Pharmaceutical Substances Syntheses, Patents, Applications - Part 85 pot

Fenfluramine F 841 monohydrochloride RN: 1892-80-4 MF: C,,H2,N,02 . HCI MW: 377.88 EINECS: 217-580-8 LD,,: 55 mgkg (M, i.v.); 347 mglkg (M, p.0.); 100 rng/kg (R, p.0.) CH3 7-(2-chloroethyl)- 1 -methyl-2- theophylline phenylethylamine CH3 Fenetylline 7-(2-benzylaminoethyI)- phenylaceione theophylline DE 1 123 329 (Degussa; appl. 18.10.1958; addition to DE 1 095 285; appl. 25.9.1956). US 3 029 239 (Degussa; 10.4.1962; D-prior. 17.4.1954). Formulation(s). f. c. tabl. 50 mg (as hydrochloride) Trade Narnefs): D: Captagon (ASTA Medica F: Captagon (Gerda); wfm Captagon (Promdeica); AWD) wfm Fenfluramine ATC: A08AA02 Use: appetite depressant, anorexic RN: 458-24-2 MF: c,,H,-6~,~ MW: 23 1.26 EINECS: 207-276-3 LD,,: 145 mgkg (M, p.0.); 130 rnglkg (R, p.0.); 100 rnglkg (dog, p.0.) CN: N-ethyl-a-methyl-3-(trifluoromethyl)benzeneethanamine hydrochloride RN: 404-82-0 MF: CI2H,,F3N . HC1 MW: 267.72 EINECS: 206-968-2 LD,,: 90 mag (M, i.v.); 170 mg/kg (M, p.0.); 69 mgkg (R, p.0.); 23 mgkg (dog, i.v.); 100 mglkg (dog, p.0.) 842 F Fenipentol H,N-OH pN~oH Hz. Raney-Ni / CH, _____+ hydroxyl- CF3 ornine CF3 Hz, Raney-Ni I + OHC-CH, . ocetoldehyde Reference(s): CF3 Fenfluramine FR-M 1 658 (Science-Union; appl. 4.4.1961; MC-prior. 5.1 1.1960). Formulation(s): cps. 20 mg, 60 mg; s. r. cps. 60 mg; tabl. 20 mg, 40 mg (as hydrochloride) Trade Name(s): D: Ponderax (Boehringer F: PondCral (Biopharma; as Pesos (Valeas) Ing.); wfm hydrochloride) . Ponderal (Servier) Ponderax (Itherapia); wfm GB: Ponderax (Servier); wfm USA: Pondimin (Robins) I: Dimafen (Stroder) Fenipentol ATC: AOSAX Use: choleretic RN: 583-03-9 MF: CIlH,,O MW: 164.25 EINECS: 209-493-9 LDso: 2900 mglkg (M, p.0.); 5432 mgkg (R, p.0.) CN: a-butylbenzenemethanol benzaldehyde butylrnagnesium bromide Fenipentol rn Reference(s): GB 9 15 8 15 (Thomae; appl. 11.4.1960; valid from 6.4.1961). US 3 084 100 (Thomae; 2.4.1963; appl. 30.3.1961). Adams, R.M.; Vander-Werf, C.A.: J. Am. Chem. Soc. (JACSAT) 72,4368 (1950). Engelhorn, R.: Arzneim Forsch. (ARZNAD) 10, 255 (1960). Koss, F.W. et al.: Arzneim Forsch. (ARZNAD) 12, 1026 (1962). Formulation(s): cps. 100 mg Fenofibrate F 843 Trade Name(s): D: Febichol (medphano) I: Critichol (Angelini)-comb. Pentabil (OFF) F: Euralan (Badrial)-comb.; Menabil Complex J: Pancorat (Esai) wfm (Menarini)-comb. Suiclisin (Hikken) Fenofibrate (Procetofene) ATC: COIABOS Use: cholesterol depressant, antihyperlipidemic RN: 49562-28-9 MF: C20H2,CI04 MW: 360.84 EINECS: 256-376-3 LD,,: 1600 mglkg (M, p.0.); >2 glkg (R, p.0.); >4 glkg (dog, p.0.) CN: 2-[4-(4-chlorobenzoyI)phenoxy]-2-methylpropanoic acid I-methylethyl ester 4-chlorobenzoyl chloride 4-chloro-4'-hydroxy- benzophenone (I) 4-chloro-4'-methoxy- benzophenone Reference(s): US 4 058 552 (Orchimed; 15.1 1.1977; CH-prior. 3 1.1.1969). isopropyl olcohol DOS 2 250 327 (Lab. ~ournier; appl. 13.10.1972; GB-prior. 14.10.197 1). Sornay, R. et al.: Arzneim Forsch. (ARZNAD) 26, 885, 889 (1976). EP-appl. 2 151 (Devinter; appl. 10.1 1.1978; F-prior. 14.11.1977). Fenofibrote Formulation(s): cps. I00 mg, 200 mg, 300 mg; s. r. cps. 250 mg Trade Name(s): D: durafenat (durachemie) SCcalip (Biotherapie) Liposit (SIT) Lipanthyl (Fournier GB: Lipantil Micro (Fournier) Nolipax (Salus Research) Pharma; 1978) I: Lipanthyl (Duropharma) Scleril (AGIPS) Lipidil (Fournier Pharma) Lipidax (UCB) Tilene (Francia Farm.) Normalip (Knoll) Lipoclar (Crinos) Volutine (Geymonat) F: Lipanthyl (Fournier; 1975) Lipofene (Teofarma) 844 F Fenoldopam mesilate Fenoldopam mesilate (SKF 82526-5) ATC: COlCA19 Use: antihypertensive RN: 67227-57-0 MF: C,,H,,ClNO,. CH,O,S MW: 401.87 CN: (f)-6-Chloro-2,3,4,5-tetrahydro-l-(4-hydroxyphenyl)-1 H-3-benzazepine-7,8-diol methanesulfonate base RN: 67227-56-9 MF: CI,H16ClN0, MW: 305.76 hydrochloride RN: 181217-39-0 MF: C,,H,,ClNO, . HCI MW: 342.22 1. H3C-NO, H3cy0 / 2. H2 H3C-Onc~~ : C I CHO - CI NH~ 3,4-dimethoxy- 2-chloro-3,4- benzoldehyde dimethoxy- benzoldehyde ethylomine (1) H3C-0 THF, 1 10°C + CI I Fenoldopom mesilote @ intermediole 11 H3C-0 ICH3 OMSO. THF 0 + H~c-s,+ I- n CHO CH3 4-methoxy- trimethylsulfonium benzaldehyde iodide Fenoprofen F 845 tY OH 0-CH3 B2H6. THF 2. B,H6. THF * I - Ill 2-chloro-3.4- dimethoxy- phenylocetonitrile Reference(s): a US 4 160 765 (SmithKline; 10.7.1979; USA-prior. 17.1 1.1976). US 4 171 359 (SmithKline; 16.10.1979; USA-prior. 12.4.1978). aa US 4 197 297 (SmithKline; 8.4.1980; USA-prior. 17.1 1.1976). b Weinstock, J. et al.: J. Med. Chem. (JMCMAR) 23 (9), 973-975 (1980). synergistic antihypertensive compositions; EP 22 330 (SmithKline; appl. 26.6.1980; USA-prior. 10.7.1979). EP 81 006 (SmithKline; appl. 8.12.1981). contmlled release dosage forms comprising separate portions of(R)- and (S)-enantiomers: WO 9 840 053 (Darwin Discovery; appl. 11.3.1998; GB-prior. 11.3.1997). Formulation(s); vial for inj. 10 mglml Trade Name(s): USA: Carlopam (Neurex; 1999) Fenoprofen ATC: MOlAE04 Use: antirheumatic RN: 31879-05-7 MF: ClsH1403 MW: 242.27 EINECS: 250-850-3 LD,: 1400 mgkg (M, p.0.) CN: (f)-a-methyl-3-phenoxybenzeneacetic acid calcium salt dihydrate RN: 53746-45-5 MF: C,,H,CaO, . 2H,O MW: 558.64 LD,,: 471 mgkg (M, i.v.); 439 mgkg (M, p.0.); 526 mglkg (R, i.v.); 415 mgkg (R, p.0.) H3C 0 H3C 0 H3C OH K2C03. Cu NaBH4 ___, & + .@ - sodium OH boronate hon 3'-hydroxy- bromobenzene acetophenone 3'-phenoxy- ocetophenone Par3 oq. NaOH I- phosphorus(lll) bromide Fenoprofen I 846 F Fenoterol Heference(s): DOS 1 941 625 (Lilly; appl. 16.8.1969; USA-prior. l5.8.1968,28.5.1969). US 3 600 437 (Eli Lilly; 17.8.1971; prior. 15.8.1968.9.5.1969, 28.5.1969). alternative syntheses: DOS 2 646 792 (Mitsubishi Petrochemical; appl. 16.10.1976; J-prior. 23.10.1975, 31.7.1976). US 4 016 196 (Nisshin Flour Milling; 5.4.1977; J-prior. 27.7.1974, 29.7.1974). DAS 2 709 504 (Sagami; appl. 4.3.1977; J-prior. 4.3.1976, 27.12.1976). Formulation(s): powder 200 mg, 300 mg; tab]. 300 mg, 600 mg (as calcium salt dihydrate) Trade Name(s): D: Feprona (Lilly; 1975); wfm Progesic (Lilly); wfm J: Fenopron (Shionogi- F: Nalgksic (Lilly) I: Fepron (Lilly) Yamanouchi; 1982) GB: Fenopron (Novex) USA: Nalfon (Dista; 1976) Fenoterol ATC: G02CA03; R03AC04; R03CC04 Use: - bronchodilator RN: 13392-18-2 MF: C,,H,1N04 MW: 303.36 CN: 5-[l-hydroxy-2-[[2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-l,3-benzenediol liydrobromide RN: 1944-12-3 MF: C1,H2,NO,. HBr MW: 384.27 EINECS: 217-742-8 LD,,,: 42 mglkg (M, i.v.); 1990 mglkg (M, p.0.); 65 mglkg (R, i.v.); 1600 mglkg (R, p.0.); 150 mg/kg (dog, p.0.) (11) Fenoterol Fenoverine F 847 Reference(s): DE 1 286 047 (Boehringer Ing.; appl. 30.11.1962). US 3 341 593 (Boehringer Ing.; 12.9.1967; D-prior. 30.11.1962). alternative synrheses: DOS 2 413 102 (Boehringer Ing.; appl. 19.3.1974). Formulation(s): aerosol 0.05 mglpuff in comb; amp. 0.025 mg/ml, 0.5 mg/lO ml; cps. 200 pg; sol. for inhalation 0.5 mglml in comb., 1 mg/ml; tabl. 2.5 mg, 5 mg Tmde Name(s): D: Berodual Aerosol (Boehringer Ing.) Berotec (Boehringer Ing.) Berotec-Dosier-Aerosol (Boehringer Ing.) Ditec (Boehringer Ing.) Partusisten (Boehringer Iw.1 F: Btrotec (Boehringer Ing.; I: Dosberotec (Boehringer as hydrobromide) I%.) BronchoduaI (Boehringer Duovent (Boehringer 1ng.)- Ing.; as hydrobromide) comb. GB: Berotec (Boehringer Ing.; Iprafen (Chiesi)-comb. as hydrobromide) J: Berotec (Boehringer Ing.; Duovent (Boehringer Ing.; as hydrobromide) as hydrobromide) Fenoverine ATC: A03AXO5 Use: antispasmodic RN: 37561 -27-6 MF: C2,H2,N,0,S MW: 459.57 EINECS: 253-552- 1 LD,,: 2874 mgfkg (M, pa) CN: l0-[[4-(1,3-benzodioxol-5-ylmethyl)-l-piperazinyl]acetyl]-10H-phenothiazine phsnothiazine chloroacetyl chloride g H pyridine I -piperonyl- piperazine 10-(ch1oroacetyl)- phenothiazine I Fenoverine Reference(s): FR 2092 639 (A. Buzas, R. Pierre; appl. 3.6.1970). Formulation(s): cps. 100 mg Trade Name(s): F: Spasmopriv (Bouchard) Spasmopriv (VaiIlant- I: Spasmopriv (Lusofarmaco) Defresne) Fenoxazoline ATC: ROlAAI2 Use: vasoconstrictor, local anesthetic RN: 4846-91-7 MF: CI,H,,N20 MW: 218.30 EINECS: 225-437-6 CN: 4,5-dihydro-2-[[2-(1-methylethyl)phenoxy]methyl]-lH-imidazole 848 F Fenoxedil monohydrochloride RN: 23029-57-4 MF: C,,H,,N,O . HCI MW: 254.76 H~C~OH , HCI , , , NC-o 3 - Yo H3C CH, diornine 2-isopropyl- ethyl 2-(2-isopropyl- Fenoxozoline phenoxyoceto- phenoxy)ocetirnidote nitrile hydrochloride Reference(s): FR 1 365 971 (Lab. Dausse; appl. 19.2.1963). US 3 198 703 (Lab. Dausse; 3.8.1965; appl. 4.5.1961). Formulation(s): nasal drops 0.05 %, 0.1 %; nasal spray 1 mg (as hydrochloride) Trade Nume(s): D: Snup (Karlspharma); wfm F: Aturgyl (SynthClabo) DBturgylone (Synthklabo) , Fenoxedil ATC: COlD Use: vasodilator RN: 54063-40-0 MF: C281142N205 MW: 486.65 CN: 2-(4-butoxyphenoxy)-N-(2,5-diethoxyphenyl)-N-[2-(diethylamino)ethyl]acetamide monohydrochloride RN: 27471-60-9 MF: C2,H4,N2OS . HCl MW: 523.1 1 EINECS: 248-478-1 LD,,,: 17mgkg(M,i.v.);750mg/kg(M,p.o.); 10 mgkg (R, i.v.); 2400 mgkg (R, p.0.) H,CV-vO 0 OWCH, (4-butoxyphenoxy)ocetyl 2.5-diethoxy- chloride aniline 1. NoNH2 H3C Pd ______* 0 I. sodium ornide 0,CH3 2. 2-diethylomino- (1) ethyl chloride OwCH3 Fenoxedil Reference(s): DE 1 964712(C.E.R.P.H.A.; appl. 23.12.1969;F-prior. 26.12.1968). US 3 818 021 (C.E.R.P.H.A.; 18.6.1974; F-prior. 24.12.1968). Formulation(s): cps. 100 mg Fenozolone F 849 Trade Name(s): F: Suplexedil (Anphar- Rolland); wfm Suplexedil (L'HCpatrol); wfm Fenozolone (Phenozolone) ATC: N06BA08 Use: psychoanaleptic RN: 1.5302- 16-6 MF: C,,H,,N,O, MW: 204.23 EINECS: 239-339-6 LD,,: 425 mg/kg (M, p.0.) CN: 2-(ethy1amino)-5-phenyl-4(5H)-oxazolone a-chloro- phenylocetyl chloride I Fenozolone I 1 Reference(s): DE 1 297 108 (Lab. Dausse; appl. 20.2.1962; F-prior. 24.2.1961, 23.5.1961, 18.1.1962) Formulation(sJ: tabl. 10 mg Trade Name(sJ: F: Ordinator (Synthelabo) Fenpen tadiol (Phenpentanediol) ATC: N06A; N06B Use: antidepressant RN: 15687-18-0 MF: C12H,,CI0, MW: 228.72 EINECS: 239-782-5 LD,,: 940 mglkg (M, p.0.); 1140 mgkg (R, p.0.) CN: 2-(4-chloropheny1)-4-methyl-2,4-pentanediol ethyl 3-(4-chloro- methylmognesium Fenpentodid phanyl)-3-hydroxybutyrote iodide Reference(s): FR-M 1 984 (Albert Rolland; appl. 26.7.1962). 850 F Fenpiverinium bromide Formulation(s): cps. 100 mg Trade Name(s): F: TrCdum (Anphar-Rolland); TrCdunl (L'HCpatrol); wfm wfrn Fenpiverinium bromide (Fenpipramide methylbromide) ATC: A03AB21 Use: anticholinergic, antispasmodic RN: 125-60-0 MF: CzzHz,BrN,O MW: 417.39 EINECS: 204-744-9 LD,,: 13.5 mglkg (M, i.v.); 800 mglkg (M, pa) CN: 1-(4-amino-4-0x0-3,3-diphenylbuty1)-l -methylpiperidinium bromide 1. NaNH* - 1, sodium ornide 2. 2-piperidinoethyl diphenyl- chloride acetonitrile methyl bromide Referc.nce(s): DE 731 560 (Hoechst; appl. 1941). DE 858 552 (Hoechst; appl. 1950). fenpiprornide (I) Formdation(s): amp. 0.1 mg in comb.; suppos. 0.03 mg, 0.1 mg in comb.; tabl. 0.1 mg in comb. Trade Namc,(s): D: Baralgin (Albert-Rowel)- Baralgin compositum F: Baralgine (Hoechst)-comb.; comb.; wfm (Albert-Rousse1)-comb.; wfm wfm I: Baralgina (Hoechst 1talia)- comb. Fenquizone ATC: C03BAI3 Use: diuretic RN: 20287-37-0 MF: C14H12CIN303S MW: 337.79 EINECS: 243-689-5 CN: 7-chloro- 1,2,3,4-tetrahydro-4-oxo-2-pheny1-6-quinazolinesulfonamide potassium salt RN: 52246-40-9 MF: C14H,,C1KN303S MW: 375.88 . diuretic RN: 2028 7-3 7-0 MF: C14H12CIN303S MW: 337.79 EINECS: 24 3-6 8 9-5 CN: 7-chloro- 1,2,3,4-tetrahydro-4-oxo-2-pheny 1-6 -quinazolinesulfonamide potassium salt RN: 5224 6-4 0-9 MF: C14H,,C1KN303S. (SKF 8252 6-5 ) ATC: COlCA19 Use: antihypertensive RN: 6722 7-5 7-0 MF: C,,H,,ClNO,. CH,O,S MW: 401.87 CN: (f )-6 -Chloro-2,3,4,5-tetrahydro-l-(4-hydroxyphenyl )-1 H-3-benzazepine-7,8-diol methanesulfonate. MW: 303.36 CN: 5-[ l-hydroxy- 2-[ [ 2-( 4-hydroxyphenyl )-1 -methylethyl]amino]ethyl]-l,3-benzenediol liydrobromide RN: 194 4-1 2-3 MF: C1,H2,NO,. HBr MW: 384.27 EINECS: 21 7-7 4 2-8 LD,,,: 42 mglkg