CA1140111A - PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU (20S) 3.alpha.- /(AMINO-ACETYL)AMINO/ 5.alpha.-PREGNAN-20-OL ET DE SES SELS - Google Patents
PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU (20S) 3.alpha.- /(AMINO-ACETYL)AMINO/ 5.alpha.-PREGNAN-20-OL ET DE SES SELSInfo
- Publication number
- CA1140111A CA1140111A CA000358412A CA358412A CA1140111A CA 1140111 A CA1140111 A CA 1140111A CA 000358412 A CA000358412 A CA 000358412A CA 358412 A CA358412 A CA 358412A CA 1140111 A CA1140111 A CA 1140111A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- amino
- pregnan
- aminoacetyl
- addition salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- -1 AMINO-ACETYL Chemical class 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 13
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 230000009471 action Effects 0.000 claims abstract description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 9
- 239000011707 mineral Substances 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 150000001413 amino acids Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- VIQFMADXQMGZER-CGVINKDUSA-N (1s)-1-[(3r,5s,8r,9s,10s,13s,14s,17s)-3-amino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanol Chemical compound C([C@@H]1CC2)[C@H](N)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](O)C)[C@@]2(C)CC1 VIQFMADXQMGZER-CGVINKDUSA-N 0.000 claims abstract description 3
- VIQFMADXQMGZER-UHFFFAOYSA-N (20S) 3alpha-amino-5alpha-pregnane-20-ol Natural products C1CC2CC(N)CCC2(C)C2C1C1CCC(C(O)C)C1(C)CC2 VIQFMADXQMGZER-UHFFFAOYSA-N 0.000 claims abstract description 3
- WNTILTUNFXLYHC-UHFFFAOYSA-N (3alpha,5alpha,20R)-3-Aminopregnan-20-ol Natural products C1CC2C(O)C(O)CCC2(C)C2C1C1CCC(C(N)C)C1(C)CC2 WNTILTUNFXLYHC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 7
- 150000007524 organic acids Chemical class 0.000 claims abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 150000001718 carbodiimides Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- YPEARZUTWVZHIZ-JMTGGFPBSA-N 1-[(5R,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]ethanol Chemical compound CC(O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C YPEARZUTWVZHIZ-JMTGGFPBSA-N 0.000 abstract description 2
- 108060003951 Immunoglobulin Proteins 0.000 abstract description 2
- 230000007123 defense Effects 0.000 abstract description 2
- 102000018358 immunoglobulin Human genes 0.000 abstract description 2
- 229940072221 immunoglobulins Drugs 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 206010003246 arthritis Diseases 0.000 description 6
- 229960001614 levamisole Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000005069 ears Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 210000001364 upper extremity Anatomy 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- DYBPANJQVAJWGO-UHFFFAOYSA-N CCCl.CN(C)CCCN=C=N Chemical compound CCCl.CN(C)CCCN=C=N DYBPANJQVAJWGO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 229920000825 Fique Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 230000001363 autoimmune Effects 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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- CAGRHEDHVJKNBB-UHFFFAOYSA-N dihydroxyphosphanyl ethyl hydrogen phosphite Chemical compound CCOP(O)OP(O)O CAGRHEDHVJKNBB-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR79-20840 | 1979-08-17 | ||
| FR7920840A FR2463777A1 (fr) | 1979-08-17 | 1979-08-17 | Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140111A true CA1140111A (fr) | 1983-01-25 |
Family
ID=9228902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000358412A Expired CA1140111A (fr) | 1979-08-17 | 1980-08-15 | PROCEDE DE PREPARATION D'UN NOUVEAU DERIVE DU (20S) 3.alpha.- /(AMINO-ACETYL)AMINO/ 5.alpha.-PREGNAN-20-OL ET DE SES SELS |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2494698A1 (fr) * | 1980-11-21 | 1982-05-28 | Roussel Uclaf | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| FR2515188A1 (fr) * | 1981-10-27 | 1983-04-29 | Roussel Uclaf | Nouveaux derives du 3-amino-pregn-5-ene, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196169A (en) * | 1964-11-03 | 1965-07-20 | American Home Prod | Aminoacyl aminosteroids |
-
1979
- 1979-08-17 FR FR7920840A patent/FR2463777A1/fr active Granted
-
1980
- 1980-07-22 SE SE8005309A patent/SE446006B/sv not_active IP Right Cessation
- 1980-07-24 ZA ZA00804473A patent/ZA804473B/xx unknown
- 1980-08-06 FI FI802462A patent/FI68844C/fi not_active IP Right Cessation
- 1980-08-13 GB GB8026312A patent/GB2057448B/en not_active Expired
- 1980-08-14 IT IT49507/80A patent/IT1145382B/it active
- 1980-08-14 ES ES494256A patent/ES494256A0/es active Granted
- 1980-08-14 NL NL8004600A patent/NL8004600A/nl not_active Application Discontinuation
- 1980-08-14 BE BE0/201765A patent/BE884794A/fr not_active IP Right Cessation
- 1980-08-14 PT PT71700A patent/PT71700B/pt unknown
- 1980-08-15 DK DK352380A patent/DK352380A/da not_active Application Discontinuation
- 1980-08-15 JP JP11189680A patent/JPS5659800A/ja active Pending
- 1980-08-15 AU AU61486/80A patent/AU529528B2/en not_active Ceased
- 1980-08-15 CA CA000358412A patent/CA1140111A/fr not_active Expired
- 1980-08-15 CH CH616280A patent/CH646182A5/fr not_active IP Right Cessation
- 1980-08-15 IE IE1737/80A patent/IE50226B1/en unknown
- 1980-08-15 HU HU80802040A patent/HU180376B/hu not_active IP Right Cessation
- 1980-08-18 AT AT0420880A patent/AT373902B/de not_active IP Right Cessation
- 1980-08-18 DE DE19803031161 patent/DE3031161A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2057448A (en) | 1981-04-01 |
| IT8049507A0 (it) | 1980-08-14 |
| AU6148680A (en) | 1981-02-19 |
| IE50226B1 (en) | 1986-03-05 |
| FI802462A7 (fi) | 1981-02-18 |
| ES8103760A1 (es) | 1981-03-16 |
| ATA420880A (de) | 1983-07-15 |
| HU180376B (en) | 1983-02-28 |
| FI68844B (fi) | 1985-07-31 |
| DK352380A (da) | 1981-02-18 |
| FR2463777B1 (enrdf_load_stackoverflow) | 1983-04-29 |
| AT373902B (de) | 1984-03-12 |
| CH646182A5 (fr) | 1984-11-15 |
| PT71700A (fr) | 1980-09-01 |
| DE3031161C2 (enrdf_load_stackoverflow) | 1988-09-29 |
| GB2057448B (en) | 1983-05-18 |
| PT71700B (fr) | 1982-01-22 |
| BE884794A (fr) | 1981-02-16 |
| ES494256A0 (es) | 1981-03-16 |
| SE446006B (sv) | 1986-08-04 |
| FR2463777A1 (fr) | 1981-02-27 |
| ZA804473B (en) | 1981-07-29 |
| AU529528B2 (en) | 1983-06-09 |
| NL8004600A (nl) | 1981-02-19 |
| SE8005309L (sv) | 1981-02-18 |
| IT1145382B (it) | 1986-11-05 |
| IE801737L (en) | 1981-02-17 |
| JPS5659800A (en) | 1981-05-23 |
| DE3031161A1 (de) | 1981-03-26 |
| FI68844C (fi) | 1985-11-11 |
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