IE45609L - Process for the preparation of prostaglandins - Google Patents
Process for the preparation of prostaglandinsInfo
- Publication number
- IE45609L IE45609L IE771407A IE140777A IE45609L IE 45609 L IE45609 L IE 45609L IE 771407 A IE771407 A IE 771407A IE 140777 A IE140777 A IE 140777A IE 45609 L IE45609 L IE 45609L
- Authority
- IE
- Ireland
- Prior art keywords
- prostaglandins
- toluenesulfinyl
- phenylsulfinyl
- methylsulfinyl
- para
- Prior art date
Links
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 3
- 150000003180 prostaglandins Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- -1 phenylsulfinyl Chemical group 0.000 abstract 2
- MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of formula: <IMAGE> in which R represents hydrogen or a C1-C4 alkyl, R1 represents hydrogen or a methyl, X represents oxygen or a methylene and R2 represents a C1-C4 alkyl are prepared by treating the corresponding disubstituted cyclopentanone with a methylsulfinyl, phenylsulfinyl or para-toluenesulfinyl halide in the presence of a strong base, and by then heating the 2-(methylsulfinyl, phenylsulfinyl or para-toluenesulfinyl)cyclopentanone thus formed. The compounds (I) can be used as intermediates in the synthesis of prostaglandins or they themselves have properties analogous to those of prostaglandins; it is thus possible to prepare, especially, prostaglandin A2 more satisfactorily than by the prior processes.
[GB1538037A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7620769A FR2357542A1 (en) | 1976-07-07 | 1976-07-07 | PROCESS FOR THE PREPARATION OF PROSTAGLANDIN A2 AND SOME OF ITS DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45609L true IE45609L (en) | 1978-01-07 |
| IE45609B1 IE45609B1 (en) | 1982-10-06 |
Family
ID=9175362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1407/77A IE45609B1 (en) | 1976-07-07 | 1977-07-06 | Process for the preparation of prostaglandins |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS537649A (en) |
| BE (1) | BE856545A (en) |
| CA (1) | CA1087614A (en) |
| CH (1) | CH622247A5 (en) |
| DE (1) | DE2730762A1 (en) |
| DK (1) | DK303977A (en) |
| FR (1) | FR2357542A1 (en) |
| GB (1) | GB1538037A (en) |
| HU (1) | HU178334B (en) |
| IE (1) | IE45609B1 (en) |
| LU (1) | LU77693A1 (en) |
| NL (1) | NL7707458A (en) |
| SE (1) | SE420091B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5338844A (en) * | 1989-10-19 | 1994-08-16 | Teijin Limited | 2-substituted-2-cyclopentenone compound and anticancer agent and bone formation accelerator comprising same as active ingredient |
| WO1991005766A1 (en) * | 1989-10-19 | 1991-05-02 | Teijin Limited | 2-substituted 2-cyclopentenone and carcinostatic agent and osteogenesis promoter containing the same as active ingredient |
| JP6739754B2 (en) | 2015-03-09 | 2020-08-12 | 三菱瓦斯化学株式会社 | Method for isomerizing diaminodicyclohexylmethane |
-
1976
- 1976-07-07 FR FR7620769A patent/FR2357542A1/en active Granted
-
1977
- 1977-06-16 SE SE7706998A patent/SE420091B/en unknown
- 1977-06-20 HU HU77RO933A patent/HU178334B/en unknown
- 1977-07-05 NL NL7707458A patent/NL7707458A/en not_active Application Discontinuation
- 1977-07-06 DK DK303977A patent/DK303977A/en not_active Application Discontinuation
- 1977-07-06 CA CA282,191A patent/CA1087614A/en not_active Expired
- 1977-07-06 BE BE179126A patent/BE856545A/en not_active IP Right Cessation
- 1977-07-06 LU LU77693A patent/LU77693A1/xx unknown
- 1977-07-06 IE IE1407/77A patent/IE45609B1/en unknown
- 1977-07-07 DE DE19772730762 patent/DE2730762A1/en not_active Withdrawn
- 1977-07-07 CH CH840477A patent/CH622247A5/en not_active IP Right Cessation
- 1977-07-07 JP JP8050777A patent/JPS537649A/en active Pending
- 1977-07-07 GB GB28566/77A patent/GB1538037A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1538037A (en) | 1979-01-10 |
| CH622247A5 (en) | 1981-03-31 |
| DK303977A (en) | 1978-01-08 |
| NL7707458A (en) | 1978-01-10 |
| SE7706998L (en) | 1978-01-08 |
| IE45609B1 (en) | 1982-10-06 |
| FR2357542A1 (en) | 1978-02-03 |
| LU77693A1 (en) | 1978-01-31 |
| JPS537649A (en) | 1978-01-24 |
| HU178334B (en) | 1982-04-28 |
| CA1087614A (en) | 1980-10-14 |
| SE420091B (en) | 1981-09-14 |
| DE2730762A1 (en) | 1978-01-12 |
| FR2357542B1 (en) | 1979-07-06 |
| BE856545A (en) | 1978-01-06 |
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