HU187843B - Process for producing 17-alpha-hydroxy-17-beta-bracket-hydroxy-acetyl-bracket closed-steroides - Google Patents
Process for producing 17-alpha-hydroxy-17-beta-bracket-hydroxy-acetyl-bracket closed-steroides Download PDFInfo
- Publication number
- HU187843B HU187843B HU82259A HU25982A HU187843B HU 187843 B HU187843 B HU 187843B HU 82259 A HU82259 A HU 82259A HU 25982 A HU25982 A HU 25982A HU 187843 B HU187843 B HU 187843B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- hydroxy
- compounds
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- LTAAMLCDIRMBNP-UHFFFAOYSA-N acetic acid;iodosylbenzene Chemical compound CC(O)=O.CC(O)=O.O=IC1=CC=CC=C1 LTAAMLCDIRMBNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000000468 ketone group Chemical group 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 229930194542 Keto Natural products 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Chemical group 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
- -1 ethyl (20Z) -3,3-ethylenedioxy-20-phenylaminopregna-5,17 (20)-diene-21-ol Chemical compound 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical group C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 2
- 229940074439 potassium sodium tartrate Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- QBCWWPVNAGTVHO-CNLMXNECSA-N C1OC2(CC3=CC[C@H]4[C@@H]5CC/C(=C(\COC(C)=O)/NC=O)/[C@]5(CC[C@@H]4[C@]3(CC2)C)C)OC1 Chemical compound C1OC2(CC3=CC[C@H]4[C@@H]5CC/C(=C(\COC(C)=O)/NC=O)/[C@]5(CC[C@@H]4[C@]3(CC2)C)C)OC1 QBCWWPVNAGTVHO-CNLMXNECSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000011210 chromatographic step Methods 0.000 description 1
- 150000001887 cortisones Chemical class 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- BLEBFDYUDVZRFG-UHFFFAOYSA-N dichloromethane;propan-2-ol Chemical compound ClCCl.CC(C)O BLEBFDYUDVZRFG-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- UIICPZFWHBJNIG-UHFFFAOYSA-N sodium;2-methoxyethanolate Chemical compound [Na+].COCC[O-] UIICPZFWHBJNIG-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8101688A FR2498607A1 (fr) | 1981-01-29 | 1981-01-29 | Nouveau procede de preparation de 17a-hydroxy 17b-hydroxyacetyle steroides, produits intermediaires correspondants et produits finals obtenus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187843B true HU187843B (en) | 1986-02-28 |
Family
ID=9254633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82259A HU187843B (en) | 1981-01-29 | 1982-01-28 | Process for producing 17-alpha-hydroxy-17-beta-bracket-hydroxy-acetyl-bracket closed-steroides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4565656A (en, 2012) |
| EP (1) | EP0058097B1 (en, 2012) |
| JP (1) | JPS57144299A (en, 2012) |
| AT (1) | ATE8638T1 (en, 2012) |
| DE (1) | DE3260408D1 (en, 2012) |
| DK (1) | DK37782A (en, 2012) |
| FI (1) | FI77462C (en, 2012) |
| FR (1) | FR2498607A1 (en, 2012) |
| HU (1) | HU187843B (en, 2012) |
| PT (1) | PT74343B (en, 2012) |
Families Citing this family (5)
| 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 |
| US4910191A (en) * | 1988-06-28 | 1990-03-20 | Merrell Dow Pharmaceuticals Inc. | 19-substituted progesterone derivatives useful as 19-hydroxylase inhibitors |
| US5202316A (en) * | 1989-03-22 | 1993-04-13 | Roussel Uclaf | N,N,N',N'-6-(1-piperazinyl)-2,5-pyridinediamines |
| FR2683530B1 (fr) * | 1991-11-08 | 1994-01-21 | Roussel Uclaf | Nouveau procede de preparation de derives 20-oxo 17 alpha, 21-dihydroxyles du pregnane et nouveaux intermediaires. |
| FR2719588B1 (fr) * | 1994-05-03 | 1996-06-07 | Roussel Uclaf | Nouveau procédé de préparation de la substance "S" et nouveaux intermédiaires. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793350A (en) * | 1971-10-01 | 1974-02-19 | Syntex Corp | Process for preparing 17alpha,21-dihydroxy-20-keto-pregnanes,derivatives and intermediates thereof |
| DE2603266A1 (de) * | 1976-01-29 | 1977-08-11 | Hoechst Ag | 17-hydroxyacetylsteroide und verfahren zu ihrer herstellung |
| DE2655104A1 (de) * | 1976-12-04 | 1978-06-08 | Hoechst Ag | Verfahren zur herstellung von 17alpha-hydroxy-21-acetoxy-progesteron |
| DE2704130A1 (de) * | 1977-01-28 | 1978-08-10 | Schering Ag | Verfahren zur herstellung von 17 beta- hydroxy-20-alkoxy-pregnan-21-saeure-derivaten |
| FR2462445A1 (fr) * | 1979-07-31 | 1981-02-13 | Roussel Uclaf | Nouveaux derives 17-/(hydroxymethyl) (formamido) methylene/steroides, leur procede de preparation et leur application a l'introduction de la chaine laterale hydroxyacetyle |
-
1981
- 1981-01-29 FR FR8101688A patent/FR2498607A1/fr active Granted
-
1982
- 1982-01-08 DE DE8282400026T patent/DE3260408D1/de not_active Expired
- 1982-01-08 EP EP82400026A patent/EP0058097B1/fr not_active Expired
- 1982-01-08 AT AT82400026T patent/ATE8638T1/de not_active IP Right Cessation
- 1982-01-26 FI FI820240A patent/FI77462C/fi not_active IP Right Cessation
- 1982-01-27 PT PT74343A patent/PT74343B/pt not_active IP Right Cessation
- 1982-01-27 US US06/343,357 patent/US4565656A/en not_active Expired - Fee Related
- 1982-01-28 HU HU82259A patent/HU187843B/hu not_active IP Right Cessation
- 1982-01-28 DK DK37782A patent/DK37782A/da not_active Application Discontinuation
- 1982-01-29 JP JP57011927A patent/JPS57144299A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK37782A (da) | 1982-07-30 |
| FR2498607A1 (fr) | 1982-07-30 |
| PT74343A (fr) | 1982-02-01 |
| EP0058097A2 (fr) | 1982-08-18 |
| US4565656A (en) | 1986-01-21 |
| FI820240L (fi) | 1982-07-30 |
| DE3260408D1 (en) | 1984-08-30 |
| FI77462C (fi) | 1989-03-10 |
| EP0058097B1 (fr) | 1984-07-25 |
| ATE8638T1 (de) | 1984-08-15 |
| EP0058097A3 (en) | 1982-10-27 |
| JPS57144299A (en) | 1982-09-06 |
| JPH036158B2 (en, 2012) | 1991-01-29 |
| PT74343B (fr) | 1984-05-30 |
| FI77462B (fi) | 1988-11-30 |
| FR2498607B1 (en, 2012) | 1983-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5854160B2 (ja) | １α，３β−ジヒドロキシステロイド−５−エンまたはその誘導体の製造方法 | |
| US4425273A (en) | Process for production of chenodeoxycholic acid | |
| CA1185233A (en) | Process for preparing high purity ursodeoxycholic acid | |
| JPS591278B2 (ja) | ７−デヒドロコレステロ−ル誘導体及びその製造方法 | |
| EP0056000B1 (fr) | Dérivés 17/(alkoxycarbonyle) (formamido) méthylène/stéroides et leur préparation | |
| HU187843B (en) | Process for producing 17-alpha-hydroxy-17-beta-bracket-hydroxy-acetyl-bracket closed-steroides | |
| US2697109A (en) | 16-nitromethylpregnen-20-ones and process | |
| JPH0276896A (ja) | ステロイド化合物およびその製造方法 | |
| JP3037508B2 (ja) | プレグナ−１，４−ジエン−３，２０−ジオンの新規な置換された１６−メチルステロイド誘導体、それらの製造法、それらの１６−メチレンステロイドの製造への用途及び新規な中間体 | |
| RU2009146C1 (ru) | Способ получения производных 19-норпрогестерона | |
| CA1231939A (fr) | PROCEDE DE PREPARATION DE DERIVES DE LA SERIE DE LA 17.alpha.-HYDROXY 19-NOR-PROGESTERONE | |
| JP2509467B2 (ja) | ３−アルコキシ−１８−メチル−３，５−エストラジエン−１７−オン | |
| JPH0320399B2 (en, 2012) | ||
| JPS6244560B2 (en, 2012) | ||
| US4102907A (en) | Desulfinylation process for preparing androsta-4,9(11)-diene-3,17-dione | |
| US4145346A (en) | Preparation of 3β-hydroxy-27-norcholest-5-ene-25-one and intermediates thereof | |
| JPH0122278B2 (en, 2012) | ||
| SU679147A3 (ru) | Способ получени правовращающих гомостероидов | |
| WO1993021204A1 (en) | Method for preparing cholesta-5,7-diene-3-beta,25-diol and analogs thereof | |
| JP2714392B2 (ja) | ステロイド誘導体の製造法 | |
| CA1199907A (fr) | PROCEDE POUR LA PREPARATION DE DERIVES DE STEROIDES HYDROXYLES EN 5.alpha., ET LES DERIVES AINSI OBTENUS | |
| JP3129758B2 (ja) | 活性型ビタミンｄ３誘導体の製造法 | |
| JPS6148501B2 (en, 2012) | ||
| JPH0153680B2 (en, 2012) | ||
| WO1993002095A1 (fr) | Nouveaux steroides substitues en position 6 leurs procedes d'obtention et des compositions pharmaceutiques en renfermant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |