KR20080076962A - 대사성 글루타메이트 수용체 조절제로서의 니코틴산 유도체 - Google Patents
대사성 글루타메이트 수용체 조절제로서의 니코틴산 유도체 Download PDFInfo
- Publication number
- KR20080076962A KR20080076962A KR1020087014836A KR20087014836A KR20080076962A KR 20080076962 A KR20080076962 A KR 20080076962A KR 1020087014836 A KR1020087014836 A KR 1020087014836A KR 20087014836 A KR20087014836 A KR 20087014836A KR 20080076962 A KR20080076962 A KR 20080076962A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- methanone
- chloro
- methyl
- piperidin
- 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.)
- Withdrawn
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000002503 metabolic effect Effects 0.000 title description 6
- 102000018899 Glutamate Receptors Human genes 0.000 title description 5
- 108010027915 Glutamate Receptors Proteins 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 90
- -1 4-Chloro-phenylamino Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 150000003839 salts Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 229910052720 vanadium Inorganic materials 0.000 claims description 16
- 239000012458 free base Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims description 13
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 208000012902 Nervous system disease Diseases 0.000 claims description 10
- 229930195712 glutamate Natural products 0.000 claims description 10
- 230000019491 signal transduction Effects 0.000 claims description 10
- 208000025966 Neurological disease Diseases 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 208000026723 Urinary tract disease Diseases 0.000 claims description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 208000014001 urinary system disease Diseases 0.000 claims description 7
- 210000001635 urinary tract Anatomy 0.000 claims description 7
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- DPPFDGYZSWUHCO-UHFFFAOYSA-N [5-chloro-6-(4-chloroanilino)pyridin-3-yl]-(3-ethylpiperidin-1-yl)methanone Chemical compound C1C(CC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(Cl)C=C1 DPPFDGYZSWUHCO-UHFFFAOYSA-N 0.000 claims description 3
- RSUJGAKZLRLZPU-UHFFFAOYSA-N [5-chloro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-(3-ethylpiperidin-1-yl)methanone Chemical compound C1C(CC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(OC)N=C1 RSUJGAKZLRLZPU-UHFFFAOYSA-N 0.000 claims description 3
- LGCIZDYPKPLDMP-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(3-ethylpiperidin-1-yl)methanone Chemical compound C1C(CC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 LGCIZDYPKPLDMP-UHFFFAOYSA-N 0.000 claims description 3
- SZTSAJHGMRUJJW-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(3-propylpiperidin-1-yl)methanone Chemical compound C1C(CCC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 SZTSAJHGMRUJJW-UHFFFAOYSA-N 0.000 claims description 3
- JIWDGCYERQLPRJ-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[2-(1,2-difluoropropyl)piperidin-1-yl]methanone Chemical compound CC(F)C(F)C1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 JIWDGCYERQLPRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- UJXARZKVVMYUID-UHFFFAOYSA-N (2-butylpiperidin-1-yl)-[5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound CCCCC1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 UJXARZKVVMYUID-UHFFFAOYSA-N 0.000 claims description 2
- SWIWMNLQMFQOIQ-UHFFFAOYSA-N (3-methylpiperidin-1-yl)-[6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1C(C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CC=C(C)N=C1 SWIWMNLQMFQOIQ-UHFFFAOYSA-N 0.000 claims description 2
- GWKMILBGLNCMDT-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl-[6-(4-chloroanilino)pyridin-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1NC1=CC=C(C(=O)N2C3CCCCC3CCC2)C=N1 GWKMILBGLNCMDT-UHFFFAOYSA-N 0.000 claims description 2
- HMEYSJFADDJQMK-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptan-3-yl-[5-chloro-6-(4-chloroanilino)pyridin-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1NC1=NC=C(C(=O)N2C3CCC(C3)C2)C=C1Cl HMEYSJFADDJQMK-UHFFFAOYSA-N 0.000 claims description 2
- PUQAHZPHRXPSAW-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptan-3-yl-[5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C3CCC(C3)C2)C=C1Cl PUQAHZPHRXPSAW-UHFFFAOYSA-N 0.000 claims description 2
- YYJWLVXOBIMSBS-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptan-3-yl-[6-(4-chloroanilino)pyridin-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1NC1=CC=C(C(=O)N2C3CCC(C3)C2)C=N1 YYJWLVXOBIMSBS-UHFFFAOYSA-N 0.000 claims description 2
- ZGZXNOYLBQRQEQ-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonan-3-yl-[6-(4-chloroanilino)pyridin-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1NC1=CC=C(C(=O)N2CC3CCC(CC3)C2)C=N1 ZGZXNOYLBQRQEQ-UHFFFAOYSA-N 0.000 claims description 2
- MMICSADTCABNEZ-UHFFFAOYSA-N 4-[[5-(piperidine-1-carbonyl)pyridin-2-yl]amino]benzonitrile Chemical compound C=1C=C(NC=2C=CC(=CC=2)C#N)N=CC=1C(=O)N1CCCCC1 MMICSADTCABNEZ-UHFFFAOYSA-N 0.000 claims description 2
- FQRXQZIMRWMVJZ-UHFFFAOYSA-N 6-(4-chloroanilino)-n,n-bis(2-methoxyethyl)pyridine-3-carboxamide;hydrochloride Chemical compound Cl.N1=CC(C(=O)N(CCOC)CCOC)=CC=C1NC1=CC=C(Cl)C=C1 FQRXQZIMRWMVJZ-UHFFFAOYSA-N 0.000 claims description 2
- PZOCGYNJNIAIFX-UHFFFAOYSA-N 6-(4-chloroanilino)-n,n-diethylpyridine-3-carboxamide;hydrochloride Chemical compound Cl.N1=CC(C(=O)N(CC)CC)=CC=C1NC1=CC=C(Cl)C=C1 PZOCGYNJNIAIFX-UHFFFAOYSA-N 0.000 claims description 2
- CNXYZDAVBOOYFI-UHFFFAOYSA-N C1C(C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CC=C(C)C=C1 Chemical compound C1C(C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CC=C(C)C=C1 CNXYZDAVBOOYFI-UHFFFAOYSA-N 0.000 claims description 2
- AJBIHMIWLPKLGM-UHFFFAOYSA-N ClC=1C=C(C=NC1NC=1C=NC(=CC1)C)C(=O)N1C(CCCC1)COC Chemical compound ClC=1C=C(C=NC1NC=1C=NC(=CC1)C)C(=O)N1C(CCCC1)COC AJBIHMIWLPKLGM-UHFFFAOYSA-N 0.000 claims description 2
- KCYALLWYTNHKAL-KAECKJJSSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[6-(4-methoxyanilino)pyridin-3-yl]methanone;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1NC1=CC=C(C(=O)N2C[C@@H](C)O[C@@H](C)C2)C=N1 KCYALLWYTNHKAL-KAECKJJSSA-N 0.000 claims description 2
- RWTCDXRKDVGOGQ-KBGJBQQCSA-N [(2s,6r)-2,6-dimethylmorpholin-4-yl]-[6-(4-methylanilino)pyridin-3-yl]methanone;hydrochloride Chemical compound Cl.C1[C@@H](C)O[C@@H](C)CN1C(=O)C(C=N1)=CC=C1NC1=CC=C(C)C=C1 RWTCDXRKDVGOGQ-KBGJBQQCSA-N 0.000 claims description 2
- DSXSVCBJSYRQQI-WWPJHQMMSA-N [(3ar,4s,7ar)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2h-indol-1-yl]-[6-(4-chloroanilino)pyridin-3-yl]methanone Chemical compound CC1=CC=CC(C#C[C@@]2(O)[C@H]3[C@H](N(CC3)C(=O)C=3C=NC(NC=4C=CC(Cl)=CC=4)=CC=3)CCC2)=C1 DSXSVCBJSYRQQI-WWPJHQMMSA-N 0.000 claims description 2
- SWIWMNLQMFQOIQ-CYBMUJFWSA-N [(3r)-3-methylpiperidin-1-yl]-[6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1[C@H](C)CCCN1C(=O)C(C=N1)=CC=C1NC1=CC=C(C)N=C1 SWIWMNLQMFQOIQ-CYBMUJFWSA-N 0.000 claims description 2
- HCZSOHKUGRDVGS-UHFFFAOYSA-N [2-(2-chloroethyl)piperidin-1-yl]-[5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C(CCCC2)CCCl)C=C1Cl HCZSOHKUGRDVGS-UHFFFAOYSA-N 0.000 claims description 2
- SELOANINQSRULN-UHFFFAOYSA-N [2-(4-chloroanilino)pyrimidin-5-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(C=N1)=CN=C1NC1=CC=C(Cl)C=C1 SELOANINQSRULN-UHFFFAOYSA-N 0.000 claims description 2
- PPCTWQBFGQSKNF-UHFFFAOYSA-N [2-(4-chloroanilino)pyrimidin-5-yl]-piperidin-1-ylmethanone Chemical compound C1=CC(Cl)=CC=C1NC1=NC=C(C(=O)N2CCCCC2)C=N1 PPCTWQBFGQSKNF-UHFFFAOYSA-N 0.000 claims description 2
- AKRBCPCYMFKJLQ-UHFFFAOYSA-N [5-chloro-6-(4-chloroanilino)pyridin-3-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(Cl)C=C1 AKRBCPCYMFKJLQ-UHFFFAOYSA-N 0.000 claims description 2
- COGYAXFYJYPHMB-MRXNPFEDSA-N [5-chloro-6-(4-chloroanilino)pyridin-3-yl]-[(2r)-2-ethylpiperidin-1-yl]methanone Chemical compound CC[C@@H]1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(Cl)C=C1 COGYAXFYJYPHMB-MRXNPFEDSA-N 0.000 claims description 2
- AKRBCPCYMFKJLQ-GFCCVEGCSA-N [5-chloro-6-(4-chloroanilino)pyridin-3-yl]-[(3r)-3-methylpiperidin-1-yl]methanone Chemical compound C1[C@H](C)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(Cl)C=C1 AKRBCPCYMFKJLQ-GFCCVEGCSA-N 0.000 claims description 2
- VXAPJZCQXDWDAM-UHFFFAOYSA-N [5-chloro-6-(4-chloroanilino)pyridin-3-yl]-thiomorpholin-4-ylmethanone Chemical compound C1=CC(Cl)=CC=C1NC1=NC=C(C(=O)N2CCSCC2)C=C1Cl VXAPJZCQXDWDAM-UHFFFAOYSA-N 0.000 claims description 2
- UGQUHSOZGAXYAF-UHFFFAOYSA-N [5-chloro-6-(6-methylpyridin-3-yl)oxypyridin-3-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(C=C1Cl)=CN=C1OC1=CC=C(C)N=C1 UGQUHSOZGAXYAF-UHFFFAOYSA-N 0.000 claims description 2
- USDAMGIKDUKVRT-UHFFFAOYSA-N [5-chloro-6-(6-methylpyridin-3-yl)oxypyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NC(C)=CC=C1OC1=NC=C(C(=O)N2CCCCC2)C=C1Cl USDAMGIKDUKVRT-UHFFFAOYSA-N 0.000 claims description 2
- ASQCZKIOAOKASX-UHFFFAOYSA-N [5-chloro-6-[(2-methylpyrimidin-5-yl)amino]pyridin-3-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CN=C(C)N=C1 ASQCZKIOAOKASX-UHFFFAOYSA-N 0.000 claims description 2
- QQRYEDUACWVZPN-UHFFFAOYSA-N [5-chloro-6-[(2-methylpyrimidin-5-yl)amino]pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NC(C)=NC=C1NC1=NC=C(C(=O)N2CCCCC2)C=C1Cl QQRYEDUACWVZPN-UHFFFAOYSA-N 0.000 claims description 2
- KRYCHJKEVPBGLJ-UHFFFAOYSA-N [5-chloro-6-[(6-chloropyridin-3-yl)amino]pyridin-3-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1C(C)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(Cl)N=C1 KRYCHJKEVPBGLJ-UHFFFAOYSA-N 0.000 claims description 2
- ZQEPVYVYLFEYKM-UHFFFAOYSA-N [5-chloro-6-[(6-ethoxypyridin-3-yl)amino]pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NC(OCC)=CC=C1NC1=NC=C(C(=O)N2CCCCC2)C=C1Cl ZQEPVYVYLFEYKM-UHFFFAOYSA-N 0.000 claims description 2
- PNHZFWLYJDGOLU-UHFFFAOYSA-N [5-chloro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-(3-methylpiperidin-1-yl)methanone Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(=O)N2CC(C)CCC2)C=C1Cl PNHZFWLYJDGOLU-UHFFFAOYSA-N 0.000 claims description 2
- RCJJQWIMWHHYKR-OAHLLOKOSA-N [5-chloro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[(2r)-2-ethylpiperidin-1-yl]methanone Chemical compound CC[C@@H]1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(OC)N=C1 RCJJQWIMWHHYKR-OAHLLOKOSA-N 0.000 claims description 2
- WEOPTLDGFWFBEE-UHFFFAOYSA-N [5-chloro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-piperidin-1-ylmethanone Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C(=O)N2CCCCC2)C=C1Cl WEOPTLDGFWFBEE-UHFFFAOYSA-N 0.000 claims description 2
- NOPAHYIDPVHNJJ-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(1,3-thiazolidin-3-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2CSCC2)C=C1Cl NOPAHYIDPVHNJJ-UHFFFAOYSA-N 0.000 claims description 2
- VGEGNQZLKASKLL-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2,2,6,6-tetramethylpiperidin-1-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C(CCCC2(C)C)(C)C)C=C1Cl VGEGNQZLKASKLL-UHFFFAOYSA-N 0.000 claims description 2
- UKUMGXODPZJWJX-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2,3-diethylpiperidin-1-yl)methanone Chemical compound CCC1C(CC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 UKUMGXODPZJWJX-UHFFFAOYSA-N 0.000 claims description 2
- FCZFMKAXRZXYQE-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2,3-dimethylpiperidin-1-yl)methanone Chemical compound CC1C(C)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 FCZFMKAXRZXYQE-UHFFFAOYSA-N 0.000 claims description 2
- XIEKNGTZCOUPDV-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2,6-dimethylpiperidin-1-yl)methanone Chemical compound CC1CCCC(C)N1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 XIEKNGTZCOUPDV-UHFFFAOYSA-N 0.000 claims description 2
- MKKRTZXTLADIPV-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-ethenylpiperidin-1-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C(CCCC2)C=C)C=C1Cl MKKRTZXTLADIPV-UHFFFAOYSA-N 0.000 claims description 2
- QABUURICQJOWID-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-ethylpiperidin-1-yl)methanone Chemical compound CCC1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 QABUURICQJOWID-UHFFFAOYSA-N 0.000 claims description 2
- GCFLCUNUJNVWKN-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-phenylpiperidin-1-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C(CCCC2)C=2C=CC=CC=2)C=C1Cl GCFLCUNUJNVWKN-UHFFFAOYSA-N 0.000 claims description 2
- LJIWJCVCVUTOHU-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-phenylpyrrolidin-1-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2C(CCC2)C=2C=CC=CC=2)C=C1Cl LJIWJCVCVUTOHU-UHFFFAOYSA-N 0.000 claims description 2
- TWZOJPNADIKKCZ-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-propan-2-ylpiperidin-1-yl)methanone Chemical compound CC(C)C1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 TWZOJPNADIKKCZ-UHFFFAOYSA-N 0.000 claims description 2
- IGYYSPYIYHWVSO-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-propyl-1,3-oxazinan-3-yl)methanone Chemical compound CCCC1OCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 IGYYSPYIYHWVSO-UHFFFAOYSA-N 0.000 claims description 2
- JFVQMYLXIIQSQB-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(2-propylpiperidin-1-yl)methanone Chemical compound CCCC1CCCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 JFVQMYLXIIQSQB-UHFFFAOYSA-N 0.000 claims description 2
- FZMFLXACJCTCMA-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(3-cyclopropylpiperidin-1-yl)methanone Chemical compound C1=NC(C)=CC=C1NC1=NC=C(C(=O)N2CC(CCC2)C2CC2)C=C1Cl FZMFLXACJCTCMA-UHFFFAOYSA-N 0.000 claims description 2
- DFEKWACAOYHWTB-UHFFFAOYSA-N [5-chloro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-(3-ethylidenepiperidin-1-yl)methanone Chemical compound C1C(=CC)CCCN1C(=O)C(C=C1Cl)=CN=C1NC1=CC=C(C)N=C1 DFEKWACAOYHWTB-UHFFFAOYSA-N 0.000 claims description 2
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- Psychiatry (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Addiction (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05027934.8 | 2005-12-20 | ||
| EP05027934 | 2005-12-20 | ||
| EP06120424.4 | 2006-09-11 | ||
| EP06120424 | 2006-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080076962A true KR20080076962A (ko) | 2008-08-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087014836A Withdrawn KR20080076962A (ko) | 2005-12-20 | 2006-12-18 | 대사성 글루타메이트 수용체 조절제로서의 니코틴산 유도체 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20090005363A1 (https=) |
| EP (1) | EP1966144A1 (https=) |
| JP (1) | JP2009519986A (https=) |
| KR (1) | KR20080076962A (https=) |
| AR (1) | AR058554A1 (https=) |
| AU (1) | AU2006329007A1 (https=) |
| BR (1) | BRPI0620066A2 (https=) |
| CA (1) | CA2627630A1 (https=) |
| PE (1) | PE20071171A1 (https=) |
| RU (1) | RU2008129622A (https=) |
| TW (1) | TW200732323A (https=) |
| WO (1) | WO2007071358A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010502664A (ja) | 2006-09-11 | 2010-01-28 | ノバルティス アクチエンゲゼルシャフト | 代謝型グルタミン酸受容体の調節剤としてのニコチン酸誘導体 |
| JP5341084B2 (ja) * | 2007-08-03 | 2013-11-13 | エフ.ホフマン−ラ ロシュ アーゲー | Taar1リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
| AU2008309621A1 (en) * | 2007-10-12 | 2009-04-16 | Novartis Ag | Metabotropic glutamate receptor modulators for the treatment of Parkinson's Disease |
| WO2009047303A2 (en) * | 2007-10-12 | 2009-04-16 | Novartis Ag | Metabotropic glutamate receptor modulators for the treatment of pervasive developmental disorder |
| MX2010014222A (es) * | 2008-06-30 | 2011-03-29 | Novartis Ag Star | Combinaciones que comprenden moduladores de mglur para el tratamiento de enfermedad de parkinson. |
| CN102256963B (zh) * | 2008-12-19 | 2014-06-11 | 贝林格尔.英格海姆国际有限公司 | 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺 |
| US8748623B2 (en) | 2009-02-17 | 2014-06-10 | Syntrix Biosystems, Inc. | Pyridinecarboxamides as CXCR2 modulators |
| EP2959902A1 (en) | 2009-07-23 | 2015-12-30 | Novartis AG | Use of azabicycloalkyl derivatives for the treatment or prevention of ataxia |
| NZ598891A (en) * | 2009-08-24 | 2014-05-30 | Neuralstem Inc | Synthesis of a neurostimulative piperazine |
| RU2012116124A (ru) * | 2009-09-21 | 2013-10-27 | Вандербилт Юниверсити | О-БЕНЗИЛ НИКОТИНАМИДНЫЕ АНАЛОГИ КАК ПОЗИТИВНЫЕ АЛЛОСТЕРИЧЕСКИЕ МОДУЛЯТОРЫ mGluR5 |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| EP2490691A1 (en) | 2009-10-20 | 2012-08-29 | Novartis AG | Use of 1h-quinazoline-2,4-diones |
| ES2674275T3 (es) | 2009-12-17 | 2018-06-28 | Centrexion Therapeutics Corporation | Antagonistas del receptor CCR2 y usos de los mismos |
| WO2011149963A1 (en) * | 2010-05-24 | 2011-12-01 | Vanderbilt University | Substituted-6-methylnicotinamides as mglur5 positive allosteric modulators |
| AU2011268865A1 (en) | 2010-06-24 | 2013-01-31 | Novartis Ag | Use of 1H-quinazoline-2,4-diones |
| EP2608672B1 (en) | 2010-08-23 | 2020-12-16 | Syntrix Biosystems, Inc. | Aminopyridine- and aminopyrimidinecarboxamides as cxcr2 modulators |
| AR084515A1 (es) * | 2010-12-22 | 2013-05-22 | Merz Pharma Gmbh & Co Kgaa | Derivados heterociclicos nitrogenados, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de enfermedades asociadas al sistema nervioso central tales como parkinson y alzheimer, entre otras |
| AR084516A1 (es) * | 2010-12-22 | 2013-05-22 | Merz Pharma Gmbh & Co Kgaa | Moduladores de receptores de glutamato metabotropicos |
| WO2012101060A1 (en) | 2011-01-27 | 2012-08-02 | Novartis Ag | Use of nicotinic acetylcholine receptor alpha 7 activators |
| MX2014002693A (es) | 2011-09-07 | 2014-06-04 | Novartis Ag | Uso de 1h-quinazolina-2,4-dionas para usarse en la prevencion o el tratamiento de epilepsia fotosensible. |
| RU2672468C1 (ru) * | 2011-12-22 | 2018-11-15 | Конекшис Лайф Сайенсиз Пвт. Лтд. | Производные аза-адамантанов и их применение |
| MX362819B (es) | 2013-01-15 | 2019-02-18 | Novartis Ag | Uso de agonistas del receptor nicotinico de acetilcolina alfa 7 para el tratamiento de la narcolepsia. |
| KR101879919B1 (ko) | 2013-01-15 | 2018-07-18 | 노파르티스 아게 | 알파 7 니코틴성 아세틸콜린 수용체 작용물질의 용도 |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
| TWI621618B (zh) | 2013-03-13 | 2018-04-21 | 比利時商健生藥品公司 | 經取代2-氮雜雙環類及其作為食慾素受體調控劑之用途 |
| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| US10561676B2 (en) | 2013-08-02 | 2020-02-18 | Syntrix Biosystems Inc. | Method for treating cancer using dual antagonists of CXCR1 and CXCR2 |
| US10046002B2 (en) | 2013-08-02 | 2018-08-14 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| US8969365B2 (en) | 2013-08-02 | 2015-03-03 | Syntrix Biosystems, Inc. | Thiopyrimidinecarboxamides as CXCR1/2 modulators |
| JPWO2015098991A1 (ja) * | 2013-12-26 | 2017-03-23 | 東レ株式会社 | N−アルキルアミド誘導体及びその医薬用途 |
| KR102455043B1 (ko) * | 2014-09-11 | 2022-10-13 | 얀센 파마슈티카 엔.브이. | 치환된 2-아자바이사이클 및 오렉신 수용체 조절제로서의 이의 용도 |
| PT3317270T (pt) | 2015-07-02 | 2020-08-24 | Centrexion Therapeutics Corp | (4-((3r,4r)-3-metoxitetrahidro-pirano-4-ilamino)piperidina-1-il)(5-metil-6-(((2r,6s)-6-(p-tolil)tetrahidro-2h-pirano-2-il)metilamino)pirimidina-4-il)citrato de metanona |
| US20190231525A1 (en) | 2016-08-01 | 2019-08-01 | Mitraltech Ltd. | Minimally-invasive delivery systems |
| DE102018104201A1 (de) * | 2018-02-23 | 2019-08-29 | Westfälische Wilhelms-Universität Münster | Verfahren zur Herstellung fluorierten heterocyclischen aliphatischer Verbindungen |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE817911C (de) * | 1947-12-16 | 1951-10-22 | Chem Fab Tempelhof Preuss & Te | Verfahren zur Darstellung von in 6-Stellung basisch substituierten Pyridin-3-carbonsaeureamiden |
| WO1999018066A1 (en) * | 1997-10-02 | 1999-04-15 | Sankyo Company, Limited | Amidocarboxylic acid derivatives |
| AU9781098A (en) * | 1997-10-02 | 1999-04-27 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| CN1158264C (zh) * | 1997-11-21 | 2004-07-21 | Nps药物有限公司 | 用于治疗中枢神经系统疾病的代谢性谷氨酸受体拮抗剂 |
| DK1196397T3 (da) * | 1999-06-02 | 2006-01-02 | Nps Pharma Inc | Metabotrope glutamatreceptorantagonister og anvendelse deraf til behandling af sygdomme i centralnervesystemet |
| WO2001007416A1 (de) * | 1999-07-28 | 2001-02-01 | Lonza Ag | Verfahren zur herstellung von pyridazincarbonsäurederivaten |
| US6479510B2 (en) * | 2000-08-18 | 2002-11-12 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| WO2003022214A2 (en) * | 2001-09-06 | 2003-03-20 | Millennium Pharmaceuticals, Inc. | Piperazine and homopiperazine compounds |
| US7595311B2 (en) * | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| KR101025633B1 (ko) * | 2002-09-19 | 2011-03-30 | 일라이 릴리 앤드 캄파니 | 오피오이드 수용체 안타고니스트로서의 디아릴 에테르 |
| US20040067985A1 (en) * | 2002-10-04 | 2004-04-08 | Fortuna Haviv | Method of inhibiting angiogenesis |
| NZ551468A (en) * | 2003-12-24 | 2010-05-28 | Biota Scient Management | Polycyclic agents for the treatment of respiratory syncytial virus infections |
| WO2005110982A2 (en) * | 2004-04-07 | 2005-11-24 | Neurogen Corporation | Substituted 1-benzyl-4-substituted piperazine analogues |
| DE102004020908A1 (de) * | 2004-04-28 | 2005-11-17 | Grünenthal GmbH | Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen |
| SE0401969D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidine derivatives |
| ES2377758T3 (es) * | 2004-11-12 | 2012-03-30 | Bristol-Myers Squibb Company | Compuestos tricíclicos basados en tiazolo[4,5-b]piridina imidazo-fusionada y composiciones farmacéuticas que los comprenden |
| WO2006064286A1 (en) * | 2004-12-13 | 2006-06-22 | Medivir Uk Ltd | Cathepsin s inhibitors |
| WO2006094639A1 (en) * | 2005-03-04 | 2006-09-14 | F.Hoffmann-La Roche Ag | Pyridine-2-carboxamide derivatives as mglur5 antagonists |
-
2006
- 2006-12-18 AU AU2006329007A patent/AU2006329007A1/en not_active Abandoned
- 2006-12-18 CA CA002627630A patent/CA2627630A1/en not_active Abandoned
- 2006-12-18 EP EP06829702A patent/EP1966144A1/en not_active Withdrawn
- 2006-12-18 KR KR1020087014836A patent/KR20080076962A/ko not_active Withdrawn
- 2006-12-18 JP JP2008546217A patent/JP2009519986A/ja active Pending
- 2006-12-18 RU RU2008129622/04A patent/RU2008129622A/ru not_active Application Discontinuation
- 2006-12-18 AR ARP060105586A patent/AR058554A1/es not_active Application Discontinuation
- 2006-12-18 WO PCT/EP2006/012181 patent/WO2007071358A1/en not_active Ceased
- 2006-12-18 BR BRPI0620066-4A patent/BRPI0620066A2/pt not_active IP Right Cessation
- 2006-12-18 US US12/158,387 patent/US20090005363A1/en not_active Abandoned
- 2006-12-19 TW TW095147659A patent/TW200732323A/zh unknown
- 2006-12-20 PE PE2006001666A patent/PE20071171A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200732323A (en) | 2007-09-01 |
| BRPI0620066A2 (pt) | 2011-11-01 |
| AR058554A1 (es) | 2008-02-13 |
| PE20071171A1 (es) | 2008-01-22 |
| US20090005363A1 (en) | 2009-01-01 |
| WO2007071358A1 (en) | 2007-06-28 |
| CA2627630A1 (en) | 2007-06-28 |
| JP2009519986A (ja) | 2009-05-21 |
| EP1966144A1 (en) | 2008-09-10 |
| RU2008129622A (ru) | 2010-01-27 |
| AU2006329007A1 (en) | 2007-06-28 |
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