Clocortolone C 51 1 + B~-CI NoNH2 ti CI ornide 3-chloro-l0,1 1 -di- 1 -brorno-3- hydro-5H-dibenz- chloropropane [bblazepine DMF , + HN*3 + NH2 piperidine-4- corboxamide (cf, piparnperone synthesis) Reference(s): DOS 1 905 765 (Yoshitomi; appl. 6.2.1969; J-prior. 7.2.1968). US 3 668 210 (Yoshitomi; 6.6.1972; J-prior. 7.2.1968). Formulation(s): tabl. 10 mg, 25 mg (as hydrochloride) Trade Nurne(s)c J: Clofekton (Yoshitomi- Takeda; 1974) Clocortolone ATC: D07AB21 IJse: glucocorticoid RN: 4828-27-7 MF: C2,H2,C1FO4 MW: 41 0.9 1 EINECS: 225-406-7 CN: (6a,l I P,l6a)-9-chloro-6-fluoro- 1 I ,2 1 -dihydroxy- 16-methylpregna-1,4-diene-3,20-dione pivalate RN: 34097- 16-0 MF: C2,H,,C1F05 MW: 495.03 EINECS: 25 1-826-5 caproate RN: 4891-71-8 MF: C2,H,,ClF05 MW: 509.06 EINECS: 225-513-9 &I:3 +, CD4, dioxane b N-chloro- 0 '. succinirnide F 3.20-dioxa-6a-fluoro-21- Clocortolone hydraxy-16a-methyl- 1,4,9(1 1)-pregnatriene 512 C Clodantoin pivalic onhydride I F Clocortolone pivolote I 0 0 pyridine Clocortolone f H3C coproic anhydride Reference(s): F Clocortolone caproote ~i-a~~l. 6 4 12 708 (Schering AG; appl. 2.1 1.1964; D-prior. 9.1 1.1963). FR 6 752 M (Schering AG; appl. 9.1 1.1966; D-prior. 9.1 1.1965). synthesis qf starting compound: DOS 1 913 042 (Schering AG; appl. 11.3.1969). alternative syrzthesis: DOS 2 01 1 559 (Schering AG; appl. 7.3.1970). Forrnulation(s): cream 1 mglg Trade Name(s): D: Crino-Kaban (Asche; as Kabanimat (Asche; as pivalate-comb.) pivalate and capronate) Kaban (Asche; as pivalate Procto Kaban (Asche; as and capronate-comb.) capronate)-comb. I: Cilder (Cilag; as pivalate); wfm USA: Cloderm (Penedem; as pivalate) Clodantoin (Chlordantoin) ATC: GOlAXOl Use: fungicide RN: 5588-20-5 MF: CI,HI,CI3N,O2S MW: 347.69 EINECS: 226-995-3 LDS,,: >I165 mglkg (R, p.0.) CN: 5-(1-ethylpentyl)-3-[(trichloromethyl)thio]-2,4-imidazolidinedione H3c2.3fyo + CI \ S-CC13 + N- Na+ 0 Reference(s): US 2 553 770 (Standard Oil; 1951; prior. 1949). H3cqyo N, 0 S-CCI, 5-(1 -ethylpentyl)- trichlorornethyl- Clodontoin hydontoin sodium solt sulfenyl chloride Clodronate disodium C 5 13 Formuiation(s): cream; gel; powder Trade Name(s): GB: Sporostacin (Ortho); wfm USA: Sporostacin (Ortho)-comb.; J: Gynelan (Eisai)-comb. wfm Clodronate disodium ATC: ~05~~02 (Clodronic acid disodium salt) Use: calcium metabolism regulator RN: 22560-50-5 MF: CH2CI,Na,0,P, MW: 288.86 EINECS: 245-078-9 CN: (dichloromethylene)bis(phosphonic acid) disodium salt free acid RN: 10596-23-3 MF: CH,C120,P2 MW: 244.89 EINECS: 234-212-1 H C 0, ,0 CH3 3Y P Y H3C 0hr + CH3 CH, A H3C CH3 H~c ( ~CH~ CH3 H3C dibromo- triisopropyl tetraisopropyl methane phosphite rnethylenediphosphonote (1) 1. Na 1. HCI 1 1. sadium I Clodronote disodiurn Reference(s): DOS 1 467 655 (Procter & Gamble; appl. 17.3.1964; USA-prior. 18.3.1963). DOS 1 793 768 (Procter & Gamble; appl. 17.3.1964; USA-prior. 18.3.1963). US 3 404 178 (Procter & Gamble; 1.10.1968; appl. l8.3.l963,7.lO.l965). US 3 422 021 (Procter & Gamble; 14.1.1969; appl. 18.3.1963). Quimby, O.F. et al.: J. Org. Chem. (JOCEAH) 32,4111 (1967). alternative synthesis: McKenna, C.E. et al.: Phosphorus sulfur 37, 1 (1998) Formulation(s): amp. 300 mg/5 ml, 300 mg/lO ml; cps. 400 mg; f. c. tabl. 520 mg, 800 mg Trade Name(s): D: Bonefos (Astra; medac) F: Clastoban (Rorer; Roger I: Clasteon (Gentili) Ostac (Roche; 1988) Bellon) Difosfonal (SPA) Cytos (Roche) Ossiten (Roche) 514 C Clofedanol Clofedanol (Chlophedianol) ATC: R05DB10 Use: antibssive RN: 791-35-5 MF: C,,H,CINO MW: 289.81 EINECS: 212-340-9 LDSo: 70 mgkg (M, i.v.); 300 mgfkg (M, p.0.) CN: 2-chloro-a-[2-(dimethylamino)ethyl]-a-phenylbenzenemethanol hydrochloride RN: 51 1- 13-7 MF: C,,H,CINO . HCI MW: 326.27 EINECS: 208-124-9 LD,,,: 42 mgkg (M, i.v.); 284 mglkg (M, p.0.); 53 mgkg (R, i.v.); 350 mgkg (R, p.0.); 84 mglkg (dog, p.0.) 2-chloro- acela- benzophenone nitrile I Clofedonol I 2'-chlaro- poraform- dimethyl- 2'-chloro-3- acetophenane aldehyde amine dimethylomino- propiophenone (IL) phenylmagnesium bromide Refermce(s): DE 1 080 568 (Bayer; appl. 8.1.1958). DE 1 083 277 (Bayer; appl. 19.3.1958). US 3 031 377 (Bayer; 24.4.1962: appl. 26.11.1957). fort nu la ti on(^): syrup 25 mg, 30 mg; tabl. 12.5 mg (as hydrochloride) Clofexamide C 515 Trade Namefs): D: Dicton (Do1orgiet)-comb.; Pectolitan (Kettelhack- I: Soltux (Corv1)-comb. wfm Riker); wfm J: Coldrln (N~ppon Shinyaku) F: Tussipltgyl (Bayer); wfm USA: Ulo (Riker); wfrn Clofexamide ATC: N06B Use: psychoanaleptic 1 RN: 1223-36-5 MF: C,,H2,ClN202 MW: 284.79 EINECS: 214-951-6 I CN: 2-(4-chlorophenoxy)-N-[2-(diethylamino)ethyl]acetamide 4-chlorophenoxy- N,N-diethyl- Clofexarnide ocetyl chloride ethylenediarnine Referencefs): GB 942 761 (Centre National de la Recherche Scientifique; appl. 8.4.1960; F-prior. 15.4.1959, 30.7.1959). Fonnulation(s): tabl. 50 mg, 400 mg Trade Namefs): F: Clofexan B la noramidopyrine (Anpharl- comb.; wfm Clofezone ATC: M01 AAO5; M02AA03 Use: anti-inflammatory, antirheumatic RN: 17449-96-6 MF: CI,H,oN20, . C14H2,C1N202 MW: 593.17 EINECS: 241-466-7 LD,,: 1700 mgkg (M, p.0.); 1950 mgkg (R, p.0.) CN: 2-(4-chlorophenoxy)-N-[2-(diethylamino)ethyl]acetamide compd. with 4-butyl- l,2-diphenyl-3,s- pyrazolidinedione (1: 1) dihydrate RN: 60104-29-2 MF: C,,H20N202. C14H21ClN202. 2H20 MW: 629.20 clofexornide phenylbutozone 516 C Clofibrate I Clofezone Reference(s): US 3 491 190 (P. Rumpf, J E., G. Thuillier; 20.1.1970; F-prior. 8.9.1965). Fbrmulation(s): cps. 200 mg, 400 mg; ointment 5 gI100 g; suppos. 400 mg Trade Name(s): D: Perclusone (Mack, Illert.); F: Perclusone (Serb)-comb. J: Panas (Grelan) wfm I: Perclusone (Marxer); wfm Clofibrate ATC: COlABOl Use: cholesterol depressant, antihyperlipidemic, antiarteriosclerotic RN: 637-07-0 MF: CI2Hl5C1O3 MW: 242.70 EINECS: 21 1-277-4 CN: 2-(4-ch1orophenoxy)-2-methylpropanoic acid ethyl ester 4-chloro- acetone chloro- 2-(4-chloro- Clofibrate phenol f orrn phenoxy)-2- methylpropanoic acid Reference(s): Julia, M. et al.: Bull. Soc. Chim. Fr. (BSCFAS) 1956,777. US 3 262 850 (ICI; 26.7.1966; GB-prior. 20.6.1958). Formulation(s): cps. 250 mg, 500 mg Trade Name(s): D: Regelan N 500 (Zeneca) F: Lipavlon (Zeneca) GB: Atromid S (Zeneca) I: Sinteroid (Crinos) J: Amotril (Sumitomo) Apoterin A (Seiko) Artehard (Nissin) Ateculon (Nippon C hemiphar) Ateles (Tokyo Hosei) Atemarol (Kowa Yakuhin) Athebrate (Kakenyaku) Atherolate (Fuji Zoki) Atheromide (Ono) Atmol (Taisho) Atosterine (Kanto) Auparton (Samva) Binograc (Zeria) Bresit (Toyo Jozo) Cholenal (Yamanouchi) Cholestol (Toho) Cholesrun (Hokuriku) Clarol (Toy ama) Clobrate (Chugai) Clobren (Morishita) Clofbate (Mohan) Climinon (Meiji) Deliva (Nippon Kayaku) Hyclorate (Funay) Hy pocerol (Fuso) Clofoctol C 517 t? Liprinal (Bany u) Scrobin (Nlkken) USA: Atromid S (Wyeth-Ayerst) t 4 : Clofoctol ATC: JOl XXO3; R07A Use: antibacterial (in respiratory infections) RN: 37693-01-9 MF: C21H26C120 MW: 365.34 EINECS: 253-632-6 LD,: >4000 mglkg (R, p.0.) CN: 2-[(2,4-dichlorophenyl)methyl]-4-(1,1,3,3-tetramethylbutyl)phenol CH3 4-(1,1,3,3-tetra- 2.4-dichloro rnethylbuty1)- benzyl phenol chloride Clofoctol I CH3 Reference(s): FR 1602455 (I. R. C. E. B. A,; appl. 21.8.1968; GB-prior. 31.8.1967). US 3 830 852 (I. R. C. E. B. A.; 20.8.1974; F-prior. 18.8.1970). DOS 2 140 765 (I. R. C. E. B. A.; appl. 13.8.1971; F-prior. 18.8.1970). preparation of 4-(1,1,3,3-tetramethylbutyI)phenol: US 2 726 270 (Dow Chem.; 195 1). DE 842 073 (Reichhold Chem. Inc.; 1950). US 2 732 448 (California Research Corp.; 1953). US 2 572 019 (DuPont de Nemours & Co.; 1950). further patents are described before 1950. Formulation(s): suppos. 100 mg, 200 mg, 750 mg Tmde Name(s): F: Octofene (DCbat; 1978) I: Gramplus (Chiesi) Octofene (Roussel; 1985) Clometacin ATC: NO2 Use: anti-inflammatory, analgesic RN: 25803-14-9 MF: C19H,6CIN04 MW: 357.79 EINECS: 247-271-3 LD,,: 1 g/kg (M, p.0.) CN: 3-(4-chlorobenzoyl)-6-methoxy-2-methyl-1H-indole-l-acetic acid 4-rnethoxy-2- nitroethone nitrobenzaldehyde 518 C Clomethiazole 6-methoxy-2- N.N-dirnethyl-4- methylindole (I) chlorobenzornide 1. NaH, DMF 1. KOH, CH30H rCOOH 2. HCI acetate Clornetacin Reference(s): DE 1 901 167 (Roussel-Uclaf; appl. 10.1.1969; F-prior. 11.1.1968, 10.4.1968, 10.9.1968, 11.9.1968, 10.12.1968). Formulatinn(s): tabl. 150 mg Trade Name(s): F: . DupCran (Cassenne); wfm Clomethiazole ATC: N05CM02 Use: anticonvulsant, hypnotic, sedative RN: 533-45-9 MF: C,H,ClNS MW: 161.66 EINECS: 208-565-7 LDo,: 94 mglkg (M, i.v.); 21 10 mglkg (M, p.0.) CN: 5-(2-chloroethy1)-4-methylthiazole ethanedisulfonate (2:l) RN: 1867-58-9 MF: C,H,ClNS. 1/2C2H606S2 MW: 513.51 EINECS: 217-483-0 LD,,,: 150 mglkg (M, i.v.); 835 mglkg (M, p.0.) ornrnoniurn 1.3-dichloro- 5-(2-chloroethy1)- dithiocarbarnate 4-oxopentone 2-rnercapto-4- rnethylthiazole Clornethiazole I2 Reference(s): CH 200 248 (Roche; 1937). US 3 031 457 (R. Charonnat, J. Chareton, A. Boune; 24.4.1962; F-prior. 28.9.1955). alternative syntheses: Buchman, E.R.: J. Am. Chem. Soc. (JACSAT) 58, 1803 (1936). Sawa, Y.; Ishida, T.: Yakugaku Zasshi (YKKZAJ) 76, 337 (1956). Fnrmulation(s): amp. 0.8 % (as ethanedisulfonate); cps. 192 mg, 300 mg; syrup 320 mgllO ml; tabl. 500 mg Clometocillin C 519 + Tmde Name(s): D: Distraneurin (Astra) F: Hemineurine (Dkbat); wfm GB: Heminevrin (Astra) ATC: JO ICE07 Use: antibiotic RN: 1926-49-4 MF: C17H,,C12N205S MW: 433.3 1 EINECS: 217-657-6 CN: [2S-(2a,5a,6~)]-6-[[(3,4-dichlorophenyl)methoxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1- azabicyclo[3.2.0]heptane-2-carboxylic acid RN: 15433-28-0 MF: C,,H1,Cl2KN20,S MW: 47 1.40 $4-dichloro-a- msthoxyphenyl- acetic acid COOH I I + 0, NQH3 K2C0,, acetone. O°C, P* 7-6 k~ CH3 HzN H 6-ominopenl cillon~c acid ReJerence(s): US 3 007 920 (Recherche Industrie Therapeutiqucs; 7.1 1.196 1; GB-prior. 28.10.1960) Formulation(s): tabl. 500 mg Tmde Name(s): F: Rixapen (Smith Kline & French); wfm Clomifene (Clomiphene) ATC: G03GB02 Use: synthetic gonadotropin stimulant, antiestrogen RN: 91 1-45-5 MF: C,H2,C1N0 MW: 405.97 EINECS: 21 3-008-6 LD~ 1700 mgkg (M, p.0.) CN: 2-[4-(Zchloro- 1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine citrate (Id) RN: 50-41-9 MF: C2,H2,C1N0 . C6H80, MW. 598.09 EINECS: 200-035-3 LD,: 1400 mgkg (M, p.0.); 5750 mgkg (R, p.0.) 520 C Clomipramine w + rCH3 NOOH + I - 0b f-3 benzylrnagnesiurn OH of chloride 4-hydroxy- 2-diethylomino- 4-(2-diethylamino- benzophenone ethyl chloride ethoxy)benzophenone HCI + 0 <N-C 0 N-chloro- succin- irnide Reference(s): US 2 914 563 (Merrell; 24.1 1.1959; prior. 6.8.1957). medical use: BE 782 321 (Richardson-Merrell; appl. 19.4.1971). Forrnulation(s): cps. 50 mg; tabl. 50 mg (as citrate) Trade Name(s): D: Clornhexal (Hexal) GB: Clomid (Hoechst) Dyneric (Henning Berlin) Serophene (Hoechst) Pergotime (Serono) I: Clomid (Lepetit) F: Clomid (Marion Merrell) Prolifen (Chiesi) Pergotime (Serono) J: Clomid (Shionogi) Clornifene Orifen (Iwaki) USA: Clomid (Hoechst Marion Roussel; as citrate) Serophene (Serono) Clomipramine ATC: N06AA04 Use: antidepressant RN: 303-49-1 MF: C,,H,,ClN, MW:. 314.86 EINECS: 206-144-2 LD,,,: 27 mglkg (M, i.v.); 380 rnglkg (M, p.0.); 6 13 rnglkg (R, p.0.) CN: 3-chloro-l0,11-dihydro-N,N-dimethyl-5H-dibenz[b~azepine-5-propanamine monohydrochloride RN: 17321-77-6 MF: C,,H,,CIN,. HCI MW: 351.32 EINES: 241-344-3 LD,,,: 22 mgkg (M, i.v.); 470 mgkg (M, p.0.); 26 mgkg (R, i.v.); 914 rnglkg (R, p.0.); 32 mgkg (dog, i.v.); 383 mgkg (dog, p.0.) . 482 8-2 7-7 MF: C2,H2,C1FO4 MW: 41 0.9 1 EINECS: 22 5-4 0 6-7 CN: (6a,l I P,l6a )-9 -chloro-6-fluoro- 1 I ,2 1 -dihydroxy- 16-methylpregna-1,4-diene-3,20-dione pivalate RN: 3409 7- 1 6-0 MF:. RN: 192 6-4 9-4 MF: C17H,,C12N205S MW: 433.3 1 EINECS: 21 7-6 5 7-6 CN: [2S-(2a,5a,6~) ]-6 -[ [(3,4-dichlorophenyl)methoxyacetyl]amino ]-3 ,3-dimethyl-7-oxo-4-thia- 1- azabicyclo[3.2.0]heptane-2-carboxylic. anti-inflammatory, analgesic RN: 2580 3-1 4-9 MF: C19H,6CIN04 MW: 357.79 EINECS: 24 7-2 7 1-3 LD,,: 1 g/kg (M, p.0.) CN: 3-( 4-chlorobenzoyl )-6 -methoxy-2-methyl-1H-indole-l-acetic acid 4-rnethoxy-2-