CA2067341A1 - Methode de synthese des derives de la prostaglandine - Google Patents
Methode de synthese des derives de la prostaglandineInfo
- Publication number
- CA2067341A1 CA2067341A1 CA2067341A CA2067341A CA2067341A1 CA 2067341 A1 CA2067341 A1 CA 2067341A1 CA 2067341 A CA2067341 A CA 2067341A CA 2067341 A CA2067341 A CA 2067341A CA 2067341 A1 CA2067341 A1 CA 2067341A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- synthesis
- hydroxyl
- halogen
- hydrogen
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000003180 prostaglandins Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 238000006392 deoxygenation reaction Methods 0.000 abstract 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 abstract 1
- 229960002986 dinoprostone Drugs 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Méthode de préparation d'analogues 13,14-dihydro-17-phénylés de la PGF2a ou de la PGE2 comprenant une étape d'hydrogénation de la double liaison d'un composé intermédiaire (I) sans désoxygénation de l'alcool allylique de façon à obtenir les composés intermédiaires (II et III) où R représente un hydrogène ou au moins un halogène, un hydroxyle, un cyanure, un alkyle (de préférence à 1-4 atomes de carbone), un hydroxyalkyle, un trifluorométhyle ou les substituants aromatiques ou hétéroaromatiques, R1 et R2, sur le noyau aromatique sont tous deux un hydrogène, un alkyle (de préférence à 1-4 atomes de carbone), un hydroxyle, un halogène ou un hydroxyalkyle, R3 est un O-alkyle ou un N-alkyle et P est un groupe de protection.0
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9002596-6 | 1990-08-08 | ||
| SE9002596A SE9002596D0 (sv) | 1990-08-08 | 1990-08-08 | A method for synthesis of prostaglandin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2067341A1 true CA2067341A1 (fr) | 1992-02-09 |
| CA2067341C CA2067341C (fr) | 1997-09-30 |
Family
ID=20380110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002067341A Expired - Fee Related CA2067341C (fr) | 1990-08-08 | 1991-08-08 | Methode de synthese des derives de la prostaglandine |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0495069B1 (fr) |
| JP (1) | JP2670521B2 (fr) |
| AT (1) | ATE133162T1 (fr) |
| BG (1) | BG61143B1 (fr) |
| CA (1) | CA2067341C (fr) |
| DE (1) | DE69116541T2 (fr) |
| HU (1) | HUT62874A (fr) |
| RO (1) | RO109332B1 (fr) |
| RU (1) | RU2073668C1 (fr) |
| SE (1) | SE9002596D0 (fr) |
| WO (1) | WO1992002496A1 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223537A (en) * | 1991-07-23 | 1993-06-29 | Kabi Pharmacia Ab | Method and composition for treatment of gastric and duodenal disorders |
| US5516796A (en) * | 1994-03-24 | 1996-05-14 | Kabi Pharmacia Ab | Thioprostaglandins and -prostaglandin-like compounds and therapeutic uses thereof |
| WO1998021180A1 (fr) * | 1995-06-07 | 1998-05-22 | Alcon Laboratories, Inc. | Prostaglandines aryle ou heteroaryle a conformation rigide utilisees dans le traitement des glaucomes |
| GB0112699D0 (en) | 2001-05-24 | 2001-07-18 | Resolution Chemicals Ltd | Process for the preparation of prostglandins and analogues thereof |
| GB0126076D0 (en) * | 2001-10-31 | 2001-12-19 | Cascade Biochem Ltd | Improvements relating to prostaglandins and their analogues |
| JP2008037782A (ja) * | 2006-08-04 | 2008-02-21 | Daiichi Fine Chemical Co Ltd | プロスタグランジン誘導体の製造方法 |
| US7642370B2 (en) | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| CA2777290C (fr) | 2009-10-16 | 2016-06-28 | Cayman Chemical Company, Incorporated | Procede de preparation de prostaglandines de la serie f |
| PL2723714T3 (pl) * | 2011-06-02 | 2018-02-28 | CHINOIN Zrt. | Nowe sposoby otrzymywania amidów prostaglandyn |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES416865A1 (es) * | 1972-07-13 | 1976-03-01 | Pfizer | Procedimiento para preparar w-pentanorprostaglandinas sus- tituidas en la posicion 15. |
| US3962312A (en) * | 1972-09-21 | 1976-06-08 | Ono Pharmaceutical Company | 9,11,15-Trihydroxy prost-5-enoic acid analogues |
-
1990
- 1990-08-08 SE SE9002596A patent/SE9002596D0/xx unknown
-
1991
- 1991-08-08 JP JP3513618A patent/JP2670521B2/ja not_active Expired - Fee Related
- 1991-08-08 AT AT91914853T patent/ATE133162T1/de not_active IP Right Cessation
- 1991-08-08 EP EP91914853A patent/EP0495069B1/fr not_active Expired - Lifetime
- 1991-08-08 RU SU915011925A patent/RU2073668C1/ru not_active IP Right Cessation
- 1991-08-08 WO PCT/SE1991/000525 patent/WO1992002496A1/fr not_active Ceased
- 1991-08-08 HU HU921194A patent/HUT62874A/hu unknown
- 1991-08-08 DE DE69116541T patent/DE69116541T2/de not_active Expired - Fee Related
- 1991-08-08 RO RO92-200479A patent/RO109332B1/ro unknown
- 1991-08-08 CA CA002067341A patent/CA2067341C/fr not_active Expired - Fee Related
-
1992
- 1992-04-07 BG BG96194A patent/BG61143B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2073668C1 (ru) | 1997-02-20 |
| WO1992002496A1 (fr) | 1992-02-20 |
| BG61143B1 (bg) | 1996-12-31 |
| HUT62874A (en) | 1993-06-28 |
| JPH05502043A (ja) | 1993-04-15 |
| CA2067341C (fr) | 1997-09-30 |
| RO109332B1 (ro) | 1995-01-30 |
| SE9002596D0 (sv) | 1990-08-08 |
| AU645129B2 (en) | 1994-01-06 |
| JP2670521B2 (ja) | 1997-10-29 |
| DE69116541D1 (en) | 1996-02-29 |
| EP0495069A1 (fr) | 1992-07-22 |
| ATE133162T1 (de) | 1996-02-15 |
| AU8391591A (en) | 1992-03-02 |
| EP0495069B1 (fr) | 1996-01-17 |
| DE69116541T2 (de) | 1996-09-19 |
| BG96194A (bg) | 1993-12-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |