SE416950B - Derivat i androstanserien till anvendning som mellanprodukt for framstellning av spirolaktoner som ett forfarande for framstellning av mellanprodukten - Google Patents
Derivat i androstanserien till anvendning som mellanprodukt for framstellning av spirolaktoner som ett forfarande for framstellning av mellanproduktenInfo
- Publication number
- SE416950B SE416950B SE7401495A SE7401495A SE416950B SE 416950 B SE416950 B SE 416950B SE 7401495 A SE7401495 A SE 7401495A SE 7401495 A SE7401495 A SE 7401495A SE 416950 B SE416950 B SE 416950B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- general formula
- hydrogen atom
- alkali metal
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 title description 2
- 229960002256 spironolactone Drugs 0.000 title description 2
- 239000013067 intermediate product Substances 0.000 title 2
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical class C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 66
- 229910052783 alkali metal Inorganic materials 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- -1 alkali metal carboxylate Chemical class 0.000 claims description 15
- 150000001340 alkali metals Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 9
- 125000000468 ketone group Chemical group 0.000 claims description 9
- 125000003003 spiro group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 5
- 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 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 150000001441 androstanes Chemical class 0.000 claims 1
- 125000004436 sodium atom Chemical group 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HZTZILUYYUBRRV-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HZTZILUYYUBRRV-VMXHOPILSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7304058A FR2216276B1 (ja) | 1973-02-06 | 1973-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7401495L SE7401495L (ja) | 1974-08-07 |
| SE416950B true SE416950B (sv) | 1981-02-16 |
Family
ID=9114389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7401495A SE416950B (sv) | 1973-02-06 | 1974-02-05 | Derivat i androstanserien till anvendning som mellanprodukt for framstellning av spirolaktoner som ett forfarande for framstellning av mellanprodukten |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3919198A (ja) |
| JP (2) | JPS5940840B2 (ja) |
| AT (1) | AT344924B (ja) |
| BE (1) | BE810644A (ja) |
| CA (1) | CA1025436A (ja) |
| CH (1) | CH594702A5 (ja) |
| DK (1) | DK136827B (ja) |
| ES (2) | ES422922A1 (ja) |
| FR (1) | FR2216276B1 (ja) |
| GB (2) | GB1451844A (ja) |
| IE (1) | IE40282B1 (ja) |
| LU (1) | LU69329A1 (ja) |
| NL (1) | NL179384C (ja) |
| SE (1) | SE416950B (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2344286A1 (fr) | 1976-03-16 | 1977-10-14 | Roussel Uclaf | Nouveaux derives 17-spirosultines, les g-hydroxy acides correspondants, leur procede de preparation et leur application comme medicament |
| US4155906A (en) * | 1977-12-02 | 1979-05-22 | G. D. Searle & Co. | Process for preparing steroidal 3-oxo-4,6-dienes such as 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acidγ-lactone |
| DE2950832C2 (de) * | 1979-12-18 | 1983-03-17 | Hoechst Ag, 6000 Frankfurt | Spritzfertige injizierbare wäßrige Lösungen der Alkalisalze von Canrenoinsäure und Furosemid |
| TWI283245B (en) * | 2002-03-22 | 2007-07-01 | Upjohn Co | Processes to prepare eplerenone |
| DE102005049393B4 (de) * | 2005-10-15 | 2019-08-08 | Kennametal Widia Produktions Gmbh & Co. Kg | Verfahren zur Herstellung eines beschichteten Substratkörpers, Substratkörper mit einer Beschichtung und Verwendung des beschichteten Substratkörpers |
| CN108033989A (zh) * | 2017-12-28 | 2018-05-15 | 广西万德药业有限公司 | 坎利酮的制备方法 |
| CN110028542A (zh) * | 2019-05-17 | 2019-07-19 | 山东宝利甾体生物科技有限公司 | 坎利酮的清洁生产方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1089788A (en) * | 1965-07-07 | 1967-11-08 | Parke Davis & Co | Process for the production of steroidal lactone compounds and intermediates thereof |
-
1973
- 1973-02-06 FR FR7304058A patent/FR2216276B1/fr not_active Expired
-
1974
- 1974-02-01 US US438602A patent/US3919198A/en not_active Expired - Lifetime
- 1974-02-05 BE BE140581A patent/BE810644A/xx unknown
- 1974-02-05 LU LU69329A patent/LU69329A1/xx unknown
- 1974-02-05 SE SE7401495A patent/SE416950B/sv not_active IP Right Cessation
- 1974-02-05 CH CH158574A patent/CH594702A5/xx not_active IP Right Cessation
- 1974-02-05 CA CA191,777A patent/CA1025436A/en not_active Expired
- 1974-02-05 ES ES422922A patent/ES422922A1/es not_active Expired
- 1974-02-06 GB GB545274A patent/GB1451844A/en not_active Expired
- 1974-02-06 GB GB113476A patent/GB1451845A/en not_active Expired
- 1974-02-06 JP JP49014628A patent/JPS5940840B2/ja not_active Expired
- 1974-02-06 NL NLAANVRAGE7401657,A patent/NL179384C/xx not_active IP Right Cessation
- 1974-02-06 AT AT92274A patent/AT344924B/de not_active IP Right Cessation
- 1974-02-06 IE IE227/74A patent/IE40282B1/en unknown
- 1974-02-06 DK DK62674AA patent/DK136827B/da not_active IP Right Cessation
-
1976
- 1976-01-16 ES ES444369A patent/ES444369A1/es not_active Expired
-
1982
- 1982-03-19 JP JP57042991A patent/JPS5850240B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2216276A1 (ja) | 1974-08-30 |
| JPS5850240B2 (ja) | 1983-11-09 |
| JPS49109366A (ja) | 1974-10-17 |
| SE7401495L (ja) | 1974-08-07 |
| LU69329A1 (ja) | 1974-09-25 |
| JPS5940840B2 (ja) | 1984-10-03 |
| AT344924B (de) | 1978-08-25 |
| BE810644A (fr) | 1974-08-05 |
| AU6521074A (en) | 1975-08-07 |
| ES444369A1 (es) | 1977-05-16 |
| GB1451844A (en) | 1976-10-06 |
| NL7401657A (ja) | 1974-08-08 |
| DK136827C (ja) | 1978-05-08 |
| ES422922A1 (es) | 1976-09-16 |
| IE40282L (en) | 1974-08-06 |
| ATA92274A (de) | 1977-12-15 |
| NL179384C (nl) | 1986-09-01 |
| CA1025436A (en) | 1978-01-31 |
| IE40282B1 (en) | 1979-04-25 |
| US3919198A (en) | 1975-11-11 |
| JPS57176999A (en) | 1982-10-30 |
| GB1451845A (en) | 1976-10-06 |
| FR2216276B1 (ja) | 1976-11-05 |
| CH594702A5 (ja) | 1978-01-31 |
| NL179384B (nl) | 1986-04-01 |
| DK136827B (da) | 1977-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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