Pharmaceutical Substances Syntheses, Patents, Applications - Part 203 ppsx

r Thiopental T 2021 topical use for herpes irlfections: US 4 083 991 (Burton, Parsons & Comp.; 1 1.4.1978; appl. 6.5.1977). Formulation(s): sol. 0.0 1 mglrnl Trade Name(s): D: Oxysept (Pharrn-Allergan)- Dermachrome GB: Merthiolate (Lilly); wfm comb. (SynthC1abo)-comb. Otopred (Typharm); wfm F: Collyrex (SmithKline Polyclean (Alcon SA)- I: Lacrigel (Farmigea)-comb. Beecham)-comb. comb. J: Merzonin (Takeda) Constrilia (Alcon SA)- Soaclens (Alcon SA) USA: Merthiolate (Lilly); wfm comb. Vitaseptol (CIBA Vital Ophthalmics) Thiopental ATC: NO1 AF03; N05CA19 Use: narcotic RN: 76-75-5 MF: C,,H,,N20,S MW: 242.34 EINECS: 200-984-3 LD,,: 70 rnglkg (M, i.v.); 600 mglkg (M, p.0.) CN: 5-ethyldihydro-5-(1-methylbutyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione monosodium salt RN: 71-73-8 MF: C,,H,,N2Na0,S MW: 264.33 EINECS: 200-763-1 LDSo: 57 mgkg (M, i.v.); 208 mglkg (M, p.0.); 43.6 mglkg (R, i.v.); 117 mglkg (R, p.0.); 36 mgkg (dog, i.v.) I + NH2 thiourea diethyl ethyl- molonote diethyl ethyl- (1 -methyibutyl)- ( Thiopental molonote (I) Reference(s): US 2 153 729 (Abbott; 1939; appl. 1934). US 2 876 225 (Abbott; 1959; appl. 1956). Formulation(s): vial 0.5 gl20 ml. 1 g120 ml, 2.5 gll 00 ml, 5 gl200 ml Trade Name(s): D: Thiopental "Hycomed" Penthiobarbital Sodique GB: Intraval (May & Baker); (Hycorned) Adrian (Adrian-Marinier); wfm Trapanal (Byk Gulden) wfm Pentothal (Abbott); wfrn F: Nesdonal (Specia); wfm Pentothal (Abbott); wfm I: Farmotal (Pharmacia & Upjohn; as sodium salt) 2022 T 2-Thiophenecarboxylic acid Pentothal (Abbott; as J: Ravonal (Tanahe) USA: Pentothal Sodium sodium salt) Thiobal (Daiichi) (Ohmcda) - - - - 2-Thiophenecarboxylic acid AT~: ~01~x10 Use: antiallergic RN: 527-72-0 MF: C5H40,S MW: 128.15 EINECS: 208-423-4 LD,,,: 1670 mg/kg (M, i.v.) CN: 2-thiophenecarboxplic acid lithium salt RN: 59753-1 6-1 MF: sodium salt RN: 251 12-68-9 MF: potassium salt RN: 3331 1-43-2 MF: magnesium salt RN: 36292-28-1 MF: CSH,Li02S MW: 134.08 EINECS: 261 -9 14-5 CsH3Na0,S MW: 150.13 C,H,KO,S MW: 166.24 C,,II,Mg0,S2 MW: 278.59 thiophene (I) carbomayl 2-thiophene- / 2-Thiophene- I chloride carbaxomide / corboxylic acid 1 2-Thiophena- I + sodium hypobrornite acetic anhydride 2-acetyl- thiophene Reference(s): a DD 13 495 (VEB Hydrierwerk Zeitz; appl. 15.7.1957). b Sy, M.: de Malleray, B.: Bull. Soc. Chim. Fr. (BSCFAS) 1963, 1276 alternative syntheses: Gross, H. et al.: Chem. Ber. (CHREAM) 96, 1382 (1963). DE 1 146 055 (Deutsche Akademie der Wissenschaft; appl. 10.3.1961; DDR-prior. 10.3.1961). Voerman, M.G.L.: Recl. Trav. Chim. Pays-Bas (RTCPA3) 26,293 (1907). use of the magnesium salt us liver protective drug: FR 2 043 477 (Invest. Scientif. Pharmac.; appl. 20.5.1969), Formulution(s): cps. 300 mg (as sodium salt); nasal drops 2.3 % (as sodium salt); tabl. 200 mg (as lithium salt) Trade Name(s): F: Soufrane (Roland-Marie)- Thiophtol (BiogalBniquc); Trophires (Roland-Marie)- comb.; wfm wfm comb.; wfm ThiophCol (Inava); wfm Thiopropazate ATC: N05AB05 Use: neuroleptic RN: 84-06-0 MF: C,H&IN3O2S MW: 446.02 EINECS: 201-513-4 LD,,: llOOmg/kg(M, s.c.) CN: 4-[3-(2-chloro- 10H-phenothiazin- 10-yl)propyl]-1 -piperazineethanol acetate (ester) dihydrochIoride RN: 146-28-1 MF: C2,H2,C1N,02S .2HC1 MW: 518.94 EINECS: 205-666-8 LD,,: 279 mgkg (M, p.0.) Referencefs): US 2 766 235 (J. W. Cusic; 1956; prior. 19.56). perphenozine ocetyl chlaride Formulation(s): tabl. 5 mg, 10 mg (as dihydrochloride) Thiopropazate Trade Namefs): D: Vesitan (Boehringer GB: Dartalan (Searle); wfm Mannh.); wfm (4. v.) Thioproperazine (Thioperazine) ATC: N05AB08 Use: neuroleptlc, anti-emetic RN: 3 16-8 1-4 MF: C22H30N402S, MW: 446.64 EINECS: 206-262-4 LDSo: 70 mglkg (M, i.v.); 830 mglkg (M, p.0.); 25 mglkg (R, 1.v.) CN: N,N-dimethyl- 10-[3-(4-methyl- 1 -piperazinyl)propyl]- 1OH-phenothiazine-2-sulfonamlde dimesylate RN: 2347-80-0 MF: C,2HaN40,SZ . 2CH40,S MW: 638.85 EINECS: 219-074-2 LD,,: 70 mgkg (M, i.v.); 800 mglkg (M, pa); 45 mgkg (R, i.v.); 750 mglkg (R, p.0.) , ddium CI amide 2-dimethylsulfomoyl- I -(3-chloropropyl)- Thioproperazine phenathiazine 4-methylpiperazine 2024 T Thioridazine Reference (s): GB 814 5 12 (RhBne-Poulenc; appl. 15.7.1957; F-prior. 1.8.1956, 18.12.1956). DE 1 088 964 (KhBne-Poulenc; appl. 17.7.1957; P-prior. 1.8.1956, 18.12.1956) Formulation(s): drops 1 mgldrop; tabl. 10 mg, 25 mg (as bismethanesulfonate) Trade Nan~e(s): D: Mayeptil (Rhodia Pharma); GB: Majeptil (May & Baker); USA: Vontil (Smith Klinc & wfm wfm French); wfm F: Majeptil (RhSne-Poulenc J: Cephalmin (Shionogi) Rorer Specia) Thioridazine ATC: NOSAC02 Use: neuroleptic RN: 50-52-2 MF: C2,H26N2S2 MW: 370.59 EINECS: 200-044-2 LD,,,: 385 mdkg (M, p.0.); 7 1 mgkg (R, i.v.); 995 mglkg (R, p.0.) CN: 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-l~~-phenbthiazine monohydrochloride RN: 130-61-0 MF: C2,H2,N2S2. HC1 MW: 407.05 EINECS: 204-992-8 LDS,,: 33 rnglkg (M, i.v.);-360 mglkg (M, pa.); 71 mglkg (R, i.v.); 1060 mglkg (R, p.0.); 160 mgkg (dog, p.0.) tartrate RN: 1257-76-7 MF: C2,HZ6N2S2 . xC,H,O, MW: unspecified Hz"! f 7yOH + yys\cH3 K~CO,, Cu + Q~~~\CH~ COOH 2-chloro- 3-methylthio- N-(3-methylthiopheny1)- benzoic ocid aniline onthranilic acid H 1. sodium omide 3 methyithiodi- 2-methylthio- 2. 2-(2-chloroethy1)- phenylomine (1) phenothiozine 1 -methylpiperidine Reference(s): US 3 239 514 (Sandoz; 8.3.1966; CH-prior. 19.4.1956). Bourquin, J.P. et al.: Helv. Chim. Acta (HCACAV) 41, 1072 (1958) Thioridozine Fornzulation(s): drg. 10 mg, 25 mg, 100 mg; f. c. tabl. 100 mg, 200 mg; s. r. rabl. 30 mg, 200 mg (as hydrochloride); USA: sol. 30 mglml (as free base); tabl. 10 mg, 15 mg, 25 mg, 50 mg, 100mg, 150 mg, 200 mg (as hydrochloride) Trade Nnrne(s): D: Melleretten (ASTA Medica Melleril (Novartis Pharma) Thioridazine-neuraxpharrn AWD) (neuraxpharm) Thiotepa T 2025 F: Melleril (Sandoz) I: Mellerette (Novartis) J: Melleril (Sandoz-Sankyo) GB: Melleril (Novartis) Melleril (Novartis) USA: Thioridazine HCl (Geneva) Thiotepa ATC: LO~ACOI Use: antineoplastic RN: 52-24-4 MF: C6H,,N3PS MW: 189.22 EINECS: 200-135-7 LD,,,: 14500 pglkg (M, i.v.); 38 mglkg (M, p.0.); 9400 pglkg (R, i.v.) CN: 1,1',Iu-phosphinothioylidynetrisaziridine oziridine thiophosphoryl chloride Reference(s): US 2 670 347 (American Cyanamid; 1954; prior. 1952). Formulation(s): vial 15 mg Trade Narne(s): D: Thiotepa "Lederle" GB: Thio-Tepa (Lederle); wfm J: Tespamin (Sumitomo) (Lederle) I: Onco-Tiotepa (Simes); USA: Thioplex (Immunex) F: Thiotkpa Lederle (Lederle) wfm Tiabendazole (Thiabendazole) ATC: DO 1 ACO6; P02CA02 Use: anthelmintic RN: 148-79-8 MF: C,,,H,N3S MW: 201.25 EINECS: 205-725-8 LD,,: 1300 mgkg (M, p.0.); 2080 mgkg (R, p.0.) CN: 2-(4-thiazoly1)- 1 H-benzimidazole o-phenylene- 4-thiazole- / Tiabendazole diornine carboxylic acid Reference(s): US 3 017 415 (Merck & Co.; 16.1.1962; prior. 18.1.1960). alternative methods: US 3 262 939 (Merck & Co.; 26.7.1966; prior. 2.8.1961,4.6.1965). US 3 274 208 (Merck & Co.; 20.9.1966; prior. 18.7.1961, 17.1.1964, 30.8.1965). use as fungicide: US 3 370 957 (Merck & Co.; 27.2.1968; prior. 23.5.1963, 12.5.1964). 2026 T Tiadenol hypophosphite salt: US 3 535 331 (Merck & Co.; 20.10.1970; appl. 26.7.1967) lactate salt: US 3 658 827 (Merck Sharp & Dohme; 25.4.1972; prior. 26.6.1967, 15.6.1970). glycolate: US 4 160 029 (Merck & Co.; 3.7.1979; NL-prior. 10.5.1976) thiazole-4-carboxylic acid: US 3 274 207 (Merck & Co.; 20.9.1966; appl. 2.10.196 1). Formulation(s): chewing tabl. 500 mg; susp. 500 mg15 ml Trade Name(s): D: Minzolum (Sharp & GB: Mintezol (Merck Sharp & J: Mintezol (Banyu) Dohme); wfm Dohme) USA: Mintezol (Merck Sharp & I: Tiabendazolo (IFI) Dohme) Tiadenol ATC: CIOAX03 Use: antihyperlipidemic RN: 6964-20- 1 MF: C,,H,,02S2 MW: 294.52 EINECS: 230-1 65-6 CN: 2,2'-[I ,lo-decanediylbis(thio)]bis[ethanol] R. -CI, -Br 1 .lo-dibromo- 2-rnercopto- Tiodenol decone or ethanol 1 ,lo-dichloro- decone Reference(s): DOS 2 038 836 (Orsymonde; appl. 5.8.1970; GB-prior. 8.8.1969). Forrmdation(s): tabl. 400 mg, 600 mg, 800 mg Trade Name(s): F: Fonlipol (Lafon) 1: Eulip (SIT) Tiabrenolo (NCSN) Tiaden (Malesci) Tiagabine (ABT-569; NO-05-0328) ATC: N03AG06 Use: anticonvulsant, GABA uptake inhibitor RN: 11 5 103-54-3 MF: C20H2SN0,S2 MW: 375.56 CN: (R)-l-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride RN: 145821 -59-6 MF: C,,,H,,NO,S, . HC1 MW: 41 2.02 hydrochloride monohydrate RN: 145821 -57-4 MF: C,,H2SN0,S2~ HCI . H20 MW: 430.03 S-enantiomer Tiagabine T 2027 S-enantiomer hydrochloride RN: 145264-34-2 MF: C2,,H2,NO,S2 . HCI MW: 412.02 racemate RN: 127254-36-8 MF: C20H,sN02S, MW: 375.56 di(3-methyl-2- cyclopropyl- di(3-methyl-2- thienyl) ketone magnesium bromide thienyl)cyclopropyl- corbinol (I) 0 I4 - 11 ethyl nipecotinate Br 4,4-di(3-methyl- 2-thieny1)-3- butenyl bromide 1. NoOH, C2H50H 2. rocemote resolution - 0 Tiagobine Reference(s): WO 8 700 171 (Novo Industri; appl. 26.6.1986; DK-prior. 26.6.1985). preparation of crystalline R-isomer: WO 9 217 473 (Novo Nordisk; appl. 23.3.1992; DK-prior. 4.2.1991). composition with improved stability: WO 96 344 606 (Novo Nordisk; appl. 29.4.1996; DK-prior. 5.5.1995). transdermal delivery system: WO 9 531 976 (Novo Nordisk; appl. 17.5.1995; DK-prior. 20.5.1994). slow release formulation: WO 9 529 665 (Alza Corp.; appl. 14.4.1995; USA-prior. 28.4.1994). Formulation(s): cps. 4 mg, 12 mg, 16 mg, 20 mg; tabl. 5 mg, 10 mg, 15 mg (as hydrochloride) Trade Namels): D: Gabitril (Novo Nordisk) F: Gabitril (Novo Nordisk) USA: Gabitril (Abbott) 2028 T Tiamenidine Tiamenidine ATC: CO2AC Use: antihypertensive RN: 3 1428-61-2 MF: C8HloC1N3S MW: 215.71 CN: N-(2-chloro-4-methyl-3-thienyl)-4,5-dihydro-1H-imidazol-2-amine monohydrochloride RN: 51274-83-0 MF: C,H,,ClN,S . HC1 MW: 252.17 EINECS: 257-100-4 LD,,,: 45 mgkg (M, i.v.1; 400 mglkg (M, p.0.); 170 mgkg (M, s.c.); 40 mglkg (R, i.v.) il methyl iodide 3-amino-2- ammonium N-(2-chloro-4-methyl- S-methyl-N-(2-chloro- chloro-4- thiocyonote 3-thieny1)thiourea 4-methyl-3-thieny1)- methylthiophene isothiouroniurn iodide (1) ethylene diornine 1 Lb "I' "'1 Tiornenidine Reference(s): DE 1 941 761 (Hoechst AG; appl. 16.8.1969). US 3 758 476 (Hoechst AG; 11.9.1973; D-prior. 16.8.1969). Formulation(s): tabl. 0.5 mg, 1 mg (as hydrochloride) Trade Narne(s): D: Sundralen (Delalande; 1988) Tianeptine sodium ATC: N06AX14 Use: tricyclic antidepressant RN: 30123-17-2 MF: C2,H2,ClN,Na04S MW: 458.94 EINECS: 250-059-3 LD,,,: 450 rnglkg (M, i.p.); 900 mglkg (M, p.0.) CN: 7-[(3-chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[cJl[1,2]thiazepin-11-yl)amino]heptanoic acid no nos odium salt free acid RN: 66981-73-5 MF: C,,H2SCIN,04S MW: 436.96 Tiapride T 2029 3-chloro-6-methoxy- N-methyl- corbanylphenyl- aniline sulfonyl chloride 1. KOH, C2HSOH 0 CH3 0 CH3 2. S0Cl2 O.I1 / 1. NoBH, O.ll / 'S-N 3. AICI3 'S-N 2. HCI I- 1. sodium 3. aluminum 0 borohydride CI trichloride 3-chloro-6-methyl- 3.1 1-dichloro-6.1 1 -dihydro- dibenzo[c,f][l ,2]thiozepin- 6-methyldibenzo[c.f]- 1 l(6H)-one S,S-dioxide [1,2]thiazepine S.S-dioxide (11) ethyl 7-ominoheptanoote I Tioneptine sodium 1. CH3N02 + H2NpOVCH3 2. NQOH I1 + 0 1. nitromethone Reference (s): DOS 2 011 806 (Science Union et Cie.; appl. 12.3.1970; GB-prior. 27.3.1969). 0 CH3 kgN/ clw HN "YONa 0 DE 2 065 635 (Science Union et Cie.; appl. 12.3.1970; GB-prior. 27.3.1969). US 3 758 528 (Science Union et Cie.; 11.9.1973; appl. 13.3.1970; GB-prior. 27.3.1969). DE 2 065 636 (Science Union et Cie.; appl. 12.3.1970; GB-prior. 27.3.1969). US 3 821 249 (Science Union et Cie.; 28.6.1974; appl. 30.10.1972). synthesis of 3-chloro-6-methyldibenzo[c,fl[l,2]thiazepin-1 l(6H)-one S,S-dioxide: GB 1 179 109 (Science Union et Cie.; appl. 19.12.1966). medical use for treatment of stress: FR 2 635 461 (ADIR; appl. 18.8.1988). Formulation(s): tabl. 12.5 mg Trade Name(s): F: Stablon (Ardix; 1988) Tiapride ATC: N05AL03 Use: anti-emetic, neuroleptic, antidyskinetic RN: 5101 2-32-9 MF: C,5H24N204S MW: 328.43 EINECS: 256-907-9 CN: N-[2-(diethylamino)ethyl]-2-methoxy-5-(methylsulfonyl)benzamide monohydrochloride RN: 51012-33-0 MF: C,5H,N204S . HC1 MW: 364.89 EINECS: 256-908-4 LDS0: 189 mgkg (M, i.v.); 1340 mglkg (M, p.0.); 254 mgkg (R, i.v.); 4840 mglkg (R, p.0.); 240 mgkg (dog, p.0.) 2030 T Tiaprofenic acid 1. CI-C00-CH2-CH(CH3)2, N(C,H,), COOH 1. isobutyl chloroformate 2. N,N-diethylethylenediomine 2-methoxy-5-methyl- Tiapride sulfonylbenzoic acid DOS 2 327 192 (Soc. d'Etudes Scientif. et Industrielle de I'Ile-de-France; appl. 28.5.1973; F-prior. 1.6.1972, 12.6.1972, 3.4.1973). DOS 2 327 193 (Soc. dtEtudcs Scientif. et Industrielle de I'Ile-de-France; appl. 28.5.1973; F-prior. 1.6.1972, 2.6.1972). FR 2 188 601 (Soc. d'Etudes Scientif. et Industrielle de I'Ile-de-France; appl. 2.6.1972). 2-methoxy-5-methylsulfonylbenzoic acid: US 3 342 826 (Soc. dlEtudes Scientif. et Industrielle d I'Ile-de-France; 19.9.1967; appl. 13.1.1964). Formulation(s): amp. 100 mgl2 ml; tabl. I00 mg (as hydrochloride) Trade Name(s): D: Tiapridex (Synthelabo; Tiapridal (SynthClabo; Luxoben (ASTA Medica) 1978) 1977) Sereprile (Synthelabo) F: Equilium (Fumouzc) I: Italprid (Teofarma) J: Gramalil (Fujisawa) Tiaprofenic acid ATC: MOlAE11 Use: anti-inflammatory RN: 33005-95-7 MF: CI,H,,O,S MW: 260.31 EINECS: 251-329-3 LDso: 690 mg/kg (M, p.0.); 181 mglkg (R, p.0.) CN: 5-benzoyl-a-methyl-2-thiopheneacetic acid " iodide thiophene ethoxalyl 2-thienyl- chloride glyoxalic ocid tin benzoyl chloride (1) chloride I Rcrjerence(s): DOS 2 055 264 (Roussel-Uclaf; appl. 10.1 1.1970; F-prior. 12.1 1.1969). BE 758 741 (Roussel-Uclaf; appl. 10.5.1971; F-prior. 12.1 1.1969). FR 2 1 12 1 l l (Roussel-Uclaf; appl. 4.1 1.1970). US 4 159 986 (Roussel-Uclaf; 3.7.1979; prior. 25.2.1972). . (R, i.v.) il methyl iodide 3-amino- 2- ammonium N-(2-chloro-4-methyl- S-methyl-N-(2-chloro- chloro- 4- thiocyonote 3-thieny1)thiourea 4-methyl-3-thieny1 )- methylthiophene isothiouroniurn. 142 8-6 1-2 MF: C8HloC1N3S MW: 215.71 CN: N-(2-chloro-4-methyl-3-thienyl )-4 ,5-dihydro-1H-imidazol-2-amine monohydrochloride RN: 5127 4-8 3-0 MF: C,H,,ClN,S . HC1 MW: 252.17 EINECS: 25 7-1 0 0-4 . Tiagabine (ABT-569; NO-0 5-0 328) ATC: N03AG06 Use: anticonvulsant, GABA uptake inhibitor RN: 11 5 10 3-5 4-3 MF: C20H2SN0,S2 MW: 375.56 CN: (R)-l-[4,4-bis(3-methyl-2-thienyl )-3 -butenyl ]-3 -piperidinecarboxylic