GB1332008A - Piperazine derivatives their preparation and pharmaceutical compositions containing them - Google Patents

Piperazine derivatives their preparation and pharmaceutical compositions containing them

Info

Publication number
GB1332008A
GB1332008A GB1332008DA GB1332008A GB 1332008 A GB1332008 A GB 1332008A GB 1332008D A GB1332008D A GB 1332008DA GB 1332008 A GB1332008 A GB 1332008A
Authority
GB
United Kingdom
Prior art keywords
compounds
alkyl
reacting
methoxyphenyl
alkoxycarbonyl
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
Application number
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.)
Pfizer Ltd
Original Assignee
Pfizer Ltd
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 Pfizer Ltd filed Critical Pfizer Ltd
Publication of GB1332008A publication Critical patent/GB1332008A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Abstract

1332008 Piperazine derivatives PFIZER Ltd 28 Sept 1971 [23 Nov 1970] 55647/70 Addition to 1325876 Heading C2C The invention comprises novel piperazine derivatives of the Formula I wherein R is R<SP>6</SP>R<SP>7</SP>NCON(R<SP>8</SP>)-, R<SP>6</SP>R<SP>7</SP>NCSN(R<SP>8</SP>)-, R<SP>6</SP>R<SP>7</SP>NSO 2 N(R<SP>8</SP>)-, R<SP>6</SP>R<SP>7</SP>NCO-, R<SP>6</SP>R<SP>7</SP>NCS, R<SP>6</SP>R<SP>7</SP>NSO 2 -, wherein R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> are H, C 1-6 alkyl, aryl or aryl- C 1-6 alkyl, or R<SP>4</SP>OCON(R<SP>5</SP>)-, wherein R<SP>4</SP> is C 1-6 alkyl and R<SP>5</SP> is H or C 1-6 alkyl, or CN, COOH, C 1-6 alkoxycarbonyl, or N-aminocarbamoyl; R<SP>1</SP> is H, halogen, OH, OCH 3 or C 1-6 alkyl; R<SP>2</SP> is H or C 1-6 alkyl, R<SP>3</SP> is halogen, C 1-6 alkyl or C 1-6 alkoxy; n is 0, 1 or 2; and X is O or S; the esters of those compounds in which R<SP>2</SP> is H; and the N-oxides and pharmaceutically acceptable acid addition salts thereof. The novel compounds are prepared by one of the following methods: (1) Compounds in which R<SP>2</SP> is H and in which R<SP>1</SP> is as above except OH by reacting the appropriately substituted 1-phenoxy (or phenylthio)- 2,3-epoxypropane with the corresponding N- phenylpiperazines. (2) By reacting the appropriate phenoxy or phenylthio substituted propylene chlorohydrins or ethers thereof with the corresponding N- phenylpiperazine. (3) By reacting suitably substituted phenoxy- or phenylthiopropanolamines or ethers thereof with the corresponding N,N-bis-(2- chloroethyl)anilines. (4) Compounds in which R is COOH by hydrolysing the corresponding compounds in which R is carbamoyl or C 1-6 alkoxycarbonyl. (5) Compounds in which R is C 1-6 alkoxycarbonyl by esterifying the corresponding compounds in which R is COOH. (6) Compounds in which R is NHCONH 2 or NHCSNH 2 by reacting the corresponding compounds in which R is NH 2 with alkali metal cyanates or thiocyanates, respectively. (7) Compounds in which R is N-aminocarbamoyl by reacting the corresponding compounds in which R is C 1-6 alkoxycarbonyl with hydrazine hydrate. (8) Compounds in which R<SP>1</SP> is OH by hydrogenolysis of the corresponding benzyl ethers. (9) Compounds in which R<SP>2</SP> is alkyl and esters of compounds in which R<SP>2</SP> is H by alkylation and esterification of the corresponding compounds in which R<SP>2</SP> is H. 1 - (2 - Aminophenoxyl) - 3 - [4 - (2 - methoxyphenyl) - piperazin - 1 - yl] - propan - 2 - ol hydrochloride is obtained by hydrolysing 1-(2- acetamidophenoxy) - 3 - [4 - (2 - methoxyphenyl)- piperazin-1-yl]-propan-2-ol, resulting from the reaction between 1-(2-acetamidophenoxy)-2,3- epoxypropane and 1-(2-methoxyphenyl)-piperazine. 1 - (4 - Benzyloxy - 2 - carbamoylphenoxy) - 3- [4 - (2 - methoxyphenyl)piperazin- 1 - yl] - propan- 2-ol is obtained by reacting 1-(4-benzyloxy-2- carbamoylphenoxy) - 2,3 - epoxypropane with 1-(2-methoxyphenyl)-piperazine. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compounds and suitable carrier therefor. The compounds possess anti-hypertensive activity.
GB1332008D 1971-09-28 1971-09-28 Piperazine derivatives their preparation and pharmaceutical compositions containing them Expired GB1332008A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5564770 1971-09-28

Publications (1)

Publication Number Publication Date
GB1332008A true GB1332008A (en) 1973-10-03

Family

ID=10474469

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1332008D Expired GB1332008A (en) 1971-09-28 1971-09-28 Piperazine derivatives their preparation and pharmaceutical compositions containing them

Country Status (1)

Country Link
GB (1) GB1332008A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4558129A (en) * 1983-05-18 1985-12-10 Syntex (U.S.A.) Inc. Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade
US4567264A (en) * 1983-05-18 1986-01-28 Syntex (U.S.A.) Inc. Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
WO2001034569A1 (en) * 1999-11-11 2001-05-17 Senju Pharmaceutical Co., Ltd. Pancreatitis remedies
US7897764B2 (en) * 2007-06-08 2011-03-01 National Health Research Institutes Thiourea derivatives
US7985763B2 (en) 2007-04-10 2011-07-26 National Health Research Institutes Hepatitis C virus inhibitors
US8198284B2 (en) 2008-04-30 2012-06-12 National Health Research Institutes Treatment of neurodegenerative disorders with thiourea compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4558129A (en) * 1983-05-18 1985-12-10 Syntex (U.S.A.) Inc. Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade
US4567264A (en) * 1983-05-18 1986-01-28 Syntex (U.S.A.) Inc. Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry
WO2001034569A1 (en) * 1999-11-11 2001-05-17 Senju Pharmaceutical Co., Ltd. Pancreatitis remedies
US7985763B2 (en) 2007-04-10 2011-07-26 National Health Research Institutes Hepatitis C virus inhibitors
US7897764B2 (en) * 2007-06-08 2011-03-01 National Health Research Institutes Thiourea derivatives
US8198284B2 (en) 2008-04-30 2012-06-12 National Health Research Institutes Treatment of neurodegenerative disorders with thiourea compounds

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee