GB1218998A - Process for preparing 15-hydroxy-9-oxoprost-13-enoic acid - Google Patents
Process for preparing 15-hydroxy-9-oxoprost-13-enoic acidInfo
- Publication number
- GB1218998A GB1218998A GB5539568A GB5539568A GB1218998A GB 1218998 A GB1218998 A GB 1218998A GB 5539568 A GB5539568 A GB 5539568A GB 5539568 A GB5539568 A GB 5539568A GB 1218998 A GB1218998 A GB 1218998A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- acid
- oxoprost
- enoic acid
- alkanol
- 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
- DPNOTBLPQOITGU-PXKIYYGHSA-N 7-[(1r,2r)-2-(3-hydroxyoct-1-enyl)-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCCC(O)C=C[C@H]1CCC(=O)[C@@H]1CCCCCCC(O)=O DPNOTBLPQOITGU-PXKIYYGHSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- DFYVYWIESAANFD-CXEJCQMISA-N 7-[(1r,5r)-2-hydroxy-5-(3-oxooct-1-enyl)cyclopentyl]heptanoic acid Chemical compound CCCCCC(=O)C=C[C@H]1CCC(O)[C@@H]1CCCCCCC(O)=O DFYVYWIESAANFD-CXEJCQMISA-N 0.000 abstract 1
- PIJUXNSVCKLTHQ-MWGBXKHISA-N CC(C(=O)O)CCCCC[C@H]1C(CC[C@@H]1C=CC(CCCCC)OC(C)=O)O Chemical compound CC(C(=O)O)CCCCC[C@H]1C(CC[C@@H]1C=CC(CCCCC)OC(C)=O)O PIJUXNSVCKLTHQ-MWGBXKHISA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- XPNANRSRZDKWKD-XRRBNZLQSA-N methyl 7-[(1r,5r)-2-hydroxy-5-(3-oxooct-1-enyl)cyclopentyl]heptanoate Chemical compound CCCCCC(=O)C=C[C@H]1CCC(O)[C@@H]1CCCCCCC(=O)OC XPNANRSRZDKWKD-XRRBNZLQSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- -1 p-methoxy benzyl ethers Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001412 tetrahydropyranyl 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,218,998. Prostanoic acid derivatives and related compounds. AYERST McKENNA & HARRISON Ltd. 21 Nov., 1968 [25 Nov., 1967], No. 55395/68. Heading C2C. 15 - Hydroxy - 9 - oxoprost - 13 - enoic acid and its novel C 1-4 alkyl esters are prepared (a) for the esters, by hydrolysis of the corresponding 15-C 1-4 alkanoates with an alkali metal carbonate in an aqueous C 1-4 alkanol; or (b) for the acid, by hydrolysis of the esters or their 15-C 1-4 alkanoates with an alkali or alkaline earth metal hydroxide in an aqueous C 1-4 alkanol. The starting materials are in turn prepared by esterifying 9-hydroxy-15-oxoprost- 13-enoic acid with an alkanol in the presence of an acid, etherifying the ester to yield the corresponding 9-ether, reducing this with an alkali metal borohydride in a solvent to give the 15-ol, converting this to its acylate, removing the etherifying group by acid hydrolysis, and oxidizing the product. Novel intermediates are methyl 9-hydroxy-15-oxoprost-13-enoate and its tetrahydropyranyl and p-methoxy benzyl ethers, the same ethers of methyl 9,15-dihydroxyprost-13-enoic acid and of the corresponding 15- acetoxy compound, and methyl 15-acetoxy-9- hydroxyprost-13-enoic acid and the corresponding 9-oxo compound. The 15-hydroxy and -alkanoyloxy compounds are a mixture of the alpha and beta isomers. 15 - Hydroxy - 9 - oxoprost - 13 - enoic acid and its alkyl esters are hypotensive agents, and they may be made up into pharmaceutical compositions with suitable carriers. Reference has been directed by the Comptroller to Specification 1,097,533.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA6110 | 1967-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1218998A true GB1218998A (en) | 1971-01-13 |
Family
ID=4083920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5539568A Expired GB1218998A (en) | 1967-11-25 | 1968-11-21 | Process for preparing 15-hydroxy-9-oxoprost-13-enoic acid |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA886591A (en) |
| CH (1) | CH558771A (en) |
| DE (1) | DE1810824A1 (en) |
| GB (1) | GB1218998A (en) |
| NL (1) | NL6816804A (en) |
| SE (1) | SE357961B (en) |
-
1967
- 1967-11-25 CA CA886591A patent/CA886591A/en not_active Expired
-
1968
- 1968-11-21 GB GB5539568A patent/GB1218998A/en not_active Expired
- 1968-11-22 SE SE1596068A patent/SE357961B/xx unknown
- 1968-11-25 NL NL6816804A patent/NL6816804A/xx unknown
- 1968-11-25 DE DE19681810824 patent/DE1810824A1/en active Pending
- 1968-11-25 CH CH1752768A patent/CH558771A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA886591A (en) | 1971-11-23 |
| DE1810824A1 (en) | 1969-07-10 |
| SE357961B (en) | 1973-07-16 |
| CH558771A (en) | 1975-02-14 |
| NL6816804A (en) | 1969-05-28 |
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