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FR2145601A1 - Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activity - Google Patents

Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activity

Info

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
Application number
FR7225139A
Other languages
French (fr)
Other versions
FR2145601B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of FR2145601A1 publication Critical patent/FR2145601A1/en
Application granted granted Critical
Publication of FR2145601B1 publication Critical patent/FR2145601B1/fr
Granted legal-status Critical Current

Links

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.
FR7225139A 1971-07-14 1972-07-11 Prostaglandin analogues - with gastric secretion inhibiting bronchodilatory, hypotensive etc activity Granted FR2145601A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16271171A 1971-07-14 1971-07-14
US16271271A 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2358391A1 (en) * 1976-07-13 1978-02-10 Glaxo Lab Ltd PROSTAGLANDIN-ANALOGUE CYCLOHEXANE DERIVATIVES

Cited By (1)

* Cited by examiner, † Cited by third party
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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