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Pharmaceutical Substances Syntheses, Patents, Applications - Part 201 potx

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Tetracycline T 2001 ethanol (1) butyl bromide 4-amino- 4-butylamino- Tetracaine benzaic acid benzaic acid 2. Hp, Pd-C 1. butyraldehyde NH2 ethyl 4-amino- benzoate NH2 2-dimethylamino- ethyl 4-amino- benzoote Reference(s): US 1 889 645 (Winthrop; 1932; CH-prior. 1930). Formulation(s): ear drops 5 mglg; in combination preparations: eye drops 6 mglg; sol. 1 gI100 g; spray 5 mglml, 2 % (as hydrochloride) Trade Namefs): D: Acoin (Combustinwerk)- comb. Gingicain M Spray (Hoechst)-comb. Herviros (Herma1)-comb. Ophtocain (Winzer)-comb. Oto-Flexiole (Mann) F: only combination preparations: Amygdospray (Merck- CICvenot) Broncorinol Maux de gorge (Roche Nicholas SA) Cantalene (RPR Cooper) Eludril (Inava) HexomCdine (ThCraplix) Lysofon (L. Laton) Oromkdine (Sanofi Winthrop) Otylol (Bridoux) Solutricine TCtracalne (ThCraplix S A) Tyrcine (Oberlin) GB: Eludril (Chefaro)-comb. Minims amethocaine (Chauvin) I: J: USA: only combination preparations: Corizzina (SIT) Donalg (Dinacren) Butylcain (Tanabe) Recto-reparil (Naturwaren Madaus) Ruscoroid (Inverni della Beffa) Tetocaine (Kyorin) Cetacaine (Cetylite) Tetracycline ATC: A01 AB 13; D06AA04; J01AA07; SOlAA09; S02AA08; S03AA02 Use: antibiotic, antibacterial, antiamebic, antitrichettisal RN: 60-54-8 MF: CzzH,Nz08 MW: 444.44 EINECS: 200-481-9 LD,,: 157 mglkg (M, i.v.); 678 mgkg (M, p.0.); 129 mglkg (R, i.v.); 807 mglkg @, p.0.) CN: [4S-(4a,4aa,5aa,6P, 12aa)]-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a- pentahydroxy-6-methyl- 1 ,l 1 -dioxo-2-naphthacene carboxamide 2002 T Tetracvcline monohydrochloride RN: 64-75-5 MF: C2,H,N20,. HCl MW: 480.90 EINECS: 200-593-8 LDs,,: 157 mg/kg (M, i.v.); 2759 mgkg (M, p.0.); 128 mg/kg (R, i.v.); 6443 mglkg (K, p.0.) phosphate RN: 1336-20-5 MF: unspccified MW: unspecified EINECS: 215-646-0 chlortetracycline I Tetrocycline (9. v.) from fermentation solutions of Streptomyces viridifociens or aureofociens Refe rence(s): a US 2 699 054 (L. H. Conover; 1955; pr~or. 1953). US 3 005 023 (American Cyanamid: 17.10.1961; appl. 5.4.1957). Boothe, J.H. et al.: J. Am. Chem. Soc. (JACSAT) 75,4621 (1953). Conover, L.H. et al.: J. Am. Chem. Soc. (JACSAT) 75,4622 (1963). b US 2 734 018 (American Cyanamid; 1956; prior. 1953). US 2 712 517 (Bristol; 1955; appl. 1954). US 2 886 595 (Bristol; 1959; appl. 1958). US 3 019 173 (American Cyanamid; 30.1.1962; appl. 4.6.1956). pur~fication: US 3 301 899 (Bristol-Myers; 31.1.1967; appl. 27.1 1.1963). synthesis ofpure tetracycline hydrochloride; DE 2 504 347 (DSO, Pharmachim, Sofia; appl. 3.2.1975). contplex with melaphosphoric acid: US 3 053 892 (American Cyanamid; 11.9.1962; appl. 27.4.1960). Formulation(s): cps. 250 mg, 500 mg; cream 30 mglg; f. c. tabl. 500 mg; ointment 30 mglg; vial 500 mg Trade Namers): D: Achromycin (Lederle) Imcx (Merr. & Co.) Mysteclin (Bristol-Myers Squibb)-comb. with amphotericine Polcorton (mephano)- comb. with triamcinolone acetonide Supramycin N (Grunenthal) Tefilin (Hermal) Tetracyclin (Heyl; ratiopharm; Wolff) Tetralution (Merckle) F: Amphocycline (Squibb)- comb. Colicort (Merck Sharp & Dohn~e-Chibret)-comb. Florocycline (SmithKlinc Beecham)-comb. TCtracycline Diarnant (Diamant) numerous combination preparations GB: Achromycin (Wyeth; as hydrochloride) Deteclo (Wyeth)-comb. Topicycline (Monrnouth) 1: Ambramicina (Scharper) Calociclina (ISI) Pensulvit (S1FI)-comb. Spaciclina (SPA) combination preparations 3: Achromy cin (Lederle) Cosa-Tetracyn (Taito Pfizer) Cy tome (Tokyo Tanabe) Junmycin V (Tanabe) Neocycline (Meiji) Tetrazepam T 2003 USA: Achromycin (Lederle) Helidac (Procter & Gamble)-comb. Tetrazepam (Tetrahydrodiazepam) ATC: M03BX07 Use: tranquilizer, skeletal muscle relaxant RN: 10379-14-3 MF: C16H,,CIN20 MW: 288.78 EINECS: 233-837-7 LD,,,: 2 g/kg (M, p.0.) CN: 7-chloro-5-(1-cyclohexen- 1 -yl)- l,3-dihydro- 1-methyl-2H- l,4-benzodiazepin-2-one - -1 CI 1. cyclohexyl- 0 magnesium bromide 2-amino-5- chlorobenzoic acid benzoxozine V 2-amino-5-chloro- glycine ethyl ester phenyl cyclohexyl hydrochloride ketone (I) 7-chloro-5-(1 -cyclohexen- methyl 1-yl)-2-0x0-1,3-dihydro- iodide 2H-1,4-benzodiazepine (111) 7-chloro-5-cyclo- hexyi-2-0x0- 1.3- dihydro-ZH-l.4- benzodiazepine NaOCH3, OMF b DE I 670 620 (Clin-Byla; prior. 5.1.1966). Tetrazepam US 3 426 014 (Clin-Byla; 4.2.1969; F-prior. 9.1.1965,9.4.1965). US 3 551 412 (Clin-Byla; 29.12.1970; F-prior. 8.8.1967). 2004 T Tetroxoprim intermediate (7-chloro-5-cyclohexyl-2-0x0- 1,3-dihydro-2H- l,4-benzodiazepine): US 3 268 586 (Roche; 23.8.1966; prior. 23.8.1960, 16.8.1961). Formulatiort(s): f. c. tabl. 25 mg, 50 mg; tabl. 50 mg Trade Narne(s): D: Mobiforton (Sanofi Muskelat (Azupharma) Tctramdura (durachemie) Winthrop) Myospasmal (TAD) tetrazep (ct-Arzneimittel) Musapam (Krewel Rilex (Lindopharm) F: Myolastan (Sanofi Meuselbach) Tepam-BASF (BASF) Winthrop; 1969) Musaril (Sanofi Winthrop; Tethexal (Hexal) Panos (Lederle) 1981) Tetra-saar (Chephasaar) Tetroxoprim ATC: 501 Use: chemotherapeutic, antibacterial RN: 53808-87-0 MF: C,6H,2N404 MW: 334.38 EINECS: 258-789-4 LD,,,: 192 mglkg (M, i.v.); 1060 mglkg (M, p.0.); 300 mglkg (R, i.v.); 1172 mg/kg (R, p.0.) CN: 5-[[3,5-dimethoxy-4-(2-methoxyethoxy)phenyl]methyl]-2,4-pyrimidinediamine H3c\0-0w;7;H3 + HN Y NH, + H,c-ONo n H3C, 0 NH2 sodium 0 methylate (1) guonidine 1. POCI, 2. NH, OH chloride 2. ommonia (11) Tetroxoprim NH2 I Refer-ence(s): DOS 2 313 361 (Heumann; appl. 17.3.1973). (also further methods) Liebenow, W.; Prikryl, J.: J. Antimicrob. Chemother. (JACHDX) 5, (Suppl. B), 15 (1979). Formulation(s): sol. 25 mg15 ml, 100 mg/5 ml; tabl. 100 mg (in comb. with sulfadiazine) Trade Name(s): D: Sterinor (Heumann)-comb. I: Oxosint (Medivis)-comb. Sterinor (ABC)-comb. Tetryzoline T 2005 Tetryzoline ATC: R01AA06; R01AB03; S01GA02 (Tetrahydrozoline) Use: vasoconstrictor RN: 84-22-0 MF: C13H,,N2 MW: 200.29 EINECS: 201-522-3 LD,,: 48.1 mglkg (M, i.v.); 335 mglkg (M, p.0.) 1 CN: 4,5-dihydro-2-(l,2,3,4-tetrahydro-l-naphthalenyl)-lH-imidazole monohydrochloride RN: 522-48-5 MF: C,,H16N2 . HCI MW: 236.75 EINECS: 208-329-3 LD,,,: 39 mgkg (M, i.v.); 345 mglkg (M, p.0.); 35 mgkg (R, i.v.); 785 mglkg (R, p.0.) 1-cyano- ethylene- tetrolin diarnine Tetryzoline Reference(s): US 2 73 1 47 1 (Sahyun Labs.; 1956; prior. 1954). Formulation(s): eye drops 0.5 mglml; nasal dropslnasal spray 5 mg1lO ml, 10 mg1lO ml, 100 mg1100 ml Trade Name(s): D: Allergopos (Ursapharm) Berberil (Mann) Caltheon (Cephasaar) Diabenyl (Chauvin ankerpharm) Efemolin (CIBA Vision)- F: comb. with flurometholone I: Exrhinin (Pharma . Wemigerode) Rhinopront Spray1 Nasentropfen (Mack, Illert.) Spersadeloxin (CIBA Vision)-comb. Spersallerg (CIBA Vision)- comb. with antazoline hydrochloride Tetrilin (MIP Pharma) Tyzine (Pfizer) Vasapos (Ursapharm) Vidiseptal (Mann) Yxin (Pfizer) Constrilia (Alcon SA) Demetil (Farmila)-comb. Flumetol (Farmila)-comb. Ischemol A (Farmila)- comb. Stilla (Angelini) Tetramil (Farmigea)-comb. Vasorinil (Farmila) Vasosterone (Ange1ini)- comb. Visine (Pfizer) Visublefar~te (Pharmec)- comb. Visumetazone (Pharmec)- comb. Visumicina (Pharmec)- comb. Visustrin (Merck Sharp & Dohme)-comb. J: Narbel (Chugai) USA: Collirium Wyeth (Wyeth)- comb.; wfm Murine (Ross)-comb.; wfm Qzine (Key Pharm.); wfm Tyzine (Pfizer); wfm Thalidomide (K- 17; NSC-66847) Use: anti-inflammatory, immunomodulator, blocker of TNF- production, sedative, treatment of erythema nodosum leprosum RN: 50-35-1 MF: C13Hj0N204 MW: 258.23 EINECS: 200-031-1 LD,,,: >SO00 mgkg (M, p. 0.) CN: 2-(2,6-Dioxo-3-piperidiny1)- 1 H-isoindole-1,3(2H)-dione 2006 T Thalidornide phthalic L-glutarnic anhydride (I) acid N-phthaloyl- glutarnic acid (U) N-phthaloylglutarnic anhydride 0- urea (melt) anhydride 0 0 Thalidornide u 0 0 a-arnino- glutarimide N-phtholayl-L- glutarnine (N) 7. Na,CO,. H,O 2. HCI + 1 A N 0 N-corbethoxy- phthalirnide Keference(s): a GB 768 821 (Chemie Griinenthal; 20.2.1957). CDI. DM? (cot.). THF b 1,l'-carbanyl- diimidazole Kunz, W. ct al.: Arzneim-Forsch. (ARZNAD) 6,426-430 (1956). b JP 5 071 (Dainippon; 13.5.1960). c King, F.E. et al.: J. Chern. Soc. (JCSOA9) 1957,873-880 d Muller, G.W. et al.: Og. Process Res. Dev. (OPRDFK) 3, 139-140 (1999) intravenous administration form for rreartnent of immunologic diseases. EP 908 176 (Gruncnthal; appl. 18.9.1998; D-prior. 6.10.1997) phar-tnuceutical comp. for the treatment of melanomas: US 5 731 325 (Andrulis Pharm.; 24.3.1998; USA-prior. 6.6.1995). use for treating neurocognitive disorderx WO 9 51 7 154 (Andrulis Pharm.; appl. 22.12.1994; USA-prior. 23.12.1993). I Thebacon T 2007 treatment of rheumatoid arthritis: WO 9 504 533 (Andrulis Pharm.; appl. 3.8.1994; USA-prior. 4.8.1993). controlling abnormal concentration of TNF-a: WO 9 214 455 (Rockefeller Univ.; appl. 14.2.1992; USA-prior. 14.2.1991). Trade Name(s): USA: Thalomid (Celgene; 1998) Thebacon (Acethydrocodone) ATC: R05DA10 Use: narcotic, analgesic RN: 466-90-0 MF: C,,H,,N04 MW: 341.41 EINECS: 207-377-2 LD,,: 81 mgkg (M, s.c.) CN: (5a)-6,7-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol acetate (ester) hydrochloride RN: 20236-82-2 MF: C,,H,,N04 . HCI MW: 377.87 EINECS: 243-623-5 Reference(s): a Ehrhart-Ruschig I, 120. b US I 731 152 (C. Schopf; 1929). hydrocodone acetic anhydride Formulation(s): tab1 5 mg (as hydrochloride) Thebacon Trade Name(s): D: Acedicon (Boehringer I: Acedicon (Boehringer lng.); wfm lng.); wfm (q. v.) Thenalidine (Thenaldine) ATC: D04AA03; R06AX03 Use: antihistaminic RN: 86-12-4 MF: C,,H,,N,S MW: 286.44 EINECS: 201-651-5 LD,,: 42 mgkg (M, i.v.); 165 mgkg (M, p.0.); 42 mgkg (R, i.v.); 1060 mglkg (R, p.0.) CN: l-methyl-N-phenyl-N-(2-thienylmethyl)-4-piperidinamine tartrate (1:l) RN: 2784-55-6 MF: C,,H,,N,S . C4H,0, MW: 436.53 EINECS: 220-493-8 2008 T Thenium closilate aniline I -methyl-4- piperidone chloride Reference (s): 7H3 7H3 Hz. Roney-Ni 1 -methyl-4- anilinopiperidine (I) US 2 717 25 1 (Sandoz; 1955; CH-prior. 1951). Formulation(s): drg. 25 mg (as tartrate) Trade Name(s): n: Sandostcn-Calcium F: Sandostkne (Sandoz); wfm (Sandoz); wfm Thenium closilate ATC: ~02 (Theniumclosylat) Use: anthelmintic RN: 4304-40-9 MF: C,,H,NOS - C&C1O3S MW: 454.01 EINECS: 224-3 18-6 CN: N,N-dimethyl-N-(2-phenoxyethyl)-2-thiophenemethinium salt with 4-chlorobenzenesullonic acid (1:l) 2-phenoxyethyl bromide (I) 2-thenyl chloride methyl iodide (11) 2-thenylomine Thenium iodide acetone + Thenium chloride C'- I Thenyldiamine T 2009 ocetone It ti$' B r- N,N-dimethyl-2- Thenium bromide ihenylomine L N-methyl-2- thenylomine Reference(s): GB 864 885 (Wellcome Found.; valid from 1958; prior. 1957). methyl 4-chloro- me: GB 994 742 (Wellcome Found.; valid from 1961; prior. 1960). rhenium closilate Trade Name(s): USA: Bancaris (Burroughs Wellcome); wfm . benzenesulfonate Thenyldiamine ATC: R06 Use: antihistaminic RN: 91-79-2 MF: C,,H,,N,S MW: 261.39 EINECS: 202-098-2 LDSU: 77 mglkg (M, i.p.) CN: N,N-dimethyl-h~-2-pyridinyl-hr-(3-thienymethyl)-1,2-ethanediamine monohydrochloride RN: 958-93-0 MF: Cl,Hl,N3S . HC1 MW: 297.85 EINECS: 213-490-8 LD,,: 12.2 mglkg (M, i.v.); 277 mglkg (M, p.0.); 15 mglkg (R, i.v.); 525 mg/kg (R, p.0.); 10 mgkg (dog, i.v.); 60 mgkg (dog, p.0.) ~ - - - - - - - - - 2-(2-dimethylomino- - - - 5-fhenyl ethylamino)pyridine bromide Thenyldiomine 2010 T Theodrenaline Referencefs): Campaigne, E.; Le Suer, W.M.: J. Am. Chem. Soc. (JACSAT) 71,333 (1949). starting material: US 2 58 1 868 (Monsanto; 1952; prior. 1946). Formulation(s): drops 1 mglml (as hydrochloride) Trade Nanzefs): D: Nebdosator (Winthrop); GB: Bronchilator (1zal)-comb.; I: N.T.R. (Teofarma)-comb. wfm wfm USA: Thenfadil (Winthrop F: Arhumyl (Sterling Haphryn (Winthrop)- Steams); wfm Winthrop)-comb.; wfm comb.; wfm Theodrenaline ATC: C01CA23 Use: circulatory analeptic, diuretic, cardiotonic RN: 13460-98-5 MF: C,,H,,NSO5 MW: 375.39 LD,,,: 1140 mglkg (M, ip.) CN: 7-[2-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6- dione monohydrochloride RN: 2572-61-4 MF: C,,H,,N,O,. HC1 MW: 411.85 EINECS: 219-920-0 I CH3 2-chloro-3',4'-di- (1) hydroxyocetophenone Reference(s): DE 1 119 868 (Degussa; appl. 5.5.1959). US 3 112 313 (Degussa; 26.1 1.1963; D-prior. 5.5.1959). Formulation(s): amp. 10 mgl2 ml, 50 mgIlO ml; f. c. tabl. 5 mg (as hydrochloride in comb. with cafcdrine hydrochloride) . 7-chloro- 5-( 1-cyclohexen- 1 -yl )- l,3-dihydro- 1-methyl-2H- l,4-benzodiazepin-2-one - -1 CI 1. cyclohexyl- 0 magnesium bromide 2-amino- 5- chlorobenzoic acid benzoxozine V 2-amino-5-chloro-. 2-amino-5-chloro- glycine ethyl ester phenyl cyclohexyl hydrochloride ketone (I) 7-chloro- 5-( 1 -cyclohexen- methyl 1-yl )-2 -0 x 0-1 ,3-dihydro- iodide 2H-1,4-benzodiazepine (111) 7-chloro-5-cyclo-. 46 6-9 0-0 MF: C,,H,,N04 MW: 341.41 EINECS: 20 7-3 7 7-2 LD,,: 81 mgkg (M, s.c.) CN: (5a )-6 ,7-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol acetate (ester) hydrochloride RN: 2023 6-8 2-2

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