Pharmaceutical Substances Syntheses, Patents, Applications - Part 56 potx

Cropropamide C 551 Formulation(s): aerosol 1 mgl0.05 ml; cps. 100 mg; gran. 100 mg, 200 mg; nasal spray 2.8 mg1O. 14 ml, 20 mgl ml; ophthalmic drops 10 mg10.5 ml, 20 mglml (as disodium salt) Trade Name(s): Aarane (RhGne-Poulenc Rorer; 1983)-comb. Allergochrom (Ursapharm) Allergospasmin (ASTA Medica AWD; 1983)-comb. Colirnune (Fisons) Colirnune s 1001s 200 (Fisons) Durachrornan (durachemie) lntal (Fisons; Rh6ne- GB: Poulenc Rorer; 1970) Lomupren (Fisons) Opticrorn (Fisons) Pulbil (Klinge) Vividrin (Mann) generics Crornedil (Europhta) Crornoptic (Chauvin) Intercron (Laphal) Lomudal (RhGne-Poulenc Rorer Specia) Lomusol (RhGne-Poulenc Rorer Specia) Nalcron (Rh6ne-Poulenc Rorer Specia) Opticron (RhGne-Poulenc Rorer Specia) Intal Syncroner (Rh6ne- Poulenc Rorer; 1968) Nalcrom (RhGne-Poulenc Rorer) Opticrom (RhGne-Poulenc Rorer) Rynacrom Spray (RhGne- Poulenc Rorer) I: Cromantal (Nuovo Cons. Sanit. Naz.) Frenal (Schiapparelli Searle) Gastrofrenal (Schiapparelli Searle) Lomudal (Fisons) Nalcrom (Fisons) Rinofrenal (Schiapparelli Seark-comb. Sificrom (SIFI) Visuglican (Merck Sharp & Dohme)-comb. J: Intal (Fujisawa; 1971) USA: Aarane (Syntex); wfm Intal (Fisons; 1973); wfm Nasalcrom (Fisons); wfrn Opticrom (Fisons); wfm Cropropamide ATC: RO~AB Use: respiratory tonic RN: 633-47-6 MF: C,3H24N202 MW: 240.35 EINECS: 2 1 1-193-8 CN: N-[1-[(dirnethylamino)carbonyI]propyl]-N-propyl-2-butenamide propyl- 2-chloro-N.N- ornine dimethylbutyr- ornide Reference(s): US 2447 587 (Geigy; 1948; CH-prior. 1942j, Formulation(s): drops 15 % (comb. with crotetarnide) Trade Name(s): I Cropropomide D: Micoren (Geigy)-comb. F: Micorkne (Ciba-Geipy)- GB: Micoren (Geigyj-comb. with crotetamide; wfm comb. with crotetamide; with crotetamide; wfm wfm I: Micoren (Geigy)-comb. with crotetarnide; wfrn -7 552 C Crotamiton Crotamiton RN: 483-63-6 MF: C,,H,,NO MW: 203.29 LD,,,: 1600 mglkg (M, p.0.); 1500 mglkg (R, p.0.) CN: N-ethyl-N-(2-methylpheny1)-2-butenamide crotonoyl chloride N-ethyl-2- met hylaniline ATC: P03A Use: antipruritic, scabicide EINECS: 207-596-3 Reference(s): GB 615 137 (Geigy; appl. 1946). Formulation(s): cream 0.1 glg; gel 50 mg1100 g; ointment 100 rngllOO g; sol. 10 % Trade Name(s): D: Crotamitex-Gel F: Eurax (Zyrna) Eurax (Ciba-Geigy- (gepepharni) GB: Eurax (Novartis Consumer) . Fujisawa) Euraxil (Novartis I: Eurax (Zyma) USA: Burax (Westwood-Squibb) Consumer Health) J: Dermarin (Taisho) Crotetamide ATC: R07AB Use: respiratory tonic RN: 6168-76-9 MF: C,2H22N202 MW: 226.32 EINECS: 228-208-9 CN: N-[l-[(dimethylamino)carbonyl]propyl]-N-ethyl-2-butenamide ethylamine 2-chloro-N.N- dimethylbulyr- amide crotonoyl chloride Crotetamide Reference(s): US 2 447 587 (Geigy; 1948; CH-prior. 1942). Formulation(s): drops 15 % (comb. with cropropamide) Cyamemazine C 553 Trade Name(s): D: Micoren (Geigy)-comb. F: Micorkne (Ciba-Geigy)- GB: Micoren (Ge1gy)-comb. with cropropamide; wfm comb. with cropropamide; with cropropamide wfm I: Micoren (Zyma)-comb. with cropropamide C yamemazine (Cyamepromazine) ATC: N05AA06 Use: neuroleptic, tranquilizer RN: 3546-03-0 MF: C,,H,,N,S MW: 323.46 EINECS: 222-594-2 CN: l0-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile Z-chloropheno- thiozine P-cyanopheno- thiozine 1. NaNH2, xylene 2. cl&i:3 CH3 I 2. 1 -chloro-3-dimethyl- amino-2-methyl- Cyamemazine propane DE 1 056 61 1 (RhGne-Poulenc; appl. 1956; F-prior. 1955). Formulation(s): amp. 50 mg/5 ml; drops 4 %; sol. 40 mg/ml; tabl. 25 mg, 100 mg Trade Name(s): D: Neutromil (Farmita1ia)- F: Tercian (Specia) comb.; wfm Cyanocobalamin (Vitamin B ,,) ATC: B03BAO1 Use: antipernicious vitamin RN: 68-19-9 MF: C,,HxxCoN14014P MW: 1355.39 EINECS: 200-680-0 CN: cobinamide cyanide hydroxide dihydrogen phosphate (ester) inner salt 3'-ester with 5,6-dimethyl-1-a-D- ribofuranosyl- 1 H-benzimidazole 554 C Cvanocobalamin HO- -CH3 'CH, Cyanocobolarnin By fermentation with Streptotnycev griseus, S. olivaceus, S. aureofaciens, Bacillus megatherium or Propionobacterium freudenreichii. Molasses is used generally as fermentation medium, CoC1, and 5,6- dimethylbenzimidazole are added. Various adsorption and extraction methods are used for isolation from the fermentation liquors. Reference(s): review: Ullmanns Encykl. Tech. Chem., 3. AuB., Vol. 18,219. Kirk-Othmer Encycl. Chern. Technol., 2nd Ed. (15SWA8), Vol. 21, (1963-1971), 544. Bernhauer, K. et al.: Angew. Chem. (ANCEAD) 75, 1 145 (1963). fermentative preparation: US 2 505 053 (Merck & Co.; 1950; appl. 1948). US 2 530 416 (Merck & Co.; 1950; appl. 1949). US 2 563 794 (Merck & Co.; 1951; appl. 1949). US 2 582 589 (Abbott; 1952; appl. 1949). US 2 595 499 (Merck & Co.; 1952; appl. 1948). US 2 650 896 (Mcrck & Co.; 1953; appl. 1950). US 2 703 302 (Merck & Co.; 1955; appl. 1952). LJS 2 703 303 (Merck & Co.; 1955; prior. 1948). DE 1 046 258 (Soc. Farmaceutici Italia; appl. 1956; I-prior. 1955). DE 1 076 889 (Distillers; appl. 1958; GB-prior. 1957). US 2 951 017 (Distillers; 1960; GB-prior. 1957). US 3 000 793 (Merck & Co.; I96 1 ; prior. 1955). US 3 01 8 225 (Merck & Co.; 23.1.1962; prior. 1953). DE 1 080 264 (Distillers; appl. 1958; GB-prior. 1957). DE 1 09 1 705 (Roche; appl. 1959). DE 1 109 317 (Roche; appl. 1959). GB 1 451 694 (Richter Gedeon; appl. 25.10.1974; H-prior. 26.10.1973). US 4 1 19 492 (Nippon Oil; 10.10.1978; J-prior. 5.2.1976). yield increasing by addition of betaine to the nutritive medium: US 3 000 793 (Merck & Co.; 1961; appl. 1957). US 2 923 666 (Pabst Brewing Comp.; 1960; appl. 1954). isolationfrom liverpreparations: US 2 594 314 (Merck & Co.; 1952; appl. 1948). US 2 609 325 (Merck & Co.; 1952; appl. 1948). pur$icatiotl and isolation: US 2 607 717 (Merck & Co.; 1952; appl. 1949). US 2 626 888 (Merck & Co.; 1953; appl. 1950). US 2 628 186 (Research Corp.; 1953.: appl. 1950). US 3 057 851 (Armour; 9.10.1962; prior. 1955). Cyclandelate C 555 Formulation(s): amp. 0.1 mg, 1 mg; drg. 1 mg; drops 0.05 mg; inj. flask 0.5 mg, 1 mg. 5 mg D: B,, "Ankermann" (Worwag) B,,-Horfervit (Arteva Pharma) B ,, Rotexmedica @otexmedica) B,,-Steigerwald (Steigerwald) BIZ-Vicotrat (Heyl) Biovital (Dr. Schieffer)- comb. Bryonon (Protina)-comb. Cervevit (Baxter)-comb. Cobidec (Warner- Lambert)-comb. Cytobion (Merck) Dodecatol (Heyl)-comb. Dolo-Neurobion (Merck1e)-comb. Eryfer (Cassella-med)- comb. Eukalasan (Steigerwaldl- comb. Hamo-Vibolex (Anphasaar) Lophakomb (Lomapharm) Multibionta (Merckle)- comb. Natabec (Warner-Lambert) Neurotrat (Knoll)-comb. Vicapan R,, (Merckle) Vitamin B 12 forte (Hevert) Vitamin B,, (OTW) Vitamin B 12 Injektionslosung (Wiedemann) Vitamin-B ,,-ratiopharm (ratiopharm) numerous combination preparations F: Alvityl (Sohay)-comb. Azedanit (Whitehall)- comb. B,, Mille Delagrange (SynthClabo) Berocca (Nicholas)-comb. Forvital (Whitehall)-comb. Pharmaton (Boehringer 1ng.)-comb. Soluvit (UCB)-comb. Synergil (Dakota) Vitamine B,, Aguettant (Aguettant) Vitamine B,, Lavpisier (Chaix et du Marais) Vivamyne (Whitehall). comb. numerous combination preparations GB: Cytacon (Goldshield) Cytamen (Evans) I: Cobcquin (Casarini) Dobetin (Angclini) Efargen (Teofarma)-comb. Epargriseovit (Farmitah- comb. Eritrovit B 12 (Lisapharma) Mionevrasi (Boehringer Mannh.)-comb. Neoepari biol (Ecobi)- comb. Reticulogen (Lilly) Tonicum (SIT)-comb. numerous combmation preparations J: Actamin B,, (Yashima) Redisol (Merck-Banyu) numerous combination preparations USA: Bevitarnel (Westlake) Chromagen (Savage) Cyanocobalamin (Elkins- Sinn) Fetrin (Lunsco) Hemocyte-F (U.S. Pharmaceutical) Mega-B (Arco) Nascobal (Schwarz) Niferex (Schwarz) Nu-Iron-Plus Elixier (Merz) Rubramin PC (Squibb) Trinsicon (UCB) numerous combination preparations Cyclandelate ATC: C04AXOI Use: antispasmodic RN: 456-59-7 MF: C,,HZ4O3 MW: 276.38 EINECS: 207-271-6 LD,: >10 gkg (M, p.0.); 5 glkg (R, p.0.) CN: a-hydroxybenzeneacetic acid 3,3,5-trimethylcyclohexyl ester DL-mandelic 3.3.5-trimethyl- Cyclandelote acid cyclohexanol Reference(s): US 2 707 193 (Brocades-Stheeman; 1955; NL-prior. 1949) 556 C Cyclizine purification: US 3 663 597 (American Home; 16.5.1972; appl. 5.5.1970). Formulation(s): cps. 400 mg; drg. 200 mg, 400 mg Trade Name(s): D: Eucebral-N (Siidmedica)- comb. Natil(3M Medica) Spasmocyclon (3M Medica) F: Cyclergine (Poirier) Cyclospasmol (Yamanouchi) Novodil (Augot) Vascunormyl (A1con)- comb. GB: Cyclobral (Norgine); wfm Cyclospasmol (Brocades); wfm I: Ciclospasmol (Brocades) J: Anticen (Nippon Kayaku) Aposelebin (Hokuriku) Capilan (Takeda) Capistar (Kowa Yakuhin) Ceaclan (Mohan) Cepidan (Meiji) Circle-one (Funai) Circulat (Kotani) Cyclan (Ohta) Cyclan-Cap. (Nichiiko) Cyclansato (SS) Cycleat Cap. (Hishiyama) Cycralate (Kanto) Hacosan (Sanko) Hi-Cyclane Cap. (Vama) Mandelic (Seiko) Marucyclan (Maruko) Mitalon (Toyo Pharmar) Newcellan Cap. (Kowa) Saiclate (Morishita) Sancyclan (Santen) Sepyron Cap. (Sankyo) Spadelate Cap. (Zeria) Venalal (Mochida) Zirkulat (Nippon Shoji) USA: Cyclospasmol (Ives); wh generics; wfm C yclizine ATC: RO~AEO~ Use: antihistaminic, anti-emetic RN: 82-92-8 MF: C,,Hz2N2 MW: 266.39 EINECS: 201-445-5 LD,,: 147 mglkg (M, p.0.) CN: 1-(diphenylmethy1)-4-methylpiperazine monohydrochloride RN: 303-25-3 MF: Cl,Hz,Nz , HCI MW: 302.85 EINECS: 206- 136-9 LD,,,: 165 mglkg (M, p.0.) lactate (1:l) RN: 5897-19-8 MF: Cl,H,2N2. C,H60, MW: 356.47 benzhydryl 1 -methyl- chloride piperozine CH3 Cyclizine US 2 630 435 (Burroughs Wellcome; 1953; prior. 1948). Formulafion(s): amp. 50 mg; suppos. 100 mg; tabl. 25 mg, 50 mg (as hydrochloride) Trade Name(s): D: Migrane-Kranit spezial GB: Diconal (Glaxo Wellcome)- I: Marzine (Wellcome; as (Krewe1)-comb.; wfm comb. hydrochloride) F: Migwell (Glaxo Wellcome; Migril (Glaxo Wellcome)- J: Cleamine (Kodama)-comb. as hydrochloride)-comb. comb. USA: Marezine (Burroughs Valoid (Glaxo Wellcome) Wellcome); wfm Cvclnbarbital C 557 Marezine (Burroughs Wellcome; as hydrochloride); wfrn Cyclobarbital (Hexemal; Cyclobarbitone) ATC: N05CA10 Use: hypnotic RN: 52-31-3 MF: C,,H,,N,O, MW: 236.27 EINECS: 200-138-3 LDG 840 mg/kg (M, p.0.) CN: 5-(1 -cyclohexen- 1-yl)-5-ethyl-2,4,6(1 H,3H,SH)-py rimidinetrione calcium salt RN: 5897-20-1 MF: C,,H,,N,O, . xCa MW: unspecified EINECS: 227-590-4 calcium salt (2: 1) RN: 143-76-0 MF: C,,H,,CaN,O, MW: 5 10.60 EINECS: 205-610-2 bromide @o- methyl methyl methyl 2-cyana- haxonone cyanoacetate 1 -cyclohexenyl- cyanoocetote 2-(I -cyclohexenyl)- butyrate (1) dicyano- diamide Cyclobarbital u DRP 442 655 (Bayer; 1924). GB 231 150 (Bayer; 1924). Fonulation(s): cps. 75 mg; tabl. 100 mg, 200 mg (as calcium salt) Trade Name(s): D: Dormopan (Bayropharm)- comb.; wfrn Gastripan (Merck1e)- comb.; wfrn Itridal (Homburg)-comb.; wfrn Medinox (Pfleger)-comb.; wfrn Phanodorm (Bayer); wfrn Somnubene (Merck1e)- comb.; wfrn Somnupan C (Merckle); wfrn Stodinox (Lorenz)-comb.; wfrn Tcmpidorm N (Roland)- comb.; wfrn generics; wfrn F: Dormopan (Bayer- Pharma)-comb.; wfrn GB: Phanodorm (Winthrop); wfrn Rapidal (Medo) I: Cyclobarbitalum (Sale di calcio) J: Adorm (Shionogi) 558 C Cyclobenzaprine C yclobenzaprine ATC: M03BXO8 Use: muscle relaxant, psychosedative RN: 303-53-7 MF: C2,,H2,N MW: 275.40 EINECS: 206-145-8 LD,,,: 36 tnglkg (M, i.v.); 250 mglkg (M, p.0.) CN: 3-(5H-dibenzo[a,~cyclohepten-5-ylidene)-N,N-dimethyl-l -propanamhe hydrochloride RN: 6202-23-9 MF: C,,,H,,N . HCI MW: 31 1.86 EINECS: 228-264-4 LD,,,: 36mg/kg(M,i.v.);250mglkg(M,p.o.) dibenzo[o,d]cyclo- J-dimethylornino- hepten-5-one propylmognesium chloride HCI, CHJCOOH 1 b Reference(s): US 3 272 864 (Merck & Co.; 13.9.1966; appl. 19.4.1962). US 3 409 640 (Schering Corp.; 5.1 1.1968; appl. 22.7.1 959). medical use: US 3 882 246 (Merck & Co.; 6.5.1975; prior. 3 1.1.1973,21.5.1971,9.4.1974). Ebrmdation(s): cps. 10 mg; tabl. 10 mg, 30 mg (as hydrochloride) Trade Name(s): 1: Flexiban (Neopharmed) USA: Flexeril (Merck; as hydrochloride) Cyclobutyrol ATC: A05AX03 Use: choleretic RN: 512-16-3 MF: C,,H,,03 MW: 186.25 EINECS: 208-138-5 LD,,,: 2900rng/kg(M,i.v.);>lOg/kg(M,p.o.); 1760 mglkg (R, i.v.); 4820 mglkg (R, p.0.) CN: a-ethyl-1-hydroxycyclohexaneacetic acid monosodium salt RN: 11 30-23-0 MF: C,,H,,Na03 MW: 208.23 EINECS: 214-458-6 calcium salt RN: 40043-69-4 MF: C,,H,,O,~ xCa MW: unspecified betaine salt (1:l) RN: 23579-12-6 MF: CI,,H1703 . CSHl2NO2 MW: 303.40 EINECS: 245-750-1 : Cyclofenil C 559 cyclo- ethyl a- hexonone bromobutyrote 1 Cyclobutyro I Reference(s): DE 1094 254 (Lab. J. Logeais; appl. 14.2.1959; F-prior. 19.2.1958). US 3 065 134 (Lab. J. Logeais; 20.1 1.1962; F-prior. 19.2.1958). Maillard, J. et a].: Bull. Soc. Chim. Fr. (BSCFAS) 1958, 244. Formulation(s): amp. 200 mg; tabl. 250 mg (as sodium salt) Trade Name(s): D: Benestan (Kar1spharma)- Trommgallol I: Epa-Bon (Sifarma) comb.; wfm (Trommsdorff)-comb.; wfm J: Lipotrin (Eisai) F: HCbucol (J. Logeais) Riphole N (Nichiiko) Cyclofenil ATC: G03GBO1 Use: gonadotropin stimulant (against infertility) RN: 2624-43-3 MF: C,,H,O, MW: 364.44 E~NECS: 220-089-1 LD,,: >12.5 gkg (M, p.0.); >12 g/kg (R, p.0.) CN: 4-[[4-(acetyloxy)phenyl]cyclohexylidenemethy]phenol acetate ethyl cyclo- hexonecorboxylote 4-methoxyphenyl- magnesium bromide (from 4-bromoonisole) u 4,C-dimethoxy- benzhydrylidene- cyclohexane (1) KOH, 220 OC pyridine 1 , - 0 ocetic anhydride 4.4'-dihydroxy- benzhydrylidene- cyclohexane Cyclofenil Reference(s): US 3 287 397 (K.G. Olsson et a].; 22.11.1966; GB-prior. 22.1 1.1960). Formulation(s): tabl. 100 mg, 200 mg, 400 mg Trade Name(s): D: Fertodur (Schering); wfrn GB: Ondonit (Roussel); wfrn I: Fertodur (Schering) F: Ondogyne (Roussel); wfm Rehibin (Thames); wfm Neoclym (Poli) 560 C Cyclomethycaine J: Sexovid (Teikoku Zoki) Cyclomethycaine ATC: SOlHA Use: local anesthetic RN: 139-62-8 MF: C2,H3,NO3 MW: 359.51 CN: 4-(cyclohexy1oxy)benzoic acid 3-(2-methyl-1-piperidiny1)propyl ester sulfate (2:l) RN: 6202-05-7 MF: C2pH,,NOv 112H,S04 MW: 817.10 sulfate (1:l) RN: 50978-10-4 MF: C2,H,,N0, . H,SO, MW: 457.59 3-chloro- 2-methyl- 3-(2-methyl- chloride 3-(2-methyl- I-proponol piperidine piperidina)- piperid~no). I -propano1 propyl chloride (I) 4-cyclohexyloxy- benzoic acid Reference(s): US 2 439 818 (S. M. McElvain, T. P. Carney; 1948; appl. 1946). McElvain, S.M.; Carney, T.P.: J. Am. Chem. Soc. (JACSAT) 68, 2592 (1946). Formulation(s): cream 0.5 % - 1 %; ointment 0.5 - 1%; spray 0.25 % Trade Name(s): USA: Surfacainc (Lilly); wfrn Cyclopentamine ATC: ROIAA02 Use: sympathornirnetic RN: 102-45-4 MF: CyH,,N MW: 141.26 CN: N,a-dirnethylcyclopentaneethanamine cyclo- cyanaocctic pentanone acid cyclopentylidene- acetonitrile cyclopentyl- acetonitrile (I) methylrnognesiurn cyclopentyl- bromide ocetone Cyclopentamine L . l 0-[ 3-( dimethylamino )-2 -methylpropyl ]-1 0H-phenothiazine-2-carbonitrile Z-chloropheno- thiozine P-cyanopheno- thiozine 1. NaNH2, xylene 2. cl&i:3 CH3 I 2. 1 -chloro-3-dimethyl- amino-2-methyl- Cyamemazine. tonic RN: 63 3-4 7-6 MF: C,3H24N202 MW: 240.35 EINECS: 2 1 1-1 9 3-8 CN: N-[ 1-[ (dirnethylamino)carbonyI]propyl]-N-propyl-2-butenamide propyl- 2-chloro-N.N- ornine dimethylbutyr- ornide Reference(s):. respiratory tonic RN: 616 8-7 6-9 MF: C,2H22N202 MW: 226.32 EINECS: 22 8-2 0 8-9 CN: N-[l-[(dimethylamino)carbonyl]propyl]-N-ethyl-2-butenamide ethylamine 2-chloro-N.N- dimethylbulyr- amide crotonoyl