GB1440602A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1440602A GB1440602A GB2306575A GB2306575A GB1440602A GB 1440602 A GB1440602 A GB 1440602A GB 2306575 A GB2306575 A GB 2306575A GB 2306575 A GB2306575 A GB 2306575A GB 1440602 A GB1440602 A GB 1440602A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- cyclopenta
- tetrahydropyranyl
- furan
- ones
- 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
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- -1 p-biphenylyl Chemical group 0.000 abstract 7
- HWLZQESIRAGTAT-UHFFFAOYSA-N cyclopenta[b]furan-2-one Chemical class C1=CC2=CC(=O)OC2=C1 HWLZQESIRAGTAT-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005594 diketone group Chemical group 0.000 abstract 3
- XSDLSEOIVCVTQZ-UHFFFAOYSA-N 2h-cyclopenta[b]furan Chemical class C1=CC2=CCOC2=C1 XSDLSEOIVCVTQZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- KZHCVXGCRMQOEP-UHFFFAOYSA-N 2h-cyclopenta[b]furan-2-ol Chemical class C1=CC2=CC(O)OC2=C1 KZHCVXGCRMQOEP-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical 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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1440602 Cyclopenta[b]furans PFIZER Inc 30 May 1973 [2 June 1972 30 April 1973] 23065/75 Divided out of 1440601 Heading C2C The invention comprises cyclopenta[b]furans of the formulµ wherein n is 0, 1 or 2; m is 0, 1, 2, 3 or 4; R 1 <SP>1</SP> is -COR 2 , wherein R 2 is C 1-5 alkyl, phenyl or p-biphenylyl; R is H or C 1-3 alkyl; R 1 is H, 2- tetrahydropyranyl or COR 2 ; and R 3 is H or 2-tetrahydropyranyl, with the proviso that when R 3 is 2-tetrahydropyranyl, R 1 is also 2- tetrahydropyranyl, and their preparation. The cyclopenta[b]furan-2-ols of Formula III above are prepared by reducing the corresponding cyclopenta[b]furan-2-ones of Formula II in which R 1 and R 3 are 2-tetrahydropyranyl, obtained by etherifying the corresponding compounds of Formula II in which R 1 and R 3 are both hydrogen, which are made by hydrolysing the corresponding cyclopenta[b]furan-2-ones of Formula II in which R 3 is 11 and R 1 is -COR 2 , the latter being obtained by either reducing the diketones of Formula I with sodium borohydride and separating the desired α-hydroxy isomers or by reacting the diketones of Formula I with C 1-3 alkyl lithiums and separating the desired α-hydroxy isomers. Diketones of Formula I are prepared by reacting phosphonates of the formula (CH 3 O) 2 PO.CH 2 .CO.(CH 2 ) 2 (CH 2 ) n O(CH 2 )mCH 3 with the appropriate 5α-acyloxy-3,3a#,4,5,6,- 6α# - hexahydro - 2 - oxo - 2H - cyclopenta[b]- furan - 4# - carboxaldehydes. Cyclopenta[b]- furan-2-ones of Formula IV above are obtained by hydrogenating the corresponding cyclopenta[b]furan-2-ones of Formula II in which R 1 and R 3 are both 2-tetrahydropyranyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25921572A | 1972-06-02 | 1972-06-02 | |
| US05/355,644 US4094899A (en) | 1972-06-02 | 1973-04-30 | Oxaprostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1440602A true GB1440602A (en) | 1976-06-23 |
Family
ID=26947161
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2306575A Expired GB1440602A (en) | 1972-06-02 | 1973-05-30 | Cyclopentane derivatives |
| GB2306775A Expired GB1440603A (en) | 1972-06-02 | 1973-05-30 | Alkyl phosphonates |
| GB2584673A Expired GB1440601A (en) | 1972-06-02 | 1973-05-30 | Oxaprostaglandins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2306775A Expired GB1440603A (en) | 1972-06-02 | 1973-05-30 | Alkyl phosphonates |
| GB2584673A Expired GB1440601A (en) | 1972-06-02 | 1973-05-30 | Oxaprostaglandins |
Country Status (19)
| Country | Link |
|---|---|
| JP (3) | JPS5314062B2 (en) |
| AR (2) | AR199300A1 (en) |
| CA (1) | CA1095034A (en) |
| CH (3) | CH590224A5 (en) |
| DD (2) | DD124594A5 (en) |
| DE (2) | DE2327813A1 (en) |
| DK (1) | DK143498C (en) |
| ES (2) | ES441002A1 (en) |
| FI (1) | FI55995C (en) |
| GB (3) | GB1440602A (en) |
| IE (1) | IE38568B1 (en) |
| IL (2) | IL42373A (en) |
| IN (1) | IN138739B (en) |
| LU (1) | LU67738A1 (en) |
| NL (1) | NL162902C (en) |
| NO (1) | NO145438C (en) |
| PH (3) | PH11300A (en) |
| SE (4) | SE415756B (en) |
| YU (1) | YU36497B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES416865A1 (en) * | 1972-07-13 | 1976-03-01 | Pfizer | 15-substituted-omega-pentanorprostaglandins |
| US11756356B2 (en) | 2019-08-28 | 2023-09-12 | Igloocompany Pte. Ltd. | System and method for controlling multiple locks |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538120A (en) * | 1967-05-22 | 1970-11-03 | Ciba Geigy Corp | Cyclopentyl-alkanoic acids |
| ZA721159B (en) * | 1971-03-22 | 1972-12-27 | Ici Ltd | Process for the separation of the c-15 epimers of 20-ethyl-9a,11alpha,15-trihydroxy-5-cis-13-trans-prostadienoic acid |
-
1973
- 1973-05-28 IL IL42373A patent/IL42373A/en unknown
- 1973-05-28 SE SE7307521A patent/SE415756B/en unknown
- 1973-05-28 IL IL7350311A patent/IL50311A/en unknown
- 1973-05-29 FI FI1735/73A patent/FI55995C/en active
- 1973-05-30 GB GB2306575A patent/GB1440602A/en not_active Expired
- 1973-05-30 GB GB2306775A patent/GB1440603A/en not_active Expired
- 1973-05-30 IN IN1265/CAL/73A patent/IN138739B/en unknown
- 1973-05-30 GB GB2584673A patent/GB1440601A/en not_active Expired
- 1973-06-01 CH CH797573A patent/CH590224A5/xx not_active IP Right Cessation
- 1973-06-01 IE IE881/73A patent/IE38568B1/en unknown
- 1973-06-01 DE DE2327813A patent/DE2327813A1/en not_active Withdrawn
- 1973-06-01 DE DE2344838A patent/DE2344838C3/en not_active Expired
- 1973-06-01 CH CH415576A patent/CH586716A5/xx not_active IP Right Cessation
- 1973-06-01 DK DK303973A patent/DK143498C/en not_active IP Right Cessation
- 1973-06-01 CH CH415476A patent/CH589074A5/xx not_active IP Right Cessation
- 1973-06-01 CA CA173,035A patent/CA1095034A/en not_active Expired
- 1973-06-02 JP JP6244973A patent/JPS5314062B2/ja not_active Expired
- 1973-06-04 AR AR248400A patent/AR199300A1/en active
- 1973-06-04 PH PH14690A patent/PH11300A/en unknown
- 1973-06-04 LU LU67738A patent/LU67738A1/xx unknown
- 1973-06-04 DD DD182818A patent/DD124594A5/xx unknown
- 1973-06-04 YU YU01469/73A patent/YU36497B/en unknown
- 1973-06-04 DD DD171300A patent/DD109859A5/xx unknown
- 1973-06-04 NL NL7307740.A patent/NL162902C/en not_active IP Right Cessation
-
1974
- 1974-01-29 AR AR252103A patent/AR203386A1/en active
- 1974-03-11 NO NO740849A patent/NO145438C/en unknown
-
1975
- 1975-04-07 PH PH17030A patent/PH12035A/en unknown
- 1975-04-07 PH PH17029A patent/PH11931A/en unknown
- 1975-09-16 ES ES441002A patent/ES441002A1/en not_active Expired
- 1975-09-16 ES ES441003A patent/ES441003A1/en not_active Expired
-
1976
- 1976-07-19 SE SE7608223A patent/SE7608223L/en not_active Application Discontinuation
- 1976-07-19 SE SE7608221A patent/SE418857B/en unknown
- 1976-07-19 SE SE7608222A patent/SE7608222L/en unknown
- 1976-09-08 JP JP51107650A patent/JPS5239629A/en active Pending
- 1976-09-08 JP JP51107651A patent/JPS5231054A/en active Granted
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |