Terbinafine T 1991 process for a polyrnorph: CA 2 173 407 (Acic; appl. 3.4.1993). WO 9 721 705 (Uetikon; appl. 12.12.1996; D-prior. 13.12.1995). US 5 587 377 (Invamed; USA-prior. 24.10.1995). capsules: WO 9 805 308 (Novartis; appl. 31.7.1997; USA-prior. 1.8.1996). pharmaceutical composition for treating glaucoma: W09 531 200 (Senju Pharm.; appl. 15.5.1995; J-prior. 18.5.1994). (R)-(+)-terazosin: W09 200 073 (Abbott; appl. 26.6.1991; USA-prior. 29.6.1990). Formulation(s): cps. (USA) 1 mg, 2 mg, 5 mg, 10 mg; tabl. 1 mg, 2 mg, 5 mg, 10 mg (as monohydrochloride dihydrate) Trade Nameis): D: Flotrin Start (Abbott) Hytrine (Abbott) Vasomet (Mitsubishi) Heitrin (Abbott; 1985) GB: Hytrin (Abbott; 1987) USA: Hytrine (Abbott; 1987) F: Dysalfa (DEbat) J: Hytracin (Dainabot) Terbinafine (SF-86327) ATC: DOlAEI5; DOIBA02; J02AX Use: orally and topically active antifungal RN: 91 161-71-6 MF: C2,H2,N MW: 291.44 LD,,: 393 mglkg (M, i.v.); 4000 mglkg (M, p.0.); >2 glkg (M, s.c.); 213 mdkg (R, i.v.); 4000 rnglkg (R, p.0.); >2 g/kg (R, s.c.); >2 &kg (R, skin) CN: (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-l-naphthalenemethanamine hydrochloride RN: 78628-80-5 MF: C2,H2,N. HCl MW: 327.90 LD,o: >2 @kg (M, s.c.); >2 glkg (R, s.c.); >2 gkg (R, skin) CH3 CIHgLi H,C@CHO + HCEC+CH, -+ HBr, PBrS 1 CH3 butyl- lithium OH acrolein tert-butyl- acetylene I Terbinofine 1 -bromo-6.6-dimethyl- (I -nophthyl- hept-2-en-4-yne (I) rnethyl)methyl- ornine Reference(s): EP 24 587 (Sandoz; appl. 6.8.1980; CH-prior. 22.8.1979). Stiitz, A.; Petranyi, G.: J. Med. Chem. (JMCMAR) 27, 1539 (1984). 1992 T Terbutaline Formulation(s): cream 10 mglg; tabl. 250 mg (as hydrochloride) Trade Name(s): D: Lamisil (Novartis; 1991) I: Daskil (LPB) J: Lamisil (Toko Yakuhin- F: Lamisil (Novartis) Lamisil (Novartis) Sandoz) GB: Lamisil (Novartis; 1990) USA: Lamisil (Novartis) Terbutaline ATC: R03AC03; R03CC03 Use: bronchodilator, tocolytic RN: 23031-25-6 MF: C,,H,,NO, MW. 225.29 EINECS: 245-385-8 CN: 5-[2-[(I, 1 -dimethylethyl)amino]- 1 -hydroxyethyl]- l,3-benzenediol sulfate (2:l) RN: 23031-32-5 MF: C12H19N03. 1/2H2S04 MW: 548.65 EINECS: 245-386-3 LD,,,: 36mg/kg(M,i.v.);205mg/kg(M,p.o.); 69 mglkg (R, i.v.); 8700 mglkg (R, p.0.); 11 6 mglkg (dog, i.v.); 1520 mglkg (dog, p.0.) - N-benzyl-tert- butylarnine 3',5'-dibenzyloxy- acetophenone cHdm H3C~N ___, H,. Pd-C ?Yo Om Terbutaline Refer.ence(s): DE 1 643 296 (Draco; prior. 17.10.1967). GB 1 199 630 (Draco; Lund; appl. 18.10.1967; S-prior. 19.10.1966). US 3 937 838 (Draco; 10.2.1976; prior. 18.10.1967). US 4 01 1 258 (Draco; 8.3.1977; prior. 21.6.1973). Formulation(s): amp. 0.5 mglml, 1 mglml; powder inhaler 0.5 mglpuff; sol. for inhalation 10 mglml (as sulfate); s. r. cps. 7.5 mg; s. r. tabl. 7.5 mg; tabl. 2.5 mg, 5 mg Trade Name(s): D: Aerodur (Astrdpharma- stern) ARUBENDOL (Isis Pharma) Asthmo (Krewel Meuselbach) Asthmoprotect (Azupharma) Bricanyl (pharma-stern; 1971) Bricanyl (Astra)-comb. with guaifenesin Butaliret (Fatol) Butalitab (Fato1)Contimit (Lindopharm) Eudur (Astra)-comb. with theophyllin Terbul (Hexal) Terbutalin (Mundipharma; Stada; Aluid Pharma; ratiopharm) Terbuturmant (Desitin) F: Bricanyl (Astra; 1973) Bricanyl Turbohaler (Astra) GB: Bricanyl (Astra; 1971) I: Bricanyl (Astra) r' Terconazole T 1993 J: Bricanyl (Astra-Fujisawa; Bristurin (Bristol) Brinacyl (Hoechst Marion 1974) USA: Brethine (Novartis; 1975) Roussel; 1974) Terconazole (Triconazole) ATC: GOIAG02 Use: antifungal RN: 67915-31-5 MF: C2,H3,C12N503 MW: 532.47 EINECS: 267-751-6 LD,,: 1741 mgkg (Rm, p.0.); 849 mglkg (Rf, p.0.) CN: cis-l-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-l-ylmethyl)-l,3-dioxolan-4-yl]methoxy]phenyl]-4- (I -methylethyl)piperazine CI OH - HO 1. bromine OH 2. benzoyl chloride 2'.4'-dichloro- glycerol acetophenone I. (iN3 . NOH N-NH CN3 H3C-8-CI 8 2. NoOH 0 1. 1H-1,2,4-triozole CI HO 1 -(4-methoxy- acetone pheny1)piperozine I Terconozole 1994 T Terfenadine Reference(s): DE 2 804 096 (Janssen; appl. 3.8.1978; prior. 31.1.1978). US 4 358 449 (Janssen; 9.11.1982; prior. 21.1 1.1977). US 4 144 346 (Janssen; 13.3.l979; prior. 21.1 1.1977, 31.1.1977). US 4 223 036 (Janssen; 16.9.1980; prior. 8.l.l979,2l.ll.l977,3l.l.l977). Heeres, J. et a].: J. Med. Chem. (JMCMAR) 26, 61 1 (1983). synthesis of 2-bromomethyl-2-(2,4-dichloropheny1)-4-(benzoyloxymethyl)-1,3-dioxolane: Heeres, J. et al.: J. Med. Chem. (JMCMAR) 22, 1003 (1979). Formulation(s): suppos. 80 mg; vaginal cream 0.4 %, 0.8 %; vaginal tabl. 80 mg Trade Name(s): D: Tercospor (Cilag; 1985); I: Terconal (Italchimici) USA: Terazol (Ortho-McNeil; wfm 1988) Terfenadine ATC: R06Ax12 Use: antihistaminic, antiallergic RN: 50679-08-8 MF: C,,H,,NO, MW: 471.69 EINECS: 256-710-8 LD,,,: 5 glkg (M, p.0.); 5 glkg (R, p.0.) CN: a-[4-(1,1-dimethylethyl)phenyl]-4-(hydroxydiphenylmethy1)-1-piperidinebutanol KHC03, KI. toluene + c&cW3 /\ /\ - OH - W3C CH3 azacyclonol (1) 1-(4-tert-butylphenyl)- (q v.1 4-chloro-1 -buton01 Terfenodine KHCO,. KI, NoBH, sodium borohydride Reference(s): DOS 2 303 305 (Richardson-Merrell; appl. 24.1.1973; USA-prior. 28.1.1972). DOS 2 503 362 (Richardson-Merrell; appl. 28.1.1975; USA-prior. 8.2.1974). addition to DOS 2 303 306 (Richardson-Merrell; appl. 28.1.1975; USA-prior. 8.2.1974). GB 1 412 605 (Richardson-Merrell; valid from 15.12.1972; USA-prior. 28.1.1972). US 3 878 217 (Richardson-Merrell; lS.4.1975; appl. 12.7.1973; prior. 28.1.1972). Formulation(s): susp. 30 mg15 ml; s. r. tabl. 60 mg in comb. with pseudoephedrine.HC1; tabl. 60 mg, 120 mg Terodiline T 1995 Trade Narnefs): D: Balkis (Dolorgiet) Terfium (Hexal) J: Triludan (Merrell Dow- Hisfedine (Wolff) Vividrin (Mann) Shionogi) Histaterfen (Azupharma) F: Teldane (Merrell); wfm USA: Seldane (Hoechst Marion Teldane (Hoechst; 1982) Teldane (Richardson- Roussel; 1985) Terfedura (durachemie) Merrell); wfm Terfemundin GB: Triludan (Hoechst) (Mundipharma) I: Teldane (Lepetit); wfm Terodiline ATC: G04BD05 Use: antianginal, calcium antagonist, anticholinergic, treatment of urinary frequency and incontinence RN: 15793-40-5 MF: C,H,N MW: 281.44 CN: N-(l,l-dimethylethyl)-a-methyl-y-phenylbenzenepropanamine hydrochloride RN: 7082-21-5 MF: C2,H,N. HCI MW: 317.90 LD,,: 28 mglkg (M, i.v.); 330 mglkg (M, p.0.); 170 mglkg (M, s.c.) 27 mgkg (R, i.v.); 465 mg/kg (R, p.0.); 370 mglkg (R, s.c.) 63.3 g/kg (dog, p.0.) !.p-diphenylethyl tert-butyl- methyl ketone (I) amine (II) Terodiline I 2. H2. Pd-C I + 11 1. aluminum trichloride Referencefs): a DE 1 170 417 (Aktiebolaget Recip.; appl. 8.1 1.1961; GB-prior. 8.11 .l96O). b HU T32 331 (Richter Gedeon Vegyeszeti Gyar; appl. 30.7.1984; HU-prior. 21.9.1982). Formulation(s): f. c. tabl. 12.5 mg, 25 mg (as hydrochloride) Trade Narnefs): D: Mictrol (Fresenius; 1990); GB: Micturin (Pharmacia & Midurin (Uabi; 1986); wfm wfm Upjohn); wfm J: Mictrol (Kissei; 1988) 1996 T Tertatolol Tertatolol ATC: C07AA16 Use: fhdrenoceptor antagonist, antihypertensive RN: 34784-64-0 MF: C,6H2SN0,S MW: 295.45 CN: (f)-l-[(3,4-dihydro-2H-1-benzothiopyran-8-yl)wxy]-3-(l,l-dimethylethyl)amino]-2-propanol hydrochloride RN: 33580-30-2 MF: CI6H,,NO2S . HC1 MW: 331.91 EINECS: 251-578-8 LD,,,: 120 mglkg (M, i.p.); 37 mg/kg (M, i.v.); 90 mglkg (R, i.p.); 40 mglkg (R, i.v.) 1. PPA 2. Np,, KOH 1. polyphosphoric' acid 2. hydrozine 2-methoxy- 8-chloro- 3-(2-methoxyphenyl thiophenol propianic acid thio)propionic acid B-hydroxy- thiochroman (I) hydrin u Reference(s): DE 2 115 201 (Science Union et Cie.; appl. 29.3.1971; GB-prior. 6.4.1970). US 3 960 891 (Science Union et Cie.; 1.6.1976; GB-prior. 6.4.1970). US 4 032 648 (Science Union et Cie.; 28.6.1977; GB-prior. 6.4.1970). alternative synthesis: GB 1 561 153 (Science Union et Cie.; appl. 23.8.1976). Formulation(s): f. c. tabl. 5 mg (as hydrochloride) Trade Nnme(s): D: Prenalex (Servier; 1990) F: Artex (Servier; Therval; 1990) Testolactone ATC: LO2AX Use: antineoplastic (mamma carcinoma) RN: 968-93-4 MF: C1,H2,01 MW: 300.40 EINECS: 213-534-6 CN: D-homo-17a-oxaandrosta-l,4-diene-3,17-dione dcH3 microbialorjco~ly Cylindracorpon rodicolo (ATCC 1101 1) H H 0 ' progesterone Testoloctone Testosterone T 1997 Reference(s): US 2 744 120 (Olin Mathieson; 1956; appl. 1953). Formulation(s): tabl. 50 mg Trade Name(s): D: Fludestrin (Bristol-Myers I: Teslac (Squibb); wfm USA: Teslac (Bristol-Myers Syuibb) Syuibb) Testosterone ATC: G03BA03 Use: androgen RN: 58-22-0 MF: CI,H,802 MW: 288.43 EINECS: 200-370-5 LD,,: >5 g/kg (M, p.0.) CN: (17P)-17-hydroxyandrost-4-en-3-one undecanoate RN: 5949-44-0 MF: C3,H4,03 MW: 456.71 H2/Roney-Ni or NaBH4 sodium 38-acetoxy- 17-oxo-5- ondroslene (from 16-dehydropregne- nolone ocetote) 1- benzayl chloride & , NoC*(cH3)J3 KOH. 11 cyclo- aluminum hexanone triisopropylote Testosterone I Reference(s): US 2 308 833 (Ciba; 1943; CH-prior. 1935). US 2 308 834 (Ciba; 1943; CH-prior. 1935). US 2 379 832 (Schering Corp.; D-prior. 1936). US 2 387 469 (Ciba; 1945; CH-prior. 1935). starting material: The Merck Index, 12th Ed., 1569 (1996). 1998 T Testosterone cvvionate alternative syntheses: US 2 236 574 (Schering Corp.; 1941, D-prior. 1937). US 2 341 110 (Schering Corp.; 1944, CS-prior. 1939) Formulation(s): cps. 40 mg (as undecanoate); plaster 2.5 mgl37 cm2, 4 mgl40 cm2, 5 mgI44 cm2, 6 mg160 cm2 Trade Name(s): D: Andriol (Organon) I: Mydrotest (Ayerst); wfm Testoviron Depot (Nihon F: Pantestone (Organon SA) Testosterone Tarrico &hering)-comb. Trotoseptine (Boehringer (Mitim); wfm USA: Androderm (SmithKline 1ng.)-comb. J: Androgen Depot (Santen- Beecham) GB: Menopax (Nicholas)- Yamanouchi) Testoderm (Aha) comb.; wfm Enarmon (Teikoku Zoki) Testoral (Organon); wfm Tes-Hol "Z" (Nippon Zoki) Testosterone cypionate ATC: GO~EAO~ (Testosterone cyclopentylpropionate) Use: depot androgen RN: 58-20-8 MF: C2,H4,0, MW: 412.61 EINECS: 200-368-4 LD,,,: >I glkg (M, i.p.) CN: (17~)-17-(3-cyclopentyl-l-oxopropoxy)androst-4-en-3-one pyridine Reference(s): US 2 566 358 (Upjohn; 1951; prior. 1949). DE 896 805 (Upjohn; appl. 1951). Gould, D. et al.: J. Am. Chem. Soc. (JACSAT) 79,4472 (1957). testosterone 3-cyclopentyl- alternative syntheses: US 2 625 556 (Upjohn; 1953; prior. 1949). ES 241 206 (Alter; appl. 1958). US 2 742 485 (Francesco Vismara; 1956; prior. 1954). Testosterone cypionote Formulation(s): vial 200 mglml (10 ml) (4. v) propionyl chloride Trade Name(s): D: Femovirin Amp. (Albert- Rousse1)-comb.; wfm F: Ch. P. T. ThCramex (ThCramex): wfm TestostCrone retard ThCramex (Thtramex; as cyclohexylpropionate); w fm Trioestrine-Retard ThCramex (ThCra.mex)- comb.; wfrn Trioestrine-Retard ThCramex (ThCramex; as cyclohexylpropionate)- comb.; wfm I: Ciclosterone (Farmigea) Clym depositum (Po1i)- comb. Ginandrolo Depositum (Lusofarmaco)-comb. Pertestis-Dep. (Orma) Testorit-Dep. (Gallo) Testosterone Depositum (Lusofarmaco) Testosterone enanthate T 1999 J: Depo Testosteron LISA: Virilon (Star) (Upjohn); wfm Testosterone enanthate ATC: G03EB Use: androgen RN: 315-37-7 MF: C,,H,O, MW: 400.60 EINECS: 206-253-5 LD,: 4 mg/kg (M, i.p.): 2 glkg (R, i.p.1 CN: (l7P)- 17-[(I -oxoheptyl)oxy]androst-4-en-3-one Reference(s): US 2 840 508 (Schering AG; 1958; D-prior. 1951). testosterone enanthic anhydride Formulation(s): amp. 250 mglml; vial 200 mglml, 1 g15 ml Testosterone enanthate Trade Name(s): D: Testosteron-Depot F: Androtardyl (Schering) Primodian Depot (Nihon Jenapharm (Jenapharm) GB: Primoteston Depot Schering)-comb. Testosteron Depot- (Schering Chemicals); wfm Testoviron Depot (Nihon Rotexmedica I: Testo Enant (Geymonat) Schering)-comb. (Rotexmedica) J: Enarmon Depot (Teikoku USA: Delatestryl (Bio- Testoviron Depot Zoki) Technology) (Schering)-comb. (q v.) Testosterone propionate ATC: G03BA03 Use: androgen RN: 57-85-2 MF: C22H3203 MW: 344.50 EINECS: 200-351-1 LD,,: 1350 mgkg (M, p.0.); 1 gkg (R, p.0.) CN: (17B)-17-(1-oxopropoxy)androst-4-en-3-one 0 0 pyridine + testosterone propionic anhydride (4. v.) Testosterane propionate - 2000 T Tetracaine rnlcrobiological dehydroganotion Acetabacter posteurionurn ondrostenediol 17-propionote Reference(s): a CH 206 119 (Ciba; appl. 1936) addition to CH 203 257. DRP 661 384 (Ciba; appl. 1936; CH-prior. 1935). b US 2 236 574 (Schering Corp; 1941; D-prior. 1937). starting material: The Merck Index, 12th Ed., 107 (1996). allernarive .ryntheses: US 2 311 067 (Ciba; 1943; CH-prior. 1939). US 2 374 369 (Ciba; 1945; CH-prior. 1939). US 2 374 370 (Ciba; 1945; CH-prior. 1939). Formulotion(s): amp. 10 mg, 25 mg, 50 mg, 100 mg; amp. 50 mglml, 100 mglml (in comb.); ointment 80 mg1100 mg (in comb.) Trade Name(s): D: Tachynerg (Eberth)-comb. Testosleron Propionat "Eifclfango" (Eifelfango) Testoviron (Schering)- comb. F: Fadiamone (CS)-comb. GB; Sustanon (Organon)-comb. Virormone (Ferring) I: Teslovis (SIT) J: Enarmon Susp. (Teikoku Zoki) Forton (Shionogi) Primodian Inj. (Nihon Schering) Sonyhod M Inj. (Sonybod- Torii) Testinon (Mochida) USA: Androlan (Lannett); wfrn Androlin (Lincoln); wfrn Andrusol-P (Smith, Miller & Patch); wfrn Gy netone (Schering)- comb.; wfrn Neo-Hombre01 (Organon); wfrn Neutron (Myers-Carter)- comb.; wfrn Oreton Propionate (Schering), wfrn Synandrol (Pfizer); wfrn Synerone (Dow); wfrn Testex (Pasadena Res.); wfrn Testodet (Merck Sharp & Dohme); wfrn Testonate (Kay); wtm Tetracaine (Amethncaine) ATC: CO5AD02; D04AB06; NOlBA03; SO1 HA03 Use: local anesthetic RN: 94-24-6 MF: C,,H2,N20, MW: 264.37 EINECS: 202-3 16-6 LD,,,: 6 mglkg (M, i.v.); 300 mglkg (M, p.o.1; 6 mglkg (R, i.v.) CN: 4-(buty1amino)benzoic acid 2-(dimethy1amino)ethyl ester no no hydrochloride RN: 136-47-0 MF: C,511aN202. HC1 MW: 300.83 EINECS: 205-248-5 LD,,,: 6600 ~glkg (M, i.v.); 160 rnglkg (M, p.0.); 4500 pglkg (R, i.v.) . EINECS: 26 7-7 5 1-6 LD,,: 1741 mgkg (Rm, p.0.); 849 mglkg (Rf, p.0.) CN: cis-l-[ 4-[ [ 2-( 2,4-dichlorophenyl )-2 -( 1H-1,2,4-triazol-l-ylmethyl)-l,3-dioxolan-4-yl]methoxy]phenyl ]-4 - (I -methylethyl)piperazine. antihypertensive RN: 3478 4-6 4-0 MF: C,6H2SN0,S MW: 295.45 CN: (f)-l-[(3,4-dihydro-2H-1-benzothiopyran-8-yl)wxy ]-3 -( l,l-dimethylethyl)amino ]-2 -propanol hydrochloride RN: 3358 0-3 0-2 MF: CI6H,,NO2S. CN: (17P )-1 7-hydroxyandrost-4-en-3-one undecanoate RN: 594 9-4 4-0 MF: C3,H4,03 MW: 456.71 H2/Roney-Ni or NaBH4 sodium 38-acetoxy- 17-oxo- 5- ondroslene (from 16-dehydropregne- nolone ocetote)