, 5 mg, 10 mg Trade Name(s): D: Norvasc (Mack, Illert; I: Antacal (Errekappa J: Amlodin (Sumitomo) Pfizer) Euroter.; 1991) Norvasc (Pfizer) F: Amlor (Pfizer) Monopina (Bioindustria; USA: Lotrel (Novartis) GB: Istin (Pfizer; 1990) 1991) Norvasc (Pfizer; 1991) Norvasc (Pfizer; 1990) . hydrochloride CH3 4-rnethoxy- 2-butyl- 3-( 4-methoxy- 2-butyl- 3-( 4-hydroxy- benzoyl chloride benzoy1)-benzofuron benzoyl)-benzofuron (11) 2-butyI- 3-( 4-hydroxy- 3,5-diiado-benzayl). benzofuron. 1 5-0 x0-l0,ll-dihydro- 5-hydroxy- l0,l 1 - 5-chloro-l0,l 1 -dihydro-5H- SH-dibenzo[o,d]cyclo- dihydro-5H-di- dibenzo[a,d]cyclohep(ene (I) heptene benzo[a,d]cycloheptene ethyl 7-aminoheptanoote. dimethyl- CHO CH3 * formornnde . CH3 0 6-ixopropyl-4-oro- 2-amino-6-isopropyl- 4H- I- benropyron- 4-0 x 0-4 H- 1-bentopyron- 3-corbonitrila 3-carboxoldehyde (D) ethyl cyonoacetote I