CA1025436A - Process for preparing new dieono-derivatives of androstane series - Google Patents
Process for preparing new dieono-derivatives of androstane seriesInfo
- Publication number
- CA1025436A CA1025436A CA191,777A CA191777A CA1025436A CA 1025436 A CA1025436 A CA 1025436A CA 191777 A CA191777 A CA 191777A CA 1025436 A CA1025436 A CA 1025436A
- Authority
- CA
- Canada
- Prior art keywords
- représente
- produit
- formule
- que
- atome
- 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
- 150000001441 androstanes Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 17
- 239000011734 sodium Substances 0.000 claims 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 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- 230000009471 action Effects 0.000 claims description 6
- 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 claims description 6
- 208000037656 Respiratory Sounds Diseases 0.000 claims description 5
- 206010037833 rales Diseases 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims 6
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims 5
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound 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 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- -1 alkyl radical Chemical class 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000003003 spiro group Chemical group 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001331845 Equus asinus x caballus Species 0.000 description 4
- 241000927721 Tritia Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 241001212606 Ambia Species 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- 101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241001644893 Entandrophragma utile Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 241001190935 Lascoria aon Species 0.000 description 1
- 241000286819 Malo Species 0.000 description 1
- 101100202896 Mus musculus Selenoo gene Proteins 0.000 description 1
- 101100037618 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ant-1 gene Proteins 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- 229940059720 apra Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 101150008563 spir gene Proteins 0.000 description 1
- 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 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 101150058668 tra2 gene Proteins 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1025436A true CA1025436A (en) | 1978-01-31 |
Family
ID=9114389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,777A Expired CA1025436A (en) | 1973-02-06 | 1974-02-05 | Process for preparing new dieono-derivatives of androstane series |
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 |
| SE416950B (sv) | 1981-02-16 |
| 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 |
| 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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