Etizolam E 81 1 I Etiroxote I Reference(s): DE 1 493 533 (Chemie Griinenthal; appl. 10.4.1964). DAS 1 493 567 (Chemie Griinenthal; appl. 7.10.1965). US 3 930 017 (Chemie Griinenthal; 30.12.1975; D-prior. 7.10.1965). US 4 110 470 (Chemie Griinenthal; 29.8.1978; D-prior. 7.10.1965). Formulation(s): cps. 20 mg Tmde Name(s): D: Skleronorm (Griinenthal); w fm Etizolam ATC: N05BA19; N0SCD Use: benzodiazepine tranquilizer, anxioly tic, sedative RN: 40054-69-1 MF: CI,H,,ClN4S MW: 342.85 LD,: 4258-4358mgkg (M, p.0.); >5000 mglkg (M, LC.); 3619-3509 mgkg (R, p.0.); >5000 mgkg (R, s.c.) CN: 4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2[1,2,4]triazolo[4.3-a][1,4]diazepine 0 2. HBr, CH3COOH 1 1 N-benzyloxycarbonyl- 2'-chlom-2-cyono- butyr- 2-amino-3-(2- glycyl chloride acetophenone aldehyde chlarobenzayl)- 5-ethylthiophene CH3COOH, pyridine - H\1- \ phosphorus - NH2 (I) 5-(2-ch1orophenyl)- (11) 1.3-dihydro- 7-ethyl-2H-thieno- [2.3-el-1,4- diazepin-2-one 812 E Etodolac 1. N2H4 II b 1. hydrazine 0 H Reference(s): Nakanishi, M. et al.: J. Med. Chem. (JMCMAR) 16, 214 (1973). Nakanishi, M. et al.: Arzneim Forsch. (ARZNAD) 22, 1905 (1972). Tahara, T. et al.: Arzneim-Forsch. (ARZNAD) 28, 1153 (1978). DOS 2 229 845 (Yoshitomi; appl. 19.6.1972; J-prior. 18.6.1971,21.6.1971, 30.6.1971, 8.7.1971, 10.7.1971, 13.7.1971). US 3 904 641 (Yoshitomi; 9.9.1975; J-prior. 18.6.1971, 21.6.1971, 30.6.1971, 8.7.1971, 10.7.1971, 13.7.1971). Formulation(s): drops 0.05 %; tabl.0.5 mg, 1 mg Trade Natne(s): I: Depas (Pierrel) Pasaden (Farmades) J: - Depas (Yoshitomi) Etodolac (Etodolic.acid; Etodolsaure) ATC: MOlAB08 LJse: anti-inflammatory, analgesic RN: 41340-25-4 MF: C,,H,,NO, MW: 287.36 LD,,: 593 mgkg (M, p.0.); 94 mgkg (R, p.0.) CN: 1,8-diethyl- l,3,4,9-tetrahydropyrano[3,4-blindole-1 -acetic acid 2-ethyl- aniline 2-ethylbenzene- diazonium chloride 2-ethylphenyl- hydrazine (I) HCI . TosOH 0 0 1 + OHC~OH + b Il ethyl 3-oxopentanoate 4-hydroxy butonal KOH (11) Etodolac Etodroxizine E 813 Referencefs): US 3 939 178 (American Home Products; 17.2.1976; appl. 15.9.1972). US 3 843 681 (American Home Products; 22.10.1974; appl. 1.6.1971). GB 1 391 005 (American Home Products; appl. 1.6.1972; USA-prior. 1.6.1971). DOS 2 226 340 (American Home Products; appl. 30.5.1972; USA-prior. 1.6.1971). FR 2 140 154 (American Home Products; appl. 1.6.1972; USA-prior. 1.6.1971). Demerson, C.A. et al.: J. Med. Chem. (JMCMAR) 18, 189 (1975). Demerson, C.A. et al.: J. Med. Chem. (JMCMAR) 19, 391 (1976). mcemate resolution: US 4 520 203 (American Home Products; 28.5.1985; appl. 16.8.1983). US 4 544 757 (American Home Products; 1.10.1985; appl. 16.2.1984). Formulation(s): cps. 200 mg, 300 mg; s. r. tabl. 400 mg, 600 mg; tabl. 100 mg, 200 mg, 400 mg, 500 mg Trade Name(s): F: Lodine (Wyeth) 1: Edolan (Lepetit; 1987) Ostelac (Wyeth) GB: Lodine SR (Monmouth; Lodine (Wyeth; 1987) USA: Lodine (Wyeth-Ayerst) 1985) J: Hypen (Nippon Shinyaku) Etodroxizine ATC: N05C Use: tranquilizer, hypnotic RN: 17692-34-1 MF: C,,H,,ClN,O, MW: 418.97 LD,: 70 mglkg (M, i.v.); 540 mglkg (M, p.0.); 58 mglkg (R, i.v.); 920 mglkg (R, p.0.) CN: 2-[2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]ethoxy]ethanol Reference(s): GB 817 231 (UCB; appl. 1957; B-prior. 1956). Formularion(s): tabl. 50 mg Trade Name(s): D: Vesparax (UCB)-comb.; F: Drimyl (Cassenne); wfm wfm N(C2H5)3 + CI~O.PO~OH - triethylamine CI 1-(4-chlorobenz- triethylene glycol hydry1)piperozine monochlorohydrin Etofenamate y-O-o-OH CI Etodroxizine ATC: M02AA06 Use: anti-inflammatory (cf. buclizine synthesis) RN: 30544-47-9 MF: C,,H,,F,NO, MW: 369.34 EINECS: 250-231-8 LD,: 75 mglkg (M, i.v.); 743 mglkg (M, p.0.); 139 mag (R, i.v.); 292 mglkg (R, p.0.) CN: 2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester 814 E Etofibrate + CI- -OH 0 flufenornic ocid 2-(2-ch1oroethoxy)- Etofenornate potossiurn salt ethanol (4, v Reference(s): DE 1 939 1 12 (Troponwerke; appl. 1.8.1969). US 3 692 8 18 (Troponwerke; 19.9.1972; D-prior. 1.8.1969). Formulation(s): amp. I gl2 ml; cream 100 mdg; gel 50 mdg; lotion 100 mglg Trade Narne(s): D: Algesalona (Solvay Traumon (Bayer Vital; Arzneimittel) 1984) Rheumon (Bayer Vital; I: Bayrogel (Bayropharm; 1977) 1980) Etofibrate ATC: col~B09 Use: antihyperlipidemic, cholesterol depressant RN: 3 1637-97-5 MF: C,,H,,ClNO, MW: 363.80 EINECS: 250-743- 1 CN: 3-pyridinecarboxylic acid 2-[2-(4-chlorophenoxy)-2-methyl-l-oxopropoxy]etl~yl ester 2-(4-chlorophenoxy)- ethylene 2-methylpropionic glycol acid Reference(s): DOS 1 941 217 (Merz & Co.; appl. 13.8.1969). nicotinoyl DOS 2 519 535 (Alter S.A.; Madrid; appl. 2.5.1975; E-prior. 29.5.1974). DOS 2 53 1 254 (Merz & Co.; 12.7.1975; GB-prior. 5.9.1974). DOS 2 542 413 (Alter S.A.; appl. 23.9.1975; E-prior. 4.6.1975). DOS 2 542 414 (Alter S.A.; appl. 23.9.1975; E-prior. 4.6.1975). US 3 723 446 (Merz & Co.; 27.3.1973; appl. 12.8.1970; D-prior. 13.8.1969). Etofibrote Formulation(s): s. r. cps. 500 mg chloride Etofylline E 815 Trade Narne(s): D: Lipo-Merz (Merz & Co.; 1974) Etofylline ATC: C03BD (Oxyethyltheophylline; Hydroxyathyltheophyllin) Use: cardiotonic, bronchodilator RN: 519-37-9 MF: C,H12N403 MW: 224.22 EINECS: 208-269-8 LD,,: 344 mglkg (M, i.v.); 400 mglkg (M, p.0.); 486 mg/kg (R, i.v.); 710 mglkg (R, p.0.) CN: 3,7-dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-lH-purine-2,6-dione ihcophylline (I) 2-chloroethanol ethylene oxide Etofylline I US 2715 125 (Cane's Chem. Works; 1955; prior. 1953). Formuiation(s): drg. 50 mg, 80 mg in comb. Trade Narne(s): D: Coroverlan (Verla) F: Oxyphylline (Amido); wfm J: Oxyphylline (Sankyo) Eucebral (Siidmedica)- I: Teostallarid (SmithKline comb. Beecham) Etomidate ATC: NOIAX07 Use: anesthetic, hypnotic RN: 33125-97-2 MF: CI,H,,N2O2 MW: 244.29 EINECS: 251-385-9 LD,,,: 29.5 mglkg (M, i.v.); 650 mglkg (M, p.0.); 14.8 mglkg (R, i.v.) CN: (R)-1-(I-phenylethy1)-1 H-imidazole-5-carboxylic acid ethyl ester 816 E Etoperidone (R)-1 -phenyl- ethyl ethylamine chloroocetate (R)-N-(ethoxycarbo- ny1methyl)- 1 -phenyl- ethylamine 1. NaOC2H5. HCOOC2H5. THF H~c>,,D 2. XSCN . HCI 0 " b 1. sodium ethylate, ethyl formote (~)-~-(~th~~~~~~b~- 2. potassium rhodanide (R)-5-ethoxycar- nylmethy1)-N-formyl- bonyl-2-mercopta- 1 -phenylethylomine (I) 1-(1 -phenylethyl)- imidazole (11) I Etamidate I Keference(s): US 3 354 1'73 (Janssen; 21.1 1.1967; prior. 16.4.1964). DAS 1 545 988 (Jansscn; appl. 14.4.196s; USA-prior. 16.4.1964). Janssen, P.A.J. et al.: Arzneim Forsch. (ARZNAD) 21, 1234 (1971). injection solution: DOS 2 937 290 (Janssen; appl. 14.9.1979; USA-prior. 14.9.1978). For~nulation(s): amp. 2 mglml, 20 mgIlO ml Trade Name(s): D: Hypnomidate (Janssen- F: Hypnomidate (Janssen- Cilag) Cilag) Radenarcon (ASTA Medica GB: Hypnomidate (Janssen) AW D) USA: Amidate (Abbott); wfm Etoperidone ATC: N06AB09 Use: antidepressant RN: 52942-3 1-1 MF: C,9H28CINS0 MW: 377.92 CN: 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-4,5-diethyl-2,4-dihydro-3H-1,2,4-triazol-3-one 4,5-diethyl- 1 -bromo-3- 2-(3-chloropropyl)- b5-1 ,2.4- chloropropane 4,5-diethyl-A5- triazolin-3-one (I) 1.2.4-triozolin-3-one (U) Etopophos E 817 H~C"~~'N"-"N> II N(C2H5)3, toluene N-(5-chlorophenyl)- piperozine Etoperidone No, dioxone I + Etoperidone Reference(s): DOS 2 351 739 (Angelini Francesco; appl. 15.10.1973; I-prior. 16.10.1972). US 3 857 845 (Angelini Francesco; 3 1.12.1974; I-prior. 16.10.1972). use as anriparkinsonian: US4 162 318 (Angelini Francesco; 24.7.1979; I-prior. 5.5.1976). US 4 132 79 1 (Angelini Francesco; 2.1.1979; I-prior. 5.5.1976). . combinarion with L-dopa as anriparkinsonian: US4 131 675 (Angelini Francesco; 26.12.1978; prior. 9.2.1978). Formulation(s): cps. 25 mg, 50 mg Trade Name(s): I: Staff (Sigma-Tau); wfm Etopophos (BMY-4048 1-30) ATC: LOlCB Use: antineoplastic (podophyllotoxin derivative) RN: 122405-33-8 MF: C2yH31Na20,6P MW: 712.51 CN: [5R-[5a,5a~,8aa,9~(R*)]]-5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[(4,6-O-ethylidene-~-~- glucopyranosyl)oxy]-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]- 1,3-dioxol-6(5aH)-one disodium salt hexahydrate RN: 151062-35-0 MF: C2,H3,Na2016P. 6H20 MW: 820.60 free acid RN: 117091-64-2 MF: C2,H3,O1,P MW: 668.54 p'3 1. POCI~S H3CYNyCH3 , CH3CH3 2. NoHC03. H20 )- 1. N,N-diisoprapyl- ethylornine 0 H Etopofos CB 2 207 674 (Bristol-Myers Squibb; appl. 3.8.1988; USA-prior. 27.5.1988,4.8.1987). synthesis of'etoposide-4'-phosphate: EP 51 1 563 (Bristol-Myers Squibb; appl. 16.4.1992; USA-prior. 29.4.1991, 20.2.1992). EP 567 089 (Nippon Kayaku; appl. 21.4.1 993; J-prior. 24.4.1992). preparation of'etoposide without extensive purification: EP 652 226 (Bristol-Myers Squibb; appl. 3.11.1994; USA-prior. 4.11.1993). stable hemhydrate with improved storage stability: EP 548 834 (Bristol-Myers Squibb; appl. 18.1 2.1992; USA-prior. 23.12.1991). Formulation(s): vial 100 mg Trade Name(s): USA: Etopophos (Bristol-Myers) Etoposide (VP- 16-21 3) ATC: LOlCBOl Use: antineoplastic, podophyllotoxin derivative RN: 33419-42-0 MF: C2,H320,3 MW: 588.56 EINECS: 251-509-1 LD,,,: 15.07 mgkg (M, i.v.); 215 mglkg (M, p.0.); 75 mgkg (R, i.v.); 1784 mglkg (R, p.0.) CN: [5R-[5a,5a~,8aa,9~(R*)]]-9-[(4,6-0-ethylidene-~-~-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4- hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3 1,3-dioxol-6(5aH)-one Etoposide E 8 19 4'-benzyloxycarbonyi- 4'-demethylepipodo- phyllotoxin (cf. teniposide synthesis) 4.6-0-(R)-ethylidene- 2,3-di-0-acetyl-8-D- glucopyronose 1. Zn(OCDCH3),. NaOCH, 2. Hz. Pd-C I b 1. zinc acetote Etoposide Reference(s): DE 1 643 521 (Sandoz; prior. 9.12.1967). US 3 524 844 (Sandoz; 18.8.1970; CH-prior. 21.6.1965). CH 514 578 (Sandoz; appl. 27.2.1968). Keller-Juseen, C. et a].: J. Med. Chem. (JMCMAR) 14,936 (1971). US 5 637 680 (Nippon Kayaku; 10.6.1997; J-prior. 24.4.1992). EP 778 282 (Nippon Kayaku; appl. 3.12.1996; J-prior. 4.12.1995,8.12.1995). Allevi, P. et al.: J. Org. Chem. (JOCEAH) 58,4175 (1993). Formulation(s): cps. 50 mg, 100 mg; vial 100 mg15 ml, 150 mgl7.5 ml, 500 mg125 ml, 1 g150 ml Trade Narne(s): D: Etomedac (medac) Etoposide Pierre Fabre J: Lastet (Nippon Kayaku; Vepesid (Bristol-Myers (Pierre Fabre) 1987) Squibb; 1980) Vepeside (Novartis) Vepesid (Bristol Squibb; F: Celltop (ASTA Medica) GB: Vepesid (Bristol-Myers 1987) Etopophos (Bristol-Myers Squibb; 1981) USA: Ve Pesid (Bristol-Myers Squibb) I: Vepesid (Bristol It. Sud; Squibb; 1983) 1982); wfm 820 E Etozolin Etozolin ATC: CO3CXO1 Use: diuretic RN: LDso: CN: 7" 73-09-6 MF: CI3H2,N2O3S MW: 284.38 EINECS: 200-794-0 8670 mglkg (M, p.0.); 10250 mgkg (R, p.0.) [3-methyl-4-oxo-5-(l-piperidinyl)-2-thiazolidinylidene]acetic acid ethyl ester O\\ /O-~~s H~c.~/~*~ + NC-O-CH3 N00C2H5 , h-0 fNnoVCH3 -I 0 LC~3 0 0 dimethyl sulfate ethyl mercapto- ethyl cyono- ethyl 4-oxothiazo- acetate acetate lidin-2-ylideneacetate ethyl 3-methyl- 4-oxothiozolidin- 2-ylideneacetate Rejerence(s): US 3 072 653 (Warner-Lambert; 8.1.1963; appl. 6.3.1961). DE 1 160 441 (Warner-Lambert; appl. 21.10.1961; USA-prior. 6.3.1961). GB 1 022 047 (Warner-Lambert; appl. 23.1 1.1962). GB 1 022 048 (Warner-Lambert; appl . 23.1 1.1962). Satzinger, G.: Justus Liebigs Ann. Chem. (JLACBF) 665, 150 (1963). ethyl 5-bromo-3- Formulation(s): tabl. 200 mg, 400 mg Etozolin Trade Name(s): D: Elkapin (Godecke); wfm I: Elkapin (Parke Davis) methyl-4-oxothiazo- 1 lidin-2-ylideneacetate Etretinate ATC: DO5BBO1 Use: antipsoriatic RN: 54350-48-0 MF: C,,H,,03 MW: 354.49 EINECS: 259-119-3 LD,,: 1176 mgkg (M, i.p.); >2000 mgkg (M, p.0.); >2000 mgkg (R, i.p.); >4000 (R, p.0.) CN: (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl ester 1. HCI 2. Zn, HCI HsC-I, KOH + 0=CH2 + methyl HO HO CH3 iodide CH3 '3'3 CH3 3.5-dimethyl- 2J.5-trimethyl- 2.3.5-trimethyl- phenol phenol onisole (1) . 5294 2-3 1-1 MF: C,9H28CINS0 MW: 377.92 CN: 2-[ 3-[ 4-( 3-chlorophenyl )-1 -piperazinyl]propyl ]-4 ,5-diethyl-2,4-dihydro-3H-1,2,4-triazol-3-one 4,5-diethyl- 1 -bromo- 3- 2-( 3-chloropropyl )- b 5-1 . chlarobenzayl )- 5-ethylthiophene CH3COOH, pyridine - H 1- phosphorus - NH2 (I) 5-( 2-ch1orophenyl )- (11) 1.3-dihydro- 7-ethyl-2H-thieno- [2.3-el-1, 4- diazepin-2-one 812 E Etodolac. CN: (R )-1 -( I-phenylethy1 )-1 H-imidazole-5-carboxylic acid ethyl ester 816 E Etoperidone (R )-1 -phenyl- ethyl ethylamine chloroocetate (R)-N-(ethoxycarbo- ny1methyl )- 1 -phenyl- ethylamine