DD272077A5 - Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen - Google Patents

Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen Download PDF

Info

Publication number: DD272077A5
Authority: DD; German Democratic Republic
Prior art keywords: mmol; ethyl acetate; piperazinyl; evaporated; ethyl
Prior art date: 1987-03-02

Application number

DD88313286A

Other languages

German (de)

English (en)

Inventor

Iii John A Lowe

Arthur A Nagel

Original Assignee

��@��Kk��

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.)

1987-03-02

Filing date

1988-03-01

Publication date

1989-09-27

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22202301&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD272077(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-03-01 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1989-09-27 Publication of DD272077A5 publication Critical patent/DD272077A5/de

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
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239000011541 reaction mixture Substances 0.000 description 37
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
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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
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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
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238000004458 analytical method Methods 0.000 description 14
239000012267 brine Substances 0.000 description 14
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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
CPLWKJWNQCWKQV-UHFFFAOYSA-N 6-(2-bromoethyl)-3h-1,3-benzoxazol-2-one Chemical compound BrCCC1=CC=C2NC(=O)OC2=C1 CPLWKJWNQCWKQV-UHFFFAOYSA-N 0.000 description 10
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
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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
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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
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239000004480 active ingredient Substances 0.000 description 4
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230000003197 catalytic effect Effects 0.000 description 4
125000005999 2-bromoethyl group Chemical group 0.000 description 3
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238000006243 chemical reaction Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000000701 neuroleptic effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000008194 pharmaceutical composition Substances 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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OLHPDERTOIKVER-UHFFFAOYSA-N 5-[2-(4-naphthalen-1-ylpiperazin-1-yl)ethyl]benzimidazol-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=CC4=NC(N=C4C=3)=O)=CC=CC2=C1 OLHPDERTOIKVER-UHFFFAOYSA-N 0.000 description 2
LTKOVYPSNBPPDB-UHFFFAOYSA-N 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-1,3-dihydroindol-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4CC(NC4=CC=3)=O)=NSC2=C1 LTKOVYPSNBPPDB-UHFFFAOYSA-N 0.000 description 2
IMMWCMHVIKCYSW-UHFFFAOYSA-N 6-(4-bromobutanoyl)-3h-1,3-benzoxazol-2-one Chemical compound BrCCCC(=O)C1=CC=C2NC(=O)OC2=C1 IMMWCMHVIKCYSW-UHFFFAOYSA-N 0.000 description 2
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
OUOBVBYOAFEOKS-UHFFFAOYSA-N 6-fluoronaphthalen-1-amine Chemical compound FC1=CC=C2C(N)=CC=CC2=C1 OUOBVBYOAFEOKS-UHFFFAOYSA-N 0.000 description 2
PRGBEFGWVMWEGQ-UHFFFAOYSA-N 6-fluoronaphthalene-1-carboxylic acid Chemical compound FC1=CC=C2C(C(=O)O)=CC=CC2=C1 PRGBEFGWVMWEGQ-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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239000008101 lactose Substances 0.000 description 2
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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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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238000010898 silica gel chromatography Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
CRVNOUFSHGQXRN-UHFFFAOYSA-N 1,3-dihydroindol-2-one hydrate hydrochloride Chemical compound O.Cl.C1=CC=C2NC(=O)CC2=C1 CRVNOUFSHGQXRN-UHFFFAOYSA-N 0.000 description 1
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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Quinoline Compounds (AREA)

DD88313286A 1987-03-02 1988-03-01 Verfahren zur herstellung von piperazinyl-heterocyclischen verbindungen DD272077A5 (de)

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 (bs)
JP (1)	JPH0710837B2 (bs)
KR (1)	KR900003492B1 (bs)
CN (1)	CN1015057B (bs)
AR (1)	AR244673A1 (bs)
AT (1)	ATE70833T1 (bs)
AU (1)	AU583762B2 (bs)
BA (1)	BA98296A (bs)
CA (1)	CA1300139C (bs)
CZ (1)	CZ281257B6 (bs)
DD (1)	DD272077A5 (bs)
DE (3)	DE10299021I1 (bs)
DK (1)	DK173065B1 (bs)
EG (1)	EG18398A (bs)
ES (1)	ES2040838T3 (bs)
FI (1)	FI91868C (bs)
GR (1)	GR3003459T3 (bs)
HU (1)	HU207860B (bs)
IE (1)	IE60849B1 (bs)
IL (1)	IL85495A (bs)
LU (1)	LU90944I2 (bs)
MX (1)	MX173362B (bs)
MY (1)	MY103352A (bs)
NO (2)	NO170977C (bs)
NZ (1)	NZ223694A (bs)
PH (1)	PH24119A (bs)
PL (1)	PL157897B1 (bs)
PT (1)	PT86866B (bs)
SU (1)	SU1644716A3 (bs)
YU (1)	YU46639B (bs)
ZA (1)	ZA881447B (bs)

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DK148392D0 (da) *	1992-12-09	1992-12-09	Lundbeck & Co As H	Heterocykliske forbindelser
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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.
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AR030357A1 (es)	2000-08-18	2003-08-20	Lundbeck & Co As H	Derivados 4 -, 5 -, 6 - y 7-indol
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JO2642B1 (en)	2006-12-08	2012-06-17	جانسين فارماسوتيكا ان. في	Dopamine 2 receptor antagonists are rapidly hydrolyzed
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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 EP EP88301561A patent/EP0281309B1/en not_active Expired - Lifetime
- 1988-02-24 DE DE2002199021 patent/DE10299021I1/de active Pending
- 1988-02-24 DE DE19883867089 patent/DE10299021I2/de active Active
- 1988-02-24 DE DE8888301561T patent/DE3867089D1/de not_active Expired - Lifetime
- 1988-02-24 AT AT88301561T patent/ATE70833T1/de active
- 1988-02-24 ES ES198888301561T patent/ES2040838T3/es not_active Expired - Lifetime
- 1988-02-29 CA CA000560086A patent/CA1300139C/en not_active Expired - Lifetime
- 1988-02-29 PT PT86866A patent/PT86866B/pt active IP Right Grant
- 1988-03-01 MY MYPI88000206A patent/MY103352A/en unknown
- 1988-03-01 EG EG115/88A patent/EG18398A/xx active
- 1988-03-01 AU AU12537/88A patent/AU583762B2/en not_active Expired
- 1988-03-01 NZ NZ223694A patent/NZ223694A/xx unknown
- 1988-03-01 PH PH36572A patent/PH24119A/en unknown
- 1988-03-01 CN CN88101642A patent/CN1015057B/zh not_active Expired
- 1988-03-01 YU YU40688A patent/YU46639B/sh unknown
- 1988-03-01 NO NO880901A patent/NO170977C/no not_active IP Right Cessation
- 1988-03-01 HU HU88976A patent/HU207860B/hu unknown
- 1988-03-01 AR AR88310191A patent/AR244673A1/es active
- 1988-03-01 ZA ZA881447A patent/ZA881447B/xx unknown
- 1988-03-01 DK DK198801083A patent/DK173065B1/da not_active IP Right Cessation
- 1988-03-01 PL PL1988270925A patent/PL157897B1/pl unknown
- 1988-03-01 DD DD88313286A patent/DD272077A5/de unknown
- 1988-03-01 FI FI880941A patent/FI91868C/fi not_active IP Right Cessation
- 1988-03-01 CZ CS881317A patent/CZ281257B6/cs not_active IP Right Cessation
- 1988-03-01 IE IE57488A patent/IE60849B1/en not_active IP Right Cessation
- 1988-03-01 SU SU884355508A patent/SU1644716A3/ru active
- 1988-03-02 KR KR1019880002163A patent/KR900003492B1/ko not_active Expired
- 1988-03-02 JP JP4945288A patent/JPH0710837B2/ja not_active Expired - Lifetime
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

Also Published As

Publication number	Publication date
EP0281309B1 (en)	1991-12-27
JPH0710837B2 (ja)	1995-02-08
PT86866B (pt)	1992-05-29
NO2002004I2 (no)	2007-02-12
NO170977C (no)	1993-01-06
DE10299021I1 (de)	2002-09-26
ZA881447B (en)	1989-10-25
PL270925A1 (en)	1988-12-08
LU90944I2 (fr)	2002-10-07
CZ281257B6 (cs)	1996-07-17
FI91868C (fi)	1994-08-25
DK108388A (da)	1988-09-03
HUT50330A (en)	1990-01-29
ATE70833T1 (de)	1992-01-15
AU1253788A (en)	1988-09-01
MY103352A (en)	1993-06-30
GR3003459T3 (en)	1993-02-17
EG18398A (en)	1993-02-28
CZ131788A3 (en)	1996-05-15
MX10621A (es)	1993-09-01
KR880011142A (ko)	1988-10-26
DK108388D0 (da)	1988-03-01
FI880941A7 (fi)	1988-09-03
IL85495A0 (en)	1988-07-31
CA1300139C (en)	1992-05-05
YU40688A (en)	1989-12-31
IE880574L (en)	1988-09-02
DE10299021I2 (de)	2007-05-10
FI91868B (fi)	1994-05-13
NO880901L (no)	1988-09-05
DK173065B1 (da)	1999-12-13
AU583762B2 (en)	1989-05-04
HU207860B (en)	1993-06-28
YU46639B (sh)	1994-01-20
NO170977B (no)	1992-09-28
CN88101642A (zh)	1988-09-14
CN1015057B (zh)	1991-12-11
ES2040838T3 (es)	1993-11-01
IE60849B1 (en)	1994-08-24
JPS63301861A (ja)	1988-12-08
BA98296A (bs)	2001-09-14
NZ223694A (en)	1990-02-26
PL157897B1 (pl)	1992-07-31
EP0281309A1 (en)	1988-09-07
MX173362B (es)	1994-02-23
IL85495A (en)	1993-05-13
FI880941A0 (fi)	1988-03-01
PH24119A (en)	1990-03-05
SU1644716A3 (ru)	1991-04-23
DE3867089D1 (de)	1992-02-06
KR900003492B1 (ko)	1990-05-21
AR244673A1 (es)	1993-11-30
PT86866A (pt)	1988-03-01
NO880901D0 (no)	1988-03-01

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)
2004-04-28	IF04	In force in the year 2004	Expiry date: 20080302

Publication	Publication Date	Title
EP0281309B1 (en)	1991-12-27	Piperazinyl-heterocyclic compounds
DE69810889T2 (de)	2003-05-15	Heterozyklische Piperazinyl Verbindungen zur Behandlung von Demenz
US4831031A (en)	1989-05-16	Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity
US4883795A (en)	1989-11-28	Piperazinyl-heterocyclic compounds
DE69013836T2 (de)	1995-03-23	Benzimidazolverbindungen und deren Anwendung.
DE69013601T2 (de)	1995-03-02	Heteroaryl Piperazine als antipsychotische Mittel.
DE69128231T2 (de)	1998-06-18	Heterozyklische Alkylamine, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten
DE69434020T2 (de)	2005-09-29	Verfahren und zwischenprodukte für die herstellung von 5-[4-(benzisothiazol-3-yl)-piperazin-1-yl)ethyl]-6 chlor-1,3-dihydro-indol-2-one
DE2309160A1 (de)	1973-09-27	2-imidazolin-2-yl-amino-substituierte, benzokondensierte, heterocyclische verbindungen und arzneipraeparate
EP0006506B1 (de)	1981-09-16	1,2-Dihydro-chinolin-2-on-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
EP0129128A2 (de)	1984-12-27	2-Pyrimidinyl-l-piperazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
JPH06502639A (ja)	1994-03-24	特定のイミダゾキノキサリン；新種のｇａｂａ脳受容体リガンド
DE4031287A1 (de)	1992-04-09	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
JP2006528236A (ja)	2006-12-14	ジプラシドンを用いて認知を増強する方法
JPS5879983A (ja)	1983-05-13	新規なベンズイミダゾ−ル誘導体、その製造法およびその医薬組成物
DE3884007T2 (de)	1994-01-20	Arylpiperazinylalkylenphenylheterocyclische Verbindungen.
CH622793A5 (bs)	1981-04-30
DE69836783T2 (de)	2007-10-31	Methode zur Behandlung des Tourette-Syndroms
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DE60202969T2 (de)	2006-01-19	Substituierte alkylaminopyridazinonderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
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