BE805111A - 13,14-Dihydroprostaglandins - resistant to enzymatic deactivation, useful as muscle contractants, hypotensives etc - Google Patents
13,14-Dihydroprostaglandins - resistant to enzymatic deactivation, useful as muscle contractants, hypotensives etcInfo
- Publication number
- BE805111A BE805111A BE135871A BE135871A BE805111A BE 805111 A BE805111 A BE 805111A BE 135871 A BE135871 A BE 135871A BE 135871 A BE135871 A BE 135871A BE 805111 A BE805111 A BE 805111A
- Authority
- BE
- Belgium
- Prior art keywords
- alkyl
- substd
- pentyl
- hypotensives
- useful
- Prior art date
Links
- 208000001953 Hypotension Diseases 0.000 title abstract 2
- 208000021822 hypotensive Diseases 0.000 title abstract 2
- 230000001077 hypotensive effect Effects 0.000 title abstract 2
- 230000009849 deactivation Effects 0.000 title 1
- 230000002255 enzymatic effect Effects 0.000 title 1
- 210000003205 muscle Anatomy 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- -1 1-ethoxyethyl Chemical group 0.000 abstract 1
- 229920000858 Cyclodextrin Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 206010000210 abortion Diseases 0.000 abstract 1
- 231100000176 abortion Toxicity 0.000 abstract 1
- 230000003243 anti-lipolytic effect Effects 0.000 abstract 1
- 229940124630 bronchodilator Drugs 0.000 abstract 1
- 239000000168 bronchodilator agent Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229940124558 contraceptive agent Drugs 0.000 abstract 1
- 239000003433 contraceptive agent Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([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
- 230000000694 effects Effects 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical class O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 230000006698 induction Effects 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 150000003839 salts 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
- 210000002460 smooth muscle Anatomy 0.000 abstract 1
- 239000000021 stimulant Substances 0.000 abstract 1
- 239000002731 stomach secretion inhibitor Substances 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 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 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)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel title cpds. (I) salts, alcohol (i.e. CO2H reduced to CH2OH) esters and clathrates with cyclodextrin are of formula (A is one of the gps. and (a) R1 = linear 4-7C alkyl, opt. substd. by 1-3 1-4C alkyl; or 1-4C alkyl substd, by phenyl, cyclohexyl or cyclopentyl; R2 = H or 1-4C alkyl; R3 = H or 1-4C alkyl; provided that when A = (II) and R2 = H, R1 is not = n=pentyl; or (b) R1 = n-butyl, or m-butyl or n-pentyl substd. by 1-3 1-4C alkyl or 1-4C alkyl substd. as in (a), R2 = H or 1-4C alkyl; R3 = 1-4C alkyl). (I) have same activities as corresp. 13,14-dehydro cpds. and useful as smooth muscle stimulants in induction of labour or abortion; hypotensives, antilipolytics gastric secretion inhibitors, bronchodilators and contraceptives. Prepd. is by reacting (II) with Ph3P=CHCHICH(R3)CH2 CO2H (X = tetrahydropyranyl-2, opt. substd. tetrahydrofuranyl or 1-ethoxyethyl), deprotecting prod. (X) to give (I, A = III) (X) is alternatively oxidised and deprotected to (I, A = II) which may be dehydrate to (I, A = IV). This process also claimed for prodn. of the known PGE2 derivs where A = (II), R2 = H, R = n-pentyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47094972A JPS5130061B2 (en) | 1972-09-21 | 1972-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE805111A true BE805111A (en) | 1974-03-20 |
Family
ID=14124814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE135871A BE805111A (en) | 1972-09-21 | 1973-09-20 | 13,14-Dihydroprostaglandins - resistant to enzymatic deactivation, useful as muscle contractants, hypotensives etc |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5130061B2 (en) |
| BE (1) | BE805111A (en) |
| ZA (1) | ZA737459B (en) |
-
1972
- 1972-09-21 JP JP47094972A patent/JPS5130061B2/ja not_active Expired
-
1973
- 1973-09-20 BE BE135871A patent/BE805111A/en unknown
- 1973-09-20 ZA ZA737459A patent/ZA737459B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4949964A (en) | 1974-05-15 |
| JPS5130061B2 (en) | 1976-08-30 |
| ZA737459B (en) | 1974-08-28 |
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