CN: 4,5-diphenyl-2-oxazolepropanoic acid benzoin succinic onhydride Oxaprozin References: DE I 670 005 Wyeth; prior... I 0 mg, 50 mg Trade Names: Ing.; 1965 Azutranquil Azuchemie Du
Trang 1Oxandrolone 0 1511
H2N-OH HCI, NoOCH, hydroxylomine hydrochloride' 1 H 3 K O q t 3
Reference(s):
FR 1 579 495 (R Aries; appl 22.1.1968)
indometocin
Trade Name(s):
Oxometacin
Oxandrolone
( q v.)
Use: anabolic
LD,,: 1832 m g k g (M, p.0.);
>10 g k g (R, p.0.)
3d tetroocetate
osmium tetroxide HOOC&
H
sodium
borohydride
I Oxondrolone I
Reference(s):
U S 3 128 283 (Searle; 7.4.1964; MEX-prior 10.5.1961)
Pappo, R.; Jung, C.J.: Tetrahedron Lett (TELEAY) 1962, 365
starting material:
Counsell, R.E et a].: J Org Chem (JOCEAH) 27, 248 (1962)
Formulation(s): tabl 2.5 mg
Trang 21512 0 Oxaprozin
Trade Nameis):
Technology)
Use: anti-inflammatory
LD,,: 93 mg/kg(M,i.v.); 1210mg/kg(M,p.o.);
82 m g k g (R, i.v.); 4470 m g k g (R, p.0.);
124 mg/kg (dog, i.v.); > 2 glkg (dog, p.0.)
CN: 4,5-diphenyl-2-oxazolepropanoic acid
benzoin succinic
onhydride
Oxaprozin
Reference(s):
DE I 670 005 (Wyeth; prior 17.1 1.1967)
IJS 3 578 671 (Wyeth; 11.5.1971; prior 6.1 1.1967)
Brown, K et al.: Nature (London) (NATUAS) 219, 164 (1968)
Trade Name(s):
1985)
Use: antiallergic
LD,,,: 25 m g k g (M, i.v.); 9596 mglkg (M, p.0.);
29 mglkg (R, i.v.); 1410 mglkg (R, p.0.);
>2 g/kg (dog, p.o.1
CN: 1-[3-[4-(diphenylmethyl)-1-piperazinyl]propyll-1,3-dihydro-2H-ben~.imidazol-2-one
2-benz- 1 -brorno-3- 1 -(3-chloropropyl)-
imidozolone chloropmpone 2-benzimidazolone (I)
Trang 3Oxazepam 0 1513
1 -benzhydryl-
piperozine
Reference(s):
BE 852 405 (Janssen; appl 14.3.1977; USA-prior 21 l2.1976, 2.4.1976)
US 4 250 176 (Janssen; 10.2.1981; prior 6.2.1978)
Trade Name(s):
F: Tinset (Janssen-Cilag)
Use: tranquilizer
LD,,: 3700 m g k g (M, p.0.);
>8 !$kg (R, p.0.)
CN: 7-chloro- 1,3-dihydro-3-hydroxy-5-pheny l-2H-1,4-benzodiazepin-2-one
4-phenylquinazoline 2-0x0-l,3-dihydro-
pine 4-oxide
7-chlaro-5-phenyl- 2-0x0-3-ocetoxy- 1.3-dihydro-ZH-1.4- benzodiazepine (I)
O x o z e p a m
I
Trang 41 5 14 0 Oxcarbazepine
Rej'erence(s):
DE 1 645 904 (American Home Products; prior 17.8.1962)
US 3 176 009 (American Home Products; 30.3.1965; prior 5.3.1962)
US 3 296 249 (American Home Products; 3.1.1967; appl 4.6.1963; prior 29.8.1961,5.3.1962)
DE 1 445 412 (American Home Products; appl 17.8.1962; USA-prior 29.8.1961, 5.3.1962)
DE 1 795 509 (American Home Products; appl 17.8.1962; USA-prior 29.8.1961, 5.3.1962)
Bell, S.C et al.: J Org Chem (JOCEAH) 27,562 (1962)
Bell, S.C.; Childress, S.J.: J Org Chem (JOCEAH) 27, 1691 (1962)
alternative synthesis:
DE 1 295 563 (American Home Products; appl 21.5.1964; USA-prior 29.5.1963, 13.8.1963)
DE 1 300 114 (American Home Products; appl 21.5.1964; USA-prior 29.5.1963, 13.8.1963, 3.12.1963, 7.5.1964)
DE 1 543 325 (American Home Products; appl 21.5.1964; USA-prior 29.5.1963, 31.8.1963, 3.12.1963, 7.5.1964)
DAS 1 795 231 (American Home Products; appl 21.5.1964; USA-prior 29.5.1963, 13.8.1963, 3.12.1963, 7.5.1964)
Bell, S.C et al.: J Org Chem (JOCEAH) 33,216 (1968)
Formulation(s): s r cps 30 mg; tabl I 0 mg, 50 mg
Trade Name(s):
Ing.; 1965)
Azutranquil (Azuchemie)
Durazepam /-forte
(durachemie)
Milfudorm (Merckle)
Noctazepam (Brenner-
Efeka)
Oxahexal (Neuro-Hexal)
Praxiten (Wyeth; 1965) Sigacalm (Kytta-Siegfried) Uskan (Desitin)
generics F: Seresta (Wyeth-Lederle;
1966) GB: Oxanid (Steinhard); wfm Serenid-D (Wyeth); wfm generics
Persumbrax (Boehringer 1ng.)-comb
Serpax (Wyeth-Lederle)
Wakazepam (Wakamoto) USA: Serax (Wyeth-Ayerst) generics
Oxcarbazepine
(GP-47680)
Use: anticonvulsant
CN: 1 0 , l l -Dihydro-10-oxo-5H-dibenz[b,flazepine-5-carboxamide
0 0
1 H 3 ~ J - o K ~ ~ 3 cHJcooH
2 Br2 CHC13
iminostilbene (I)
(c.f Carbamozepine)
dibenz[b.f]azepine-
(In)
Trang 5Oxeladin 0 15 15
1 CI-CN
0 0
2 NaN02, H3CAOKCH3 CH3COOH
I
CN
1 H3C-CO-0-OH, CH2CIZ, NaOAc
O ~ N H , 1 peracetic ocid
corbomozepine (N)
1 CI2, CHCI,
2 DMF & H2SO"VC,
1v -* /
Oxcorbozepine
rn
Oxcorbozepine
=
a DE 2 01 1 087 (Geigy AG; appl 4.3.1970; CH-prior 10.3.1969)
HU 63 389 (Alkaloids; appl 27.12.1991)
WO 9 621 649 (Trifarma; appl 3.1.1996; I-prior 13.1 l995)
b EP 29 409 (Ciba-Geigy AG; appl 24.10.1980; CH-prior 30.10.1979)
EP 28 028 (Ciba-Geigy AG; appl 27.10.1980; CH-prior 30.10.1979)
c CH 633 271 (Ciba-Geigy Ag; appl 18.4.1978; CH-prior 18.4.1978)
d CH 642 950 (Ciba-Geigy AG; appl 30.10.1979; CH-prior 30.10.1979)
Formulation(s): tabl 300 mg, 600 mg
Trade Narne(s):
Use: antitussive
LD,,: 13 mglkg (M, i.v.); 130 mglkg (M, p.0.);
183 mg/kg (R, p.0.)
CN: a,a-diethylbenzeneacetic acid 2-[2-(diethylamino)ethoxy]ethyl ester
RN: 52432-72-1 MF: C2,,H,,NO3 C6H8O7 MW: 527.61 EINECS: 257-910-8
LD,,,: 13 mglkg (M, i.v.); 130 mglkg (M, p.0.);
183 mgikg (R, p.0.)
Trang 61516 0 Oxetacaine
1 No, liq NH,
2 H~C-CI
Q v C N A
KOH
2 , ethyl chloride
benzyl
cyanide
2-ethyl-2-phenyl butyronitrile
NoOH C l * ~ ~ C I
bis(2-chloroethyl) ether
2-(2-chloroethoxy)ethyl
2-ethyl-2-phenylbutyrote (II)
I1
diethylomine
Oxelodin
US 2 885 404 (British Drug Houses; 5.5.1959; GB-prior 4.1.1956)
Petrow, V et al.: J Pharm Pharmacol (JPPMAB) 10,40 (1958)
%:A
H3C
2-ethyl-2-phenyl- butyric ocid (1)
Trade Narne(s):
comb.; wfm
dorex-retard (ICN); wfrn
dorex-retard (Woelrn); wfm
Kontagripp (Azuchemie)-
comb.; wfrn
Mirfusot (Merck1e)-comb.;
wfrn
Pectischoll (Hestia)-comb.;
wfrn
Piniol (Spitzner)-comb.;
w fm
Silopentol (Hormosan);
wfm Stas (Stada)-comb.; wfm Toramin (Athenstaedt)- comb
Paxeladine noctee
- (Beaufour)
wfm Notox (Medici)-comb.;
wfrn
Pectamol (Malesci); wfm Tussiflex (Ita1suisse)- comb.; wfm
Tussilisin (Ibirn); wfrn
Hustopan (Ohta) Neoasdrin (Toa) Neusedan (Nichizo) Tarmina (Mochida)
Oxetacaine
(Oxethazaine)
Use: gastric mucous membrane anesthetic
30 mglkg (R, i.p.)
CN: 2,2'-[(2-hydroxyethy1)iminol-bis[N-(1 , l -dimethyl-2-phenylethy1)-N-rnethylacetamide]
monohydrochloride
LD5,: 3881 yglkg (M, i.v.); 431 mglkg (M, p.0.);
1400 pg/kg (R, i.v.); 675 mg/kg (R, p.0.)
Trang 7Oxetorone 0 1517
( 7 , ) -dimethyl-2-phenyl- chloroacetyl
ethy1)rnethylarnine chloride
2-chloro-N-rnethyl-N- (phenyl-tert-butyl)acetomide (I)
Reference (s):
US 2 780 646 (American Home Products; 1957; prior 1955)
Freed, M.E et al.: J Org Chem (JOCEAH) 26, 2378 (1961)
I + K2C03 ,
H,
'-O~
2-arninoethonol
OH
Oxetacaine
Trade Narnefs):
Use: antimigraine agent
CN: 3-benzofuro[3,2-c][l]benzoxepin-6-(l2H)-ylidene-N,N-dimethyl-l-propanamine
K,CO, KI DMF
phenol 3-bromomethylcoumarilic
acid ethyl ester
(from 3-methylcoumariiic
ocid ethyl ester)
3-phenoxyrnethylcournorilic ocid ethyl ester (1)
3-phenoxyrnethyl- 6-0x0-6,l Z-dihydrabenzo-
Trang 815 18 0 Oxfendazole
I T + CIM9'-'-'-'N/CH3 -*
I CH3
I CH3
3-dimethylominopropyi- 6-hydroxy-6-(3-dimethyl- Oxetorone mognesiurn chloride aminopropy1)-6,12-dihydro-
benzofuro[3.2-c][l]benzoxepin
Reference(s):
DOS 1 963 205 (Labaz; appl 17.12.1969; GB-prior 20.12.1968)
FR-appl 2 026 686 (Labaz; appl 19.12.1969; GB-prior 20.12.1968)
Trade N a m ~ ( s ) :
Winthrop)
Use: anthelmintic
LD,,,: >6.4 glkg (M, route unreported);
>6.4 glkg (R, route unreported);
>I 6 glkg (dog, route unreported)
CN: [S-(phenylsulfiny1)-1 H-benzimidazol-2-yllcarbamic acid methyl ester
CI
2-amino-4-chloro- sodium
nitrobenzene phenylmercaptide
2-amino-4-phenylthio- nitrobenzene (I)
0 0
1 H,c~o"-cH,
1 NoOH
2 HJcJ , cH30n
2-acetomido-4-phenyi- sulfinylnitrobenzene
1.2-diamino-4-phenyl- sulfinylbenzene (11)
Trang 9Oxiconazole 0 1519
Reference(s):
DOS 2 363 351 (Syntex; appl 21.1 1.1973; USA-prior 29.12.1972)
Averkin, G.A et al.: J Med Chem (JMCMAR) 18, 1164 (1975)
Trade Name(s):
Use: antifungal
CN: (Z)-1-(2,4-dichloropheny1)-2-(1 H-imidazol-1-y1)ethanone 0-[(2,4-dichlorophenyl)methyl]oxime mononitrate
LD,,: 2.63 glkg (M, p.0.);
>2.458 glkg (R, p.0.)
2,2',4'-iri- imidozole 1 -(2.4-dichloro-
_, CI
2 2.4-dichloro-
Q OH bemyl chloride
Reference(s):
DOS 2 657 578 (Siegfried AG; appl 18.12.1976; CH-prior 24.12.1975)
US 4 124 767 (Siegfried AG; 7.11.1978; CH-prior 24.12.1975)
GB 1 514 870 (Siegfried AG; appl 23.12.1976; CH-prior 24.12.1975)
FR 2 336 129 (Siegfried AG; appl 23.12.1 976; CH-prior 24.12.1975)
Trade Name(s):
Trang 101520 0 Oxilofrine
sympathomimetic
CN: (R* ,S*)-4-hydroxy-a-[ l -(methylarnino)ethyl]benzenemethanol
hydrochloride
RN: 942-51-8 MF: C,oH,sN02 HCI MW: 217.70 EINECS: 213-392-5
1 -(4-hydroxy- methyl- Oxilofrine
phenyl)-2-0x0- omine
1 -propano1
4'-benzyloxy-
propiophenone
Reference(s):
a DRP 571 229 (I G Farben; appl 1930)
starting material:
DRP 555 404 (I G Farben; appl 1930)
b US 1 877 756 (M Bockmiihl et al.; 1932; D-prior 1929)
US 1 878 021 (Winthrop; 1932; D-prior 1928)
alternative syntheses:
DRP 526 393 (I G Farben; appl 1928)
DRP 597 123 (I G Farben; appl 1928)
review:
Ehrhart, Ruschig, Vol 2, 154
Trade Name(s):
Hoechst)