GB1341780A - Cyclopenteneheptanoic acid derivatives - Google Patents
Cyclopenteneheptanoic acid derivativesInfo
- Publication number
- GB1341780A GB1341780A GB5910971A GB5910971A GB1341780A GB 1341780 A GB1341780 A GB 1341780A GB 5910971 A GB5910971 A GB 5910971A GB 5910971 A GB5910971 A GB 5910971A GB 1341780 A GB1341780 A GB 1341780A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- oxocyclopent
- methoxy
- octyn
- hydroxy
- 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
- RQUIUZWLNMSDHI-UHFFFAOYSA-N 7-(cyclopenten-1-yl)heptanoic acid Chemical class OC(=O)CCCCCCC1=CCCC1 RQUIUZWLNMSDHI-UHFFFAOYSA-N 0.000 title abstract 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- LVXPDCZDLYJCST-UHFFFAOYSA-N 7-(4-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoic acid Chemical compound COC1=C(CCCCCCC(O)=O)C(=O)C(O)C1 LVXPDCZDLYJCST-UHFFFAOYSA-N 0.000 abstract 3
- VUGRNZHKYVHZSN-UHFFFAOYSA-N oct-1-yn-3-ol Chemical compound CCCCCC(O)C#C VUGRNZHKYVHZSN-UHFFFAOYSA-N 0.000 abstract 3
- -1 1 - Octyn - 3 - yl Chemical group 0.000 abstract 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- VUGRNZHKYVHZSN-QMMMGPOBSA-N (3r)-oct-1-yn-3-ol Chemical compound CCCCC[C@@H](O)C#C VUGRNZHKYVHZSN-QMMMGPOBSA-N 0.000 abstract 1
- VUGRNZHKYVHZSN-MRVPVSSYSA-N (3s)-oct-1-yn-3-ol Chemical compound CCCCC[C@H](O)C#C VUGRNZHKYVHZSN-MRVPVSSYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- YNXXIKVLODBVEE-UHFFFAOYSA-N 7-(2,3,5-trioxocyclopentyl)heptanoic acid Chemical compound OC(=O)CCCCCCC1C(=O)CC(=O)C1=O YNXXIKVLODBVEE-UHFFFAOYSA-N 0.000 abstract 1
- ASUMHSZQZHAHEA-UHFFFAOYSA-N 7-(3-hydroxy-2,5-dioxocyclopentyl)heptanoic acid Chemical compound OC1CC(=O)C(CCCCCCC(O)=O)C1=O ASUMHSZQZHAHEA-UHFFFAOYSA-N 0.000 abstract 1
- VXOUZNCTJGLWBZ-UHFFFAOYSA-N 7-[2-methoxy-4-(methoxymethoxy)-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound COCOC1CC(OC)=C(CCCCCCC(O)=O)C1=O VXOUZNCTJGLWBZ-UHFFFAOYSA-N 0.000 abstract 1
- LFMPQNTXQKMBIJ-UHFFFAOYSA-N 7-[3-(2-methoxy-2-oxoacetyl)-2,4,5-trioxocyclopentyl]heptanoic acid Chemical compound COC(=O)C(=O)C1C(=O)C(CCCCCCC(O)=O)C(=O)C1=O LFMPQNTXQKMBIJ-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000026 anti-ulcerogenic effect Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- ZWTFZHTWWSBTAB-UHFFFAOYSA-N methyl 7-(3-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=C(OC)C(O)CC1=O ZWTFZHTWWSBTAB-UHFFFAOYSA-N 0.000 abstract 1
- GWJWJDLPXYCVTI-UHFFFAOYSA-N methyl 7-(4-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=C(OC)CC(O)C1=O GWJWJDLPXYCVTI-UHFFFAOYSA-N 0.000 abstract 1
- NXPZVRGRPMXLTL-UHFFFAOYSA-N methyl 7-[2-methoxy-4-(methoxymethoxy)-5-oxocyclopenten-1-yl]heptanoate Chemical compound COC1=C(C(C(C1)OCOC)=O)CCCCCCC(=O)OC NXPZVRGRPMXLTL-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000004936 stimulating effect Effects 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
Abstract
1341780 Cyclopenteneheptanoic acids G D SEARLE & CO 20 Dec 1971 [21 Dec 1970] 59109/71 Headings C2C and C2U Novel cyclopenteneheptanoic acid derivatives of the formula wherein R is H or C 1-7 alkyl and the wavy line indicates the (R) or (S) isomer are prepared by reacting 5-hydroxy-5(3(R) or 3(S)-tetrahydropyran - 2<SP>1</SP> - yloxy - 1 - octynyl) - 4 - methoxymethoxy - 2 - methoxycyclopent - 1 - eneheptanoic acid or by reacting 2-methoxy-4-hydroxy- 5-oxocyclopent-1-eneheptanoic acid with 3(R) or 3(S) 3-tetrahydropyran-2<SP>1</SP>-yloxy-1-octynyl magnesium bromide and decomposition of the resulting Grignard adduct, followed by, if desired, esterification. The following intermediates are prepared: 2,3,5 - trioxo - 4 - methoxalylcyclopentaneheptanoic acid, 2,3,5 - trioxocyclopentaneheptanoic acid, 2,5 - dioxo - 3 - hydroxycyclopentaneheptanoic acid, 2-methoxy-4-hydroxy-5-oxocyclopent - 1 - eneheptanoate, methyl 2- methoxy - 3 - hydroxy - 5 - oxocyclopent - 1- eneheptanoate, methyl 2 - methoxy - 4 - methoxymethoxy - 5 - oxocyclopent - 1 - eneheptanoate, 2 - methoxy - 4 - methoxymethoxy - 5- oxocyclopent - 1 - eneheptanoic acid, 3(RS)- 1 - octyn - 3 - ol 3 - tetrahydropyran - 21 - yl ether, 3(S) 1 - octyn - 3 - ol, and its 2 - tetrahydropyranyl ether, 3(R) 1-octyn-3-ol, and its 2-tetrahydropyranyl ether, 5-hydroxy-5-[(3R)- 3 - tetrahydropyran - 2<SP>1</SP>- yloxy - 1 - octynyl]- 4 - methoxymethoxy - 2 - methoxycyclopent - 1- ene - heptanoic acid, 2 - methoxy - 4 - hydroxy- 5 - oxocyclopent - 1 - eneheptanoic acid, and 4,5 - dihydroxy - 5 - [(3R) - 3 - tetrahydropyran- 21 - yloxy - 1 - octynyl] - 2 - methoxycyclopent- 1-eneheptanoic acid. (3R) 1 - Octyn - 3 - yl 3# - acetoxyandrost - 5- ene-17#-carboxylate is obtained by reacting 3(RS) 1 - octyn - 3 - ol with 3# - acetoxyandrost- 5-ene-17#-carbonyl chloride resulting from reacting between the corresponding acid and thionyl chloride. (3S) 1 - Octyn - 3 - yl 3# - acetoxyandrosta- 5,16 - diene - 17# - carboxylate is prepared by reacting 3(RS) 1-octyn-3-ol with 3#-acetoxyandrosta-5,16-diene-17#-carbonyl chloride, obtained by reacting the appropriate acid with thionyl chloride. 1 - (6 - Methoxycarbonythexyl) - 2 - methoxy- 5 - oxocyclopent - 1 - en - 4 - yl 3# - acetoxyandrosta - 5,16 - diene - 17# - carboxylate is made by reacting the appropriate carbonyl chloride with methyl 2 - methoxy - 4 - hydroxy - 5 - oxocyclopent-1-eneheptanoate Pharmaceutical compositions, suitable for parenteral administration, contain the above novel compounds and pharmaceutically acceptable diluents and carriers. The compounds possess hypotensive, smooth muscle-stimulating and anti-ulcerogenic properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10042070A | 1970-12-21 | 1970-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1341780A true GB1341780A (en) | 1973-12-25 |
Family
ID=22279681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5910971A Expired GB1341780A (en) | 1970-12-21 | 1971-12-20 | Cyclopenteneheptanoic acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT322748B (en) |
| AU (1) | AU3709571A (en) |
| BE (1) | BE777022A (en) |
| DE (1) | DE2163115A1 (en) |
| FR (1) | FR2118953B1 (en) |
| GB (1) | GB1341780A (en) |
| ZA (1) | ZA718548B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1402666A (en) * | 1972-06-12 | 1975-08-13 | Searle & Co | Acetlylenic cyclopentenealkanoic acids and processes for their preparation |
| US4172953A (en) * | 1973-03-30 | 1979-10-30 | G. D. Searle & Co. | 2,3,5-Trisubstituted cyclopentanealkenoic acids, derivatives thereof and intermediates thereto |
-
1971
- 1971-12-20 GB GB5910971A patent/GB1341780A/en not_active Expired
- 1971-12-20 AU AU37095/71A patent/AU3709571A/en not_active Expired
- 1971-12-20 FR FR7145762A patent/FR2118953B1/fr not_active Expired
- 1971-12-20 AT AT1091871A patent/AT322748B/en not_active IP Right Cessation
- 1971-12-20 DE DE19712163115 patent/DE2163115A1/en active Pending
- 1971-12-21 ZA ZA718548A patent/ZA718548B/en unknown
- 1971-12-21 BE BE777022A patent/BE777022A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2118953A1 (en) | 1972-08-04 |
| BE777022A (en) | 1972-06-21 |
| ZA718548B (en) | 1973-02-28 |
| AT322748B (en) | 1975-06-10 |
| AU3709571A (en) | 1973-06-28 |
| DE2163115A1 (en) | 1972-07-13 |
| FR2118953B1 (en) | 1975-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES420386A1 (en) | 16,17,18,19,20-pentanorprostaglandins | |
| SE7705637L (en) | PROCEDURE FOR THE PREPARATION OF DIBENSOXEPIN DERIVATIVES WITH THERAPEUTIC EFFECT | |
| GB1459564A (en) | Alkylphenyl benzopyrans | |
| GB1307455A (en) | 2,-hydroxy-3-phenylpropiophenone derivatives | |
| GB1511463A (en) | 1-acylamino methyl-1,2,3,4-tetrahydroisoquinolines | |
| GB1265279A (en) | ||
| GB1341780A (en) | Cyclopenteneheptanoic acid derivatives | |
| GB1252329A (en) | ||
| GB1399089A (en) | Carboxylic acids and derivatives thereof | |
| GB1427114A (en) | Derivatives of 3- p-chlorobenoyl-2-methyl-phenylacetic acid | |
| GB1494773A (en) | Hydroxyphenylalkanoic acids and lactones thereof | |
| GB1390402A (en) | Substituted imidazolecarboxamides | |
| GB1331505A (en) | Derivatives of thiophene acetic acid and processes for preparing them | |
| GB1391615A (en) | 4-oxo-4h-1-benzopyran and 4-oxo-4h-1-thia benzopyran derivatives | |
| GB1513280A (en) | Therapeutic pyrazole derivatives | |
| GB1369173A (en) | 5-cinnamoyl-pyrrole-2-acetic acids and esters and pharmaceutical compositions containing them | |
| GB1337198A (en) | Oestratriene diethers | |
| GB1317224A (en) | 5,8-dihydronaphthyloxy acetic acids | |
| GB1183841A (en) | Prostaglandin Related Compounds | |
| GB1242096A (en) | Benzobenzofuranooxepine compounds and process for preparing the same | |
| IE34139L (en) | 4-phenyl-butyric acid derivatives | |
| GB1412663A (en) | 2- 4-biphenylyl- tetrahydrofurans and pharmaceutical compositions containing them | |
| GB1384024A (en) | Process for the preparation of 3-hydroxy-2-3-hydroxy-1-octenyl- 5-oxocyclopentane-heptanoic acid and derivatives thereof | |
| GB1529852A (en) | 8-azaprostaglandins and process for the preparation thereof | |
| GB1223130A (en) | Tropine ester salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |