IL127497A - Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders - Google Patents

Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders

Info

Publication number: IL127497A
Authority: IL; Israel
Prior art keywords: disorder; dementia; pharmaceutical composition; composition according; optionally substituted
Prior art date: 1997-12-18

Application number

IL12749798A

Other languages

English (en)

Hebrew (he)

Other versions

IL127497A0 (en

Original Assignee

Pfizer Prod Inc

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.)

1997-12-18

Filing date

1998-12-10

Publication date

2002-07-25

1998-12-10 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

1999-10-28 Publication of IL127497A0 publication Critical patent/IL127497A0/xx

2002-07-25 Publication of IL127497A publication Critical patent/IL127497A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 27
208000020016 psychiatric disease Diseases 0.000 title description 6
-1 benzoisothiazolyl Chemical group 0.000 claims abstract description 48
206010012289 Dementia Diseases 0.000 claims abstract description 45
150000001875 compounds Chemical class 0.000 claims abstract description 40
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 20
208000019901 Anxiety disease Diseases 0.000 claims abstract description 17
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 17
208000028017 Psychotic disease Diseases 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
230000003542 behavioural effect Effects 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
208000012661 Dyskinesia Diseases 0.000 claims abstract description 13
208000036626 Mental retardation Diseases 0.000 claims abstract description 11
208000019022 Mood disease Diseases 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
208000020706 Autistic disease Diseases 0.000 claims abstract description 7
208000027691 Conduct disease Diseases 0.000 claims abstract description 7
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 7
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 6
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000001041 indolyl group Chemical group 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000005493 quinolyl group Chemical group 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract description 4
125000005874 benzothiadiazolyl group Chemical group 0.000 claims abstract description 3
125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 3
125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims abstract description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims abstract description 3
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract 2
206010026749 Mania Diseases 0.000 claims description 11
208000024714 major depressive disease Diseases 0.000 claims description 8
208000020925 Bipolar disease Diseases 0.000 claims description 7
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 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
208000011688 Generalised anxiety disease Diseases 0.000 claims description 6
208000029364 generalized anxiety disease Diseases 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
206010012239 Delusion Diseases 0.000 claims description 5
231100000868 delusion Toxicity 0.000 claims description 5
208000019906 panic disease Diseases 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
206010012374 Depressed mood Diseases 0.000 claims description 4
208000020401 Depressive disease Diseases 0.000 claims description 4
230000000994 depressogenic effect Effects 0.000 claims description 4
230000000306 recurrent effect Effects 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 3
206010065040 AIDS dementia complex Diseases 0.000 claims description 2
208000008811 Agoraphobia Diseases 0.000 claims description 2
208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 2
208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 2
208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 2
201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
208000036769 Mild mental retardation Diseases 0.000 claims description 2
208000036831 Moderate mental retardation Diseases 0.000 claims description 2
206010052794 Panic disorder with agoraphobia Diseases 0.000 claims description 2
206010033668 Panic disorder without agoraphobia Diseases 0.000 claims description 2
208000032991 Profound mental retardation Diseases 0.000 claims description 2
208000036623 Severe mental retardation Diseases 0.000 claims description 2
206010041250 Social phobia Diseases 0.000 claims description 2
208000013200 Stress disease Diseases 0.000 claims description 2
208000031674 Traumatic Acute Stress disease Diseases 0.000 claims description 2
201000004810 Vascular dementia Diseases 0.000 claims description 2
208000026345 acute stress disease Diseases 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
208000026725 cyclothymic disease Diseases 0.000 claims description 2
208000009985 drug-induced dyskinesia Diseases 0.000 claims description 2
230000001505 hypomanic effect Effects 0.000 claims description 2
230000000626 neurodegenerative effect Effects 0.000 claims description 2
230000002085 persistent effect Effects 0.000 claims description 2
208000018726 traumatic encephalopathy Diseases 0.000 claims description 2
201000000980 schizophrenia Diseases 0.000 abstract description 5
208000027465 Psychotic Affective disease Diseases 0.000 abstract description 4
230000036506 anxiety Effects 0.000 abstract description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000003003 spiro group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 62
239000007787 solid Substances 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 42
229910001868 water Inorganic materials 0.000 description 42
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 38
238000000034 method Methods 0.000 description 35
229910052757 nitrogen Inorganic materials 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
239000000047 product Substances 0.000 description 19
229910000029 sodium carbonate Inorganic materials 0.000 description 19
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
239000000203 mixture Substances 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
239000012267 brine Substances 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 12
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 11
238000003756 stirring Methods 0.000 description 11
ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 10
239000003480 eluent Substances 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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 8
229940043265 methyl isobutyl ketone Drugs 0.000 description 8
239000000243 solution Substances 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
241000400611 Eucalyptus deanei Species 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
125000004193 piperazinyl group Chemical group 0.000 description 6
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 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
239000000725 suspension Substances 0.000 description 5
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 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 4
229960000607 ziprasidone Drugs 0.000 description 4
VNICFCQJUVFULD-UHFFFAOYSA-N 1-(1-naphthalenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=CC=CC=C12 VNICFCQJUVFULD-UHFFFAOYSA-N 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010037180 Psychiatric symptoms Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
125000002346 iodo group Chemical group I* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000004770 neurodegeneration Effects 0.000 description 3
208000019899 phobic disease Diseases 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
208000028173 post-traumatic stress disease Diseases 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
208000024891 symptom Diseases 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
LOEVNCQTVTVGKM-UHFFFAOYSA-N 4-(2-oxo-3h-1,3-benzoxazol-6-yl)butyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCCCCC1=CC=C2NC(=O)OC2=C1 LOEVNCQTVTVGKM-UHFFFAOYSA-N 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
JZJFRQGXFVVZPK-UHFFFAOYSA-N 4-piperazin-1-yl-2,1,3-benzothiadiazole Chemical compound C1CNCCN1C1=CC=CC2=NSN=C12 JZJFRQGXFVVZPK-UHFFFAOYSA-N 0.000 description 2
PVABLRWKKBXIDZ-UHFFFAOYSA-N 5-(2-bromoethyl)benzimidazol-2-one Chemical compound C1=C(CCBr)C=CC2=NC(=O)N=C21 PVABLRWKKBXIDZ-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
NZDBKBRIBJLNNT-UHFFFAOYSA-N 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;hydron;chloride Chemical compound Cl.C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 NZDBKBRIBJLNNT-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
CYVQZXCJZRDKLT-UHFFFAOYSA-N 6-(4-chlorobutyl)-3h-1,3-benzoxazol-2-one Chemical compound ClCCCCC1=CC=C2NC(=O)OC2=C1 CYVQZXCJZRDKLT-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
208000024827 Alzheimer disease Diseases 0.000 description 2
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
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WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
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238000007918 intramuscular administration Methods 0.000 description 2
239000008101 lactose Substances 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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000004885 piperazines Chemical class 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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 2
229950001675 spiperone Drugs 0.000 description 2
FGHVSEXHEAUJBT-HFNHQGOYSA-N (z)-but-2-enedioic acid;(5r)-8-chloro-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound OC(=O)\C=C/C(O)=O.C1([C@@H]2C3=CC(O)=C(Cl)C=C3CCN(C2)C)=CC=CC=C1 FGHVSEXHEAUJBT-HFNHQGOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
DRLGIZIAMHIQHL-UHFFFAOYSA-N 2,1,3-benzothiadiazol-4-amine Chemical compound NC1=CC=CC2=NSN=C12 DRLGIZIAMHIQHL-UHFFFAOYSA-N 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
HACZVIMLSOTUBM-UHFFFAOYSA-N 2-naphthalen-1-ylpiperazine Chemical compound C1NCCNC1C1=CC=CC2=CC=CC=C12 HACZVIMLSOTUBM-UHFFFAOYSA-N 0.000 description 1
WAOQONBSWFLFPE-VIFPVBQESA-N 3,5-dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(Cl)=CC(Cl)=C1OC WAOQONBSWFLFPE-VIFPVBQESA-N 0.000 description 1
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Classifications

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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A—HUMAN NECESSITIES
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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IL12749798A 1997-12-18 1998-12-10 Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders IL127497A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6806997P	1997-12-18	1997-12-18

Publications (2)

Publication Number	Publication Date
IL127497A0 IL127497A0 (en)	1999-10-28
IL127497A true IL127497A (en)	2002-07-25

Family

ID=22080230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12749798A IL127497A (en)	1997-12-18	1998-12-10	Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders

Country Status (16)

Country	Link
US (1)	US6245766B1 (zh)
EP (1)	EP0931547B1 (zh)
JP (1)	JPH11246409A (zh)
KR (1)	KR19990066852A (zh)
AT (1)	ATE231394T1 (zh)
AU (1)	AU739472B2 (zh)
CA (1)	CA2256227C (zh)
DE (1)	DE69810889T2 (zh)
DK (1)	DK0931547T3 (zh)
ES (1)	ES2190570T3 (zh)
HU (1)	HUP9802958A1 (zh)
IL (1)	IL127497A (zh)
MY (1)	MY121036A (zh)
NZ (1)	NZ333436A (zh)
TW (1)	TW520989B (zh)
ZA (1)	ZA9811573B (zh)

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EP1633400A2 (en)	2003-05-16	2006-03-15	Pfizer Products Inc.	Therapeutic combinations of atypical antipsychotics with gaba modulators, anticonvulsants or benzodiazapines
BRPI0419067A (pt) *	2003-05-16	2007-12-11	Pfizer Prod Inc	método para aumento da cognição utilizando ziprasidona
WO2004100957A1 (en) *	2003-05-16	2004-11-25	Pfizer Products Inc.	Treatment of bipolar disorders and associated symptoms
CA2525866A1 (en) *	2003-05-16	2004-11-25	Pfizer Products Inc.	Treatment of psychotic and depressive disorders
EP1633361A1 (en) *	2003-05-16	2006-03-15	Pfizer Products Inc.	Anxiety treatments with ziprasidone
US8097606B2 (en) *	2003-07-23	2012-01-17	Corcept Therapeutics, Inc.	Antiglucocorticoids for the treatment of catatonia
AR045362A1 (es) *	2003-08-18	2005-10-26	Solvay Pharm Bv	Forma cristalina estable de mesilato de bifeprunox (monometansulfonato de 7-[4-([1,1- bifenil] -3- ilmetil) -1- piperazinil] - 2-(3h) -benzoxazolona
CA2553207A1 (en) *	2004-01-13	2005-08-04	Kishore M. Gadde	Compositions of an anticonvulsant and an antipsychotic drug for affecting weight loss
US7713959B2 (en) *	2004-01-13	2010-05-11	Duke University	Compositions of an anticonvulsant and mirtazapine to prevent weight gain
CA2556160A1 (en) *	2004-02-13	2005-09-01	Pfizer Products Inc.	Therapeutic combinations of atypical antipsychotics with corticotropin releasing factor antagonists
BRPI0510593A (pt) *	2004-05-03	2007-11-20	Univ Duke	composições para afetar a perda de peso
WO2005107808A2 (en) *	2004-05-11	2005-11-17	Pfizer Products Inc.	Combination of atypical antipsychotics and 5-ht1b receptor antagonists
EP2623095A1 (en) *	2004-11-16	2013-08-07	Elan Pharma International Limited	Injectable nanoparticulate olanzapine formulations
WO2006096462A1 (en) *	2005-03-03	2006-09-14	Elan Pharma International Limited	Nanoparticulate compositions of heterocyclic amide derivatives
GT200600161A (es) *	2005-04-22	2007-03-14		Nuevas combinaciones terapeuticas para el tratamiento o la prevencion de los trastornos psicoticos
PL2135603T3 (pl)	2005-11-22	2013-09-30	Orexigen Therapeutics Inc	Kompozycje i sposoby zwiększania wrażliwości na insulinę
US8916195B2 (en)	2006-06-05	2014-12-23	Orexigen Therapeutics, Inc.	Sustained release formulation of naltrexone
US20080004260A1 (en) *	2006-06-29	2008-01-03	Transcept Pharmaceuticals, Inc.	Compositions of 5-HT3 antagonists and dopamine D2 antagonists for treatment of dopamine-associated chronic conditions
WO2008060963A2 (en)	2006-11-09	2008-05-22	Orexigen Therapeutics, Inc.	Layered pharmaceutical formulations comprising an intermediate rapidly dissolving layer
MX343867B (es)	2006-11-09	2016-11-25	Orexigen Therapeutics Inc	Paquete de dosificacion unitaria y metodos para administrar medicaciones de perdida de peso.
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
EP2303025A4 (en)	2008-05-30	2012-07-04	Orexigen Therapeutics Inc	METHOD FOR TREATING DIGITAL FAT SWITCHES
US20100298397A1 (en) *	2009-05-19	2010-11-25	Singh Nikhilesh N	Method of treatment of obsessive compulsive disorder with ondansetron
BR112012016783A2 (pt)	2010-01-11	2015-09-01	Orexigen Therapeutics Inc	"usos do composto de naltrexona ou sal farmaceuticamente aceitável da mesma a bupropiona ou sal farmaceuticamente aceitável da mesma ou de composição dos mesmos e métodos para proporcionar terapia"
KR20240090733A (ko)	2012-06-06	2024-06-21	오렉시젠 세러퓨틱스 인크.	과체중 및 비만의 치료 방법
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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
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1998
- 1998-12-10 IL IL12749798A patent/IL127497A/en not_active IP Right Cessation
- 1998-12-15 TW TW087120864A patent/TW520989B/zh not_active IP Right Cessation
- 1998-12-15 DK DK98310295T patent/DK0931547T3/da active
- 1998-12-15 DE DE69810889T patent/DE69810889T2/de not_active Expired - Fee Related
- 1998-12-15 AT AT98310295T patent/ATE231394T1/de not_active IP Right Cessation
- 1998-12-15 EP EP98310295A patent/EP0931547B1/en not_active Expired - Lifetime
- 1998-12-15 ES ES98310295T patent/ES2190570T3/es not_active Expired - Lifetime
- 1998-12-16 MY MYPI98005693A patent/MY121036A/en unknown
- 1998-12-16 CA CA002256227A patent/CA2256227C/en not_active Expired - Lifetime
- 1998-12-17 AU AU97170/98A patent/AU739472B2/en not_active Ceased
- 1998-12-17 NZ NZ333436A patent/NZ333436A/en unknown
- 1998-12-17 ZA ZA9811573A patent/ZA9811573B/xx unknown
- 1998-12-17 HU HU9802958A patent/HUP9802958A1/hu unknown
- 1998-12-18 JP JP10360410A patent/JPH11246409A/ja active Pending
- 1998-12-18 KR KR1019980056095A patent/KR19990066852A/ko active Search and Examination
- 1998-12-18 US US09/216,334 patent/US6245766B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2256227A1 (en)	1999-06-18
EP0931547A1 (en)	1999-07-28
AU739472B2 (en)	2001-10-11
HU9802958D0 (en)	1999-02-01
EP0931547B1 (en)	2003-01-22
JPH11246409A (ja)	1999-09-14
ZA9811573B (en)	2000-06-19
HUP9802958A1 (hu)	2000-03-28
AU9717098A (en)	1999-07-08
DE69810889D1 (de)	2003-02-27
IL127497A0 (en)	1999-10-28
DE69810889T2 (de)	2003-05-15
US6245766B1 (en)	2001-06-12
ES2190570T3 (es)	2003-08-01
KR19990066852A (ko)	1999-08-16
DK0931547T3 (da)	2003-02-24
TW520989B (en)	2003-02-21
ATE231394T1 (de)	2003-02-15
CA2256227C (en)	2003-07-01
MY121036A (en)	2005-12-30
NZ333436A (en)	2000-06-23

Publication	Publication Date	Title
US6245766B1 (en)	2001-06-12	Method of treating psychiatric conditions
US4831031A (en)	1989-05-16	Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity
US20080269246A1 (en)	2008-10-30	Method for treating pediatric bipolar disorder
US4883795A (en)	1989-11-28	Piperazinyl-heterocyclic compounds
WO2004100954A1 (en)	2004-11-25	Treatment of psychotic and depressive disorders
US20050038036A1 (en)	2005-02-17	Treatment of bipolar disorders and associated symptoms
CA2525868A1 (en)	2004-11-25	Anxiety treatments with ziprasidone
US6387904B2 (en)	2002-05-14	Method of treating glaucoma and ischemic retinopathy
US6127373A (en)	2000-10-03	Method of treating tourette's syndrome and obsessive compulsive disorder
EP0985414B1 (en)	2003-08-27	Medicament for the treatment of glaucoma and ischemic retinopathy
EP1757292A1 (en)	2007-02-28	Method of treating ocd and tic disorders
NZ504733A (en)	2001-11-30	Method of treating tic disorders in non-human mammals

Legal Events

Date	Code	Title
2003-01-12	FF	Patent granted
2003-02-12	KB	Patent renewed
2005-09-25	MM9K	Patent not in force due to non-payment of renewal fees