Clidinium bromide C 501 potassium cyanide 1. AICI3 'if 2. H,, Pd-C V , 11 1. olurninurn N-chlaro- chloride succinimide ?ejerence(s): I Juby, P.F. et al.: J. Med. Chcm. (JMCMAR) 15,1297 (1972). (alternative synthesis described) DOS 2 004 038 (Bristol-Myers; appl. 29.1.1970; USA-prior. 3 1.1.1969). US 3 565 943 (Bristol-Myers; 23.2.1971; prior. 17.9.1969, 3 1.1.1969). US 3 663 627 (Bristol-Myers; 16.5.1972; prior. 1.6.1970). lltemative synthesis: 10s 2 330 856 (Takeda; appl. 16.6.1973; J-prior. 19.6.1972, 21.1 1.1972). "' Name(s): : Britai (Bristol-Banyu) Indanol (Takeda) 3idinium bromide ATC: A03C~02 Use: anticholinergic N: 3485-62-9 MF: C22H2,BrN0, MW: 432.36 EINECS: 222-471-3 ,DS0: 16 mgkg (M, i.v.); 492 mgkg (M, p.0.); 26 mgkg (dog, i.v.) !N: 3-[(hydroxydiphenylacetyl)oxy]-l-methyl-l-azoniabicyclo[2.2.2]octane bromide methyl iso- ethyl bromo- nicotinote acetate 2. HCI b "+ H2, PtO 3-0x0- quinuclidine 3-hydroxy- quinuclidine (11) 502 C Clindamycin brnzilic chloride Clidinium bromide Reference(s): US 2 648 667 (Hoffmann-La Roche; 1955; prior. 1951). Formulation(s): drg. 2.5 mg Trade Name(s): D: Librax (Roche)-comb. with GR: Libraxin (Roche)-comb. I: Librax (Roche)-comb. with chlorodiazepoxide; wfm with chlorodiazepoxide; chlorodiazepoxide F: Librax (Roche)-comb. with wfm USA: Librax (Roche)-comb. with chlorodiazepoxide chlorodiazepoxide Clindamycin ATC: DIOAFOI; GOIAAIO; JOIFFOI Use: antibiotic RN: 18323-44-9 MF: C,,H&1N,05S MW: 424.99 EINECS: 242-209-1 LDso: 2618 mgkg (R, s.c.) CN: (2s-trans)-methyl 7-chloro-6,7,8-trideoxy-6-[[(I -methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-l-thio- L-threo-a-D-gulucto-octopyranoside monohydrochloride RN: 21462-39-5 MF: C,,H&IN205S . HCI MW: 461.45 EINECS: 244-398-6 LD,,,: 245 mglkg (M, i.v.); 2539 mgkg (M, p.0.); 2193 mgkg (R, p.0.) Clindamycin I Reference(s): US 3 496 163. DE 1 795 740 US 3 418 414 (Upjohn; 24.12.1968; appl. 31.8.1966). US 3 475 407 (Upjohn; 28.10.1969; appl. 22.12.1967). US 3 509 127 (Upjohn; 28.4.1970; appl. 30.4.1968). use as antimalarinl: US 3 627 887 (Upjohn; 14.12.1971; appl. 17.10.1969). Clinofibrate C 503 Rydon reagent: Landauer, S.R.; Rydon, H.N.: 1. Chem. Soc. (JCSOA9) 1953,2224. Coe, D.G. et al.: J. Chem. Soc. (JCSOA9) 1954,2281. Rydon, H.N.; Tonge, B.L.: J. Chem. Soc. (JCSOA9) 1956, 3043. Formulation(s): amp. 300 mg12 ml, 600 mgl4 ml, 900 mg16 ml; cps. 150 mg, 300 mg; gel 10 mglg; sol. 10 mglml (as hydrochloride or phosphate); vaginal cream 20 mg Trade Namefs): D: Sobelin (Upjohn; 1968) Clinamycina (Savoma) USA: Clcocin (Pharmacia & generics Dalacin C (Pharmacia & Upjohn; 1970) F: Dalacine (Pharmacia & Upjohn; 1969) Clinda-Derm (Paddock) Upjohn; 1972) I: Dalacin C (Upjohn) Clindets Pledgets (Stiefel) GB: Cleocin (Upjohn) 1: Dalacin (Upjohn; 197 1) Clinofibrate ATC: B04AC Use: antihyperlipidemic, clofibrate derivative RN: 30299-08-2 MF: C2,H3,0, MW: 468.59 LD,,: 255 mglkg (M, i.p.); 1800 mglkg (M, p.0.); 410 mglkg (M, s.c.); 205 mag (R, i.p.); A000 mglkg (R, p.o.1; 2200 mglkg (R, s.c.) CN: 2,2'-[cyclohexylidenebis(4,1-phenyleneoxy)]bis[2-methylbutanoic acid] cyclo- phenol hexanone u 1 .l -bis(4-hydroxy- phenyl)cyclohexone (I) 2-butonone I Clinofibrate 1 0 KOH I+ gcVqcH3+ CHC13 - Referencefs): - US 3 716 583 (Sumitomo; 13.2.1972; appl. 7.4.1970; J-prior. 16.4.1969). US 3 821 404 (Sumitomo; 28.6.1974; J-prior. 16.4.1969). DOS 2 017 331 (Sumitomo; appl. 10.4.1970; 1-prior. 16.4.1969,2.5.1969). 0 COOH {FxH03v3c I XCH, synthesis of 1,l-bis(4-hydroxyphenyl)cyclohexane: DD46 281 (G. Drefahl, E. Littmann; appl. 22.1.1962). Formulation(s): tabl. 100 mg, 200 mg Trade Namefs): I: Deslipoze (Kowa Yakuhin) Lipirate (Hishiyama) Lipofibrate (Taiyo) Lipaderin (Uji) Lipoclin (Sumitomo; 1981) Prinmate (Sawai) 504 C Clioquinol Clioquinol (Chloroiodoquine; Iodochlorhydroxyquin) ATC: D08AH30; D09AA10; GOlAC02; PO I AA02; S02AA05 Use: wound- and bowel-antiseptic RN: 130-26-7 MF: C9HsC11N0 MW: 305.50 EINECS: 204-984-4 LD,,,: 69 mgkg (M, p.0.); >5 g/kg (R, p.0.) CN: 5-chloro-7-iodo-8-quinolinol oxyquinoline 5-chloro-B- (4- V-1 hydroxyquinoline Reference(s): DRP 1 17 767 (Ciba; 1899). Formulation(s): cream 3 gI100 g; emulsion 0.5 g1100 g; ointment 3 g/100 g Trade Name(s): D: Linola-sept (Wolff) Locacorten-Vioform (Novartis Pharma)-comb. Millicorten-Viofoml I: (Novartis Pharma)-comb. F: Diprosept (Schering- Plough)-comb. GB: Betnovate-C (Glaxo Wellcome)-comb. Locorten-Vioform (Novartis)-comb. Synalar C (Zeneca)-comb. Vioform-hydrocortisone (Novartis)-comb. Dermadex Chino1 J: (SmithKline Beecham)- comb. Diproform (Schering- Plough)-comb. Iodoclorossich TI (Tariff. USA: Integrativo) Locorten (Zy ma)-comb. Reticus (Farmila)-comb. Viobeta (ID1)-comb. Viocidina (IDI) Emaform (Tanabe) Entero-Vioform (Ciba- Geigy -Takeda) Mexaform (Ciba-Geigy- Takeda)-comb. Racet (Lemmon)-comb.; wfm Vioform (Ciba); wfm - - Clobazam ATC: N05BA09 Use: minor tranquilizer RN: 223 16-47-8 MF: CI6H,,C1N2O2 MW: 300.75 EINECS: 244-908-7 LD,,,: 5 10 mgkg (M, i.p.); 840 mgkg (M, p.0.); >2000 mglkg (R, p.0.) CN: 7-chloro-1 -methyl-5-phenyl- 1 H- 1.5-benzodiazepine-2,4(3H,SH)-dione 1 -3-dichloro- benzene CI nNo2 6 5-chloro-2- nitrodiphenyl- arnine (I) Clobenoside C 505 I manoethyl rnolonyl chloride 1 -demethyl- clobazam (11) Clabazam L DAS 1 793 837 (Roussel-Uclaf; appl. 14.12.1967; I-prior. 14.12.1966). US 3 984 398 (Roussel-Uclaf; 5.10.1 976; I-prior. 14.12.1966). US 3 836 653 (Boehringer Ing.; 17.9.1974; D-prior. 7.2.1967, 18.1. DOS 1 670 190 (Boehringer Ing.; appl. 7.2.1967). DOS 1 670 306 (Boehringer Ing.; appl. 18.1.1968). Weber, K.H. et al.: Justus Liebigs Ann. Chem. (JLACBF) 756, 128 I-demethylclobazam: DAS 1 668 634 (Roussel-Uclaf; appl. 14.12.1967; I-prior. 14.12.19 synthesis of 5-chloro-2-nitrodiphenylamine: Laubenheimer: Ber. Dtsch. Chem. Ges. (BDCGAS) 9,771 (1876). combination with nomifensine: DOS 2 724 683 (Hoechst; appl. 1.6.1977). Formulation(s): cps 10 mg; tabl. 10 mg, 20 mg Tmde Name(s): D: Frisium (Hoechst; 1977) GB: Frisium (Hoechst; 1979) F: Urbanyl (SynthClabo; I: Frisium (Hoechst Italia 1975) Sud) Clobenoside ATC: C05 Use: anti-inflammatory, vasoprotective RN: 29899-95-4 MF: C2sH,2C1,0, MW: 499.43 EINECS: 249-940-5 CN: ethyl 5,6-bis-0-[(4-chlorophenyl)methyl]-3-O-propyl-~-glucofuranoside 506 C Clobenzorex 1.25.6-di-0- isopropylidene- a-0-glucofuronose 1. HCI. CH30H 2. Hz. Pd-C I * NoOH + Br-/CH2 + ally1 bromide '3'3 1.2-0-isopropylidene- 3-O-propyl-a-O- glucofuronose HCI. C2H50H A KOH . I1 4-chlorobenzyl chloride I Clobenoside Reference(s): DOS 1 793 338 (Ciba-Geigy; appl. 3.9.1968; CH-prior. 11.9.1967). US 3 665 884 (Ciba-Geigy; 11.4.1972; CH-prior. 1 1.9.1967). - US 3 542 76 1 (Ciba-Geigy; 24.11.1970; appl. 25.4.1968; CH-prior. 1 1.9.1967). synthesis of I ,2-O-isopropylidene-3-O-propy~-a-~-glucofuranose: DOS 2 031 161 (Ciba; appl. 24.6.1970; CH-prior. 3.7.1969). Cunningham, J. et al.: Tetrahedron Lett. (TELEAY) 19, 1191 (1964). Corbettand, W.M.; McKay, J.E.: J. Chem. Soc. (JCSOA9), 2930 (1961). Fomulation(s): tabl. 200 mg, gel Trade Narne(s): CH: Aglidin (Zyma) Arvigol (Zyma) Finocal (Zyma) Flogasol (Vifor) Clobenzorex ATC: A08AA08 Use: appetite depressant RN: 13364-32-4 MF: C,,H,,CIN MW. 259.78 EINECS: 236-434-4 CN: (+)-N-[(2-chlorophenyl)methyl]-a-methylbenzeneethanamine Clobenztropine C 507 hydrochloride RN: 5843-53-8 MF: C,,H,,ClN. HCl MW: 296.24 EINECS: 227-434-5 LD,: 103 mg/kg (M, i.p.); :: I03 mglkg (R, i.p.) dexomphet- 2-chloro- omme benzaldehyde Clobenzorex Reference(s): FR 1 429 306 (S. I. F. A,; appl. 23.1 1.1964). Formulation(s): cps. 30 rng (as hydrochloride) Trade Name(s): F: Dinintel (Roussel Diarnant; as hydrochloride) Clobenztropine (Chlorobenztropine) ATC: R06 Use: antihistarninic RN: 5627-46-3 MF: C,,Hz4C1N0 MW: 341.88 CN: 3-[(4-chlorophenyl)phenylmethoxy]-8-methyl-8-azabicyco[3.2.l]octane hydrochloride RN: 14008-79-8 MF: C2,Hz4CINO . HCI MW 378.34 LD,: 174 mglkg (M, p.0.); 364 mg/kg (R, p.0.) xylene, 145-155 'C H$-;>O + ",-oc, - H tropine 4-chlorobenz- hydryl chloride I Clobenztropine I Reference(s): US 2 782 200 (Schenley Labs.; 1957; appl. 1955). alternative synthesis (with 4-chlorodiphenyldiazornethane): US 2 799 680 (S. Promer; 1957; appl. 1954). Trade Name(s): USA: Teprin (Endo); wfm 'I 508 C Clobetasol propionate Clobetasol propionate ATC: D07ADO1 Use: topical glucocorticoid RN: 25122-46-7 MF: C2,H,,CIF0, MW: 466.98 EINECS: 246-634-3 LD,,: >3 g/kg (M, p.0.); >3 dkg (R, p.0.) CN: (1 1 P, 16P)-21-chloro-9-fluoro- 16-methyl-17-(1 -oxopropoxy)pregna-1,4-diene-3,20-dione clobetasol RN: 25122-41-2 MF: C2,H28ClF0, MW: 410.91 EINECS: 246-633-8 belamethasone 17-propianate (cf. betomethasone dipropionate synthesis) lithium acetone chloride methonesulfonyl chloride Clobetasol propianate DE 1 902 340 (Glaxo; appl. 17.1.1969; GB-prior. 19.1.1968). US 3 721 687 (Glaxo; 20.3.1973; GB-prior. 4.4.1968). Formulation(s): cream 0.05 %; ointment 0.05 %; sol. 0.5 mglg (0.05 %) Trade Name(s): D: Dermoxin (Glaxo WellcomelCascan; 1976) Dermoxinale (Glaxo WellcomelCascan; 1977) Karison (Dermapharm) F: Dermoval (Glaxo Wellcome) GB: Dermovate (Glaxo Wellcome; 1973) I: Clobesol (Glaxo Myalore (Ohta) Wellcome) Siodelbate (Tatsumi) J: Betaleston (Nihon Solvega (Hisamitsu) Yaku hin) USA: Cormax (Oclassen) Delspart (Kodama) Temovate (Glaxo Dermovate (Glaxo; 1979) Wellcome; 1986) Entyfluson (Taiyo) Glydil (Shinshin) Mahady (Wukamoto) Clobetasone butyrate ATC: D07ABO1; SOlBA09 Use: topical glucocorticoid RN: 25 122-57-0 MF: C2,H3,C1FOS MW: 478.99 EINECS: 258-953-5 LD,,,: >6 glkg (M, p.0.); >6 glkg (R, p.0.) CN: (16~)-21-chloro-9-fluoro-16-methyl-17-(1-oxobutoxy)pregna-1,4-diene-3,11,20-trione Clobetasone butyrate C 509 * dobetasone $ RN: 54063-32-0 MF: CzzH2,ClF0, MW: 408.90 betamethasane 17-butyrote methone- sulfonyl chloride I Clobetosone butyrote I Reference(s): DE 1 902 340 (Glaxo; appl. 17.1.1969; GB-prior. 19.1 .l968). US 3 721 687 (Glaxo; 20.3.1973; GB-prior. 4.4.1968). cf, synthesis of betamethasone- 17-butyrate Formulation(s): eye drops 0.1 %; cream, ointment 0.5 mg/g (0.05 %) Tmde Name(s): D: Emovate (Glaxo; 1980) Trimovate (Glaxo Visucloben (Merck Sharp GB: Clobuvate (Dominion) Wellcome)-comb. & Dohme) Eumovate (Glaxo I: Eumovate (Glaxo; 1983) J: Kindavate (Glaxo; 1984) Wellcome; 1975) 510 C Clobutinol Clobutinol ATC: R0SDR03 Use: antitussive RN: 14860-49-2 MF: C14H22CIN0 MW: 255.79 EINECS: 238-926-4 LD,,: 53 mglkg (M, i.v.); 334 rnglkg (M, p.0.); 63 mg/kg (R. i.v.); 802 mglkg (R, p.0.); 45.3 mglkg (dog, i.v.) CN: 4-chloro-a-[2-(dimethylamino)-l-methylethyl]-a-rnethylbenzeneethanol hydrochIoride RN: 1215-83-4 MF: CI,H,,CINO~ HC1 MW: 292.25 EINECS: 214-931-7 LD,,,: 40.9 mglkg (M, i.v.); 334 mglkg (M, p.0.); 63 mglkg (R, i.v.); 802 rnglkg (R, p.0.); 45.3 mglkg (dog, i.v.) 4-chlorobenzyl- 4-dimethylomino- I Clobutinol magnesium chloride 3-methyl-2-butanone Refereta(s): DE 1 146 068 (Thomae; appl. 21.3.1959). DE 1 150 686 (Thomae; appl. 12.5.1960). US 3 121 087 (Thomae; 11.2.1964; prior. 18.3.1960, 28.6.1961). Engelhorn, R.: Arzneh-Forsch. (ARZNAD) 10,794 (1960). alternative synthesis: DE 1 153 380 (Thomae; appl. 21.5.1959). Formulation(s): amp. 20 mg12 rnl; drg. 40 mg; cps. 40 mg, 80 mg; drops 40 mg10.67 rnl; syrup 40 mg/lOml (a hydrochloride) Trade Name(s): D: Mentopin (Hermes) Silomat (Boehringer Ing.) Silornat cornpos~turn Nullatuss (Pharma Tussamed (Hexal) (Fher)-comb. Wernigerode) F. Silomat (Boehringer Ing.) J: S~lomat (Morishita) Rotafuss (MIP Pharrna) I: Silomat (Fher) Clocapramine ATC: SOIB Use: thyrnoleptic RN: 47739-98-0 MF: C2,H,,CIN,0 MW: 481.08 CN: I'-[3-(3-chloro-10,11-dihydro-SH-d1benz[bJlazepin-5-yl)propyl][1,4'-bipiperidine]-4'-carboxamide hydrochloride hydrate RN: 28058-62-0 MF: C2,H3,C12N,0 . HC1. H20 MW: 572.02 . CN: (2s-trans)-methyl 7-chloro-6,7,8-trideoxy- 6-[ [(I -methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-l-thio- L-threo-a-D-gulucto-octopyranoside monohydrochloride RN: 2146 2-3 9-5 MF: C,,H&IN205S. >2000 mglkg (R, p.0.) CN: 7-chloro-1 -methyl-5-phenyl- 1 H- 1.5-benzodiazepine-2,4(3H,SH)-dione 1 -3 -dichloro- benzene CI nNo2 6 5-chloro- 2- nitrodiphenyl- arnine (I) Clobenoside. 12 2-5 7-0 MF: C2,H3,C1FOS MW: 478.99 EINECS: 25 8-9 5 3-5 LD,,,: >6 glkg (M, p.0.); >6 glkg (R, p.0.) CN: (16~ )-2 1-chloro-9-fluoro-16-methyl-1 7-( 1-oxobutoxy)pregna-1,4-diene-3,11,20-trione