CH616437A5 - Process for the preparation of 3,20-diketopregnenes having an 11beta-acetal group and their derivatives - Google Patents
Process for the preparation of 3,20-diketopregnenes having an 11beta-acetal group and their derivatives Download PDFInfo
- Publication number
- CH616437A5 CH616437A5 CH1133976A CH1133976A CH616437A5 CH 616437 A5 CH616437 A5 CH 616437A5 CH 1133976 A CH1133976 A CH 1133976A CH 1133976 A CH1133976 A CH 1133976A CH 616437 A5 CH616437 A5 CH 616437A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- alkyl
- hydrogen atom
- formula
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 8
- WJYGBTBQRPGPTC-GLRFCKCYSA-N (8r,9s,10s,13s,14s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-one Chemical class C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 WJYGBTBQRPGPTC-GLRFCKCYSA-N 0.000 title description 2
- 150000003431 steroids Chemical class 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims abstract 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract 3
- 125000004036 acetal group Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- QQCBOIWDENXRLP-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthrene Chemical class C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 claims 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960002383 halcinonide Drugs 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000003130 pregnenes Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 abstract description 3
- 229940037128 systemic glucocorticoids Drugs 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- -1 1-hydroxy-3,20-diketopregnene Chemical compound 0.000 description 4
- CVZKXVDVMQVRQE-UHFFFAOYSA-N 7-ethoxybicyclo[4.2.0]octa-1,3,5-triene Chemical compound C1=CC=C2C(OCC)CC2=C1 CVZKXVDVMQVRQE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 150000003047 pimelic acids Chemical class 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/610,955 US3976637A (en) | 1975-09-08 | 1975-09-08 | 3,20-Diketopregnenes having an 11β-acetal group |
| US66817776A | 1976-03-18 | 1976-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616437A5 true CH616437A5 (en) | 1980-03-31 |
Family
ID=27086400
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1133976A CH616437A5 (en) | 1975-09-08 | 1976-09-07 | Process for the preparation of 3,20-diketopregnenes having an 11beta-acetal group and their derivatives |
| CH626779A CH618186A5 (en) | 1975-09-08 | 1979-07-04 | Process for the preparation of 3,20-diketopregnenes having a 11beta-acetal group. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH626779A CH618186A5 (en) | 1975-09-08 | 1979-07-04 | Process for the preparation of 3,20-diketopregnenes having a 11beta-acetal group. |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5233664A (enExample) |
| AU (1) | AU506546B2 (enExample) |
| BE (1) | BE845943A (enExample) |
| CA (1) | CA1058161A (enExample) |
| CH (2) | CH616437A5 (enExample) |
| DE (1) | DE2640490A1 (enExample) |
| DK (1) | DK402676A (enExample) |
| FR (1) | FR2322607A1 (enExample) |
| GB (1) | GB1544512A (enExample) |
| IE (1) | IE44534B1 (enExample) |
| NL (1) | NL7609912A (enExample) |
| NO (2) | NO144491C (enExample) |
| SE (1) | SE7609884L (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976637A (en) * | 1975-09-08 | 1976-08-24 | E. R. Squibb & Sons, Inc. | 3,20-Diketopregnenes having an 11β-acetal group |
-
1976
- 1976-08-31 IE IE1942/76A patent/IE44534B1/en unknown
- 1976-08-31 CA CA260,229A patent/CA1058161A/en not_active Expired
- 1976-09-02 AU AU17384/76A patent/AU506546B2/en not_active Expired
- 1976-09-06 GB GB36853/76A patent/GB1544512A/en not_active Expired
- 1976-09-07 SE SE7609884A patent/SE7609884L/xx unknown
- 1976-09-07 NL NL7609912A patent/NL7609912A/xx not_active Application Discontinuation
- 1976-09-07 CH CH1133976A patent/CH616437A5/fr not_active IP Right Cessation
- 1976-09-07 NO NO76763060A patent/NO144491C/no unknown
- 1976-09-07 DK DK402676A patent/DK402676A/da unknown
- 1976-09-08 DE DE19762640490 patent/DE2640490A1/de not_active Withdrawn
- 1976-09-08 FR FR7627002A patent/FR2322607A1/fr active Granted
- 1976-09-08 JP JP51108717A patent/JPS5233664A/ja active Pending
- 1976-09-08 BE BE170429A patent/BE845943A/xx not_active IP Right Cessation
-
1979
- 1979-07-04 CH CH626779A patent/CH618186A5/fr not_active IP Right Cessation
-
1981
- 1981-01-27 NO NO81810271A patent/NO145919C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1544512A (en) | 1979-04-19 |
| NL7609912A (nl) | 1977-03-10 |
| BE845943A (fr) | 1977-03-08 |
| AU1738476A (en) | 1978-03-09 |
| DE2640490A1 (de) | 1977-03-10 |
| NO144491C (no) | 1981-09-09 |
| CH618186A5 (en) | 1980-07-15 |
| NO144491B (no) | 1981-06-01 |
| FR2322607B1 (enExample) | 1979-02-23 |
| NO145919C (no) | 1982-06-30 |
| NO810271L (no) | 1977-03-09 |
| AU506546B2 (en) | 1980-01-10 |
| JPS5233664A (en) | 1977-03-14 |
| IE44534L (en) | 1977-03-08 |
| IE44534B1 (en) | 1981-12-30 |
| FR2322607A1 (fr) | 1977-04-01 |
| CA1058161A (en) | 1979-07-10 |
| DK402676A (da) | 1977-03-09 |
| NO145919B (no) | 1982-03-15 |
| NO763060L (enExample) | 1977-03-09 |
| SE7609884L (sv) | 1977-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |