FR2145601A1 - Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activity - Google Patents
Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activityInfo
- Publication number
- FR2145601A1 FR2145601A1 FR7225139A FR7225139A FR2145601A1 FR 2145601 A1 FR2145601 A1 FR 2145601A1 FR 7225139 A FR7225139 A FR 7225139A FR 7225139 A FR7225139 A FR 7225139A FR 2145601 A1 FR2145601 A1 FR 2145601A1
- Authority
- FR
- France
- Prior art keywords
- lower alkyl
- alkyl
- linear
- substd
- piperidino
- 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.)
- Granted
Links
- 208000001953 Hypotension Diseases 0.000 title 1
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title 1
- 230000003182 bronchodilatating effect Effects 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 230000002496 gastric effect Effects 0.000 title 1
- 208000021822 hypotensive Diseases 0.000 title 1
- 230000001077 hypotensive effect Effects 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 title 1
- 230000028327 secretion Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 20
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 7
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 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 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cpds. of formula (I) and their salts: (where n = 1 or 2, Y is CO, or alpha- or beta-CHOH, R1 is 3-10C linear alkyl, 2-6C Me-substd. linear alkyl, 3-6C linear alkenyl, 3-6C linear alkyl omega-substd. by halogen, SH or COOH, (CH2)pSR3, (CH2)pSOR3, (CH2)pCH(COOR3)2 or (CH2)qNR4R5, p = 2-4, q = 3-6, R3 is 1-3C alkyl, R4 and R5 are H, or lower alkyl, or NR4R5 is pyrrolidino, piperidino or morpholino, R2 is OH, 1-4C alkoxy, pyridoxy, CCl3CH2O, O(CH2)pNR4R5 or NR6R7, R6 is H, lower alkyl, alkenyl or alkynyl, cyclohexyl, phenyl-lower alkyl, or lower omega-hydroxyalkyl, R7 is H, lower alkyl, ON omega-di(lower alkyl) amino-lower alkyl, lower alkenyl or alkynyl, cyclohexyl, phenyl(opt. substd. by CF3, di(lower alkyl) amino, Cl or lower alkyl), pyridyl, lower alkyl (subst. by Ph or pyridyl or omega-substd by OH, lower alkoxy, di(lower alkyl)amino, piperidino, pyrrolidino or morpholino), NH2, di(lower alkyl)amino, N-piperidyl, N-hexamethyleneimino, N-morpholino, N-anilino or 4-lower alkyl-1-piperazino, or NR6R7 is pyrrolidino, piperidino, morpholino, hexamethyleneimino, 4-phenylpiperidino, 4-lower alkyl-1-piperazino, or NR6R7 is pyrrolidino, piperidino, morpholino, hexamethyleneimino, 4-phenylpiperidino, 4-lower alkyl-1-piperazino, 4-phenylpiperazino, 3-pyrrolidinyl, DELTA3-piperidino, 3-azabicyclo/3,2,2/nonyl, N,N'-bis(dialkylaminophenyl) ureido or 4,4'-spirocyclohexylpiperidyl, Z is (CH2)n, CH2CH=CH(CH2)p (cis), (CH2)qC(R3)2CH2, (CH2)qCR3H, (CH2)qOCH2 or (CH2)qSCH2, m = 1-8) are prepd. by reacting a cpd. (II). (where Z' is as Z but not CH2CH=CH(CH2)p, R' is alkyl) with / (R")3AlCH:CHR / - Li + (where R= is 1-6C alkyl, R is 3-10C linear alkyl, 2-6C Me-substd. linear alkyl, 3-6C linear alkenyl or 3-6C linear omega-chloroalkyl) to give (I, Y=CO, Z=Z', R2=OR', R1 = R) (Ia) (Ia, Z = CH2CH=CH(CH2)p) is prepd. by reacting (Ia, Z = CH2) with ethylene glycol, reducing the ester gp. to aldehyde, reacting with Ph3P=CH(CH2)p COOLi, and hydrolysing. These cpds. can be converted into other (I) by standard methods.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16271271A | 1971-07-14 | 1971-07-14 | |
| US16271171A | 1971-07-14 | 1971-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2145601A1 true FR2145601A1 (en) | 1973-02-23 |
| FR2145601B1 FR2145601B1 (en) | 1975-08-08 |
Family
ID=26859003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7225139A Granted FR2145601A1 (en) | 1971-07-14 | 1972-07-11 | Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activity |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2145601A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358391A1 (en) * | 1976-07-13 | 1978-02-10 | Glaxo Lab Ltd | PROSTAGLANDIN-ANALOGUE CYCLOHEXANE DERIVATIVES |
-
1972
- 1972-07-11 FR FR7225139A patent/FR2145601A1/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2358391A1 (en) * | 1976-07-13 | 1978-02-10 | Glaxo Lab Ltd | PROSTAGLANDIN-ANALOGUE CYCLOHEXANE DERIVATIVES |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2145601B1 (en) | 1975-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |