SE440505B - Nya oxazolin-steroid-derivat, sett for framstellning derav och anvendning derav vid framstellning av kortikosteroider - Google Patents
Nya oxazolin-steroid-derivat, sett for framstellning derav och anvendning derav vid framstellning av kortikosteroiderInfo
- Publication number
- SE440505B SE440505B SE8105686A SE8105686A SE440505B SE 440505 B SE440505 B SE 440505B SE 8105686 A SE8105686 A SE 8105686A SE 8105686 A SE8105686 A SE 8105686A SE 440505 B SE440505 B SE 440505B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- group
- methyl
- compounds
- double bonds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- -1 OXAZOLINE STEROID Chemical class 0.000 title claims description 10
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002576 ketones Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- IJWRHVPBIVEEQB-OBQKJFGGSA-N (8r,9s,10r,13s,14s,17r)-17-(2-bromoacetyl)-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CBr)[C@@H]4[C@@H]3CCC2=C1 IJWRHVPBIVEEQB-OBQKJFGGSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- JEAYUBBKDZTAGJ-VPSDZCSPSA-N (8R,9S,10R,13S,14S)-17-(1-isocyanoethylidene)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene Chemical compound [N+](#[C-])C(C)=C1CC[C@H]2[C@@H]3CC=C4C=C(CC[C@]4(C)[C@H]3CC[C@]12C)OC JEAYUBBKDZTAGJ-VPSDZCSPSA-N 0.000 description 1
- WSIQEGIPGPEMTC-TXTPUJOMSA-N (8r,9s,10r,13s,14s)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C WSIQEGIPGPEMTC-TXTPUJOMSA-N 0.000 description 1
- QSSNXCGGHSSHJJ-UHFFFAOYSA-N 1-diethoxyphosphoryl-1-isocyanoethane Chemical compound CCOP(=O)(OCC)C(C)[N+]#[C-] QSSNXCGGHSSHJJ-UHFFFAOYSA-N 0.000 description 1
- IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8023575A FR2493324B1 (nl) | 1980-11-05 | 1980-11-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8105686L SE8105686L (sv) | 1982-05-06 |
| SE440505B true SE440505B (sv) | 1985-08-05 |
Family
ID=9247684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8105686A SE440505B (sv) | 1980-11-05 | 1981-09-25 | Nya oxazolin-steroid-derivat, sett for framstellning derav och anvendning derav vid framstellning av kortikosteroider |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4401596A (nl) |
| JP (1) | JPS57106700A (nl) |
| AT (1) | AT386602B (nl) |
| CH (1) | CH652726A5 (nl) |
| DE (1) | DE3144009A1 (nl) |
| DK (1) | DK162771C (nl) |
| FI (1) | FI72526C (nl) |
| FR (1) | FR2493324B1 (nl) |
| GB (1) | GB2086907B (nl) |
| HU (1) | HU183666B (nl) |
| IT (1) | IT1171613B (nl) |
| NL (1) | NL8104985A (nl) |
| PT (1) | PT73933B (nl) |
| SE (1) | SE440505B (nl) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0123736A1 (en) * | 1983-04-29 | 1984-11-07 | Gist-Brocades N.V. | New process for the preparation of 21-hydroxy-20-keto-delta 16-steroids and new intermediate compounds formed in this process |
| US4585590A (en) * | 1984-02-03 | 1986-04-29 | The Upjohn Company | Cyanohydrin process |
| FR2559156B1 (fr) * | 1984-02-03 | 1989-03-24 | Roussel Uclaf | Procede de preparation de derives de la prednisone et produits intermediaires de ce procede |
| DE3585547D1 (de) * | 1984-02-03 | 1992-04-16 | Upjohn Co | Steroide mit einer enamid- oder enimidgruppe sowie ihre herstellung. |
| US4831131A (en) * | 1984-02-03 | 1989-05-16 | The Upjohn Company | 11β,17α-Dihydroxy-17β-cyano-androstanes |
| US4548748A (en) * | 1984-02-03 | 1985-10-22 | The Upjohn Company | Cyanohydrin process |
| FR2620708B1 (fr) * | 1984-02-03 | 1994-11-04 | Roussel Uclaf | Nouveaux produits industriels, leur procede de preparation et leur application |
| FR2571727B1 (fr) * | 1984-10-16 | 1987-06-12 | Roussel Uclaf | Nouveaux produits steroides comportant, en position 23, un radical dihydro oxazolyle, leur procede de preparation, leur application a la preparation de produits de la serie des 20 cetopregnanes et intermediaires de cette application |
| HU208437B (en) * | 1988-04-08 | 1993-10-28 | Roussel Uclaf | Process for producing 9-alpha-hydroxy- -17-methylene-steroides for synthetizing corticosteroides |
| MY105302A (en) * | 1989-11-27 | 1994-09-30 | Schering Corp | Process for dehydrating corticosteroid intermediates. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338892A (en) * | 1964-11-24 | 1967-08-29 | Lilly Co Eli | Steroidal carbamic acid-gamma-lactones |
| JPS512460B1 (nl) * | 1967-10-05 | 1976-01-26 | ||
| CH549001A (de) * | 1970-04-17 | 1974-05-15 | Ciba Geigy Ag | Verfahren zur herstellung neuer halogensteroide. |
| US4232013A (en) * | 1977-12-03 | 1980-11-04 | Lark S.P.A. | 16,17-Pyrazolino- and 16,17-isopyrazolino-1,4-pregnadiene derivatives |
| HU178397B (en) * | 1978-04-01 | 1982-04-28 | Gyogyszerkutato Intezet | Process for preparing substituted derivatives of steroid-spiro-oxazolidione derivatives |
-
1980
- 1980-11-05 FR FR8023575A patent/FR2493324B1/fr not_active Expired
-
1981
- 1981-09-25 SE SE8105686A patent/SE440505B/sv not_active IP Right Cessation
- 1981-10-27 IT IT49576/81A patent/IT1171613B/it active
- 1981-11-03 FI FI813459A patent/FI72526C/fi not_active IP Right Cessation
- 1981-11-03 US US06/317,584 patent/US4401596A/en not_active Expired - Fee Related
- 1981-11-04 DK DK487081A patent/DK162771C/da not_active IP Right Cessation
- 1981-11-04 GB GB8133233A patent/GB2086907B/en not_active Expired
- 1981-11-04 NL NL8104985A patent/NL8104985A/nl not_active Application Discontinuation
- 1981-11-04 PT PT73933A patent/PT73933B/pt not_active IP Right Cessation
- 1981-11-05 AT AT0475081A patent/AT386602B/de not_active IP Right Cessation
- 1981-11-05 CH CH7092/81A patent/CH652726A5/fr not_active IP Right Cessation
- 1981-11-05 HU HU813304A patent/HU183666B/hu not_active IP Right Cessation
- 1981-11-05 JP JP56176594A patent/JPS57106700A/ja active Granted
- 1981-11-05 DE DE19813144009 patent/DE3144009A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CH652726A5 (fr) | 1985-11-29 |
| IT8149576A0 (it) | 1981-10-27 |
| DK162771C (da) | 1992-04-27 |
| FR2493324B1 (nl) | 1983-01-21 |
| US4401596A (en) | 1983-08-30 |
| GB2086907A (en) | 1982-05-19 |
| ATA475081A (de) | 1988-02-15 |
| NL8104985A (nl) | 1982-06-01 |
| JPS57106700A (en) | 1982-07-02 |
| DK162771B (da) | 1991-12-09 |
| FI72526C (fi) | 1987-06-08 |
| AT386602B (de) | 1988-09-26 |
| PT73933B (fr) | 1983-11-30 |
| DE3144009A1 (de) | 1982-06-16 |
| GB2086907B (en) | 1984-12-12 |
| PT73933A (fr) | 1981-12-01 |
| DK487081A (da) | 1982-05-06 |
| HU183666B (en) | 1984-05-28 |
| JPH026359B2 (nl) | 1990-02-08 |
| SE8105686L (sv) | 1982-05-06 |
| FI72526B (fi) | 1987-02-27 |
| FI813459L (fi) | 1982-05-06 |
| FR2493324A1 (nl) | 1982-05-07 |
| IT1171613B (it) | 1987-06-10 |
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