WO2003037857A3 - Improvements relating to prostaglandins and their analogues - Google Patents
Improvements relating to prostaglandins and their analogues Download PDFInfo
- Publication number
- WO2003037857A3 WO2003037857A3 PCT/GB2002/004922 GB0204922W WO03037857A3 WO 2003037857 A3 WO2003037857 A3 WO 2003037857A3 GB 0204922 W GB0204922 W GB 0204922W WO 03037857 A3 WO03037857 A3 WO 03037857A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- double bond
- analogues
- isopropyl
- dihydro
- prostaglandin
- Prior art date
Links
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 150000003180 prostaglandins Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- -1 prostaglandin C-1 ester Chemical class 0.000 abstract 3
- 239000002815 homogeneous catalyst Substances 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 229910052703 rhodium Inorganic materials 0.000 abstract 2
- 239000010948 rhodium Substances 0.000 abstract 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- 101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 abstract 1
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 abstract 1
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 abstract 1
- 101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052741 iridium Inorganic materials 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 1
- 229960001160 latanoprost Drugs 0.000 abstract 1
- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 abstract 1
- 150000003160 prostaglandin C1 derivatives Chemical class 0.000 abstract 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 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
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 abstract 1
- 229960002368 travoprost Drugs 0.000 abstract 1
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 abstract 1
Classifications
-
- 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
Abstract
Selective reduction of the 13, 14-double bond (in the presence of the 5, 6-double bond and unprotected hydroxyl groups) of certain prostaglandin C-1 esters, particularly PGA2, PGD2, PGE2, PGF2α and their analogues, can be achieved directly by use of homogeneous catalysts that co-ordinate with the 15-hydroxyl group and selectively deliver up hydrogen to the 13, 14-double bond to give the dihydro analogue (4) of the original prostaglandin C-1 ester (3) (3a) and (4a) R1 = n-butyl and R2 = methyl; (3b) and (4b) R1 = benzyl and R2 = isopropyl: Latanoprost; (3c) and (4c) R1 = m-trifluoromethylphenoxy and R2 = isopropyl: 13, 14-Dihydro Travoprost. R1 may be a substituted or unsubstituted alkyl, arylalkyl or aryloxy group, and R2 may be an alkyl group, preferably a C¿1?-C3 lower alkyl group. Such homogeneous catalysts include Wilkinson's rhodium catalyst, Crabtree's iridium catalyst and Evan's rhodium catalyst.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0126076.9 | 2001-10-31 | ||
| GB0126076A GB0126076D0 (en) | 2001-10-31 | 2001-10-31 | Improvements relating to prostaglandins and their analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2003037857A2 WO2003037857A2 (en) | 2003-05-08 |
| WO2003037857A3 true WO2003037857A3 (en) | 2003-09-12 |
Family
ID=9924829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2002/004922 WO2003037857A2 (en) | 2001-10-31 | 2002-10-31 | Improvements relating to prostaglandins and their analogues |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB0126076D0 (en) |
| WO (1) | WO2003037857A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL212658B1 (en) * | 2005-04-18 | 2012-11-30 | Inst Farmaceutyczny | Method for obtaining the derivatives of 13,14-dihydro-PGF₂α |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992002496A1 (en) * | 1990-08-08 | 1992-02-20 | Kabi Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
| WO2001087816A1 (en) * | 2000-05-15 | 2001-11-22 | Pharmacia & Upjohn Company | Process and intermediates to prepare latanoprost |
| WO2003037353A1 (en) * | 2001-10-31 | 2003-05-08 | Johnson Matthey Public Limited Company | Improvements relating to prostaglandins and their analogues |
-
2001
- 2001-10-31 GB GB0126076A patent/GB0126076D0/en not_active Ceased
-
2002
- 2002-10-31 WO PCT/GB2002/004922 patent/WO2003037857A2/en not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992002496A1 (en) * | 1990-08-08 | 1992-02-20 | Kabi Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
| WO2001087816A1 (en) * | 2000-05-15 | 2001-11-22 | Pharmacia & Upjohn Company | Process and intermediates to prepare latanoprost |
| WO2003037353A1 (en) * | 2001-10-31 | 2003-05-08 | Johnson Matthey Public Limited Company | Improvements relating to prostaglandins and their analogues |
Non-Patent Citations (2)
| Title |
|---|
| BOULTON, LEE T. ET AL: "Synthesis of the Potent Antiglaucoma Agent, Travoprost", ORGANIC PROCESS RESEARCH & DEVELOPMENT (2002), 6(2), 138-145 CODEN: OPRDFK; ISSN: 1083-6160, 2002, XP002246796 * |
| SELLIAH, ROBERT ET AL: "Synthesis of [phenyl-2-3H]- travoprost : isopropyl ester prodrug of a selective prostaglandin FP receptor agonist", JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS (2001), 44(3), 173-183 CODEN: JLCRD4; ISSN: 0362-4803, 1 March 2001 (2001-03-01), XP008019001 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0126076D0 (en) | 2001-12-19 |
| WO2003037857A2 (en) | 2003-05-08 |
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