GB1166595A - Improvements in or relating to Piperazinyl Derivatives - Google Patents
Improvements in or relating to Piperazinyl DerivativesInfo
- Publication number
- GB1166595A GB1166595A GB850368A GB850368A GB1166595A GB 1166595 A GB1166595 A GB 1166595A GB 850368 A GB850368 A GB 850368A GB 850368 A GB850368 A GB 850368A GB 1166595 A GB1166595 A GB 1166595A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- atoms inclusive
- aryl
- halogen
- radical
- 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
- 125000004193 piperazinyl group Chemical group 0.000 title 1
- -1 cyanoalkyl radical Chemical class 0.000 abstract 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 229910052736 halogen Chemical group 0.000 abstract 5
- 150000002367 halogens Chemical group 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- YEQDVKYOHVLZPU-UHFFFAOYSA-N n-phenylpiperazine-1-carboxamide Chemical class C1CNCCN1C(=O)NC1=CC=CC=C1 YEQDVKYOHVLZPU-UHFFFAOYSA-N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- VZZAYMIPTIBJLI-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC(N)=C(S(N)(=O)=O)C=C1OC VZZAYMIPTIBJLI-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004950 trifluoroalkyl group Chemical group 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
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 abstract 1
- HJNFZYKXXGPAJW-UHFFFAOYSA-N 4,5-dimethoxy-2-nitrobenzenesulfonamide Chemical compound COC1=CC([N+]([O-])=O)=C(S(N)(=O)=O)C=C1OC HJNFZYKXXGPAJW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 230000004531 blood pressure lowering effect Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000004885 piperazines Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB0091744 | 1967-03-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1166595A true GB1166595A (en) | 1969-10-08 |
Family
ID=6986011
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB850368A Expired GB1166595A (en) | 1967-03-22 | 1968-02-21 | Improvements in or relating to Piperazinyl Derivatives |
Country Status (9)
Country | Link |
---|---|
AT (1) | AT278814B (enrdf_load_stackoverflow) |
BE (1) | BE710768A (enrdf_load_stackoverflow) |
CH (1) | CH507260A (enrdf_load_stackoverflow) |
DE (1) | DE1670200A1 (enrdf_load_stackoverflow) |
ES (1) | ES351896A1 (enrdf_load_stackoverflow) |
FR (1) | FR1577338A (enrdf_load_stackoverflow) |
GB (1) | GB1166595A (enrdf_load_stackoverflow) |
NL (1) | NL6802185A (enrdf_load_stackoverflow) |
SE (1) | SE343582B (enrdf_load_stackoverflow) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4336382A (en) * | 1979-09-06 | 1982-06-22 | Hoffmann-La Roche Inc. | 1,4-Disubstituted piperazine compounds |
JPS59152379A (ja) * | 1983-02-12 | 1984-08-31 | レコルダチ エス エ− ケミカル アンド フアマシユテイカル カンパニ− | N―ピペラジニルアルカノイルアニリド及びその製造法 |
WO1989006961A1 (en) * | 1988-01-29 | 1989-08-10 | Mitsubishi Kasei Corporation | Antianxiety drug |
US5219855A (en) * | 1988-01-29 | 1993-06-15 | Mitsubishi Kasei Corporation | Anxiolytic drug |
US5364849A (en) * | 1989-04-22 | 1994-11-15 | John Wyeth & Brother, Limited | 1-[3 or 4-[1-[4-piperazinyl]]-2 arylpropionyl or butryl]-heterocyclic derivatives |
US5382583A (en) * | 1989-04-22 | 1995-01-17 | John Wyeth & Brother, Limited | Piperazine derivatives |
US5403842A (en) * | 1992-02-25 | 1995-04-04 | Recordati S.A., Chemical And Pharmaceutical Company | Benzopyran and benzothiopyran derivatives |
US5453518A (en) * | 1992-04-10 | 1995-09-26 | Recordati S.A., Chemical And Pharmaceutical Company | Flavone derivatives |
US5474994A (en) * | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
US5605896A (en) * | 1992-02-25 | 1997-02-25 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4202978A (en) * | 1978-02-08 | 1980-05-13 | Hoffmann-La Roche Inc. | (S)-1-[2-(4-(2-Hydroxy-s-(1-alkylaminopropoxy)phenylalkyl]-4-phenylpiperazines |
US4766125A (en) * | 1981-06-23 | 1988-08-23 | Janssen Pharmaceutica N.V. | N-aryl-piperazinealkanamides useful for protecting hearts from myocardial injury caused by ischaemia, anoxia or hypoxia |
-
1967
- 1967-03-22 DE DE19671670200 patent/DE1670200A1/de active Pending
-
1968
- 1968-01-31 AT AT96368A patent/AT278814B/de not_active IP Right Cessation
- 1968-01-31 CH CH149168A patent/CH507260A/de not_active IP Right Cessation
- 1968-02-14 BE BE710768D patent/BE710768A/xx unknown
- 1968-02-15 NL NL6802185A patent/NL6802185A/xx unknown
- 1968-02-21 GB GB850368A patent/GB1166595A/en not_active Expired
- 1968-03-13 SE SE329168A patent/SE343582B/xx unknown
- 1968-03-20 FR FR1577338D patent/FR1577338A/fr not_active Expired
- 1968-03-22 ES ES351896A patent/ES351896A1/es not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4336382A (en) * | 1979-09-06 | 1982-06-22 | Hoffmann-La Roche Inc. | 1,4-Disubstituted piperazine compounds |
JPS59152379A (ja) * | 1983-02-12 | 1984-08-31 | レコルダチ エス エ− ケミカル アンド フアマシユテイカル カンパニ− | N―ピペラジニルアルカノイルアニリド及びその製造法 |
EP0120558A1 (en) * | 1983-02-12 | 1984-10-03 | RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY | Antihypertensive N-piperazinylalkanoylanilides |
US4940711A (en) * | 1983-02-12 | 1990-07-10 | Recordati, S.A., Chemical And Pharmaceutical Company | Antihypertensive N-piperazinylalkanoylanilides |
WO1989006961A1 (en) * | 1988-01-29 | 1989-08-10 | Mitsubishi Kasei Corporation | Antianxiety drug |
US5219855A (en) * | 1988-01-29 | 1993-06-15 | Mitsubishi Kasei Corporation | Anxiolytic drug |
US5364849A (en) * | 1989-04-22 | 1994-11-15 | John Wyeth & Brother, Limited | 1-[3 or 4-[1-[4-piperazinyl]]-2 arylpropionyl or butryl]-heterocyclic derivatives |
US5382583A (en) * | 1989-04-22 | 1995-01-17 | John Wyeth & Brother, Limited | Piperazine derivatives |
US5403842A (en) * | 1992-02-25 | 1995-04-04 | Recordati S.A., Chemical And Pharmaceutical Company | Benzopyran and benzothiopyran derivatives |
US5605896A (en) * | 1992-02-25 | 1997-02-25 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 adrenergic and 5HT1A activities |
US5453518A (en) * | 1992-04-10 | 1995-09-26 | Recordati S.A., Chemical And Pharmaceutical Company | Flavone derivatives |
US5474994A (en) * | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
Also Published As
Publication number | Publication date |
---|---|
SE343582B (enrdf_load_stackoverflow) | 1972-03-13 |
DE1670200A1 (de) | 1972-03-02 |
BE710768A (enrdf_load_stackoverflow) | 1968-06-17 |
FR1577338A (enrdf_load_stackoverflow) | 1969-08-08 |
CH507260A (de) | 1971-05-15 |
NL6802185A (enrdf_load_stackoverflow) | 1968-09-23 |
ES351896A1 (es) | 1969-06-16 |
AT278814B (de) | 1970-02-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |