CA1026318A - Preparation process for spirolactone steroids - Google Patents
Preparation process for spirolactone steroidsInfo
- Publication number
- CA1026318A CA1026318A CA191,844A CA191844A CA1026318A CA 1026318 A CA1026318 A CA 1026318A CA 191844 A CA191844 A CA 191844A CA 1026318 A CA1026318 A CA 1026318A
- Authority
- CA
- Canada
- Prior art keywords
- produit
- représente
- que
- formule
- par
- 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
- 229960002256 spironolactone Drugs 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title 1
- -1 spirolactone steroids Chemical class 0.000 title 1
- 230000009471 action Effects 0.000 claims description 11
- 230000020477 pH reduction Effects 0.000 claims description 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006473 carboxylation reaction Methods 0.000 claims 1
- 150000002148 esters Chemical group 0.000 abstract description 4
- 150000002596 lactones Chemical class 0.000 abstract description 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 16
- 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 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- 125000003003 spiro group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 230000004927 fusion Effects 0.000 description 11
- 240000008042 Zea mays Species 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005035 acylthio group Chemical group 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- QCELPNCKVMQZMD-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-2,8,9,10,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 QCELPNCKVMQZMD-PNKHAZJDSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- 240000000489 Agave utahensis Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- NUPLBTPPIOMJPG-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-1,2,7,8,9,10,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 NUPLBTPPIOMJPG-PNKHAZJDSA-N 0.000 description 1
- PAOWPNQOTVTCAF-OEUJLIAZSA-N (8r,9s,10r,13s,14s)-3-ethoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@](CCC(OCC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C PAOWPNQOTVTCAF-OEUJLIAZSA-N 0.000 description 1
- MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 description 1
- IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 description 1
- IWEIPZWVWLBKPK-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IWEIPZWVWLBKPK-VMXHOPILSA-N 0.000 description 1
- HFJJFVWDQNSUGH-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2C=CCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HFJJFVWDQNSUGH-VMXHOPILSA-N 0.000 description 1
- ZBEMZLYGYDVQRP-SXYSDOLCSA-N (8s,9s,10r,13s,14s)-3-ethoxy-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C[C@@H]2[C@](CCC(OCC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC[C@]21C ZBEMZLYGYDVQRP-SXYSDOLCSA-N 0.000 description 1
- JMAPHBFIBIHSIT-ZBKBXNIDSA-N (8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JMAPHBFIBIHSIT-ZBKBXNIDSA-N 0.000 description 1
- 102100022749 Aminopeptidase N Human genes 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CYICTGKQQJTRIJ-DGGDGUMWSA-N C(C)(=O)S[C@H]1[C@H]2[C@@H]3CCC[C@@]3(C)CC[C@@H]2[C@]2(CCCC=C2C1)C Chemical compound C(C)(=O)S[C@H]1[C@H]2[C@@H]3CCC[C@@]3(C)CC[C@@H]2[C@]2(CCCC=C2C1)C CYICTGKQQJTRIJ-DGGDGUMWSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 241000027294 Fusi Species 0.000 description 1
- 101000757160 Homo sapiens Aminopeptidase N Proteins 0.000 description 1
- 101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 1
- 241001450457 Mycobacterium phage Newman Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 238000001665 trituration Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7304057A FR2216273B1 (enExample) | 1973-02-06 | 1973-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1026318A true CA1026318A (en) | 1978-02-14 |
Family
ID=9114388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,844A Expired CA1026318A (en) | 1973-02-06 | 1974-02-05 | Preparation process for spirolactone steroids |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3897417A (enExample) |
| JP (1) | JPS5829320B2 (enExample) |
| AT (1) | AT336811B (enExample) |
| BE (1) | BE810643A (enExample) |
| CA (1) | CA1026318A (enExample) |
| CH (2) | CH609710A5 (enExample) |
| DK (1) | DK134818B (enExample) |
| ES (2) | ES422921A1 (enExample) |
| FR (1) | FR2216273B1 (enExample) |
| GB (1) | GB1451843A (enExample) |
| IE (1) | IE39329B1 (enExample) |
| LU (1) | LU69328A1 (enExample) |
| NL (1) | NL179288C (enExample) |
| SE (2) | SE399270B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4058522A (en) * | 1973-07-09 | 1977-11-15 | Richter Gedeon Vegyeszeti Gyar Rt. | Steroids effective against heavy-metal poisoning |
| IT1130924B (it) * | 1980-03-06 | 1986-06-18 | Secifarma Spa | Procedimento per la preparazione di spironolattone micronizzato |
| US4501695A (en) * | 1983-05-16 | 1985-02-26 | The Upjohn Company | Spironalactone process |
| DK0973791T3 (da) * | 1995-12-11 | 2007-09-17 | Searle Llc | Fremgangsmåde til fremstilling af en epoxyforbindelse |
| US6887991B1 (en) | 1996-12-11 | 2005-05-03 | G. D. Searle & Company | Processes for preparation of 9, 11-epoxy steroids and intermediates useful therein |
| NZ336004A (en) | 1996-12-11 | 2001-04-27 | G | Process for preparation of 3-keto-7-alpha-alkoxycarbonyl substituted delta-4,5-steroid by reacting 4,5-dihydro-5,7-lactone steroid substrate in the presence of a base |
| RU2163606C1 (ru) * | 1999-12-08 | 2001-02-27 | Андрюшина Валентина Александровна | СПОСОБ ПОЛУЧЕНИЯ γ-ЛАКТОНА 3(7α-АЦЕТИЛТИО-17β-ГИДРОКСИ-3-ОКСОАНДРОСТ-4-ЕН-17α-ИЛ)ПРОПИОНОВОЙ КИСЛОТЫ |
| KR20050028907A (ko) * | 2002-03-22 | 2005-03-23 | 파마시아 코포레이션 | 스테로이드의 ｃ-17 스피롤락톤화 및 6,7 산화 |
| US7235655B2 (en) * | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1329570A (fr) * | 1959-12-10 | 1963-06-14 | Searle & Co | Procédé de préparation des lactones d'alcanoylthio-17alpha-carboxyéthyl-17bêta-hydroxy-3-oxoandrostènes |
| US3257390A (en) * | 1963-06-12 | 1966-06-21 | Merck & Co Inc | Ring a unsaturated 21-hydroxy-3-oxo-17alpha-pregnane-17-carboxylic acid lactone diuretic agents |
| US3300489A (en) * | 1964-07-24 | 1967-01-24 | Smith Kline French Lab | Steroidal c-17 spirolactones and processes and intermediates used in the preparation thereof |
-
1973
- 1973-02-06 FR FR7304057A patent/FR2216273B1/fr not_active Expired
-
1974
- 1974-02-01 US US438601A patent/US3897417A/en not_active Expired - Lifetime
- 1974-02-05 BE BE140580A patent/BE810643A/xx unknown
- 1974-02-05 ES ES422921A patent/ES422921A1/es not_active Expired
- 1974-02-05 CH CH385975A patent/CH609710A5/xx not_active IP Right Cessation
- 1974-02-05 CA CA191,844A patent/CA1026318A/en not_active Expired
- 1974-02-05 LU LU69328A patent/LU69328A1/xx unknown
- 1974-02-05 SE SE7401494A patent/SE399270B/xx not_active IP Right Cessation
- 1974-02-05 CH CH158474A patent/CH595399A5/xx not_active IP Right Cessation
- 1974-02-06 JP JP49014627A patent/JPS5829320B2/ja not_active Expired
- 1974-02-06 DK DK62574AA patent/DK134818B/da not_active IP Right Cessation
- 1974-02-06 AT AT92174A patent/AT336811B/de not_active IP Right Cessation
- 1974-02-06 NL NLAANVRAGE7401656,A patent/NL179288C/xx not_active IP Right Cessation
- 1974-02-06 IE IE226/74A patent/IE39329B1/xx unknown
- 1974-02-06 GB GB545174A patent/GB1451843A/en not_active Expired
-
1976
- 1976-01-07 ES ES444112A patent/ES444112A1/es not_active Expired
-
1977
- 1977-06-03 SE SE7706509A patent/SE440782B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH609710A5 (enExample) | 1979-03-15 |
| IE39329L (en) | 1974-08-06 |
| FR2216273A1 (enExample) | 1974-08-30 |
| CH595399A5 (enExample) | 1978-02-15 |
| ATA92174A (de) | 1976-09-15 |
| ES422921A1 (es) | 1976-09-16 |
| LU69328A1 (enExample) | 1974-09-25 |
| ES444112A1 (es) | 1977-08-16 |
| DK134818B (da) | 1977-01-24 |
| NL179288C (nl) | 1986-08-18 |
| IE39329B1 (en) | 1978-09-13 |
| US3897417A (en) | 1975-07-29 |
| DK134818C (enExample) | 1977-06-13 |
| GB1451843A (en) | 1976-10-06 |
| AU6521174A (en) | 1975-08-07 |
| SE440782B (sv) | 1985-08-19 |
| BE810643A (fr) | 1974-08-05 |
| SE7706509L (sv) | 1977-06-03 |
| FR2216273B1 (enExample) | 1977-07-22 |
| JPS5829320B2 (ja) | 1983-06-22 |
| JPS49109365A (enExample) | 1974-10-17 |
| NL179288B (nl) | 1986-03-17 |
| SE399270B (sv) | 1978-02-06 |
| NL7401656A (enExample) | 1974-08-08 |
| AT336811B (de) | 1977-05-25 |
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