HU184896B - Process for producing new 3-alpha-amino-substituted-steroide derivatives - Google Patents
Process for producing new 3-alpha-amino-substituted-steroide derivatives Download PDFInfo
- Publication number
- HU184896B HU184896B HU813135A HU313581A HU184896B HU 184896 B HU184896 B HU 184896B HU 813135 A HU813135 A HU 813135A HU 313581 A HU313581 A HU 313581A HU 184896 B HU184896 B HU 184896B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- group
- amino
- hydroxy
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- -1 nicotinoyl Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 125000006239 protecting group Chemical group 0.000 claims description 19
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
- 239000011707 mineral Substances 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000004471 Glycine Substances 0.000 claims description 7
- 108010008488 Glycylglycine Proteins 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- 229940043257 glycylglycine Drugs 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 6
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 6
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229940080818 propionamide Drugs 0.000 claims description 4
- WEZIVKOJCVXWTM-PMUPNNHLSA-N 2-amino-N-[(3R,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N-methylacetamide Chemical compound NCC(=O)N(C)[C@H]1C[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 WEZIVKOJCVXWTM-PMUPNNHLSA-N 0.000 claims description 3
- 150000002332 glycine derivatives Chemical class 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 239000003755 preservative agent Substances 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
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- 230000004936 stimulating effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 235000019871 vegetable fat 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- 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
-
- 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
-
- 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
- C07J41/0027—Azides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024750A FR2494698A1 (fr) | 1980-11-21 | 1980-11-21 | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184896B true HU184896B (en) | 1984-10-29 |
Family
ID=9248226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU813135A HU184896B (en) | 1980-11-21 | 1981-10-26 | Process for producing new 3-alpha-amino-substituted-steroide derivatives |
Country Status (23)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9084800B2 (en) * | 2011-11-07 | 2015-07-21 | Natreon, Inc. | Indolealkylamino-withasteroid conjugates and method of use |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2430467A (en) * | 1944-02-11 | 1947-11-11 | Glidden Co | 3-amino-derivatives of steroids and method of making same |
| US2781342A (en) * | 1952-05-17 | 1957-02-12 | Upjohn Co | Steroid enamines |
| FR1311761A (fr) * | 1959-09-12 | 1962-12-14 | Clin Byla Ets | Composés aminés de la série des stéroïdes et procédé de préparation de tels composés |
| GB962324A (en) * | 1959-09-12 | 1964-07-01 | Clin Byla Ets | Steroid compounds and production thereof |
| NL103735C (enrdf_load_stackoverflow) * | 1961-02-17 | |||
| US3503959A (en) * | 1962-03-30 | 1970-03-31 | Sterling Drug Inc | 3-amino steroids |
| US3196168A (en) * | 1964-02-18 | 1965-07-20 | American Home Prod | Aminoaroyl aminosteroids |
| BE647858A (enrdf_load_stackoverflow) * | 1964-05-13 | |||
| US3196169A (en) * | 1964-11-03 | 1965-07-20 | American Home Prod | Aminoacyl aminosteroids |
| BE672238A (enrdf_load_stackoverflow) * | 1965-11-12 | 1966-03-01 | ||
| BE811304R (fr) * | 1973-10-24 | 1974-06-17 | Pr0cede de preparation du (20 s) 3 beta -n-dimethylamino | |
| FR2463777A1 (fr) * | 1979-08-17 | 1981-02-27 | Roussel Uclaf | Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments |
-
1980
- 1980-11-21 FR FR8024750A patent/FR2494698A1/fr active Granted
-
1981
- 1981-10-09 SE SE8105995A patent/SE451456B/sv not_active IP Right Cessation
- 1981-10-26 HU HU813135A patent/HU184896B/hu unknown
- 1981-11-06 IL IL64224A patent/IL64224A0/xx not_active IP Right Cessation
- 1981-11-11 ZA ZA817806A patent/ZA817806B/xx unknown
- 1981-11-18 KR KR1019810004462A patent/KR880001239B1/ko not_active Expired
- 1981-11-18 AT AT0497081A patent/AT389703B/de not_active IP Right Cessation
- 1981-11-19 FI FI813677A patent/FI77871C/fi not_active IP Right Cessation
- 1981-11-20 CH CH7459/81A patent/CH651056A5/fr not_active IP Right Cessation
- 1981-11-20 DE DE19813146117 patent/DE3146117A1/de not_active Ceased
- 1981-11-20 SU SU813355225A patent/SU1327789A3/ru active
- 1981-11-20 AU AU77723/81A patent/AU546100B2/en not_active Ceased
- 1981-11-20 NL NL8105260A patent/NL8105260A/nl not_active Application Discontinuation
- 1981-11-20 BE BE0/206612A patent/BE891201A/fr not_active IP Right Cessation
- 1981-11-20 IT IT49746/81A patent/IT1172086B/it active
- 1981-11-20 JP JP56185540A patent/JPS57116099A/ja active Granted
- 1981-11-20 IE IE2732/81A patent/IE52188B1/en unknown
- 1981-11-20 ES ES507309A patent/ES507309A0/es active Granted
- 1981-11-20 PT PT74015A patent/PT74015B/pt unknown
- 1981-11-20 CA CA000390559A patent/CA1175415A/fr not_active Expired
- 1981-11-20 LU LU83781A patent/LU83781A1/fr unknown
- 1981-11-20 DK DK514981A patent/DK161093C/da not_active IP Right Cessation
- 1981-11-23 GB GB8135218A patent/GB2087894B/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |