GB1332008A - Piperazine derivatives their preparation and pharmaceutical compositions containing them - Google Patents
Piperazine derivatives their preparation and pharmaceutical compositions containing themInfo
- 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
Links
- 150000004885 piperazines Chemical class 0.000 title abstract 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 17
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- -1 or CN Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 abstract 3
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- HPFMMSAXKLZXQL-UHFFFAOYSA-N 1-(2-aminophenoxy)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol hydrochloride Chemical compound Cl.NC1=C(OCC(CN2CCN(CC2)C2=C(C=CC=C2)OC)O)C=CC=C1 HPFMMSAXKLZXQL-UHFFFAOYSA-N 0.000 abstract 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical class CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 abstract 1
- IIIITSLQZUEWDE-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-5-phenylmethoxybenzamide Chemical compound C(C1=CC=CC=C1)OC1=CC(=C(OCC2CO2)C=C1)C(N)=O IIIITSLQZUEWDE-UHFFFAOYSA-N 0.000 abstract 1
- PQILSMNQBHIBLG-UHFFFAOYSA-N 2-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-5-phenylmethoxybenzamide Chemical compound C(C1=CC=CC=C1)OC1=CC(=C(OCC(CN2CCN(CC2)C2=C(C=CC=C2)OC)O)C=C1)C(N)=O PQILSMNQBHIBLG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- URINYHFMLIGJCL-UHFFFAOYSA-N NCSN Chemical compound NCSN URINYHFMLIGJCL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- ROSJKFFLIXTTAW-UHFFFAOYSA-N n,n-bis(2-chloroethyl)aniline Chemical class ClCCN(CCCl)C1=CC=CC=C1 ROSJKFFLIXTTAW-UHFFFAOYSA-N 0.000 abstract 1
- SENIMHNFLVMDJV-UHFFFAOYSA-N n-[2-(oxiran-2-ylmethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1OCC1OC1 SENIMHNFLVMDJV-UHFFFAOYSA-N 0.000 abstract 1
- DQEXEEDCMTXOIJ-UHFFFAOYSA-N n-[2-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]phenyl]acetamide Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C(=CC=CC=2)NC(C)=O)CC1 DQEXEEDCMTXOIJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000007911 parenteral administration Methods 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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.
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)
| 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 |
-
1971
- 1971-09-28 GB GB1332008D patent/GB1332008A/en not_active Expired
Cited By (6)
| 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 |