Oxandrolone 0 1511 H2N-OH . HCI, NoOCH, hydroxylomine hydrochloride' 1 H3KOqt3 sodium methylote -, , Reference(s): FR 1 579 495 (R. Aries; appl. 22.1.1968). indometocin Trade Name(s): F: Dinulcid (Lab. I: Flogan (ABC); wfm Pharmascience); wfm Restid (UCB); wfm Oxometacin Oxandrolone (q v.) ATC: A14AA08 Use: anabolic RN: 53-39-4 MF: C,,H,,03 MW: 306.45 EINECS: 200-172-9 LD,,: 1832 mgkg (M, p.0.); >10 gkg (R, p.0.) CN: (5a, 17P)-17-h~droxy-17-methyl-2-oxaandrostan-3-one 3d tetroocetate. osmium tetroxide HOOC& H sodium borohydride I Oxondrolone I Reference(s): US 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 1512 0 Oxaprozin Trade Nameis): J: Vasorome (Kowa) USA: Oxandrin (Bio- Technology) Oxaprozin ATC: MOIAE12 Use: anti-inflammatory RN: 21256-18-8 MF: C,,H,,N03 MW: 293.32 EINECS: 244-296-1 LD,,: 93 mg/kg(M,i.v.); 1210mg/kg(M,p.o.); 82 mgkg (R, i.v.); 4470 mgkg (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). Formulation(s): f. C. tabl. 600 mg Trade Name(s): J: Actirin (Wyeth; 1986) Alvo (Taisho Seiyaku; USA: Daypro (Searle) 1985) Oxatomide ATC: R06AE06 Use: antiallergic RN: 60607-34-3 MF: C,H,,N,O MW: 426.56 EINECS: 262-320-9 LD,,,: 25 mgkg (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) Oxazepam 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). Formulafion(s): susp. 2.6 mg/ml; tabl. 30 mg Trade Name(s): D: Tinset (Janssen-Cilag; GB: Tinset (Janssen; 1982) J: Celtect (Kyowa Hakko; 1982) I: Tinset (Formenti; 1985) 1987) F: Tinset (Janssen-Cilag) Oxazepam ATC: N05BA04 Use: tranquilizer RN: 604-75-1 MF: C15HllCIN,0, MW: 286.72 EINECS: 210-076-9 LD,,: 3700 mgkg (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 6-chloro-2-chloromethyl- 7-chlora-5-phenyl- 4-phenylquinazoline 2-0x0-l,3-dihydro- 3-oxide ZH-1.4-benzodiaze- pine 4-oxide 7-chlaro-5-phenyl- 2-0x0-3-ocetoxy- 1.3-dihydro-ZH-1.4- benzodiazepine (I) Oxozepam I 15 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. I0 mg, 50 mg Trade Name(s): D: Adumbran (Boehringer 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 I: Limbial (Chiesi) Persumbrax (Boehringer 1ng.)-comb. Serpax (Wyeth-Lederle) J: Hilong(Banyu) Wakazepam (Wakamoto) USA: Serax (Wyeth-Ayerst) generics Oxcarbazepine (GP-47680) ATC: N03AF02 Use: anticonvulsant RN: 28721-07-5 MF: C,,H,,N202 MW: 252.27 EINECS: 249-188-8 CN: 10,ll -Dihydro-10-oxo-5H-dibenz[b,flazepine-5-carboxamide 0 0 1. H3~J-oK~~3. cHJcooH 2. Br2. CHC13 H A 0 CH, iminostilbene (I) (c.f. Carbamozepine) H-C-O 1. toluene H,C-0, 10-methoxy-5H- I Oxcarbazepine dibenz[b.f]azepine- 5-carboxomide (In) Oxeladin 0 15 15 1. CI-CN 0 0 2. NaN02, H3CAOKCH3 . CH3COOH I 1. cyonogen chloride I CN 1. H3C-CO-0-OH, CH2CIZ, NaOAc . b O~NH, 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): A: Trileptal (Novartis) CH: Trileptal (Novartis) NL: Trileptal (Novartis) Oxeladin ATC: R05DB09 Use: antitussive RN: 468-61-1 MF: C2,H3,NO3 MW: 335.49 EINECS: 207-418-4 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 citrate (1:l) 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.) 1516 0 Oxetacaine 1. No, liq. NH, 2. H~C-CI QvCN A KOH 2, ethyl chloride benzyl cyanide 2-ethyl-2-phenyl butyronitrile NoOH. Cl*~~CI I b 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). Fortnulation(s): cps. 40 mg (as hydrogen citrate) %:A H3C 2-ethyl-2-phenyl- butyric ocid (1) Trade Narne(s): D: Bronchisan (Amos)- 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. F: Paxtladine (Beaufour) Paxeladine noctee - (Beaufour) I: Neobex (Lampugnani); wfm Notox (Medici)-comb.; wfrn Pectamol (Malesci); wfm Tussiflex (Ita1suisse)- comb.; wfm Tussilisin (Ibirn); wfrn 1: Ethochlon (Hokuriku) Hustopan (Ohta) Neoasdrin (Toa) Neusedan (Nichizo) Tarmina (Mochida) Oxetacaine (Oxethazaine) ATC: C05AD06 Use: gastric mucous membrane anesthetic RN: 126-27-2 MF: CaH4,N303 MW: 467.65 EINECS: 204-780-5 LD,,: 27 mgkg (M, i.p.); 58 mglkg (M, s.c.); 30 mglkg (R, i.p.) CN: 2,2'-[(2-hydroxyethy1)iminol-bis[N-(1 ,l -dimethyl-2-phenylethy1)-N-rnethylacetamide] monohydrochloride RN: 13930-31-9 MF: C28H41N303 . HC1 MW: 504.12 EINECS: 237-698-3 LD5,: 3881 yglkg (M, i.v.); 431 mglkg (M, p.0.); 1400 pg/kg (R, i.v.); 675 mg/kg (R, p.0.) Oxetorone 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,N-'-O~ 2-arninoethonol Formulation(s): susp. (in comb.) 10 mgI5 ml; tabl. 5 mg OH Oxetacaine Trade Narnefs): D: Tepilta (Wyeth)-comb. Mucoxin (Wyeth-Lederle)- Strocain (Eisai) F: Muttsa (Wyeth-Leder1e)- comb. Topicain (Chugai) comb. Mucoxin os sosp. (Wyeth- USA: Oxaine (Wyeth)-comb.; GB: Mucaine (Wyeth)-comb. Leder1e)-comb. wfm I: Emoren (IFI) J: Stomacain (Teisan-Pfizer) Oxetorone ATC: N02CX06 Use: antimigraine agent RN: 26020-55-3 MF: C21H21N02 MW: 319.40 EINECS: 247-41 1-3 CN: 3-benzofuro[3,2-c][l]benzoxepin-6-(l2H)-ylidene-N,N-dimethyl-l-propanamine hydrogen fumarate (1:l) RN: 34522-46-8 MF: Cz1HZINO2, C4H404 MW: 435.48 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- cournariloyl chloride furo[3.2-c][l]benzoxepin (11) 15 18 0 Oxfendazole IT+ 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). Formulation(s): tabl. 60 mg (as hydrogen fumarate) Trade Nam~(s): D: Nocertone (Labaz); wfm F: Nocertone (Sanofi Winthrop) Oxfendazole ATC: P02CA Use: anthelmintic RN: 53716-50-0 MF: C,,H,,N,O,S MW: 315.35 EINECS: 258-714-5 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 + QsN, DMF __* 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 0-OH NO2 0 I QSJX.N~CH3 2. Hz. Pd-c 1. acetic anhydride 11 H . QsClZ: I I 2. peracetic acid 0 0 2-acetomido-4-phenyi- sulfinylnitrobenzene 1.2-diamino-4-phenyl- sulfinylbenzene (11) Oxfendazole Oxiconazole 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): GB: Synanthic (Syntex); wfm Systamex (Wellcome); wfm Oxiconazole ATC: DOIAC11; GOlAF17 Use: antifungal RN: 6421 1-45-6 MF: C,,H,,C14N30 MW: 429.13 CN: (Z)-1-(2,4-dichloropheny1)-2-(1 H-imidazol-1-y1)ethanone 0-[(2,4-dichlorophenyl)methyl]oxime mononitrate RN: 64211-46-7 MF: CIxH,,Cl4N3O. HNO, MW: 492.15 EINECS: 264-730-3 LD,,: 2.63 glkg (M, p.0.); >2.458 glkg (R, p.0.) 2,2',4'-iri- imidozole 1 -(2.4-dichloro- chlorooceta- phenocy1)- phenone imidozole _____, 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). Fonnulation(s): cream 10 mglg; pessaries 600 mg (as mononitrate); powder 10 mglg; sol. 10 mglml Trade Name(s): D: Myfungar (Brenner-Efeka; F: Fonx (Yamanouchi Okinazole (Tokyo Tanabe) 1984) Pharma) USA: Oxistat (Glaxo Wellcome; Oceral (Yamanouchi; 1984) J: Derimine (Kaken) as nitrate) 1520 0 Oxilofrine Oxilofrine ATC: NO~A (p-Hydroxyephedrine; Methylsynephrine; Oxyephedrine) analeptic, sympathomimetic RN: 365-26-4 MF: C,0H15N02 MW: 181.24 EINECS: 206-672-3 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. Fonnulation(s): drg. 16 mg, 32 mg; drops 20 mg/ml, 40 mglml (as hydrochloride) Trade Name(s): D: Carnigen (Albert-Roussel, Hoechst) . 1,3-dihydro-3-hydroxy-5-pheny l-2H-1,4-benzodiazepin-2-one 6-chloro-2-chloromethyl- 7-chlora-5-phenyl- 4-phenylquinazoline 2-0 x0-l,3-dihydro- 3-oxide ZH-1.4-benzodiaze- pine 4-oxide 7-chlaro-5-phenyl-. 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) Oxazepam 0 1513 1 -benzhydryl-. ,S* )-4 -hydroxy-a-[ l -( methylarnino)ethyl]benzenemethanol hydrochloride RN: 94 2-5 1-8 MF: C,oH,sN02 . HCI MW: 217.70 EINECS: 21 3-3 9 2-5 1 -( 4-hydroxy- methyl- Oxilofrine phenyl )-2 -0 x 0- omine