GB1497829A - 11-deoxyprostaglandins - Google Patents
11-deoxyprostaglandinsInfo
- Publication number
- GB1497829A GB1497829A GB16429/75A GB1642975A GB1497829A GB 1497829 A GB1497829 A GB 1497829A GB 16429/75 A GB16429/75 A GB 16429/75A GB 1642975 A GB1642975 A GB 1642975A GB 1497829 A GB1497829 A GB 1497829A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- enyl
- trans
- dioxaspiro
- chlorophenoxy
- 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
- -1 hydroxymethylene Chemical group 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- IOMZRUBUCCWVBH-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C1=CC(Cl)=CC=C1OCC(=O)C=P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IOMZRUBUCCWVBH-UHFFFAOYSA-N 0.000 abstract 1
- TVICFYIGXQRSRN-UHFFFAOYSA-N 1-chloro-3-(4-chlorophenoxy)propan-2-one Chemical compound ClCC(=O)COC1=CC=C(Cl)C=C1 TVICFYIGXQRSRN-UHFFFAOYSA-N 0.000 abstract 1
- 229920000858 Cyclodextrin Polymers 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
- ZZVSJVZSZPERPY-UHFFFAOYSA-M [3-(4-chlorophenoxy)-2-oxopropyl]-triphenylphosphanium chloride Chemical compound [Cl-].O=C(C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)COC1=CC=C(C=C1)Cl ZZVSJVZSZPERPY-UHFFFAOYSA-M 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1497829 11-Deoxyprostaglandins MAY & BAKER Ltd 20 April 1976 [21 April 1975] 16429/75 Heading C2C [Also in Division C3] The invention comprises 11-deoxyprostaglandins of the formula wherein R<SP>1</SP> is H or C 1-15 alkyl; A is C 1-12 alkylene; Y is carbonyl or hydroxymethylene, n is 4, 5 or 6 and either (i) Z is a direct bond and R<SP>7</SP> is H or alkyl or an aryl or heteroaryl which may be substituted by one or more substituents selected from halogen atoms, alkyl, haloalkyl, alkenyl, alkoxy, alkenyloxy, alkoxycarbonyl, hydroxy, cyano, nitro, sulphamoyl, mono- or di-alkyl sulphamoyl, carbamoyl, mono- or dialkylcarbamoyl and dialkylamino, or else (ii) Z is O or S, and R<SP>2</SP> is alkyl or an aryl or heteroaryl group which may be substituted by one or more substitutents selected from halogen atom, alkyl, haloalkyl, alkenyl, alkoxy, alkenyloxy, alkoxycarbonyl, hydroxy, cyano, nitro, sulphamoyl, mono- or di-alkyl sulphomoyl, carbamoyl, mono- or di-alkylcarbamoyl, alkanoylamino and dialkylamino, and the vinylene groups in the side-chains are both in transconfiguration and cyclodextrin clathrates thereof and when R<SP>1</SP> is H, non-toxic salts thereof, and their preparation. The compounds of the above Formula I in which Y is hydroxymethylene are prepared by reducing the corresponding compounds in which Y is carbonyl, which are obtained by hydrolysing compounds of the Formula V wherein the symbols R<SP>4</SP> are identical alkyl groups or together form an ethylene linkage optionally substituted by one identical alkyl group on each carbon atom. The free acids may be obtained by the hydrolysis of the corresponding C 1-15 alkyl esters and the esters prepared by esterification of the appropriate acids. The following intermediates are also prepared: 6 - (7 - hydroxyheptyl) - 7 - (3 - oxooct - trans- 1 - enyl) - 1,4 - dioxaspiro[4,4]nonane; 6 - (7- hydroxyheplyl) - 7 - [3 - oxo - 4 - phenoxy (or p - chlorophenoxy) - but - trans - 1 - enyl] - 1,4- dioxaspiro[4,4]nonane; 6 - (6 - formylhexyl) - 7 - (3 - oxooct - trans - 1 - enyl) - 1,4 - dioxaspiro- [4,4]nonane; 6 - (6 - formylhexyl) - 7 - [3 - oxo- 4 - phenoxy (or p - chlorophenoxy) - but - trans - 1 - enyl] - 1,4 - dioxaspiro[4,4] - nonane; 6 - (8 - ethoxycarbonyl - oct - trans - 7 - enyl)- 7 - (3 - oxooct - trans - 1 - enyl) - 1,4 - dioxaspiro[4,4]nonane; 6 - (8 - ethoxycarbonylocttrans - 1 - enyl) - 7 - [3 - oxo - 4 - phenoxy (or p - chlorophenoxy) - but - trans - 1 - enyl] - 1,4- dioxaspiro[4,4]nonane; compounds of Formula V above; and 1-chloro-3-(p-chlorophenoxy)- acetone. 3 - (p - Chlorophenoxy) - 2 - oxopropylidene triphenylphosphorane is prepared by adding aqueous sodium bicarbonate solution to 2-oxo- (p - chlorophenoxy)propyltriphenylphosphonium chloride, obtained by reacting 1-chloro-3-(pchlorophenoxy) acetone with triphenylphosphine Pharmaceutical compositions, suitable for oral, rectal, vaginal or perenteral administration, contain the above 11-deoxyprostaglandins or non-toxic salts thereof or cyclodestrin clathrates thereof together with pharmaceutical carriers or coatings. The compounds possess similar pharmacological properties to the naturally occurring prostaglandins.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16429/75A GB1497829A (en) | 1975-04-21 | 1975-04-21 | 11-deoxyprostaglandins |
| BE166302A BE840924A (en) | 1975-04-21 | 1976-04-20 | NEW PROSTAGLANDIN ANALOGUES AND THEIR PREPARATION |
| AU13158/76A AU1315876A (en) | 1975-04-21 | 1976-04-20 | Prostaglandin analogues & pharmaceuticals |
| DK177176A DK177176A (en) | 1975-04-21 | 1976-04-20 | PROCEDURE FOR THE PREPARATION OF CYCLOPENTAN DERIVATIVES |
| FR7611566A FR2308357A1 (en) | 1975-04-21 | 1976-04-20 | NEW PROSTAGLANDIN ANALOGUES AND THEIR PREPARATION |
| JP51044206A JPS51138652A (en) | 1975-04-21 | 1976-04-20 | New cyclopentane derivatives |
| ZA762316A ZA762316B (en) | 1975-04-21 | 1976-04-20 | New cyclopentane derivatives |
| LU74796A LU74796A1 (en) | 1975-04-21 | 1976-04-20 | |
| DE19762617338 DE2617338A1 (en) | 1975-04-21 | 1976-04-21 | NEW CYCLOPENTAN DERIVATIVES |
| NL7604227A NL7604227A (en) | 1975-04-21 | 1976-04-21 | PROCEDURE FOR PREPARING A MEDICINAL PRODUCT CONTAINING A SOURCE CHODILATOR AND STOMACH PROTECTION AGAINST ACTION AS WELL AS FOR THE PREPARATION OF NEW CYCLOPENT DERIVATIVES. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16429/75A GB1497829A (en) | 1975-04-21 | 1975-04-21 | 11-deoxyprostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1497829A true GB1497829A (en) | 1978-01-12 |
Family
ID=10077160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16429/75A Expired GB1497829A (en) | 1975-04-21 | 1975-04-21 | 11-deoxyprostaglandins |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS51138652A (en) |
| AU (1) | AU1315876A (en) |
| BE (1) | BE840924A (en) |
| DE (1) | DE2617338A1 (en) |
| DK (1) | DK177176A (en) |
| FR (1) | FR2308357A1 (en) |
| GB (1) | GB1497829A (en) |
| LU (1) | LU74796A1 (en) |
| NL (1) | NL7604227A (en) |
| ZA (1) | ZA762316B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124489A (en) * | 1982-07-19 | 1984-02-22 | Ciba Geigy Ag | Medicinal composition containing pirprofen and cyclodextrin |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834249A1 (en) * | 1978-08-04 | 1980-02-28 | Hoechst Ag | NEW PROSTAGLAND DERIVATIVES IN THE DELTA 2-11-DESOXY-PGF TIEF 2 BZW. PGE DEEP 2 SERIES |
| EP2167546A1 (en) * | 2007-07-11 | 2010-03-31 | Ophthalmopharma AG | Complexes of prostaglandin derivatives and monosubstituted, charged beta-cyclodextrins |
-
1975
- 1975-04-21 GB GB16429/75A patent/GB1497829A/en not_active Expired
-
1976
- 1976-04-20 JP JP51044206A patent/JPS51138652A/en active Pending
- 1976-04-20 LU LU74796A patent/LU74796A1/xx unknown
- 1976-04-20 BE BE166302A patent/BE840924A/en unknown
- 1976-04-20 AU AU13158/76A patent/AU1315876A/en not_active Expired
- 1976-04-20 FR FR7611566A patent/FR2308357A1/en active Granted
- 1976-04-20 DK DK177176A patent/DK177176A/en unknown
- 1976-04-20 ZA ZA762316A patent/ZA762316B/en unknown
- 1976-04-21 NL NL7604227A patent/NL7604227A/en unknown
- 1976-04-21 DE DE19762617338 patent/DE2617338A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124489A (en) * | 1982-07-19 | 1984-02-22 | Ciba Geigy Ag | Medicinal composition containing pirprofen and cyclodextrin |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA762316B (en) | 1977-04-27 |
| BE840924A (en) | 1976-10-20 |
| LU74796A1 (en) | 1977-02-07 |
| DK177176A (en) | 1976-10-22 |
| FR2308357B1 (en) | 1979-10-05 |
| NL7604227A (en) | 1976-10-25 |
| AU1315876A (en) | 1977-10-27 |
| FR2308357A1 (en) | 1976-11-19 |
| DE2617338A1 (en) | 1976-11-04 |
| JPS51138652A (en) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |