RU2010120536A - Pyridine and pyrazine derivatives useful for the treatment of cellular cellular disorders - Google Patents
Pyridine and pyrazine derivatives useful for the treatment of cellular cellular disorders Download PDFInfo
- Publication number
- RU2010120536A RU2010120536A RU2010120536/04A RU2010120536A RU2010120536A RU 2010120536 A RU2010120536 A RU 2010120536A RU 2010120536/04 A RU2010120536/04 A RU 2010120536/04A RU 2010120536 A RU2010120536 A RU 2010120536A RU 2010120536 A RU2010120536 A RU 2010120536A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- piperidin
- amino
- alkoxy
- methyl
- Prior art date
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- 150000003216 pyrazines Chemical class 0.000 title claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- 230000001413 cellular effect Effects 0.000 title 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 306
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 48
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 39
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 20
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 239000001257 hydrogen Substances 0.000 claims abstract 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000011593 sulfur Chemical group 0.000 claims abstract 4
- -1 cyano, amino Chemical group 0.000 claims 346
- 125000003545 alkoxy group Chemical group 0.000 claims 48
- 125000001589 carboacyl group Chemical group 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000005236 alkanoylamino group Chemical group 0.000 claims 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 4
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 238000003780 insertion Methods 0.000 claims 3
- 230000037431 insertion Effects 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims 2
- 125000005281 alkyl ureido group Chemical group 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 2
- LXBFANNWWZLTJB-AWEZNQCLSA-N (2s)-1-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(hydroxymethyl)pyrazol-1-yl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCC1N1N=C(CO)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 LXBFANNWWZLTJB-AWEZNQCLSA-N 0.000 claims 1
- DDEXNXZJGHYENN-HNNXBMFYSA-N (2s)-1-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(methoxymethyl)pyrazol-1-yl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(COC)=NN1C1CCN(C(=O)[C@H](C)O)CC1 DDEXNXZJGHYENN-HNNXBMFYSA-N 0.000 claims 1
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- WMUHCTYUSKRLSA-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(methoxymethyl)pyrazol-1-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(COC)=NN1C1CCN(C(=O)CN(C)C)CC1 WMUHCTYUSKRLSA-UHFFFAOYSA-N 0.000 claims 1
- CWRITCURTRDHEE-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(methoxymethyl)pyrazol-1-yl]piperidin-1-yl]-2-hydroxyethanone Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(COC)=NN1C1CCN(C(=O)CO)CC1 CWRITCURTRDHEE-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- ABNXEGUBGHXRRQ-UHFFFAOYSA-N 2,9-diazaspiro[5.5]undecane Chemical compound C1CCNCC21CCNCC2 ABNXEGUBGHXRRQ-UHFFFAOYSA-N 0.000 claims 1
- BZMIIMSLIAIYBB-UHFFFAOYSA-N 2-[2-amino-5-[3-(methoxymethyl)-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-3-yl]-1,3-benzoxazole-4-carbonitrile Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC(=C3N=2)C#N)C(COC)=NN1C1CCN(C)CC1 BZMIIMSLIAIYBB-UHFFFAOYSA-N 0.000 claims 1
- QVKCWAJEKXKIPC-UHFFFAOYSA-N 2-[2-amino-5-[3-methyl-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-3-yl]-1,3-benzoxazole-4-carbonitrile Chemical compound C1CN(C)CCC1N1N=C(C)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC(=C3N=2)C#N)=C1 QVKCWAJEKXKIPC-UHFFFAOYSA-N 0.000 claims 1
- YZGZWOAVHCLZRI-UHFFFAOYSA-N 2-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(hydroxymethyl)pyrazol-1-yl]piperidin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCC1N1N=C(CO)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 YZGZWOAVHCLZRI-UHFFFAOYSA-N 0.000 claims 1
- GJTSCVGYZBKYRL-UHFFFAOYSA-N 2-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(methoxymethyl)pyrazol-1-yl]piperidin-1-yl]-n-methylacetamide Chemical compound C1CN(CC(=O)NC)CCC1N1N=C(COC)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 GJTSCVGYZBKYRL-UHFFFAOYSA-N 0.000 claims 1
- ABVRMVABYMYMNT-UHFFFAOYSA-N 2-[4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-3-(methoxymethyl)pyrazol-1-yl]piperidin-1-yl]ethanol Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(COC)=NN1C1CCN(CCO)CC1 ABVRMVABYMYMNT-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- BQJWXYWAYWOZQC-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-5-(3-methyl-1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(C)=NN1C1CCNCC1 BQJWXYWAYWOZQC-UHFFFAOYSA-N 0.000 claims 1
- IRPWHDCXRYOUPN-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1CN(C)CCC1N1N=CC(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 IRPWHDCXRYOUPN-UHFFFAOYSA-N 0.000 claims 1
- MQKNEHOSWIDNRX-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)C(COC)=NN1C1CCN(C)CC1 MQKNEHOSWIDNRX-UHFFFAOYSA-N 0.000 claims 1
- VDLPZFPQISBPJF-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-5-[3-methyl-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1CN(C)CCC1N1N=C(C)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 VDLPZFPQISBPJF-UHFFFAOYSA-N 0.000 claims 1
- JUFFBMNEDKNVLU-UHFFFAOYSA-N 3-(4-fluoro-1,3-benzoxazol-2-yl)-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1CN(C)CCC1N1N=CC(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC(F)=C3N=2)=C1 JUFFBMNEDKNVLU-UHFFFAOYSA-N 0.000 claims 1
- BYKGRNHPEJKEST-UHFFFAOYSA-N 3-(4-fluoro-1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC(F)=C3N=2)C(COC)=NN1C1CCN(C)CC1 BYKGRNHPEJKEST-UHFFFAOYSA-N 0.000 claims 1
- KGBMQQXMUUFJRI-UHFFFAOYSA-N 3-(4-fluoro-1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-piperidin-4-ylpyrazol-4-yl]pyridin-2-amine Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC(F)=C3N=2)C(COC)=NN1C1CCNCC1 KGBMQQXMUUFJRI-UHFFFAOYSA-N 0.000 claims 1
- QFBFFXBERDQXPQ-UHFFFAOYSA-N 3-(7-methoxy-1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound C1=C(C=2C=C(C(N)=NC=2)C=2OC3=C(OC)C=CC=C3N=2)C(COC)=NN1C1CCN(C)CC1 QFBFFXBERDQXPQ-UHFFFAOYSA-N 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims 1
- HJGMRAKQWLKWMH-UHFFFAOYSA-N 8-methyl-8-azabicyclo[3.2.1]octan-3-amine Chemical compound C1C(N)CC2CCC1N2C HJGMRAKQWLKWMH-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- NQQYCHSVGLIZSM-UHFFFAOYSA-N [4-[6-amino-5-(1,3-benzoxazol-2-yl)pyridin-3-yl]-1-(1-methylpiperidin-4-yl)pyrazol-3-yl]methanol Chemical compound C1CN(C)CCC1N1N=C(CO)C(C=2C=C(C(N)=NC=2)C=2OC3=CC=CC=C3N=2)=C1 NQQYCHSVGLIZSM-UHFFFAOYSA-N 0.000 claims 1
- IQCBAFJVQWGQCT-UHFFFAOYSA-N [4-[6-amino-5-(7-methoxy-1,3-benzoxazol-2-yl)pyridin-3-yl]-1-(1-methylpiperidin-4-yl)pyrazol-3-yl]methanol Chemical compound O1C=2C(OC)=CC=CC=2N=C1C(C(=NC=1)N)=CC=1C(C(=N1)CO)=CN1C1CCN(C)CC1 IQCBAFJVQWGQCT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. Соединение формулы I ! , ! в которой W представляет собой СН или N; ! J представляет собой О или S; ! каждый из G1, G2, G3 и G4 выбран из СН и N, при условии, что не более чем два из G1, G2, G3 и G4 представляют собой N; ! кольцо А выбрано из: ! (1) фенила, замещенного R1 и возможно замещенного группами R2 в количестве вплоть до трех; или ! (2) 5- или 6-членного моноциклического гетероарильного кольца с кольцевыми гетероатомами в количестве вплоть до трех, выбранными из кислорода, азота и серы, причем указанное кольцо замещено R1 и возможно замещено группами R2 в количестве вплоть до трех; или ! (3) 8-, 9- или 10-членной бициклической кольцевой системы, возможно содержащей вплоть до трех кольцевых гетероатомов, выбранных из кислорода, азота и серы, и возможно замещенной R1 и возможно замещенной группами R2 в количестве вплоть до трех; ! R1 представляет собой группу формулы: !R4-X1-, ! где X1 представляет собой прямую связь или выбран из О, S, SO, SO2, N(R5), CO, CH(OR5), CON(R5), N(R5)CO, N(R5)CON(R5), SO2N(R5), N(R5)SO2, C(R5)2O, OC(R5)2, C(R5)2S, SC(R5)2, C(R5)2, C(R5)2N(R5) и N(R5)N(R5)2, где каждый R5 независимо выбран из водорода, (1-8С)алкила, гидрокси-(1-6С)алкила, (1-6С)алкокси-(1-6С)алкила, циано-(1-6С)алкила, галогено-(1-6С)алкила, ди-[(1-6С)алкил]амино-(1-6С)алкила, (1-6С)алкиламино-(1-6С)алкила или амино-(1-6С)алкила, и когда X1 представляет собой прямую связь или выбран из CH(OR5), C(R5)2O, C(R5)2S, C(R5)2 или C(R5)2N(R5), где R5 имеет любое из значений, определенных выше, тогда R4 представляет собой гидрокси-(1-6С)алкил, (1-6С)алкокси-(1-6С)алкил, R5-S, R5-S(O), R5-SO2, R5-SO2-O, R5-S-(1-6С)алкил, R5-S(O)-(1-6С)алкил, R5-SO2-(1-6C)aлкил, N,N-ди(R5)сульфамоил, N,N-ди-(R5)cyльфaмoил-(1-6C)aлкил, R5-SO2N(R5), R5-SO2N(R5)-(1-6C)aлкил, R5-CON(R5), R5O-CON(R5), R5-CON(R5)-(1-6C)aлкил, R5O-CON(R5)-(1-6C)aлкил, (R5)2N-SO2N(R5), (R5)2N-SO2N(R5)-(1-6C)aлкил, (R5)2N-CON(R5), (R5)2N-CON(R5)-(1-6С)алкил, R5-CO 1. The compound of formula I! ! in which W represents CH or N; ! J represents O or S; ! each of G1, G2, G3 and G4 is selected from CH and N, provided that no more than two of G1, G2, G3 and G4 are N; ! Ring A is selected from:! (1) phenyl substituted with R1 and optionally substituted with up to three groups of R2; or ! (2) a 5- or 6-membered monocyclic heteroaryl ring with up to three ring heteroatoms selected from oxygen, nitrogen, and sulfur, said ring being substituted with R1 and optionally substituted with up to three R2 groups; or ! (3) an 8-, 9- or 10-membered bicyclic ring system, possibly containing up to three ring heteroatoms selected from oxygen, nitrogen and sulfur, and optionally substituted with R1 and possibly substituted with up to three groups of R2; ! R1 is a group of the formula:! R4-X1-,! where X1 is a direct bond or is selected from O, S, SO, SO2, N (R5), CO, CH (OR5), CON (R5), N (R5) CO, N (R5) CON (R5), SO2N (R5), N (R5) SO2, C (R5) 2O, OC (R5) 2, C (R5) 2S, SC (R5) 2, C (R5) 2, C (R5) 2N (R5) and N (R5) N (R5) 2, where each R5 is independently selected from hydrogen, (1-8C) alkyl, hydroxy- (1-6C) alkyl, (1-6C) alkoxy- (1-6C) alkyl, cyano- ( 1-6C) alkyl, halo- (1-6C) alkyl, di - [(1-6C) alkyl] amino (1-6C) alkyl, (1-6C) alkylamino (1-6C) alkyl or amino (1-6C) alkyl, and when X1 is a direct bond or is selected from CH (OR5), C (R5) 2O, C (R5) 2S, C (R5) 2 or C (R5) 2N (R5), where R5 has any of the meanings defined above, then R4 is hydroxy- (1-6C) alkyl, (1-6C) alkoc and- (1-6C) alkyl, R5-S, R5-S (O), R5-SO2, R5-SO2-O, R5-S- (1-6C) alkyl, R5-S (O) - (1 -6C) alkyl, R5-SO2- (1-6C) alkyl, N, N-di (R5) sulfamoyl, N, N-di- (R5) sylphamoyl- (1-6C) alkyl, R5-SO2N (R5) , R5-SO2N (R5) - (1-6C) alkyl, R5-CON (R5), R5O-CON (R5), R5-CON (R5) - (1-6C) alkyl, R5O-CON (R5) - (1-6C) alkyl, (R5) 2N-SO2N (R5), (R5) 2N-SO2N (R5) - (1-6C) alkyl, (R5) 2N-CON (R5), (R5) 2N-CON (R5) - (1-6C) alkyl, R5-CO
Claims (18)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07301491 | 2007-10-25 | ||
| EP07301491.2 | 2007-10-25 | ||
| EP07305005.6 | 2007-12-21 | ||
| EP07305005 | 2007-12-21 | ||
| EP08305180.5 | 2008-05-19 |
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| RU2010120536A true RU2010120536A (en) | 2011-11-27 |
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| RU2010120536/04A RU2010120536A (en) | 2007-10-25 | 2008-10-22 | Pyridine and pyrazine derivatives useful for the treatment of cellular cellular disorders |
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| RU (1) | RU2010120536A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2632885C2 (en) * | 2012-01-31 | 2017-10-11 | Дайити Санкио Компани, Лимитед | Pyridon derivatives |
| RU2707953C2 (en) * | 2014-07-07 | 2019-12-02 | Дайити Санкио Компани, Лимитед | Pyridone derivative having tetrahydropyranylmethyl group |
-
2008
- 2008-10-22 RU RU2010120536/04A patent/RU2010120536A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2632885C2 (en) * | 2012-01-31 | 2017-10-11 | Дайити Санкио Компани, Лимитед | Pyridon derivatives |
| RU2707953C2 (en) * | 2014-07-07 | 2019-12-02 | Дайити Санкио Компани, Лимитед | Pyridone derivative having tetrahydropyranylmethyl group |
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