FR2013927A1 - Preparation of prostaglandin analogues with more - specific biological activity than natural prostaglandins - Google Patents
Preparation of prostaglandin analogues with more - specific biological activity than natural prostaglandinsInfo
- Publication number
- FR2013927A1 FR2013927A1 FR6925804A FR6925804A FR2013927A1 FR 2013927 A1 FR2013927 A1 FR 2013927A1 FR 6925804 A FR6925804 A FR 6925804A FR 6925804 A FR6925804 A FR 6925804A FR 2013927 A1 FR2013927 A1 FR 2013927A1
- Authority
- FR
- France
- Prior art keywords
- prostaglandin
- natural prostaglandins
- preparation
- biological activity
- difluorobutyl
- 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
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 3
- 150000003180 prostaglandins Chemical class 0.000 title abstract 3
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title abstract 2
- 230000004071 biological effect Effects 0.000 title 1
- -1 3,3- difluorobutyl Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 abstract 1
- BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000008512 biological response Effects 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
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Prostaglandin analogues (II) are new compds. prepared by reacting water at 0-60 C with disulphenic esters of formula I, which may have the exo- or endv configuration. (which n is 1-8; a is 0-4; R15 is C1-4 alkyl or -CH2CCl3: Y = i-butyl, t-butyl, 3,3- difluorobutyl, 4,4-difluorobutyl, or 4,4,4-triflurorbutyl; is approx. indicates that the -(CH2)n-COOR15 group is in alpha- or beta-configuration relative to the ring; R6 is C1-5 alkyl) Advantages/uses:- the cpds. II and III and their derivatives are analogous to prostaglandin E, prostaglandin F and prostaglandin A in their bilogical activity, but are much more specific in action. As the present compounds have a narrower biological spectrum, their use is generally attended by a lesser degree of undesired side actions than for the natural prostaglandins. In addition, some of the synthetic compounds show a higher biological response than the natural prostaglandins in a specific area.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74815868A | 1968-07-29 | 1968-07-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2013927A1 true FR2013927A1 (en) | 1970-04-10 |
| FR2013927B1 FR2013927B1 (en) | 1973-01-12 |
Family
ID=25008268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR6925804A Granted FR2013927A1 (en) | 1968-07-29 | 1969-07-28 | Preparation of prostaglandin analogues with more - specific biological activity than natural prostaglandins |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE736726A (en) |
| CH (1) | CH532009A (en) |
| DE (1) | DE1937908A1 (en) |
| ES (2) | ES369990A1 (en) |
| FR (1) | FR2013927A1 (en) |
| IL (1) | IL32552A (en) |
| NL (1) | NL6911476A (en) |
| PL (1) | PL84082B1 (en) |
| SU (1) | SU385430A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2183041A1 (en) * | 1972-04-27 | 1973-12-14 | Upjohn Co |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1533808A (en) * | 1966-08-09 | 1968-07-19 | New compounds similar to prostaglandin e1 and prostaglandin f1 and their manufacturing process |
-
1969
- 1969-07-04 IL IL32552A patent/IL32552A/en unknown
- 1969-07-25 NL NL6911476A patent/NL6911476A/xx unknown
- 1969-07-25 DE DE19691937908 patent/DE1937908A1/en active Pending
- 1969-07-28 FR FR6925804A patent/FR2013927A1/en active Granted
- 1969-07-28 CH CH1149769A patent/CH532009A/en not_active IP Right Cessation
- 1969-07-28 PL PL1969135099A patent/PL84082B1/en unknown
- 1969-07-29 ES ES369990A patent/ES369990A1/en not_active Expired
- 1969-07-29 BE BE736726A patent/BE736726A/en unknown
- 1969-07-29 SU SU1353823A patent/SU385430A3/ru active
-
1971
- 1971-08-31 ES ES394672A patent/ES394672A1/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1533808A (en) * | 1966-08-09 | 1968-07-19 | New compounds similar to prostaglandin e1 and prostaglandin f1 and their manufacturing process |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL COMMUNICATIONS '69 D6 PAGES 304-305.) * |
| JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 1968 PAGES 5895-6. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2183041A1 (en) * | 1972-04-27 | 1973-12-14 | Upjohn Co |
Also Published As
| Publication number | Publication date |
|---|---|
| CH532009A (en) | 1972-12-31 |
| ES394672A1 (en) | 1974-02-16 |
| IL32552A0 (en) | 1969-09-25 |
| FR2013927B1 (en) | 1973-01-12 |
| ES369990A1 (en) | 1971-12-16 |
| DE1937908A1 (en) | 1970-07-02 |
| NL6911476A (en) | 1970-02-02 |
| PL84082B1 (en) | 1976-02-28 |
| BE736726A (en) | 1970-01-29 |
| IL32552A (en) | 1975-07-28 |
| SU385430A3 (en) | 1973-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |