RU2011141188A - Замещенные 2-меркаптохинолин-3-карбоксамиды в качестве kcnq2/3 модуляторов - Google Patents
Замещенные 2-меркаптохинолин-3-карбоксамиды в качестве kcnq2/3 модуляторов Download PDFInfo
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- RU2011141188A RU2011141188A RU2011141188/04A RU2011141188A RU2011141188A RU 2011141188 A RU2011141188 A RU 2011141188A RU 2011141188/04 A RU2011141188/04 A RU 2011141188/04A RU 2011141188 A RU2011141188 A RU 2011141188A RU 2011141188 A RU2011141188 A RU 2011141188A
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- Russia
- Prior art keywords
- alkyl
- methyl
- carboxamide
- quinoline
- ethylsulfanyl
- Prior art date
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- 102000005453 KCNQ2 Potassium Channel Human genes 0.000 title 1
- 108010006746 KCNQ2 Potassium Channel Proteins 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 81
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 65
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 38
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 26
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 22
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 6
- CKWKREFECQVBBZ-UHFFFAOYSA-N 2-sulfanylidene-1h-quinoline-3-carboxamide Chemical class C1=CC=C2N=C(S)C(C(=O)N)=CC2=C1 CKWKREFECQVBBZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 46
- -1 3-chloro-2-hydroxypropylthio Chemical group 0.000 claims 32
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 22
- 125000004076 pyridyl group Chemical group 0.000 claims 22
- 125000001544 thienyl group Chemical group 0.000 claims 21
- 150000003857 carboxamides Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 4
- 206010046543 Urinary incontinence Diseases 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 208000012661 Dyskinesia Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- KGTWXLZUIRMNID-UHFFFAOYSA-N 2-(2-phenylsulfanylethylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCSC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 KGTWXLZUIRMNID-UHFFFAOYSA-N 0.000 claims 1
- BRDPCVBAVSHWJG-UHFFFAOYSA-N 2-(3-cyclohexylpropylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCCC2CCCCC2)C=1C(=O)NCC1=CC=CS1 BRDPCVBAVSHWJG-UHFFFAOYSA-N 0.000 claims 1
- DCPMSEUNUUZOKE-UHFFFAOYSA-N 2-(3-phenylpropylsulfanyl)-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCCC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 DCPMSEUNUUZOKE-UHFFFAOYSA-N 0.000 claims 1
- DKXNTGWJGKSAJN-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)sulfanylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(F)=CC=C1SCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 DKXNTGWJGKSAJN-UHFFFAOYSA-N 0.000 claims 1
- LGLZFNXJLHWYLR-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)sulfonylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 LGLZFNXJLHWYLR-UHFFFAOYSA-N 0.000 claims 1
- XNTODQLICDNQKF-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfanylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1SCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 XNTODQLICDNQKF-UHFFFAOYSA-N 0.000 claims 1
- VZFKPENHJUZZDW-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonylethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 VZFKPENHJUZZDW-UHFFFAOYSA-N 0.000 claims 1
- KNVVYVSPKSXKSE-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(2-cyclohexylethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCCC1CCCCC1 KNVVYVSPKSXKSE-UHFFFAOYSA-N 0.000 claims 1
- IXAZYBWMTOQTNB-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(3,3-dimethylbutyl)quinoline-3-carboxamide Chemical compound CC(C)(C)CCNC(=O)C1=CC2=CC=CC=C2N=C1SCCS(=O)(=O)C1=CC=CC=C1 IXAZYBWMTOQTNB-UHFFFAOYSA-N 0.000 claims 1
- ICECDKYGZLCPCK-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(cyclohexylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCC1CCCCC1 ICECDKYGZLCPCK-UHFFFAOYSA-N 0.000 claims 1
- WAUDLZDKCYBPFH-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-5-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CSC=1CNC(=O)C=1C=C2C(C(F)(F)F)=CC=CC2=NC=1SCCS(=O)(=O)C1=CC=CC=C1 WAUDLZDKCYBPFH-UHFFFAOYSA-N 0.000 claims 1
- QSTRXYDQLKNNRG-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CSC=1CNC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N=C1SCCS(=O)(=O)C1=CC=CC=C1 QSTRXYDQLKNNRG-UHFFFAOYSA-N 0.000 claims 1
- IDAUDNJJPNYANF-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)CCSC1=NC2=CC(C(F)(F)F)=CC=C2C=C1C(=O)NCC1=CC=CS1 IDAUDNJJPNYANF-UHFFFAOYSA-N 0.000 claims 1
- RBTMWCQEJUGFEI-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)ethylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C=1C2=CC=CC=C2N=C(SCCS(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 RBTMWCQEJUGFEI-UHFFFAOYSA-N 0.000 claims 1
- SVTHLGYCZILPPE-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 SVTHLGYCZILPPE-UHFFFAOYSA-N 0.000 claims 1
- CAMGJASCBPTCFP-UHFFFAOYSA-N 2-[3-(4-methylphenyl)propylsulfanyl]-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound C1=CC(C)=CC=C1CCCSC1=NC2=CC=CC=C2C=C1C(=O)NCC1=CC=CS1 CAMGJASCBPTCFP-UHFFFAOYSA-N 0.000 claims 1
- JWWSIJYBINTJOV-UHFFFAOYSA-N 2-benzylsulfanyl-n-[(3-fluorophenyl)methyl]-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1C=CC=CC=1CSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 JWWSIJYBINTJOV-UHFFFAOYSA-N 0.000 claims 1
- TWWCMRROISPVRQ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[(2,4,5-trifluorophenyl)methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC(F)=C(F)C=C1F TWWCMRROISPVRQ-UHFFFAOYSA-N 0.000 claims 1
- JEIFVPVLNYRPCS-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[(3,4,5-trifluorophenyl)methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC(F)=C(F)C(F)=C1 JEIFVPVLNYRPCS-UHFFFAOYSA-N 0.000 claims 1
- DYKKVRUTCYJBGB-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[[3-(trifluoromethyl)phenyl]methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 DYKKVRUTCYJBGB-UHFFFAOYSA-N 0.000 claims 1
- RGAFQVDDHODCOV-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[[4-(trifluoromethyl)phenyl]methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C(F)(F)F)C=C1 RGAFQVDDHODCOV-UHFFFAOYSA-N 0.000 claims 1
- JHCSBJAEVLXSGL-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)-n-[[4-(trifluoromethylsulfanyl)phenyl]methyl]quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(SC(F)(F)F)C=C1 JHCSBJAEVLXSGL-UHFFFAOYSA-N 0.000 claims 1
- FBCCCXHQDZEHAC-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(1,3-thiazol-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=NC=CS1 FBCCCXHQDZEHAC-UHFFFAOYSA-N 0.000 claims 1
- XUGHLZBAJAZKQZ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(2-phenylethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCCC1=CC=CC=C1 XUGHLZBAJAZKQZ-UHFFFAOYSA-N 0.000 claims 1
- CSFVPXMKBCZQBY-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(3-methylbutyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC=C2C(C)=C(C(=O)NCCC(C)C)C(SCC)=NC2=C1 CSFVPXMKBCZQBY-UHFFFAOYSA-N 0.000 claims 1
- KZGVSMQUEAHERR-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(3-phenylpropyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCCCC1=CC=CC=C1 KZGVSMQUEAHERR-UHFFFAOYSA-N 0.000 claims 1
- MWGVUZKBKRYEKP-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(4-methylpentyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC=C2C(C)=C(C(=O)NCCCC(C)C)C(SCC)=NC2=C1 MWGVUZKBKRYEKP-UHFFFAOYSA-N 0.000 claims 1
- FNBFBAAXYARCLB-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(pyridin-2-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC=N1 FNBFBAAXYARCLB-UHFFFAOYSA-N 0.000 claims 1
- ZXWBBKUQWALZRY-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(pyridin-3-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CN=C1 ZXWBBKUQWALZRY-UHFFFAOYSA-N 0.000 claims 1
- WJVVKGGHLHKRFE-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(pyridin-4-ylmethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=NC=C1 WJVVKGGHLHKRFE-UHFFFAOYSA-N 0.000 claims 1
- AYYXMMBTPXLNMB-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-(thiophen-2-ylmethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC=C2C(C)=C1C(=O)NCC1=CC=CS1 AYYXMMBTPXLNMB-UHFFFAOYSA-N 0.000 claims 1
- SFNWNEULSOKQDG-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(2-methylphenyl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC=C1C SFNWNEULSOKQDG-UHFFFAOYSA-N 0.000 claims 1
- BHCUNBSVUBPQHJ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(3-methylphenyl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(C)=C1 BHCUNBSVUBPQHJ-UHFFFAOYSA-N 0.000 claims 1
- NCTJTIHXQVHHTQ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(4-methylphenyl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C)C=C1 NCTJTIHXQVHHTQ-UHFFFAOYSA-N 0.000 claims 1
- FVLUNDJABKIFLB-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(4-methylthiophen-2-yl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC(C)=CS1 FVLUNDJABKIFLB-UHFFFAOYSA-N 0.000 claims 1
- BPZASLDQFMWJDE-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(5-methylfuran-2-yl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C)O1 BPZASLDQFMWJDE-UHFFFAOYSA-N 0.000 claims 1
- MESBCMXZDOPINP-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-[(5-methylthiophen-2-yl)methyl]-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C)S1 MESBCMXZDOPINP-UHFFFAOYSA-N 0.000 claims 1
- QWGINHANBPWPEJ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-pentyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2N=C(SCC)C(C(=O)NCCCCC)=C(C)C2=C1 QWGINHANBPWPEJ-UHFFFAOYSA-N 0.000 claims 1
- BQUSIWROFGNJHZ-UHFFFAOYSA-N 2-ethylsulfanyl-4-methyl-n-propyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2N=C(SCC)C(C(=O)NCCC)=C(C)C2=C1 BQUSIWROFGNJHZ-UHFFFAOYSA-N 0.000 claims 1
- FVZVRJDBPYZXNJ-UHFFFAOYSA-N 2-ethylsulfanyl-5-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(F)=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 FVZVRJDBPYZXNJ-UHFFFAOYSA-N 0.000 claims 1
- INILATDIIGNRRP-UHFFFAOYSA-N 2-ethylsulfanyl-5-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(F)=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 INILATDIIGNRRP-UHFFFAOYSA-N 0.000 claims 1
- XAJZZLZZOGAEOE-UHFFFAOYSA-N 2-ethylsulfanyl-6,7-difluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=C(F)C=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 XAJZZLZZOGAEOE-UHFFFAOYSA-N 0.000 claims 1
- KDYVECDQZBNVNN-UHFFFAOYSA-N 2-ethylsulfanyl-6,7-difluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=C(F)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 KDYVECDQZBNVNN-UHFFFAOYSA-N 0.000 claims 1
- NDQQAANSMNSKGC-UHFFFAOYSA-N 2-ethylsulfanyl-6-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(F)C=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 NDQQAANSMNSKGC-UHFFFAOYSA-N 0.000 claims 1
- LABJBBGATZAEOJ-UHFFFAOYSA-N 2-ethylsulfanyl-6-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=C(F)C=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 LABJBBGATZAEOJ-UHFFFAOYSA-N 0.000 claims 1
- DVPBKUXQKWCOCX-UHFFFAOYSA-N 2-ethylsulfanyl-7-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 DVPBKUXQKWCOCX-UHFFFAOYSA-N 0.000 claims 1
- KENKFKUDCKSCJA-UHFFFAOYSA-N 2-ethylsulfanyl-7-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 KENKFKUDCKSCJA-UHFFFAOYSA-N 0.000 claims 1
- NDJCIULEZPSLRB-UHFFFAOYSA-N 2-ethylsulfanyl-8-fluoro-n-[(3-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=C(F)C=CC=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 NDJCIULEZPSLRB-UHFFFAOYSA-N 0.000 claims 1
- KDBBRFBPEGZGHV-UHFFFAOYSA-N 2-ethylsulfanyl-8-fluoro-n-[(4-fluorophenyl)methyl]-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=C(F)C=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 KDBBRFBPEGZGHV-UHFFFAOYSA-N 0.000 claims 1
- OHILXZYXWBTIAZ-UHFFFAOYSA-N 2-ethylsulfanyl-N-[(3-fluorophenyl)methyl]-5-hydroxy-4-methylquinoline-3-carboxamide Chemical compound CCSC1=NC2=CC=CC(O)=C2C(C)=C1C(=O)NCC1=CC=CC(F)=C1 OHILXZYXWBTIAZ-UHFFFAOYSA-N 0.000 claims 1
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- 239000000654 additive Substances 0.000 claims 1
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- GIIHJIRAQCRSSB-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-methyl-2-methylsulfanyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(F)C=C1 GIIHJIRAQCRSSB-UHFFFAOYSA-N 0.000 claims 1
- AUTPBQFCUQZVKU-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(C(C)(C)C)C=C1 AUTPBQFCUQZVKU-UHFFFAOYSA-N 0.000 claims 1
- ZQIVOMOWMDUEDS-UHFFFAOYSA-N n-[(5-chlorothiophen-2-yl)methyl]-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=C(Cl)S1 ZQIVOMOWMDUEDS-UHFFFAOYSA-N 0.000 claims 1
- QDWNPQYMTVSWQT-UHFFFAOYSA-N n-benzyl-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCSC1=NC2=CC(C(F)(F)F)=CC=C2C(C)=C1C(=O)NCC1=CC=CC=C1 QDWNPQYMTVSWQT-UHFFFAOYSA-N 0.000 claims 1
- PBLRPZQSTMLCET-UHFFFAOYSA-N n-butyl-2-ethylsulfanyl-4-methyl-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=C2N=C(SCC)C(C(=O)NCCCC)=C(C)C2=C1 PBLRPZQSTMLCET-UHFFFAOYSA-N 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09003597 | 2009-03-12 | ||
| EP09003597.3 | 2009-03-12 | ||
| PCT/EP2010/001509 WO2010102811A1 (de) | 2009-03-12 | 2010-03-11 | Substituierte 2-mercaptochinolin-3-carboxamide als kcnq2/3 modulatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011141188A true RU2011141188A (ru) | 2013-04-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2011141188/04A RU2011141188A (ru) | 2009-03-12 | 2010-03-11 | Замещенные 2-меркаптохинолин-3-карбоксамиды в качестве kcnq2/3 модуляторов |
Country Status (20)
| Country | Link |
|---|---|
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| EP (1) | EP2406229A1 (enExample) |
| JP (1) | JP5727946B2 (enExample) |
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| CN (1) | CN102348692A (enExample) |
| AR (1) | AR075824A1 (enExample) |
| AU (1) | AU2010223513B2 (enExample) |
| BR (1) | BRPI1008939A2 (enExample) |
| CA (1) | CA2755004A1 (enExample) |
| CL (1) | CL2011002209A1 (enExample) |
| CO (1) | CO6410292A2 (enExample) |
| EC (1) | ECSP11011348A (enExample) |
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| MX (1) | MX2011009369A (enExample) |
| NZ (1) | NZ595625A (enExample) |
| PE (1) | PE20120790A1 (enExample) |
| RU (1) | RU2011141188A (enExample) |
| TW (1) | TWI461197B (enExample) |
| WO (1) | WO2010102811A1 (enExample) |
| ZA (1) | ZA201107444B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP3178067B2 (ja) | 1991-02-26 | 2001-06-18 | ぺんてる株式会社 | スズ−ニッケル二元合金電気めっき液組成物 |
| TWI504395B (zh) * | 2009-03-10 | 2015-10-21 | Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier | |
| WO2010102778A2 (de) * | 2009-03-10 | 2010-09-16 | Grünenthal GmbH | Substituierte 3-aminoisoxazolopyridine als kcnq2/3 modulatoren |
| TW201038565A (en) | 2009-03-12 | 2010-11-01 | Gruenenthal Gmbh | Substituted 2-mercapto-3-aminopyridines as KCNQ2/3 modulators |
| TWI475020B (zh) | 2009-03-12 | 2015-03-01 | The substituted nicotine amide as a KCNQ2 / 3 modifier | |
| PE20140214A1 (es) | 2010-08-27 | 2014-02-19 | Gruenenthal Chemie | 2-oxo- y 2-tioxo-dihidroquinolina-3-carboxamidas sustituidos como moduladores kcnq2/3 |
| BR112013004562A2 (pt) | 2010-08-27 | 2016-09-06 | Gruenenthal Gmbh | 2-óxi-quinolina-3-carboxamidas substituídas como moduladores kcnq2/3 |
| AU2011297937B2 (en) | 2010-09-01 | 2015-10-01 | Grunenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
| MX2015004511A (es) | 2012-10-11 | 2015-07-06 | Grünenthal GmbH | Tratamiento y/o profilaxis de enfermedades y/o trastornos provocados por tspo. |
| CA2892652A1 (en) | 2012-11-28 | 2014-06-05 | Grunenthal Gmbh | Heteroquinoline-3-carboxamides as kcnq2/3 modulators |
| MX2015006689A (es) | 2012-11-28 | 2015-08-20 | Grünenthal GmbH | Carboxamidas especificas como moduladores de kcnq2/3. |
| US9248122B2 (en) | 2012-11-28 | 2016-02-02 | Grünenthal GmbH | Heteroquinoline-3-carboxamides as KCNQ2/3 modulators |
| BR112015017997B1 (pt) * | 2013-01-31 | 2023-03-07 | Vertex Pharmaceuticals Incorporated | Amidas de quinolina e quinoxalina como moduladores de canais de sódio, seus usos, e composição farmacêutica |
| US9139583B2 (en) | 2013-02-01 | 2015-09-22 | Acetylon Pharmaceuticals, Inc. | Selective HDAC3 inhibitors |
| US9096549B2 (en) | 2013-02-01 | 2015-08-04 | Acetylon Pharmaceuticals, Inc. | Selective HDAC3 inhibitors |
| EP2956138B1 (en) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
| ES2831625T3 (es) | 2013-02-20 | 2021-06-09 | Kala Pharmaceuticals Inc | Compuestos terapéuticos y sus usos |
| US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| CN108530458A (zh) | 2013-11-01 | 2018-09-14 | 卡拉制药公司 | 治疗化合物的结晶形式及其用途 |
| PH12015000236B1 (en) * | 2015-07-06 | 2024-01-10 | Samsung Electronics Co Ltd | Electronic device for providing a calibrated keyboard configuration |
| EP3509421A4 (en) | 2016-09-08 | 2020-05-20 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
| US10253036B2 (en) | 2016-09-08 | 2019-04-09 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| EP3509423A4 (en) | 2016-09-08 | 2020-05-13 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
| WO2018110669A1 (en) | 2016-12-15 | 2018-06-21 | Ono Pharmaceutical Co., Ltd. | Activator of trek (twik related k+ channels) channels |
| DE102018212006B3 (de) | 2018-07-18 | 2019-10-31 | Universität Greifswald | Thioether als Modulatoren von Kv7.2/Kv7.3-Kanälen |
| EP4580618A2 (en) * | 2022-08-30 | 2025-07-09 | Pannex Therapeutics Inc. | Pannexin-1 modulators and methods of treating disorders in which pannexin-1 is implicated |
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| DE2706977A1 (de) | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
| FR2532939A1 (fr) * | 1982-09-13 | 1984-03-16 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur preparation, leur application comme medicament, les compositions les renfermant et les nouveaux intermediaires obtenus |
| DE4032147A1 (de) | 1990-10-10 | 1992-04-16 | Bayer Ag | Verwendung von substituierten 2-mercaptonicotinsaeurederivaten zur bekaempfung von endoparasiten, neue substituierte 2-mercaptonicotinsaeurederivate und verfahren zu ihrer herstellung |
| EP0716077A1 (de) | 1994-12-08 | 1996-06-12 | Ciba-Geigy Ag | Aromatisch substituierte Omega-Aminoalkansäureamide und Alkansäurediamide und ihre Verwendung als Renininhibitoren |
| WO1996026925A1 (en) | 1995-03-01 | 1996-09-06 | Banyu Pharmaceutical Co., Ltd. | Arylthioacetamide derivatives |
| DE19738615A1 (de) * | 1997-09-04 | 1999-03-11 | Clariant Gmbh | Neue Lichtschutzmittel auf Basis von sterisch gehinderten Aminen |
| DE19738616A1 (de) | 1997-09-04 | 1999-03-11 | Clariant Gmbh | 4-Hydroxychinolin-3-carbonsäure-Derivate als Lichtschutzmittel |
| WO2000042026A1 (en) * | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| DE60037321D1 (de) | 1999-08-04 | 2008-01-17 | Icagen Inc | Benzanilide als öffner des kaliumkanals |
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| MXPA03007397A (es) * | 2001-02-20 | 2003-12-04 | Bristol Myers Squibb Co | Moduladores de canales de potasio kcnq y uso de los mismos en tratamiento de migrana y enfermedades mecanicamente relacionadas. |
| US6593349B2 (en) | 2001-03-19 | 2003-07-15 | Icagen, Inc. | Bisarylamines as potassium channel openers |
| WO2002081728A2 (en) | 2001-04-06 | 2002-10-17 | Smithkline Beecham Corporation | Quinoline inhibitors of hyak1 and hyak3 kinases |
| AU2003272552A1 (en) | 2002-09-17 | 2004-04-08 | Pharmacia Corporation | Aromatic liver x-receptor modulators |
| WO2004058704A2 (en) | 2002-12-23 | 2004-07-15 | Icagen, Inc. | Quinazolinones as potassium channel modulators |
| EP1449841A1 (en) | 2003-02-19 | 2004-08-25 | Bayer CropScience SA | New fungicidal compounds |
| CA2540978A1 (en) | 2003-10-08 | 2005-04-21 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters containing cycloalkyl or pyranyl groups |
| BRPI0510598A (pt) | 2004-05-04 | 2007-11-20 | Pfizer | compostos de amida de aril ou heteroaril substituìdos |
| HUE032540T2 (en) * | 2004-06-24 | 2017-09-28 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| JP2008519814A (ja) | 2004-11-12 | 2008-06-12 | ガラパゴス・ナムローゼ・フェンノートシャップ | プロテインキナーゼ酵素の活性部位と結合する窒素複素環式芳香族化合物 |
| US7812020B2 (en) | 2005-03-03 | 2010-10-12 | H. Lundbeck A/S | Substituted pyridine derivatives |
| DE102005038947A1 (de) | 2005-05-18 | 2006-11-30 | Grünenthal GmbH | Substituierte Benzo[d]isoxazol-3-yl-amin-Verbindungen und deren Verwendung in Arzneimitteln |
| ES2325558T3 (es) | 2005-07-20 | 2009-09-08 | Eli Lilly And Company | Derivados de piridina como inhibidores de dipeptidilpeptidasa. |
| WO2007030582A2 (en) | 2005-09-09 | 2007-03-15 | Bristol-Myers Squibb Company | Acyclic ikur inhibitors |
| WO2007057447A1 (en) | 2005-11-18 | 2007-05-24 | Neurosearch A/S | Novel quinazoline derivatives and their medical use |
| EP2057133B1 (en) | 2006-07-20 | 2014-08-20 | Amgen Inc. | Di-amino-substituted heterocyclic compounds and methods of use |
| DE602007004638D1 (de) | 2006-07-20 | 2010-03-18 | Amgen Inc | Benzoädüisoxazol-derivate als c-kit-tyrosinkinase-hemmer zur behandlung von erkrankungen im zusammenhang mit der überproduktion von histamin |
| US20100022589A1 (en) | 2006-07-27 | 2010-01-28 | Mccoull William | Pyridine-3-carboxamide compounds and their use for inhibiting 11-beta-hydroxysteroid dehydrogenase |
| DE102006049452A1 (de) | 2006-10-17 | 2008-05-08 | Grünenthal GmbH | Substituierte Tetrahydropyrolopiperazin-Verbindungen und deren Verwendung in Arzneimitteln |
| WO2008066900A1 (en) * | 2006-11-28 | 2008-06-05 | Valeant Pharmaceuticals International | 1,4 diamino bicyclic retigabine analogues as potassium channel modulators |
| US8563566B2 (en) | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
| AU2008285795A1 (en) | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as TAAR1 ligands |
| EP2215065B1 (en) | 2007-10-19 | 2012-07-11 | Boehringer Ingelheim International GmbH | Ccr10 antagonists |
| WO2010102778A2 (de) * | 2009-03-10 | 2010-09-16 | Grünenthal GmbH | Substituierte 3-aminoisoxazolopyridine als kcnq2/3 modulatoren |
| TWI504395B (zh) * | 2009-03-10 | 2015-10-21 | Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier | |
| TW201038565A (en) * | 2009-03-12 | 2010-11-01 | Gruenenthal Gmbh | Substituted 2-mercapto-3-aminopyridines as KCNQ2/3 modulators |
| TWI475020B (zh) * | 2009-03-12 | 2015-03-01 | The substituted nicotine amide as a KCNQ2 / 3 modifier |
-
2010
- 2010-02-24 TW TW099105238A patent/TWI461197B/zh not_active IP Right Cessation
- 2010-03-10 US US12/720,864 patent/US20100234372A1/en not_active Abandoned
- 2010-03-11 NZ NZ595625A patent/NZ595625A/xx not_active IP Right Cessation
- 2010-03-11 RU RU2011141188/04A patent/RU2011141188A/ru not_active Application Discontinuation
- 2010-03-11 PE PE2011001567A patent/PE20120790A1/es not_active Application Discontinuation
- 2010-03-11 BR BRPI1008939A patent/BRPI1008939A2/pt not_active IP Right Cessation
- 2010-03-11 KR KR1020117023788A patent/KR20110132590A/ko not_active Withdrawn
- 2010-03-11 MX MX2011009369A patent/MX2011009369A/es active IP Right Grant
- 2010-03-11 EP EP10708726A patent/EP2406229A1/de not_active Withdrawn
- 2010-03-11 JP JP2011553352A patent/JP5727946B2/ja not_active Expired - Fee Related
- 2010-03-11 CA CA2755004A patent/CA2755004A1/en not_active Abandoned
- 2010-03-11 WO PCT/EP2010/001509 patent/WO2010102811A1/de not_active Ceased
- 2010-03-11 CN CN2010800112967A patent/CN102348692A/zh active Pending
- 2010-03-11 AU AU2010223513A patent/AU2010223513B2/en not_active Ceased
- 2010-03-12 AR ARP100100777A patent/AR075824A1/es not_active Application Discontinuation
-
2011
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- 2011-09-04 IL IL214945A patent/IL214945A0/en unknown
- 2011-09-08 CL CL2011002209A patent/CL2011002209A1/es unknown
- 2011-09-23 EC EC2011011348A patent/ECSP11011348A/es unknown
- 2011-10-11 ZA ZA2011/07444A patent/ZA201107444B/en unknown
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2012
- 2012-06-15 US US13/523,955 patent/US8399673B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI1008939A2 (pt) | 2016-03-15 |
| NZ595625A (en) | 2012-10-26 |
| ECSP11011348A (es) | 2011-10-31 |
| AU2010223513B2 (en) | 2014-12-04 |
| WO2010102811A1 (de) | 2010-09-16 |
| JP2012520249A (ja) | 2012-09-06 |
| JP5727946B2 (ja) | 2015-06-03 |
| CO6410292A2 (es) | 2012-03-30 |
| MX2011009369A (es) | 2011-09-27 |
| AU2010223513A1 (en) | 2011-11-03 |
| IL214945A0 (en) | 2011-11-30 |
| PE20120790A1 (es) | 2012-07-08 |
| KR20110132590A (ko) | 2011-12-08 |
| ZA201107444B (en) | 2012-06-27 |
| US8399673B2 (en) | 2013-03-19 |
| CL2011002209A1 (es) | 2012-02-10 |
| US20120252841A1 (en) | 2012-10-04 |
| TW201034670A (en) | 2010-10-01 |
| EP2406229A1 (de) | 2012-01-18 |
| CN102348692A (zh) | 2012-02-08 |
| AR075824A1 (es) | 2011-04-27 |
| US20100234372A1 (en) | 2010-09-16 |
| CA2755004A1 (en) | 2010-09-16 |
| TWI461197B (zh) | 2014-11-21 |
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