CA2117304A1 - Composes chimiques, leur preparation et leur utilisation - Google Patents

Composes chimiques, leur preparation et leur utilisation

Info

Publication number: CA2117304A1
Authority: CA; Canada
Prior art keywords: fluoro; piperidine; benzisoxazol; propyl; compound
Prior art date: 1991-11-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002117304A

Other languages

English (en)

Inventor

John Bondo Hansen

Lone Jeppesen

Frederik Christian Gronvald

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novo Nordisk AS

Original Assignee

Individual

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.)

1991-11-27

Filing date

1992-11-25

Publication date

1993-06-10

1992-11-25 Application filed by Individual filed Critical Individual

1993-06-10 Publication of CA2117304A1 publication Critical patent/CA2117304A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 69
238000002360 preparation method Methods 0.000 title claims description 7
238000000034 method Methods 0.000 claims abstract description 34
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 82
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 12
-1 1-[2(3,4-Methylenedioxyphenylcarbamoyloxy)hexyl]-4-(6-fluoro-1,2-benz-isoxazol-3-yl)piperidine Chemical compound 0.000 claims description 9
208000028017 Psychotic disease Diseases 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
DXWPMYXPMOCYKH-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl n-(3,4,5-trimethoxyphenyl)carbamate Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)OCCN2CCC(CC2)C=2C3=CC=C(F)C=C3ON=2)=C1 DXWPMYXPMOCYKH-UHFFFAOYSA-N 0.000 claims description 3
GYGUWRJKLIJBQP-UHFFFAOYSA-N 3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl n-(1,3-benzodioxol-5-yl)carbamate;hydrochloride Chemical compound Cl.C1=C2OCOC2=CC(NC(=O)OCCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 GYGUWRJKLIJBQP-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
FEMMYYYIAIBEEF-UHFFFAOYSA-N 1-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propan-2-yl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound C1=C2OCOC2=CC(NC(=O)OC(CN2CCC(CC2)C=2C3=CC=C(F)C=C3ON=2)C)=C1 FEMMYYYIAIBEEF-UHFFFAOYSA-N 0.000 claims description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
AUFKLCAONSOPPI-UHFFFAOYSA-N 1-[4-(6-fluoro-2h-indazol-3-yl)piperidin-1-yl]propan-2-yl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound C1=C2OCOC2=CC(NC(=O)OC(CN2CCC(CC2)C=2C3=CC=C(F)C=C3NN=2)C)=C1 AUFKLCAONSOPPI-UHFFFAOYSA-N 0.000 claims 1
XHKWBNIAXJYXAD-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound C1=C2OCOC2=CC(NC(=O)OCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 XHKWBNIAXJYXAD-UHFFFAOYSA-N 0.000 claims 1
BTBJXOBAZNUVMO-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl n-(1,3-benzothiazol-6-yl)carbamate Chemical compound C1=C2N=CSC2=CC(NC(=O)OCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 BTBJXOBAZNUVMO-UHFFFAOYSA-N 0.000 claims 1
NBDMFWDPDDEWCU-UHFFFAOYSA-N 3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl n-(1,3-benzothiazol-6-yl)carbamate Chemical compound C1=C2N=CSC2=CC(NC(=O)OCCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 NBDMFWDPDDEWCU-UHFFFAOYSA-N 0.000 claims 1
BJFXGZZAVIAPDA-UHFFFAOYSA-N 3-[4-(6-fluoro-2h-indazol-3-yl)piperidin-1-yl]propyl n-(1,3-benzodioxol-5-yl)carbamate Chemical compound C1=C2OCOC2=CC(NC(=O)OCCCN2CCC(CC2)C=2C3=CC=C(C=C3NN=2)F)=C1 BJFXGZZAVIAPDA-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
WTBQMNSYFKJCKK-UHFFFAOYSA-N o-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propyl] n-(1,3-benzothiazol-6-yl)carbamothioate Chemical compound C1=C2N=CSC2=CC(NC(=S)OCCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 WTBQMNSYFKJCKK-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
150000003053 piperidines Chemical class 0.000 abstract description 5
208000018522 Gastrointestinal disease Diseases 0.000 abstract description 2
210000000748 cardiovascular system Anatomy 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
229910001868 water Inorganic materials 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000000126 substance Substances 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 24
238000012360 testing method Methods 0.000 description 23
239000000872 buffer Substances 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 11
238000011534 incubation Methods 0.000 description 10
108020003175 receptors Proteins 0.000 description 10
102000005962 receptors Human genes 0.000 description 10
210000001519 tissue Anatomy 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
230000027455 binding Effects 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
210000004379 membrane Anatomy 0.000 description 8
239000012528 membrane Chemical group 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
238000003556 assay Methods 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
239000012634 fragment Substances 0.000 description 7
239000003446 ligand Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
229960003638 dopamine Drugs 0.000 description 6
229960004756 ethanol Drugs 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
GTTXYMVUACJZRG-UHFFFAOYSA-N 5-isocyanato-1,3-benzodioxole Chemical compound O=C=NC1=CC=C2OCOC2=C1 GTTXYMVUACJZRG-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
210000001577 neostriatum Anatomy 0.000 description 5
239000008188 pellet Substances 0.000 description 5
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
238000005303 weighing Methods 0.000 description 5
UMNKDRAGADXPKA-UHFFFAOYSA-N 3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCC1C1=NOC2=CC(F)=CC=C12 UMNKDRAGADXPKA-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229940035676 analgesics Drugs 0.000 description 4
239000000730 antalgic agent Substances 0.000 description 4
230000008859 change Effects 0.000 description 4
238000011109 contamination Methods 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000003203 everyday effect Effects 0.000 description 4
239000003517 fume Substances 0.000 description 4
238000000265 homogenisation Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000009870 specific binding Effects 0.000 description 4
239000011550 stock solution Substances 0.000 description 4
VRBSAMVOYMTTQE-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C1=NOC2=CC(F)=CC=C12 VRBSAMVOYMTTQE-UHFFFAOYSA-N 0.000 description 3
MRMGJMGHPJZSAE-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C1CCNCC1 MRMGJMGHPJZSAE-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000700157 Rattus norvegicus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
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238000005119 centrifugation Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
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VEIWYFRREFUNRC-UHFFFAOYSA-N hydron;piperidine;chloride Chemical compound [Cl-].C1CC[NH2+]CC1 VEIWYFRREFUNRC-UHFFFAOYSA-N 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 3
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ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
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XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 2
BZKOZYWGZKRTIB-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-amine Chemical compound O1CCOC2=CC(N)=CC=C21 BZKOZYWGZKRTIB-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
XEFRNCLPPFDWAC-UHFFFAOYSA-N 3,4,5-trimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1OC XEFRNCLPPFDWAC-UHFFFAOYSA-N 0.000 description 2
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 2
JSTUWLQAEUDQKA-UHFFFAOYSA-N 3-[4-(6-fluoro-2h-indazol-3-yl)piperidin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCC1C1=NNC2=CC(F)=CC=C12 JSTUWLQAEUDQKA-UHFFFAOYSA-N 0.000 description 2
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QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 2
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FAYAYUOZWYJNBD-UHFFFAOYSA-N 1,3-benzothiazol-6-amine Chemical compound NC1=CC=C2N=CSC2=C1 FAYAYUOZWYJNBD-UHFFFAOYSA-N 0.000 description 1
FNFSGNTUEYBHKB-UHFFFAOYSA-N 1-isocyanato-2,3,4-trimethoxybenzene Chemical compound COC1=CC=C(N=C=O)C(OC)=C1OC FNFSGNTUEYBHKB-UHFFFAOYSA-N 0.000 description 1
LEZOOXQOFRGIEW-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl n-(1,3-benzoxazol-6-yl)carbamate Chemical compound C1=C2N=COC2=CC(NC(=O)OCCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)=C1 LEZOOXQOFRGIEW-UHFFFAOYSA-N 0.000 description 1
XYRDQHNCDBDNSF-UHFFFAOYSA-N 2-chloro-4-isocyanato-1-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1Cl XYRDQHNCDBDNSF-UHFFFAOYSA-N 0.000 description 1
ZHMWZFCYUILOKB-UHFFFAOYSA-N 3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propan-1-amine Chemical compound C1CN(CCCN)CCC1C1=NOC2=CC(F)=CC=C12 ZHMWZFCYUILOKB-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CA002117304A 1991-11-27 1992-11-25 Composes chimiques, leur preparation et leur utilisation Abandoned CA2117304A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
WOPCT/DK91/00354		1991-11-27
DK9100354		1991-11-27
DK0710/92		1992-05-27
DK71092A DK71092D0 (da)	1992-05-27	1992-05-27	Kemiske forbindelser, deres fremstilling og anvendelse

Publications (1)

Publication Number	Publication Date
CA2117304A1 true CA2117304A1 (fr)	1993-06-10

Family

ID=8096649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002117304A Abandoned CA2117304A1 (fr)	1991-11-27	1992-11-25	Composes chimiques, leur preparation et leur utilisation

Country Status (5)

Country	Link
EP (1)	EP0679085A1 (fr)
CA (1)	CA2117304A1 (fr)
DK (1)	DK71092D0 (fr)
IL (1)	IL103845A (fr)
NO (1)	NO300684B1 (fr)

1992
- 1992-05-27 DK DK71092A patent/DK71092D0/da not_active Application Discontinuation
- 1992-11-23 IL IL10384592A patent/IL103845A/xx not_active IP Right Cessation
- 1992-11-25 CA CA002117304A patent/CA2117304A1/fr not_active Abandoned
- 1992-11-25 EP EP92924586A patent/EP0679085A1/fr not_active Withdrawn
1994
- 1994-05-26 NO NO941965A patent/NO300684B1/no unknown

Also Published As

Publication number	Publication date
NO941965D0 (no)	1994-05-26
EP0679085A1 (fr)	1995-11-02
NO941965L (no)	1994-07-26
IL103845A (en)	1997-02-18
NO300684B1 (no)	1997-07-07
DK71092D0 (da)	1992-05-27

Publication	Publication Date	Title
EP0544756B1 (fr)	1997-11-05	Tetrahydro-1,2,5,6-methyl-1-pyridines, leur preparation et leur utilisation
EP0135781B1 (fr)	1989-10-11	(Pipéridinyl)-3 et (pyrrolidinyl)-3-1H-indazoles, procédé pour leur préparation et leur application en tant que médicaments
RU2042676C1 (ru)	1995-08-27	3-(1,2,5-оксадиазол-3-ил)-или 3-(1,2,5-тиадиазол-3-ил)-1,2,5,6-тетрагидропиридиновые производные или их фармацевтически приемлемые соли, и фармацевтическая композиция, проявляющая мускариновую холинергическую рецепторную агонистическую активность
US4670447A (en)	1987-06-02	Antipsychotic 3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles
EP0544765B1 (fr)	1995-08-02	Dérivés de pipérazinyle avec affinité pour les récepteurs 5-HT
AU672182B2 (en)	1996-09-26	Piperidine derivatives and their use in treating psychosis
EP0127167A2 (fr)	1984-12-05	3-(4-Piperidinyl)-1,2-benzisothiazoles et leurs dérivés, leur procédé de préparation et utilisation comme médicaments
CA2354606C (fr)	2005-12-06	Derives d'azabicycloalkane et utilisations therapeutiques connexes
US4775761A (en)	1988-10-04	3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles
EP2313394A1 (fr)	2011-04-27	Nouveaux dérivés de la pipéridine à substitution par un tétraméthyle et leur utilisation comme inhibiteurs de la recapture des neurotransmetteurs de monoamine
US4608374A (en)	1986-08-26	11-substituted 5H,11H-pyrrolo[2,1-c][1,4]benzoxazepines as antipsychotic and analgesic agents
WO1994027991A1 (fr)	1994-12-08	Derives de piperidine, leur preparation et leur utilisation
US5378714A (en)	1995-01-03	Antipsychotic piperidine derivatives
US5478845A (en)	1995-12-26	Piperidine derivatives
US4806649A (en)	1989-02-21	3-(piperidinyl)- and 3- (pyrrolidinyl)-1H-indazoles
US5789425A (en)	1998-08-04	Imidazolidinone derivatives, their acid adducts and therapeutic drugs for senile dementia
US4853470A (en)	1989-08-01	3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles
US4710573A (en)	1987-12-01	3-(piperidinyl)-and 3-(pyrrolidinyl)-1H-indazoles
CA2117304A1 (fr)	1993-06-10	Composes chimiques, leur preparation et leur utilisation
US6750231B2 (en)	2004-06-15	4-arylpiperidine derivatives for the treatment of pruritus
US4758668A (en)	1988-07-19	3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles
WO1994027996A1 (fr)	1994-12-08	Derives de 1,2,5-thiadiazole, leur preparation et leur utilisation
US5166341A (en)	1992-11-24	6-amino-1,4-hexahydro-1H-diazepine derivatives
US4003904A (en)	1977-01-18	Anti-diarrheal oxadiazoles
EP0285032A1 (fr)	1988-10-05	Composés phényl-4 pipéridiniques, leur préparation et leur application

Legal Events

Date	Code	Title	Description
1999-11-25	FZDE	Discontinued
2023-10-24	FZDE	Discontinued	Effective date: 19991125