GB1388443A - Selective reduction of 9,15-dioxoprostanoic acids - Google Patents
Selective reduction of 9,15-dioxoprostanoic acidsInfo
- Publication number
- GB1388443A GB1388443A GB2635172A GB2635172A GB1388443A GB 1388443 A GB1388443 A GB 1388443A GB 2635172 A GB2635172 A GB 2635172A GB 2635172 A GB2635172 A GB 2635172A GB 1388443 A GB1388443 A GB 1388443A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- oxo
- trans
- alicyclic
- groups
- 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
- 239000002253 acid Substances 0.000 title abstract 10
- 150000007513 acids Chemical class 0.000 title abstract 6
- 125000002723 alicyclic group Chemical group 0.000 abstract 4
- 125000004043 oxo group Chemical group O=* 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- -1 cyanoborohydrides Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- NGKQFRQIMBARPL-UHFFFAOYSA-N 7-(2-formyl-3-hydroxy-5-oxocyclopenten-1-yl)heptanoic acid Chemical compound OC1CC(=O)C(CCCCCCC(O)=O)=C1C=O NGKQFRQIMBARPL-UHFFFAOYSA-N 0.000 abstract 1
- LUAZIMZKFFQYHF-UHFFFAOYSA-N 7-(2-formyl-3-hydroxy-5-oxocyclopentyl)heptanoic acid Chemical compound C(=O)C1C(C(CC1O)=O)CCCCCCC(=O)O LUAZIMZKFFQYHF-UHFFFAOYSA-N 0.000 abstract 1
- MFBVDSCXPZKARI-UHFFFAOYSA-N 7-[3-hydroxy-2-(hydroxymethyl)-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound OC1C(=C(C(C1)=O)CCCCCCC(=O)O)CO MFBVDSCXPZKARI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1388443 Prostanoic acids G D SEARLE & CO 6 June 1972 [11 June 1971] 26351/72 Heading C2C [Also in Division C3] The invention comprises the reduction, using metallic cyanoborohydrides, of protonoic acids containing aliphatic oxo groups and alicyclic oxo groups to prostanoic acids containing aliphatic hydroxy groups and alicyclic oxo groups or of prostanoic acids containing an alicyclic oxo group to prostanoic acids containing alicyclic hydroxy groups and the novel compound, 3 - hydroxy - 2 - hydroxymethyl - 5 - oxo - 1- cyclopentene - 1 - heptanoic acid, which is obtained by reducing 2-formyl-3-hydroxy-5- oxo-1-cyclopentene-1-heptanoic acid with metallic cyanoborohydrides. The following starting materials are prepared: 2 - formyl - 3 - hydroxy - 5 - oxocyclopentaneheptanoic acid, dl-11α (and 11#)-hydroxy- 9,15 - dioxoprost - trans - 13 - enoic acid, dl- 9,15 - dioxoprosta - 10, trans - 13 - enoic acid, dl - 11α - hydroxy - 9,15 - dioxo - 12 - epiprost - trans - 13 - enoic acid and 11 - hydroxy- 14 - methyl - 9,15 - dioxo - prosta - 8(12), trans- 13-enoic acid. Reference has been directed by the Comptroller to Specifications 1,097,533, 1,120,243, 1,198,071, 1,260,828 and 1,292,661.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15241471A | 1971-06-11 | 1971-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1388443A true GB1388443A (en) | 1975-03-26 |
Family
ID=22542818
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2119974A Expired GB1384865A (en) | 1971-06-11 | 1972-06-06 | Stereospecific reduction of 9,15-dioxo prostanglandins |
| GB2635172A Expired GB1388443A (en) | 1971-06-11 | 1972-06-06 | Selective reduction of 9,15-dioxoprostanoic acids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2119974A Expired GB1384865A (en) | 1971-06-11 | 1972-06-06 | Stereospecific reduction of 9,15-dioxo prostanglandins |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA967565A (en) |
| DE (1) | DE2228154B2 (en) |
| FR (2) | FR2140644B1 (en) |
| GB (2) | GB1384865A (en) |
| NL (1) | NL7207970A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30287E (en) * | 1974-03-26 | 1980-05-27 | Gist-Brocades N.V. | 19 Hydroxy prostaglandins |
| US8455547B2 (en) * | 2008-02-05 | 2013-06-04 | Allergan, Inc. | Substituted cyclopentanes having prostaglandin activity |
-
1972
- 1972-06-06 GB GB2119974A patent/GB1384865A/en not_active Expired
- 1972-06-06 GB GB2635172A patent/GB1388443A/en not_active Expired
- 1972-06-09 CA CA144,327A patent/CA967565A/en not_active Expired
- 1972-06-09 DE DE19722228154 patent/DE2228154B2/en not_active Withdrawn
- 1972-06-09 FR FR7220909A patent/FR2140644B1/fr not_active Expired
- 1972-06-12 NL NL7207970A patent/NL7207970A/xx not_active Application Discontinuation
-
1974
- 1974-05-02 FR FR7415288A patent/FR2225170B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2140644A1 (en) | 1973-01-19 |
| DE2228154A1 (en) | 1972-12-28 |
| GB1384865A (en) | 1975-02-26 |
| FR2225170A1 (en) | 1974-11-08 |
| FR2140644B1 (en) | 1976-04-16 |
| NL7207970A (en) | 1972-12-13 |
| FR2225170B1 (en) | 1979-05-25 |
| DE2228154B2 (en) | 1981-02-05 |
| CA967565A (en) | 1975-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |