NO311617B1 - Kondenserte benzoforbindelser - Google Patents
Kondenserte benzoforbindelser Download PDFInfo
- Publication number
- NO311617B1 NO311617B1 NO19952275A NO952275A NO311617B1 NO 311617 B1 NO311617 B1 NO 311617B1 NO 19952275 A NO19952275 A NO 19952275A NO 952275 A NO952275 A NO 952275A NO 311617 B1 NO311617 B1 NO 311617B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- alkyl
- phenyl
- hydrogen
- nmr
- Prior art date
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- 125000005605 benzo group Chemical group 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 claims description 21
- -1 benzo compound Chemical class 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims description 4
- 208000030990 Impulse-control disease Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 206010001584 alcohol abuse Diseases 0.000 claims description 4
- 208000025746 alcohol use disease Diseases 0.000 claims description 4
- 239000000164 antipsychotic agent Substances 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 208000023589 ischemic disease Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract description 2
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract description 2
- 239000003446 ligand Substances 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 153
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 238000005481 NMR spectroscopy Methods 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 36
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000003921 oil Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 20
- 108091005479 5-HT2 receptors Proteins 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 230000004044 response Effects 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 241000700159 Rattus Species 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000004031 partial agonist Substances 0.000 description 11
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N 5-methoxy-N,N-dimethyltryptamine Chemical compound COC1=CC=C2NC=C(CCN(C)C)C2=C1 ZSTKHSQDNIGFLM-UHFFFAOYSA-N 0.000 description 10
- ASXGJMSKWNBENU-UHFFFAOYSA-N 8-OH-DPAT Chemical compound C1=CC(O)=C2CC(N(CCC)CCC)CCC2=C1 ASXGJMSKWNBENU-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000010561 standard procedure Methods 0.000 description 8
- 239000000556 agonist Substances 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 208000011580 syndromic disease Diseases 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- WVLHGCRWEHCIOT-UHFFFAOYSA-N eltoprazine Chemical compound C1CNCCN1C1=CC=CC2=C1OCCO2 WVLHGCRWEHCIOT-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000003478 serotonin 5-HT2 receptor agonist Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 150000003891 oxalate salts Chemical class 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 3
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
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- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
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- 150000003568 thioethers Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OTYCNPBUKLAUDN-UHFFFAOYSA-N 1-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethyl]-1-(2,2-dimethoxyethyl)-3-(4-fluorophenyl)urea Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CCN(CC(OC)OC)C(=O)NC1=CC=C(F)C=C1 OTYCNPBUKLAUDN-UHFFFAOYSA-N 0.000 description 2
- KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 2
- SJSAOEMZUWRZRY-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]acetonitrile Chemical compound C1CN(CC#N)CCN1C1=CC=CC2=C1OCCO2 SJSAOEMZUWRZRY-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK921483A DK148392D0 (da) | 1992-12-09 | 1992-12-09 | Heterocykliske forbindelser |
PCT/DK1993/000414 WO1994013659A1 (en) | 1992-12-09 | 1993-12-08 | Fused benzo compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
NO952275D0 NO952275D0 (no) | 1995-06-08 |
NO952275L NO952275L (no) | 1995-08-03 |
NO311617B1 true NO311617B1 (no) | 2001-12-17 |
Family
ID=8105314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19952275A NO311617B1 (no) | 1992-12-09 | 1995-06-08 | Kondenserte benzoforbindelser |
Country Status (23)
Country | Link |
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US (2) | US5753661A (sk) |
EP (1) | EP0673375B1 (sk) |
JP (1) | JPH08504410A (sk) |
KR (1) | KR100299624B1 (sk) |
AT (1) | ATE176909T1 (sk) |
AU (1) | AU675263B2 (sk) |
CA (1) | CA2151378A1 (sk) |
CZ (1) | CZ283143B6 (sk) |
DE (1) | DE69323630T2 (sk) |
DK (2) | DK148392D0 (sk) |
ES (1) | ES2127912T3 (sk) |
FI (1) | FI109697B (sk) |
GR (1) | GR3030200T3 (sk) |
HU (1) | HUT73632A (sk) |
IL (1) | IL107923A (sk) |
MX (1) | MX9307779A (sk) |
NO (1) | NO311617B1 (sk) |
NZ (1) | NZ258117A (sk) |
RU (1) | RU2141959C1 (sk) |
SG (1) | SG52722A1 (sk) |
SK (1) | SK280779B6 (sk) |
WO (1) | WO1994013659A1 (sk) |
ZA (1) | ZA939203B (sk) |
Families Citing this family (36)
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DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
ES2117934B1 (es) * | 1994-07-29 | 1999-04-01 | Esteve Labor Dr | Tetrahidropiridinas (0 4-hidroxipiperidinas) alquilazoles. |
FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
FR2735127B1 (fr) * | 1995-06-09 | 1997-08-22 | Pf Medicament | Nouvelles piperazines heteroaromatiques utiles comme medicaments. |
SE9601110D0 (sv) | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
PL189256B1 (pl) * | 1996-03-29 | 2005-07-29 | Duphar Int Res | Związki piperazyny i piperydyny, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca te związki, zastosowanie tych związków do wytwarzania leków |
FR2757161B1 (fr) * | 1996-12-13 | 1999-03-12 | Sanofi Sa | Diphenylalkyl-tetrahydropyridines |
GB9706222D0 (en) * | 1997-03-26 | 1997-05-14 | Zeneca Ltd | Bicyclic amine derivatives |
US6077850A (en) | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
SE9900190D0 (sv) | 1999-01-22 | 1999-01-22 | Astra Ab | New compounds |
SE9702799D0 (sv) | 1997-07-25 | 1997-07-25 | Astra Ab | New compounds |
ATE253058T1 (de) | 1997-09-02 | 2003-11-15 | Duphar Int Res | Piperidin- und piperazin derivate als 5-ht1- rezeptor-agonisten |
EP0900792B1 (en) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
DE69903239T2 (de) * | 1998-06-30 | 2003-09-11 | Lilly Co Eli | Auf serotonin-verwandte Systeme wirkende Piperidin-Derivate |
EP1146045A1 (en) * | 1998-06-30 | 2001-10-17 | Eli Lilly And Company | Piperidine derivatives having effects on serotonin related systems |
UA71590C2 (en) * | 1998-11-13 | 2004-12-15 | Duphar Int Res | Piperazine and piperidine derivatives |
AR022303A1 (es) | 1999-01-22 | 2002-09-04 | Lundbeck & Co As H | Derivados de piperidina, tetrahidropiridina y piperazina, su preparacion y utilizacion |
AU5866500A (en) * | 1999-06-29 | 2001-01-31 | Eli Lilly And Company | Preparation of 7-substituted benzothiophenes |
AR027134A1 (es) * | 1999-12-30 | 2003-03-12 | Lundbeck & Co As H | Derivados de indol. |
AR027133A1 (es) * | 1999-12-30 | 2003-03-12 | Lundbeck & Co As H | Derivados de heteroarilo, su preparacion y uso. |
FR2803298A1 (fr) * | 1999-12-30 | 2001-07-06 | Adir | Nouvelles urees lineaires ou cycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2804429B1 (fr) * | 2000-01-31 | 2003-05-09 | Adir | Nouveaux derives de 4-sulfonamides piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
EP1284731A1 (en) * | 2000-05-12 | 2003-02-26 | Solvay Pharmaceuticals B.V. | Use of compounds having combined dopamine d2, 5-ht1a and alpha adrenoreceptor agonistic action for treating cns disorders |
DE10043659A1 (de) * | 2000-09-05 | 2002-03-14 | Merck Patent Gmbh | Arylpiperazinderivate |
US6743796B2 (en) | 2001-05-07 | 2004-06-01 | Wyeth | Piperazinyl-isatins |
WO2003007956A1 (en) | 2001-07-20 | 2003-01-30 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
AU2003254993A1 (en) | 2002-08-12 | 2004-03-03 | Takeda Pharmaceutical Company Limited | Fused benzene derivative and use |
CA2517146A1 (en) | 2003-03-03 | 2004-09-16 | F. Hoffmann-La Roche Ag | 2,5- and 2,6-substituted tetrahydroisoquinolines for use as 5-ht6 modulators |
TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
US8389510B2 (en) * | 2005-11-18 | 2013-03-05 | Astrazeneca Ab | Crystalline forms |
EP2099459A4 (en) * | 2006-12-20 | 2011-04-27 | Astrazeneca Ab | COMPOUNDS AND USES THEREOF |
US8367676B2 (en) * | 2009-06-30 | 2013-02-05 | Astrazeneca Ab | 2-carboxamide-7-piperazinyl-benzofuran derivatives 774 |
WO2011069075A2 (en) | 2009-12-04 | 2011-06-09 | Grant Jon E | Treating impulse control disorders with catechol-o- methyl-transferase inhibitors |
CN106065018B (zh) * | 2015-04-23 | 2020-04-21 | 广东东阳光药业有限公司 | 取代的吲哚化合物及其使用方法和用途 |
CA3008653A1 (en) * | 2015-10-14 | 2017-04-20 | Zibo Biopolar Changsheng Pharmaceutical Co. Ltd. | Bruton's tyrosine kinase inhibitors |
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CH511235A (de) * | 1969-07-17 | 1971-08-15 | Ciba Geigy Ag | Verfahren zur Herstellung von 1-Alkyl-3-(2-halogen-äthyl)-2-imidazolidinonen |
DE2263211A1 (de) * | 1972-12-23 | 1974-07-04 | Boehringer Sohn Ingelheim | Neue arylpiperazine und verfahren zu ihrer herstellung |
DE2727469A1 (de) * | 1977-06-18 | 1978-12-21 | Hoechst Ag | Neue hexahydropyrimidine, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
US4302592A (en) * | 1980-09-15 | 1981-11-24 | Shell Oil Company | Pesticidal 3-(2,3-dihydrobenzofuran-7-yl)-5-methoxy-1,3,4-oxadiazol-2(3H)-one |
US4506078A (en) * | 1981-06-05 | 1985-03-19 | Hoffmann-La Roche Inc. | 7-Nitroindoles |
AU577802B2 (en) * | 1983-10-17 | 1988-10-06 | Duphar International Research B.V. | Blood-pressure lowering piperazine derivatives |
CA1297877C (en) * | 1983-12-22 | 1992-03-24 | Daniel Lednicer | Benzofurancarboxamides useful as antiemetic or antipsychotic agents |
JPS6133183A (ja) * | 1984-07-25 | 1986-02-17 | Mitsubishi Chem Ind Ltd | 2,3−ジヒドロ−7−アミノベンゾフランの製造法 |
EP0185429A1 (en) * | 1984-12-21 | 1986-06-25 | Duphar International Research B.V | New bicyclic heteroaryl piperazines |
ATE81975T1 (de) * | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
MX173362B (es) * | 1987-03-02 | 1994-02-23 | Pfizer | Compuestos de piperazinil heterociclicos y procedimiento para su preparacion |
US4831031A (en) * | 1988-01-22 | 1989-05-16 | Pfizer Inc. | Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity |
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 |
FR2637591B1 (fr) * | 1988-10-11 | 1992-10-23 | Synthelabo | Derives de quinoleinone, leur preparation et leur application en therapeutique |
IL92544A0 (en) * | 1988-12-08 | 1990-08-31 | Duphar Int Res | Piperazine derivatives,their preparation and pharmaceutical compositions containing them |
GB8830312D0 (en) * | 1988-12-28 | 1989-02-22 | Lundbeck & Co As H | Heterocyclic compounds |
DK152090D0 (da) * | 1990-06-22 | 1990-06-22 | Lundbaek A S H | Piperidylsubstituerede indolderivater |
FR2664592B1 (fr) * | 1990-07-10 | 1994-09-02 | Adir | Nouveaux derives de la piperidine, de la tetrahydropyridine et de la pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
DK203990D0 (da) * | 1990-08-24 | 1990-08-24 | Novo Nordisk As | Piperazinylderivater |
FR2670491B1 (fr) * | 1990-12-14 | 1993-02-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
IT1251144B (it) * | 1991-07-30 | 1995-05-04 | Boehringer Ingelheim Italia | Derivati del benzimidazolone |
-
1992
- 1992-12-09 DK DK921483A patent/DK148392D0/da not_active IP Right Cessation
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1993
- 1993-12-07 IL IL10792393A patent/IL107923A/en not_active IP Right Cessation
- 1993-12-08 DK DK94900793T patent/DK0673375T3/da active
- 1993-12-08 ZA ZA939203A patent/ZA939203B/xx unknown
- 1993-12-08 KR KR1019950702356A patent/KR100299624B1/ko not_active IP Right Cessation
- 1993-12-08 DE DE69323630T patent/DE69323630T2/de not_active Expired - Fee Related
- 1993-12-08 EP EP94900793A patent/EP0673375B1/en not_active Expired - Lifetime
- 1993-12-08 ES ES94900793T patent/ES2127912T3/es not_active Expired - Lifetime
- 1993-12-08 CA CA002151378A patent/CA2151378A1/en not_active Abandoned
- 1993-12-08 JP JP6513691A patent/JPH08504410A/ja not_active Withdrawn
- 1993-12-08 AU AU55618/94A patent/AU675263B2/en not_active Ceased
- 1993-12-08 SG SG1996008300A patent/SG52722A1/en unknown
- 1993-12-08 RU RU95117096A patent/RU2141959C1/ru not_active IP Right Cessation
- 1993-12-08 NZ NZ258117A patent/NZ258117A/en unknown
- 1993-12-08 SK SK761-95A patent/SK280779B6/sk unknown
- 1993-12-08 WO PCT/DK1993/000414 patent/WO1994013659A1/en active IP Right Grant
- 1993-12-08 HU HU9501668A patent/HUT73632A/hu unknown
- 1993-12-08 CZ CZ951517A patent/CZ283143B6/cs not_active IP Right Cessation
- 1993-12-08 AT AT94900793T patent/ATE176909T1/de not_active IP Right Cessation
- 1993-12-09 MX MX9307779A patent/MX9307779A/es not_active IP Right Cessation
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1995
- 1995-06-06 US US08/504,846 patent/US5753661A/en not_active Expired - Fee Related
- 1995-06-08 NO NO19952275A patent/NO311617B1/no not_active IP Right Cessation
- 1995-06-08 FI FI952824A patent/FI109697B/fi not_active IP Right Cessation
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1997
- 1997-12-24 US US08/998,245 patent/US6140331A/en not_active Expired - Fee Related
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1999
- 1999-05-13 GR GR990401285T patent/GR3030200T3/el unknown
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