DD272077A5 - Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen - Google Patents
Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen Download PDFInfo
- Publication number
- DD272077A5 DD272077A5 DD88313286A DD31328688A DD272077A5 DD 272077 A5 DD272077 A5 DD 272077A5 DD 88313286 A DD88313286 A DD 88313286A DD 31328688 A DD31328688 A DD 31328688A DD 272077 A5 DD272077 A5 DD 272077A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- mmol
- ethyl acetate
- piperazinyl
- evaporated
- ethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- -1 nitro, quinolyl Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 238000010992 reflux Methods 0.000 description 48
- 239000007787 solid Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 37
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 229910000029 sodium carbonate Inorganic materials 0.000 description 19
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical group C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 235000009518 sodium iodide Nutrition 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 241000400611 Eucalyptus deanei Species 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229960004592 isopropanol Drugs 0.000 description 6
- VNICFCQJUVFULD-UHFFFAOYSA-N 1-(1-naphthalenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=CC=CC=C12 VNICFCQJUVFULD-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000005999 2-bromoethyl group Chemical group 0.000 description 3
- WXJWBEAGVWVEDM-UHFFFAOYSA-N 5-(2-chloroacetyl)-1,3-dihydroindol-2-one Chemical compound ClCC(=O)C1=CC=C2NC(=O)CC2=C1 WXJWBEAGVWVEDM-UHFFFAOYSA-N 0.000 description 3
- HPXJIGZLXHQSGU-UHFFFAOYSA-N 5-(2-chloroethyl)-1,3-dihydroindol-2-one Chemical compound ClCCC1=CC=C2NC(=O)CC2=C1 HPXJIGZLXHQSGU-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000001990 intravenous administration Methods 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- KOOKQPMRBFPCJH-UHFFFAOYSA-N 1-benzyl-4-(6-fluoronaphthalen-1-yl)piperazine Chemical compound C=1C=CC2=CC(F)=CC=C2C=1N(CC1)CCN1CC1=CC=CC=C1 KOOKQPMRBFPCJH-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- YIDMPLFTBQMVAQ-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-2,1,3-benzothiadiazole Chemical compound C1CN(C)CCN1C1=CC=CC2=NSN=C12 YIDMPLFTBQMVAQ-UHFFFAOYSA-N 0.000 description 2
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- AEJRZACCYFBKJC-UHFFFAOYSA-N 6-(4-hydroxybutyl)-3h-1,3-benzoxazol-2-one Chemical compound OCCCCC1=CC=C2NC(=O)OC2=C1 AEJRZACCYFBKJC-UHFFFAOYSA-N 0.000 description 2
- PZLGBASBFOSOOX-UHFFFAOYSA-N 6-[2-(4-phthalazin-1-ylpiperazin-1-yl)ethyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=C4NC(OC4=C3)=O)=NN=CC2=C1 PZLGBASBFOSOOX-UHFFFAOYSA-N 0.000 description 2
- ZWSBCAMYZMCUFX-UHFFFAOYSA-N 6-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=C4NC(OC4=C3)=O)=NSC2=C1 ZWSBCAMYZMCUFX-UHFFFAOYSA-N 0.000 description 2
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- QOYUUAUHYUIMDO-UHFFFAOYSA-N ethenyl 4-(2,1,3-benzothiadiazol-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC=C)CCN1C1=CC=CC2=NSN=C12 QOYUUAUHYUIMDO-UHFFFAOYSA-N 0.000 description 2
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- 230000033001 locomotion Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- LWPVQTZPRWKELS-UHFFFAOYSA-N 1-(4-methoxynaphthalen-1-yl)piperazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1N1CCNCC1 LWPVQTZPRWKELS-UHFFFAOYSA-N 0.000 description 1
- FBPPFIPXMJEJCU-UHFFFAOYSA-N 1-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazine Chemical compound C1CCCC2=C1C=CC=C2N1CCNCC1 FBPPFIPXMJEJCU-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8700423 | 1987-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD272077A5 true DD272077A5 (de) | 1989-09-27 |
Family
ID=22202301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88313286A DD272077A5 (de) | 1987-03-02 | 1988-03-01 | Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0281309B1 (cs) |
| JP (1) | JPH0710837B2 (cs) |
| KR (1) | KR900003492B1 (cs) |
| CN (1) | CN1015057B (cs) |
| AR (1) | AR244673A1 (cs) |
| AT (1) | ATE70833T1 (cs) |
| AU (1) | AU583762B2 (cs) |
| BA (1) | BA98296A (cs) |
| CA (1) | CA1300139C (cs) |
| CZ (1) | CZ281257B6 (cs) |
| DD (1) | DD272077A5 (cs) |
| DE (3) | DE10299021I1 (cs) |
| DK (1) | DK173065B1 (cs) |
| EG (1) | EG18398A (cs) |
| ES (1) | ES2040838T3 (cs) |
| FI (1) | FI91868C (cs) |
| GR (1) | GR3003459T3 (cs) |
| HU (1) | HU207860B (cs) |
| IE (1) | IE60849B1 (cs) |
| IL (1) | IL85495A (cs) |
| LU (1) | LU90944I2 (cs) |
| MX (1) | MX173362B (cs) |
| MY (1) | MY103352A (cs) |
| NO (2) | NO170977C (cs) |
| NZ (1) | NZ223694A (cs) |
| PH (1) | PH24119A (cs) |
| PL (1) | PL157897B1 (cs) |
| PT (1) | PT86866B (cs) |
| SU (1) | SU1644716A3 (cs) |
| YU (1) | YU46639B (cs) |
| ZA (1) | ZA881447B (cs) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60130573A (ja) * | 1983-12-15 | 1985-07-12 | Otsuka Pharmaceut Co Ltd | ベンゾチアゾ−ル誘導体 |
| US4720297A (en) * | 1985-09-27 | 1988-01-19 | Sumitomo Chemical Company, Limited | Benzothiazolones, and their production and use as herbicides |
| US4883795A (en) * | 1988-01-22 | 1989-11-28 | Pfizer Inc. | Piperazinyl-heterocyclic compounds |
| FR2631625B1 (fr) * | 1988-05-17 | 1992-10-16 | Synthelabo | Derives de phenyl-6 piperazinylalkyl-3 1h,3h-pyrimidinedione-2,4, leur preparation et leur application en therapeutique |
| US5015740A (en) * | 1988-08-05 | 1991-05-14 | Janssen Pharmaceutica N.V. | Antipsychotic 3-piperazinylbenzazole derivatives |
| US4957916A (en) * | 1988-08-05 | 1990-09-18 | Janssen Pharmaceutica N.V. | Antipsychotic 3-piperazinylbenzazole derivatives |
| US5153206A (en) * | 1988-12-02 | 1992-10-06 | Pfizer Inc. | Arylpiperidine derivatives |
| WO1991000863A1 (en) * | 1989-07-07 | 1991-01-24 | Pfizer Inc. | Heteroaryl piperazine antipsychotic agents |
| EP0429341A3 (en) * | 1989-11-20 | 1991-11-13 | Rhone-Poulenc Sante | Heterocyclic derivatives, their preparation and pharmaceuticals containing them |
| FR2655042B1 (fr) * | 1989-11-29 | 1994-01-21 | Adir Cie | Nouvelles benzothiazolinones substituees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5162321A (en) * | 1989-12-20 | 1992-11-10 | Adir Et Compagnie | 1-naphthyl piperazines useful as 5-HT1A receptor ligands |
| US5166156A (en) * | 1989-12-20 | 1992-11-24 | Adir Et Compagnie | Naphthyl piperazines useful as 5-HT1A receptor ligands |
| US5166157A (en) * | 1989-12-20 | 1992-11-24 | Adir Et Compagnie | Naphthyl piperazines useful as 5-HT1A receptor ligands |
| FR2655988B1 (fr) * | 1989-12-20 | 1994-05-20 | Adir Cie | Nouveaux derives de la napht-1-yl piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5162324A (en) * | 1989-12-20 | 1992-11-10 | Adir Et Compagnie | Naphyl piperazines useful as 5-HT1A receptor ligands |
| FR2671350A1 (fr) * | 1991-01-08 | 1992-07-10 | Adir | Nouveaux derives de benzisoxazole et de benzisothiazole, leur procede de preparation, et les compositions pharmaceutiques les renfermant. |
| US5268381A (en) * | 1990-09-26 | 1993-12-07 | Adir Et Compagnie | Aminoalkyl-benzothiazolinone and -benzoxazolinone compounds having a high 5-HT1A affinity |
| FR2667068B1 (fr) * | 1990-09-26 | 1994-09-09 | Adir | Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5147881A (en) * | 1990-11-14 | 1992-09-15 | Pfizer Inc | 4-(1,2-benzisoxazolyl)piperidine antipsychotic agents |
| US5643784A (en) * | 1990-12-04 | 1997-07-01 | H, Lundbeck A/S | Indan derivatives |
| FR2674524B1 (fr) * | 1991-03-25 | 1993-05-21 | Adir | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| IE914218A1 (en) * | 1991-09-11 | 1993-03-24 | Mcneilab Inc | Novel 4-arylpiperazines and 4-arylpiperidines |
| DK55192D0 (da) * | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
| DK78692D0 (da) * | 1992-06-12 | 1992-06-12 | Lundbeck & Co As H | Dimere piperidin- og piperazinderivater |
| US5312925A (en) * | 1992-09-01 | 1994-05-17 | Pfizer Inc. | Monohydrate of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one-hydrochloride |
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| KR0179063B1 (ko) * | 1993-02-04 | 1999-03-20 | 사사이 아키라 | 항정신병 작용을 갖는 화합물 |
| FR2702214B1 (fr) * | 1993-03-05 | 1995-04-14 | Adir | Nouveaux composés (aryl(alkyl)carbonyl)-hétérocycliques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| GB9305623D0 (en) * | 1993-03-18 | 1993-05-05 | Merck Sharp & Dohme | Therapeutic agents |
| ES2083319B1 (es) * | 1993-09-20 | 1997-01-16 | Pfizer | Monohidrato de clorhidrato de 5-(2-(4-(1,2-benzisotiazol-3-il)-1-piperazinil)-etil)-6-cloro-1,3-dihidro-2h-indol-2-ona. |
| AU687155B2 (en) * | 1994-03-22 | 1998-02-19 | Les Laboratoires Servier | Novel aminoalkyl benzothiazolinones, process for their preparation and the pharmaceutical compositions which contain them |
| FR2717807B1 (fr) * | 1994-03-22 | 1996-04-19 | Adir | Nouvelles 6- [(4-arylalkyl-1-piperazino)alkyl] benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
| IL118768A (en) * | 1995-07-12 | 2000-10-31 | Akzo Nobel Nv | Diphenylmethane piperidine derivatives pharmaceutical compositions containing them and a method for their preparation |
| US6187774B1 (en) * | 1996-03-04 | 2001-02-13 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and pharmaceutical applications thereof |
| UA57734C2 (uk) | 1996-05-07 | 2003-07-15 | Пфайзер Інк. | Комплекси включення арилгетероциклічних солей |
| TW491847B (en) * | 1996-05-07 | 2002-06-21 | Pfizer | Mesylate dihydrate salts of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2h-indol-2-one |
| EP0904273B1 (en) * | 1996-05-07 | 2003-04-09 | Pfizer Inc. | Mesylate trihydrate salt of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2(1h)-indol-2-one (=ziprasidone), its preparation and its use as dopamine d2 antagonist |
| FR2755690B1 (fr) * | 1996-11-08 | 1998-12-18 | Adir | Nouveaux derives aminomethyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6150366A (en) * | 1998-06-15 | 2000-11-21 | Pfizer Inc. | Ziprasidone formulations |
| AR030357A1 (es) * | 2000-08-18 | 2003-08-20 | Lundbeck & Co As H | Derivados 4 -, 5 -, 6 - y 7-indol |
| WO2003007956A1 (en) | 2001-07-20 | 2003-01-30 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
| AU2003233228A1 (en) * | 2002-05-03 | 2003-11-17 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Novel spiro ketone and carboxylic acid derivatives as specific inhibitors for (po3h2) ser/(po3h2)thr-pro-specific peptidyl-prolyl-cis/trans-isomerases |
| JP2006507282A (ja) * | 2002-10-28 | 2006-03-02 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | オキシインドール置換ピペラジン誘導体 |
| CA2625837A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Method for enhancing cognition using ziprasidone |
| JP2007522095A (ja) * | 2003-05-16 | 2007-08-09 | ファイザー・プロダクツ・インク | ジプラシドンを用いた不安の治療 |
| BRPI0410378A (pt) * | 2003-05-16 | 2006-06-13 | Pfizer Prod Inc | tratamento de distúrbios psicóticos e depressivos |
| HUP0400953A3 (en) * | 2004-05-11 | 2008-02-28 | Egis Gyogyszergyar Nyilvanosan | Piperazine derivatives of alkyl-oxindoles, pharmaceutical compositions containing them, process for producing them and their use |
| PL1751106T3 (pl) * | 2004-05-11 | 2009-07-31 | Egis Gyogyszergyar Nyrt | Piperazynowe pochodne alkilooksyindoli |
| US7728136B2 (en) | 2004-06-18 | 2010-06-01 | Lupin Limited | Method for the preparation of aryl piperazinyl-heterocyclic compounds |
| ES2250000B1 (es) * | 2004-09-29 | 2007-06-01 | Medichem, S.A. | Procedimiento para la preparacion de ziprasidona. |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| HUP0600868A3 (en) * | 2006-11-24 | 2009-03-30 | Richter Gedeon Nyrt | 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-6-chloro-1,3-dihydro-2h-indol-2-one hydrogen bromide polimorphs and process for their preparation |
| JO2642B1 (en) | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| JO2849B1 (en) * | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| US8933101B2 (en) | 2007-04-23 | 2015-01-13 | Janssen Pharmaceutica Nv | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| RU2464268C2 (ru) | 2007-04-23 | 2012-10-20 | Янссен Фармацевтика Н.В. | 4-алкоксипиридазиновые производные в качестве быстро диссоциирующихся антагонистов рецептора 2 допамина |
| CA2729313C (en) | 2008-07-03 | 2016-08-30 | Janssen Pharmaceutica Nv | Substituted 6-(1-piperazinyl)-pyridazines as 5-ht6 receptor antagonists |
| CA2730774C (en) | 2008-07-31 | 2016-09-13 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| WO2010151689A1 (en) | 2009-06-25 | 2010-12-29 | Alkermes, Inc. | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| PL391810A1 (pl) | 2010-07-14 | 2012-01-16 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Nowe sole ziprasidonu oraz sposoby ich otrzymywania |
| SI23610A (sl) | 2011-01-13 | 2012-07-31 | Diagen@d@o@o | Nove adicijske soli ziprasidona postopek za njihovo pripravo in njihova uporaba v terapiji |
| EP2919788A4 (en) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR TREATING SCHIZOPHRENIA |
| MA41169A (fr) * | 2014-12-17 | 2017-10-24 | Acraf | Composés antibactériens à large spectre d'activité |
| CN112423754A (zh) | 2018-03-05 | 2021-02-26 | 奥克梅斯制药爱尔兰有限公司 | 阿立哌唑的给药策略 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179505A (en) * | 1977-03-30 | 1979-12-18 | Janssen Pharmaceutica N.V. | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives |
| FR2536749A1 (fr) * | 1982-11-25 | 1984-06-01 | Cerm Cent Europ Rech Mauvernay | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
| US4554284A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | 7-(2-Aminoethyl)-1,3-benzthia- or oxa-zol-2(3H)-ones |
| JPH0625181B2 (ja) * | 1985-03-27 | 1994-04-06 | 住友製薬株式会社 | 新規なイミド誘導体 |
| NL8601494A (nl) * | 1985-06-22 | 1987-01-16 | Sandoz Ag | Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten. |
| JPS6212768A (ja) * | 1985-06-22 | 1987-01-21 | サンド・アクチエンゲゼルシヤフト | 新規チアゾ−ル類、その製法および医薬 |
| MX174210B (es) * | 1987-02-17 | 1994-04-28 | Pfizer | Procedimiento para la preparacion de compuestos arilpiperazinil-alquilenfenil-p-heterociclicos |
-
1987
- 1987-03-02 MX MX1062188A patent/MX173362B/es unknown
-
1988
- 1988-02-22 IL IL85495A patent/IL85495A/xx not_active IP Right Cessation
- 1988-02-24 DE DE2002199021 patent/DE10299021I1/de active Pending
- 1988-02-24 ES ES198888301561T patent/ES2040838T3/es not_active Expired - Lifetime
- 1988-02-24 EP EP88301561A patent/EP0281309B1/en not_active Expired - Lifetime
- 1988-02-24 AT AT88301561T patent/ATE70833T1/de active
- 1988-02-24 DE DE19883867089 patent/DE10299021I2/de active Active
- 1988-02-24 DE DE8888301561T patent/DE3867089D1/de not_active Expired - Lifetime
- 1988-02-29 PT PT86866A patent/PT86866B/pt active IP Right Grant
- 1988-02-29 CA CA000560086A patent/CA1300139C/en not_active Expired - Lifetime
- 1988-03-01 SU SU884355508A patent/SU1644716A3/ru active
- 1988-03-01 ZA ZA881447A patent/ZA881447B/xx unknown
- 1988-03-01 FI FI880941A patent/FI91868C/fi not_active IP Right Cessation
- 1988-03-01 PH PH36572A patent/PH24119A/en unknown
- 1988-03-01 PL PL1988270925A patent/PL157897B1/pl unknown
- 1988-03-01 EG EG115/88A patent/EG18398A/xx active
- 1988-03-01 DD DD88313286A patent/DD272077A5/de unknown
- 1988-03-01 AU AU12537/88A patent/AU583762B2/en not_active Expired
- 1988-03-01 NO NO880901A patent/NO170977C/no not_active IP Right Cessation
- 1988-03-01 IE IE57488A patent/IE60849B1/en not_active IP Right Cessation
- 1988-03-01 YU YU40688A patent/YU46639B/sh unknown
- 1988-03-01 HU HU88976A patent/HU207860B/hu unknown
- 1988-03-01 MY MYPI88000206A patent/MY103352A/en unknown
- 1988-03-01 CZ CS881317A patent/CZ281257B6/cs not_active IP Right Cessation
- 1988-03-01 CN CN88101642A patent/CN1015057B/zh not_active Expired
- 1988-03-01 NZ NZ223694A patent/NZ223694A/xx unknown
- 1988-03-01 DK DK198801083A patent/DK173065B1/da not_active IP Right Cessation
- 1988-03-01 AR AR88310191A patent/AR244673A1/es active
- 1988-03-02 JP JP4945288A patent/JPH0710837B2/ja not_active Expired - Lifetime
- 1988-03-02 KR KR1019880002163A patent/KR900003492B1/ko not_active Expired
-
1991
- 1991-12-30 GR GR91402162T patent/GR3003459T3/el unknown
-
1998
- 1998-03-30 BA BA980296A patent/BA98296A/bs unknown
-
2002
- 2002-05-28 NO NO2002004C patent/NO2002004I2/no unknown
- 2002-08-07 LU LU90944C patent/LU90944I2/fr unknown
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| NPV | Change in the person, the name or the address of the representative (addendum to changes before extension act) | ||
| IF04 | In force in the year 2004 |
Expiry date: 20080302 |