CH609682A5 - Process for the preparation of compounds analogous to prostaglandins - Google Patents
Process for the preparation of compounds analogous to prostaglandinsInfo
- Publication number
- CH609682A5 CH609682A5 CH83176A CH83176A CH609682A5 CH 609682 A5 CH609682 A5 CH 609682A5 CH 83176 A CH83176 A CH 83176A CH 83176 A CH83176 A CH 83176A CH 609682 A5 CH609682 A5 CH 609682A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- prostaglandins
- preparation
- compounds analogous
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 2
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 230000001262 anti-secretory effect Effects 0.000 abstract 1
- 230000003182 bronchodilatating effect Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000003529 luteolytic effect Effects 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The compounds of formula I, in which A is -CH2-CH2 or cis -CH=CH-, B is trans -CH=CH-, R is H, alkyl or a cation, R1 and R2 are alkyls and R3 is H or CH3, are prepared by condensation of an aldehyde of formula II with a phosphonic ester of formula (CH3O)2PO-CH2-CO-C(R3)-(OR1)R2. The 15-keto group can then be reduced to the hydroxyl group and the 9 alpha -hydroxy group can then be oxidised to the oxo radical. All these derivatives have luteolytic, antihypertensive, bronchodilatory and antisecretory pharmacological activity analogous to that of natural prostaglandins. <IMAGE>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3248/75A GB1538871A (en) | 1975-01-24 | 1975-01-24 | Prostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH609682A5 true CH609682A5 (en) | 1979-03-15 |
Family
ID=9754749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH83176A CH609682A5 (en) | 1975-01-24 | 1976-01-23 | Process for the preparation of compounds analogous to prostaglandins |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6024098B2 (en) |
| AR (1) | AR212328A1 (en) |
| AT (1) | AT351186B (en) |
| BE (1) | BE837865A (en) |
| CA (1) | CA1076569A (en) |
| CH (1) | CH609682A5 (en) |
| CS (1) | CS187333B2 (en) |
| DD (1) | DD122517A5 (en) |
| DE (1) | DE2601646A1 (en) |
| DK (1) | DK27376A (en) |
| FI (1) | FI64578C (en) |
| FR (1) | FR2298322A1 (en) |
| GB (1) | GB1538871A (en) |
| GR (1) | GR58537B (en) |
| HU (1) | HU174185B (en) |
| IE (1) | IE43821B1 (en) |
| IL (1) | IL48870A (en) |
| LU (1) | LU74240A1 (en) |
| NL (1) | NL185203C (en) |
| NO (1) | NO147714C (en) |
| NZ (1) | NZ179816A (en) |
| PH (1) | PH14040A (en) |
| PT (1) | PT64737B (en) |
| RO (1) | RO71901A (en) |
| SE (1) | SE446726B (en) |
| SU (1) | SU607550A3 (en) |
| YU (1) | YU40805B (en) |
| ZA (1) | ZA7681B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4064350A (en) * | 1976-11-22 | 1977-12-20 | G. D. Searle & Co. | 15,16-Dihydroxyprostaglandins |
| US4194055A (en) * | 1976-03-03 | 1980-03-18 | American Cyanamid Company | 15,16-dioxy prostenoic acids and esters |
| IT1162731B (en) * | 1979-04-10 | 1987-04-01 | Lepetit Spa | 16-METHYL-16-METHOXY-5,6-DIHYDRO-PROSTA-GLANDINE OF THE E1 SERIES WITH ANTI-SECRETORY ACTIVITY |
| JPS56162014A (en) * | 1980-05-16 | 1981-12-12 | Nippon Denso Co Ltd | Measuring device for flow rate of gas |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1392716A (en) * | 1971-05-11 | 1975-04-30 | Ici Ltd | Moulding |
| US4304907A (en) * | 1972-05-10 | 1981-12-08 | The Upjohn Company | Bicyclo lactone intermediates for prostaglandin analogs |
-
1975
- 1975-01-24 GB GB3248/75A patent/GB1538871A/en not_active Expired
-
1976
- 1976-01-05 FI FI760002A patent/FI64578C/en not_active IP Right Cessation
- 1976-01-07 ZA ZA00760081A patent/ZA7681B/en unknown
- 1976-01-09 GR GR49742A patent/GR58537B/en unknown
- 1976-01-15 YU YU111/76A patent/YU40805B/en unknown
- 1976-01-16 CS CS76305A patent/CS187333B2/en unknown
- 1976-01-17 DE DE19762601646 patent/DE2601646A1/en active Granted
- 1976-01-19 IL IL48870A patent/IL48870A/en unknown
- 1976-01-21 AT AT36776A patent/AT351186B/en not_active IP Right Cessation
- 1976-01-21 RO RO7684563A patent/RO71901A/en unknown
- 1976-01-22 PH PH18006A patent/PH14040A/en unknown
- 1976-01-22 FR FR7601707A patent/FR2298322A1/en active Granted
- 1976-01-22 IE IE120/76A patent/IE43821B1/en unknown
- 1976-01-22 DD DD190915A patent/DD122517A5/xx unknown
- 1976-01-23 SE SE7600729A patent/SE446726B/en not_active IP Right Cessation
- 1976-01-23 JP JP51006567A patent/JPS6024098B2/en not_active Expired
- 1976-01-23 LU LU74240A patent/LU74240A1/xx unknown
- 1976-01-23 DK DK27376*#A patent/DK27376A/en not_active Application Discontinuation
- 1976-01-23 AR AR262009A patent/AR212328A1/en active
- 1976-01-23 HU HU76LE788A patent/HU174185B/en not_active IP Right Cessation
- 1976-01-23 NL NLAANVRAGE7600696,A patent/NL185203C/en not_active IP Right Cessation
- 1976-01-23 CA CA244,132A patent/CA1076569A/en not_active Expired
- 1976-01-23 CH CH83176A patent/CH609682A5/en not_active IP Right Cessation
- 1976-01-23 NZ NZ179816A patent/NZ179816A/en unknown
- 1976-01-23 SU SU762311606A patent/SU607550A3/en active
- 1976-01-23 NO NO760214A patent/NO147714C/en unknown
- 1976-01-23 BE BE163765A patent/BE837865A/en not_active IP Right Cessation
- 1976-01-23 PT PT64737A patent/PT64737B/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |