JP2005518371A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005518371A5 JP2005518371A5 JP2003550753A JP2003550753A JP2005518371A5 JP 2005518371 A5 JP2005518371 A5 JP 2005518371A5 JP 2003550753 A JP2003550753 A JP 2003550753A JP 2003550753 A JP2003550753 A JP 2003550753A JP 2005518371 A5 JP2005518371 A5 JP 2005518371A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- membered
- substituted
- dihydro
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 3230
- 125000005843 halogen group Chemical group 0.000 claims 340
- 229910052760 oxygen Inorganic materials 0.000 claims 312
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 288
- 125000004093 cyano group Chemical group *C#N 0.000 claims 281
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 279
- 229920006395 saturated elastomer Polymers 0.000 claims 235
- 229910052717 sulfur Inorganic materials 0.000 claims 221
- 125000004429 atom Chemical group 0.000 claims 218
- 229910052799 carbon Inorganic materials 0.000 claims 218
- 125000001424 substituent group Chemical group 0.000 claims 191
- 150000001875 compounds Chemical class 0.000 claims 175
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 129
- 229910052757 nitrogen Inorganic materials 0.000 claims 126
- 125000001188 haloalkyl group Chemical group 0.000 claims 124
- -1 3-nitrophenyl Chemical group 0.000 claims 116
- 229910052739 hydrogen Inorganic materials 0.000 claims 105
- 125000004432 carbon atom Chemical group C* 0.000 claims 83
- 125000004430 oxygen atom Chemical group O* 0.000 claims 82
- 125000004434 sulfur atom Chemical group 0.000 claims 82
- 125000000623 heterocyclic group Chemical group 0.000 claims 80
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 72
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 69
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 58
- 125000004043 oxo group Chemical group O=* 0.000 claims 56
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 55
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 40
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 38
- 125000002619 bicyclic group Chemical group 0.000 claims 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 34
- 150000001721 carbon Chemical group 0.000 claims 33
- 125000005842 heteroatom Chemical group 0.000 claims 31
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims 30
- 125000002950 monocyclic group Chemical group 0.000 claims 29
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 20
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 15
- 230000002757 inflammatory effect Effects 0.000 claims 15
- 125000001624 naphthyl group Chemical group 0.000 claims 13
- JWPMHRXIIOEZRU-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole Chemical compound C1NC=NS1 JWPMHRXIIOEZRU-UHFFFAOYSA-N 0.000 claims 12
- 208000004454 Hyperalgesia Diseases 0.000 claims 12
- 208000002193 Pain Diseases 0.000 claims 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 12
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 11
- 125000005605 benzo group Chemical group 0.000 claims 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- HBJUQLMVCIEESP-UHFFFAOYSA-N 2,5-dihydro-1,2,4-oxadiazole Chemical compound C1NC=NO1 HBJUQLMVCIEESP-UHFFFAOYSA-N 0.000 claims 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 208000004296 neuralgia Diseases 0.000 claims 9
- 208000021722 neuropathic pain Diseases 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 230000002792 vascular Effects 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 230000002496 gastric effect Effects 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 6
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 6
- JRLFRFTXXMZSND-UHFFFAOYSA-N 1,2,4-triazoline Chemical compound C1NNC=N1 JRLFRFTXXMZSND-UHFFFAOYSA-N 0.000 claims 6
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims 6
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical compound C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 claims 6
- PNJBXRVMRQIFKK-UHFFFAOYSA-N 1,4-dihydrotriazine Chemical compound C1C=CNN=N1 PNJBXRVMRQIFKK-UHFFFAOYSA-N 0.000 claims 6
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims 6
- CQHHFSBXAPCQFG-UHFFFAOYSA-N 2,3-dihydro-1,2,4-oxadiazole Chemical compound C1NOC=N1 CQHHFSBXAPCQFG-UHFFFAOYSA-N 0.000 claims 6
- ALBVNKOEWADZPF-UHFFFAOYSA-N 2,3-dihydro-1,2,4-thiadiazole Chemical compound C1NSC=N1 ALBVNKOEWADZPF-UHFFFAOYSA-N 0.000 claims 6
- IIATVLXXAYLQIZ-UHFFFAOYSA-N 2,5-dihydro-1,2,4-triazine Chemical compound C1C=NNC=N1 IIATVLXXAYLQIZ-UHFFFAOYSA-N 0.000 claims 6
- KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 claims 6
- 208000035154 Hyperesthesia Diseases 0.000 claims 6
- 206010065390 Inflammatory pain Diseases 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- 206010053552 allodynia Diseases 0.000 claims 6
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 6
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 6
- 208000011580 syndromic disease Diseases 0.000 claims 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 4
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 4
- USSYLANTAAUELR-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazine Chemical compound N1NC=NC=C1 USSYLANTAAUELR-UHFFFAOYSA-N 0.000 claims 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 230000005856 abnormality Effects 0.000 claims 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 4
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims 3
- JQIZHNLEFQMDCQ-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridazine Chemical compound C1CC=CNN1 JQIZHNLEFQMDCQ-UHFFFAOYSA-N 0.000 claims 3
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 3
- JZTKNVMVUVSGJF-UHFFFAOYSA-N 1,2,3,5-oxatriazole Chemical compound C=1N=NON=1 JZTKNVMVUVSGJF-UHFFFAOYSA-N 0.000 claims 3
- XLEDBLKSWOYHES-UHFFFAOYSA-N 1,2,3,5-thiatriazole Chemical compound C=1N=NSN=1 XLEDBLKSWOYHES-UHFFFAOYSA-N 0.000 claims 3
- IOLQWFQLCNMKAZ-UHFFFAOYSA-N 1,2,3,6-tetrahydropyrazine Chemical compound C1CN=CCN1 IOLQWFQLCNMKAZ-UHFFFAOYSA-N 0.000 claims 3
- WNSPCCWAAVHWIM-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridazine Chemical compound C1NNCC=C1 WNSPCCWAAVHWIM-UHFFFAOYSA-N 0.000 claims 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 3
- BLWJJPNXUDWVCG-UHFFFAOYSA-N 1,2,4-oxadiazolidine Chemical compound C1NCON1 BLWJJPNXUDWVCG-UHFFFAOYSA-N 0.000 claims 3
- YFCCVJQVYQHMOG-UHFFFAOYSA-N 1,2,4-thiadiazolidine Chemical compound C1NCSN1 YFCCVJQVYQHMOG-UHFFFAOYSA-N 0.000 claims 3
- WNBQDDAKLKODPH-UHFFFAOYSA-N 1,2,4-triazolidine Chemical compound C1NCNN1 WNBQDDAKLKODPH-UHFFFAOYSA-N 0.000 claims 3
- OHFXUPDPPRJZES-UHFFFAOYSA-N 1,2,5,6-tetrahydropyrimidine Chemical compound C1CC=NCN1 OHFXUPDPPRJZES-UHFFFAOYSA-N 0.000 claims 3
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims 3
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 3
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims 3
- NTSJGNVMDZAPJE-UHFFFAOYSA-N 1,2-dihydrotriazine Chemical compound N1NN=CC=C1 NTSJGNVMDZAPJE-UHFFFAOYSA-N 0.000 claims 3
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 3
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 3
- SKLDBJVFTOQKHE-UHFFFAOYSA-N 1,3,4-oxadiazolidine Chemical compound C1NNCO1 SKLDBJVFTOQKHE-UHFFFAOYSA-N 0.000 claims 3
- NWEFQXYVAUNGNI-UHFFFAOYSA-N 1,3,4-oxathiazolidine Chemical compound C1NSCO1 NWEFQXYVAUNGNI-UHFFFAOYSA-N 0.000 claims 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 3
- BRQBVEHLEITSPT-UHFFFAOYSA-N 1,3,4-thiadiazolidine Chemical compound C1NNCS1 BRQBVEHLEITSPT-UHFFFAOYSA-N 0.000 claims 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 3
- UKOMUVPFRFPHDS-UHFFFAOYSA-N 1,4,2-dioxazine Chemical compound O1C=CON=C1 UKOMUVPFRFPHDS-UHFFFAOYSA-N 0.000 claims 3
- DDGWEFMIIOIMEF-UHFFFAOYSA-N 1,4,2-dithiazine Chemical compound S1C=CSN=C1 DDGWEFMIIOIMEF-UHFFFAOYSA-N 0.000 claims 3
- FMYSHKHSQFXYRS-UHFFFAOYSA-N 1,4,2-oxathiazine Chemical compound O1C=CSC=N1 FMYSHKHSQFXYRS-UHFFFAOYSA-N 0.000 claims 3
- GWOPJRXEMFYVQP-UHFFFAOYSA-N 1,4,2-oxathiazolidine Chemical compound C1NOCS1 GWOPJRXEMFYVQP-UHFFFAOYSA-N 0.000 claims 3
- BGMLUCPALPKNOV-UHFFFAOYSA-N 1,4,5,6-tetrahydropyridazine Chemical compound C1CNN=CC1 BGMLUCPALPKNOV-UHFFFAOYSA-N 0.000 claims 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 3
- XYNBEQAWBCGIMD-UHFFFAOYSA-N 1,4-dihydropyrazine Chemical compound N1C=CNC=C1 XYNBEQAWBCGIMD-UHFFFAOYSA-N 0.000 claims 3
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical compound C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 claims 3
- OKGNMRKOGWTADH-UHFFFAOYSA-N 1,4-dihydropyrimidine Chemical compound C1C=CNC=N1 OKGNMRKOGWTADH-UHFFFAOYSA-N 0.000 claims 3
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 claims 3
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 claims 3
- CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 claims 3
- QFXRFFKVJYBGLQ-UHFFFAOYSA-N 1,6-dihydro-1,2,4-triazine Chemical compound C1NN=CN=C1 QFXRFFKVJYBGLQ-UHFFFAOYSA-N 0.000 claims 3
- ZEFGUWRQFNTGGX-UHFFFAOYSA-N 1,6-dihydropyridazine Chemical compound C1NN=CC=C1 ZEFGUWRQFNTGGX-UHFFFAOYSA-N 0.000 claims 3
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 3
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims 3
- GRYYTSJXIFGRAL-UHFFFAOYSA-N 2,3-dihydro-1,2,4-triazine Chemical compound C1NN=CC=N1 GRYYTSJXIFGRAL-UHFFFAOYSA-N 0.000 claims 3
- FJRPOHLDJUJARI-UHFFFAOYSA-N 2,3-dihydro-1,2-oxazole Chemical compound C1NOC=C1 FJRPOHLDJUJARI-UHFFFAOYSA-N 0.000 claims 3
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 claims 3
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims 3
- VKRGLHLCUMMXHA-UHFFFAOYSA-N 2,3-dihydro-1,3,4-thiadiazole Chemical compound C1NN=CS1 VKRGLHLCUMMXHA-UHFFFAOYSA-N 0.000 claims 3
- ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical compound C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 claims 3
- OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 claims 3
- AXYMXGSRCWCVIK-UHFFFAOYSA-N 2,3-dihydro-1,4,2-dioxazine Chemical compound C1NOC=CO1 AXYMXGSRCWCVIK-UHFFFAOYSA-N 0.000 claims 3
- RTQGSDHQFAONPG-UHFFFAOYSA-N 2,3-dihydro-1,4,3-oxathiazine Chemical compound C1NSC=CO1 RTQGSDHQFAONPG-UHFFFAOYSA-N 0.000 claims 3
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 3
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 3
- WUCWFMVYIKMAPG-UHFFFAOYSA-N 2,3-dihydropyrazine Chemical compound C1CN=CC=N1 WUCWFMVYIKMAPG-UHFFFAOYSA-N 0.000 claims 3
- NZHIIDNOLFOHSG-UHFFFAOYSA-N 2,3-dihydropyridine Chemical compound C1CN=CC=C1 NZHIIDNOLFOHSG-UHFFFAOYSA-N 0.000 claims 3
- NHZLLKNRTDIFAD-UHFFFAOYSA-N 2,5-dihydro-1,3-oxazole Chemical compound C1OCN=C1 NHZLLKNRTDIFAD-UHFFFAOYSA-N 0.000 claims 3
- JLPUISACQXFVRC-UHFFFAOYSA-N 2,5-dihydro-1,3-thiazole Chemical compound C1SCN=C1 JLPUISACQXFVRC-UHFFFAOYSA-N 0.000 claims 3
- FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical compound C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 claims 3
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims 3
- BNDCYQXUFIHUHS-UHFFFAOYSA-N 2,5-dihydropyrazine Chemical compound C1C=NCC=N1 BNDCYQXUFIHUHS-UHFFFAOYSA-N 0.000 claims 3
- WRLAXLNSBDVNRL-UHFFFAOYSA-N 2,5-dihydropyrimidine Chemical compound C1C=NCN=C1 WRLAXLNSBDVNRL-UHFFFAOYSA-N 0.000 claims 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 3
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 3
- HCNVXDPRTRLNFX-UHFFFAOYSA-N 2h-1,3,4-oxadiazine Chemical compound C1OC=CN=N1 HCNVXDPRTRLNFX-UHFFFAOYSA-N 0.000 claims 3
- KLVQAIJZDCCJRZ-UHFFFAOYSA-N 2h-1,3,4-thiadiazine Chemical compound C1SC=CN=N1 KLVQAIJZDCCJRZ-UHFFFAOYSA-N 0.000 claims 3
- PZOJXKYWPGPWQC-UHFFFAOYSA-N 2h-1,3,5-oxadiazine Chemical compound C1OC=NC=N1 PZOJXKYWPGPWQC-UHFFFAOYSA-N 0.000 claims 3
- VNXIZDXJEGBXRQ-UHFFFAOYSA-N 2h-1,3,5-thiadiazine Chemical compound C1SC=NC=N1 VNXIZDXJEGBXRQ-UHFFFAOYSA-N 0.000 claims 3
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 3
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims 3
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 3
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims 3
- QMDFJHAAWUGVKQ-UHFFFAOYSA-N 2h-thiopyran Chemical compound C1SC=CC=C1 QMDFJHAAWUGVKQ-UHFFFAOYSA-N 0.000 claims 3
- LIYUKZAZFWIJPB-UHFFFAOYSA-N 3,4-dihydro-2h-1,3,4-thiadiazine Chemical compound C1NNC=CS1 LIYUKZAZFWIJPB-UHFFFAOYSA-N 0.000 claims 3
- GNNHQRGDLMQALS-UHFFFAOYSA-N 3,4-dihydro-2h-1,3,5-thiadiazine Chemical compound C1NCN=CS1 GNNHQRGDLMQALS-UHFFFAOYSA-N 0.000 claims 3
- NLXFKDHULKLENC-UHFFFAOYSA-N 3,4-dihydro-2h-1,3-oxazine Chemical compound C1NCC=CO1 NLXFKDHULKLENC-UHFFFAOYSA-N 0.000 claims 3
- BOLMDIXLULGTBD-UHFFFAOYSA-N 3,4-dihydro-2h-oxazine Chemical compound C1CC=CON1 BOLMDIXLULGTBD-UHFFFAOYSA-N 0.000 claims 3
- NWWJFMCCTZLKNT-UHFFFAOYSA-N 3,4-dihydro-2h-thiazine Chemical compound C1CC=CSN1 NWWJFMCCTZLKNT-UHFFFAOYSA-N 0.000 claims 3
- ATVJJNGVPSKBGO-UHFFFAOYSA-N 3,4-dihydro-2h-thiopyran Chemical compound C1CSC=CC1 ATVJJNGVPSKBGO-UHFFFAOYSA-N 0.000 claims 3
- RDOAUPPSCNSYPM-UHFFFAOYSA-N 3,4-dihydropyridine Chemical compound C1CC=NC=C1 RDOAUPPSCNSYPM-UHFFFAOYSA-N 0.000 claims 3
- LPHWCAUEPAUFHZ-UHFFFAOYSA-N 3,6-Dihydropyridine Chemical compound C1C=CCN=C1 LPHWCAUEPAUFHZ-UHFFFAOYSA-N 0.000 claims 3
- MUYVJODFVRCAOF-UHFFFAOYSA-N 3,6-dihydro-1,2,4-triazine Chemical compound C1C=NCN=N1 MUYVJODFVRCAOF-UHFFFAOYSA-N 0.000 claims 3
- YFGWHNJRWZLMPC-UHFFFAOYSA-N 3,6-dihydro-2h-1,2,5-thiadiazine Chemical compound C1NSCN=C1 YFGWHNJRWZLMPC-UHFFFAOYSA-N 0.000 claims 3
- AMKVFOFJZLHHDC-UHFFFAOYSA-N 3,6-dihydro-2h-1,3,4-thiadiazine Chemical compound C1NN=CCS1 AMKVFOFJZLHHDC-UHFFFAOYSA-N 0.000 claims 3
- GPAZGRQYFCWGOO-UHFFFAOYSA-N 3,6-dihydro-2h-1,3,5-thiadiazine Chemical compound C1NC=NCS1 GPAZGRQYFCWGOO-UHFFFAOYSA-N 0.000 claims 3
- RUPLWPYHVWSFEF-UHFFFAOYSA-N 3,6-dihydro-2h-1,3-oxazine Chemical compound C1NC=CCO1 RUPLWPYHVWSFEF-UHFFFAOYSA-N 0.000 claims 3
- DNUJVGBNIXGTHC-UHFFFAOYSA-N 3,6-dihydro-2h-oxazine Chemical compound C1NOCC=C1 DNUJVGBNIXGTHC-UHFFFAOYSA-N 0.000 claims 3
- SGDYNMJTXCTTAF-UHFFFAOYSA-N 3,6-dihydro-2h-thiazine Chemical compound C1NSCC=C1 SGDYNMJTXCTTAF-UHFFFAOYSA-N 0.000 claims 3
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims 3
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 3
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims 3
- BKYIMUSAVMSMGK-UHFFFAOYSA-N 4,5-dihydropyridazine Chemical compound C1CC=NN=C1 BKYIMUSAVMSMGK-UHFFFAOYSA-N 0.000 claims 3
- BBZZGDLNBVRFFI-UHFFFAOYSA-N 4,5-dihydropyrimidine Chemical compound C1CN=CN=C1 BBZZGDLNBVRFFI-UHFFFAOYSA-N 0.000 claims 3
- ZTPBNDYYCCGCGD-UHFFFAOYSA-N 4,5-dihydrotriazine Chemical compound C1CN=NN=C1 ZTPBNDYYCCGCGD-UHFFFAOYSA-N 0.000 claims 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 claims 3
- NGUCKHVSIWZIPQ-UHFFFAOYSA-N 4h-1,2,5-oxadiazine Chemical compound C1C=NOC=N1 NGUCKHVSIWZIPQ-UHFFFAOYSA-N 0.000 claims 3
- QBMIYRSEKPGOJY-UHFFFAOYSA-N 4h-1,3,4-oxadiazine Chemical compound N1C=COC=N1 QBMIYRSEKPGOJY-UHFFFAOYSA-N 0.000 claims 3
- AVHCHJKMIGPLIZ-UHFFFAOYSA-N 4h-1,3,4-thiadiazine Chemical compound N1C=CSC=N1 AVHCHJKMIGPLIZ-UHFFFAOYSA-N 0.000 claims 3
- LPWMFGGUZLCGBF-UHFFFAOYSA-N 4h-1,3,5-oxadiazine Chemical compound C1N=COC=N1 LPWMFGGUZLCGBF-UHFFFAOYSA-N 0.000 claims 3
- QLOAZIIJBGXVDN-UHFFFAOYSA-N 4h-1,3,5-thiadiazine Chemical compound C1N=CSC=N1 QLOAZIIJBGXVDN-UHFFFAOYSA-N 0.000 claims 3
- UOSQFVCDJBZRKS-UHFFFAOYSA-N 4h-1,4-oxazine Chemical compound N1C=COC=C1 UOSQFVCDJBZRKS-UHFFFAOYSA-N 0.000 claims 3
- ZOXMLSDKXHNVOQ-UHFFFAOYSA-N 4h-1,4-thiazine Chemical compound N1C=CSC=C1 ZOXMLSDKXHNVOQ-UHFFFAOYSA-N 0.000 claims 3
- BMRPOOWUTVUBRI-UHFFFAOYSA-N 4h-oxazine Chemical compound C1C=CON=C1 BMRPOOWUTVUBRI-UHFFFAOYSA-N 0.000 claims 3
- XZMWWZZCMGYPHD-UHFFFAOYSA-N 4h-thiazine Chemical compound C1C=CSN=C1 XZMWWZZCMGYPHD-UHFFFAOYSA-N 0.000 claims 3
- STBGWNRZMPCVTG-UHFFFAOYSA-N 4h-thiopyran Chemical compound C1C=CSC=C1 STBGWNRZMPCVTG-UHFFFAOYSA-N 0.000 claims 3
- VNOMHCXUKPUGJE-UHFFFAOYSA-N 5,6-dihydro-1,2,4-triazine Chemical compound C1CN=NC=N1 VNOMHCXUKPUGJE-UHFFFAOYSA-N 0.000 claims 3
- SGVDPBAZOBRHRE-UHFFFAOYSA-N 5,6-dihydro-1,4,2-dithiazine Chemical compound C1CSN=CS1 SGVDPBAZOBRHRE-UHFFFAOYSA-N 0.000 claims 3
- VXBRQDSRTRLHPJ-UHFFFAOYSA-N 5,6-dihydro-1,4,2-oxathiazine Chemical compound C1CSC=NO1 VXBRQDSRTRLHPJ-UHFFFAOYSA-N 0.000 claims 3
- QUJTVGHTSQMUMV-UHFFFAOYSA-N 5,6-dihydro-1,4,3-oxathiazine Chemical compound C1CSN=CO1 QUJTVGHTSQMUMV-UHFFFAOYSA-N 0.000 claims 3
- OWKSGFQMLODDJJ-UHFFFAOYSA-N 5,6-dihydro-2h-1,2,5-thiadiazine Chemical compound C1NC=CNS1 OWKSGFQMLODDJJ-UHFFFAOYSA-N 0.000 claims 3
- UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical compound C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 claims 3
- MXDHUJDGSBTOTI-UHFFFAOYSA-N 5,6-dihydro-2h-thiadiazine Chemical compound C1CC=NNS1 MXDHUJDGSBTOTI-UHFFFAOYSA-N 0.000 claims 3
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical compound C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 claims 3
- OXHGKAXWARAOPZ-UHFFFAOYSA-N 5,6-dihydro-4h-1,2,5-thiadiazine Chemical compound C1NCC=NS1 OXHGKAXWARAOPZ-UHFFFAOYSA-N 0.000 claims 3
- ZQNUENDKDTXKSU-UHFFFAOYSA-N 5,6-dihydro-4h-1,3,4-thiadiazine Chemical compound C1CSC=NN1 ZQNUENDKDTXKSU-UHFFFAOYSA-N 0.000 claims 3
- YWOIQIYQBRDOQA-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-oxazine Chemical compound C1COC=NC1 YWOIQIYQBRDOQA-UHFFFAOYSA-N 0.000 claims 3
- BYVSMDBDTBXASR-UHFFFAOYSA-N 5,6-dihydro-4h-oxazine Chemical compound C1CON=CC1 BYVSMDBDTBXASR-UHFFFAOYSA-N 0.000 claims 3
- WSXNRJXPTNQJBH-UHFFFAOYSA-N 5,6-dihydro-4h-thiazine Chemical compound C1CSN=CC1 WSXNRJXPTNQJBH-UHFFFAOYSA-N 0.000 claims 3
- MIOUOWAIZBEKFY-UHFFFAOYSA-N 6h-1,2,5-oxadiazine Chemical compound C1ON=CC=N1 MIOUOWAIZBEKFY-UHFFFAOYSA-N 0.000 claims 3
- BMZKZBWPMWEQAY-UHFFFAOYSA-N 6h-1,2,5-thiadiazine Chemical compound C1SN=CC=N1 BMZKZBWPMWEQAY-UHFFFAOYSA-N 0.000 claims 3
- BTSRCKGXYLBFOS-UHFFFAOYSA-N 6h-1,3,4-oxadiazine Chemical compound C1OC=NN=C1 BTSRCKGXYLBFOS-UHFFFAOYSA-N 0.000 claims 3
- BJZFKUQYNPYBGE-UHFFFAOYSA-N 6h-1,3,4-thiadiazine Chemical compound C1SC=NN=C1 BJZFKUQYNPYBGE-UHFFFAOYSA-N 0.000 claims 3
- GMLMFZXBPRIXPK-UHFFFAOYSA-N 6h-1,3-oxazine Chemical compound C1OC=NC=C1 GMLMFZXBPRIXPK-UHFFFAOYSA-N 0.000 claims 3
- VNCVSCGVODHWLX-UHFFFAOYSA-N 6h-1,3-thiazine Chemical compound C1SC=NC=C1 VNCVSCGVODHWLX-UHFFFAOYSA-N 0.000 claims 3
- QFPDHKBNCJAOKJ-UHFFFAOYSA-N 6h-oxazine Chemical compound C1ON=CC=C1 QFPDHKBNCJAOKJ-UHFFFAOYSA-N 0.000 claims 3
- DLNUKTLHURJVDF-UHFFFAOYSA-N 6h-thiazine Chemical compound C1SN=CC=C1 DLNUKTLHURJVDF-UHFFFAOYSA-N 0.000 claims 3
- CCVRDKFBCDVQBY-UHFFFAOYSA-N C1NC=CN=N1 Chemical compound C1NC=CN=N1 CCVRDKFBCDVQBY-UHFFFAOYSA-N 0.000 claims 3
- 208000006561 Cluster Headache Diseases 0.000 claims 3
- 206010012434 Dermatitis allergic Diseases 0.000 claims 3
- 206010012735 Diarrhoea Diseases 0.000 claims 3
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 3
- 208000002111 Eye Abnormalities Diseases 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 206010019233 Headaches Diseases 0.000 claims 3
- 208000009889 Herpes Simplex Diseases 0.000 claims 3
- 206010020853 Hypertonic bladder Diseases 0.000 claims 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 206010028851 Necrosis Diseases 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- 208000003251 Pruritus Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 208000025747 Rheumatic disease Diseases 0.000 claims 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims 3
- 206010043269 Tension headache Diseases 0.000 claims 3
- 208000008548 Tension-Type Headache Diseases 0.000 claims 3
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 3
- 208000025865 Ulcer Diseases 0.000 claims 3
- 206010047642 Vitiligo Diseases 0.000 claims 3
- 206010052428 Wound Diseases 0.000 claims 3
- 208000027418 Wounds and injury Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 208000005298 acute pain Diseases 0.000 claims 3
- 201000010105 allergic rhinitis Diseases 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 208000018912 cluster headache syndrome Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 208000000718 duodenal ulcer Diseases 0.000 claims 3
- 210000000981 epithelium Anatomy 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 230000003779 hair growth Effects 0.000 claims 3
- 231100000869 headache Toxicity 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 3
- 230000004968 inflammatory condition Effects 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 230000004899 motility Effects 0.000 claims 3
- 230000017074 necrotic cell death Effects 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 claims 3
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 3
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 230000000241 respiratory effect Effects 0.000 claims 3
- 208000017520 skin disease Diseases 0.000 claims 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 3
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims 3
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- 230000000451 tissue damage Effects 0.000 claims 3
- 231100000827 tissue damage Toxicity 0.000 claims 3
- 230000009092 tissue dysfunction Effects 0.000 claims 3
- 230000036269 ulceration Effects 0.000 claims 3
- 230000001457 vasomotor Effects 0.000 claims 3
- 208000001319 vasomotor rhinitis Diseases 0.000 claims 3
- 230000009278 visceral effect Effects 0.000 claims 3
- GBLQGXFTPLQBTA-UHFFFAOYSA-N 1,2,3-triazoline Chemical compound C1CN=NN1 GBLQGXFTPLQBTA-UHFFFAOYSA-N 0.000 claims 2
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 2
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- APLXYWOZCKOSMG-UHFFFAOYSA-N 3,4-dihydro-2h-1,2,5-thiadiazine Chemical compound C1CN=CSN1 APLXYWOZCKOSMG-UHFFFAOYSA-N 0.000 claims 2
- HMOBRUPKXAKFHS-UHFFFAOYSA-N 4,4-dimethyl-1,3-dihydroquinolin-2-one Chemical compound C1=CC=C2C(C)(C)CC(=O)NC2=C1 HMOBRUPKXAKFHS-UHFFFAOYSA-N 0.000 claims 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
- CQBVDZLLODTOAS-UHFFFAOYSA-N 4h-1,2,5-thiadiazine Chemical compound C1C=NSC=N1 CQBVDZLLODTOAS-UHFFFAOYSA-N 0.000 claims 2
- RLDJTWKQIMTLEN-UHFFFAOYSA-N 5,6-dihydro-1,4,2-dioxazine Chemical compound C1CON=CO1 RLDJTWKQIMTLEN-UHFFFAOYSA-N 0.000 claims 2
- LUSYNJGQFRRKIA-UHFFFAOYSA-N 5,6-dihydro-2h-1,3-oxazine Chemical compound C1CC=NCO1 LUSYNJGQFRRKIA-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000014181 Bronchial disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- BDURTBMDULENEE-UHFFFAOYSA-N S1NC=CC1.O1NC=CC1 Chemical compound S1NC=CC1.O1NC=CC1 BDURTBMDULENEE-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 208000029162 bladder disease Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- BIDAKHHAMURWJQ-UHFFFAOYSA-N cyclopenta[b]thiopyran Chemical compound C1=CSC2=CC=CC2=C1 BIDAKHHAMURWJQ-UHFFFAOYSA-N 0.000 claims 2
- WITCGPMUKHXQGW-UHFFFAOYSA-N cyclopenta[c]thiopyran Chemical compound C1=CSC=C2C=CC=C21 WITCGPMUKHXQGW-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 2
- AYFPGVWCUMGFSR-JLHYYAGUSA-N (3-methoxyphenyl) (e)-3-(4-tert-butylphenyl)prop-2-enoate Chemical compound COC1=CC=CC(OC(=O)\C=C\C=2C=CC(=CC=2)C(C)(C)C)=C1 AYFPGVWCUMGFSR-JLHYYAGUSA-N 0.000 claims 1
- JZPGOILTIFPJPY-FLIBITNWSA-N (Z)-3-(4-tert-butylphenyl)-3-iodoprop-2-enamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)/C(=C/C(=O)N)/I JZPGOILTIFPJPY-FLIBITNWSA-N 0.000 claims 1
- VGPLGKJGLDHRKC-KPKJPENVSA-N (e)-3-(4-tert-butylphenyl)-n-(1-methylindol-5-yl)prop-2-enamide Chemical compound C=1C=C2N(C)C=CC2=CC=1NC(=O)\C=C\C1=CC=C(C(C)(C)C)C=C1 VGPLGKJGLDHRKC-KPKJPENVSA-N 0.000 claims 1
- WNUQFSSLBYZXJB-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-(2,3-dihydro-1h-indol-6-yl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(CCN2)C2=C1 WNUQFSSLBYZXJB-IZZDOVSWSA-N 0.000 claims 1
- GXKPMXKEYHOACC-MDWZMJQESA-N (e)-3-(4-tert-butylphenyl)-n-(3,4-dimethoxyphenyl)prop-2-enamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)\C=C\C1=CC=C(C(C)(C)C)C=C1 GXKPMXKEYHOACC-MDWZMJQESA-N 0.000 claims 1
- YAJHKMMLZHZIMZ-FMIVXFBMSA-N (e)-3-(4-tert-butylphenyl)-n-(3-hydroxyphenyl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC(O)=C1 YAJHKMMLZHZIMZ-FMIVXFBMSA-N 0.000 claims 1
- GMSBZMYGYHLZCR-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-[1-(2-hydroxyethyl)indol-5-yl]prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(N(CCO)C=C2)C2=C1 GMSBZMYGYHLZCR-IZZDOVSWSA-N 0.000 claims 1
- KHKHYEWCOLLFKV-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-[1-(2-hydroxyethyl)indol-6-yl]prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(C=CN2CCO)C2=C1 KHKHYEWCOLLFKV-IZZDOVSWSA-N 0.000 claims 1
- FDXNOQODXBEQMX-KPKJPENVSA-N (e)-3-(4-tert-butylphenyl)-n-[1-(2-methoxyethyl)indol-5-yl]prop-2-enamide Chemical compound C=1C=C2N(CCOC)C=CC2=CC=1NC(=O)\C=C\C1=CC=C(C(C)(C)C)C=C1 FDXNOQODXBEQMX-KPKJPENVSA-N 0.000 claims 1
- VORXJEYZJGKHJT-KPKJPENVSA-N (e)-3-(4-tert-butylphenyl)-n-[1-(2-methoxyethyl)indol-6-yl]prop-2-enamide Chemical compound C1=C2N(CCOC)C=CC2=CC=C1NC(=O)\C=C\C1=CC=C(C(C)(C)C)C=C1 VORXJEYZJGKHJT-KPKJPENVSA-N 0.000 claims 1
- LKMUYFJTLVTRPL-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-[2-(hydroxymethyl)-1h-indol-5-yl]prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(NC(CO)=C2)C2=C1 LKMUYFJTLVTRPL-IZZDOVSWSA-N 0.000 claims 1
- OFHMNTWCPPZKHO-FMIVXFBMSA-N (e)-3-(4-tert-butylphenyl)-n-[3-(2-hydroxyethoxy)phenyl]prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC(OCCO)=C1 OFHMNTWCPPZKHO-FMIVXFBMSA-N 0.000 claims 1
- NQVKUNVGKKIELF-DTQAZKPQSA-N (e)-3-(4-tert-butylphenyl)-n-[3-[2-(1,3-dioxoisoindol-2-yl)ethoxy]phenyl]prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC(OCCN2C(C3=CC=CC=C3C2=O)=O)=C1 NQVKUNVGKKIELF-DTQAZKPQSA-N 0.000 claims 1
- WRGYDQRVDKMWOR-KPKJPENVSA-N (e)-3-(4-tert-butylphenyl)-n-[4-chloro-3-(methylcarbamoylamino)phenyl]prop-2-enamide Chemical compound C1=C(Cl)C(NC(=O)NC)=CC(NC(=O)\C=C\C=2C=CC(=CC=2)C(C)(C)C)=C1 WRGYDQRVDKMWOR-KPKJPENVSA-N 0.000 claims 1
- AVMIAJAOFXDOSN-SDNWHVSQSA-N (e)-3-(4-tert-butylphenyl)-n-phenylprop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC=C1 AVMIAJAOFXDOSN-SDNWHVSQSA-N 0.000 claims 1
- VHAXLKCWSVBCSH-IZZDOVSWSA-N (e)-3-(4-tert-butylphenyl)-n-quinoxalin-6-ylprop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(N=CC=N2)C2=C1 VHAXLKCWSVBCSH-IZZDOVSWSA-N 0.000 claims 1
- TZOVPSUEQYGATA-UXBLZVDNSA-N (e)-3-(6-tert-butyl-2-methylpyridin-3-yl)-n-(1h-indol-5-yl)prop-2-enamide Chemical compound CC1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 TZOVPSUEQYGATA-UXBLZVDNSA-N 0.000 claims 1
- MMNOSTLHPZKCGI-JXMROGBWSA-N (e)-3-(6-tert-butyl-2-methylpyridin-3-yl)-n-(1h-indol-6-yl)prop-2-enamide Chemical compound CC1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(C=CN2)C2=C1 MMNOSTLHPZKCGI-JXMROGBWSA-N 0.000 claims 1
- YCAJIDBYOJYWEZ-UXBLZVDNSA-N (e)-3-(6-tert-butyl-2-methylpyridin-3-yl)-n-[2-(hydroxymethyl)-1h-indol-5-yl]prop-2-enamide Chemical compound CC1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(NC(CO)=C2)C2=C1 YCAJIDBYOJYWEZ-UXBLZVDNSA-N 0.000 claims 1
- FFHNKHYNDWLHTE-WEVVVXLNSA-N (e)-3-(6-tert-butylpyridin-3-yl)-n-[1-(2-hydroxyethyl)indol-5-yl]prop-2-enamide Chemical compound C1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(N(CCO)C=C2)C2=C1 FFHNKHYNDWLHTE-WEVVVXLNSA-N 0.000 claims 1
- SKBVAGKWEVXLIN-WEVVVXLNSA-N (e)-3-(6-tert-butylpyridin-3-yl)-n-[2-(hydroxymethyl)-1h-indol-5-yl]prop-2-enamide Chemical compound C1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(NC(CO)=C2)C2=C1 SKBVAGKWEVXLIN-WEVVVXLNSA-N 0.000 claims 1
- FZXHUTVUNWTZMP-QHHAFSJGSA-N (e)-3-[2,3-difluoro-4-(trifluoromethyl)phenyl]-n-(1h-indol-5-yl)prop-2-enamide Chemical compound FC1=C(F)C(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 FZXHUTVUNWTZMP-QHHAFSJGSA-N 0.000 claims 1
- IPSKRGZEAGQLMG-QHHAFSJGSA-N (e)-3-[2,4-bis(trifluoromethyl)phenyl]-n-(1h-indol-5-yl)prop-2-enamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 IPSKRGZEAGQLMG-QHHAFSJGSA-N 0.000 claims 1
- BKIGDKCEQIACOS-QHHAFSJGSA-N (e)-3-[2-bromo-4-(trifluoromethyl)phenyl]-n-(1h-indol-5-yl)prop-2-enamide Chemical compound BrC1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 BKIGDKCEQIACOS-QHHAFSJGSA-N 0.000 claims 1
- CMVMIBBVNLHAIL-QHHAFSJGSA-N (e)-3-[2-fluoro-4-(trifluoromethyl)phenyl]-n-(1h-indol-5-yl)prop-2-enamide Chemical compound FC1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 CMVMIBBVNLHAIL-QHHAFSJGSA-N 0.000 claims 1
- LXQIGTIFFFDGPE-CSKARUKUSA-N (e)-3-[2-pyridin-3-yl-4-(trifluoromethyl)phenyl]-n-quinolin-3-ylprop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3C=CC=CC3=NC=2)C=1C1=CC=CN=C1 LXQIGTIFFFDGPE-CSKARUKUSA-N 0.000 claims 1
- OOJGFXQKZZZSPW-UXBLZVDNSA-N (e)-n-(1,3-benzothiazol-6-yl)-3-(6-tert-butyl-2-methylpyridin-3-yl)prop-2-enamide Chemical compound CC1=NC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(N=CS2)C2=C1 OOJGFXQKZZZSPW-UXBLZVDNSA-N 0.000 claims 1
- QJISURBGYIEJII-QHHAFSJGSA-N (e)-n-(1,3-benzothiazol-6-yl)-3-[2-bromo-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound BrC1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(N=CS2)C2=C1 QJISURBGYIEJII-QHHAFSJGSA-N 0.000 claims 1
- DVBPLETXURFYAU-XVNBXDOJSA-N (e)-n-(1,3-benzothiazol-6-yl)-3-[2-methyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(N=CS2)C2=C1 DVBPLETXURFYAU-XVNBXDOJSA-N 0.000 claims 1
- DGOFLKXCPXBMSI-IZZDOVSWSA-N (e)-n-(1-benzofuran-5-yl)-3-(4-tert-butylphenyl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=C(OC=C2)C2=C1 DGOFLKXCPXBMSI-IZZDOVSWSA-N 0.000 claims 1
- QEVLOSCWBYWBHN-QHHAFSJGSA-N (e)-n-(1h-indol-5-yl)-3-[2-(1,3-thiazol-2-yl)-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3C=CNC3=CC=2)C=1C1=NC=CS1 QEVLOSCWBYWBHN-QHHAFSJGSA-N 0.000 claims 1
- WZAQUTXYUVPVIG-FPYGCLRLSA-N (e)-n-(1h-indol-5-yl)-3-[2-(6-methoxypyridin-3-yl)-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 WZAQUTXYUVPVIG-FPYGCLRLSA-N 0.000 claims 1
- CSEIAIYPMGIGIX-XBXARRHUSA-N (e)-n-(1h-indol-5-yl)-3-[2-(pyridin-3-ylmethyl)-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3C=CNC3=CC=2)C=1CC1=CC=CN=C1 CSEIAIYPMGIGIX-XBXARRHUSA-N 0.000 claims 1
- GNDSXDUVYDUOPT-XVNBXDOJSA-N (e)-n-(1h-indol-5-yl)-3-[2-methyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)NC1=CC=C(NC=C2)C2=C1 GNDSXDUVYDUOPT-XVNBXDOJSA-N 0.000 claims 1
- UFTUBLLKTPZPSI-XBXARRHUSA-N (e)-n-(1h-indol-5-yl)-3-[2-pyridin-3-yl-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3C=CNC3=CC=2)C=1C1=CC=CN=C1 UFTUBLLKTPZPSI-XBXARRHUSA-N 0.000 claims 1
- QDOOTOIUKPNYNZ-QHHAFSJGSA-N (e)-n-(1h-indol-5-yl)-3-[2-pyridin-4-yl-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3C=CNC3=CC=2)C=1C1=CC=NC=C1 QDOOTOIUKPNYNZ-QHHAFSJGSA-N 0.000 claims 1
- ZPRONJVVKGEVNX-VMPITWQZSA-N (e)-n-(1h-indol-6-yl)-3-[2-pyridin-3-yl-4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C(C(F)(F)F)=CC=C(\C=C\C(=O)NC=2C=C3NC=CC3=CC=2)C=1C1=CC=CN=C1 ZPRONJVVKGEVNX-VMPITWQZSA-N 0.000 claims 1
- YEGPXCDFEQAZBG-FMIVXFBMSA-N (e)-n-[3-(2-aminoethoxy)phenyl]-3-(4-tert-butylphenyl)prop-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC(OCCN)=C1 YEGPXCDFEQAZBG-FMIVXFBMSA-N 0.000 claims 1
- IWPXTELSEHLIJB-FPYGCLRLSA-N (e)-n-[3-(hydroxymethyl)-1,2,3,4-tetrahydroquinolin-7-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C=1C=C2CC(CO)CNC2=CC=1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1 IWPXTELSEHLIJB-FPYGCLRLSA-N 0.000 claims 1
- JONIAOGHAXHHQR-RUDMXATFSA-N (e)-n-[3-(hydroxymethyl)-1-methyl-3,4-dihydro-2h-quinolin-7-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C2N(C)CC(CO)CC2=CC=C1NC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1 JONIAOGHAXHHQR-RUDMXATFSA-N 0.000 claims 1
- MKVBVTOSWPBSNC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,4-triazine Chemical compound C1NNC=CN1 MKVBVTOSWPBSNC-UHFFFAOYSA-N 0.000 claims 1
- LVEKWSMAGKNFCF-UHFFFAOYSA-N 1,2,3,6-tetrahydro-1,2,4-triazine Chemical compound C1NNCN=C1 LVEKWSMAGKNFCF-UHFFFAOYSA-N 0.000 claims 1
- OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 claims 1
- JPIFWSVAGRPCBJ-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyridin-4-yl]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=NC(NC=2C=C3OCCOC3=CC=2)=C1 JPIFWSVAGRPCBJ-UHFFFAOYSA-N 0.000 claims 1
- OWUQTVMVNCGRLU-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyridin-4-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=NC(NC=2C=C3OCCOC3=CC=2)=C1 OWUQTVMVNCGRLU-UHFFFAOYSA-N 0.000 claims 1
- HGYGEJZLUZEDIH-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1,2,4-triazine Chemical compound C1NCC=NN1 HGYGEJZLUZEDIH-UHFFFAOYSA-N 0.000 claims 1
- UETXZUQLCCCICD-UHFFFAOYSA-N 2,3-dihydro-1,4,2-oxathiazine Chemical compound C1NOC=CS1 UETXZUQLCCCICD-UHFFFAOYSA-N 0.000 claims 1
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 claims 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims 1
- CJUYNKWJWWMLJW-UHFFFAOYSA-N 2,5-dihydrotriazine Chemical compound C1C=NNN=C1 CJUYNKWJWWMLJW-UHFFFAOYSA-N 0.000 claims 1
- PMBTWFPOEZPRBR-UHFFFAOYSA-N 2-(3-methoxyphenoxy)-4-[4-(trifluoromethyl)phenyl]pyridine Chemical compound COC1=CC=CC(OC=2N=CC=C(C=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 PMBTWFPOEZPRBR-UHFFFAOYSA-N 0.000 claims 1
- WQQLIHJGNGRVLL-FMIVXFBMSA-N 2-[3-[[(e)-3-(4-tert-butylphenyl)prop-2-enoyl]amino]phenoxy]acetic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1\C=C\C(=O)NC1=CC=CC(OCC(O)=O)=C1 WQQLIHJGNGRVLL-FMIVXFBMSA-N 0.000 claims 1
- SRCCLYMWDRNUAF-UHFFFAOYSA-N 3,3-dimethyl-1,2-dihydroindole Chemical compound C1=CC=C2C(C)(C)CNC2=C1 SRCCLYMWDRNUAF-UHFFFAOYSA-N 0.000 claims 1
- VGYDMOUMIQOMMU-UHFFFAOYSA-N 3,4-dihydro-2h-1,3-thiazine Chemical compound C1NCC=CS1 VGYDMOUMIQOMMU-UHFFFAOYSA-N 0.000 claims 1
- YEEGQDGJIXWFIQ-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-oxazine Chemical compound C1COC=CN1 YEEGQDGJIXWFIQ-UHFFFAOYSA-N 0.000 claims 1
- NARLFVSETWHKRP-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-thiazine Chemical compound C1CSC=CN1 NARLFVSETWHKRP-UHFFFAOYSA-N 0.000 claims 1
- UAGQYROKNUIGPX-UHFFFAOYSA-N 3,6-dihydro-2h-1,3-thiazine Chemical compound C1NC=CCS1 UAGQYROKNUIGPX-UHFFFAOYSA-N 0.000 claims 1
- RHOMRSNINFNDIY-UHFFFAOYSA-N 3,6-dihydro-2h-1,4-oxazine Chemical compound C1CN=CCO1 RHOMRSNINFNDIY-UHFFFAOYSA-N 0.000 claims 1
- QTAAKTRBARVAQY-UHFFFAOYSA-N 3,6-dihydro-2h-1,4-thiazine Chemical compound C1CN=CCS1 QTAAKTRBARVAQY-UHFFFAOYSA-N 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AQKLSQTZSACKKL-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridin-2-amine Chemical compound O1CCOC2=CC(NC=3N=CC=C(C=3)C3=CC=C4OCOC4=C3)=CC=C21 AQKLSQTZSACKKL-UHFFFAOYSA-N 0.000 claims 1
- CHYOROLLNYULMV-UHFFFAOYSA-N 4-(1-benzothiophen-2-yl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridin-2-amine Chemical compound C1=CC=C2SC(C=3C=C(N=CC=3)NC=3C=C4OCCOC4=CC=3)=CC2=C1 CHYOROLLNYULMV-UHFFFAOYSA-N 0.000 claims 1
- ZYFWREHXNQYUSE-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-n-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C=C(NC=3C=C4OCCOC4=CC=3)N=CC=2)=C1 ZYFWREHXNQYUSE-UHFFFAOYSA-N 0.000 claims 1
- UDFMGMGVXDBHKD-UHFFFAOYSA-N 4-[4-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxy-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1OC(N=CC=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 UDFMGMGVXDBHKD-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- IQOZTIKBIHWYQQ-UHFFFAOYSA-N 4h-1,3-oxazine Chemical compound C1C=COC=N1 IQOZTIKBIHWYQQ-UHFFFAOYSA-N 0.000 claims 1
- NXNZBSJCMSODTO-UHFFFAOYSA-N 5,6-dihydro-2h-1,3-thiazine Chemical compound C1CC=NCS1 NXNZBSJCMSODTO-UHFFFAOYSA-N 0.000 claims 1
- YPXAASDZAZBHMG-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-thiazine Chemical compound C1CSC=NC1 YPXAASDZAZBHMG-UHFFFAOYSA-N 0.000 claims 1
- BXIQUVIVBPUOSD-KPKJPENVSA-N 6-[[(e)-3-(4-tert-butylphenyl)prop-2-enoyl]amino]-n-methylindazole-1-carboxamide Chemical compound C1=C2N(C(=O)NC)N=CC2=CC=C1NC(=O)\C=C\C1=CC=C(C(C)(C)C)C=C1 BXIQUVIVBPUOSD-KPKJPENVSA-N 0.000 claims 1
- MQDXDIVLAQUUPE-UHFFFAOYSA-N 7-[4-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxyquinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=NC(OC=2C=C3N=CC=CC3=CC=2)=C1 MQDXDIVLAQUUPE-UHFFFAOYSA-N 0.000 claims 1
- PZLAMTDFMVQHND-UHFFFAOYSA-N 7-tert-butylisoquinoline-3-carboxamide Chemical compound C(C)(C)(C)C1=CC=C2C=C(N=CC2=C1)C(=O)N PZLAMTDFMVQHND-UHFFFAOYSA-N 0.000 claims 1
- RTFYMAQISLJCDS-UHFFFAOYSA-N 8-[4-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxyquinolin-2-amine Chemical compound C12=NC(N)=CC=C2C=CC=C1OC(N=CC=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 RTFYMAQISLJCDS-UHFFFAOYSA-N 0.000 claims 1
- FLIRHELTVBDESZ-UHFFFAOYSA-N 8-[4-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxyquinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=NC(OC=2C3=NC=CC=C3C=CC=2)=C1 FLIRHELTVBDESZ-UHFFFAOYSA-N 0.000 claims 1
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000005824 bladder abnormality Effects 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- MMUVGZYCOKRPAC-UHFFFAOYSA-N n-(1,3-benzothiazol-6-yl)-3-(4-tert-butylphenyl)-6-imidazol-1-ylhex-2-enamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(CCCN1C=NC=C1)=CC(=O)NC1=CC=C(N=CS2)C2=C1 MMUVGZYCOKRPAC-UHFFFAOYSA-N 0.000 claims 1
- MDZVRJRBFNCVCJ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(4-fluorophenyl)pyridin-2-amine Chemical compound C1=CC(F)=CC=C1C1=CC=NC(NC=2C=C3OCCOC3=CC=2)=C1 MDZVRJRBFNCVCJ-UHFFFAOYSA-N 0.000 claims 1
- VLKOFKUJZFJHME-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[3-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CC(C=2C=C(NC=3C=C4OCCOC4=CC=3)N=CC=2)=C1 VLKOFKUJZFJHME-UHFFFAOYSA-N 0.000 claims 1
- AJUSWXYINDCHCJ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[4-(dimethylamino)phenyl]pyridin-2-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=NC(NC=2C=C3OCCOC3=CC=2)=C1 AJUSWXYINDCHCJ-UHFFFAOYSA-N 0.000 claims 1
- WGYNXWGKWGRADX-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-[4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=NC(NC=2C=C3OCCOC3=CC=2)=C1 WGYNXWGKWGRADX-UHFFFAOYSA-N 0.000 claims 1
- SKLVOWLWWJOKFZ-UHFFFAOYSA-N n-[4-[4-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxy-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=CC=C2SC(NC(=O)C)=NC2=C1OC(N=CC=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 SKLVOWLWWJOKFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- NCOUFDATAZOQTF-WEVVVXLNSA-N tert-butyl 4-[2-[(e)-3-(1h-indol-5-ylamino)-3-oxoprop-1-enyl]-5-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine-6-carboxylate Chemical compound CC(C)(C)OC(=O)C1NCCC(C=2C(=CC=C(C=2)C(F)(F)F)\C=C\C(=O)NC=2C=C3C=CNC3=CC=2)=C1 NCOUFDATAZOQTF-WEVVVXLNSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 0 Cc1c(*)c(*)c(*)c(*)c1* Chemical compound Cc1c(*)c(*)c(*)c(*)c1* 0.000 description 11
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33916101P | 2001-12-10 | 2001-12-10 | |
| US34473701P | 2001-12-21 | 2001-12-21 | |
| US38333102P | 2002-05-22 | 2002-05-22 | |
| US40242202P | 2002-08-08 | 2002-08-08 | |
| PCT/US2002/039589 WO2003049702A2 (en) | 2001-12-10 | 2002-12-10 | Vanilloid receptor ligands and their use in treatments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005518371A JP2005518371A (ja) | 2005-06-23 |
| JP2005518371A5 true JP2005518371A5 (https=) | 2006-02-02 |
Family
ID=27502596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003550753A Pending JP2005518371A (ja) | 2001-12-10 | 2002-12-10 | バニロイド受容体リガンド及び治療に於けるこれらの使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US7582657B2 (https=) |
| EP (1) | EP1463714A4 (https=) |
| JP (1) | JP2005518371A (https=) |
| AU (1) | AU2002364549B2 (https=) |
| CA (1) | CA2468544A1 (https=) |
| MX (1) | MXPA04005427A (https=) |
| PL (1) | PL373484A1 (https=) |
| WO (1) | WO2003049702A2 (https=) |
Families Citing this family (132)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2476936A1 (en) * | 2002-02-20 | 2003-08-28 | Chih-Hung Lee | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (vr1) receptor |
| WO2003097586A1 (en) | 2002-05-17 | 2003-11-27 | Janssen Pharmaceutica N.V. | Aminotetralin-derived urea modulators of vanilloid vr1 receptor |
| EP1688408A3 (en) * | 2002-08-08 | 2007-08-22 | Amgen, Inc | Vanilloid receptor ligands and their use in treatments |
| AR041191A1 (es) | 2002-08-08 | 2005-05-04 | Amgen Inc | Ligandos del receptor vanilloide y su uso en tratamientos |
| US7482488B2 (en) * | 2002-08-29 | 2009-01-27 | Temple University - Of The Commonwealth System Of Higher Education | Aryl and heteroaryl propene amides, derivatives thereof and therapeutic uses thereof |
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| AU2003278600A1 (en) * | 2002-11-01 | 2004-05-25 | Takeda Pharmaceutical Company Limited | Agent for preventing or treating neuropathy |
| EP1569925A1 (en) * | 2002-12-13 | 2005-09-07 | Neurogen Corporation | 2-substituted quinazolin-4-ylamine analogues as capsaicin receptor modulators |
| AU2002953533A0 (en) | 2002-12-24 | 2003-01-16 | Arthron Limited | Fc receptor modulating compounds and compositions |
| US20040192728A1 (en) * | 2003-02-03 | 2004-09-30 | Ellen Codd | Quinoline-derived amide modulators of vanilloid VR1 receptor |
| SE0301446D0 (sv) | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | New Compounds |
| WO2005007646A1 (en) * | 2003-07-10 | 2005-01-27 | Neurogen Corporation | Substituted heterocyclic diarylamine analogues |
| CA2531490A1 (en) * | 2003-07-15 | 2005-02-03 | Neurogen Corporation | Substituted pyrimidin-4-ylamina analogues as vanilloid receptor ligands |
| CA2531619A1 (en) * | 2003-07-16 | 2005-01-27 | Neurogen Corporation | Biaryl piperazinyl-pyridine analogues |
| EP1670794A2 (en) | 2003-09-30 | 2006-06-21 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP1775295A1 (en) * | 2003-09-30 | 2007-04-18 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| WO2005040100A1 (en) * | 2003-10-15 | 2005-05-06 | Bayer Healthcare Ag | Tetrahydro-naphthalene and urea derivatives |
| DE10360745A1 (de) * | 2003-12-23 | 2005-07-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| US7553848B2 (en) | 2004-01-23 | 2009-06-30 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| AU2005212438A1 (en) | 2004-02-11 | 2005-08-25 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| MY139645A (en) * | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| US7351739B2 (en) * | 2004-04-30 | 2008-04-01 | Wellgen, Inc. | Bioactive compounds and methods of uses thereof |
| RU2361872C2 (ru) * | 2004-05-26 | 2009-07-20 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Циннамидное соединение |
| US8354427B2 (en) * | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| LT2502911T (lt) | 2004-06-24 | 2017-09-11 | Vertex Pharmaceuticals Incorporated | Atp surišančios kasetės transporterių moduliatoriai |
| WO2006006740A1 (ja) * | 2004-07-14 | 2006-01-19 | Japan Tobacco Inc. | ３−アミノベンズアミド化合物及びバニロイド受容体１型(ｖｒ１)活性阻害剤 |
| MX2007000480A (es) | 2004-07-15 | 2007-03-29 | Japan Tobacco Inc | Compuesto de benzamida fusionado e inhibidor de actividad de receptor de vainilloide 1. |
| FR2874015B1 (fr) | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| DE602005019602D1 (de) * | 2004-10-26 | 2010-04-08 | Eisai R&D Man Co Ltd | Amorphe form einer zimtsäureamidverbindung |
| DE602005009021D1 (de) * | 2004-12-17 | 2008-09-25 | Lilly Co Eli | Neue mch-rezeptorantagonisten |
| US7301022B2 (en) | 2005-02-15 | 2007-11-27 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| CA2601871A1 (en) | 2005-03-19 | 2006-09-28 | Amorepacific Corporation | Novel compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and pharmaceutical compositions containing the same |
| WO2006102645A1 (en) * | 2005-03-24 | 2006-09-28 | Janssen Pharmaceutica, N.V. | Biaryl derived amide modulators of vanilloid vr1 receptor |
| RU2451014C2 (ru) * | 2005-07-22 | 2012-05-20 | Мотида Фармасьютикал Ко., Лтд. | Новое производное гетероциклиден ацетамида |
| NZ565080A (en) | 2005-07-22 | 2011-03-31 | Mochida Pharm Co Ltd | Novel heterocyclidene acetamide derivative |
| JP2009514876A (ja) * | 2005-11-03 | 2009-04-09 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼのための化合物および組成物 |
| CN101309916A (zh) * | 2005-11-18 | 2008-11-19 | 卫材R&D管理有限公司 | 制备肉桂酰胺衍生物的方法 |
| US20090048448A1 (en) * | 2005-11-18 | 2009-02-19 | Ikuo Kushida | Salts of cynnamide compound or solvates thereof |
| KR20080069221A (ko) * | 2005-11-24 | 2008-07-25 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 모르폴린 타입의 신나미드 화합물 |
| TWI370130B (en) | 2005-11-24 | 2012-08-11 | Eisai R&D Man Co Ltd | Two cyclic cinnamide compound |
| US7709501B2 (en) * | 2005-12-23 | 2010-05-04 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| TW200736227A (en) | 2005-12-23 | 2007-10-01 | Astrazeneca Ab | New compounds III |
| CA2634113A1 (en) * | 2005-12-24 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Quinolin- 4 - one derivatives as modulators of abc transporters |
| EP1967519B1 (en) * | 2005-12-28 | 2012-09-05 | Japan Tobacco Inc. | 3,4-dihydrobenzoxazine compound and inhibitor of vanilloid receptor type 1 (vr1) activity |
| WO2007079139A2 (en) | 2005-12-28 | 2007-07-12 | Vertex Pharmaceuticals, Inc. | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US7906508B2 (en) * | 2005-12-28 | 2011-03-15 | Japan Tobacco Inc. | 3,4-dihydrobenzoxazine compounds and inhibitors of vanilloid receptor subtype 1 (VRI) activity |
| TWI378091B (en) * | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| KR20090016591A (ko) * | 2006-05-19 | 2009-02-16 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 헤테로사이클 타입의 신나미드 유도체 |
| MX352516B (es) | 2006-07-05 | 2017-04-06 | Fibrotech Therapeutics Pty Ltd | Compuestos terapeuticos. |
| EP1889837A1 (en) * | 2006-07-10 | 2008-02-20 | Pharmeste S.r.l. | VR1 vanilloid receptor antagonists with a iononic substructure |
| EP1889830A1 (en) | 2006-07-10 | 2008-02-20 | Pharmeste S.r.l. | Biarylcarboxyarylamides as vanilloid-1 receptor modulators |
| WO2008007780A1 (fr) | 2006-07-13 | 2008-01-17 | Kyowa Hakko Kirin Co., Ltd. | Dérivé du pentadiènamide |
| AU2007277519B2 (en) | 2006-07-27 | 2011-12-22 | Amorepacific Corporation | Novel compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and pharmaceutical compositions containing the same |
| US7737141B2 (en) | 2006-07-28 | 2010-06-15 | Eisai R&D Management Co., Ltd. | Prodrug of cinnamide compound |
| US8034940B2 (en) | 2006-08-09 | 2011-10-11 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
| CA2661898A1 (en) | 2006-08-25 | 2008-02-28 | Abbott Laboratories | Indazole derivatives that inhibit trpv1 and uses thereof |
| US20080095720A1 (en) * | 2006-10-18 | 2008-04-24 | Conopco, Inc., D/B/A Unilever | Skin Benefit Compositions with a Vanilloid Receptor Antagonist |
| EP1939181A1 (en) * | 2006-12-27 | 2008-07-02 | sanofi-aventis | Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase |
| FR2911604B1 (fr) | 2007-01-19 | 2009-04-17 | Sanofi Aventis Sa | Derives de n-(heteroaryl-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| FR2911605B1 (fr) | 2007-01-19 | 2009-04-17 | Sanofi Aventis Sa | Derives de pyrrolopyridine-2-carbowamides, leur preparation et leur application en therapeutique |
| PE20081692A1 (es) * | 2007-01-24 | 2008-12-18 | Mochida Pharm Co Ltd | Nuevo derivado de heterocicliden acetamida |
| CL2008000582A1 (es) * | 2007-02-28 | 2008-06-27 | Eisai R&D Man Co Ltd | Compuestos ciclicos derivados de oximorfolina condensados; farmacos que comprenden a dichos compuestos; y su uso para tratar enfermedad de alzheimer, demencia senil, sindrome de down o amiloidosis. |
| ITFI20070097A1 (it) * | 2007-04-20 | 2008-10-21 | Antonio Guarna | Molecole eterocicliche contenenti il nucleo della morfolina loro preparazione ed uso. |
| US20080306272A1 (en) * | 2007-05-16 | 2008-12-11 | Eisai R&D Management Co., Ltd. | One-pot methods for preparing cinnamide derivatives |
| WO2009001374A2 (en) * | 2007-06-25 | 2008-12-31 | Aptuit Laurus Pvt Ltd | Preparation of ethyl-3'-[((7-chloro-2-quinolinyl)ethenyl)phenyl]-3-oxopropanoate, a key intermediate for montelukast sodium |
| WO2009023160A2 (en) * | 2007-08-11 | 2009-02-19 | The Uab Research Foundation | Novel inhibitors of bacterial sortase enzymes and methods of using the same |
| US7935815B2 (en) * | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| BRPI0815773A2 (pt) | 2007-08-31 | 2019-09-24 | Eisai R&D Man Co Ltd | composto, e, medicamento. |
| CA2709937C (en) | 2007-12-21 | 2016-03-22 | Fibrotech Therapeutics Pty Ltd | Halogenated analogues of anti-fibrotic agents |
| US8608632B1 (en) | 2009-07-03 | 2013-12-17 | Salutaris Medical Devices, Inc. | Methods and devices for minimally-invasive extraocular delivery of radiation and/or pharmaceutics to the posterior portion of the eye |
| US8602959B1 (en) | 2010-05-21 | 2013-12-10 | Robert Park | Methods and devices for delivery of radiation to the posterior portion of the eye |
| US9056201B1 (en) | 2008-01-07 | 2015-06-16 | Salutaris Medical Devices, Inc. | Methods and devices for minimally-invasive delivery of radiation to the eye |
| DK2227257T3 (da) | 2008-01-07 | 2013-09-30 | Salutaris Medical Devices Inc | Anordninger til minimal-invasiv ekstraokular afgivelse af stråling til den posteriore del af øjet |
| US10022558B1 (en) | 2008-01-07 | 2018-07-17 | Salutaris Medical Devices, Inc. | Methods and devices for minimally-invasive delivery of radiation to the eye |
| US9873001B2 (en) | 2008-01-07 | 2018-01-23 | Salutaris Medical Devices, Inc. | Methods and devices for minimally-invasive delivery of radiation to the eye |
| WO2009096349A1 (ja) * | 2008-01-28 | 2009-08-06 | Eisai R & D Management Co., Ltd. | 結晶性のシンナミド化合物またはその塩 |
| WO2009096701A2 (en) | 2008-01-28 | 2009-08-06 | Amorepacific Corporation | Novel compounds, isomer thereof, or pharmaceutically acceptable salts thereof as vanilloid receptor antagonist; and pharmaceutical compositions containing the same |
| US11969501B2 (en) | 2008-04-21 | 2024-04-30 | Dompé Farmaceutici S.P.A. | Auris formulations for treating otic diseases and conditions |
| EP2278999B1 (en) | 2008-04-21 | 2025-01-29 | Dompé farmaceutici S.p.A. | Auris formulations for treating otic diseases and conditions |
| JP5438103B2 (ja) | 2008-07-02 | 2014-03-12 | アモーレパシフィック コーポレイション | バニロイド受容体アンタゴニストとしての新規化合物、その異性体またはその薬学的に許容される塩、並びにそれを含む医薬組成物 |
| EP2306975A4 (en) | 2008-07-21 | 2012-10-31 | Otonomy Inc | COMPOSITIONS WITH A TAXED RELEASE FOR MODULATING THE EARM STRUCTURE AND THE BORN IMMUNE SYSTEM, AND METHODS OF TREATING EAR OR DISEASE |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| NZ592685A (en) | 2008-10-23 | 2013-04-26 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| EP2179984A1 (en) | 2008-10-27 | 2010-04-28 | Congenia S.r.l. | Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition |
| USD691267S1 (en) | 2009-01-07 | 2013-10-08 | Salutaris Medical Devices, Inc. | Fixed-shape cannula for posterior delivery of radiation to eye |
| USD691270S1 (en) | 2009-01-07 | 2013-10-08 | Salutaris Medical Devices, Inc. | Fixed-shape cannula for posterior delivery of radiation to an eye |
| USD691268S1 (en) | 2009-01-07 | 2013-10-08 | Salutaris Medical Devices, Inc. | Fixed-shape cannula for posterior delivery of radiation to eye |
| USD691269S1 (en) | 2009-01-07 | 2013-10-08 | Salutaris Medical Devices, Inc. | Fixed-shape cannula for posterior delivery of radiation to an eye |
| US20110287931A1 (en) * | 2009-02-03 | 2011-11-24 | Nippon Soda Co., Ltd. | Rewritable recording material |
| WO2010089984A1 (ja) * | 2009-02-03 | 2010-08-12 | 日本曹達株式会社 | フェノール性化合物および記録材料 |
| SI2408750T1 (sl) | 2009-03-20 | 2015-11-30 | Vertex Pharmaceuticals Incorporated | Postopek za izdelavo modulatorjev cistično-fibroznega transmembranskega regulatorja prevodnosti |
| CN102574843B (zh) | 2009-10-22 | 2015-06-17 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
| EP2496304A4 (en) * | 2009-11-02 | 2013-04-17 | Salutaris Medical Devices Inc | METHOD AND DEVICES FOR THE ADMINISTRATION OF MINIMALLY INVASIVE EXTRACOLAR RADIATION |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MY165659A (en) * | 2010-09-28 | 2018-04-18 | Dae Woong Pharma | Novel method of preparing benzoimidazole derivatives |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| EP2819670A1 (en) | 2012-02-27 | 2015-01-07 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administration thereof |
| US20150225369A1 (en) * | 2012-08-29 | 2015-08-13 | Merck Patent Gmbh | Ddr2 inhibitors for the treatment of osteoarthritis |
| KR20150100923A (ko) | 2012-12-28 | 2015-09-02 | 니폰 조키 세야쿠 가부시키가이샤 | 신남산 아미드 유도체 |
| FR3006192A1 (fr) * | 2013-05-30 | 2014-12-05 | Centre Nat Rech Scient | Composes de type phenyle propenamide pour leur utilisation en tant que medicament |
| BR112015030326A2 (pt) | 2013-06-05 | 2017-08-29 | Synergy Pharmaceuticals Inc | Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos |
| KR20170063954A (ko) | 2014-10-07 | 2017-06-08 | 버텍스 파마슈티칼스 인코포레이티드 | 낭성 섬유증 막횡단 전도도 조절자의 조정제의 공-결정 |
| US10723708B2 (en) | 2014-11-10 | 2020-07-28 | Evrys Bio, Llc | Anti-HCMV compositions and methods |
| AU2016250265A1 (en) * | 2015-04-15 | 2017-10-12 | Valent Biosciences Llc | (S)-2'-vinyl-abscisic acid derivatives |
| KR102439852B1 (ko) * | 2015-04-17 | 2022-09-05 | 가천대학교 산학협력단 | 2-아미노퀴놀린-8-올 유도체, 및 이의 용도 |
| KR101806485B1 (ko) | 2015-09-04 | 2017-12-08 | 서울대학교산학협력단 | 파이퍼 아마이드 유도체를 포함하는 피부 미백용 조성물 |
| CN105130964A (zh) * | 2015-09-28 | 2015-12-09 | 侯方杰 | 一种可用于制备治疗心血管疾病药物的化合物及其制备方法、用途 |
| CN105085492A (zh) * | 2015-09-29 | 2015-11-25 | 青岛友诚高新技术有限公司 | 一种可用于制备治疗冠状动脉粥样硬化药物的化合物及其制备方法、用途 |
| CN105153125A (zh) * | 2015-09-29 | 2015-12-16 | 青岛友诚高新技术有限公司 | 一种可用于制备保护心肌缺血药物的化合物及其制备方法、用途 |
| CN105130965A (zh) * | 2015-10-08 | 2015-12-09 | 侯方杰 | 一种可用于制备治疗心血管疾病药物的化合物及其制备方法、用途 |
| CN105461700A (zh) * | 2015-12-02 | 2016-04-06 | 青岛市中心医院 | 一种可用于制备抗乳腺癌药物的化合物及其制备方法、用途 |
| WO2017102014A1 (en) * | 2015-12-17 | 2017-06-22 | Universite D'aix-Marseille | Propenamide thiophene derivatives as flavivirus inhibitors and their use |
| USD815285S1 (en) | 2016-05-11 | 2018-04-10 | Salutaris Medical Devices, Inc. | Brachytherapy device |
| USD814637S1 (en) | 2016-05-11 | 2018-04-03 | Salutaris Medical Devices, Inc. | Brachytherapy device |
| USD814638S1 (en) | 2016-05-11 | 2018-04-03 | Salutaris Medical Devices, Inc. | Brachytherapy device |
| AU2017290256A1 (en) | 2016-06-29 | 2019-01-17 | Otonomy, Inc. | Triglyceride otic formulations and uses thereof |
| USD808529S1 (en) | 2016-08-31 | 2018-01-23 | Salutaris Medical Devices, Inc. | Holder for a brachytherapy device |
| USD808528S1 (en) | 2016-08-31 | 2018-01-23 | Salutaris Medical Devices, Inc. | Holder for a brachytherapy device |
| KR101983788B1 (ko) * | 2016-12-01 | 2019-05-30 | 서울대학교산학협력단 | 아미드 유도체 화합물, 이의 입체이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 포함하는 피부 노화 억제, 주름 개선, 또는 피부 상처 치료용 약학적 또는 화장료 조성물 |
| JP2020502136A (ja) * | 2016-12-14 | 2020-01-23 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｎｒｆ２レギュレーターとしてのビスアリールアミド |
| JP7185631B2 (ja) | 2017-02-03 | 2022-12-07 | サータ セラピューティクス プロプライエタリー リミテッド | 抗線維化化合物 |
| WO2019084338A1 (en) * | 2017-10-25 | 2019-05-02 | University Of South Florida | DRUG-INDUCED ACTIVATION OF THE REELIN SIGNALING SYSTEM |
| KR102334947B1 (ko) * | 2020-04-22 | 2021-12-06 | 주식회사 제이맥켐 | Trpv1 길항제로서 벤즈이미다졸론계 시남아마이드 유도체 및 이를 유효성분으로 함유하는 통증의 치료 또는 예방용 약학적 조성물 |
| CN113549018B (zh) * | 2020-04-24 | 2024-02-27 | 中国药科大学 | 蛋白激酶抑制剂及其衍生物，制备方法、药物组合物和应用 |
| DE102022104759A1 (de) | 2022-02-28 | 2023-08-31 | SCi Kontor GmbH | Co-Kristall-Screening Verfahren, insbesondere zur Herstellung von Co-Kristallen |
| WO2024206284A2 (en) * | 2023-03-27 | 2024-10-03 | Rutgers, The State University Of New Jersey | Therapeutic compounds |
| CN120398870A (zh) * | 2024-01-31 | 2025-08-01 | 深圳晶蛋生物医药科技有限公司 | 一种苯并吗啉类化合物及其应用 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US87922A (en) * | 1869-03-16 | Improvement in gas-burners | ||
| US456346A (en) * | 1891-07-21 | Henry e | ||
| US4011236A (en) * | 1968-09-09 | 1977-03-08 | Merck & Co., Inc. | N-(benzimidazol-2-yl)arylcarboxamides as ultraviolet (uv) light absorbers |
| US3853561A (en) * | 1970-11-26 | 1974-12-10 | Hoechst Ag | Process for the preparation of screen printing stencils using intermediate support for light sensitive layer |
| JPS5640710B2 (https=) * | 1973-01-18 | 1981-09-22 | ||
| FR2230764B1 (https=) * | 1973-05-21 | 1977-02-11 | Verdol Sa | |
| CS244440B2 (en) * | 1983-02-28 | 1986-07-17 | Celamerck Gmbh & Co Kg | Method of acrylic acids' new amides production |
| US4536346A (en) * | 1983-05-06 | 1985-08-20 | American Cyanamid Company | Aralkanamidophenyl compounds |
| FR2559763B1 (fr) | 1984-02-22 | 1986-07-11 | Centre Nat Rech Scient | Composes possedant, notamment, des proprietes inhibitrices vis-a-vis de la lignification dans les vegetaux et procede pour la reduction de leur taux de lignine |
| JPH064584B2 (ja) * | 1984-02-29 | 1994-01-19 | 沢井製薬株式会社 | 新規アニリド誘導体 |
| CA1261835A (en) * | 1984-08-20 | 1989-09-26 | Masaaki Toda | (fused) benz(thio)amides |
| JPH0723349B2 (ja) * | 1986-12-17 | 1995-03-15 | 鐘淵化学工業株式会社 | ３，５−ジ−タ−シヤリ−ブチル−４−ヒドロキシケイ皮酸アミド誘導体 |
| US4927838A (en) * | 1987-07-10 | 1990-05-22 | Hoffman-La Roche Inc. | Pyridine compounds which are useful in treating a disease state characterized by an excess of platelet activating factors |
| DE3803775A1 (de) * | 1988-02-09 | 1989-08-17 | Boehringer Mannheim Gmbh | Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| US4908381A (en) * | 1988-12-05 | 1990-03-13 | Ecolab Inc. | Antimicrobial film-forming compositions |
| US5143919A (en) | 1990-08-17 | 1992-09-01 | Takeda Chemical Industries, Ltd. | Thienopyridine derivatives and their pharmaceutical use |
| ATE148098T1 (de) * | 1991-02-21 | 1997-02-15 | Sankyo Co | Benzolderivate zum fördern der produktion des nervenwachstumsfaktors |
| GB9208492D0 (en) * | 1992-04-16 | 1992-06-03 | Glaxo Spa | Heterocyclic compounds |
| US5453421A (en) * | 1992-09-11 | 1995-09-26 | E. R. Squibb & Sons, Inc. | Aryl and heterocyclic substituted propenamide derivatives |
| JPH06179660A (ja) | 1992-10-14 | 1994-06-28 | Nippon Soda Co Ltd | ジシアノピラジン誘導体 |
| US5731324A (en) | 1993-07-22 | 1998-03-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| GB9319243D0 (en) | 1993-09-17 | 1993-11-03 | Glaxo Spa | Heterocyclic compounds |
| GB9504361D0 (en) * | 1995-03-04 | 1995-04-26 | Glaxo Spa | Heterocyclic compounds |
| IL118469A (en) * | 1995-06-15 | 2000-08-13 | Tanabe Seiyaku Co | Naphthalene derivatives their preparation and intermediates thereof |
| US5780487A (en) * | 1995-08-07 | 1998-07-14 | Amer Moh Samir | S-2'- 2-(1-methyl-2-piperidyl) ethyl! cinnamanilide |
| US5731342A (en) * | 1996-02-22 | 1998-03-24 | Eli Lilly And Company | Benzothiophenes, formulations containing same, and methods |
| WO1997043241A1 (en) | 1996-05-13 | 1997-11-20 | Nippon Shinyaku Co., Ltd. | Substituted ethylene compounds and drugs |
| US5776930A (en) * | 1996-06-28 | 1998-07-07 | Merck & Company, Inc. | Pharmaceutical preparation |
| US5919776A (en) * | 1996-12-20 | 1999-07-06 | Merck & Co., Inc. | Substituted aminoquinolines as modulators of chemokine receptor activity |
| CA2320167A1 (en) * | 1998-03-19 | 1999-09-23 | Steven R. Turner | 1,3,4-thiadiazoles useful for the treatment of cmv infections |
| CA2338804A1 (en) | 1998-07-28 | 2000-02-10 | Smithkline Beecham Corporation | Propenamides as ccr5 modulators |
| GB9816984D0 (en) | 1998-08-05 | 1998-09-30 | Smithkline Beecham Plc | Novel compounds |
| CA2348267A1 (en) * | 1998-10-29 | 2000-05-11 | Henry H. Gu | Novel inhibitors of impdh enzyme |
| DE19935219A1 (de) * | 1999-07-27 | 2001-02-01 | Boehringer Ingelheim Pharma | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| BR0013551A (pt) * | 1999-08-13 | 2003-06-17 | Vertex Pharma | Inibidores de cinases n-terminal cjun (jnk) e outras cinases de proteìnas |
| EP1218336A2 (en) | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| JP2003527395A (ja) | 2000-03-17 | 2003-09-16 | ノボ ノルディスク アクティーゼルスカブ | ヒスタミンｈ３受容体リガンドとしての縮環イミダゾール |
| GB0014022D0 (en) * | 2000-06-08 | 2000-08-02 | Novartis Ag | Organic compounds |
| CA2415899A1 (en) * | 2000-07-18 | 2003-01-13 | Chikashi Saitoh | Medicine comprising dicyanopyridine derivative |
| CA2441733A1 (en) | 2001-03-29 | 2002-10-10 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| CA2468159A1 (en) * | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| GB0226724D0 (en) | 2002-11-15 | 2002-12-24 | Merck Sharp & Dohme | Therapeutic agents |
-
2002
- 2002-12-10 JP JP2003550753A patent/JP2005518371A/ja active Pending
- 2002-12-10 EP EP02799927A patent/EP1463714A4/en not_active Withdrawn
- 2002-12-10 WO PCT/US2002/039589 patent/WO2003049702A2/en not_active Ceased
- 2002-12-10 CA CA002468544A patent/CA2468544A1/en not_active Abandoned
- 2002-12-10 AU AU2002364549A patent/AU2002364549B2/en not_active Ceased
- 2002-12-10 MX MXPA04005427A patent/MXPA04005427A/es active IP Right Grant
- 2002-12-10 PL PL02373484A patent/PL373484A1/xx unknown
- 2002-12-10 US US10/316,295 patent/US7582657B2/en not_active Expired - Fee Related
-
2005
- 2005-04-05 US US11/100,272 patent/US20060030618A1/en not_active Abandoned
- 2005-04-05 US US11/099,978 patent/US20050272931A1/en not_active Abandoned
- 2005-04-05 US US11/100,077 patent/US7579347B2/en not_active Expired - Fee Related
-
2009
- 2009-06-26 US US12/492,376 patent/US20090264424A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005518371A5 (https=) | ||
| JP2005531574A5 (https=) | ||
| JP2005518371A (ja) | バニロイド受容体リガンド及び治療に於けるこれらの使用 | |
| CA2493667A1 (en) | Vanilloid receptor ligands and their use in treatments | |
| WO2003099284B1 (en) | Amino-pyridine, -pyridine and pyridazine derivatives for use as vanilloid receptor ligands for the treatment of pain | |
| TWI404715B (zh) | 二芳基醚脲化合物 | |
| JP2007533635A (ja) | バニロイド受容体リガンドおよび治療おけるこれらの使用 | |
| JP4216196B2 (ja) | Ｎｐｙアンタゴニストとしてのキノリン誘導体 | |
| JP2006519264A (ja) | 癌および他の障害の処置に有用な新規シアノピリジン誘導体 | |
| HUP0401898A2 (hu) | 3-Szubsztituált-4-pirimidon-származékok, ezeket tartalmazó gyógyászati készítmények és intermedierjeik | |
| CZ2003765A3 (cs) | Deriváty chinazolinu jako inhibitory kinázy | |
| BG63487B1 (bg) | Използване на хетероциклени съединения | |
| CN103429583A (zh) | 作为wnt信号通路抑制剂的三唑衍生物 | |
| HU191092B (en) | Process for producing 1,4-dihydro-pyridine derivatives | |
| JPH09511759A (ja) | アポリポタンパク質−ｂ合成阻害剤 | |
| BRPI0709101A2 (pt) | derivados de triazolona e medicamento e agente terapêutico e/ou profilático compreendendo os mesmos | |
| JP5372138B2 (ja) | 新規ベンゾオキサジンベンズイミダゾール誘導体、これを含む薬学組成物およびこの用途 | |
| WO2012174856A1 (zh) | 一类可用于口服的凝血酶抑制剂及其制法以及医药用途 | |
| JPH05194441A (ja) | 新規な置換３−ピペラジニルアルキル−２，３−ジヒドロ−４ｈ−１，３−ベンゾオキサジン−４−オン、その製造法および治療用途 | |
| JP4662979B2 (ja) | 新規なβ−アゴニスト、その製造方法及びその薬物としての使用 | |
| WO2010111948A1 (zh) | 芳甲胺类化合物、其制备方法及其医药用途 | |
| JPS6344576A (ja) | 新規ピリダジノン誘導体、それらの製造方法並びに医薬としてのそれらの利用法 | |
| AU2009221294A1 (en) | 2-Aminoquinolines | |
| WO2010141550A2 (en) | 11-beta hsd1 inhibitors | |
| JP2007537225A (ja) | ５−ｈｔ７活性剤としてのアルキルオキシインドールのピリジン誘導体 |