GB1389070A - Boron-containing prostaglandin intermediates and their preparation - Google Patents
Boron-containing prostaglandin intermediates and their preparationInfo
- Publication number
- GB1389070A GB1389070A GB3201074A GB3201074A GB1389070A GB 1389070 A GB1389070 A GB 1389070A GB 3201074 A GB3201074 A GB 3201074A GB 3201074 A GB3201074 A GB 3201074A GB 1389070 A GB1389070 A GB 1389070A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- halogen
- formula
- optically active
- 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
- 229910052796 boron Inorganic materials 0.000 title abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000003180 prostaglandins Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- -1 Cyclic boron prostaglandin Chemical class 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000005621 boronate group Chemical class 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000005561 phenanthryl group Chemical group 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
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
1389070 Cyclic boron prostaglandin intermediate UPJOHN CO 28 Nov 1972 [30 Dec 1971] 32010/74 Divided out of 1389069 Heading C2B The invention comprises optically active compounds of the formula or racemates thereof, wherein (a) X is trans- -CH=CH- or -CH 2 CH 2 - andY and Z are both -CH 2 CH 2 -, or (b) X is Y is cis-CH=CH- and Z is -CH 2 CH 2 - or cis-CH=CH-; M being where R 2 is H; C 1-17 alkyl; C 1-12 alkyl substituted by 1-3 substitutents selected from one or more of halogen, phenyl, phenoxy or C 3-7 cycloalkyl; phenyl optionally substituted 1-5 times by one or more of halogen, -CF 3 , nitro, phenyl or C 1-8 alkyl; or naphthyl; R 1 being H or C 1-8 alkyl; and R 3 being C 1-12 alkyl optionally substituted 1-3 times by one or more of halogen, amino, phenyl, trimethylsilyl or C 1-4 alkoxy; phenyl optionally substituted 1-5 times by one or more of halogen, nitro, hydroxy, C 1-4 alkoxy, carboxy, amino, phenyl or C 1-8 alkyl; naphthyl; or phenanthryl; and also, when R 1 is hydrogen, the pharmacologically acceptable salts of such compounds. The compounds are prepared by (1) reacting an optically active compound of the formula or a racemate thereof, wherein G is with a boronic acid R 3 B(OH) 2 , usually in a non- hydroxylic solvent such as pyridine, acetonitrile, acetone or N,N-dimethyl-formamide and under anhydrous conditions, to produce an optically active boronate of formula or a racemate thereof and (ii) reacting this boronate with a carboxyacylating agent such as R 2 COX (X is Cl, Br or F), or (R 2 CO) 2 O, preferably in the presence of a tertiary amine such as pyridine or (C 2 H 5 ) 3 N and using a substantial excess of the carboxyacylating agent and, optionally, a diluent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21447271A | 1971-12-30 | 1971-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1389070A true GB1389070A (en) | 1975-04-03 |
Family
ID=22799199
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3201074A Expired GB1389070A (en) | 1971-12-30 | 1972-11-28 | Boron-containing prostaglandin intermediates and their preparation |
| GB5494872A Expired GB1389069A (en) | 1971-12-30 | 1972-11-28 | Prostaglandins and the preparation thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5494872A Expired GB1389069A (en) | 1971-12-30 | 1972-11-28 | Prostaglandins and the preparation thereof |
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 |
| 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 |
| IL47174A (en) | 1976-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1394732A (en) | Enamine compounds their manufacture and use | |
| GB1522686A (en) | 1-(bis-trifluoromethylphenyl)-2-oxo-pyrrolidine-4-carboxylic acid derivatives their production and their use as plantgrowth regulators and herbicides | |
| SE8202034L (en) | NEW CHEMICAL PROCEDURE FOR THE PREPARATION OF PROPIONITRIL DERIVATIVES | |
| GB1319479A (en) | Trichloroethylamides | |
| GB1389070A (en) | Boron-containing prostaglandin intermediates and their preparation | |
| GB1395802A (en) | Substituted benzamides and herbicidal uses thereof | |
| ES387834A1 (en) | Acid amides | |
| GB1244975A (en) | Benzodioxane derivatives | |
| ES403486A1 (en) | Procedure for the preparation of piperazine derivatives. (Machine-translation by Google Translate, not legally binding) | |
| GB1375660A (en) | ||
| GB1526038A (en) | 5-thiazole methane amine derivatives and salts thereof processes for preparing them and pharmaceutical compositions containing them | |
| ES435955A1 (en) | A procedure for obtaining a pirid derivative (3,4-d) pyridezine. (Machine-translation by Google Translate, not legally binding) | |
| ES285236A1 (en) | Procedure for the preparation of penicillins (Machine-translation by Google Translate, not legally binding) | |
| GB1507414A (en) | Hydantoin derivatives | |
| GB1509454A (en) | 2-amino-tetralins | |
| ES471872A1 (en) | Tetrahydro-s-triazine thiones, process for their preparation and acaricidal compositions containing them. | |
| SE415021B (en) | PROCEDURE FOR PREPARING 11BETA-HYDROXY-18-ALKYL-OSTRAN COMPOUNDS | |
| ES408184A1 (en) | 15-hydroxy vincamine | |
| GB1380016A (en) | Mannich bases a process for their preparation and their use in the production of polyurethanes | |
| GB1362337A (en) | Process for the preparation of 3- beta-dialkyl-aminoethyl - 4-alkyl -7-carboethoxymethoxycoumarins | |
| GB1364157A (en) | Process for the preparation of 2-/2-aminobenzoyl/ pyridines | |
| GB1232169A (en) | ||
| ES452398A1 (en) | A process for preparing 33aminoazetidinone | |
| GB1459162A (en) | 2-aryloxy-2-propen-1-one derivatives | |
| GB1361946A (en) | Prostaglandin synthesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |