Alprazolam A 71 1. POCI, 2. H H C"~*CH n; 1. phosphorus oxychloride 2. dipropylornine H3C-N7,- CH3 Reference(s): EP 50 563 (Synthelabo; appl. 15.10.1981 ; F-prior. 22.10.1980). US 4 382 938 (Synthelabo; 10.5.1983; F-prior. 22.10.1980). US 4460 592 (Synthelabo; 17.7.1984; F-prior. 22.10.1980). Formulation(s): tabl. 50 mg Trade Name(s): F: Anaxyl (SynthClabo; 1991); wfm Alprazolam ATC: N05BA12 Use: tranquilizer RN: 28981-97-7 MF: C,,H,,C1N4 MW: 308.77 EINECS: 249-349-2 LD,,: 770 mgkg (M, p.0.); 1220 mglkg (R, p.0.) CN: 8-chloro- 1 -methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][ 1,4]benzodiazepine hydrazine hydrote tricthyi orthoocetote 7-chloro-1 -methyl-5. phenyl[l.2.4]tn'ozolo- [4,3-alquinoiine (I) H3C'7s~\ No104, Ru02 ocetone. H20 2.PBr3, CHCI, I sodium periodole' CI 1. formaldehyde ' CI ruthenium dioxide 2. phosphorus(ll1) bromide NH,. THF, CH30H I1 Alprozoiarn 1 72 A Alprenolol benzoyl 2-omino-5-chloro chloride benzophenone '4'10 + phosphorus(V) sulfide pyridine + 111 ethyl glycinote hydrochloride CH3-CO-NH-NH2 , butanol - acetohydrazide 2-0x0-2.3-dihydro-lH- 2-thioxo-2,3-dihydro- 7-chloro-5-phenyl-3H- 1.4-benzodiazepine (111) 1 H- 1 -4-benzodiazepine l,4-benzadiozepine . (IV) 25OoC N b Alprazolom Reference(s): US 3 987 052 (Upjohn; 19.10.1976; appl. 29.10.1969; USA-prior. 17.3.1969). US 3 980 789 (Upjohn; 14.9.1976; appl. 19.6.1972; USA-prior. 29.3.1971). DE 1 955 349 (Takeda; D-prior. 4.1 1.1969). GB 1 298 364 (Upjohn; GB-prior. 27.10.1969). a DOS 2 203 782 (Upjohn; appl. 27.1.1972; USA-prior. 9.2.1971). US 3 709 898 (Upjohn; 9.1.1973; prior. 9.2.1971). US 3 781 289 (Upjohn; 25.12.1973; prior. 1 1.5.1972). b DOS 2 012 190 (Upjohn; appl. 14.3.1970; USA-prior. 17.3.1969). Formulation(s): tabl. 0.25 mg, 0.5 mg, 1 mg, 1 g Trade Name(s): D: Cassadan O,25/0,5/l (ASTA F: Medica AWD) GB : Tafil0,5/1,0 Tabletten (Pharmacia & Upjohn; I: 1984) Xanax (Pharmacia & Upjohn) Alprenolol Xanax (Upjohn; 1984) Xanax (Upjohn; 1985) Xanax (Pharmacia & J: Constan (Takeda; 1984) Upjohn; 1983) Solanax (Upjohn- Frontal (UCM) Sumitomo; 1984) Mialin (Biomedica USA: Xanax (Pharmacia & Foscama) Upjohn; 1981) Valeans (Valeas) ATC: C07AAO1 Use: beta blocking agent RN: 13655-52-2 MF: C,,H,,NO, MW: 249.35 EINECS: 237-140-9 LD,,,: 20 mgkg (M, i.v.) CN: l-[(l-methylethyl)amino]-3-[2-(2-propenyl)phenoxy]-2-propanol Altizide A 73 hydrochloride RN: 13707-88-5 MF: C15H2,N02. HCI MW: 285.82 EINECS: 237-244-4 LDso: 29 mglkg (M, i.v.); 184 mgkg (M, p.0.); 17 mgkg (R, i.v.); 590 mglkg (R, p.0.); 18 mgkg (dog, i.v.); 383 mgkg (dog, p.0.) 2-allylphenol epichlorohydrin 1 -(2-ollylphenoxy)- 2.3-epoxypropone (I) Reference(s): US 3 466 376 (AB Hassle; 9.9.1969; prior. 18.1.1966, 17.6.1966). Brandstrom, A.: Acta Pharm. Suec. (APSXAS) 1966,303. isopropylornine 2-allylphenol by rearrangement of ally1 phenyl ether: DOS 2 746 002 (Firestone; appl. 13.10.1977; USA-prior. 18.10.1976). Alprenolol Formulation(s): cps. I0 mg, 20 mg, 40 mg, 50 mg; lyo. for inf. 42.6 mg; tabl. 200 mg Trade Name(s): D: Aptin-Duriles (Astra) J: Apllobal (Fujisawa; as hydrochloride) Altizide (Althiazide) ATC: C03EAO 1 ; C03EA04 Use: diuretic, antihypertensive RN: 5588-16-9 MF: C,,H14C1N304S3 MW: 383.90 EINECS: 226-994-8 CN: 6-chloro-3,4-dihydro-3-[(2-propenylthio)methy1]-2H- 1,2,4-benzothiadiazine-7-sulfonamide 1, l-dioxide 6-amino-4-chloro- chloroocetaldehyde benzene-1.3-disulfamide o,\ /p I + %A CH, NoOH 1 H2N-02saiNH CI Lsa'CHq ally1 rnercapton I H I I Altizide I 74 A Altretamine Reference(s): GB 902 658 (Pfizer; appl. 10.1.1961; USA-prior. 27.9.1960). Formulation(s): cps. 0.25 mg, 0.5 mg; drops 1 mg; sol. 0.1 mglml; tabl. 0.25 mg, 0.5 mg, 1 mg, 2 mg Trade Name(s): F: Aldactazine (Momanto)- Prinactizide (Dakota). I: Aldatense (SPA)-comb.; comb. comb. wfm Practazin (Cardel)-comb. Spiroctazine (Boehringer USA: Aldactazide (Searle)- Mannh.)-comb. comb.; wfm Altretamine (Hexamethylmelamine) ATC: LOlXXO3 Use: antineoplastic RN: 645-05-6 MF: C,H,,N, MW: 210.29 EINECS: 211-428-4 LD,,: 350 mglkg (R, p.0.) CN: N,N,N,N,N',N'-hexamethyl-1,3,5-triazine-2,4,6-triamine hydrochloride RN: 15468-34-5 MF: C,Hl,N, , xHC1 MW: unspecified LD,,: 100 mglkg (M, i.v.) melamine formaldehyde hexamethylolmelamine hexamethyl ether (I) H3c/O\ f O'cH, 0 N N,N 0 H3c' - \[; Y - ' Hz, Raney-Ni CH3 . NyN I Altretamine 7~3 y3 N N N, C CH3 N yN CI N CI N N N, YY + 11 , NaOH YH3 - H~C/ Y Y CH3 , NyN NH N yN C I H,C/ CI cyonuric dimethyl- 2-chlaro-4.6-bis- chloride omine (11) (dimethylomino)- 1.3.5-triazine Altretamine rn a DE 1 240 870 (Cassella; appl. 17.1 1.1965). b Gunduz, T.: Commun. Fac. Sci. Univ. Ankara, Ser. B: Chim. (CAKBA9) 1569 (1968). Cumber, A.J.; Ross, W.C.J.: Chem Biol. Interact. (CBINA8) 17, 349 (1977). Alufibrate A 75 synthesis of hexamethylolmelamine hexamethyl ether: Gams, A. et al.: Helv. Chim. Acta (HCACAV) 24, 302 (1941). US 3 322 762 (Pittsburgh Plate Glass; 30.5.1967; prior. 27.2.1962; 8.4.1964). Formulafion(s): cps. 50 mg, 100 mg Trade Name(s): D: Hexamethylmelamin F: Hexastat (Roger Bellon); I: Hexastat (RhGne-Poulenc (RhGne-Poulenc); wfm wfm Rorer) GB: Hexalen (Speywood) USA: Hexalen (US. Bioscience) Alufibrate (Aluminium clofibrate) ATC: COIAB03 Use: cholesterol depressant RN: 2481 8-79-9 MF: C,,H,,AlCl,O, MW: 471.27 EINECS: 246-477-0 CN: bis[2-(4-chlorophenoxy-~O)-2-methylpropanoato-~O]hydroxyaluminum Reference(s): GB 860 303 (ICI; appl. 20.6.1958). clofibric acid aluminum Fortnulation(s): tabl. 500 mg Alufibrate Trade Name(s): D: Atherolipin (Schwarz); F: Athtrolip (Millot-Solac); wfm wfm (cf. clafibrate ethylate synthesis) Aluminum nicotinate ATC: CIOAD04 Use: antihyperlipidemic, vasodilator (peripheral) RN: 1976-28-9 MF: C,,H,,AlN,O, MW: 393.29 EINECS: 217-832-7 CN: 3-pyridinecarboxylic acid aluminum salt Reference(s): US 2 970 082 (Walker Labs.; 3 1 .I. 1961; appl. 7.10.1958). nicotinic acid aluminum I hydroxide Aluminum nicatinate 76 A Alverine Formulation(s): tabl. 125 mg Trade Name(s): USA: Nicalex (Merrell-National); wfm Alverine (Dipropyline; Fenpropamine) ATC: A03AX08 Use: antispasmodic RN: 150-59-4 MF: CmH,N MW: 281.44 EINECS: 205-763-5 CN: N-ethyl-N-(3-phenylpropy1)benzenepropanamine citrate (1:l) RN: 5560-59-8 MF: C2,H2,N . C6H807 MW: 473.57 EINECS: 226-929-3 3-phenylpropyl ethyl- chloride ornine (1) rYT CH3 Alverine WCH0 Hz, Pt-BoS04 + 1 cinnornoldehyde Refl.rence(s): a Kulz, E et al.: Ber. Dtsch. Chem. Ges. (BDCGAS) 72,2161 (1939) b Stuhmer, W.; Elbrachter, E A.: Arch. Pharm. Ber. Dtsch. Pharm. Ges. (APBDAJ) 287, 139 (1954). Formulation(s): inj. sol. 40 mgl2 ml; suppos. 80 mg; tabl. 40 mg Trade Name(s): D: Spasmocol (Norgine)- Schoum comprimCs Spasmonal (Norgine; as comb.; wfm (Pharmysikne)-comb. citrate) F: Hepatoum (Hepatourn)- SpasmavCrine (ThCraplix) I: Profenil (Ipti); wfm comb. SpasmavCrine suppos. Spasmaverine (Roger MCttospasmyl (Mayoly- (ThCrap1ix)-comb. Bellon); wfm Spind1er)-comb. GB: Alvercol (Norgine; as USA: Spacolin (Philips Roxane); citrate)-comb. wfm Amantadine ATC: JOSAC;NO4BBOl Use: antiparkinsonian, antiviral RN: 768-94-5 MF: C,,H,,N MW: 151.25 EINECS: 212-201-2 LDso: 700 mglkg (M, p.0.); 900 mglkg (R, p.0.) CN: tricyclo[3.3.1. 13-7]decan-l -amine Ambazone A 77 hydrochloride RN: 665-66-7 MF: C,,H,,N. HCI MW: 187.71 EINECS: 21 1-560-2 LD,,,: 95 mgkg (M, i.v.); 700 mglkg (M, p.0.); 90 mgkg (R, i.v.); 800 mglkg (R, p.0.); 37 mgkg (dog, i.v.) sulfate (2:l) RN: 31377-23-8 MF: CI,H17N. 112H2S04 MW: 400.58 EINECS: 250-604-5 - acetonitrite k-4 adamantone 1 -bromo- adamontone 1 -acetylarnino- Amontodine adornontane Reference(s): Stetter, H. et al.: Chern. Ber. (CHBEAM) 93, 226 (1960). US 3 310469 (Du Pont; 21.3.1967; prior. 28.8.1961, 15.4.1963,22.10.1963). synthesis front adamantane, HCN and H2S04: US 3 152 180 (Studiengesellschaft Kohle; 6.1 0.1964, D-prior. 25.8.1960). combination with rnolindone (antidepressant): US 4 148 896 (Du Pont; 10.4.1979; appl. 22.2.1978). Formulalion(s): f. c. tabl. 100 mg, 150 mg; cps. 100 mg; amp. 200 mgl500 ml (as sulfate); syrup 50 mg15 ml Trade Name(s): D: Amantadin (ratiopharm) GB: Symmetrel (Geigy; as J: Symmetrel (Fujisawa- PK-Merz (Merz & Co.) hydrochloride) Novartis) F: Mantadix (Du Pont) I: Mantadan (Boehringer USA: Symmetrel (Endo) Ing.) Ambaaone ATC: R02AAO1 Use: antiseptic, disinfectant (oral and pharyngeal chemotherapeutic), antineoplas tic RN: 539-21-9 MF: C,H,,N,S MW: 237.29 EINECS: 208-713-0 LDSi 1 glkg (M, p.0.); 750 mgtkg (R, p.0.) CN: 2-[4-[(aminoiminomethyl)hydrazono]-2.5-cyclohexadien-1-ylidene]hydrazinecarbothioamide monohydrate RN: 6011-12-7 MF: CnHlIN7S~H20 MW: 255.31 78 A Ambenonium chloride aminaguanidine p-benzo- p-benzoquinone quinone arnidinohydrazane Reference(s): DE 965 723 (Bayer; appl. 1953). Formulntion(s): tabl. 10 mg, I00 mg Trade Narne(s): D: Iversal (Bayer); wfm GB: Iversal (Bayer); wfm F: Iversal (Bayer); wfm I: Primar (Bayer); wfm Ambazone L Ambenonium chloride ATC: N07AA3O Use: cholinesterase inhibitor RN: 1 15-79-7 MF: C2,H42C14N,02 MW: 608.48 EINECS: 204-107-5 LD,,,: 1510 gkg (M, i.v.); 145 mglkg (M, p.0.); 2720 g/kg (R, i.v.); 18.5 mgkg (R, p.0.) CN: N, N'-[(I ,2-dioxo- l,2-ethanediyl)bis(imino-2,1-ethanediyl)]bis[2-chloro-N,N- diethylbenzenemethanaminium] dichloride hydroxide RN: 470-78-0 MF: C2,H,C12N404 MW: 571.59 N,N-diethyl- diethyl oxalate . N,N'-bis(2-diethylaminoethyl)- ethylenediomine oxamide (I) Reference(s): DE 1 024 517 (Sterling Drug; appl. 1954; USA-prior. 1953). US 3 096 373 (Sterling Drug; 2.7.1963; appl. 1956). Phillips, A.P.: J. Am. Chem. Soc. (JACSAT) 73,5822 (1951). 2-chlorabenzyl Ambenoniurn chloride chloride Ambroxol A 79 oxamide intermediate: US 2 438 200 (Du Pont; 1948; appl. 1946). Formulation(s): cps. 10 mg; tabl. 10 mg Trade Name(s): D: Mytelase Tabletten GB: Mytelase (Winthrop); wfm J: Mytelase (Winthrop- (Winthrop); wfm I: Mytelase (Winthrop); wfm Nippon Shoji) F: Mytelase (Sanofi Winthrop) USA: Mytelase (Winthrop); wfm Ambroxol ATC: RO5CB Use: expectorant RN: 18683-91-5 MF: C,,H,,Br,N,O MW: 378.1 1 EINECS: 242-500-3 LDS,,: 138 mglkg (M, i.v.); 2720 mglkg (M, p.0.); 13.4 g/kg (R, p.0.) CN: trans-4-[[(2-amino-3,5-dibromophenyl)methyl]amino]cyclohexanol poracetamol trans-4-met- trans-4-omina- (q. v.1 omidocyclohexona~ cyclohexanol (I) OH NaBH4 or HCOOH OHC Br NHZ NH2 NH2 2-amino-3.5- trans-4-(2-amino-3,5- dibromobenzoldehyde dibromobenzylidenamina)- Ambroxol I cyclohexanol . Reference(s): GB 1 178 034 (Boehnnger Ingelh.; appl. 10.5.1967; D-prior. 10.5.1966). US 3 536 713 (Boehringer Ingelh.; 27.10.1970; appl. 10.5.1967; S-prior. 10.5.1966). DE 1 593 579 (Thomae; appl. 10.5.1966). DOS 2 218 647 (Thomae; appl. 18.4.1972). DOS 2 223 193 (Thomae; appl. 12.5.1972). Keck, J.: Justus Liebigs Ann. Chem. (JLACBF) 707, 107 (1967). Formulation(s): amp. 15 mg; cps. 75 mg; drops 7.5 mg, 30 mg; eff. tabl. 30 mg, 60 mg; f. c. tabl. 30 mg, 60 mg; inhalation sol. 7,5 mg; inj. 1000 mg; syrup 15 mg, 30 mg; tabl. 30 mg, 60 mg (as hydrochloride) Trade Namefs): D: Ambril (Glaxo Wcllcome) frenopect (Hefa Pharma) Mucosolvan (Boehringer Bronchopront (Mack, Lindoxyl (Lindopharm) Ing.; 1979) Illert.) Mucoclear (Mundipharma) Mucotablin-Tropfen duramucal (durachemie) Mucophlogat (Azuchemie) (Sanorania) 80 A Ambuside - Mucotectan (Boehringer Fluibron (Chiesi) Secretil (Caber) 1ng.)-comb. Fluixol (Ripari-Gero) Surfacatal (Boehringer stas-Hustenloser (Stada) LisopuIm (Esseti) Ing.) I: Amobronc (1st. Chim. Muciclar (Piam) Tauxolo (SIT) Inter.) Mucobron (OFF) Viscomucil (ABC-Torino) Atus (Metapharma) Mucosolvan (Boehringer J: Mucosolvan (Teijin; 1984) Broxol (Pulitzer) Ing.; 1982) Ambuside ATC: C02L Use: diuretic, antihypertensive RN: 3754-19-6 MF: C,,H,,CIN,0,S2 MW: 393.87 EINECS: 223-158-4 CN: 4-chloro-6-[(3-hydroxy-2-butenylidene)amino]-N'-2-propenyl-l,3-benzenedisulfonamide 6-amino-4-chloro- diethyl corbonate 6-chioro-3,4-dihydro-J-oxo- benzene- 1 ,J-disulfonornide 2H-1.2.4-benzothiadiozine- (cf. chlorothiozide synthesis) 7-sulfonarnide S,S-dioxide (I) ocetoocetoldehyde 1 Ambuside dirnethyl ocetol Reference(s): US 3 188 329 (Colgate-Palmolive; 8.6.1965; appl. 10.4.1962). intermediates: Close, W.J. et al.: J. Am. Chem. Soc. (JACSAT) 82, 1 132 (1960). Trade Name(s): F: Hydrion (Robert et Carrikre); wfm . EINECS: 22 6-9 9 4 -8 CN: 6-chloro-3,4-dihydro- 3-[ (2-propenylthio)methy1 ]-2 H- 1,2,4-benzothiadiazine-7-sulfonamide 1, l-dioxide 6-amino-4-chloro- chloroocetaldehyde benzene-1.3-disulfamide. 4-chloro- 6-[ (3-hydroxy-2-butenylidene)amino]-N&apos ;-2 -propenyl-l,3-benzenedisulfonamide 6-amino-4-chloro- diethyl corbonate 6-chioro-3,4-dihydro-J-oxo- benzene- 1 ,J-disulfonornide 2H-1.2.4-benzothiadiozine- (cf. chlorothiozide. 2-0 x 0-2 .3-dihydro-lH- 2-thioxo-2,3-dihydro- 7-chloro-5-phenyl-3H- 1.4-benzodiazepine (111) 1 H- 1 -4 -benzodiazepine l,4-benzadiozepine . (IV) 25OoC N b Alprazolom Reference(s): US 3 987 052