ES452264A1 - Prostaglandin derivatives - Google Patents
Prostaglandin derivativesInfo
- Publication number
- ES452264A1 ES452264A1 ES452264A ES452264A ES452264A1 ES 452264 A1 ES452264 A1 ES 452264A1 ES 452264 A ES452264 A ES 452264A ES 452264 A ES452264 A ES 452264A ES 452264 A1 ES452264 A1 ES 452264A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- hydrogen
- alkyl
- group
- hydroxy
- 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
- 150000003180 prostaglandins Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- -1 trialkylsilyl ether Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Procedure for the preparation of racemic and optically active compounds of the formula I **(See formula)** in which J stands for hydrogen or hydroxy; K stands for carbonyl or carbinol; L is ethylene or vinylene; Q is hydrogen, a non-toxic and pharmaceutically acceptable cation or lower alkyl; one of the symbols R1, R2 and R3 is C1-6 alkyl and the other two are hydrogen; both J and the hydroxy group can be in alpha or beta position, characterized in that it comprises reacting a compound of formula II **(See formula)** (where Q1 is alkyl; L has the same meaning as indicated above and J is hydrogen or hydroxy, which is protected in the form of an acetal or a trialkylsilyl ether) with a nucleophilic cuprate reactant of formula III **(See formula)** (Wherein R1, R2 and R3 are as indicated above; Rx is a suitable group substantially nontransferable in the enon system under the reaction conditions used, preferably an aliphatic alkyne, triphenoxide, tertiary butoxide, phenoxide, or a group of the formula IV **(See formula)** where R'means a group that can be easily cleaved under mild acidic or alkaline conditions), converting, if desired, an ester of the formula I thus obtained -in which Q is alkyl- into the corresponding free acid -in which Q it is hydrogen- or a non-toxic and pharmaceutically acceptable salt thereof and, if desired, reducing a compound of formula I - where K is carbonyl - to the corresponding compound of formula I - where K is carbinol. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75CI1612A HU174274B (en) | 1975-09-26 | 1975-09-26 | Process for producing substituted cyclohexylidene-prostaglandin analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES452264A1 true ES452264A1 (en) | 1977-11-01 |
Family
ID=10994581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES452264A Expired ES452264A1 (en) | 1975-09-26 | 1976-09-23 | Prostaglandin derivatives |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5257151A (en) |
| AR (1) | AR213292A1 (en) |
| AT (1) | AT353990B (en) |
| AU (1) | AU1806476A (en) |
| BE (1) | BE846551A (en) |
| CS (1) | CS189789B2 (en) |
| DD (1) | DD127163A5 (en) |
| DE (1) | DE2642558A1 (en) |
| DK (1) | DK426676A (en) |
| ES (1) | ES452264A1 (en) |
| FI (1) | FI762738A (en) |
| FR (1) | FR2325367A1 (en) |
| GB (1) | GB1515789A (en) |
| GR (1) | GR61671B (en) |
| HU (1) | HU174274B (en) |
| IL (1) | IL50532A0 (en) |
| NL (1) | NL7610635A (en) |
| NO (1) | NO763278L (en) |
| PL (1) | PL105784B1 (en) |
| SE (1) | SE7610513L (en) |
| SU (1) | SU701532A3 (en) |
-
1975
- 1975-09-26 HU HU75CI1612A patent/HU174274B/en unknown
-
1976
- 1976-09-22 DK DK426676A patent/DK426676A/en unknown
- 1976-09-22 AT AT701276A patent/AT353990B/en not_active IP Right Cessation
- 1976-09-22 IL IL50532A patent/IL50532A0/en unknown
- 1976-09-22 DE DE19762642558 patent/DE2642558A1/en active Pending
- 1976-09-22 SE SE7610513A patent/SE7610513L/en unknown
- 1976-09-23 GR GR51758A patent/GR61671B/en unknown
- 1976-09-23 CS CS766176A patent/CS189789B2/en unknown
- 1976-09-23 ES ES452264A patent/ES452264A1/en not_active Expired
- 1976-09-23 AU AU18064/76A patent/AU1806476A/en not_active Expired
- 1976-09-24 BE BE170904A patent/BE846551A/en unknown
- 1976-09-24 FI FI762738A patent/FI762738A/fi not_active Application Discontinuation
- 1976-09-24 DD DD194976A patent/DD127163A5/xx unknown
- 1976-09-24 FR FR7628841A patent/FR2325367A1/en active Granted
- 1976-09-24 NL NL7610635A patent/NL7610635A/en not_active Application Discontinuation
- 1976-09-24 SU SU762405549A patent/SU701532A3/en active
- 1976-09-24 NO NO763278A patent/NO763278L/no unknown
- 1976-09-24 GB GB39831/76A patent/GB1515789A/en not_active Expired
- 1976-09-25 PL PL1976192650A patent/PL105784B1/en unknown
- 1976-09-27 AR AR264859A patent/AR213292A1/en active
- 1976-09-27 JP JP51114838A patent/JPS5257151A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU1806476A (en) | 1978-04-06 |
| DE2642558A1 (en) | 1977-04-07 |
| DK426676A (en) | 1977-03-27 |
| AR213292A1 (en) | 1979-01-15 |
| CS189789B2 (en) | 1979-04-30 |
| SE7610513L (en) | 1977-03-27 |
| NO763278L (en) | 1977-03-29 |
| HU174274B (en) | 1979-12-28 |
| FR2325367A1 (en) | 1977-04-22 |
| PL105784B1 (en) | 1979-10-31 |
| NL7610635A (en) | 1977-03-29 |
| DD127163A5 (en) | 1977-09-07 |
| JPS5257151A (en) | 1977-05-11 |
| GR61671B (en) | 1978-12-05 |
| FI762738A (en) | 1977-03-27 |
| SU701532A3 (en) | 1979-11-30 |
| GB1515789A (en) | 1978-06-28 |
| IL50532A0 (en) | 1976-11-30 |
| BE846551A (en) | 1977-01-17 |
| ATA701276A (en) | 1979-05-15 |
| AT353990B (en) | 1979-12-10 |
| FR2325367B1 (en) | 1979-03-23 |
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