JP2007505085A5 - - Google Patents
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- Publication number
- JP2007505085A5 JP2007505085A5 JP2006525833A JP2006525833A JP2007505085A5 JP 2007505085 A5 JP2007505085 A5 JP 2007505085A5 JP 2006525833 A JP2006525833 A JP 2006525833A JP 2006525833 A JP2006525833 A JP 2006525833A JP 2007505085 A5 JP2007505085 A5 JP 2007505085A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- benzimidazol
- ylidene
- dihydro
- acetonitrile
- 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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- -1 amino, carboxy, aminocarbonyl Chemical group 0.000 claims 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- GVAAUBDAYOGTMQ-UHFFFAOYSA-N acetonitrile;1H-benzimidazole Chemical compound CC#N.C1=CC=C2NC=NC2=C1 GVAAUBDAYOGTMQ-UHFFFAOYSA-N 0.000 claims 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- NYCVCXMSZNOGDH-UHFFFAOYSA-M pyrrolidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-M 0.000 claims 4
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 206010012601 Diabetes mellitus Diseases 0.000 claims 2
- 206010022489 Insulin resistance Diseases 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 230000000240 adjuvant Effects 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 2
- 229950010170 epalrestat Drugs 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- WMASQBHSXPTQIJ-ZAFFBPSHSA-N (1R,5R,7R)-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxamide Chemical compound N\1C2=CC=CC=C2N(CC)C/1=C(\C#N)C1=NC(NC(=O)[C@H]2[C@@]3([H])CNC[C@](O3)(O2)[H])=NC=C1C WMASQBHSXPTQIJ-ZAFFBPSHSA-N 0.000 claims 1
- WMASQBHSXPTQIJ-LVDSTPADSA-N (1S,5S,7S)-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-carboxamide Chemical compound N\1C2=CC=CC=C2N(CC)C/1=C(\C#N)C1=NC(NC(=O)[C@@H]2[C@]3([H])CNC[C@@](O3)(O2)[H])=NC=C1C WMASQBHSXPTQIJ-LVDSTPADSA-N 0.000 claims 1
- SEAQTHCVAGBRFY-INWYIAFRSA-N (2R,4S)-6-fluoro-2-methylspiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C([C@H](OC1=CC=C(F)C=C11)C)[C@@]21NC(=O)NC2=O SEAQTHCVAGBRFY-INWYIAFRSA-N 0.000 claims 1
- XUFXOAAUWZOOIT-WVJZLWNXSA-N (2S,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-WVJZLWNXSA-N 0.000 claims 1
- WAAPEIZFCHNLKK-UFBFGSQYSA-N (2S,4S)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 claims 1
- DDVNZPBCWLCHHP-CAPFRKAQSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-(2-imidazol-1-ylethylamino)-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCN1C=CN=C1 DDVNZPBCWLCHHP-CAPFRKAQSA-N 0.000 claims 1
- JFPZAMGLUXPGJQ-CAPFRKAQSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-(3-pyrazol-1-ylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCCN1C=CC=N1 JFPZAMGLUXPGJQ-CAPFRKAQSA-N 0.000 claims 1
- YQZPLFKEVGBUBM-CAPFRKAQSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-[2-(1H-imidazol-5-yl)ethylamino]-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCC1=CNC=N1 YQZPLFKEVGBUBM-CAPFRKAQSA-N 0.000 claims 1
- LZYUNMYBEZQFTD-XDJHFCHBSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-[2-(1H-imidazol-5-yl)ethylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCC1=CNC=N1 LZYUNMYBEZQFTD-XDJHFCHBSA-N 0.000 claims 1
- AMPNWCYXHULHKW-LKUDQCMESA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-[2-(1H-indol-3-yl)ethylamino]-5-methylpyrimidin-4-yl]acetonitrile Chemical compound C1=CC=C2C(CCNC=3N=C(C(=CN=3)C)C(/C#N)=C3/N(C4=CC=CC=C4N3)CC)=CNC2=C1 AMPNWCYXHULHKW-LKUDQCMESA-N 0.000 claims 1
- ZDACKGNFEATCSO-XDJHFCHBSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[2-[3-(1,2,4-triazol-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NCCCN1C=NC=N1 ZDACKGNFEATCSO-XDJHFCHBSA-N 0.000 claims 1
- XRWHEPGKBFENFV-XDJHFCHBSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-(2-methylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C1=NC(NCC(C)C)=NC=C1C XRWHEPGKBFENFV-XDJHFCHBSA-N 0.000 claims 1
- AURMLXSMQYFGKW-RELWKKBWSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-(2-piperidin-1-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCN1CCCCC1 AURMLXSMQYFGKW-RELWKKBWSA-N 0.000 claims 1
- PTZQHCCTCVQRJR-HEHNFIMWSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-(3-pyrazol-1-ylpropylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1C=CC=N1 PTZQHCCTCVQRJR-HEHNFIMWSA-N 0.000 claims 1
- LFWFNXNKIKCCOT-CAPFRKAQSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-(piperidin-4-ylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCNCC1 LFWFNXNKIKCCOT-CAPFRKAQSA-N 0.000 claims 1
- RHSQSWWCNGUHFC-HEHNFIMWSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-[(1-methylpiperidin-4-yl)amino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCN(C)CC1 RHSQSWWCNGUHFC-HEHNFIMWSA-N 0.000 claims 1
- RBNRLRZYGUTKBO-CAPFRKAQSA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-[3-(1,2,4-triazol-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1C=NC=N1 RBNRLRZYGUTKBO-CAPFRKAQSA-N 0.000 claims 1
- VCIMMQBMHZWKFT-OQKWZONESA-N (2Z)-2-(3-ethyl-1H-benzimidazol-2-ylidene)-2-[5-methyl-2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NCCCN1CCCC1=O VCIMMQBMHZWKFT-OQKWZONESA-N 0.000 claims 1
- BFZLBFGOLMHLFP-XDJHFCHBSA-N (2Z)-2-[2-(cyclobutylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1H-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCC1 BFZLBFGOLMHLFP-XDJHFCHBSA-N 0.000 claims 1
- GSZIQJGZEVBYIZ-NBVRZTHBSA-N (2Z)-2-[2-(cyclobutylamino)pyrimidin-4-yl]-2-(3-ethyl-1H-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(N=1)=CC=NC=1NC1CCC1 GSZIQJGZEVBYIZ-NBVRZTHBSA-N 0.000 claims 1
- RYGLSICAFNZNMP-HEHNFIMWSA-N (2Z)-2-[2-(cyclohexylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1H-benzimidazol-2-ylidene)acetonitrile Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC1CCCCC1 RYGLSICAFNZNMP-HEHNFIMWSA-N 0.000 claims 1
- VJSBFVAZJBHKHH-GHRIWEEISA-N (2Z)-2-[2-(ethylamino)-5-methylpyrimidin-4-yl]-2-(3-ethyl-1H-benzimidazol-2-ylidene)acetonitrile Chemical compound CCNC1=NC=C(C)C(C(\C#N)=C/2N(C3=CC=CC=C3N\2)CC)=N1 VJSBFVAZJBHKHH-GHRIWEEISA-N 0.000 claims 1
- YCVWINWKMLREOP-VUODPORTSA-N (4R)-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-1,3-thiazolidine-4-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)[C@@H]1CSCN1 YCVWINWKMLREOP-VUODPORTSA-N 0.000 claims 1
- YCVWINWKMLREOP-COYFKBPASA-N (4S)-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]-1,3-thiazolidine-4-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)[C@H]1CSCN1 YCVWINWKMLREOP-COYFKBPASA-N 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZGGNPKDLUKSQGX-RELWKKBWSA-N 1-acetyl-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]piperidine-4-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)C1CCN(C(C)=O)CC1 ZGGNPKDLUKSQGX-RELWKKBWSA-N 0.000 claims 1
- QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 claims 1
- NRKMCUJASWHRQT-UHFFFAOYSA-N 2-(1,3-dihydrobenzimidazol-2-ylidene)-2-[5-methyl-2-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound N1=C(C(C#N)=C2NC3=CC=CC=C3N2)C(C)=CN=C1NCCCN1CCCC1=O NRKMCUJASWHRQT-UHFFFAOYSA-N 0.000 claims 1
- HSQAVTQYJVNJDR-UHFFFAOYSA-N 2-(1-ethylbenzimidazol-2-yl)-2-[2-(furan-2-ylmethylamino)-5-methylpyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCC1=CC=CO1 HSQAVTQYJVNJDR-UHFFFAOYSA-N 0.000 claims 1
- IKUFHLMBNSFBRO-UHFFFAOYSA-N 2-(1-ethylbenzimidazol-2-yl)-2-[2-[2-(1,2,4-triazol-1-yl)ethylamino]pyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(N=1)=CC=NC=1NCCN1C=NC=N1 IKUFHLMBNSFBRO-UHFFFAOYSA-N 0.000 claims 1
- ZRUAOSXJUQCCFP-UHFFFAOYSA-N 2-(1-ethylbenzimidazol-2-yl)-2-[5-methyl-2-(2-pyrazol-1-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCCN1C=CC=N1 ZRUAOSXJUQCCFP-UHFFFAOYSA-N 0.000 claims 1
- HPNDCMCOYAJERV-UHFFFAOYSA-N 2-(1H-benzimidazol-2-yl)-2-[5-methyl-2-(2-pyridin-3-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N1=C(C(C#N)C=2NC3=CC=CC=C3N=2)C(C)=CN=C1NCCC1=CC=CN=C1 HPNDCMCOYAJERV-UHFFFAOYSA-N 0.000 claims 1
- BOIZRKNKILSBTB-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)acetonitrile Chemical compound N#CCC1=NC=CN1 BOIZRKNKILSBTB-UHFFFAOYSA-N 0.000 claims 1
- LJLUHLMXSWYIKS-UHFFFAOYSA-N 2-(6-chloropyrimidin-4-yl)-2-(1,3-dihydrobenzimidazol-2-ylidene)acetonitrile Chemical compound C1=NC(Cl)=CC(C(C#N)=C2NC3=CC=CC=C3N2)=N1 LJLUHLMXSWYIKS-UHFFFAOYSA-N 0.000 claims 1
- BMHZAHGTGIZZCT-UHFFFAOYSA-N 2-[(4-bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone Chemical compound O=C1C2(C(NC(=O)C2)=O)C2=CC(F)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F BMHZAHGTGIZZCT-UHFFFAOYSA-N 0.000 claims 1
- NMMDPTXPHURZBR-UHFFFAOYSA-N 2-[2-(cyclohexylamino)pyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(N=1)=CC=NC=1NC1CCCCC1 NMMDPTXPHURZBR-UHFFFAOYSA-N 0.000 claims 1
- FQRCAUUSVDRERL-UHFFFAOYSA-N 2-[2-(cyclohexylmethylamino)-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCC1CCCCC1 FQRCAUUSVDRERL-UHFFFAOYSA-N 0.000 claims 1
- ZVHRVTZDDQMAJA-UHFFFAOYSA-N 2-[2-(cyclopentylamino)-5-methylpyrimidin-4-yl]-2-(1,3-diethylbenzimidazol-2-ylidene)acetonitrile Chemical compound CCN1C2=CC=CC=C2N(CC)C1=C(C#N)C(C(=CN=1)C)=NC=1NC1CCCC1 ZVHRVTZDDQMAJA-UHFFFAOYSA-N 0.000 claims 1
- ONTIOJUGXBWDJB-UHFFFAOYSA-N 2-[2-(cyclopentylamino)-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NC1CCCC1 ONTIOJUGXBWDJB-UHFFFAOYSA-N 0.000 claims 1
- DUZYLYSYBVQFFG-UHFFFAOYSA-N 2-[2-[2-[6-(dimethylamino)pyridin-3-yl]ethylamino]-5-methylpyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(C(=CN=1)C)=NC=1NCCC1=CC=C(N(C)C)N=C1 DUZYLYSYBVQFFG-UHFFFAOYSA-N 0.000 claims 1
- VAEWDFXXHLHBTG-UHFFFAOYSA-N 2-[2-[2-[6-(dimethylamino)pyridin-3-yl]ethylamino]pyrimidin-4-yl]-2-(1-ethylbenzimidazol-2-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C#N)C(N=1)=CC=NC=1NCCC1=CC=C(N(C)C)N=C1 VAEWDFXXHLHBTG-UHFFFAOYSA-N 0.000 claims 1
- ZVSDXQXCVBUOHA-UHFFFAOYSA-N 2-[5-methyl-3-oxo-4-(4,5,7-trifluoro-1,3-benzothiazol-2-yl)-1,4-benzothiazin-2-yl]acetic acid Chemical compound FC1=CC(F)=C2SC(N3C(=O)C(CC(O)=O)SC=4C=CC=C(C3=4)C)=NC2=C1F ZVSDXQXCVBUOHA-UHFFFAOYSA-N 0.000 claims 1
- OVKXDANNQWXYKF-UHFFFAOYSA-N 2-methyloctanamide Chemical compound CCCCCCC(C)C(N)=O OVKXDANNQWXYKF-UHFFFAOYSA-N 0.000 claims 1
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-DIHYDRO-4-OXO-3-((5-TRIFLUOROMETHYL-2-BENZOTHIAZOLYL)METHYL)-1-PHTHALAZINE ACETIC ACID Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 claims 1
- XFVQELOCUVVHQJ-LTGZKZEYSA-N 4-acetyl-N-[4-[(Z)-cyano-(3-ethyl-1H-benzimidazol-2-ylidene)methyl]-5-methylpyrimidin-2-yl]morpholine-2-carboxamide Chemical compound N1C2=CC=CC=C2N(CC)\C1=C(/C#N)C(C(=CN=1)C)=NC=1NC(=O)C1CN(C(C)=O)CCO1 XFVQELOCUVVHQJ-LTGZKZEYSA-N 0.000 claims 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
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| EP03102741 | 2003-09-12 | ||
| PCT/EP2004/052137 WO2005026155A1 (en) | 2003-09-12 | 2004-09-10 | Benzimidazole acetonitriles |
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| JP2007505085A JP2007505085A (ja) | 2007-03-08 |
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| EP (1) | EP1667995A1 (no) |
| JP (1) | JP2007505085A (no) |
| AU (1) | AU2004272306A1 (no) |
| CA (1) | CA2534317A1 (no) |
| IL (1) | IL174135A0 (no) |
| NO (1) | NO20061614L (no) |
| WO (1) | WO2005026155A1 (no) |
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|---|---|---|---|---|
| EP1812439B2 (en) | 2004-10-15 | 2017-12-06 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| CA2625210A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| SG175609A1 (en) | 2006-10-09 | 2011-11-28 | Takeda Pharmaceutical | Kinase inhibitors |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| CN113281309B (zh) * | 2021-05-17 | 2022-03-01 | 深圳市罗湖区人民医院 | 一种毒死蜱、多菌灵、阿特拉津三合一检测方法 |
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| EP1110957A1 (en) * | 1999-12-24 | 2001-06-27 | Applied Research Systems ARS Holding N.V. | Benzazole derivatives and their use as JNK modulators |
| AU2001295026B2 (en) * | 2000-09-06 | 2008-04-03 | Novartis Vaccines And Diagnostics, Inc. | Inhibitors of glycogen synthase kinase 3 |
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- 2004-09-10 AU AU2004272306A patent/AU2004272306A1/en not_active Abandoned
- 2004-09-10 WO PCT/EP2004/052137 patent/WO2005026155A1/en active Application Filing
- 2004-09-10 CA CA002534317A patent/CA2534317A1/en not_active Abandoned
- 2004-09-10 EP EP04766767A patent/EP1667995A1/en not_active Withdrawn
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2006
- 2006-03-06 IL IL174135A patent/IL174135A0/en unknown
- 2006-04-10 NO NO20061614A patent/NO20061614L/no not_active Application Discontinuation
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