IL40970A - Prostaglandin f2alpha 15-esters - Google Patents
Prostaglandin f2alpha 15-estersInfo
- Publication number
- IL40970A IL40970A IL40970A IL4097072A IL40970A IL 40970 A IL40970 A IL 40970A IL 40970 A IL40970 A IL 40970A IL 4097072 A IL4097072 A IL 4097072A IL 40970 A IL40970 A IL 40970A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- alkyl
- halogen
- formula
- cis
- Prior art date
Links
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 title 1
- PXGPLTODNUVGFL-UHFFFAOYSA-N prostaglandin F2alpha Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O PXGPLTODNUVGFL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 2
- 230000003287 optical effect Effects 0.000 claims abstract 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005620 boronic acid group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- -1 CF 3 Inorganic materials 0.000 abstract 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 3
- 150000003180 prostaglandins Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000005621 boronate group Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000011200 topical administration Methods 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (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
1389069 Prostaglandins UPJOHN CO 28 Nov 1972 [30 Dec 1971] 54948/72 Heading C2C Optical active prostaglandins of the formula or racemates thereof, wherein (a) X is trans- CH = CH- or -CH 2 CH 2 -, and Y and Z are both -CH 2 CH 2 , or (b) X is trans-CH=CH-, Y is cis-CH=CH, and Z is -CH 2 CH 2 - or cis-CH=CH-; M is or wherein R<SP>2</SP> is H, C 1-17 alkyl, C 1-12 alkyl substituted one to three times by halogen, phenyl, phenoxy or C 3-7 cycloalkyl, phenyl, phenyl substituted one to five times by halogen, CF 3 , NO 2 , phenyl or C 1-8 alkyl, or naphthyl; and R 2 is H or C 1-8 alkyl, and salts thereof, the compounds being novel provided that R 1 is not CH 3 when R 2 is CH 3 , X is trans-CH=CH-, Y is cis- CH = CH- and 2 is -CH 2 CH 2 -, are prepared by hydrolysing a boronates of the formula wherein R 3 is C 1-12 alkyl optionally substituted one to three times by halogen, NH 2 , phenyl trimethylsilyl or C 1-4 alkoxy, phenyl optionally substituted one to five times by halogen, NO 2 , OH, C 1-4 alkoxy, -COOH, NH 2 , phenyl or C 1-8 alkyl, naphthyl or phenanthoyl, and, if desired or necessary, esterifying the resulting product. Pharmaceutical compositions, suitable for oral, parenteral, rectal, vaginal, sublingual, or topical administration, contain the above novel prostaglandins and pharmaceutically acceptable carriers. The compounds possess similar activities to the corresponding PGFα compounds.
[GB1389069A]
Claims (1)
1. IS A c co r 1 a i toms a compound according to claim PGF20 a compound according to c 1 a i m Z are as defined by reacting an optically compound of the formula 2906 or a c compound of that formula and the mirror image wherein and are as defined with a boronic acid of the formula wherein R3 is as preparing an optical ly active acylated boronate of the or a racemi c compound of that formula and the mirror image wherein and R3 are as defined above by reacting said boronate of step with a ng and hydrolyzing the boronic acid moiety from said acylated boronate of step 1 A compound according to wherein X is 0 Y is Z is M is II H wherein is a ky of one to 17 carbon inclusi and i s a compound according to according to claim a compound according to claim a compound according to claim Box Attorneys for Applicant insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21447271A | 1971-12-30 | 1971-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40970A0 IL40970A0 (en) | 1973-01-30 |
| IL40970A true IL40970A (en) | 1976-03-31 |
Family
ID=22799199
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL47174A IL47174A (en) | 1971-12-30 | 1972-11-30 | Pgf2alpha-9,11-cyclic boronates and process for their preparation |
| IL40970A IL40970A (en) | 1971-12-30 | 1972-11-30 | Prostaglandin f2alpha 15-esters |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL47174A IL47174A (en) | 1971-12-30 | 1972-11-30 | Pgf2alpha-9,11-cyclic boronates and process for their preparation |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4875548A (en) |
| BE (1) | BE793534A (en) |
| CA (1) | CA978940A (en) |
| CH (1) | CH583191A5 (en) |
| DE (1) | DE2262608A1 (en) |
| DK (1) | DK135212B (en) |
| ES (1) | ES410104A1 (en) |
| FR (1) | FR2166194B1 (en) |
| GB (2) | GB1389070A (en) |
| HU (1) | HU166953B (en) |
| IL (2) | IL47174A (en) |
| NL (1) | NL7217579A (en) |
| SE (1) | SE411899B (en) |
| ZA (1) | ZA728737B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001306A (en) * | 1971-12-30 | 1977-01-04 | The Upjohn Company | Prostaglandin F.sub.α 15-monoacrylates |
| CA2014038A1 (en) * | 1989-05-25 | 1990-11-25 | Charles Gluchowski | Intraocular pressure reducing 15-acyl prostaglandins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2166721A1 (en) * | 1970-09-11 | 1975-05-15 | Upjohn Co | PROSTANIC ACID DERIVATIVES AND THEIR PRODUCTION |
-
0
- BE BE793534D patent/BE793534A/en unknown
-
1972
- 1972-11-24 CA CA157,431A patent/CA978940A/en not_active Expired
- 1972-11-28 GB GB3201074A patent/GB1389070A/en not_active Expired
- 1972-11-28 GB GB5494872A patent/GB1389069A/en not_active Expired
- 1972-11-30 IL IL47174A patent/IL47174A/en unknown
- 1972-11-30 IL IL40970A patent/IL40970A/en unknown
- 1972-12-11 JP JP47123522A patent/JPS4875548A/ja active Pending
- 1972-12-11 ZA ZA728737A patent/ZA728737B/en unknown
- 1972-12-13 CH CH1813872A patent/CH583191A5/xx not_active IP Right Cessation
- 1972-12-21 DE DE2262608A patent/DE2262608A1/en active Pending
- 1972-12-22 NL NL7217579A patent/NL7217579A/xx not_active Application Discontinuation
- 1972-12-27 SE SE7216988A patent/SE411899B/en unknown
- 1972-12-27 HU HUUO84A patent/HU166953B/hu unknown
- 1972-12-28 ES ES410104A patent/ES410104A1/en not_active Expired
- 1972-12-29 DK DK655272AA patent/DK135212B/en unknown
- 1972-12-29 FR FR7246986A patent/FR2166194B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2166194A1 (en) | 1973-08-10 |
| ES410104A1 (en) | 1975-12-16 |
| CA978940A (en) | 1975-12-02 |
| ZA728737B (en) | 1973-09-26 |
| SE411899B (en) | 1980-02-11 |
| BE793534A (en) | 1973-06-29 |
| FR2166194B1 (en) | 1977-01-28 |
| DE2262608A1 (en) | 1973-07-12 |
| GB1389070A (en) | 1975-04-03 |
| NL7217579A (en) | 1973-07-03 |
| DK135212B (en) | 1977-03-21 |
| GB1389069A (en) | 1975-04-03 |
| DK135212C (en) | 1977-09-05 |
| JPS4875548A (en) | 1973-10-11 |
| HU166953B (en) | 1975-06-28 |
| IL47174A (en) | 1976-03-31 |
| CH583191A5 (en) | 1976-12-31 |
| IL40970A0 (en) | 1973-01-30 |
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