IT1120412B - Thia-analogues of prostaglandins - prepd e.g. by reacting 1-(carboxyalkyl)-1-cyclopentenes with thio cpds (SW081275 - Google Patents
Thia-analogues of prostaglandins - prepd e.g. by reacting 1-(carboxyalkyl)-1-cyclopentenes with thio cpds (SW081275Info
- Publication number
- IT1120412B IT1120412B IT4883379A IT4883379A IT1120412B IT 1120412 B IT1120412 B IT 1120412B IT 4883379 A IT4883379 A IT 4883379A IT 4883379 A IT4883379 A IT 4883379A IT 1120412 B IT1120412 B IT 1120412B
- Authority
- IT
- Italy
- Prior art keywords
- inhibitory
- substd
- och3
- phenoxy
- thia
- Prior art date
Links
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 abstract 1
- 206010002091 Anaesthesia Diseases 0.000 abstract 1
- 208000009079 Bronchial Spasm Diseases 0.000 abstract 1
- 208000014181 Bronchial disease Diseases 0.000 abstract 1
- 206010006482 Bronchospasm Diseases 0.000 abstract 1
- 241000282326 Felis catus Species 0.000 abstract 1
- 241000534944 Thia Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- 238000004220 aggregation Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000037005 anaesthesia Effects 0.000 abstract 1
- 238000001949 anaesthesia Methods 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940125717 barbiturate Drugs 0.000 abstract 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 210000004246 corpus luteum Anatomy 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 230000035558 fertility Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 210000002850 nasal mucosa Anatomy 0.000 abstract 1
- 229960002748 norepinephrine Drugs 0.000 abstract 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 abstract 1
- 210000003101 oviduct Anatomy 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- -1 phenoxy, pyridyl Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000028327 secretion Effects 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 230000032258 transport Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or 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
Abstract
Prostaglandin thia analogues of formula (I) (where A is CO or CHOH; B is CH2CH2 or CH=CH; R1 is H or 1-4C alkyl; m is 0-5; n is 0-3, and may also be 4-9 when B is CH=CH; R2 is 1-4C alkoxy, phenoxy, pyridyl, thienyl, naphthyl, phenyl, substd. by F, Cl, Br, OH, OCH3, or CF3, or phenoxy substd. by F, Cl, Br, OH, OCH3, CH3 or CF3, and may also be H, phenyl or tolyl when b is CH=CH; and indicates that configuration may be alpha or beta) e.g. 11, 15-dihydroxy-16-(p-fluorophenoxy)-15-methyl-9-oxo-17,18,19,20-tet- ranor-13-thiaprostanoic acid, and their physiologically innocuous salts are new cpds. (I ) have hypotensive activity (as shown when infused into cats under barbiturate anaesthesia) as well as vasodilatory, anti-inflammatory, diuretic, anti-bronchospasm, gastric secretion inhibitory, thrombocyte aggregation inhibitory, lipid breakdown inhibitory, noradrenaline release inhibitory and nasal mucosa contracting props. They also have effects on the corpus luteum, egg transport through the oviduct, nidation and fertility. (I) are also useful as inters. for other pharmaceuticals.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2422924A DE2422924A1 (en) | 1974-05-11 | 1974-05-11 | THIAPROSTAGLANDINE |
| DE19752513371 DE2513371C2 (en) | 1975-03-26 | 1975-03-26 | 9,11,15-trihydroxy-13-thia-5-prostenic acid derivatives and pharmaceutical preparations containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT7948833A0 IT7948833A0 (en) | 1979-04-24 |
| IT1120412B true IT1120412B (en) | 1986-03-26 |
Family
ID=25767110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT4883379A IT1120412B (en) | 1974-05-11 | 1979-04-24 | Thia-analogues of prostaglandins - prepd e.g. by reacting 1-(carboxyalkyl)-1-cyclopentenes with thio cpds (SW081275 |
Country Status (2)
| Country | Link |
|---|---|
| IT (1) | IT1120412B (en) |
| SE (2) | SE419755B (en) |
-
1975
- 1975-05-06 SE SE7505224A patent/SE419755B/en not_active IP Right Cessation
-
1978
- 1978-08-28 SE SE7809051A patent/SE428207B/en not_active IP Right Cessation
-
1979
- 1979-04-24 IT IT4883379A patent/IT1120412B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT7948833A0 (en) | 1979-04-24 |
| SE428207B (en) | 1983-06-13 |
| SE419755B (en) | 1981-08-24 |
| SE7505224L (en) | 1975-11-12 |
| SE7809051L (en) | 1978-08-29 |
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