NL8600071A - Anti-psychotische, cyclische imidederivaten van 2-(4-butylpiperazine-1-yl)pyridines. - Google Patents
Anti-psychotische, cyclische imidederivaten van 2-(4-butylpiperazine-1-yl)pyridines. Download PDFInfo
- Publication number
- NL8600071A NL8600071A NL8600071A NL8600071A NL8600071A NL 8600071 A NL8600071 A NL 8600071A NL 8600071 A NL8600071 A NL 8600071A NL 8600071 A NL8600071 A NL 8600071A NL 8600071 A NL8600071 A NL 8600071A
- Authority
- NL
- Netherlands
- Prior art keywords
- piperazinyl
- formula
- butyl
- pyridinyl
- group
- Prior art date
Links
- -1 4-BUTYLPIPERAZINE-1-YL Chemical class 0.000 title claims description 33
- 230000000561 anti-psychotic effect Effects 0.000 title claims description 11
- 150000003949 imides Chemical class 0.000 title description 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- KFBXUKHERGLHLG-UHFFFAOYSA-N 2,4-Nonanedione Chemical compound CCCCCC(=O)CC(C)=O KFBXUKHERGLHLG-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- VXLBZLIRRKSIMG-UHFFFAOYSA-N 1-[4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C(=CC=CN=2)Cl)CC1 VXLBZLIRRKSIMG-UHFFFAOYSA-N 0.000 claims 1
- OBCWRHFHKMQBHO-UHFFFAOYSA-N 1-[4-[4-(6-methoxypyridin-2-yl)piperazin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound COC1=CC=CC(N2CCN(CCCCN3C(CC(C)(C)CC3=O)=O)CC2)=N1 OBCWRHFHKMQBHO-UHFFFAOYSA-N 0.000 claims 1
- ZJBQDVPBSVJESO-UHFFFAOYSA-N 2-[4-[4-(2,4-dioxo-1-thia-3-azaspiro[4.4]nonan-3-yl)butyl]piperazin-1-yl]pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1N1CCN(CCCCN2C(C3(CCCC3)SC2=O)=O)CC1 ZJBQDVPBSVJESO-UHFFFAOYSA-N 0.000 claims 1
- VRWHAGFNMQIDTP-UHFFFAOYSA-N 2-[4-[4-(3,5-dioxomorpholin-4-yl)butyl]piperazin-1-yl]pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1N1CCN(CCCCN2C(COCC2=O)=O)CC1 VRWHAGFNMQIDTP-UHFFFAOYSA-N 0.000 claims 1
- PTBHTCKFKFQPHA-UHFFFAOYSA-N 3-[4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound ClC1=CC=CN=C1N1CCN(CCCCN2C(C3(CCCC3)SC2=O)=O)CC1 PTBHTCKFKFQPHA-UHFFFAOYSA-N 0.000 claims 1
- JELPGWKOZZCYSJ-UHFFFAOYSA-N 3-[4-[4-(3-methoxypyridin-2-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound COC1=CC=CN=C1N1CCN(CCCCN2C(C3(CCCC3)SC2=O)=O)CC1 JELPGWKOZZCYSJ-UHFFFAOYSA-N 0.000 claims 1
- WFEOSUOHPMGASR-UHFFFAOYSA-N 3-[4-[4-(3-nitropyridin-2-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound [O-][N+](=O)C1=CC=CN=C1N1CCN(CCCCN2C(C3(CCCC3)SC2=O)=O)CC1 WFEOSUOHPMGASR-UHFFFAOYSA-N 0.000 claims 1
- FUPHESAHOIDKIG-UHFFFAOYSA-N 3-[4-[4-(3-phenylpyridin-2-yl)piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound O=C1N(CCCCN2CCN(CC2)C=2C(=CC=CN=2)C=2C=CC=CC=2)C(=O)SC21CCCC2 FUPHESAHOIDKIG-UHFFFAOYSA-N 0.000 claims 1
- SULWINHUDLUHEP-UHFFFAOYSA-N 3-[4-[4-[3-(methoxyiminomethyl)pyridin-2-yl]piperazin-1-yl]butyl]-1-thia-3-azaspiro[4.4]nonane-2,4-dione Chemical compound CON=CC1=CC=CN=C1N1CCN(CCCCN2C(C3(CCCC3)SC2=O)=O)CC1 SULWINHUDLUHEP-UHFFFAOYSA-N 0.000 claims 1
- WXONACZIXYFYMN-UHFFFAOYSA-N 4,4-dimethyl-1-[4-[4-(3-phenylpyridin-2-yl)piperazin-1-yl]butyl]piperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2C(=CC=CN=2)C=2C=CC=CC=2)CC1 WXONACZIXYFYMN-UHFFFAOYSA-N 0.000 claims 1
- RTBFPRRGWFDRQC-UHFFFAOYSA-N 4-[4-[4-(3-nitropyridin-2-yl)piperazin-1-yl]butyl]morpholine-3,5-dione Chemical compound [O-][N+](=O)C1=CC=CN=C1N1CCN(CCCCN2C(COCC2=O)=O)CC1 RTBFPRRGWFDRQC-UHFFFAOYSA-N 0.000 claims 1
- ZYEYMMNRQTZSCP-UHFFFAOYSA-N 4-[4-[4-(3-phenylpyridin-2-yl)piperazin-1-yl]butyl]morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1CCCCN1CCN(C=2C(=CC=CN=2)C=2C=CC=CC=2)CC1 ZYEYMMNRQTZSCP-UHFFFAOYSA-N 0.000 claims 1
- KOESHJOJISMAQL-UHFFFAOYSA-N 8-[4-[4-(3-methoxypyridin-2-yl)piperazin-1-yl]butyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound COC1=CC=CN=C1N1CCN(CCCCN2C(CC3(CCCC3)CC2=O)=O)CC1 KOESHJOJISMAQL-UHFFFAOYSA-N 0.000 claims 1
- UAMYAAMXKHZTHX-UHFFFAOYSA-N 8-[4-[4-(3-methylpyridin-2-yl)piperazin-1-yl]butyl]-8-azaspiro[4.5]decane-7,9-dione Chemical compound CC1=CC=CN=C1N1CCN(CCCCN2C(CC3(CCCC3)CC2=O)=O)CC1 UAMYAAMXKHZTHX-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 20
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
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- MVKDNXIKAWKCCS-UHFFFAOYSA-N 3-methyl-1h-pyridin-2-one Chemical compound CC1=CC=CN=C1O MVKDNXIKAWKCCS-UHFFFAOYSA-N 0.000 description 6
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- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/691,952 US4619930A (en) | 1985-01-16 | 1985-01-16 | Antipsychotic cyclic imide derivatives of 2-(4-butylpiperazin-1-yl)pyridines, compositions and use |
| US69195285 | 1985-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8600071A true NL8600071A (nl) | 1986-08-18 |
Family
ID=24778661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8600071A NL8600071A (nl) | 1985-01-16 | 1986-01-15 | Anti-psychotische, cyclische imidederivaten van 2-(4-butylpiperazine-1-yl)pyridines. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4619930A (de) |
| JP (1) | JPH0780873B2 (de) |
| KR (1) | KR900000366B1 (de) |
| CN (1) | CN1016691B (de) |
| AT (1) | AT391698B (de) |
| AU (1) | AU591473B2 (de) |
| BE (1) | BE904047A (de) |
| CA (1) | CA1284325C (de) |
| CH (1) | CH666269A5 (de) |
| DE (1) | DE3601143C2 (de) |
| DK (1) | DK19286A (de) |
| EG (1) | EG17759A (de) |
| ES (2) | ES8705869A1 (de) |
| FI (1) | FI90077C (de) |
| FR (1) | FR2580282B1 (de) |
| GB (1) | GB2191772B (de) |
| HU (1) | HU198202B (de) |
| IE (1) | IE58866B1 (de) |
| IL (1) | IL77577A (de) |
| IT (1) | IT1214497B (de) |
| LU (1) | LU86248A1 (de) |
| NL (1) | NL8600071A (de) |
| NZ (1) | NZ214790A (de) |
| OA (1) | OA08187A (de) |
| PT (1) | PT81843B (de) |
| SE (1) | SE466310B (de) |
| SU (1) | SU1521282A3 (de) |
| YU (1) | YU45757B (de) |
| ZA (1) | ZA859692B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4677104A (en) * | 1985-05-06 | 1987-06-30 | Bristol-Myers Company | Antipsychotic fused-ring pyridinylpiperazine derivatives |
| US4812567A (en) * | 1985-10-16 | 1989-03-14 | American Home Products Corporation | Polycyclic spiroimides with psychotropic activity |
| MX174210B (es) * | 1987-02-17 | 1994-04-28 | Pfizer | Procedimiento para la preparacion de compuestos arilpiperazinil-alquilenfenil-p-heterociclicos |
| US4748240A (en) * | 1987-04-03 | 1988-05-31 | American Home Products Corporation | Psychotropic bicyclic imides |
| ATE81123T1 (de) * | 1987-11-20 | 1992-10-15 | Hoechst Roussel Pharma | 3-(4(1-substituierte-4-piperazinyl)butyl>-4thiazolidinone, verfahren zu deren herstellung und ihre anwendung als arzneimittel. |
| US4880930A (en) * | 1987-11-30 | 1989-11-14 | New James S | Psychotropic acyclic amide derivatives |
| US5001130A (en) * | 1988-02-18 | 1991-03-19 | Bristol-Myers Company | Psychotropic heterobicycloalkylpiperazine derivatives |
| US5116970A (en) * | 1988-02-18 | 1992-05-26 | New James S | Psychotropic heterobicycloalkylpiperazine derivatives: 2. fused pyridazinones |
| DK0482696T3 (da) * | 1990-10-23 | 1996-05-20 | Akzo Nobel Nv | 4-(4- eller 6-(trifluormethyl-2-pyridinyl))-1-piperazinylalkyl-substituerede lactamer |
| DE4232175A1 (de) | 1992-04-15 | 1993-10-21 | Bayer Ag | Verfahren zur Herstellung von 2-Amino-5-methyl-pyridin |
| KR100254666B1 (ko) * | 1994-07-15 | 2000-05-01 | 이치로 키타사토 | 혈소판 응집 저해 작용을 갖는 신규 화합물 |
| RU2126001C1 (ru) * | 1995-01-10 | 1999-02-10 | Самдзин Фармасьютикал Ко., Лтд | Производные пиперазина и фармацевтическая композиция на их основе |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
| CN104230915B (zh) * | 2014-08-29 | 2016-08-17 | 南京大学 | 含噻唑烷二酮的苯基哌嗪衍生物及其制备方法与用途 |
| CN104513198A (zh) * | 2014-11-29 | 2015-04-15 | 南京红太阳生物化学有限责任公司 | 一种2-氯烟酸的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| US3976776A (en) * | 1972-12-06 | 1976-08-24 | Mead Johnson & Company | Tranquilizer process employing N-(heteroarcyclic)piperazinylalkylazaspiroalkanediones |
| AT330777B (de) * | 1973-09-08 | 1976-07-26 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen isochinolinderivaten und deren salzen |
| US4305944A (en) * | 1980-09-08 | 1981-12-15 | Mead Johnson & Company | N-[(4-[3-cyano substituted pyridyl]piperazino)alkyl]-azaspirodecanediones |
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4456756A (en) * | 1981-08-03 | 1984-06-26 | Mead Johnson & Company | Spirothiazolidinyl piperazine derivatives |
| DE3135532A1 (de) * | 1981-09-08 | 1983-03-24 | NPL po Dvigateli s Vatrešno Gorene, Varna | Brennkraftmaschine |
| US4361565A (en) * | 1981-12-28 | 1982-11-30 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyridines |
| JPS5976059A (ja) * | 1982-10-21 | 1984-04-28 | Sumitomo Chem Co Ltd | 環状イミド誘導体及びその酸付加塩 |
| JPS61238784A (ja) * | 1985-04-17 | 1986-10-24 | Sumitomo Seiyaku Kk | コハク酸イミド誘導体及びその酸付加塩 |
| DE3529872A1 (de) * | 1985-08-21 | 1987-02-26 | Kali Chemie Pharma Gmbh | Neue tetraoxoverbindungen |
-
1985
- 1985-01-16 US US06/691,952 patent/US4619930A/en not_active Expired - Lifetime
- 1985-12-19 ZA ZA859692A patent/ZA859692B/xx unknown
- 1985-12-31 FR FR8519488A patent/FR2580282B1/fr not_active Expired - Lifetime
-
1986
- 1986-01-10 NZ NZ214790A patent/NZ214790A/xx unknown
- 1986-01-10 CA CA000499331A patent/CA1284325C/en not_active Expired - Fee Related
- 1986-01-13 FI FI860136A patent/FI90077C/fi not_active IP Right Cessation
- 1986-01-13 IL IL77577A patent/IL77577A/xx not_active IP Right Cessation
- 1986-01-13 ES ES550829A patent/ES8705869A1/es not_active Expired
- 1986-01-13 YU YU4186A patent/YU45757B/sh unknown
- 1986-01-14 JP JP61006146A patent/JPH0780873B2/ja not_active Expired - Lifetime
- 1986-01-15 IE IE12586A patent/IE58866B1/en not_active IP Right Cessation
- 1986-01-15 DK DK19286A patent/DK19286A/da not_active Application Discontinuation
- 1986-01-15 KR KR1019860000203A patent/KR900000366B1/ko not_active Expired
- 1986-01-15 CH CH130/86A patent/CH666269A5/de not_active IP Right Cessation
- 1986-01-15 BE BE0/216140A patent/BE904047A/fr not_active IP Right Cessation
- 1986-01-15 PT PT81843A patent/PT81843B/pt unknown
- 1986-01-15 SE SE8600173A patent/SE466310B/sv not_active IP Right Cessation
- 1986-01-15 IT IT8619081A patent/IT1214497B/it active
- 1986-01-15 SU SU864011790A patent/SU1521282A3/ru active
- 1986-01-15 LU LU86248A patent/LU86248A1/fr unknown
- 1986-01-15 CN CN86100224A patent/CN1016691B/zh not_active Expired
- 1986-01-15 OA OA58765A patent/OA08187A/xx unknown
- 1986-01-15 HU HU86207A patent/HU198202B/hu unknown
- 1986-01-15 NL NL8600071A patent/NL8600071A/nl active Search and Examination
- 1986-01-16 AT AT0010086A patent/AT391698B/de not_active IP Right Cessation
- 1986-01-16 AU AU52294/86A patent/AU591473B2/en not_active Expired
- 1986-01-16 EG EG20/86A patent/EG17759A/xx active
- 1986-01-16 DE DE3601143A patent/DE3601143C2/de not_active Expired - Lifetime
- 1986-06-17 GB GB8614686A patent/GB2191772B/en not_active Expired - Lifetime
-
1987
- 1987-02-13 ES ES557390A patent/ES8801822A1/es not_active Expired
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