IE35553L - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- IE35553L IE35553L IE710080A IE8071A IE35553L IE 35553 L IE35553 L IE 35553L IE 710080 A IE710080 A IE 710080A IE 8071 A IE8071 A IE 8071A IE 35553 L IE35553 L IE 35553L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- alkyl
- cyclopentane derivatives
- acids
- oxo
- Prior art date
Links
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 239000002253 acid Substances 0.000 abstract 5
- 150000001940 cyclopentanes Chemical class 0.000 abstract 5
- 150000007513 acids Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004980 cyclopropylene group Chemical group 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- GXXQKJQWMVPECM-UHFFFAOYSA-N 7-[2-oxo-5-(3-oxooct-1-enyl)cyclopentyl]heptanoic acid Chemical compound CCCCCC(=O)C=CC1CCC(=O)C1CCCCCCC(O)=O GXXQKJQWMVPECM-UHFFFAOYSA-N 0.000 abstract 1
- WKRFBISWQTVSHD-UHFFFAOYSA-N 7-[2-oxo-5-(3-oxooctyl)cyclopentyl]heptanoic acid Chemical compound CCCCCC(=O)CCC1CCC(=O)C1CCCCCCC(O)=O WKRFBISWQTVSHD-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 229940124630 bronchodilator Drugs 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical class O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002081 enamines Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1352691 Cyclopentane derivatives MAY & BAKER Ltd 19 April 1971 [23 Jan 1970] 3494/70 Heading C2C Cyclopentane derivatives of the Formula I wherein R<SP>1</SP> is H or C 1-4 alkyl, R<SP>2</SP> is C 1-10 alkyl, the symbols R<SP>3</SP> are identical groups selected from H, C 1-4 alkyl, C 2-4 alkenyl, phenyl-C 1-4 alkyl, and C 2-5 alkanoyl, R<SP>4</SP> is COOH, CON- (R<SP>5</SP>)R 6 , CONHN(R<SP>5</SP>)R 6 , OONHC(=NR<SP>7</SP>)N(R<SP>5</SP>)- R 6 , or COOR<SP>8</SP>, wherein R<SP>5</SP>, R 6 and R<SP>7</SP> are the same or different and each is H or C 1-4 alkyl, and R<SP>8</SP> is C 1-4 alkyl, X is -CH=CH-, -CH 2 CH 2 -, epoxyethylene or cyclopropylene, and n is 5 to 8 are prepared by (i) reacting enamines of cyclopentanones of the formula with aldehydes of the formula wherein R<SP>9</SP> is H or a suitable acid labile group, followed by hydrolysis under aqueous acid conditions and then heating the products with acids to form 2-hydroxyalkyl-2-cyclopenten-1-ones of the formula (ii) reacting the 2-hydroxyalkyl-2-cyclopenten- 1-ones with a source of hydrogen cyanide in aqueous organic solvents to form ketonitriles of the formula (iii) reducing the ketonitriles in inert organic solvents with a complex metal reducing agent to give 3-hydroxy-2-hydroxyalkylcyclopentanecarbaldehydes of the formula (v) reacting the resulting 3-hydroxy-2-hydroxyalkylcyclopentanecarbaldehydes with alkanoylmethylene triphenyl- or trialkyl-phosphoranes of the formula (Q) 3 P=CH-CO-R<SP>2</SP>, wherein Q is phenyl, C 1-4 alkylphenyl or C 1-4 alkyl, in inert organic solvents to form unsaturated ketones of the formula (iv) oxidizing the unsaturated ketones to cyclopentanealkanoic acids of the formula (vi) reducing the cyclopentanealkanoic acids to yield acids of the Formula XIII and if desired converting products of Formula XIII so obtained to other cyclopentane derivatives of Formula I. The cyclopentane derivatives of Formula I above are novel provided that when n is 6 at least one of the various R symbols and X represents a group as specified below: R<SP>1</SP> is C 1-4 alkyl; R<SP>2</SP> is C 3-10 branched-chain alkyl; R<SP>3</SP> is C 1-4 alkyl, C 2-4 alkenyl or phenyl- C 1-4 alkyl; R<SP>4</SP> is CON(R<SP>5</SP>)R<SP>6</SP>, CONHN(R<SP>5</SP>)R<SP>6</SP> or CONHC(=NR<SP>7</SP>)N(R<SP>5</SP>)R<SP>6</SP>, X is epoxyethylene or cyclopropylene, the other R symbols and X having any of the meanings hereinbefore defined. 7 - [2 - Oxo - 5 - (3 - oxooctyl)cyclopentyl]heptanoic acid is made by catalytically reducing 7-[2- oxo - 5 - (3 - oxo - 1 - octenyl)cyclopentyl]- heptanoic acid. Pharmaceutical compositions, for oral, parenteral or rectal administration, contain the novel cyclopentane derivatives of Formula I above, or non-toxic salts thereof in association with pharmaceutical carriers or coatings. The compounds possess hypotensive and bronchodilator activities.
[GB1352691A]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE1792/75A IE35554B1 (en) | 1970-01-23 | 1971-01-22 | 2-hydroxyalkyl-2-cyclopenten-1-ones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB349470 | 1970-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35553L true IE35553L (en) | 1971-07-23 |
| IE35553B1 IE35553B1 (en) | 1976-03-18 |
Family
ID=9759395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE80/71A IE35553B1 (en) | 1970-01-23 | 1971-01-22 | Cyclopentane derivatives |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE761944A (en) |
| CH (1) | CH535197A (en) |
| DE (1) | DE2103005A1 (en) |
| FR (2) | FR2081449A1 (en) |
| GB (1) | GB1352691A (en) |
| HU (1) | HU162280B (en) |
| IE (1) | IE35553B1 (en) |
| NL (1) | NL7100904A (en) |
| PL (1) | PL72989B1 (en) |
| SE (1) | SE374105B (en) |
| ZA (1) | ZA71435B (en) |
-
1970
- 1970-01-23 GB GB3494/70*2A patent/GB1352691A/en not_active Expired
-
1971
- 1971-01-20 FR FR7101791A patent/FR2081449A1/fr not_active Withdrawn
- 1971-01-21 PL PL1971145759A patent/PL72989B1/pl unknown
- 1971-01-21 HU HUMA2184A patent/HU162280B/hu unknown
- 1971-01-22 IE IE80/71A patent/IE35553B1/en unknown
- 1971-01-22 DE DE19712103005 patent/DE2103005A1/en active Pending
- 1971-01-22 NL NL7100904A patent/NL7100904A/xx unknown
- 1971-01-22 ZA ZA710435A patent/ZA71435B/en unknown
- 1971-01-22 CH CH94471A patent/CH535197A/en not_active IP Right Cessation
- 1971-01-22 BE BE761944A patent/BE761944A/en unknown
- 1971-01-22 SE SE7100783A patent/SE374105B/xx unknown
-
1977
- 1977-02-17 FR FR7704506A patent/FR2338258A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PL72989B1 (en) | 1974-08-30 |
| SE374105B (en) | 1975-02-24 |
| CH535197A (en) | 1973-03-31 |
| FR2338258A1 (en) | 1977-08-12 |
| BE761944A (en) | 1971-07-22 |
| GB1352691A (en) | 1974-05-08 |
| DE2103005A1 (en) | 1971-08-05 |
| IE35553B1 (en) | 1976-03-18 |
| HU162280B (en) | 1973-01-29 |
| FR2081449A1 (en) | 1971-12-03 |
| ZA71435B (en) | 1971-10-27 |
| NL7100904A (en) | 1971-07-27 |
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