CN: 2-[[3-trifluoromethylphenyl]amino]benzoic acid 2-2-hydroxyethoxyethyl ester... flufenornic ocid 2-2-ch1oroethoxy- Etofenornate potossiurn salt ethanol 4, v References: DE 1 939 1
Trang 1Etizolam E 81 1
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
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 m g k g (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
-
NH2
1.3-dihydro- 7-ethyl-2H-thieno- [2.3-el-1,4-
Trang 28 1 2 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):
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 m g k g (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)
0 0
ethyl 3-oxopentanoate 4-hydroxy
butonal
KOH
Etodolac
Trang 3Etodroxizine E 8 1 3
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)
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
+ C I ~ O P O ~ O H - triethylamine
CI
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 m a g (R, i.v.); 292 mglkg (R, p.0.)
CN: 2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid 2-(2-hydroxyethoxy)ethyl ester
Trang 4814 E Etofibrate
+ CI- 0 -OH -
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)
Trade Narne(s):
D: Algesalona (Solvay Traumon (Bayer Vital;
Arzneimittel) 1984)
Rheumon (Bayer Vital; I: Bayrogel (Bayropharm;
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
chloride
Trang 5Etofylline E 815
Trade Narne(s):
D: Lipo-Merz (Merz & Co.;
1974)
(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
ethylene
oxide
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
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
Trang 6816 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
1 sodium ethylate, ethyl formote
( ~ ) - ~ - ( ~ t h ~ ~ ~ ~ ~ ~ b ~ - 2 potassium rhodanide (R)-5-ethoxycar-
imidazole (11)
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-
Radenarcon (ASTA Medica GB: Hypnomidate (Janssen)
AW D) USA: Amidate (Abbott); wfm
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-
Trang 7Etopophos E 817
H ~ C " ~ ~ ' N " - " N >
N-(5-chlorophenyl)-
piperozine
Etoperidone
No, dioxone
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 a s 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
Trang 81 P O C I ~ S H3CYNyCH3 ,
CH3CH3
2 NoHC03 H 2 0 )-
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 m g k g (M, i.v.); 215 mglkg (M, p.0.);
75 m g k g (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
Trang 9Etoposide 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
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
Trang 10820 E Etozolin
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 m g k g (R, p.0.)
[3-methyl-4-oxo-5-(l-piperidinyl)-2-thiazolidinylidene]acetic acid ethyl ester
O\\ / O - ~ ~ s
H ~ c ~ / ~ * ~
h-0 f N n o V C H 3 - I
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)
lidin-2-ylideneacetate
Use: antipsoriatic RN: 54350-48-0 MF: C,,H,,03 MW: 354.49 EINECS: 259-119-3
LD,,: 1176 m g k g (M, i.p.); >2000 mgkg (M, p.0.);
>2000 m g k g (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
methyl