JP2009528317A5 - - Google Patents
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- Publication number
- JP2009528317A5 JP2009528317A5 JP2008556725A JP2008556725A JP2009528317A5 JP 2009528317 A5 JP2009528317 A5 JP 2009528317A5 JP 2008556725 A JP2008556725 A JP 2008556725A JP 2008556725 A JP2008556725 A JP 2008556725A JP 2009528317 A5 JP2009528317 A5 JP 2009528317A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- cyclohexyl
- yloxy
- pyrazol
- Prior art date
- 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.)
- Pending
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- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- -1 -N = CR 8 R 9 Inorganic materials 0.000 claims 5
- 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 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 208000004454 Hyperalgesia Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- BMZADBOYNSISHO-UHFFFAOYSA-N 1-[4-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCCCOC1=NN(C2CCCCC2)C=C1 BMZADBOYNSISHO-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003053 piperidines Chemical class 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- DSXVAVPMYGNJGX-UHFFFAOYSA-N 1-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]piperidine Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCN1CCCCC1 DSXVAVPMYGNJGX-UHFFFAOYSA-N 0.000 claims 1
- JXJOJSXOGPTVJH-UHFFFAOYSA-N 1-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]piperidine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C2CCCCC2)C(C)=CC=1OCCN1CCCCC1 JXJOJSXOGPTVJH-UHFFFAOYSA-N 0.000 claims 1
- YEGWKVVMKSPGST-UHFFFAOYSA-N 1-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]-4-phenylpiperidine Chemical compound C1=CN(C2CCCCC2)N=C1OCCN(CC1)CCC1C1=CC=CC=C1 YEGWKVVMKSPGST-UHFFFAOYSA-N 0.000 claims 1
- VJWIVVPZHPXARQ-UHFFFAOYSA-N 1-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]-4-phenylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CN(C2CCCCC2)N=C1OCCN(CC1)CCC1C1=CC=CC=C1 VJWIVVPZHPXARQ-UHFFFAOYSA-N 0.000 claims 1
- PCQQVJFPPGFXFB-UHFFFAOYSA-N 1-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]piperidine Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCCCC1 PCQQVJFPPGFXFB-UHFFFAOYSA-N 0.000 claims 1
- GGJGMRODDURYBX-UHFFFAOYSA-N 1-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]piperidine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCCCC1 GGJGMRODDURYBX-UHFFFAOYSA-N 0.000 claims 1
- RLJFYTNLPGXWGD-UHFFFAOYSA-N 1-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]piperidine Chemical compound C1=CN(C2CCCCC2)N=C1OCCCCN1CCCCC1 RLJFYTNLPGXWGD-UHFFFAOYSA-N 0.000 claims 1
- GPBNUXKHLVDGKA-UHFFFAOYSA-N 1-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]piperidine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CN(C2CCCCC2)N=C1OCCCCN1CCCCC1 GPBNUXKHLVDGKA-UHFFFAOYSA-N 0.000 claims 1
- HXCUMIIBTKBUHF-UHFFFAOYSA-N 1-[4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=NN(C2CCCCC2)C(C)=C1 HXCUMIIBTKBUHF-UHFFFAOYSA-N 0.000 claims 1
- QZBDUSGIXLOFET-UHFFFAOYSA-N 1-[4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]piperazin-1-yl]ethanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C(=O)C)CCN1CCOC1=NN(C2CCCCC2)C(C)=C1 QZBDUSGIXLOFET-UHFFFAOYSA-N 0.000 claims 1
- SLXMDBDBVAINAL-UHFFFAOYSA-N 1-[4-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=NN(C2CCCCC2)C=C1 SLXMDBDBVAINAL-UHFFFAOYSA-N 0.000 claims 1
- VBNMXCKOFHFMKK-UHFFFAOYSA-N 1-[4-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]piperazin-1-yl]ethanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C(=O)C)CCN1CCOC1=NN(C2CCCCC2)C=C1 VBNMXCKOFHFMKK-UHFFFAOYSA-N 0.000 claims 1
- ZAHURUIVSFAUJJ-UHFFFAOYSA-N 1-[4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCCCOC1=NN(C2CCCCC2)C(C)=C1 ZAHURUIVSFAUJJ-UHFFFAOYSA-N 0.000 claims 1
- JNRQOSYYWXMKDL-UHFFFAOYSA-N 1-[4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]piperazin-1-yl]ethanone;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C(=O)C)CCN1CCCCOC1=NN(C2CCCCC2)C(C)=C1 JNRQOSYYWXMKDL-UHFFFAOYSA-N 0.000 claims 1
- CSSFRSCFAFDICD-UHFFFAOYSA-N 1-cyclohexyl-3-(2-pyrrolidin-1-ylethoxy)pyrazole Chemical compound C1=CN(C2CCCCC2)N=C1OCCN1CCCC1 CSSFRSCFAFDICD-UHFFFAOYSA-N 0.000 claims 1
- WWMCKWIJAYDTQA-UHFFFAOYSA-N 1-cyclohexyl-3-(2-pyrrolidin-1-ylethoxy)pyrazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CN(C2CCCCC2)N=C1OCCN1CCCC1 WWMCKWIJAYDTQA-UHFFFAOYSA-N 0.000 claims 1
- RIERRMZULZPIAD-UHFFFAOYSA-N 1-cyclohexyl-3-(4-pyrrolidin-1-ylbutoxy)pyrazole Chemical compound C1=CN(C2CCCCC2)N=C1OCCCCN1CCCC1 RIERRMZULZPIAD-UHFFFAOYSA-N 0.000 claims 1
- JKISDIIWOBQDFE-UHFFFAOYSA-N 1-cyclohexyl-3-(4-pyrrolidin-1-ylbutoxy)pyrazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CN(C2CCCCC2)N=C1OCCCCN1CCCC1 JKISDIIWOBQDFE-UHFFFAOYSA-N 0.000 claims 1
- AXLYPLMUISGHCH-UHFFFAOYSA-N 1-cyclohexyl-5-methyl-3-(2-pyrrolidin-1-ylethoxy)pyrazole Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCN1CCCC1 AXLYPLMUISGHCH-UHFFFAOYSA-N 0.000 claims 1
- ULEJKGXVAKSUCS-UHFFFAOYSA-N 1-cyclohexyl-5-methyl-3-(4-pyrrolidin-1-ylbutoxy)pyrazole Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCCC1 ULEJKGXVAKSUCS-UHFFFAOYSA-N 0.000 claims 1
- GBZOYOGMBYRRCP-UHFFFAOYSA-N 1-cyclohexyl-5-methyl-3-(4-pyrrolidin-1-ylbutoxy)pyrazole;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCCC1 GBZOYOGMBYRRCP-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- KLBATFXVZSLMDJ-UHFFFAOYSA-N 2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxy-n,n-diethylethanamine Chemical compound N1=C(OCCN(CC)CC)C=C(C)N1C1CCCCC1 KLBATFXVZSLMDJ-UHFFFAOYSA-N 0.000 claims 1
- FCAUOPSAWFBTTF-UHFFFAOYSA-N 2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxy-n,n-diethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.N1=C(OCCN(CC)CC)C=C(C)N1C1CCCCC1 FCAUOPSAWFBTTF-UHFFFAOYSA-N 0.000 claims 1
- CYFSJTCHOLYHRW-UHFFFAOYSA-N 4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxy-n,n-diethylbutan-1-amine Chemical compound N1=C(OCCCCN(CC)CC)C=C(C)N1C1CCCCC1 CYFSJTCHOLYHRW-UHFFFAOYSA-N 0.000 claims 1
- VHZQMZDKKOJKOT-UHFFFAOYSA-N 4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxy-n,n-diethylbutan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.N1=C(OCCCCN(CC)CC)C=C(C)N1C1CCCCC1 VHZQMZDKKOJKOT-UHFFFAOYSA-N 0.000 claims 1
- HAZMUXIZURAUEF-UHFFFAOYSA-N 4-(1-cyclohexylpyrazol-3-yl)oxy-n,n-diethylbutan-1-amine Chemical compound N1=C(OCCCCN(CC)CC)C=CN1C1CCCCC1 HAZMUXIZURAUEF-UHFFFAOYSA-N 0.000 claims 1
- GYAIDTCRSMCBPJ-UHFFFAOYSA-N 4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCOC1=NN(C2CCCCC2)C(C)=C1 GYAIDTCRSMCBPJ-UHFFFAOYSA-N 0.000 claims 1
- KJBXGGWRHDNEHE-UHFFFAOYSA-N 4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]-2,6-dimethylmorpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1C(C)OC(C)CN1CCOC1=NN(C2CCCCC2)C(C)=C1 KJBXGGWRHDNEHE-UHFFFAOYSA-N 0.000 claims 1
- KSTKENJUOVJKCO-UHFFFAOYSA-N 4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]morpholine Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCN1CCOCC1 KSTKENJUOVJKCO-UHFFFAOYSA-N 0.000 claims 1
- VSLIQQFAFBYHJP-UHFFFAOYSA-N 4-[2-(1-cyclohexyl-5-methylpyrazol-3-yl)oxyethyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C2CCCCC2)C(C)=CC=1OCCN1CCOCC1 VSLIQQFAFBYHJP-UHFFFAOYSA-N 0.000 claims 1
- YVYNYRGTSUMBOY-UHFFFAOYSA-N 4-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCOC1=NN(C2CCCCC2)C=C1 YVYNYRGTSUMBOY-UHFFFAOYSA-N 0.000 claims 1
- JLQCTXLELKYACU-UHFFFAOYSA-N 4-[2-(1-cyclohexylpyrazol-3-yl)oxyethyl]-2,6-dimethylmorpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1C(C)OC(C)CN1CCOC1=NN(C2CCCCC2)C=C1 JLQCTXLELKYACU-UHFFFAOYSA-N 0.000 claims 1
- VQRRDNDGCAVUNQ-UHFFFAOYSA-N 4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCCCOC1=NN(C2CCCCC2)C(C)=C1 VQRRDNDGCAVUNQ-UHFFFAOYSA-N 0.000 claims 1
- HPXLLKPBRWPMLR-UHFFFAOYSA-N 4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]-2,6-dimethylmorpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1C(C)OC(C)CN1CCCCOC1=NN(C2CCCCC2)C(C)=C1 HPXLLKPBRWPMLR-UHFFFAOYSA-N 0.000 claims 1
- ZAADKIYBPKMTAV-UHFFFAOYSA-N 4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]morpholine Chemical compound N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCOCC1 ZAADKIYBPKMTAV-UHFFFAOYSA-N 0.000 claims 1
- JMSRJLIZBJPUGB-UHFFFAOYSA-N 4-[4-(1-cyclohexyl-5-methylpyrazol-3-yl)oxybutyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C2CCCCC2)C(C)=CC=1OCCCCN1CCOCC1 JMSRJLIZBJPUGB-UHFFFAOYSA-N 0.000 claims 1
- DYBUHZFEXNXFAK-UHFFFAOYSA-N 4-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCCCOC1=NN(C2CCCCC2)C=C1 DYBUHZFEXNXFAK-UHFFFAOYSA-N 0.000 claims 1
- LVENMUWFRDCGAX-UHFFFAOYSA-N 4-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]-2,6-dimethylmorpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1C(C)OC(C)CN1CCCCOC1=NN(C2CCCCC2)C=C1 LVENMUWFRDCGAX-UHFFFAOYSA-N 0.000 claims 1
- ZRCJWUJOCMLJIE-UHFFFAOYSA-N 4-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]morpholine Chemical compound C1=CN(C2CCCCC2)N=C1OCCCCN1CCOCC1 ZRCJWUJOCMLJIE-UHFFFAOYSA-N 0.000 claims 1
- SWEOLCZBILGFFG-UHFFFAOYSA-N 4-[4-(1-cyclohexylpyrazol-3-yl)oxybutyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CN(C2CCCCC2)N=C1OCCCCN1CCOCC1 SWEOLCZBILGFFG-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010060755 Type V hyperlipidaemia Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010053552 allodynia Diseases 0.000 claims 1
- 229940025084 amphetamine Drugs 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 230000036528 appetite Effects 0.000 claims 1
- 235000019789 appetite Nutrition 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 235000012631 food intake Nutrition 0.000 claims 1
- 230000036541 health Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 150000003891 oxalate salts Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 108010085082 sigma receptors Proteins 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06004198A EP1829866A1 (en) | 2006-03-02 | 2006-03-02 | Sigma receptor inhibitors |
| PCT/EP2007/001826 WO2007098963A1 (en) | 2006-03-02 | 2007-03-02 | Sigma receptor inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009528317A JP2009528317A (ja) | 2009-08-06 |
| JP2009528317A5 true JP2009528317A5 (enExample) | 2010-04-15 |
Family
ID=36372388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008556725A Pending JP2009528317A (ja) | 2006-03-02 | 2007-03-02 | シグマ受容体阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8088812B2 (enExample) |
| EP (2) | EP1829866A1 (enExample) |
| JP (1) | JP2009528317A (enExample) |
| CN (1) | CN101395138B (enExample) |
| CA (1) | CA2640753A1 (enExample) |
| ES (1) | ES2392193T3 (enExample) |
| MX (1) | MX2008011018A (enExample) |
| PT (1) | PT1996554E (enExample) |
| WO (1) | WO2007098963A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2353598A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2395003A1 (en) * | 2010-05-27 | 2011-12-14 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazole compounds as sigma receptor inhibitors |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2631236A1 (en) * | 2012-02-21 | 2013-08-28 | Laboratorios Del. Dr. Esteve, S.A. | Substituted pyrazolo[1,5-a]pyridines, their preparation and use as medicaments |
| CA2933511A1 (en) | 2013-12-17 | 2015-06-25 | Laboratorios Del Dr. Esteve, S.A. | Serotonin-norepinephrine reuptake inhibitors (snris) and sigma receptor ligands combinations |
| WO2017021002A1 (en) * | 2015-07-31 | 2017-02-09 | Laboratorios Del Dr. Esteve, S.A. | Use of sigma receptor ligands in dyslipidemia |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2301250A1 (fr) | 1975-02-21 | 1976-09-17 | Bellon Labor Sa Roger | Nouveaux diaryl-1, 4o-aminoalcoxy-3 pyrazoles et leurs sels |
| FR2460299A1 (fr) | 1979-07-05 | 1981-01-23 | Bellon Labor Sa Roger | Nouveaux derives du pyrazole et leur application therapeutique |
| FR2472564A1 (fr) | 1979-12-31 | 1981-07-03 | Bellon Labor Sa Roger | Nouveaux aryl-1 arylsulfonyl-4 1h-pyrazolols-3, et procede pour les preparer |
| GB8917069D0 (en) | 1989-07-26 | 1989-09-13 | Merck Sharp & Dohme | Therapeutic agents |
| IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| EP0507863A4 (en) | 1989-12-28 | 1993-07-07 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| EP0445974A3 (en) | 1990-03-05 | 1992-04-29 | Merck Sharp & Dohme Ltd. | Spirocyclic antipsychotic agents |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DE4341749A1 (de) * | 1993-12-08 | 1995-06-14 | Kali Chemie Pharma Gmbh | 3-(Phenylalkylaminoalkyloxy)-5-phenylpyrazol- Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5547967A (en) * | 1993-12-08 | 1996-08-20 | Kali-Chemie Pharma Gmbh | (Phenylalkylaminoalkyloxy)-heteroaryl-compounds, processes and intermediates for their production and pharmaceutical compositions containing them |
| GB9824310D0 (en) * | 1998-11-05 | 1998-12-30 | Univ London | Activators of soluble guanylate cyclase |
| US6492529B1 (en) | 2000-01-18 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Bis pyrazole-1H-pyrazole intermediates and their synthesis |
| AU2002308748A1 (en) | 2001-05-16 | 2002-11-25 | Vertex Pharmaceuticals Incorporated | Heterocyclic substituted pyrazoles as inhibitors of src and other protein kinases |
| WO2002102387A1 (en) | 2001-06-18 | 2002-12-27 | H. Lundbeck A/S | Treatment of neuropathic pain |
| EP1534680B1 (en) | 2002-08-14 | 2012-02-22 | Pharmaco Investments, Inc. | Prenylation inhibitors and methods of their synthesis and use |
| TW200413351A (en) | 2002-08-21 | 2004-08-01 | Astrazeneca Ab | Chemical compounds |
| WO2005023247A1 (en) * | 2003-09-03 | 2005-03-17 | Smithkline Beecham Corporation | Compounds and methods |
| WO2005061470A1 (en) * | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| ATE452134T1 (de) * | 2004-08-09 | 2010-01-15 | Abbott Gmbh & Co Kg | Zur behandlung von auf eine modulation des dopamin-d3-rezeptors ansprechende erkrankungen geeignete 4-piperazinylpyrimidinverbindungen |
| US7696199B2 (en) * | 2004-08-27 | 2010-04-13 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
| JP2009528315A (ja) * | 2006-03-01 | 2009-08-06 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | シグマ受容体阻害剤としてのピラゾール誘導体 |
-
2006
- 2006-03-02 EP EP06004198A patent/EP1829866A1/en not_active Withdrawn
-
2007
- 2007-03-02 CA CA002640753A patent/CA2640753A1/en not_active Abandoned
- 2007-03-02 EP EP07723021A patent/EP1996554B1/en not_active Not-in-force
- 2007-03-02 WO PCT/EP2007/001826 patent/WO2007098963A1/en not_active Ceased
- 2007-03-02 MX MX2008011018A patent/MX2008011018A/es active IP Right Grant
- 2007-03-02 ES ES07723021T patent/ES2392193T3/es active Active
- 2007-03-02 JP JP2008556725A patent/JP2009528317A/ja active Pending
- 2007-03-02 CN CN2007800074821A patent/CN101395138B/zh not_active Expired - Fee Related
- 2007-03-02 US US12/281,314 patent/US8088812B2/en not_active Expired - Fee Related
- 2007-03-02 PT PT07723021T patent/PT1996554E/pt unknown
-
2011
- 2011-11-14 US US13/295,315 patent/US20120059006A1/en not_active Abandoned
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