HRP20151260T1 - Supstituirani nikotinamidi kao modulatori kcnq2/3 - Google Patents
Supstituirani nikotinamidi kao modulatori kcnq2/3 Download PDFInfo
- Publication number
- HRP20151260T1 HRP20151260T1 HRP20151260TT HRP20151260T HRP20151260T1 HR P20151260 T1 HRP20151260 T1 HR P20151260T1 HR P20151260T T HRP20151260T T HR P20151260TT HR P20151260 T HRP20151260 T HR P20151260T HR P20151260 T1 HRP20151260 T1 HR P20151260T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- pyridine
- carboxylic acid
- alkyl
- fluorophenyl
- Prior art date
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- 235000005152 nicotinamide Nutrition 0.000 title claims 15
- 150000005480 nicotinamides Chemical class 0.000 title claims 15
- 150000001408 amides Chemical class 0.000 claims 59
- -1 C(=O)-OH Chemical group 0.000 claims 52
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 42
- 229920006395 saturated elastomer Polymers 0.000 claims 30
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 26
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- 239000011664 nicotinic acid Substances 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([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
- 125000003396 thiol group Chemical group [H]S* 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 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000011570 nicotinamide Substances 0.000 claims 3
- 229960003966 nicotinamide Drugs 0.000 claims 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000014094 Dystonic disease Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 229910003827 NRaRb Inorganic materials 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000010118 dystonia Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- QDLFKVRFYGCTBU-UHFFFAOYSA-N 1-(1-bicyclo[2.2.1]heptanylmethyl)-2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-2H-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN(CC23CCC(CC2)C3)C1SCCC(F)(F)C1=CC=C(F)C=C1 QDLFKVRFYGCTBU-UHFFFAOYSA-N 0.000 claims 1
- YZJRKFROMCUSQH-UHFFFAOYSA-N 1-(2-bicyclo[2.2.1]heptanylmethyl)-2-(3-naphthalen-1-ylpropylsulfanyl)-2H-pyridine-3-carboxylic acid Chemical compound C1=CC=C2C(CCCSC3N(CC4C5CCC(C5)C4)C=CC=C3C(=O)O)=CC=CC2=C1 YZJRKFROMCUSQH-UHFFFAOYSA-N 0.000 claims 1
- QRUCLKSRMDFRMF-UHFFFAOYSA-N 1-(2-bicyclo[2.2.1]heptanylmethyl)-2-[3-(2,4,5-trifluorophenyl)propylsulfanyl]-2H-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN(CC2C3CCC(C3)C2)C1SCCCC1=CC(F)=C(F)C=C1F QRUCLKSRMDFRMF-UHFFFAOYSA-N 0.000 claims 1
- XZFVEHGEAQPQIJ-UHFFFAOYSA-N 1-(2-bicyclo[2.2.1]heptanylmethyl)-2-[3-(3,5-difluorophenyl)propylsulfanyl]-2H-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN(CC2C3CCC(C3)C2)C1SCCCC1=CC(F)=CC(F)=C1 XZFVEHGEAQPQIJ-UHFFFAOYSA-N 0.000 claims 1
- QAXWUTPVQAQLPX-UHFFFAOYSA-N 1-(2-bicyclo[2.2.1]heptanylmethyl)-2-[3-(3-hydroxyphenyl)propylsulfanyl]-2H-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN(CC2C3CCC(C3)C2)C1SCCCC1=CC=CC(O)=C1 QAXWUTPVQAQLPX-UHFFFAOYSA-N 0.000 claims 1
- BZALIJBIVZBWIJ-UHFFFAOYSA-N 1-(thiophen-2-ylmethyl)-2-[4-[3-(trifluoromethyl)phenyl]butan-2-ylsulfanyl]-2H-pyridine-3-carboxylic acid Chemical compound C=1C=CSC=1CN1C=CC=C(C(O)=O)C1SC(C)CCC1=CC=CC(C(F)(F)F)=C1 BZALIJBIVZBWIJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- OZFLOQVSDDYYBS-UHFFFAOYSA-N 2-(2-benzylcyclohexyl)sulfanyl-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SC2C(CCCC2)CC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 OZFLOQVSDDYYBS-UHFFFAOYSA-N 0.000 claims 1
- DOSMXASCZCOLQY-UHFFFAOYSA-N 2-(2-benzylcyclopentyl)sulfanyl-n-(3,3-dimethylbutyl)pyridine-3-carboxamide Chemical compound CC(C)(C)CCNC(=O)C1=CC=CN=C1SC1C(CC=2C=CC=CC=2)CCC1 DOSMXASCZCOLQY-UHFFFAOYSA-N 0.000 claims 1
- XOOMRGSTJYKNLN-UHFFFAOYSA-N 2-(3-cyclohexylpropylsulfanyl)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SCCCC2CCCCC2)C=1C(=O)NCC1=CC=CS1 XOOMRGSTJYKNLN-UHFFFAOYSA-N 0.000 claims 1
- SBWZUJFQKGGZFI-UHFFFAOYSA-N 2-(3-naphthalen-2-ylpropylsulfanyl)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SCCCC=2C=C3C=CC=CC3=CC=2)C=1C(=O)NCC1=CC=CS1 SBWZUJFQKGGZFI-UHFFFAOYSA-N 0.000 claims 1
- LGXVQKJZNNGRNU-UHFFFAOYSA-N 2-(3-phenylcyclohexyl)sulfanyl-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SC2CC(CCC2)C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 LGXVQKJZNNGRNU-UHFFFAOYSA-N 0.000 claims 1
- UXCQYSRNWITPGM-UHFFFAOYSA-N 2-(3-pyridin-4-ylpropylsulfanyl)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SCCCC=2C=CN=CC=2)C=1C(=O)NCC1=CC=CS1 UXCQYSRNWITPGM-UHFFFAOYSA-N 0.000 claims 1
- DLRFRKOIZQCEQZ-UHFFFAOYSA-N 2-(4-phenylbutan-2-ylsulfanyl)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NCC=2SC=CC=2)C=1SC(C)CCC1=CC=CC=C1 DLRFRKOIZQCEQZ-UHFFFAOYSA-N 0.000 claims 1
- MMXFCWPYYYAZQJ-UHFFFAOYSA-N 2-(4-phenylbutyl)-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(CCCCC=2C=CC=CC=2)C=1C(=O)NCC1=CC=CS1 MMXFCWPYYYAZQJ-UHFFFAOYSA-N 0.000 claims 1
- BKDSHNYLRDRGNP-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-1-(2-hydroxyethyl)-2h-pyridine-3-carboxylic acid Chemical compound OCCN1C=CC=C(C(O)=O)C1SCCC(F)(F)C1=CC=C(F)C=C1 BKDSHNYLRDRGNP-UHFFFAOYSA-N 0.000 claims 1
- CSFXZDCCOQAELZ-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-1-(oxan-2-ylmethyl)-2H-pyridine-3-carboxylic acid Chemical compound FC(CCSC1N(C=CC=C1C(=O)O)CC1OCCCC1)(C1=CC=C(C=C1)F)F CSFXZDCCOQAELZ-UHFFFAOYSA-N 0.000 claims 1
- VAUKUHRGEVTFJX-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-1-hexyl-2H-pyridine-3-carboxylic acid Chemical compound FC(CCSC1N(C=CC=C1C(=O)O)CCCCCC)(C1=CC=C(C=C1)F)F VAUKUHRGEVTFJX-UHFFFAOYSA-N 0.000 claims 1
- BHFMEVYLHXIMOU-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(2-methoxybutyl)pyridine-3-carboxamide Chemical compound CCC(OC)CNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 BHFMEVYLHXIMOU-UHFFFAOYSA-N 0.000 claims 1
- IATKYFGBPIIQQZ-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(2-methoxypropyl)pyridine-3-carboxamide Chemical compound COC(C)CNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 IATKYFGBPIIQQZ-UHFFFAOYSA-N 0.000 claims 1
- FUGIGPLHOQTBMH-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(3-methoxybutyl)pyridine-3-carboxamide Chemical compound COC(C)CCNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 FUGIGPLHOQTBMH-UHFFFAOYSA-N 0.000 claims 1
- IAMKWWDFWPIRNN-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(furan-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(F)(F)CCSC1=NC=CC=C1C(=O)NCC1=CC=CO1 IAMKWWDFWPIRNN-UHFFFAOYSA-N 0.000 claims 1
- JKJRLMHRCDZQIV-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(oxan-3-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(F)(F)CCSC1=NC=CC=C1C(=O)NCC1COCCC1 JKJRLMHRCDZQIV-UHFFFAOYSA-N 0.000 claims 1
- NVOUNEVXWHVJPP-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(oxan-4-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(F)(F)CCSC1=NC=CC=C1C(=O)NCC1CCOCC1 NVOUNEVXWHVJPP-UHFFFAOYSA-N 0.000 claims 1
- WIVKZDSNOVRNIW-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-(thiophen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(F)(F)CCSC1=NC=CC=C1C(=O)NCC1=CC=CS1 WIVKZDSNOVRNIW-UHFFFAOYSA-N 0.000 claims 1
- JOCCJFVJKRTEQT-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-[(3,5-dimethylphenyl)methyl]pyridine-3-carboxamide Chemical compound CC1=CC(C)=CC(CNC(=O)C=2C(=NC=CC=2)SCCC(F)(F)C=2C=CC(F)=CC=2)=C1 JOCCJFVJKRTEQT-UHFFFAOYSA-N 0.000 claims 1
- OCVOOBBATOCIOS-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-[(4-fluorophenyl)methyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 OCVOOBBATOCIOS-UHFFFAOYSA-N 0.000 claims 1
- NSDTXWQHAIHMRK-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-[(5-methylfuran-2-yl)methyl]pyridine-3-carboxamide Chemical compound O1C(C)=CC=C1CNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 NSDTXWQHAIHMRK-UHFFFAOYSA-N 0.000 claims 1
- JTXVUGJYRIXHIO-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-[2-(dimethylamino)ethyl]pyridine-3-carboxamide Chemical compound CN(C)CCNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 JTXVUGJYRIXHIO-UHFFFAOYSA-N 0.000 claims 1
- XKSRLXZPUYJJBP-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-pentylpyridine-3-carboxamide Chemical compound CCCCCNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 XKSRLXZPUYJJBP-UHFFFAOYSA-N 0.000 claims 1
- ZBAUKPHZXRMRAZ-UHFFFAOYSA-N 2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanyl-n-propylpyridine-3-carboxamide Chemical compound CCCNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=C(F)C=C1 ZBAUKPHZXRMRAZ-UHFFFAOYSA-N 0.000 claims 1
- ISFDPGNTXGFBRF-UHFFFAOYSA-N 2-[3,3-difluoro-3-[3-(trifluoromethyl)phenyl]propyl]sulfanyl-1-(3,3-dimethylbutyl)-2H-pyridine-3-carboxylic acid Chemical compound CC(C)(C)CCN1C=CC=C(C(O)=O)C1SCCC(F)(F)C1=CC=CC(C(F)(F)F)=C1 ISFDPGNTXGFBRF-UHFFFAOYSA-N 0.000 claims 1
- QVQCVIYBUWVRCO-UHFFFAOYSA-N 2-[3,3-difluoro-3-[3-(trifluoromethyl)phenyl]propyl]sulfanyl-n-[(4-fluorophenyl)methyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CN=C1SCCC(F)(F)C1=CC=CC(C(F)(F)F)=C1 QVQCVIYBUWVRCO-UHFFFAOYSA-N 0.000 claims 1
- NZWWPVVBZIDGFE-UHFFFAOYSA-N 2-[3-(3,4-difluorophenyl)-3,3-difluoropropyl]sulfanyl-1-(3-methylbutyl)-2H-pyridine-3-carboxylic acid Chemical compound CC(C)CCN1C=CC=C(C(O)=O)C1SCCC(F)(F)C1=CC=C(F)C(F)=C1 NZWWPVVBZIDGFE-UHFFFAOYSA-N 0.000 claims 1
- SNWMIHLQVWRYKX-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-1-(furan-2-ylmethyl)-2h-pyridine-3-carboxylic acid Chemical compound C=1C=C(F)C=CC=1CCCSC1C(C(=O)O)=CC=CN1CC1=CC=CO1 SNWMIHLQVWRYKX-UHFFFAOYSA-N 0.000 claims 1
- LLVPERZBAAGSLP-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1CC2=CC=CC=C2CC1 LLVPERZBAAGSLP-UHFFFAOYSA-N 0.000 claims 1
- JLNYPNBIJGMCOT-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(1,3,4-oxadiazol-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=NN=CO1 JLNYPNBIJGMCOT-UHFFFAOYSA-N 0.000 claims 1
- BUAOAOFUASXMFK-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(1,3-oxazol-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=NC=CO1 BUAOAOFUASXMFK-UHFFFAOYSA-N 0.000 claims 1
- GQYAZNSTPNLNBI-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(1,3-thiazol-2-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=NC=CS1 GQYAZNSTPNLNBI-UHFFFAOYSA-N 0.000 claims 1
- IZFHGALJLCMIRR-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(1,3-thiazol-5-ylmethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CN=CS1 IZFHGALJLCMIRR-UHFFFAOYSA-N 0.000 claims 1
- PZLJVKUTGISRPR-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(2-phenylethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCCC1=CC=CC=C1 PZLJVKUTGISRPR-UHFFFAOYSA-N 0.000 claims 1
- SKDAWKVKGWUANQ-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(2-pyridin-2-ylethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCCC1=CC=CC=N1 SKDAWKVKGWUANQ-UHFFFAOYSA-N 0.000 claims 1
- GXHGAZIUNYESCA-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(2-pyridin-3-ylethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCCC1=CC=CN=C1 GXHGAZIUNYESCA-UHFFFAOYSA-N 0.000 claims 1
- KASXTMYTOWJZQI-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(2-pyridin-4-ylethyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCCC1=CC=NC=C1 KASXTMYTOWJZQI-UHFFFAOYSA-N 0.000 claims 1
- DTGJLGFTPUOQAV-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(3-methyl-3-phenylbutyl)pyridine-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)(C)CCNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 DTGJLGFTPUOQAV-UHFFFAOYSA-N 0.000 claims 1
- GQTWZPAVZOYCDP-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(3-methylbutyl)pyridine-3-carboxamide Chemical compound CC(C)CCNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 GQTWZPAVZOYCDP-UHFFFAOYSA-N 0.000 claims 1
- KADJMOZZDCVLOH-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propylsulfanyl]-n-(3-pyrazol-1-ylpropyl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCCCN1N=CC=C1 KADJMOZZDCVLOH-UHFFFAOYSA-N 0.000 claims 1
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- VPDIHEKACZBIBO-UHFFFAOYSA-N n-(7-bicyclo[2.2.1]heptanylmethyl)-2-[4-(4-fluorophenyl)butan-2-ylsulfanyl]pyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NCC2C3CCC2CC3)C=1SC(C)CCC1=CC=C(F)C=C1 VPDIHEKACZBIBO-UHFFFAOYSA-N 0.000 claims 1
- AWQMAARFIOSOFY-UHFFFAOYSA-N n-(cycloheptylmethyl)-2-[3,3-difluoro-3-(4-fluorophenyl)propyl]sulfanylpyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(F)(F)CCSC1=NC=CC=C1C(=O)NCC1CCCCCC1 AWQMAARFIOSOFY-UHFFFAOYSA-N 0.000 claims 1
- QXVGWQFCHTWRGF-UHFFFAOYSA-N n-(cycloheptylmethyl)-2-[3-(4-fluorophenyl)sulfanylpropyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1SCCCC1=NC=CC=C1C(=O)NCC1CCCCCC1 QXVGWQFCHTWRGF-UHFFFAOYSA-N 0.000 claims 1
- IZIGTQMRBXPYHB-UHFFFAOYSA-N n-(cycloheptylmethyl)-2-[3-[3-(trifluoromethyl)phenyl]sulfonylpropyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)CCCC=2C(=CC=CN=2)C(=O)NCC2CCCCCC2)=C1 IZIGTQMRBXPYHB-UHFFFAOYSA-N 0.000 claims 1
- OLAKGPRDWQPDPH-UHFFFAOYSA-N n-(cycloheptylmethyl)-2-[4-[3-(trifluoromethyl)phenyl]butyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CCCCC=2C(=CC=CN=2)C(=O)NCC2CCCCCC2)=C1 OLAKGPRDWQPDPH-UHFFFAOYSA-N 0.000 claims 1
- GZVJVIFIZAVVTM-UHFFFAOYSA-N n-(cyclohexylmethyl)-2-(4-phenylbutyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(CCCCC=2C=CC=CC=2)C=1C(=O)NCC1CCCCC1 GZVJVIFIZAVVTM-UHFFFAOYSA-N 0.000 claims 1
- JKJQJZVCIRQFGL-UHFFFAOYSA-N n-(cyclooctylmethyl)-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1CCCCCCC1 JKJQJZVCIRQFGL-UHFFFAOYSA-N 0.000 claims 1
- ZHMBOMIDJJLTEM-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-(3-thiophen-2-ylpropylsulfanyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SCCCC=2SC=CC=2)C=1C(=O)NCC1=CC=CS1 ZHMBOMIDJJLTEM-UHFFFAOYSA-N 0.000 claims 1
- HWDBPBMJNPOKNU-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-(3-thiophen-3-ylpropylsulfanyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(SCCCC2=CSC=C2)C=1C(=O)NCC1=CC=CS1 HWDBPBMJNPOKNU-UHFFFAOYSA-N 0.000 claims 1
- JKQYGJCTDCDGBF-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-[3-[3-(trifluoromethyl)phenyl]propylsulfanyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CCCSC=2C(=CC=CN=2)C(=O)NCC=2SC=CC=2)=C1 JKQYGJCTDCDGBF-UHFFFAOYSA-N 0.000 claims 1
- FJZAZDHVKPQPKB-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-[3-[3-(trifluoromethyl)phenyl]sulfanylpropyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(SCCCC=2C(=CC=CN=2)C(=O)NCC=2SC=CC=2)=C1 FJZAZDHVKPQPKB-UHFFFAOYSA-N 0.000 claims 1
- GKAAVFRIQLILBB-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-[3-[3-(trifluoromethyl)phenyl]sulfonylpropyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)CCCC=2C(=CC=CN=2)C(=O)NCC=2SC=CC=2)=C1 GKAAVFRIQLILBB-UHFFFAOYSA-N 0.000 claims 1
- USTLLFHAQPZDAI-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-[4-[3-(trifluoromethyl)phenyl]butyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CCCCC=2C(=CC=CN=2)C(=O)NCC=2SC=CC=2)=C1 USTLLFHAQPZDAI-UHFFFAOYSA-N 0.000 claims 1
- PSSNKJIIFCFUGV-UHFFFAOYSA-N n-[(2,2-dimethylcyclopropyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound CC1(C)CC1CNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 PSSNKJIIFCFUGV-UHFFFAOYSA-N 0.000 claims 1
- CNJAWHVHHSGGEC-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=CC=C1F CNJAWHVHHSGGEC-UHFFFAOYSA-N 0.000 claims 1
- UJXMJLRUWWBMED-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=C(F)C(F)=C1 UJXMJLRUWWBMED-UHFFFAOYSA-N 0.000 claims 1
- UUIQUAWWNCJWAC-UHFFFAOYSA-N n-[(3,5-difluorophenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC(F)=CC(F)=C1 UUIQUAWWNCJWAC-UHFFFAOYSA-N 0.000 claims 1
- PUPKYBBNDUFJLR-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=CC(F)=C1 PUPKYBBNDUFJLR-UHFFFAOYSA-N 0.000 claims 1
- DNIAXCOUQWVDLP-UHFFFAOYSA-N n-[(4-fluoro-2-hydroxyphenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound OC1=CC(F)=CC=C1CNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 DNIAXCOUQWVDLP-UHFFFAOYSA-N 0.000 claims 1
- OANOZTVEMATZHP-UHFFFAOYSA-N n-[(4-fluoro-2-methoxyphenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound COC1=CC(F)=CC=C1CNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 OANOZTVEMATZHP-UHFFFAOYSA-N 0.000 claims 1
- DJKFNYBLDUEQBF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=C(F)C=C1 DJKFNYBLDUEQBF-UHFFFAOYSA-N 0.000 claims 1
- SKZIWSTXTNXQTI-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[3-[3-(trifluoromethyl)phenyl]propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CN=C1SCCCC1=CC=CC(C(F)(F)F)=C1 SKZIWSTXTNXQTI-UHFFFAOYSA-N 0.000 claims 1
- NTWQNSPCWHCFTR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-[4-[3-(trifluoromethyl)phenyl]butan-2-ylsulfanyl]pyridine-3-carboxamide Chemical compound N=1C=CC=C(C(=O)NCC=2C=CC(F)=CC=2)C=1SC(C)CCC1=CC=CC(C(F)(F)F)=C1 NTWQNSPCWHCFTR-UHFFFAOYSA-N 0.000 claims 1
- BZCVSOOVCHANQN-UHFFFAOYSA-N n-[(5-chlorothiophen-2-yl)methyl]-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=C(Cl)S1 BZCVSOOVCHANQN-UHFFFAOYSA-N 0.000 claims 1
- PIJBFCMMWLHHTP-UHFFFAOYSA-N n-benzyl-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCCSC1=NC=CC=C1C(=O)NCC1=CC=CC=C1 PIJBFCMMWLHHTP-UHFFFAOYSA-N 0.000 claims 1
- BIDAZDNFQYNSDR-UHFFFAOYSA-N n-butyl-2-[3-(4-fluorophenyl)propylsulfanyl]pyridine-3-carboxamide Chemical compound CCCCNC(=O)C1=CC=CN=C1SCCCC1=CC=C(F)C=C1 BIDAZDNFQYNSDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Claims (14)
1. Supstituirani nikotinamidi s općom formulom (1),
[image]
naznačeni time da
A1 označava CR10R11 ili S;
A2 označava CR12R13, C(=O), O, S, S(=O) ili S(=O)2;
R1 označava C1-10-alkil ili C2-10-heteroalkil, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran; C3-10-cikloalkil ili heterociklil, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran, aril ili heteroaril, svaki nesupstituiran ili jednostruko- ili polisupstituiran; C3-10-cikloalkil ili heterociklil premošten preko C1-8-alkila ili C2-8-heteroalkila, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran, gdje alkilni ili heteroalkilni lanac može svaki biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, jednostruko- ili polisupstituiran; ili aril ili heteroaril premošten preko C1-8-alkila ili C2-8-heteroalkila, svaki nesupstituiran ili jednostruko- ili polisupstituiran, gdje alkilni ili heteroalkilni lanac može svaki biti razgranat ili nerazgranat, zasićen ili nezasićen, nesupstituiran, jednostruko- ili polisupstituiran;
R2, R3 i R4 svaki označava, neovisno jedan od drugoga, H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; SH; SCF3; metil; CH2-metil; CH2-OH; C2-6-alkil; O-C1-6-alkil, S-C1-6-alkil, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran; C3-7-cikloalkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran; NRaRb, gdje Ra i Rb, svaki označava, neovisno jedan od drugoga, H ili C1-4-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran, ili Ra i Rb zajedno s atomom dušika koji iste spaja tvore heterociklil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran;
R5, R6, R7, R8, R10, R11, R12 i R13 svaki označava, neovisno jedan od drugoga, H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; SH; SCF3; C1-10-alkil, C2-10-heteroalkil, O-C1-10-alkil ili S-C1-10-alkil, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran; C3-10-cikloalkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran;
pod uvjetom da A2 ne može predstavljati S, S(=O) ili S(=O)2 ako R5, R6, R7 i R8 svaki označava H, i A1 označava S;
ili R5 i R6 ili R7 i R8 ili R10 i R11 ili R12 i R13 ili R5 i R11 ili R5 i R13 ili R7 i R13 ili R7 i R11 ili R11 i R13 imaju C3-8-cikloalkil ili heterociklil s tri do osam članova u prstenu, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran zajedno s atomom ili atomima ugljika koji ih povezuju; gdje relevantni preostali supstituenti R5, R6, R7, R8, R10, R11, R12 i R13 imaju gore navedeno značenje;
ili R5 i R7 tvore C3-8-cikloalkil, zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran zajedno s atomom ili atomima ugljika koji ih povezuju; ili heterociklil s tri do osam članova u prstenu, nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran; gdje relevantni preostali supstituenti R6, R8, R10, R11, R12 i R13 imaju gore navedeno značenje;
R9 označava C3-10-cikloalkil ili heteroalkil, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran; aril ili heteroaril, svaki nesupstituiran ili jednostruko- ili polisupstituiran; ili označava CRcRd, gdje Rc i Rd svaki označava, neovisno jedan od drugoga, C1-4-alkil, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran;
pod uvjetom da se vezanje heteroarila ili heterociklila ostvaruje preko ugljikovoga atoma u heteroarilu ili heterociklilu gdje A2 označava O ili S, i R9 označavaju heterociklil, zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran; ili heteroaril, nesupstituiran ili jednostruko- ili polisupstituiran;
pri čemu "alkil supstituiran", "heteroalkil supstituiran", "heterociklil supstituiran" i "cikloalkil supstituiran" označava supstituciju jednog ili više vodikovih atoma, svaki neovisno jedan od drugog, s F; Cl; Br; I; NO2; CF3; CN; =O; C1-8-alkilom; C2-8-heteroalkilom; arilom; heteroarilom, C3-10-cikloalkilom; heterociklilom; arilom, heteroarilom, C3-10-cikloalkilom ili heterociklilom premoštenim preko C1-8-alkila ili C2-8-heteroalkila; CHO; C(=O)C1-8-alkilom; C(=O)arilom; C(=O)heteroarilom; CO2H; C(=O)O-C1-8-alkilom; C(=O)O=arilom; C(=O)O-heteroarilom; CONH2; C(=O)NH-C1-8-alkilom; C(=O)N(C1-8-alkil)2; C(=O)NH-arilom, C(=O)N(aril)2; C(=O)NH-heteroarilom; C(=O)N(heteroaril)2; C(=O)N(C1-8-alkil)(aril); C(=O)N(C1-8-alkil)(heteroaril); C(=O)N(heteroaril)(aril); OH; O-C1-8-alkilom; OCF3; O-(C1-8-alkil)-OH; O-(C1-8-alkil)-O-C1-8-alkilom; O-benzilom; O-arilom; O-heteroarilom; O-C(=O)C1-8-alkilom; O-C(=O)arilom; O-C(=O)heteroarilom; NH2; NH-C1-8-alkilom; N(C1-8-alkil)2; NH-C(=O)C1-8-alkilom; N(C1-8-alkil)-C(=O)C1-8-alkilom; N(C(=O)C1-8-alkil2; NH-C(=O)-arilom; NH-C(=O)=heteroarilom; SH; S-C1-8-alkilom; SCF3; S-benzilom; S-arilom; S-heteroarilom; S(=O)2C1-8-alkilom; S(=O)2arilom; S(=O)2heteroarilom; S(=O)2OH; S(=O)2O-C1-8-alkilom; S(=O)2O-arilom; S(=O)2O-heteroarilom; S(=O)2-NH-C1-8-alkilom; S(=O)2-NH-arilom; i S(=O)2-NH-C1-8-heteroarilom;
pri čemu "aril supstituiran" i "heteroaril supstituiran" označava supstituciju jednog ili više vodikovih atoma, svaki neovisno jedan od drugog, s F; Cl; Br; I; NO2; CF3; CN; C1-8-alkilom; C2-8-heteroalkilom; arilom; heteroarilom; C3-10-cikloalkilom; heterociklilom; arilom, heteroarilom, C3-10-cikloalkilom ili heterociklilom premoštenim preko C1-8-alkila ili C2-8-heteroalkila; CHO; C(=O)C1-8-alkilom; C(=O)arilom; C(=O)heteroarilom; C(=O)O-C1-8-alkilom; C(=O)O=arilom; C(=O)O-heteroarilom; CONH2; C(=O)NH-C1-8-alkilom; C(=O)N(C1-8-alkil)2; C(=O)NH-arilom, C(=O)N(aril)2; C(=O)NH-heteroarilom; C(=O)N(heteroaril)2; C(=O)N(C1-8-alkil)(aril); C(=O)N(C1-8-alkil)(heteroaril); C(=O)N(heteroaril)(aril); OH; O-C1-8-alkilom; OCF3; O-(C1-8-alkil)-OH; O-(C1-8-alkil)-O-C1-8-alkilom; O-benzilom; O-arilom; O-heteroarilom; O-C(=O)C1-8-alkilom; O-C(=O)arilom; O-C(=O)heteroarilom; NH2; NH-C1-8-alkilom; N(C1-8-alkil)2; NH-C(=O)C1-8-alkilom; N(C1-8-alkil)-C(=O)C1-8-alkilom; N(C(=O)C1-8-alkil2; NH-C(=O)-arilom; NH-C(=O)=heteroarilom; SH; S-C1-8-alkilom; SCF3; S-benzilom; S-arilom; S-heteroarilom; S(=O)2C1-8-alkilom; S(=O)2arilom; S(=O)2heteroarilom; S(=O)2OH; S(=O)2O-C1-8-alkilom; S(=O)2O-arilom; S(=O)2O-heteroarilom; S(=O)2-NH-C1-8-alkilom; S(=O)2-NH-arilom; i S(=O)2-NH-C1-8-heteroarilom;
u obliku slobodnih spojeva ili soli fiziološki kompatibilnih kiselina ili baza.
2. Supstituirani nikotinamidi prema zahtjevu 1, naznačeni time da
A1 označava S; i
A2 označava CR12R13, O, S ili S(=O)2.
3. Supstituirani nikotinamidi prema zahtjevu 1 ili 2, naznačeni time da
R1 označava dio strukture (T1)
[image]
pri čemu
R14a i R14b, svaki neovisno jedan od drugog, označavaju H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; NH2; C1-4-alkil, O-C1-4-alkil, NH-C1-4-alkil, N(C1-4-alkil)2, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki odabran međusobno neovisno iz skupine koja predstavlja i koja sadrži F, Cl, Br, I, O-C1-4-alkil, OH i OCF3; C3-10-cikloalkil ili heterociklil, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, C1-4-alkil, OH, =O, O-C1-4-alkil, OCF3, NH2, NH-C1-4-alkil i N(C1-4-alkil)2;
m označava 0, 1, 2 ili 3;
Y označava O ili NR15,
gdje R15 označava H; C1-4-alkil označava zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, C1-4-alkil, OH, O-C1-4-alkil, OCF3, NH2, NH-C1-4-alkil i N(C1-4-alkil)2; ili označava C3-10-cikloalkil, zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, C1-4-alkil, OH, O-C1-4-alkil, OCF3, NH2, NH-C1-4-alkil i N(C1-4-alkil)2;
n označava 0 ili 1,
B označava C1-8-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, =O, O-C1-4-alkil, OCF3, C(=O)-OH, CF3, NH2, NH(C1-4-alkil), N(C1-4-alkil)2, SH, S-C1-4-alkil, SCF3 i S(=O)2OH; C3-10-cikloalkil ili heterociklil, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-8-alkil, OCF3, C1-8-alkil, C(=O)-OH, CF3, NH2, NH(C1-8-alkil), N(C1-8-alkil)2, SH, S-C1-8-alkil, SCF3, S(=O)2OH, benzil, fenil, piridil i tienil, gdje benzil, fenil, piridin, tienil, mogu svaki biti nesupstituirani ili jednostruko- ili polisupstituirani s jednim ili više supstituenata, koji su svaki odabrani neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-8-alkil, OCF3, C1-8-alkil, C(=O)-OH, CF3, NH2, NH(C1-8-alkil), N(C1-8-alkil)2, SH, S-C1-8-alkil, SCF3 i S(=O)2OH; aril ili heteroaril, svaki nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, koji su svaki odabrani neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-8-alkil, OCF3, C1-8-alkil, C(=O)-OH, CF3, NH2, NH(C1-8-alkil), N(C1-8-alkil)2, SH, S-C1-8-alkil, SCF3 i S(=O)2OH, benzil, fenil, piridil i tienil, gdje benzil, fenil, piridil, tienil mogu svaki biti nesupstituirani ili jednostruko- ili polisupstituirani s jednim ili više supstituenata, koji su svaki odabrani neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-8-alkil, OCF3, C1-8-alkil, C(=O)-OH, CF3, NH2, NH(C1-8-alkil), N(C1-8-alkil)2, SH, S-C1-8-alkil, SCF3 i S(=O)2OH;
4. Supstituirani nikotinamidi prema zahtjevu 3, naznačeni time da
R14a i R14b, svaki neovisno jedan od drugog, označavaju H; F; Cl; Br; I; NO2; CF3; CN; metil; etil; n-propil; izo-propil; ciklopropil; n-butil; sek.-butil; tert.-butil;
CH2CF3; OH; O-metil; O-etil; O-(CH2)2-O-CH3; O-(CH2)2-OH; OCF3; NH2; NH-metil; N(metil)2; NH-etil; N(etil)2; ili N(metil)(etil);
m je 0, 1 ili 2;
n je 0; i B označava C1-4-alkil, zasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, OH, O-C1-4-alkil, OCF3 i CF3; C3-10-cikloalkil, zasićen, nesupstituiran; fenil, naftil, piridil, tienil, svaki nesupstituiran ili jednostruko- ili dvostruko- ili trostruko-supstituiran s jednim, dva ili tri supstituenta, svaki neovisno odabran iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-4-alkil, OCF3, C1-4-alkil, C(=O)-OH, CF3, NH2, NH(C1-4-alkil), N(C1-4-alkil)2, SH, S-C1-4-alkil, SCF3, S(=O)2OH.
5. Supstituirani nikotinamidi prema jednom od zahtjeva 1-4, naznačeni time da R2, R3 i R4 svaki označavaju, neovisno jedan od drugoga, H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; SH; SCF3; metil; CH2-O-metil; CH2-OH; C2-6-alkil; O-C1-6-alkil, S-C1-6-alkil, svaki zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata odabranih, neovisno jedan od drugoga, iz skupine koja sadrži F, Cl, Br, I, OH, =O i O-C1-4-alkil; C3-7-cikloalkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran; NRaRb, gdje Ra i Rb svaki označava, neovisno jedan od drugoga, H ili C1-4-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata odabranih, neovisno jedan od drugoga, iz skupine koja sadrži OH, =O i O-C1-4-alkil, ili Ra i Rb zajedno s atomom dušika koji iste spaja tvore heterociklil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s C1-4-alkilom.
6. Supstituirani nikotinamidi prema zahtjevu 5, naznačeni time da
R2, R3 i R4 svaki označava, neovisno jedan od drugoga, H; F; Cl; Br; I; metil; etil; n-propil; izo-propil; ciklopropil; CN; CF3; O-metil; OCF3; S-metil; SCF3.
7. Supstituirani nikotinamidi prema jednom od zahtjeva 1-6, naznačeni time da
R5, R6, R7, R8, R10, R11, R12 i R13 poželjno svaki označava, neovisno jedan od drugoga, H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; SH; SCF3; metil; etil; n-propil; izo-propil; n-butil, sek.-butil, tert.-butil, O-metil; O-etil; O-(CH2)2-O-CH3; O-(CH2)2-OH; S-metil; S-etil; ciklopropil, ciklobutil; ciklopentil; cikloheksil;
ili R5 i R6 ili R7 i R8 ili R10 i R11 ili R12 i R13 ili R5 i R11 ili R5 i R7 ili R5 i R13 ili R7 i R13 ili R7 i R11 ili R11 i R13 tvore ciklopropil, ciklobutil, ciklopentil ili cikloheksil zajedno s ugljikovim atomom(ima) koje iste spaja, svaki nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki nesupstituiran; gdje relevantni preostali supstituenti R5, R6, R7, R8, R10, R11, R12 i R13 imaju gore navedeno značenje.
8. Supstituirani nikotinamidi prema jednom od zahtjeva 1-7, naznačeni time da
R9 označava C3-10-cikloalkil ili heterociklil, svaki zasićen ili nezasićen, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki odabran neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, =O, O-C1-4-alkil, OCF3, C1-4-alkil, CF3, SH, S-C1-4-alkil i SCF3; aril ili heteroaril, svaki nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, koji su svaki odabrani neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-4-alkil, OCF3, C1-4-alkil, CF3, NH2, NH(C1-4-alkil), N(C1-4-alkil)2, SH, S-C1-4-alkil i SCF3; ili označava CRcRd, gdje Rc i Rd, svaki neovisno jedan od drugog, supstituiraju C1-4-alkil, zasićen ili nezasićen, razgranat ili nerazgranat, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki odabran neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, OH, O-C1-4-alkil, CF3, OCF3 i SCF3.
9. Supstituirani nikotinamidi prema jednom od zahtjeva 1-8, naznačeni time da
R9 označava fenil, piridil i tienil, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki odabran neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, CN, OH, O-C1-4-alkil, OCF3, C1-4-alkil, CF3, SH, S-C1-4-alkil i SCF3.
10. Supstituirani nikotinamidi prema jednom od zahtjeva 1-9, naznačeni time da
A1 označava S; i
A2 označava CR12R13;
R1 označava dio strukture (T1-1)
[image]
gdje
R14a i R14b, svaki neovisno jedan od drugog, označavaju H; F; Cl; Br; I; metil; etil; n-propil; izo-propil; n-butil; sek.-butil; tert.-butil; OH; O-metil; O-etil; O-(CH2)2-O-CH3; ili O-(CH2)2-OH;
m označava 0, 1 ili 2;
B označava metil; etil; n-propil; izo-propil; n-butil; sek.-butil; tert.-butil; ciklopropil; ciklobutil; ciklopentil; cikloheksil; cikloheptil; adamantil; biciklo[2.2.1]heptil; biciklo[2.2.2]oktil; fenil, piridil, tienil, svaki nesupstituiran ili jednostruko-, dvostruko- ili trostruko-supstituiran s jednim, dva ili tri supstituenta, svaki odabran neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, NO2, CN, OH, O-C1-4-alkil, OCF3, C1-4-alkil, C(=O)-OH, CF3, NH2, NH(C1-4-alkil), N(C1-4-alkil)2, SH, S-C1-4-alkil, SCF3, S(=O)2OH;
R2, R3 i R4, svaki neovisno jedan od drugog, označavaju H; F; Cl; metil; etil; CF3 ili O-metil;
R5, R6, R7, R8, R10, R11, R12 i R13, svaki neovisno jedan od drugog, označavaju H; F; Cl; metil; etil; n-propil, izo-propil; ciklopropil;
R9 označava fenil, piridil i tienil, nesupstituiran ili jednostruko- ili polisupstituiran s jednim ili više supstituenata, svaki odabran neovisno jedan od drugog iz skupine koju čine F, Cl, Br, I, CN, metil, etil, n-propil, izo-propil, n-butil, sek.-butil, tert.-butil, O-metil, O-etil, O-n-propil, O-izo-propil, O-butil, O-sek.-butil, O-tert.-butil, OH, OCF3, CF3, SH, S-C1-4-alkil i SCF3.
11. Supstituirani nikotinamidi prema jednom od zahtjeva 1-10, naznačeni time da su odabrani iz skupine koju čine
1 amid 2-(3-fenil-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
2 amid 2-(3-cikloheksil-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
3 amid 2-[(3-okso-fenil-propil)sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
4 amid N-(tiofen-2-il-metil)-2-[2-[3-(trifluorometil)-fenoksi]-etilsulfanil]-piridin-3-karboksilne kiseline;
5 amid 2-(4-metil-pentilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
7 amid 2-(4-fenil-butil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
8 amid 2-[(3-benzosulfonil)-propil]- N-(cikloheksil-metil)-piridin-3-karboksilne kiseline;
9 amid N-(cikloheksil-metil)-2-(4-fenil-butil)- piridin-3-karboksilne kiseline;
10 amid 2-[3-benzosulfonil)-propil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
12 amid N-(tiofen-2-il-metil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]-propil]-piridin-3-karboksilne kiseline;
13 amid N-(tiofen-2-il-metil)-2-[3-[[3-(trifluoro-metil)fenil]sulfanil]-propil]-piridin-3-karboksilne kiseline;
16 amid 2-(2-fenilsulfanil-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
17 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
18 amid N-(tiofen-2-il-metil)-2-[3-[3-(trifluorometil)fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
19 amid 2-[2-[(4-fluorofenil)sulfanil]-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
20 amid N-(tiofen-2-il-metil)-2-[2-[[3-(trifluorometil)fenil]sulfanil]-propilsulfanil]-piridin-3-karboksilne kiseline;
21 amid N-(tiofen-2-il-metil)-2-[4-[3-(trifluorometil)-fenil]-butil]-piridin-3-karboksilne kiseline;
22 amid 2-[4-(4-fluorofenil)-butil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
23 amid 2-(3-fenilsulfanil-propil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
24 amid 2-[(1-metil-fenilsulfanil-etil)sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
25 amid N-(cikloheptil-metil)-2-[4-[3-(trifluorometil)fenil]-butil]-piridin-3-karboksilne kiseline;
26 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[4-[3-(trifluorometil)fenil]-butil]-piridin-3-karboksilne kiseline;
27 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[3-(trifluorometil)fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
28 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-(4-metil-pentilsulfanil)-piridin-3-karboksilne kiseline;
29 amid N-(cikloheptil-metil)-2-[3-[(4-fluorofenil)sulfanil]-propil]-piridin-3-karboksilne kiseline;
30 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[(4-fluorofenil)sulfanil]-propil]-piridin-3-karboksilne kiseline;
31 amid N-(cikloheptil-metil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]-propil]-piridin-3-karboksilne kiseline;
32 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]-propil]-piridin-3-karboksilne kiseline;
33 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-(3-fenil-propilsulfanil)-piridin-3-karboksilne kiseline;
34 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[4-(trifluorometil)-fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
35 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(4-klorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
36 amid N-[(3,5-difluoro-fenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
37 amid N-[(5-kloro-tiofen-2-il)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
38 amid N-[(2,2-dimetil-ciklopropil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
39 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
40 amid N-(cikloheksil-metil)-2-[3-(4-fluorofenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
41 amid N-(cikloheptil-metil)-2-[3-(4-fluorofenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
43 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[[3-(4-fluorofenil)-3-okso-propil]sulfanil]-piridin-3-karboksilne kiseline;
44 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[(3-okso-fenil-propil)sulfanil]-piridin-3-karboksilne kiseline;
45 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-(heksilsulfanil)-piridin-3-karboksilne kiseline;
46 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-(2-fenoksi-etilsulfanil)-piridin-3-karboksilne kiseline;
47 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[2-[3-(trifluorometil)-fenoksi]-etilsulfanil]-piridin-3-karboksilne kiseline;
48 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3,3,3-trifluoro-propil)-piridin-3-karboksilne kiseline;
49 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[2-(4-fluoro-fenoksi)-etilsulfanil]-piridin-3-karboksilne kiseline;
52 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-(3-naftalen-1-il-propilsulfanil)-piridin-3-karboksilne kiseline;
53 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[3-fluoro-4-(trifluorometil)-fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
54 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[4-fluoro-3-(trifluorometil)-fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
55 amid N-(ciklooktil-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
56 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(4-metoksifenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
57 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(4metoksifenil)-metil]-piridin-3-karboksilne kiseline;
59 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[[3-(trifluorometil)fenil]-metil]-piridin-3-karboksilne kiseline;
60 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3,4-difluoro-fenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
61 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3,5-difluoro-fenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
62 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(2,4-difluoro-fenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
63 amid N-[(2-fluorofenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]- piridin-3-karboksilne kiseline;
64 amid N-[(3-fluorofenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]- piridin-3-karboksilne kiseline;
65 amid N-[(4-fluorofenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
66 amid N-benzil-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
67 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[(1-metil-3-fenil-propil)sulfanil]-piridin-3-karboksilne kiseline;
68 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3,4,5-trifluoro-fenil)-propilsulfanil]- piridin-3-karboksilne kiseline;
69 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-[3-fluoro-5-(trifluorometil)-fenil]-propilsulfanil]- piridin-3-karboksilne kiseline;
70 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3-metoksifenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
71 amid N-[(3,4-difluoro-fenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
72 amid N-(2,3-dihidro-benzofuran-5-il-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
73 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(3-hidroksifenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
74 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[[3-(4-fluorofenil)-1-metilpropil]sulfanil]-piridin-3-karboksilne kiseline;
75 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[[3-(4-fluorofenil)-2-metil-propil]sulfanil]- piridin-3-karboksilne kiseline;
76 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(2-metoksifenil)-metil]-piridin-3-karboksilne kiseline;
77 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-metoksifenil)-metil]-piridin-3-karboksilne kiseline;
78 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-fenetil-piridin-3-karboksilne kiseline;
79 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[[4-(trifluorometiloksi)-fenil]-metil]-piridin-3-karboksilne kiseline;
80 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[[4-(trifluorometil)-fenil]-metil]-piridin-3-karboksilne kiseline;
81 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(2-piridin-3-il-etil)-piridin-3-karboksilne kiseline;
82 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(2-piridin-2-il-etil)-piridin-3-karboksilne kiseline;
83 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(2-hidroksifenil)-metil]-piridin-3-karboksilne kiseline;
84 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-hidroksifenil)-metil]-piridin-3-karboksilne kiseline;
85 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[2-(m-toliol)-etil]-piridin-3-karboksilne kiseline;
86 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[2-(o-toliol)-etil]-piridin-3-karboksilne kiseline;
87 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[[3-(trifluorometiloksi)-fenil]-metil]-piridin-3-karboksilne kiseline;
88 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(4-hidroksifenil)-metil]-piridin-3-karboksilne kiseline;
89 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(2-piridin-4-il-etil)-piridin-3-karboksilne kiseline;
90 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[2-(p-toliol)-etil]-piridin-3-karboksilne kiseline;
91 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(4-fluorofenil)-butilsulfanil]-piridin-3-karboksilne kiseline;
92 amid N-(5-biciklo[2.2.1]heptanil-metil)-2-[3-(2,4,5-trifluoro-fenil)-propilsulfanil]- piridin-3-karboksilne kiseline;
93 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3-piridin-2-il-propil)-piridin-3-karboksilne kiseline;
94 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3-piridin-3-il-propil)-piridin-3-karboksilne kiseline;
95 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3-piridin-4-il-propil)-piridin-3-karboksilne kiseline;
96 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-propil-piridin-3-karboksilne kiseline;
97 amid N-butil-2-[3-(4-fluorofenil)-propilsulfanil]- piridin-3-karboksilne kiseline;
98 amid 2-(3-piridin-3-il-propilsilfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
99 amid 2-[3-(p-toliol)-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
100 amid 2-(4-fenil-butilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
101 amid 2-(3-piridin-4-il-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
102 amid 2-(3-naftalen-2-il-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
103 amid 2-[3-(m-toliol)-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
104 amid N-(tiofen-2-il-metil)-2-(3-tiofen-2-il-propilsulfanil)-piridin-3-karboksilne kiseline;
105 amid 2-[(1-metil-3-fenil-propil)sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
106 amid N-(tiofen-2-il-metil)-2-(3-tiofen-3-il-propilsulfanil)-piridin-3-karboksilne kiseline;
107 amid 2-[[1-metil-3-[3-(trifluorometil)fenil]-propil]sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
108 amid 2-[(2-benzil-cikloheksil)sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
109 amid 2-[3-[3-metil-5-(trifluorometil)-fenil]-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
110 amid 2-[4-(3,4-difluoro-fenil)-butilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
111 amid 2-(3-piridin-2-il-propilsulfanil)-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
113 amid 2-[3-[4-metil-3-(trifluorometil)-fenil]-propilsulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
114 amid 2-[(3-fenil-cikloheksil)sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
116 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil-N-(3,3-dimetil-butil)-piridin-3-karboksilne kiseline;
117 amid N-(cikloheptil-metil)-2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-piridin-3-karboksilne kiseline;
118 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(tiofen-2-il-metil)-piridin-3-karboksilne kiseline;
119 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(1,2,3,4-tetrahidro-naftalen-2-il-metil)-piridin-3-karboksilne kiseline;
120 amid N-(2,3-dihidro-1H-inden-2-il-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
121 amid N-(1,3-benzodioksol-5-il-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
122 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-fenil-fenil)-metil]-piridin-3-karboksilne kiseline;
123 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-metil-cikloheksil)-metil]-piridin-3-karboksilne kiseline;
124 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-[(4-fluorofenil)-metil]-piridin-3-karboksilne kiseline;
125 amid N-(3,3-dimetil-2-okso-butil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
127 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(piridin-3-il-metil)-piridin-3-karboksilne kiseline;
128 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(piridin-4-il-metil)-piridin-3-karboksilne kiseline;
129 metil ester 3-[[[2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksil]amino]-metil]-benzojeve kiseline;
130 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[3-(2-metoksifenil)-propil]-piridin-3-karboksilne kiseline;
132 amid N-[(4-fluorofenil)-metil]-2-[[1-metil-3-[3-(trilfuorometil)fenil]-propil]sulfanil]-piridin-3-karboksilne kiseline;
133 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3-metil-butil)-piridin-3-karboksilne kiseline;
134 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(tetrahidro-piran-2-il-metil)-piridin-3-karboksilne kiseline;
135 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[3-(1H-pirazol-1-il)-propil]-piridin-3-karboksilne kiseline;
136 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(naftalen-2-il-metil)-piridin-3-karboksilne kiseline;
137 amid N-(2,3-dihidro-[1,4]benzodioksin-6-il-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
138 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-morfolin-4-il-fenil)-metil]-piridin-3-karboksilne kiseline;
139 amid N-(2,3-dihidro-benzofuran-6-il-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
140 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[[3-(1H-pirazol-1-il)-fenil]-metil]-piridin-3-karboksilne kiseline;
141 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[3-(1H-[1,2,3]triazol-1-il)-propil]-piridin-3-karboksilne kiseline;
142 amid N-(7-biciklo[2.2.1]heptanil-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
144 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(tiazol-2-il-metil)-piridin-3-karboksilne kiseline;
145 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(tiazol-5-il-metil)-piridin-3-karboksilne kiseline;
146 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(oksazol-2-il-metil)-piridin-3-karboksilne kiseline;
148 amid N-(3,3-dimetil-butil)-2-[3-(4-fluorofenil)-propilsulfanil]-4-metil-piridin-3-karboksilne kiseline;
149 amid N-(3,3-dimetil-butil)-2-[[1-metil-3-[3-(trifluorometil)fenil]-propil]sulfanil]-piridin-3-karboksilne kiseline;
150 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(kinolin-7-il-metil)-piridin-3-karboksilne kiseline;
151 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-piridin-2-il-fenil)-metil]-piridin-3-karboksilne kiseline;
152 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-piridin-3-il-fenil)-metil]-piridin-3-karboksilne kiseline;
153 amid N-(3,3-dimetil-butil)-2-[[(1R)-1-metil-3-fenil-propil]sulfanil]-piridin-3-karboksilne kiseline;
154 kiseline amid N-(3,3-dimetil-butil)-2-[[(11S)-1-metil-3-fenil-propil]sulfanil]-piridin-3-karboksilne;
155 amid 2-[(2-benzil-ciklopentil)sulfanil]-N-(3,3-dimetil-butil)-piridin-3-karboksilne kiseline;
156 amid N-(7-biciklo[2.2.1]heptanil-metil)-2-[3-[3-(trifluorometil)fenil]-propilsulfanil]- piridin-3-karboksilne kiseline;
157 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[3-(1H-[1,2,4]triazol-1-il)-propil]-piridin-3-karboksilne kiseline;
158 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-([1,3,4]oksadiazol-2-il-metil)-piridin-3-karboksilne kiseline;
159 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(3-piridin-4-il-fenil)-metil]-piridin-3-karboksilne kiseline;
160 amid N-[[4-(ciklopropilmetil)-3,4-dihidro-2H-[1,4]benzoksazin-6-il]-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
161 amid N-[(4-etil-3,4-dihidro-2H-[1,4]benzoksazin-6-il)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
162 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(4-metil-3,4-dihidro-2H-[1,4]benzoksazin-6-il)-metil]-piridin-3-karboksilne kiseline;
163 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(3-metil-3-fenil-butil)-piridin-3-karboksilne kiseline;
164 amid N-(7-biciklo[2.2.1]heptanil-metil)-2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]- piridin-3-karboksilne kiseline;
165 amid 2-[[3,3-difluoro-3-[3-(trifluorometil)fenil]-propil]sulfanil]-N-[(4-fluorofenil)-metil]-piridin-3-karboksilne kiseline;
166 amid 2-[[3,3-difluoro-3-[3-(trifluorometil)fenil]-propil]sulfanil]-N-(3,3-dimetil-butil)-piridin-3-karboksilne kiseline
168 amid 2-[[3,3-difluoro-3-(4-(fluorofenil)propil]sulfanil]-N-[(3-fluorofenil)-metil]-piridin-3-karboksilne kiseline;
170 amid N-butil-2-[[3,3-(difluoro-3-(4-fluorofenil)-propil]sulfanil]-piridin-3-karboksilne kiseline;
171 amid 2-[[3,3-difluoro-3-(4-(fluorofenil)propil]sulfanil]-N-[(2-metoksi-etil)-piridin-3-karboksilne kiseline;
172 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(2-metoksi-etil)-piridin-3-karboksilne kiseline;
173 amid N-[(4-fluoro-2-hidroksi-fenil)-metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
174 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(furan-2-il-metil)-piridin-3-karboksilne kiseline;
175 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-[(5-metil-furan-2-il)-metil]-piridin-3-karboksilne kiseline;
176 amid N-[(4-fluorofenil)-metil]-2-[[3-(4-fluorofenil)-1-metil-propil]sulfanil]-piridin-3-karboksilne kiseline;
177 amid 2-[[3-(4-(fluorofenil)-1-metil-propil]sulfanil]-N-(3-metil-butil)-piridin-3-karboksilne kiseline;
178 amid N-(7-biciklo[2.2.1]heptanil-metil)-2-[[3-(4-fluorofenil)-1-metil-propil]sulfanil]-piridin-3-karboksilne kiseline;
179 amid 2-[[3,3-difluoro-3-(4-(fluorofenil)propil]sulfanil-N-(tetrahidro-furan-2-il-metil)-piridin-3-karboksilne kiseline;
180 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(tetrahidro-piran-2-il-metil)-piridin-3-karboksilne kiseline;
181 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(tetrahidro-furan-2-il-metil)-piridin-3-karboksilne kiseline;
182 amid 2-[3-(4-fluorofenil)-propilsulfanil]-N-(2-metoksi-3,3-dimetil-butil)-piridin-3-karboksilne kiseline;
183 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(m-toliol-metil)-piridin-3-karboksilne kiseline;
184 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-[(3,5-dimetil-fenil)-metil]-piridin-3-karboksilne kiseline;
185 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-propil-piridin-3-karboksilne kiseline;
186 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-heksil-piridin-3-karboksilne kiseline;
187 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(tetrahidro-furan-3-il-metil)-piridin-3-karboksilne kiseline;
188 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(tetrahidro-piran-3-il-metil)-piridin-3-karboksilne kiseline;
189 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(tetrahidro-piran-4-il-metil)-piridin-3-karboksilne kiseline;
190 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(furan-2-il-metil)-piridin-3-karboksilne kiseline;
191 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-[(5-metil-furan-2-il)-metil]-piridin-3-karboksilne kiseline;
192 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-pentil-piridin-3-karboksilne kiseline;
193 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(3-metoksi-butil)-piridin-3-karboksilne kiseline;
194 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(2-metoksi-propil)-piridin-3-karboksilne kiseline;
195 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(2-metoksi-butil)-piridin-3-karboksilne kiseline;
196 metil ester 3-[[2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-piridin-3-karbonil]amino]-propionske kiseline;
197 3-[[2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-piridin-3-karbonil]amino]- propionska kiselina;
198 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(2-dimetilaminoetil)-piridin-3-karboksilne kiseline;
199 amid 2-[[3-(3,4-difluoro-fenil)-1-metil-propil]sulfanil]-N-[(4-fluorofenil)-metil]-piridin-3-karboksilne kiseline;
200 amid 2-[[3-(3,4-difluoro-fenil)-1-metil-propil]sulfanil]-N-(3-metil-butil)-piridin-3-karboksilne kiseline;
201 amid N-[(4-fluorofenil)-metil]-2-[[3-(3-fluorofenil)-1-metil-propil]sulfanil]-piridin-3-karboksilne kiseline;
202 amid 2-[[3-(3-fluorofenil)-1-metil-propil]sulfanil]-N-(3-metil-butil)-piridin-3-karboksilne kiseline;
203 amid N-(3-metil-butil)-2-[[1-metil-3-[3-(trifluorometil)fenil]-propil]sulfanil]-piridin-3-karboksilne kiseline;
204 amid 2-[[3-(3,4-difluoro-fenil)-3,3-difluoro-propil]sulfanil]-N-[(4-fluorofenil)-metil]-piridin-3-karboksilne kiseline;
205 amid N-(1-biciklo[2.2.1]heptanil-metil)-2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]- piridin-3-karboksilne kiseline;
206 amid N-(1-biciklo[2.2.1]heptanil-metil)-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
207 amid N-[(4-fluorofenil)-metil]-2-[3-[3-(trifluorometil)fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
208 amid N-(3-metil-butil)-2-[3-[3-(trifluorometil)fenil]-propilsulfanil]-piridin-3-karboksilne kiseline;
209 amid 2-[[3-(3,4-difluoro-fenil)-3,3-difluoro-propil]sulfanil]-N-(3-metil-butil)-piridin-3-karboksilne kiseline;
210 amid N-(7-biciklo[2.2.1]heptanil-metil)-2-[[3-(3,4-difluoro-fenil)-3,3-difluoro-propil]sulfanil]- piridin-3-karboksilne kiseline;
211 amid 2-[[3,3-difluoro-3-(4-fluorofenil)-propil]sulfanil]-N-(2-hidroksi-etil)-piridin-3-karboksilne kiseline;
224 amid N-[(4-fluoro-2-metoksi-fenil)metil]-2-[3-(4-fluorofenil)-propilsulfanil]-piridin-3-karboksilne kiseline;
ili njihove fiziološki kompatibilne soli.
12. Lijekovi naznačeni time da sadrže barem jedan supstituirani nikotinamid prema jednom od zahtjeva 1 do 11, svaki u obliku jednog stereoizomera ili njihove smjese, slobodnih spojeva i/ili njihovih fiziološki kompatibilnih soli, kao i mogućih pogodnih aditiva i/ili pomoćnih sredstava i/ili mogućih dodatnih aktivnih tvari.
13. Uporaba barem jednog supstituiranog nikotinamida prema jednom od zahtjeva 1 do 11, svakog u obliku jednog stereoizomera ili njihove smjese, slobodnog spoja i/ili njegovih fiziološki kompatibilnih soli, naznačena time da je za proizvodnju lijeka za liječenje boli, epilepsije, poremećaja anksioznosti, ovisnosti, manije, bipolarnih poremećaja, migrene, kognitivnih bolesti, diskinezije povezane s distonijom i/ili urinarne inkontinencije.
14. Supstituirani nikotinamid prema jednom od zahtjeva 1 do 11, svaki u obliku jednog stereoizomera ili njihove smjese, slobodnog spoja i/ili njegovih fiziološki kompatibilnih soli, naznačen time da je za liječenje boli, epilepsije, poremećaja anksioznosti, ovisnosti, manije, bipolarnih poremećaja, migrene, kognitivnih bolesti, diskinezije povezane s distonijom i/ili urinarne inkontinencije.
Applications Claiming Priority (3)
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EP09003598 | 2009-03-12 | ||
EP10708139.0A EP2406226B1 (de) | 2009-03-12 | 2010-03-11 | Substituierte nicotinamide als kcnq2/3 modulatoren |
PCT/EP2010/001507 WO2010102809A1 (de) | 2009-03-12 | 2010-03-11 | Substituierte nicotinamide als kcnq2/3 modulatoren |
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EP (1) | EP2406226B1 (hr) |
JP (1) | JP5670359B2 (hr) |
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CN (1) | CN102369188B (hr) |
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BR (1) | BRPI1008948A2 (hr) |
CA (1) | CA2754998C (hr) |
CO (1) | CO6410303A2 (hr) |
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DK (1) | DK2406226T3 (hr) |
EC (1) | ECSP11011347A (hr) |
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HR (1) | HRP20151260T1 (hr) |
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PE (1) | PE20120780A1 (hr) |
PL (1) | PL2406226T3 (hr) |
PT (1) | PT2406226E (hr) |
RU (1) | RU2529904C2 (hr) |
SI (1) | SI2406226T1 (hr) |
TW (1) | TWI475020B (hr) |
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Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
TWI461197B (zh) * | 2009-03-12 | 2014-11-21 | 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier | |
AU2011295405B2 (en) | 2010-08-27 | 2015-01-22 | Grünenthal GmbH | Substituted 2-oxy-quinoline-3-carboxamides as KCNQ2/3 modulators |
US8653102B2 (en) | 2010-08-27 | 2014-02-18 | Gruenenthal Gmbh | Substituted 2-oxo- and 2-thioxo-dihydroquinoline-3-carboxamides as KCNQ2/3 modulators |
TW201211007A (en) | 2010-08-27 | 2012-03-16 | Gruenenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
US8618129B2 (en) | 2010-09-01 | 2013-12-31 | Gruenenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators |
AU2015201122B2 (en) * | 2010-10-20 | 2016-02-25 | Grunenthal Gmbh | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
MX367623B (es) | 2010-10-20 | 2019-08-29 | Gruenenthal Gmbh | 6-amino-nicotinamidas sustituidas como moduladores de kcnq2/3. |
US9168259B2 (en) | 2010-10-20 | 2015-10-27 | Grünenthal GmbH | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
FR2968661B1 (fr) * | 2010-12-14 | 2016-01-01 | Oreal | Procede de depigmentation des matieres keratiniques a l'aide de composes thiopyridinones |
JP6033403B2 (ja) | 2012-04-18 | 2016-11-30 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Kcnq2/3調節因子としてのoh含有基を有する置換6−アミノ−ニコチンアミド類 |
MX2014012491A (es) | 2012-04-18 | 2014-11-14 | Grünenthal GmbH | 4-aminobenzamidas sustituidas como moduladores de kcnq2/3. |
WO2014056620A1 (en) * | 2012-10-11 | 2014-04-17 | Grünenthal GmbH | Treatment and/or prophylaxis of tspo mediated diseases and/or disorders |
AU2013351550A1 (en) | 2012-11-28 | 2015-07-16 | Grünenthal GmbH | Specific carboxamides as KCNQ2/3 modulators |
US9248122B2 (en) | 2012-11-28 | 2016-02-02 | Grünenthal GmbH | Heteroquinoline-3-carboxamides as KCNQ2/3 modulators |
CN104513171B (zh) * | 2013-09-30 | 2017-09-01 | 中国科学院过程工程研究所 | 一种玛咖酰胺的合成方法及其用途 |
EP3210969B1 (en) | 2014-10-24 | 2021-04-28 | ONO Pharmaceutical Co., Ltd. | Kcnq2-5 channel activator |
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 |
CN111840267A (zh) * | 2020-08-05 | 2020-10-30 | 牡丹江医学院 | 一种治疗小儿口腔黏膜疾病的药物及其制备方法 |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 (fr) | 1995-03-01 | 1996-09-06 | Banyu Pharmaceutical Co., Ltd. | Derives de l'arylthioacetamide |
DE19738616A1 (de) | 1997-09-04 | 1999-03-11 | Clariant Gmbh | 4-Hydroxychinolin-3-carbonsäure-Derivate als Lichtschutzmittel |
JP2002534512A (ja) | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドglp−1アゴニスト |
DE60037321D1 (de) | 1999-08-04 | 2008-01-17 | Icagen Inc | Benzanilide als öffner des kaliumkanals |
JP2003506388A (ja) * | 1999-08-04 | 2003-02-18 | アイカゲン インコーポレイテッド | 疼痛および不安症を処置または予防するための方法 |
RU2317988C2 (ru) * | 2000-08-14 | 2008-02-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция на их основе, применение фармацевтической композиции и способ ингибирования активности катепсина s |
WO2002066036A1 (en) * | 2001-02-20 | 2002-08-29 | Bristol-Myers Squibb Company | 2,4-disubstituted pyrimidine-5-carboxamide derivatives as kcnq potassium channel modulators |
US6855829B2 (en) | 2001-02-20 | 2005-02-15 | Bristol-Myers Squibb Company | 3-fluoro-2-oxindole modulators of KCNQ potassium channels and use thereof in treating migraine and mechanistically related disease |
US6593349B2 (en) | 2001-03-19 | 2003-07-15 | Icagen, Inc. | Bisarylamines as potassium channel openers |
EP1372654A4 (en) | 2001-04-06 | 2007-10-03 | Smithkline Beecham Corp | QUINOLINE INHIBITORS OF HYAK1 AND HYAK3 KINASES |
JP2005539081A (ja) | 2002-09-17 | 2005-12-22 | ファルマシア コーポレイション | 芳香族肝臓x受容体モジュレーター |
CA2505195C (en) | 2002-12-23 | 2012-07-10 | Icagen, Inc. | Quinazolinones as potassium channel modulators |
EP1449841A1 (en) | 2003-02-19 | 2004-08-25 | Bayer CropScience SA | New fungicidal compounds |
RU2006115602A (ru) * | 2003-10-08 | 2007-11-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Модуляторы переносчиков атф-связывающих кассет |
BRPI0510598A (pt) * | 2004-05-04 | 2007-11-20 | Pfizer | compostos de amida de aril ou heteroaril substituìdos |
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 |
EP2298766B1 (en) | 2005-03-03 | 2013-09-18 | H. Lundbeck A/S | Pharmaceutical formulations comrpising a substituted pyridine derivative |
ATE432259T1 (de) | 2005-07-20 | 2009-06-15 | Lilly Co Eli | Pyridinderivate als dipeptedyl-peptidase-hemmer |
US7670416B2 (en) * | 2005-08-04 | 2010-03-02 | I-Tech Ab | Use of a combination of substances to prevent biofouling organisms |
EP1922311A2 (en) | 2005-09-09 | 2008-05-21 | Brystol-Myers Squibb Company | Acyclic ikur inhibitors |
EP1951685A1 (en) | 2005-11-18 | 2008-08-06 | NeuroSearch A/S | Novel quinazoline derivatives and their medical use |
CA2658190C (en) | 2006-07-20 | 2013-01-29 | Amgen Inc. | Di-amino-substituted heterocyclic compounds and methods of use |
US7872128B2 (en) | 2006-07-20 | 2011-01-18 | Amgen Inc. | Benzisoxazole and isoxazolo-pyridine compounds and method of use |
US20100022589A1 (en) | 2006-07-27 | 2010-01-28 | Mccoull William | Pyridine-3-carboxamide compounds and their use for inhibiting 11-beta-hydroxysteroid dehydrogenase |
US20080039542A1 (en) * | 2006-08-11 | 2008-02-14 | General Electric Company | Composition and associated method |
US8563566B2 (en) | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
KR101167773B1 (ko) * | 2007-08-03 | 2012-07-24 | 에프. 호프만-라 로슈 아게 | Taar1 리간드로서의 피리딘카복스아마이드 및 벤즈아마이드 유도체 |
DE102007044277A1 (de) * | 2007-09-17 | 2009-03-19 | Grünenthal GmbH | Substituierte Nicotinamid-Verbindungen und deren Verwendung in Arzneimitteln |
US8299123B2 (en) | 2007-10-19 | 2012-10-30 | Boehringer Ingelheim International Gmbh | CCR10 antagonists |
US8367700B2 (en) | 2008-12-17 | 2013-02-05 | Gruenenthal Gmbh | Substituted 4-(1.2,3,4-tetrahydroisoquinolin-2-yl)-4-oxobutyric acid amide as KCNQ2/3 modulators |
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 |
TWI461197B (zh) | 2009-03-12 | 2014-11-21 | 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier | |
AR082734A1 (es) | 2010-08-27 | 2012-12-26 | Gruenenthal Gmbh | Quinolino-3-carboxamidas sustituidas como moduladores de kcnq2/3 |
TW201211007A (en) | 2010-08-27 | 2012-03-16 | Gruenenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
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