Pharmaceutical Substances Syntheses, Patents, Applications - Part 48 pot

Cimetidine C 471 Reference(s): DOS 2 934747 (Otsuka; appl. 28.8.1979; J-prior. 1.9.1978). US 4 277 479 (Otsuka; 7.7.198 1; J-prior. 1.9.1978). Nishi, T. et al.: Chem. Pharm. Bull. (CPBTAL) 31, 1151 (1983). medical use for treatment of nephritis: JP 2 178 227 (Otsuka; appl. 28.12.1988). medical use for treatment of Raytmud's syndrome: JP 2 178 226 (Otsuka, appl. 28.12.1988). Formulation(s): tabl. 50 mg, 100 mg Trade Name(s): J: Pletaal (Otsuka) Retal (Otsuka; 1988) Cimetidine ATC: A02BAOl Use: peptic ulcer therapeutic (Hz-receptor antagonist) RN: 51481-61-9 MF: C,,H,,N,S MW: 252.35. EINECS: 257-232-2 LD,,: 150 mg/kg (M, i.v.); 2550 mglkg (M, p.0.); 106 mglkg (R, i.v.); 5 glkg (R, p.0.); 206 mg/kg (dog, i.v.); 2600 mglkg (dog, p.0.) CN: N-cy ano-N-methyl-N'-[2-[[(5-methyl- 1 H-imidazol-4-yl)methyl]thio]ethy llguanidine H Na, liq. NH3 H + H2N-CHO + H3c$$ A '3'31;' .HCI 0 0 t-' 0 H 0 ethyl 2-chloro- formamide ethyl 5-methyl- 4-hydroxymethyl- ocetoocetate imidozole-4- 5-methylimidazole corboxylote hydrochloride (I) I + H2N-SH .HCI + dimethyl cyano- carboimidodithioate cysteamine 4-[(2-0minoethylthio)- (from cyanamide, KOH. hydrochloride methyl]-5-methyl- carbon disulfide and imidozole dihydrochloride dimethyl sulfate) Reference(s): US 3 894 151 (Smith Kline & French; 8.7.1975; GB-prior. 20.4.1972). US 4 000 302 (Smith Kline & French; 28.12.1976; GB-prior. 20.4.1972). DOS 2 320 131 (Smith Kline & French; appl. 19.4.1973; GB-prior. 20.4.1972) -medical use. DOS 2 344 779 (Smith Kline & French; appl. 5.9.1973; GB-prior. 5.9.1972 and 8.2.1973). US 3 950 333 (Smith Kline & French; 13.4.1976; appl. 14.3.1974; prior. 29.2.1972 and 20.9.1972) (I1) Cirnetidine 472 C Cimetropium bromide cimetidine "A": DOS 2 742 531 (Smith Kline & French; appl. 21.9.1977: GB-prior. 21.9.1976,24.1.1977). GB 1 543 238 (Smith Kline & French; appl. 21.9.1976, 24.1.1977, 20.9.1977; valid from 13.12.1977). precursors and alternative nzefkods: DOS 2 637 670 (Smith Kline & French; appl. 20.8.1976; USA-prior. 20.8.1975 and 27.5.1976). FR 2 321 490 (Smith Kline &French; appl. 16.8.1976; USA-prior. 20.8.1975 and 27.5.1976). GB 1 338 169 (Smith Kline & French; appl. 9.3.1971 and 22.7.1971; valid from 9.3.1972). DAS 2 21 1 454 (Smith Kline & French; appl. 9.3.1972; GB-prior. 9.3.1971 and 22.7.1971). US 4 018 931 (Smith Kline & French; 19.4.1977; appl. 4.12.1975; prior. 29.2.1972, 20.9.1972 and 14.3.1974). US 4 013 678 (Smith Kline & French; 22.3.1977; GB-prior. 2.9.1974). US 3 984 293 (Smith Kline & French; 5.10.1976; prior. 2.9.1974). BE 853 954 (Smith Kline Corp. GB appl. 26.4.1977; USA-prior. 22.2.1977). US 4 063 023 (Smith Kline & French; 13.12.1977; prior. 20.8.1975). DOS 2 649 059 (Smith Kline; appl. 28.10.1976; USA-prior. 29.10.1975). DOS 2 7 18 7 15 (Smith Kline; appl. 27.4.1977; USA-prior. 22.2.1977). US 4 049 672 (Smith Kline & French; 20.9.1977; appl. 17.3.1976; prior. 29.2.1972, 20.9.1972, 14.3.1974). US 4 104 472 (Smith Kline & French; 1.8.1978; prior. 9.2.1977,24.5.1977). US 4 163 858 (Smith Kline; 7.8.1979; prior. 9.2.1977,24.5.1977, 8.3.1978). DOS 2 805 221 (Smith Klinc; appl. 8.2.1978; USA-prior. 9.2.1977, 24.5.1977). DOS 2 814 355 (BASF; appl. 3.4.1978). DOS 2 855 836 (Lab. Om; appl. 22.12.1978; CH-prior. 28.12.lY77,7.12.1978). FR-appl. 2 386 525 (Ricorvi; appl. 17.10.1977; E-prior. 6.4.1977). X-ray structure: Hadicke, E. et al.: Chem. Bcr. (CHBEAM) 111,3222 (1978). combination with conventional anrihistuminics: US 4 104 382 (Smith Kline & French; 1.8.1978; prior. 9.4.1973, 16.4.1975, 27.9.1976). Formulation(s): amp. 200 mg/2 ml, 400 mg/4 ml, 1000 mg/lO ml; eff. tabl. 400 mg, 800 mg; f. c. and tabl. 200 mg, 400 mg, 800 mg Trade Nan~e(s): D: Altramet (ASTA Medica AWD) Azucimet (Anipharma) Tagamet (SmithKline Beecham; 1977) F: StomCdine (SmithKline Beecham) Tagamet (SmithKline Bcccham; 1977) GB: Algitec (SmithKline Beecham)-comb. Dyspamet (SmithKline Beecham) Galenamet (Galen) Tagamet (SmithKline Beecham; 1976) Zita (Eastern) I: Biomag (Pulitzer) Brumetidina (Bruschettini) Citimid (CT) Dina (San Carlo) Eureceptor (Zambon) Gastromet (Bayropharm) Neo Gastransil (Schiapparelli Searle) Notul (Mendelejeff; as hydrochloride) Stornet (Allergan) Tagamet (Smith Kline & French; 1977) Tametin (SmithKlinc Beecham) Temic (Farma Uno) Ulcedin (AGIPS) Ulcestop (Metaphama; as hydrochloride) Ulcodina (Locatelli) Ulcofalk (Interfalk) Ulcomedina (Leben's) Illis (Lafare) Vagolisal (Biotekfarma) J: Tagamet (SKF-Fujisawa; 1982) USA: Tagamet (SmithKline Beecham; 1977) Cimetropium bromide ATC: A03BB05 Use: anticholinergic, antispasmodic RN: 51598-60-8 MF: C,,H,,BrN04 MW: 438.36 CN: [7(S)-(1a,2~,4~,Srr,7~)]-9-(cyclopropylmethyl)-7-(3-hydroxy-l-oxo-2-phenylpropoxy)-9-methyl-3-o~a- 9-azoniatricyclo[3.3.1 .OZA]nonane bromide Cinchocaine C 473 Reference(s): US 3 853 886 (De Angeli; 10.12.1974; appl. 13.4.1973; GB-prior. 18.4.1972). US 3 952 108 (De Angeli; 20.4.1976, GB-prior. 18.4.1972). DOS 2 3 16 728 (De Angeli; appl. 4.4.1973; GB-prior. 18.4.1972). scopolamine cyclopropyl- Formulation(s): amp. 5 mglml; suppos. 50 mg; syrup 1 %; tabl. 50 mg Cirnetropiurn bromide Trade Name(s): I: Alginor (Boehringer Ing.; 1985) (q v.) methyl bromide J Cinchocaine (Dibucaine) ATC: C05AD04; D04AB02; NO1 BBO6; SO1 HA06 Use; local anesthetic RN: 85-79-0 MF: C20H2yN302 MW: 343.47 EINECS: 201-632-1 LD,: 24.5mg/kg(M,i.p.); 28.5mg/kg(M,s.c.) CN: 2-butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide monohydrochIoride RN: 61-12-1 MF: C20H2yN302 . HCI MW: 379.93 EINECS: 200-498-1 LD,: 3800 &kg (M, i.v.1; 52 mgkg (R, i.v.) N-acetyl- isatin L-chloro- 4-quinoline- carbonyl chlorcde 474 C Cineole 1 -butanol I Cinchocaine I Reference(s): DRP 537 104 (Ciba; appl. 1926). US 1 825 623 (Ciba; 1931; D-prior. 1926). Miescher, K.: Helv. Chim. Acta (HCACAV) 15, 163 (1932). Formulation(s): amp. 6 mgl3 ml (as hydrochloride); rectal ointment 5 mg1100 g; suppos. 1 mg Trade Name(s): D: Anumedin (Kade)-comb. Butazolidin (Novartis Pharma)-comb. Dolo-Postcrine (Kade) Faktu (Byk Gulden; Roland)-comb. Otobacid (Axhe)-comb. Procto-Kaban (Asche)- comb. Protospre (Hennig)-comb. Scheriproct (Schering)- comb. Ultrapoct (%hering)-comb. I: F: Deliproct (Schering)-comb. Ultraproct (Schering) comb. GB: Nupercainal (Novartis) J: Proctosedyl (Hoechst)- comb. Scheriproct (Schcring). comb. USA:. LJl traproct (%hering)- comb. Uniroid (Unigreg)-comb. Algolisina (Celsius)-comb Nupercainal (Ciba); wfm Ultraproct (Schering)- comb. Nupercain (Ciba-Geigy- Takeda) Percamin (Teikoku Kagaku-Nagase) Nupercaine (Ciba); wfm Cineole ATC: RO1 AX; ROSCA (Cajeputol; Eucalyptol) Use: antiseptic, expectorant RN: 470-82-6 MF: C,,H,,O MW: 154.25 EINECS: 207-431-5 LD,,: 2480 mgkg (R, p.0.) CN: 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane Principal ingredient of eucalyptus oils, isolated after separation of remaining terpenes with sulfuric acid. Reference(s): Ullmanns Encykl. Tech. Chem., 4. Aufl., Val. 22, 542. DRP 499 732 (Rhein. Kampfer-Fabrik; appl. 1928). US 2 090 620 (Newport Industries; 1937; appl. 1936). Formulation(s): cps. 100 mg; sol. 2 g1100 g, 15 g1100 g Trade Name(s): D: Denesol (Doerernkamp). Eufimenth (Lichtenstein) comb. comb. Pinimenthol (Spitzner)- comb. Cinepazet C 475 Rowachol (Kowa-Wagner)- comb. Rowatinex (Rowa- GB : Wagner)-comb. Soledum (Cassella-med) I: Transpulrnin (ASTA Medica) Wick VapoRup (Wick Phama) numerous combination preparations Rowachol (Rows)-comb. Rowatinex (Rows)-comb. Alc Ment Cmp (Formulario Naz.)-comb. Balsamic (Formulario Naz.)-comb. USA: Brochenolo Balsamo (Midy)-comb. Calyptol (Rhhe-Poulenc Rorer) Eucal (Tariff. Nazionalc) Eucalipt (Tariff. Nazionale) Rinostil (Deca)-comb. numerous combination preparations Listerine Antiseptic (Warner-Lambert) Cinepazet (Cinepazate) ATC: COlDX14 Use: vasodilator, antianginal RN: 23887-41-4 MF: C2,,H2,N206 MW: 392.45 EINECS: 245-927-3 LD6 1300 mglkg (M, p.0.); 300 mg/kg (M, i.v.) CN: 4-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-1)ropenyl]- 1-piperazineacetic acid ethyl ester maleate (1:l) RN: 50679-07-7 MF: C20H2,N206 . C,H,O, MW: 508.52 EIMECS: 256-709-2 Referencers): DAS 1 795 402 (Delalande; appl. 26.9.1968; GB-prior. 29.9.1967). $4.5-trimethoxy- ethyl 1 -piperazine- Formulation(s): tabl. 300 mg Cinepazet Trade Namefs): F: Vascoril (Delalande); wfm I: Vascoril (Delalande); wfm cinnornoyl chloride acetate Cinepazide ATC: C04AX27 Use: vasodilator (peripheral) RN: 23887-46-9 MF: Cz2H,,N3Os MW: 417.51 EINECS: 245-928-9 CN: 1-[2-oxo-2-(l-pyrrolidinyl)ethyl]-4-[l-oxo-3-(3,4,5-trimethoxyphcnyl)2-propenyl]pipera~ine maleate (1:l) RN: 26328-04-1 MF: C2,H3,N,O5. C,H40, MW: 533.58 EINECS: 247-613-1 LD,,: 617 mg/kg (M, i.v.); 1000 mglkg (M, p.0.); 414 rng/kg (R, i.v.); 1310 mg/kg (R, p.0.) 0 3,4.5-trirnethoxy- piperozinoocetic Cinepazide cinnornoyl chloride acid pyrrolidide Referenceis): DE 1 915 795 (Delalande; appl. 27.3.1969; GB-prior. 3.4.1968). DOS 2 043 350 (Delalande; appl. 1.9.1970; F-prior. 17.10.1969). US 3 634 41 1 (Delalande; 11.1 .l972; GB-prior. 3.4.1968). Formulation(s): amp. 80 mg/2 ml; tabl. 200 mg (as maleate) Trade Name(s): F: Vasodistal (Delalande; 1974); wfm I: Vasodistal (Delalande; 1978); wfm J: Anapazin (Zenyaku) Bilbvarde (Yoshindo) Brendil (Daiichi; 198 1) Brentomine (Daito Koeki Nichiiko) Brepanael (Hotta) Sebdeel (Mohan) Cinema (Choseido) Sylpinale (Teikoku Ekarusin (Seiko Eiyo) Kagaku) Madesol (Sanwa) Tatsumedil (Tatsumi) Mishiline (Mishiyama) Tineup (Maruko) Neubeat (Nippon Shoji) Vasodeniel (MF-Taiyo) Prosmet (Sawai) Schulandere (Tsuruhara) Scorojile (Kotobuki) Cinitapride (LAS-17177) ATC: A04 IJse: gastrointestinal RN: 66564-14-5 ME C2,H3,N404 MW: 402.50 CN: 4-amino-N-[l-(3-cyclohcxen-l-ylmelhyl)-4-piperidinyl]-2-ethoxy-5-nitrobenzamide fumarate (1:l) RN: 67135-13-1 MF: C2,H30N404 . C4H404 MW: 518.57 tartrate RN: 96623-56-2 MF: C2,H30N404. xC,H,O, MW: unspecified LD,,: >450 mglkg (M, R, p.0.) 2-ethoxy-4-nitro- benzaic ocid 4-omino-2-ethoxy- 5-nitrobenzoic ocid (1) Cinitopride I Cinmetacin C 477 4-omino-1 -benzyl- pipendine Referencefs): GB 1 574 419 (Anphar; appl. 3.9.1980; GB-prior. 16.11.1976). CH 628 886 (Anphar; appl. 3 1.3.1982; CH-prior. 1.1.1978). synthesis of I: Goldstein, H.; Rrochon, R.: Helv. Chim. Acta (HCACAV) 32, 2334 (1949) synthesis of llkinitapride: DE 2 706 038 (A. Gallardo; appl. 12.2.1977; GB-prior. 17.2.1976). alternative synthesis of cinitapride: ES 2 001 458 (Fordonal; appl. 16.5.1988; E-prior. 12.12 1986). Fonnulation(s): sol. 0.2 mdml (as tartrate); tabl. 1 mg Trade Namefs): E: Cidine (Almirall; 1990) Cinmetacin ATC: MOlAB Use: non-steroidal anti-inflammatory RN: 20168-99-4 MF: C2,H,,N04 MW: 349.39 EINECS: 243-555-6 LD,: 360 rnog (M, i.p.); 750 mglkg (M, p.0.); 590 mglkg (R, i.p.); 1020 mgkg (R, p.0.) CN: 5-methoxy-2-methyl-1-(1-oxo-3-phenyl-2-propenyl)-1H-indole-3-acetic acid (I-methoxypheny1)- cinnomoyl hydrozine hydrochloride chloride levulinic Cinrnetacin acid Reference(s): US3576 800(Sumitomo; 27.4.1971; J-prior. 12.5.1966,27.6.1966,30.6.1966, 8.7.1966, 1.8.1966, 19.8.1966, 15.12.1966, 16.12.1966,20.12.1966,6.1.1967,7.1.1967, 16.1.1967, 17.1.1967). ZA 672 683 (Sumitomo; appl. 12.4.1967; J-prior. 12.5.1966, 27.6.1966.30.6.1977). Yamamolo, H.; Nakao, M.: J. Med. Chem. (JMCMAR) 12, 176 (1969). 478 C Cinnarnedrine Formulation(s): cps 300 mg; suppos. 375 mg, 750 mg Trade Name(s): I: Cindomet (Chiesi); wfm J: Indolacin (Sumitomo) Cinnamedrine (Cinnamylephedrine) ATC: NO2 Use: uterine antispasmodic, treatment of menstrua syndrom RN: 90-86-8 MF: C,,H,,NO MW: 281.40 EINECS: 202-021-2 CN: a-[I-[methyl(3-phenyl-2-propenyl)amino]ethyl]benzenemethanol Ref'erence(s): US 1 959 392 (Winthrop; 1934; D-prior. 1930). Welsh, L.H.; Kennan, G.L.: J. Am. Pharm. Assoc. (JPHAA3) 30, 123 (1941). L-ephedrine cinnamyl Formulatum(s): tabl. 14.9 mg in combination with asp~rine, coffeine Cinnarnedrine Trade Name(s): USA: Midol (Glenbrook)-comb.; w fm (4. v.) bromide Cinnarizine ATC: N07CA02 IJse: antihistaminic, vasodilator RN: 298-57-7 MF: C2,H2,N2 MW: 368.52 EINECS: 206-064-8 LDs,,: 22 mglkg (M, i.v.); >4500 mglkg (M, p.0.); 24 mglkg (R, i.v.); 31500 mg/kg (R, p.0.); >500 mg/kg (dog, p.0.) CN: 1 -(diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine 1 -trans-cinnarnyl- benzhydryl Cinnaririne piperazine chloride Cinolazepam C 479 cinnamyl l-benzhydryl- chloride piperazine Reference(s): US 2 882 271 (Janssen; 14.8.1959; NL-prior. 20.4.1956). DE 1 086 235 (Janssen; appl. 10.4.1957; NL-prior. 20.4.1956). combination with dihydroergotamine: DOS 2 820 937 (Dolorgiet; appl. 12.5.1978). Formularion(s): cps. 75 mg; tab]. 20 mg, 25 mg, 75 mg Trade Name(s): D: Arlevert (Henning)-comb. Cinnacet (Sanofi Winthrop) Cinnarizin forte R.A.N. (R.A.N.) F: Sureptil (Synth6labo)- comb. GB: Stugeron (Janssen-Cilag) I: Cinazyn (Fisons Italchimici) Stugeron (Janssen) Sureptil (Delalande 1snardi)-comb. Toliman (Corvi) J: Annarizine (Sioe) Aplactan (Eisai) Aplexal (Taiyo .Yakuko Takay ama) Apomiterl (Teizo) Apsatan (Wakamoto) Cerebalan (Tohishi) Corathiem (Ohta) Denapol (Teisan) Eglen (Tatsumi) Hirdsyn (Fuso) lzaberizin (Toho) Katoseran (Hishiyama) Milactan (Miwa) Processine (Sankyo) Roin (Maruishi) Salarizine (Iwaki) Sapratol (Daigo-Takeda) Sedatromin (Takcda) Sigma1 (Fuji Zoki) Siptazin (Isei) Spaderizine (Kotobuki) Tolesmin (Sato) Cinolazepam (OX-373) ATC: N05CD13 Use: hypnotic benzodiazepine RN: 75696-02-5 MF: C,,H,,ClFN,O, MW: 357.77 LD,,,: 3.5 glkg (R, p.0.) 3.5 glkg (M, p.o) CN: (+)-7-Chloro-5-(2-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo- 1 H- l,4-benzodiazepine-1 -propanenitrile 2-amino-5-chioro- 2'-fluorobenzophenone (cf, flunitrazeporn synthesis. doxefozepom synthesis) 480 C Cinoxacin 'Polonovski rearrangement" I acetic anhydride / \ 83.5::; (cot.,, CH, n + acrylonitrile, TEBA, triton B Cinolozepom I DE 2 950 235 (Gerot Pharmazeutika; appl. 23.12.1979; A-prior. 18.12.1978). synthesis of intermediate 11: Earley, J.V.; Fryer, R.I.; Winter, D.; Sternbach, L.H.: J. Med. Chem. (JMCMAR) 11 (4), 774 (1968). Formulation(s): tabl. 40 mg Trade Nume($): A: Geroderm (Gerot; 1993) Cinoxacin (Acidum azolinicum; Azolinic acid) ATC: G04AB05 Use: antibacterial (treatment of urinary tract infections) RN: 28657-80-9 MF: C,,H,,,N,O, MW: 262.22 EINECS: 249- 133-8 LD,,,: 900mg/kg(R,i.v.);4160mg/kg.(R, p.0.) CN: 1 -ethyl- l,4-dihydro-4-oxo[l,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid <qz Hz. Pt yq:H3 NaNO,, HCI CH, - 0 sodium 0 O nitrite OH 4.5-rnethylene- 2-amino-4.5- 4-hydroxy- dioxy-2-nitro- rnethylenedioxy- 6.7-rnethylene- acetophenone acetophenone dioxycinnoline (I) . RN: 2388 7-4 6-9 MF: Cz2H,,N3Os MW: 417.51 EINECS: 24 5-9 2 8-9 CN: 1-[ 2-oxo- 2-( l-pyrrolidinyl)ethyl ]-4 -[ l-oxo- 3-( 3,4,5-trimethoxyphcnyl)2-propenyl]pipera~ine maleate (1:l) RN: 2632 8-0 4-1 MF:. 7569 6-0 2-5 MF: C,,H,,ClFN,O, MW: 357.77 LD,,,: 3.5 glkg (R, p.0.) 3.5 glkg (M, p.o) CN: (+ )-7 -Chloro- 5-( 2-fluorophenyl )-2 ,3-dihydro-3-hydroxy-2-oxo- 1 H- l,4-benzodiazepine-1 -propanenitrile. 590 mglkg (R, i.p.); 1020 mgkg (R, p.0.) CN: 5-methoxy-2-methyl- 1-( 1-oxo-3-phenyl-2-propenyl )-1 H-indole-3-acetic acid (I-methoxypheny1 )- cinnomoyl hydrozine hydrochloride chloride levulinic