AU2004228119B2 - Pyrazole compounds - Google Patents
Pyrazole compounds Download PDFInfo
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- AU2004228119B2 AU2004228119B2 AU2004228119A AU2004228119A AU2004228119B2 AU 2004228119 B2 AU2004228119 B2 AU 2004228119B2 AU 2004228119 A AU2004228119 A AU 2004228119A AU 2004228119 A AU2004228119 A AU 2004228119A AU 2004228119 B2 AU2004228119 B2 AU 2004228119B2
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- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 104
- -1 1-piperidyl Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000012453 solvate Substances 0.000 claims description 32
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 238000011321 prophylaxis Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 235000014632 disordered eating Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 5
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 5
- 102100038239 Protein Churchill Human genes 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 3
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 2
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000005495 pyridazyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 69
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000010626 work up procedure Methods 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 101150104779 HTR2A gene Proteins 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 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
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- CZGIEJXGCLWRPY-UHFFFAOYSA-N n,1-dimethylpyrrolidin-3-amine Chemical compound CNC1CCN(C)C1 CZGIEJXGCLWRPY-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OUZHKZDOXDCQDE-UHFFFAOYSA-N 1-[1-[2-fluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]-n,n-dimethylmethanamine Chemical compound CN(C)CC=1C=NN(C=2C(=CC(=CC=2)C=2C=CC(F)=CC=2)F)C=1C1=CC=CO1 OUZHKZDOXDCQDE-UHFFFAOYSA-N 0.000 description 2
- FIXZHXVSGXMMCN-UHFFFAOYSA-N 1-[[1-(5-chloro-1-fluoro-4-phenylcyclohexa-2,4-dien-1-yl)-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound ClC1=C(C=CC(C1)(F)N1N=CC(=C1C=1OC=CC=1)CN1CCN(CC1)C)C1=CC=CC=C1 FIXZHXVSGXMMCN-UHFFFAOYSA-N 0.000 description 2
- ZIPLULAYKVIJID-UHFFFAOYSA-N 1-[[1-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-ethylpiperazine Chemical compound C1CN(CC)CCN1CC1=C(C=2OC=CC=2)N(C=2C=C(F)C(=C(F)C=2)C=2C=CC(F)=CC=2)N=C1 ZIPLULAYKVIJID-UHFFFAOYSA-N 0.000 description 2
- ZWSSNYCATFGFDG-UHFFFAOYSA-N 1-[[1-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=C(C=2OC=CC=2)N(C=2C=C(F)C(=C(F)C=2)C=2C=CC(F)=CC=2)N=C1 ZWSSNYCATFGFDG-UHFFFAOYSA-N 0.000 description 2
- LMXLIBSIUHPQPP-UHFFFAOYSA-N 1-[[1-[4-(4-fluorophenyl)-2-methylphenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=C(C=2OC=CC=2)N(C=2C(=CC(=CC=2)C=2C=CC(F)=CC=2)C)N=C1 LMXLIBSIUHPQPP-UHFFFAOYSA-N 0.000 description 2
- BOXBCTKWCUBCPF-UHFFFAOYSA-N 1-[[1-[4-(4-fluorophenyl)-2-methylphenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CC(C=2C=CC(F)=CC=2)=CC=C1N(C=1C=2OC=CC=2)N=CC=1CN1CCC(O)C1 BOXBCTKWCUBCPF-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IFANPEQRAMCBSC-UHFFFAOYSA-N 2-[3-methyl-5-phenyl-1-(4-phenylphenyl)pyrazol-4-yl]ethanol Chemical compound OCCC=1C(C)=NN(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=1C1=CC=CC=C1 IFANPEQRAMCBSC-UHFFFAOYSA-N 0.000 description 2
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000020706 Autistic disease Diseases 0.000 description 2
- 208000032841 Bulimia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 2
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 2
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Classifications
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- 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
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Landscapes
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
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- Public Health (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10315571.6 | 2003-04-05 | ||
| DE2003115571 DE10315571A1 (de) | 2003-04-05 | 2003-04-05 | Pyrazolverbindungen |
| PCT/EP2004/002352 WO2004089888A1 (de) | 2003-04-05 | 2004-03-08 | Pyrazolverbindungen |
Publications (2)
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|---|---|
| AU2004228119A1 AU2004228119A1 (en) | 2004-10-21 |
| AU2004228119B2 true AU2004228119B2 (en) | 2010-09-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2004228119A Ceased AU2004228119B2 (en) | 2003-04-05 | 2004-03-08 | Pyrazole compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7960413B2 (enExample) |
| EP (1) | EP1611094B1 (enExample) |
| JP (1) | JP4833832B2 (enExample) |
| KR (1) | KR20050119195A (enExample) |
| CN (1) | CN1768053A (enExample) |
| AR (1) | AR043836A1 (enExample) |
| AT (1) | ATE365161T1 (enExample) |
| AU (1) | AU2004228119B2 (enExample) |
| BR (1) | BRPI0409160A (enExample) |
| CA (1) | CA2521199A1 (enExample) |
| DE (2) | DE10315571A1 (enExample) |
| ES (1) | ES2287707T3 (enExample) |
| MX (1) | MXPA05010651A (enExample) |
| PL (1) | PL377685A1 (enExample) |
| RU (1) | RU2005133985A (enExample) |
| WO (1) | WO2004089888A1 (enExample) |
| ZA (1) | ZA200508946B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10315572A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315571A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315573A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| MX2008000141A (es) | 2005-06-27 | 2008-04-07 | Exelixis Inc | Moduladores de lxr basados en imidazol. |
| JP2008169191A (ja) * | 2006-02-20 | 2008-07-24 | Eisai R & D Management Co Ltd | 運動ニューロン疾患治療剤 |
| CA2644069A1 (en) | 2006-02-28 | 2007-09-07 | Helicon Therapeutics, Inc. | Therapeutic piperazines as pde4 inhibitors |
| WO2007100851A1 (en) * | 2006-02-28 | 2007-09-07 | Helicon Therapeutics, Inc. | Therapeutic compounds |
| USRE45336E1 (en) | 2006-05-18 | 2015-01-13 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| CA2646076C (en) | 2006-05-18 | 2015-06-30 | Arena Pharmaceuticals, Inc. | Ethers, secondary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP2121621B1 (en) | 2006-12-08 | 2014-05-07 | Exelixis Patent Company LLC | Lxr and fxr modulators |
| JP5718053B2 (ja) | 2007-08-27 | 2015-05-13 | ヘリコン・セラピューティクス・インコーポレーテッド | 治療用イソオキサゾール化合物 |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325962A (en) * | 1969-09-12 | 1982-04-20 | Byk-Gulden Lomberg Chemische Fabrik Gmbh | Pharmaceutical compositions comprising a pyrazole derivative and method of use |
| WO2001032626A1 (en) * | 1999-11-05 | 2001-05-10 | Smithkline Beecham P.L.C. | Isoquinoline and quinazoline derivatives having a combined 5ht1a, 5ht1b and 5ht1d receptor activity |
| WO2003031435A1 (en) * | 2001-10-06 | 2003-04-17 | Merck Patent Gmbh | Pyrazole derivatives as glycine transporter inhibitors |
| AU2003223579A1 (en) * | 2002-04-18 | 2003-11-03 | Pharmacia Corporation | Combinations of cox-2 inhibitors and other agents for the treatment of parkinson's disease |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH518155A (de) | 1970-08-18 | 1972-01-31 | Schaerer Willy | Verfahren zur Erleichterung des Schleifens schraubenlinienförmiger Nuten, bei einer Serie von unter sich gleichen Werkstücken mit je mindestens einer schraubenlinienförmig eingefrästen Nut und Simuliergerät zur Durchführung des Verfahrens |
| BE793955A (fr) | 1972-01-15 | 1973-07-12 | Merck Patent Gmbh | Arylpiperazines et leur procede de preparation |
| DE2258033A1 (de) | 1972-11-27 | 1974-05-30 | Merck Patent Gmbh | Verfahren zur herstellung von pyrazolderivaten |
| DE2906252A1 (de) | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4631343A (en) | 1983-11-07 | 1986-12-23 | Eli Lilly And Company | Cyanopyrazole intermediates |
| NZ305799A (en) | 1995-04-20 | 1999-01-28 | Searle & Co | Cyclic amidino agents useful as nitric oxide synthase inhibitors |
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-
2004
- 2004-03-08 MX MXPA05010651A patent/MXPA05010651A/es not_active Application Discontinuation
- 2004-03-08 PL PL377685A patent/PL377685A1/pl unknown
- 2004-03-08 EP EP04718288A patent/EP1611094B1/de not_active Expired - Lifetime
- 2004-03-08 AT AT04718288T patent/ATE365161T1/de not_active IP Right Cessation
- 2004-03-08 AU AU2004228119A patent/AU2004228119B2/en not_active Ceased
- 2004-03-08 BR BRPI0409160-4A patent/BRPI0409160A/pt not_active Application Discontinuation
- 2004-03-08 ES ES04718288T patent/ES2287707T3/es not_active Expired - Lifetime
- 2004-03-08 CN CNA2004800086045A patent/CN1768053A/zh active Pending
- 2004-03-08 WO PCT/EP2004/002352 patent/WO2004089888A1/de not_active Ceased
- 2004-03-08 JP JP2006504583A patent/JP4833832B2/ja not_active Expired - Fee Related
- 2004-03-08 US US10/551,905 patent/US7960413B2/en not_active Expired - Fee Related
- 2004-03-08 RU RU2005133985/04A patent/RU2005133985A/ru not_active Application Discontinuation
- 2004-03-08 CA CA002521199A patent/CA2521199A1/en not_active Abandoned
- 2004-03-08 DE DE502004004146T patent/DE502004004146D1/de not_active Expired - Lifetime
- 2004-03-08 KR KR1020057018899A patent/KR20050119195A/ko not_active Withdrawn
- 2004-04-02 AR ARP040101118A patent/AR043836A1/es unknown
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2005
- 2005-11-04 ZA ZA200508946A patent/ZA200508946B/xx unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2287707T3 (es) | 2007-12-16 |
| DE502004004146D1 (en) | 2007-08-02 |
| DE10315571A1 (de) | 2004-10-14 |
| AU2004228119A1 (en) | 2004-10-21 |
| PL377685A1 (pl) | 2006-02-06 |
| WO2004089888A1 (de) | 2004-10-21 |
| AR043836A1 (es) | 2005-08-17 |
| JP4833832B2 (ja) | 2011-12-07 |
| JP2006523626A (ja) | 2006-10-19 |
| KR20050119195A (ko) | 2005-12-20 |
| MXPA05010651A (es) | 2005-12-12 |
| US7960413B2 (en) | 2011-06-14 |
| EP1611094A1 (de) | 2006-01-04 |
| RU2005133985A (ru) | 2006-03-27 |
| ATE365161T1 (de) | 2007-07-15 |
| US20060276650A1 (en) | 2006-12-07 |
| CA2521199A1 (en) | 2004-10-21 |
| BRPI0409160A (pt) | 2006-05-02 |
| EP1611094B1 (de) | 2007-06-20 |
| CN1768053A (zh) | 2006-05-03 |
| ZA200508946B (en) | 2007-02-28 |
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