GB1464300A - Prostaglandin derivatives - Google Patents
Prostaglandin derivativesInfo
- Publication number
- GB1464300A GB1464300A GB4154374A GB4154374A GB1464300A GB 1464300 A GB1464300 A GB 1464300A GB 4154374 A GB4154374 A GB 4154374A GB 4154374 A GB4154374 A GB 4154374A GB 1464300 A GB1464300 A GB 1464300A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydropyranyloxy
- cyclopenta
- sept
- prostaglandins
- compounds
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- YSVLXXDQJCNLEC-UHFFFAOYSA-N (4-carboxy-2-methylbutyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(CCC(O)=O)C)C1=CC=CC=C1 YSVLXXDQJCNLEC-UHFFFAOYSA-N 0.000 abstract 1
- -1 2 - tetrahydropyranyloxy Chemical group 0.000 abstract 1
- NKKSUZCCSQAZGI-UHFFFAOYSA-N 4-carboxypentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(C)C(O)=O)C1=CC=CC=C1 NKKSUZCCSQAZGI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1464300 Prostaglandins YAMANOUCHI PHARMACEUTICAL CO Ltd 24 Sept 1974 [25 Sept 1973 27 Sept 1973 15 April 1974] 41543/74 Heading C2C The invention comprises prostaglandins of the Formulµ I and II wherein A is C=O or C(H) ÀÀÀ OH; one of R 3 and R 4 is H and the other of them is C 1-4 alkyl; one of R 5 and R 6 is H and the other of them is hydroxy; and one of R 7 and R 8 is H and the other one of them is C 1-4 alkyl; one of R 1 and R 2 is H and the other of them is a protected hydroxy group; and R 9 is a protective group for a hydroxy group and their preparation. The compounds are prepared by reacting 4#-[3-(2- tetrahydropyranyloxy) - 4 - methyl - 1 - transoctenyl] - 5α - (2 - tetrahydropyranyloxy)- 3,3a#,4,5,6,6a# - hexahydro - 2H - cyclopenta- [b]furan - 2 - ol with (4 - carboxypentyl)triphenylphosphonium bromide or (4-carboxy-2- methylbutyl)triphenylphosphonium bromide, if desired, hydrolysing the resulting compounds, or oxidizing the products so obtained, and then hydrolysing the oxidation products. 4# - [3 - (2 - Tetrahydropyranlyoxy)- 4- methyl - 1 - trans - octenyl] - 5α - (2 - tetrahydropyranyloxy) - 3,3a#,4,5,6,6a# - hexahydro - 2H- cyclopenta[b]furan-2-ol is obtained by reducing the corresponding cyclopenta[b]p-uran-2-one. The compounds possess similar pharmacological properties to the corresponding naturally occurring prostaglandins.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10777273A JPS5058037A (en) | 1973-09-25 | 1973-09-25 | |
| JP10867473A JPS5058038A (en) | 1973-09-27 | 1973-09-27 | |
| JP4188574A JPS50140424A (en) | 1974-04-15 | 1974-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1464300A true GB1464300A (en) | 1977-02-09 |
Family
ID=27290986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4154374A Expired GB1464300A (en) | 1973-09-25 | 1974-09-24 | Prostaglandin derivatives |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2445251A1 (en) |
| ES (1) | ES430401A1 (en) |
| FR (1) | FR2244486B1 (en) |
| GB (1) | GB1464300A (en) |
-
1974
- 1974-09-20 FR FR7431833A patent/FR2244486B1/fr not_active Expired
- 1974-09-21 DE DE19742445251 patent/DE2445251A1/en active Pending
- 1974-09-24 GB GB4154374A patent/GB1464300A/en not_active Expired
- 1974-09-25 ES ES430401A patent/ES430401A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2244486B1 (en) | 1978-09-22 |
| DE2445251A1 (en) | 1975-04-03 |
| FR2244486A1 (en) | 1975-04-18 |
| ES430401A1 (en) | 1977-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |