IL47174A - Pgf2alpha-9,11-cyclic boronates and process for their preparation - Google Patents
Pgf2alpha-9,11-cyclic boronates and process for their preparationInfo
- Publication number
- IL47174A IL47174A IL47174A IL4717472A IL47174A IL 47174 A IL47174 A IL 47174A IL 47174 A IL47174 A IL 47174A IL 4717472 A IL4717472 A IL 4717472A IL 47174 A IL47174 A IL 47174A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- alkyl
- formula
- cis
- trans
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- -1 CF 3 Inorganic materials 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 2
- QPKFVRWIISEVCW-UHFFFAOYSA-N 1-butane boronic acid Chemical compound CCCCB(O)O QPKFVRWIISEVCW-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 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
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000003287 optical effect 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
- 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 (9)
1. · A process for prejarlng a 9*ll-cyclic boronate of the formula: or a racemlc compound of that formula and the mirror Image thereof, wherein X Is trans-CH=CH-, Y is cis-CH=CH-, and Z Is -CI^CHg-wherein is hydrogen or alkyl and the pharmacologically acceptable salts thereof when R-^ is hydrogen; and wherein R^ is alkyl of one to 12 carbon atoms or phenyl which comprises reacting a compound of the formula: wherein X, Y, Z and R^ are as defined above, with a boronic acid of the formula RJB(OH) , wherein R¾ is as defined above,
2. A process according to claim 1, wherein the boronic acid is n-butaneboronic acid or benzeneboronic acid.
3. A process according to claim 1 or 2, wherein the mole ratio of boronic acid to PGF2 compound is from 1 to 10*
4. A process according to claim 3* wherein the ratio is about t o.
5. A process according to any of claims 1 to 4, wherein the process is carried out in pyridine as reaction medium.
6. Process for the production of 9,11-cyclic boronates defined in claim 1, substantially as hereinbefore described and with reference to the examples
7. A 9,11-cyclic boronate of the formula or a racemic compound of that formula and the mirror image thereof, wherein- X is trans-CH=CH-, Y is cis-CH=CH-, and Z is -CHgCHg- wherein R1 is hydrogen or alkyl and the pharmacologically acceptable salts thereof when R is hydrogen; and wherein R^ is of 0116 to 12 carbon atoms or phenyl.
8. A boronate according to claim 7, wherein ^ is n-butyl or phenyl.
9. 9,11-Cyclic boronates defined in claim 7* substantially
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21447271A | 1971-12-30 | 1971-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL47174A true IL47174A (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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40970A IL40970A (en) | 1971-12-30 | 1972-11-30 | Prostaglandin f2alpha 15-esters |
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 |
|---|---|---|---|---|
| DE2145125A1 (en) * | 1970-09-11 | 1972-04-06 | The Upjohn Co , Kalamazoo, Mich (V St A) | Prostanoic 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 ZA ZA728737A patent/ZA728737B/en unknown
- 1972-12-11 JP JP47123522A patent/JPS4875548A/ja active Pending
- 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 HU HUUO84A patent/HU166953B/hu unknown
- 1972-12-27 SE SE7216988A patent/SE411899B/en unknown
- 1972-12-28 ES ES410104A patent/ES410104A1/en not_active Expired
- 1972-12-29 FR FR7246986A patent/FR2166194B1/fr not_active Expired
- 1972-12-29 DK DK655272AA patent/DK135212B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE793534A (en) | 1973-06-29 |
| CH583191A5 (en) | 1976-12-31 |
| FR2166194A1 (en) | 1973-08-10 |
| NL7217579A (en) | 1973-07-03 |
| HU166953B (en) | 1975-06-28 |
| DK135212B (en) | 1977-03-21 |
| CA978940A (en) | 1975-12-02 |
| IL40970A0 (en) | 1973-01-30 |
| DE2262608A1 (en) | 1973-07-12 |
| IL40970A (en) | 1976-03-31 |
| FR2166194B1 (en) | 1977-01-28 |
| DK135212C (en) | 1977-09-05 |
| GB1389070A (en) | 1975-04-03 |
| ZA728737B (en) | 1973-09-26 |
| SE411899B (en) | 1980-02-11 |
| JPS4875548A (en) | 1973-10-11 |
| ES410104A1 (en) | 1975-12-16 |
| GB1389069A (en) | 1975-04-03 |
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