Etamivan E 791 e Names: Longtussin duplex Fink- GB: comb.; wfrn Ultratussin Fink-comb.; wfm : Camphophyline Millot; as camphersulfonate; wfrn Iodaphyline Millot; as I: iodomethylate; w
Trang 1Etamivan E 791
e Name(s):
Longtussin duplex (Fink)- GB:
comb.; wfrn
Ultratussin (Fink-comb.;
wfm
: Camphophyline (Millot; as
camphersulfonate); wfrn
Iodaphyline (Millot; as I:
iodomethylate); wfrn
MilhCparine(Mil1ot)-comb
with heparin; wfm
: Etamivan
* (Ethamivan)
Dechophyllinc (Millot- Solac)-comb.; wfm lodaphylline (Millot-Solac;
as iodomethylate); wfm Millophyline (Dales; as camphersulfonate); wfm Aricodil (Malesci1)-comb.;
wfm Benzofillina (Courtois; as p-aminobenzoate): wfm
Convivial (Ma1escil)- comb.; wfm
Decofillina (Malesci1)- comb.; wfm
Jod-Melil-Fillina (Malcscil;
as iodomethylate); wfm Spasmodil complex (ABC)-comb.; wfm
ATC: R07AB04 Use: analeptic (central and respiratory stimulant)
RN: 304-84-7 MF: CI2H,,NO, MW: 223.27 EINECS: 206-157-3
LDR: 15 mgkg (M, i.v.); 67 m g k g (M, p.0.);
28 mgkg (R, i.p.1; 17 mglkg (R, i.v.); 154 mglkg (R, p.0.);
30 mgkg (dog, i.v.); 300 mglkg (dog, p.0.)
vanillln d~ethyl- "th~ovond~d" Etomivon
omlne (I)
Reference(s):
US 2 641 612 (Oslerr ~tickstoffwcrke AG; 1953; A-prior 1949)
Fomularion(s): drg 10 mg in comb.; drops 20 mglml in comb
Trade Name(s):
D: Normotin-R rapid (0TW)- GB: Clairvan (Sinclair); wfrn I: Corivanil (Sirt-BBP); wfm
Etamsylate
(Ethamsylate)
ATC: B02BXO1 Usc: hemostatic (capillary protective)
RN: 88-46-0 MF: C6H,0sS MW: 190.18 EINECS: 201-833-4
CN: 2,5-dihydroxyhenzenesulfonic acid
Trang 2792 E Ethacridine
diaethylammonium salt (1:l)
RN: 2624-44-4 MF: C6H60SS.C4111,N MW: 263.31 EINECS: 220-090-7
LD,,: 785 mgtkg (M, i.v.); 8300 mglkg (M, p.0.);
1350 mglkg (R, i.v.); 7500 mglkg (R, p.0.)
p-benzoquinone diethylammonium
hydrogen sulfiie
Etamsylate
u
Reference(s):
GB 895 709 (Lab OM S.A.; appl 31.12.1959; CH-prior 28.1.1959)
Fonmdation(s): amp 250 mg12 ml; tabl 250 mg, 500 mg
Trade Narne(s):
D: Altodor (Deutsche OM) I: Dicynone (Delalande Transil (Malexi)-comb
Ethacridine
(Acrinol; Aethacridin)
ATC: B05CA08; D08AAOI Use: wound antiseptic, intestinal disinfcctant
RN: 442-16-0 MF: Cl,Hl,N,O MW: 253.31 EINECS: 207-130-9
CN: 7-ethoxy-3,9-acridinediamine
lactate (1:l)
RN: 1837-57-6 MF: C,,H,,N,O, C,H60, MW: 343.38 EINECS: 217-408-1
LD,,,: 42 mglkg (M, i.p.); 120 mglkg (M, s.c.)
COOH
+ ~ ~ C u , K2C0, " ~ ~ 1
2-chloro-4-nitro- 4-ethoxyaniline
benzoic acid
2-(4-ethoxy0nilino)-4
nitrobenzoic acid (1)
CI
POCI,
Trang 3Ethambutol E 793
Reference(s):
DRP 360 421 (Hoechst; 1922)
DRP 393 41 1 (Hoechst; 1923)
improved method for 9-amino-2-ethoxy-6-nitroacridine:
DAS 1 952 086 (Hoechst; appl 16.10.1969)
Formulation(s): drg 200 mg; eye drops 1 mglg (as free base); gargle tabl 25 mg (as hydrochloride); ointment
2 mglg; sol 0.1 %; tabl 0.1 g
Trade Name(s):
D: Biseptol (Winzer) numerous combination I: Rivanolo (Tariff
Rivanol (Chinosolfabrik) F: Dentinox (Pharmastra)- J: Hectalin (Daiichi)
Praxis; as acetate) Pyorex (Bail1y)-comb
Use: tuberculostatic RN: 74-55-5 MF: CI,,H,N2O2 MW: 204.31 EINECS: 200-810-6
LD,o: 240 mgkg (M, i.v.); 8700 m g k g (M, p.0.)
dihydrochloride
RN: 1070-1 1-7 MF: C,,H,N202 2HCl MW: 277.24
I-nitropropane form- 2-nitro-
aldehyde 1 -butan01
(+)-2-amino-
1 -butand (I)
racemate resolution with H3C
L(+)-tartoric acid
1
-1.2-dichloro- (+)-2-amino- ethane 1-butanol (11)
H Ethambutol
0
HCI
N H 2 NH2
L-2-amino-
butyric acid
L-ethyl 2-ominobutyrate hydrochloride ( N )
HZ, Raney-Ni or PtO 111 NaOH
Trang 4H3C-xCHI + H3C-CN +
H N CH,
'f
0
1-butene aceto- N-[l -(chlorornethyl)-
nitrile propyl]ocetamide (V)
rocemate resolution with
HCI L(+)-tartaric acid Ill NaOH
Reference(s):
a Wilkinson, R.G et al.: J Am Chem Soc (JACSAT) 83,2212 (1961)
Wilkinson, R.G et a].: J Med Pharm Chcm (JMPCAS) 5, 835 (1962)
US 3 I76 040 (American Cyanamid; 30.3.1965; prior 2.6.1960)
BE 600 640 (American Cyanamid; appl 24.2.1961 ; USA-prior 2.6.1960, 20.12.1960)
BE 6 13 545 (American Cyanamid; appl 6.2.1962; USA-prior 23.1.1962)
racemate resolution of (+)-2-aminobutanol with tartaric acid:
US 3 553 257 (Amcrican Cyanamid; 5.1.1971; prior 16.9.1966)
reaction with 1.2-dichloroethane:
US 3 769 347 (American Cyanamid; 30.10.1973; prior 11.2.1971)
DOS 2 205 269 (American Cyanamid; appl 4.2.1972; USA-prior 11.2.1971)
US 3 944 616 (American Cyanamid; 16.3.1976; prior 29.10.1974)
FR 2 351 090 (Soc Chim Grande Paroisse; appl 11.5.1976)
b DAS 2 446 320 (Denki Kagaku Kogyo; appl 27.9.1974; J-pnor 28.9.1973)
GB 1 469 014 (Denkl Kagaku Kogyo; appl 30.9.1974, J-prior 28.9.1973)
reduction with sodium diethylalum~num hydride:
JP-appl 780 06-127 (Crc co di Rlcerca; appl 22.5.1973; CH-prior 1.3.1973)
c US 3 944 617 (American Cyanamid; 16.3.1976; prior 1.8.1974)
US 3 944 618 (American Cyanamid; 16.3.1976; pr~or 1.8.1974)
US 3 944 619 (American Cyanamid; 16.3.1976; prior 1.8.1974)
GB 1 541 290 (American Cyanamid; appl 9.2.1976)
alternative syntheses:
from I ,2-epoxybutane:
US 3 953 513 (Gruppo Lepetlt; 27.4.1976; GB-prior 29.1 1.1973)
DOS 2 454 950 (Gruppo Lepetit; appl 20.1 1.1974; GB-prior 29.1 1.1973)
DAS 2 410 988 (Polska Akad Nauk Inst Chem Organ.; appl 7.3.1974; PLprior 20.3.1973)
@om 3,4-epoxybutene (butadiene monoxide):
DAS 2 263 7 15 (Soc Farmaceutici Italia; appl 28.12.1972; I-prior 30.12.1971)
from 1 -hydroxy-2-butanone:
DOS 2 547 654 (BASF; appl 24.lO.1975)
asymmetric hydrogenation of 2-acylamino-crotonic acid derivatives:
BE 862 627 (American Cyanamid; appl 4.1.1978; USA-prior 7.1.1977)
DOS 2 800 461 (American Cyanamid; appl 5.1 l978; USA-prior 7.1.1977)
racemate resolution of (+)-2-aminobutanol with (+)-N-benzoyl-trans-2-aminocyclohexanecarboxylic acid:
GB 1 471 838 (Nippon Soda; appl 26.3.1975; J-prior 4.4.1974)
Formulation(s): amp 400 mg14 ml, 1000 mg/lO ml; f c tabl 100 mg, 250 mg, 400 mg, 500 mg (as
dihydrochloride); vial I g
Trade Narne(s):
D: EMB-Fatol (Fatol) Myambutol (Lederle) F: Dexambutol(1,'Arguenon)
Trang 5Ethaverine E 795 Dexambutol-INH I: Etambu (Formulario Naz.) Esanbutol (Lederle) (L'Arguenon)-comb with Etambu (Lifepharma) Ethambutol (Lederle-
Myambutol (Wyeth- Etapiam (Piam) USA: Myambutol (Lederle Labs.;
GB: Myambutol (Lederle); wfm Miambutol (Cyanamid)
Mynak (Leder1e)-comb Miazide (Cyanamid)-comb
with isoniazid; wfm J: Ebutol (Kaken)
Use: antispasmodic RN: 486-47-5 MF: Cz4HzyN04 MW: 395.50 EINECS: 207-633-3
LDso: 45600 ~ g / k g (M, i.v.)
hydrochloride
RN: 985-13-7 MF: C,H,,NO, HCI MW: 431.96 EINECS: 213-573-9
LD,: 86 mglkg (M, i.v.)
1-(3,4-diethoxypheny1)- 3,4-diethoxyphenyl-
2-aminoethanol acetyl chloride
Referencels):
US 1 962 224 (E Wolf; 1934; D-prior 1930)
Formulafion(s): suppos 30 mg in comb (as hydrochloride)
Fade Nnmels):
D: Migdne-Kranit (Krewel
Meuselbach)
F: Etadil (Charpentier); wfrn
Plaquiverine (Monal); wfm
Surparine (Licardy)-comb.;
wfm
1: Azimol ITA (1TA)-comb.;
wfrn
Ceracin (Panthox & Isovex (U.S
Buck)-comb.; wfm Pharmaceutical); wfm Etaverina (Biologici Italia); Laverin (Lemmon); wfm
Predem (Biologici 1talia)- Tensodin (Knoll)-comb.;
USA: Ethaquin (Ascher); wfrn Ethatab (Meyer); wfm
Trang 6796 E Ethchlorvynol
Ethchlorvynol
RN: 113-18-8 MF: C,HyCIO MW: 144.60
LDso: 290 mg/kg (M, p.0.);
55 m g k g (dog, i.v.)
Li, liq NH3
+ H C E C H -b
C I
1 -chloro- acetylene
1 -penten-3-one
ATC: N05CM08 Use: hypnotic, sedative
CI
Ethchlorvynol
Reference(s):
US 2 746 900 (Pfizer; 1956; prior 1953)
McLamore, W.M et al.: J Org Chem (JOCEAH) 20, 109 (1955)
Formulation(s): cps 200 mg, 500 mg, 750 mg
Trade Name(s):
GB: Arvynol (Pfizer); wfm J: Arvynol (Taito Pfizer) USA: Placidyl (Abbott) Serenesil (Abbott); wfm Nostel (Dainippon)
Ethenzamide
(Ethoxy benzamide)
ATC: N02BA07 Use: analgesic
RN: 938-73-8 MF: CyH,,N02 MW: 165.19 EINECS: 213-346-4
LD,,,: 700 mg/kg (M, p.0.);
2630 m g k g (R, p.0.)
CN: 2-ethoxy benzamide
solicylornide diethyl sulfote Ethenzornide
Reference(s):
GB 656 746 (Lundbeck; appl 1948; DK-prior 1947)
Formulation(s): drg 150 mg in comb.; tabl 100 mg in comb
Trade Narne(s):
D: Antifohnon (Siidmedica)- F: CCphil (Boiron)-comb
Glutisal (Ravensberg)- Foscama)-comb
Kolton grippale N (Byk Foscama)-comb
Gulden)-comb J: Amisal (Daiichi)-comb
Ethoxybenzamide (Juzen Kagaku)
Grelan High S (Gre1an)- comb
Grelan Shin A (Grelan) Konjisui Soft (Tanpai)
Trang 7Ethiazide E 797 Pyr~pan A (Tanabe)-comb Sedes A (Shionog~) Synpyrin F (Sumitomo)
Ethiazide
(Aethiazidum)
ATC: C03BA Use: diuretic RN: 1824-58-4 MF: CyH12ClN304S2 MW: 325.80 EINECS: 217-358-0
LD,: >310mg/kg (M, i.v.); > 2 g k g (M, p.0.);
>10 g k g (R, p.0.)
CN: 6-chloro-3-ethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide I, I -dioxide
5-chloro-2,4-di- propionoldehyde
sulfornoylaniline
Referencefs):
GB 861 367 (Ciba; appl 1959; USA-prior 1958)
Trade Name(s):
J: Ethiazide (Tokyo Tanabe);
wfm
/ Ethiazide
Use: hypnotic, sedative RN: 126-52-3 MF: CyH,,N02 MW: 167.21 EINECS: 204-789-4
LD,: 108 mgkg (M, i.v.); 490 mglkg (M, p.0.);
157 mgtkg (R, i.v.); 331 mglkg (R, p.0.);
144 mglkg (dog, i.v.); 190 mglkg (dog, p.0.)
CN: 1-ethynylcyclohexanol carbamate
No, liq NH3
+ H C E C H
cyclo- acetylene
hexanone
l-ethynyl- cyclohexonol
Reference(s):
U S 2 816 910 (Schering; 1957; D-prior 1953)
DE 1 021 843 (Rheinpreussen; appl 1953)
Formulation(s): cps 500 mg
Trade Name(s):
D: Valarnin (Asche); wfm J: Valamin (Schering) USA: Valamid (Dista); wfm
Trang 8798 E Ethinylestradiol
(Aethinylostradiol; Ethinyloestradiol) Use: estrogen (in combination with
progestogen as oral contraceptive) RN: 57-63-6 MF: C,,,H240, MW: 296.41 EINECS: 200-342-2
LD,,,: 1737 mglkg (M, p.0.);
1200 mglkp (R, p.0.)
CN: (1 7a)-19-norpregna- 1,3,5(10)-trien-20-yne-3.17-diol
K or Na,liq NH3
HO
estrone ri Ethlnylestrodiol
(9 v.1
Rcference(s):
Inhoffen, H.H et al.: Ber Dtsch Chem Ges (BDCGAS) 71, 1024 (1938)
DRP 702 063 (Ciba; appl 1938; CH-prior 1937)
Formulation(s): tabl 0.02 mg, 0.025 mg, 0.05 mg; drg 1 mg
Trade Name(s):
D: Riviol (Nourypharma)- Neorlest (Parke-Davis)- Synphasec (Griinentha1)-
Cilest (Janssen-Cilag)- Neo-Stedirile (Wyeth)- Tetragynon (Schering)-
Concephan (Griinentha1)- Non-Ovlon (Jenapharm)- Triette (Brenner-Efeka)-
Diane 35 (Schering)-comb 0slrv-~rimolut (Schcring)- Trinordiol (Wyeth)-comb
Gravistat (Jenapharm) Oviol (Nourypharma)- Turis teron (Jcnapharm)
Leios (Wyeth)-comb Ovoresta (Organon)-comb Yermonil (Novartis
Lovelle (Organon)-comb Ovysmen (Wyeth)-comb Pharma)-comb
Lyndiol (Organon)-comb Perikursal (Wyeth)-comb numerous combination
Marvelon (Organon)-comb Pramino (Janssen-Ci1ag)- preparations
Minisiston (Jenapham- Progynon C (Schering) Cycleane (Monsanto)
Miranova (Schering)-comb Prosiston (Schering)-comb Ethinyl-Estradiol Roussel
MonoStep (Asche)-comb Sequilar (Schering)-comb (Roussel)
Neogynon (Schering)- Sinovula (Asche)-comb Minidril (Wyeth-Lederle)
Trang 9Ethionamide E 799 Tri-Minulet (Wyeth-
Lederle)
generic and numerous
combination preparations
GB: Marvelon (Schering)
numerous combination
preparations
I: Binordiol (Wyeth)-comb
Bivlar (Schering)-comb
Diane (Schering)-comb
Egogyn (Schering)-comb J:
Etinilestradiolo (Amsa)
Eugynon (Schering)-comb
Evanor (Wyeth)-comb USA:
Ginoden (Schering)-comb
Mercilon (Organon 1talia)-
comb
Microgynon (%hering)-
comb
Milvane (Schering)-comb
Minulet (Wyeth)-comb
Novogyn (Schering)-comb
Ovranet (Wyeth)-comb
Planum (Menarini)-comb
Practil (Organon 1talia)- comb
Securgin (Menarini)-comb
Trigynon (Schering)-comb
Triminulet (Wyeth)-comb
Trinordiol (Wyeth)-comb
Trinovum (Ci1ag)-comb
Estrogen (Nichinan Kogyo) Ovahormon Strong (Teikoku Zoki) Alesse (Wyeth-Ayerst) Brevicon (Searle) Demulen (Searle) Desogen (Organon) Estrostep (Parke Davis) Ethynodiol Diacetate and Ethinyl Estradiol (Watson) Levlen (Berlex)
Lo/Ovral (Wyeth-Ayerst) Modicon (Ortho-McNeil Pharmaceutical) Nelova (Warner Chilcott) Nordette (Wyeth-Ayerst) Norethin (Roberts) Norethindrone and Ethinyl Estradiol (Watson) Norinyl (Searle) Ortho-Cept (Ortho-McNeil Pharmaceutical)
Ortho-Cyclen (Ortho- McNeil Pharmaceutical) Ortho Novum (Ortho- McNeil Pharmaceutical) Ortho-Tri-Cyclen (Ortho- McNeil Pharmaceutical) Ovral (Wyeth-Ayerst) Tri-Levlen (Berlex) Tri-Norinyl (Searle) Triphasil (Wyeth-Ayerst)
RN: 536-33-4 MF: C,H,,N,S MW: 166.25 EINECS: 208-628-9
LDs,,: 1 g/kg (M, p.0.);
1320 mgkg (R, p.0.)
diethyl butanone
oxalote
ethyl 2,4-dioxo hexonoate
1 POC13, Pel5
COOH
0 or'cti3
6-ethyl-1.2- dihydra-2-oxo- 4-pyridine- carboxylic acid
ethyl 2-chlaro- 6-ethyl-iso- nicotinote (11)
A
0 or'cH3 C N
ethyl 2- 2-ethyl- Ethionamide
ethyliso- isonicotino-
Trang 10800 E Ethisterone
Referenceis):
GB 800 250 (Chimic et Atomistique; appl 1957; F-prior 1956)
Libermann, S et al.: C R Hebd Seances Acad Sci (COREAF) 242,2409,2412 (1956)
Formulation(s): s c tabl 250 mg; tabl 100 mg
Trade Name(s):
D: Trecator (ThCraplix); wfm J: Ethimide (Tanabe) Thioniden (Kaken)
F: TrCcator (ThCraplix); wfm Ethinamin (Takeda) Tuberrnin (Meiji)
GB: Trescatyl (May & Baker); Itiocide (Kyowa) Tuberoid (Sankyo)
Trescazide (May & Baker)- Teberus (Dainippon) USA: Trecator-SC (Wyeth-
Use: progestogen RN: 434-03-7 MF: Cp,H,,O, MW: 312.45 EINECS: 207-096-5
potassium tert-pentylate
androstenolone acetylene
aluminum
HO tri-tert-butylate
Ethisterone
I
Reference(s):
US 2 272 131 (Ciba; 1942: CH-prior 1937)
Ehrhart, Ruschig 111, 343
alternative synthesis:
US 4 041 055 (Upjohn; 9.8.1977; appl 17.11.1975)
review:
Ullrnanns Encykl Tech Chem., 4 Aufl., Vol 1 3 , 3 0
Formulation(s): cps 50 rng, 100 rng, 250 rng; tabl 25 mg
Trade Name(s):
D: Cycloestrol-A.H Lutogynestryl (Rousse1)-
ProgestCrone (Bruneau); comb.; wfm
ProgestCrone (Bruneau)- Menstrogcn (Organon)- J:
Orastxron (Schering Chemicals); wfm Pre Ciclo (Ibis)-comb.;
wfm Estormon (Hokunku)- comb