GB1456040A - Prostaglandin 5-indanyl esters - Google Patents
Prostaglandin 5-indanyl estersInfo
- Publication number
- GB1456040A GB1456040A GB5983173A GB5983173A GB1456040A GB 1456040 A GB1456040 A GB 1456040A GB 5983173 A GB5983173 A GB 5983173A GB 5983173 A GB5983173 A GB 5983173A GB 1456040 A GB1456040 A GB 1456040A
- Authority
- GB
- United Kingdom
- Prior art keywords
- double bond
- yloxy
- prostaglandins
- formula
- indanyl esters
- 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
- -1 Prostaglandin 5-indanyl esters Chemical class 0.000 title abstract 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 6
- 150000003180 prostaglandins Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 5
- 150000002170 ethers Chemical class 0.000 abstract 2
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 abstract 2
- USCSRZNYDWXTMH-UHFFFAOYSA-N 2-(oxan-2-yloxyperoxy)oxane Chemical compound O1CCCCC1OOOC1OCCCC1 USCSRZNYDWXTMH-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000000699 topical effect Effects 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1456040 Indanyl esters of prostaglandins PFIZER Inc [8 Jan 1973] 27 Dec 1973 59831/73 Heading C2C The invention comprises indanyl esters of prostaglandins of the Formulµ I and II and the C 15 epimers thereof, wherein Y is a single or trans. double bond; W and Z each are single or cis-double bonds; R 1 is C = O, R 2 is H or alpha-hydroxy; and X is a single or double bond, with the provisos that when Z is a cis-double bond W is a cis-double bond, Y is a trans-double bond and X is a single bond, and that when X is a double bond R 1 is C = O and R 2 is H. The indanyl esters of the prostaglandins of the E and F series are prepared by hydrolysing the corresponding 11α,15α-bis- (2-tetrahhydropyranyl) ethers of Formula II above, which are obtained by reacting compounds of the Formula III and 15 epimers thereof, where R<SP>1</SP> 1 is with 5-indanol in the presence of N,N<SP>1</SP>-dicyclohexylcarbodiimide, and, if desired, oxidizing the resulting compounds. The indanyl esters of the prostaglandins of the A series are prepared by the acidic dehydration of the indanyl esters of the corresponding prostaglandins of the E series. The bis(2-tetrahydropronyl) ethers of Formula II above in which R 1 is may be prepared by reducing the corresponding compounds of Formula II in which R 1 is C 2 O with sodium borohydride. The following intermediates and starting materials are prepared: 5α-hydroxy-4#-(3#- hydroxy - oct - trans - 1 - enyl) - 3,3a#,4,5,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 - one and its bis(tetrahydro - pyran - 2 - yloxy) ether; 5α - (tetrahydropyran - 2 - yloxy) - 4#- [3# - (tetrahydropyran - 2 - yloxy)oct - trans - 1- enyl] - 3,3α#,4,5,6,6α# - hexahydro - 2H- cylopenta[b]furon - 2 - ol; 5α - (tetrahydropyran - 2 - yloxy) - 4# - [3# - (tetrahydropyran - 2 - yloxy)octyl] - 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta(b]furan - 2 - ol; and compounds of Formula III above and 15- opimers thereof. Pharmaceutical compositions, suitable for intravenous, oral, topical, intravaginal and intranasal administration, contain the above indanyl esters of Formula I together with suitable carriers or diluents. The compounds possess similar pharmacological properties to those of the naturally occurring prostaglandin. Reference has been directed by the Comptroller to Specifications 1,314,291, 1,314,292, 1,040,544, 1,097,533 and 1,097,157.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32166473A | 1973-01-08 | 1973-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1456040A true GB1456040A (en) | 1976-11-17 |
Family
ID=23251491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5983173A Expired GB1456040A (en) | 1973-01-08 | 1973-12-27 | Prostaglandin 5-indanyl esters |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5644069B2 (en) |
| BE (1) | BE809437A (en) |
| DE (1) | DE2365205A1 (en) |
| FR (2) | FR2221132B1 (en) |
| GB (1) | GB1456040A (en) |
| NL (1) | NL7400233A (en) |
-
1973
- 1973-12-27 GB GB5983173A patent/GB1456040A/en not_active Expired
- 1973-12-31 DE DE2365205A patent/DE2365205A1/en not_active Withdrawn
-
1974
- 1974-01-07 BE BE1005625A patent/BE809437A/en unknown
- 1974-01-08 FR FR7400601A patent/FR2221132B1/fr not_active Expired
- 1974-01-08 JP JP513774A patent/JPS5644069B2/ja not_active Expired
- 1974-01-08 NL NL7400233A patent/NL7400233A/xx not_active Application Discontinuation
-
1975
- 1975-04-18 FR FR7512159A patent/FR2274612A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE809437A (en) | 1974-07-08 |
| FR2274612B1 (en) | 1978-07-28 |
| JPS4995951A (en) | 1974-09-11 |
| JPS5644069B2 (en) | 1981-10-16 |
| FR2274612A1 (en) | 1976-01-09 |
| DE2365205A1 (en) | 1974-07-11 |
| FR2221132B1 (en) | 1977-06-17 |
| FR2221132A1 (en) | 1974-10-11 |
| NL7400233A (en) | 1974-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |