FR2463777A1 - Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments - Google Patents
Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments Download PDFInfo
- Publication number
- FR2463777A1 FR2463777A1 FR7920840A FR7920840A FR2463777A1 FR 2463777 A1 FR2463777 A1 FR 2463777A1 FR 7920840 A FR7920840 A FR 7920840A FR 7920840 A FR7920840 A FR 7920840A FR 2463777 A1 FR2463777 A1 FR 2463777A1
- Authority
- FR
- France
- Prior art keywords
- pregnan
- amino
- formula
- carbodiimide
- radical
- 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.)
- Granted
Links
- 239000003814 drug Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 AMINOACETYL Chemical class 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 150000001718 carbodiimides Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 229940126601 medicinal product Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 206010003246 arthritis Diseases 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 5
- 229960001614 levamisole Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000004054 inflammatory process Effects 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
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 class 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000000706 filtrate Substances 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 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
- YPEARZUTWVZHIZ-SRJHXTLLSA-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]ethanol Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(O)C)[C@@]1(C)CC2 YPEARZUTWVZHIZ-SRJHXTLLSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 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
- 230000001363 autoimmune Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 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
- 210000001364 upper extremity Anatomy 0.000 description 2
- VIQFMADXQMGZER-CJBOSLRMSA-N (1S)-1-[(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 NC1C[C@@H]2CC[C@H]3[C@@H]4CC[C@H]([C@H](C)O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C VIQFMADXQMGZER-CJBOSLRMSA-N 0.000 description 1
- 102220543423 26S proteasome non-ATPase regulatory subunit 10_L20S_mutation Human genes 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 238000012935 Averaging Methods 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
- 208000009386 Experimental Arthritis Diseases 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
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 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
- 208000007502 anemia Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000011394 anticancer treatment Methods 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007123 defense 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
- 229960003699 evans blue Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 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
- JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 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
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing 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)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| SE8005309A SE446006B (sv) | 1979-08-17 | 1980-07-22 | (20s) 3alfa-/(aminoacetyl)-amino/-5alfa-preganan-20-ol och additionssalter derav samt farmaceutiska kompositioner innehallande dessa |
| ZA00804473A ZA804473B (en) | 1979-08-17 | 1980-07-24 | Derivatives of 5a-pregnan-20-01 and its salts with acids, their preparation, their use as medicaments and the compositions containing them |
| FI802462A FI68844C (fi) | 1979-08-17 | 1980-08-06 | Foerfarande foer framstaellning av (20s) 3alfa-((aminoacetyl)amino)-5alfa-pregnan-20-ol och dess salter |
| GB8026312A GB2057448B (en) | 1979-08-17 | 1980-08-13 | (20s)-3-(aminoacetylamino)-5-pregnan-20-ol and its acid addition salts |
| BE0/201765A BE884794A (fr) | 1979-08-17 | 1980-08-14 | Nouveau derive du 5 alpha-pregnan-20-ol et ses sels avec les acides, leur preparation, leur application comme medicaments et les compositions les renfermant |
| ES494256A ES494256A0 (es) | 1979-08-17 | 1980-08-14 | Procedimiento de preparacion de (20 s) - 3 - - ((aminoace- til)amino)-5 - - pregnan- 20 - ol |
| PT71700A PT71700B (fr) | 1979-08-17 | 1980-08-14 | Procede de preparation d'un nouveau derive du (20s)3alpha-<(amino acetyl)amino>5alpha-pregnan-20-ol et de ses sels |
| IT49507/80A IT1145382B (it) | 1979-08-17 | 1980-08-14 | Derivato di salfa-pregnan-20-olo e relativi sali di addizione acida procedimento per la loro preparazione loro applicazione come farmaci e composizione che li includono |
| NL8004600A NL8004600A (nl) | 1979-08-17 | 1980-08-14 | Nieuw derivaat van 5alfa-pregnanol-20 en zijn zouten met zuren, bereiding en toepassing als geneesmiddelen van deze stoffen en preparaten, die ze bevatten. |
| CH616280A CH646182A5 (fr) | 1979-08-17 | 1980-08-15 | Derive du 5-pregnan-20-ol et ses sels avec les acides, leur preparation et medicaments les renfermant. |
| IE1737/80A IE50226B1 (en) | 1979-08-17 | 1980-08-15 | Derivative of 5alpha-pregnan-20-ol and its acid addition salts |
| HU80802040A HU180376B (en) | 1979-08-17 | 1980-08-15 | Process for preparing /20s/-3alpha-//aminoacetyl/-amino/-5alpha-pregnan-20-ol and salts thereof |
| AU61486/80A AU529528B2 (en) | 1979-08-17 | 1980-08-15 | 5 alpha-pre gnan-20-ols |
| JP11189680A JPS5659800A (en) | 1979-08-17 | 1980-08-15 | Novel derivative of 5 alphaapregnanee200oll200ol and salt of said acid* these manufacture* use as drug and composition containing them |
| DK352380A DK352380A (da) | 1979-08-17 | 1980-08-15 | Fremgangsmaade til fremstilling af (20s)-3alfa-( (aminoacetyl)-amino)-5alfa-pregnan-20-ol eller additionssalte deraf |
| CA000358412A 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 |
| AT0420880A AT373902B (de) | 1979-08-17 | 1980-08-18 | Verfahren zur herstellung des neuen (20s)-3 alpha-((aminoacetyl)amino)-5 alpha-pregnan-20-ols und seiner salze |
| DE19803031161 DE3031161A1 (de) | 1979-08-17 | 1980-08-18 | Neues 5 (alpha)-pregnan-20-ol-derivat und dessen salze mit saeuren, deren herstellung, deren verwendung als arzneimittel und die diese enthaltenden zusammensetzungen |
| US06/292,791 US4424218A (en) | 1979-08-17 | 1981-08-14 | Novel 3 α-amino steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2463777A1 true FR2463777A1 (fr) | 1981-02-27 |
| FR2463777B1 FR2463777B1 (enrdf_load_stackoverflow) | 1983-04-29 |
Family
ID=9228902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7920840A Granted FR2463777A1 (fr) | 1979-08-17 | 1979-08-17 | Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments |
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 |
Citations (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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3196169A (en) * | 1964-11-03 | 1965-07-20 | American Home Prod | Aminoacyl aminosteroids |
Non-Patent Citations (2)
| Title |
|---|
| EXBK/65 * |
| EXBK/67 * |
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 |
| 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 |
| CA1140111A (fr) | 1983-01-25 |
| IE801737L (en) | 1981-02-17 |
| JPS5659800A (en) | 1981-05-23 |
| DE3031161A1 (de) | 1981-03-26 |
| FI68844C (fi) | 1985-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0233106B1 (fr) | (-)-Benzhydrylsulfinylacétamide, procédé de préparation et utilisation en thérapeutique | |
| CA1193247A (fr) | Procede de preparation de nouveaux derives du 3-amino- pregn-5ene et de leurs sels | |
| CA2024728A1 (fr) | Utilisation de composes anti-progestomimetiques | |
| FR2463777A1 (fr) | Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments | |
| FR2567514A1 (fr) | Nouveaux ether-oxydes derives de cyclopropylphenols | |
| FR2494697A1 (fr) | Nouveaux derives steroides 3-amines, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant | |
| EP0001021A2 (fr) | Nouveaux dérivés d'alcaloides pentacycliques, procédé de préparation, application à la synthèse de produits du groupe de l'éburnamonine et compositions pharmaceutiques | |
| CH642378A5 (fr) | Nouveau derive du paracetamol, son procede de preparation et son utilisation en therapeutique. | |
| WO2018078010A1 (fr) | Derives d'acides quiniques polysubstitues et leur utilisation pour le traitement des maladies neurodégéneratives | |
| FR2499981A1 (fr) | Acides amino-2 halogenobenzoyl-3 methylphenylacetiques et leurs esters et sels utiles comme medicaments anti-inflammatoires et analgesiques | |
| EP0176444B1 (fr) | Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant | |
| CA1060020A (fr) | Procede de preparation de nouveaux derives de la dibenzo/b,c/ thiepine et leurs sels | |
| CH646146A5 (fr) | Derive du 1alpha,25-dihydroxy cholecalciferol et son procede de preparation. | |
| EP0027768B1 (fr) | Nouvelles résines échangeuses d'ions du type acide, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| CA1024515A (en) | 2-methyl-3-(0-cyanophenyl)-4 (3h)-quinazolone | |
| CA1080233A (fr) | Procede de preparation de nouveaux derives de l'oxadiazole et de leurs sels | |
| US3626059A (en) | Trihydroxyphenylalanine for treatment of hypertension | |
| EP0022737B1 (fr) | Imines dérivées de l'amino-5 benzodioxole-1,3 utiles comme médicaments et leur préparation | |
| FR2459249A1 (fr) | Derives de steroides azotes sur l'atome de carbone en positio n 21 de la chaine laterale et leur application comme anti-inflammatoires | |
| CA1175415A (fr) | Procede de preparation de nouveaux derives steroides 3-amino substitue | |
| FR2707879A1 (fr) | Composition à base d'acides gras douée de propriétés anti-inflammatoires. | |
| BE828694R (fr) | Thieno-benzopyrannes et thiopyrano-benzopyrannes, produits intermediaires et procede pour leur obtention | |
| FR2611712A1 (fr) | Nouveaux derives n-substitues de l'alpha-mercaptomethyl benzene propanamide, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant | |
| EP1157028B1 (fr) | Nouveaux derives de steroides 11.beta.-substitues , leurs procedes de preparation et intermediaires de ce procede, leur application a titre de medicaments et compositions les contenant | |
| BE873380A (fr) | Nouveaux derives de prostaglandine, leur procede de preparation et leur application en therapeutique |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |