RU2014111321A - Гидразиды 3-пиридинкарбоновых кислот в качестве агентов, повышающих содержание холестерина липопротеинов высокой плотности - Google Patents
Гидразиды 3-пиридинкарбоновых кислот в качестве агентов, повышающих содержание холестерина липопротеинов высокой плотности Download PDFInfo
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- RU2014111321A RU2014111321A RU2014111321/04A RU2014111321A RU2014111321A RU 2014111321 A RU2014111321 A RU 2014111321A RU 2014111321/04 A RU2014111321/04 A RU 2014111321/04A RU 2014111321 A RU2014111321 A RU 2014111321A RU 2014111321 A RU2014111321 A RU 2014111321A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- halogen
- group
- trifluoroethoxy
- substituted
- Prior art date
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- 239000003795 chemical substances by application Substances 0.000 title claims 3
- 108010023302 HDL Cholesterol Proteins 0.000 title 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title 1
- 150000002814 niacins Chemical class 0.000 title 1
- 235000001968 nicotinic acid Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract 17
- 150000002367 halogens Chemical class 0.000 claims abstract 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- -1 C-cycloalkyl Chemical group 0.000 claims abstract 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 4
- 239000011593 sulfur Substances 0.000 claims abstract 4
- 125000004429 atom Chemical group 0.000 claims abstract 3
- 125000002541 furyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 208000028867 ischemia Diseases 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims 6
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims 6
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 3
- 102000015779 HDL Lipoproteins Human genes 0.000 claims 3
- 108010010234 HDL Lipoproteins Proteins 0.000 claims 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 206010021024 Hypolipidaemia Diseases 0.000 claims 3
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 3
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 230000002641 glycemic effect Effects 0.000 claims 3
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 3
- 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 230000002792 vascular Effects 0.000 claims 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- CUQZGBSEDZOUEI-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-cyclobutyloxy-n-(4-hydroxypiperidin-1-yl)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1NC(=O)C(C=C1C=2C=CC(Cl)=CC=2)=CN=C1OC1CCC1 CUQZGBSEDZOUEI-UHFFFAOYSA-N 0.000 claims 2
- ZRHUKEFBCXAQJZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-hydroxypiperidin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 ZRHUKEFBCXAQJZ-UHFFFAOYSA-N 0.000 claims 2
- VWXJKJDXJWFBFE-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[4-(2-hydroxyethyl)piperazin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CN(CCO)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 VWXJKJDXJWFBFE-UHFFFAOYSA-N 0.000 claims 2
- BLXKBXAIPYKIMF-UHFFFAOYSA-N 5-cyclohexyl-n-(4-hydroxypiperidin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C2CCCCC2)=C1 BLXKBXAIPYKIMF-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 208000037487 Endotoxemia Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- ONEZQSDDZYQSQQ-UHFFFAOYSA-N 5-(3-fluorophenyl)-n'-methyl-n'-phenyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1=CC=CC(F)=C1 ONEZQSDDZYQSQQ-UHFFFAOYSA-N 0.000 claims 1
- MFIYRECNFTZQJQ-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=C(F)C(Cl)=CC=2)=C1 MFIYRECNFTZQJQ-UHFFFAOYSA-N 0.000 claims 1
- ZEVMYALVVREGBZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-n'-(2,2,2-trifluoroethyl)pyridine-3-carbohydrazide Chemical compound FC(F)(F)CNNC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 ZEVMYALVVREGBZ-UHFFFAOYSA-N 0.000 claims 1
- PBJQDCWJKCGOCR-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(cyclopropylmethoxy)-n-(4-hydroxypiperidin-1-yl)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1NC(=O)C(C=C1C=2C=CC(Cl)=CC=2)=CN=C1OCC1CC1 PBJQDCWJKCGOCR-UHFFFAOYSA-N 0.000 claims 1
- XKZATUGERUGCIC-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(3-hydroxypropyl)-n'-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound OCCCN(C)NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 XKZATUGERUGCIC-UHFFFAOYSA-N 0.000 claims 1
- QZKDUCQXKHTJHW-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(6-chloropyridazin-3-yl)-n'-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=C(Cl)N=NC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1=CC=C(Cl)C=C1 QZKDUCQXKHTJHW-UHFFFAOYSA-N 0.000 claims 1
- RKVTXARFCMZBNX-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-methyl-n'-phenyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1=CC=C(Cl)C=C1 RKVTXARFCMZBNX-UHFFFAOYSA-N 0.000 claims 1
- JFAPMSSRPJKNSA-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(1,1-dioxo-1,4-thiazinan-4-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCS(=O)(=O)CC2)C=C1C1=CC=C(Cl)C=C1 JFAPMSSRPJKNSA-UHFFFAOYSA-N 0.000 claims 1
- PWVQODNMXRBSMV-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-methyl-3-oxopiperazin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1C(=O)N(C)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 PWVQODNMXRBSMV-UHFFFAOYSA-N 0.000 claims 1
- KQBUYLPQSJXMMW-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-methylsulfonylpiperazin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 KQBUYLPQSJXMMW-UHFFFAOYSA-N 0.000 claims 1
- KDFZCAGDYKHHJJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[4-(2-hydroxyethyl)piperidin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(CCO)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 KDFZCAGDYKHHJJ-UHFFFAOYSA-N 0.000 claims 1
- RGGUURMMKQGAMX-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[4-(hydroxymethyl)piperidin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(CO)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(Cl)=CC=2)=C1 RGGUURMMKQGAMX-UHFFFAOYSA-N 0.000 claims 1
- WUAQPWNIVUPPBN-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[5-(morpholin-4-ylmethyl)-2-oxo-1,3-oxazolidin-3-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2C(OC(CN3CCOCC3)C2)=O)C=C1C1=CC=C(Cl)C=C1 WUAQPWNIVUPPBN-UHFFFAOYSA-N 0.000 claims 1
- ZQSLHUCGSTXSGC-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-morpholin-4-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCOCC2)C=C1C1=CC=C(Cl)C=C1 ZQSLHUCGSTXSGC-UHFFFAOYSA-N 0.000 claims 1
- RQHVKGJMPBAXHH-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(4-hydroxypiperidin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(O)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(=CC=2)C#N)=C1 RQHVKGJMPBAXHH-UHFFFAOYSA-N 0.000 claims 1
- VSMIVMIUBIZUMS-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-[4-(2-hydroxyethyl)piperidin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1CC(CCO)CCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C=2C=CC(=CC=2)C#N)=C1 VSMIVMIUBIZUMS-UHFFFAOYSA-N 0.000 claims 1
- XNPOSEFXTNYHKW-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-morpholin-4-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCOCC2)C=C1C1=CC=C(C#N)C=C1 XNPOSEFXTNYHKW-UHFFFAOYSA-N 0.000 claims 1
- WCSBZEBNZICNHZ-UHFFFAOYSA-N 5-cyclohexyl-n'-methyl-n'-phenyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1CCCCC1 WCSBZEBNZICNHZ-UHFFFAOYSA-N 0.000 claims 1
- ZALMXDAKFFZMCI-INIZCTEOSA-N 5-cyclohexyl-n-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound COC[C@@H]1CCCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C2CCCCC2)=C1 ZALMXDAKFFZMCI-INIZCTEOSA-N 0.000 claims 1
- DDOOXPDNFMCJNZ-UHFFFAOYSA-N 5-cyclohexyl-n-morpholin-4-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCOCC2)C=C1C1CCCCC1 DDOOXPDNFMCJNZ-UHFFFAOYSA-N 0.000 claims 1
- QVVKRBFVBWDLBL-UHFFFAOYSA-N 5-cyclohexyl-n-pyrrolidin-1-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCCC2)C=C1C1CCCCC1 QVVKRBFVBWDLBL-UHFFFAOYSA-N 0.000 claims 1
- VUWPBFVPAGTLTH-UHFFFAOYSA-N 5-cyclopentyl-n'-methyl-n'-phenyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1CCCC1 VUWPBFVPAGTLTH-UHFFFAOYSA-N 0.000 claims 1
- UVYIWCZDIVRFQF-UHFFFAOYSA-N 5-cyclopentyl-n-(2-oxopyrrolidin-1-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2C(CCC2)=O)C=C1C1CCCC1 UVYIWCZDIVRFQF-UHFFFAOYSA-N 0.000 claims 1
- UWSOZBSWZBRYOH-UHFFFAOYSA-N 5-cyclopentyl-n-morpholin-4-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCOCC2)C=C1C1CCCC1 UWSOZBSWZBRYOH-UHFFFAOYSA-N 0.000 claims 1
- CQMOXRGXEVTVCI-BETUJISGSA-N 5-cyclopropyl-6-(cyclopropylmethoxy)-n-[(2s,6r)-2,6-dimethylmorpholin-4-yl]pyridine-3-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1NC(=O)C(C=C1C2CC2)=CN=C1OCC1CC1 CQMOXRGXEVTVCI-BETUJISGSA-N 0.000 claims 1
- UKSJFPJNCLXWSY-UHFFFAOYSA-N 5-cyclopropyl-n'-(4-fluorophenyl)-n'-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=C(F)C=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1CC1 UKSJFPJNCLXWSY-UHFFFAOYSA-N 0.000 claims 1
- VLTMUNQVHNTUQN-UHFFFAOYSA-N 5-cyclopropyl-n-(1,1-dioxo-1,4-thiazinan-4-yl)-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCS(=O)(=O)CC2)C=C1C1CC1 VLTMUNQVHNTUQN-UHFFFAOYSA-N 0.000 claims 1
- PSSRMWWAGFEYGQ-ZDUSSCGKSA-N 5-cyclopropyl-n-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound COC[C@@H]1CCCN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C2CC2)=C1 PSSRMWWAGFEYGQ-ZDUSSCGKSA-N 0.000 claims 1
- QLXCBGDEQUSBOG-PHIMTYICSA-N 5-cyclopropyl-n-[(2s,6r)-2,6-dimethylmorpholin-4-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1NC(=O)C1=CN=C(OCC(F)(F)F)C(C2CC2)=C1 QLXCBGDEQUSBOG-PHIMTYICSA-N 0.000 claims 1
- QZSMJBJHLYUNDY-UHFFFAOYSA-N 5-cyclopropyl-n-morpholin-4-yl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound FC(F)(F)COC1=NC=C(C(=O)NN2CCOCC2)C=C1C1CC1 QZSMJBJHLYUNDY-UHFFFAOYSA-N 0.000 claims 1
- SZLGXOWVURPREO-UHFFFAOYSA-N 6-cyclobutyloxy-n'-(4-fluorophenyl)-5-(furan-2-yl)pyridine-3-carbohydrazide Chemical compound C1=CC(F)=CC=C1NNC(=O)C(C=C1C=2OC=CC=2)=CN=C1OC1CCC1 SZLGXOWVURPREO-UHFFFAOYSA-N 0.000 claims 1
- 241000283707 Capra Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002158 endotoxin Substances 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- GPTWGBOORMMVAV-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-5-cyclopentyl-n'-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=C(Cl)N=NC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1CCCC1 GPTWGBOORMMVAV-UHFFFAOYSA-N 0.000 claims 1
- KRCRHEWULMKEHU-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-6-cyclobutyloxy-5-(furan-2-yl)-n'-methylpyridine-3-carbohydrazide Chemical compound C=1C=C(Cl)N=NC=1N(C)NC(=O)C(C=C1C=2OC=CC=2)=CN=C1OC1CCC1 KRCRHEWULMKEHU-UHFFFAOYSA-N 0.000 claims 1
- WBPULFKJXCKTKX-UHFFFAOYSA-N n'-methyl-5-(oxan-4-yl)-n'-phenyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C(C=1)=CN=C(OCC(F)(F)F)C=1C1CCOCC1 WBPULFKJXCKTKX-UHFFFAOYSA-N 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/86—Hydrazides; Thio or imino analogues thereof
- C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- 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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- C—CHEMISTRY; METALLURGY
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- C07D401/00—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
- C07D401/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11180929 | 2011-09-12 | ||
| EP11180929.9 | 2011-09-12 | ||
| PCT/EP2012/067469 WO2013037703A1 (en) | 2011-09-12 | 2012-09-07 | 3 -pyridine carboxylic acid hydrazides as hdl-cholesterol raising agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014111321A true RU2014111321A (ru) | 2015-10-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014111321/04A RU2014111321A (ru) | 2011-09-12 | 2012-09-07 | Гидразиды 3-пиридинкарбоновых кислот в качестве агентов, повышающих содержание холестерина липопротеинов высокой плотности |
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| US (1) | US8648099B2 (enExample) |
| EP (1) | EP2755953A1 (enExample) |
| JP (1) | JP5815874B2 (enExample) |
| KR (1) | KR20140057652A (enExample) |
| CN (1) | CN103781765A (enExample) |
| BR (1) | BR112014005634A2 (enExample) |
| CA (1) | CA2844865A1 (enExample) |
| MX (1) | MX2014001860A (enExample) |
| RU (1) | RU2014111321A (enExample) |
| WO (1) | WO2013037703A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104725353A (zh) * | 2015-03-12 | 2015-06-24 | 佛山市赛维斯医药科技有限公司 | 一类含烟酸酰胺和哌啶结构ptp1b抑制剂及其用途 |
| US20200085810A1 (en) | 2018-07-26 | 2020-03-19 | Hoffmann-La Roche Inc. | Compounds for use in treating kidney disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005531520A (ja) * | 2002-03-28 | 2005-10-20 | メルク エンド カムパニー インコーポレーテッド | 置換2,3−ジフェニルピリジン類 |
| KR100970050B1 (ko) * | 2005-04-06 | 2010-07-16 | 에프. 호프만-라 로슈 아게 | Cb1 역 작용제로서 피리딘-3-카복사마이드 유도체 |
| WO2007011760A2 (en) * | 2005-07-15 | 2007-01-25 | Kalypsys, Inc. | Inhibitors of mitotic kinesin |
| US7629346B2 (en) * | 2006-06-19 | 2009-12-08 | Hoffmann-La Roche Inc. | Pyrazinecarboxamide derivatives as CB1 antagonists |
| JP2010505789A (ja) * | 2006-10-04 | 2010-02-25 | エフ.ホフマン−ラ ロシュ アーゲー | Hdl−コレステロール上昇剤としての3−ピリジンカルボキサミド及び2−ピラジンカルボキサミド誘導体 |
| TW200940537A (en) * | 2008-02-26 | 2009-10-01 | Astrazeneca Ab | Heterocyclic urea derivatives and methods of use thereof |
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2012
- 2012-09-07 RU RU2014111321/04A patent/RU2014111321A/ru not_active Application Discontinuation
- 2012-09-07 MX MX2014001860A patent/MX2014001860A/es unknown
- 2012-09-07 BR BR112014005634A patent/BR112014005634A2/pt not_active IP Right Cessation
- 2012-09-07 WO PCT/EP2012/067469 patent/WO2013037703A1/en not_active Ceased
- 2012-09-07 KR KR1020147008882A patent/KR20140057652A/ko not_active Ceased
- 2012-09-07 JP JP2014530158A patent/JP5815874B2/ja not_active Expired - Fee Related
- 2012-09-07 CN CN201280044104.1A patent/CN103781765A/zh active Pending
- 2012-09-07 EP EP12754017.7A patent/EP2755953A1/en not_active Withdrawn
- 2012-09-07 CA CA2844865A patent/CA2844865A1/en not_active Abandoned
- 2012-09-11 US US13/609,429 patent/US8648099B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20130065876A1 (en) | 2013-03-14 |
| EP2755953A1 (en) | 2014-07-23 |
| US8648099B2 (en) | 2014-02-11 |
| MX2014001860A (es) | 2014-05-30 |
| JP5815874B2 (ja) | 2015-11-17 |
| JP2014527073A (ja) | 2014-10-09 |
| BR112014005634A2 (pt) | 2017-03-28 |
| KR20140057652A (ko) | 2014-05-13 |
| CA2844865A1 (en) | 2013-03-21 |
| WO2013037703A1 (en) | 2013-03-21 |
| CN103781765A (zh) | 2014-05-07 |
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| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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