HRP20100611T1 - Novi spojevi - Google Patents
Novi spojevi Download PDFInfo
- Publication number
- HRP20100611T1 HRP20100611T1 HR20100611T HRP20100611T HRP20100611T1 HR P20100611 T1 HRP20100611 T1 HR P20100611T1 HR 20100611 T HR20100611 T HR 20100611T HR P20100611 T HRP20100611 T HR P20100611T HR P20100611 T1 HRP20100611 T1 HR P20100611T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- pyrazol
- ylmethyl
- indan
- methyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 128
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 241000282414 Homo sapiens Species 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- -1 -OH Chemical group 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 159000000000 sodium salts Chemical class 0.000 claims 3
- YGOSHXARHJHGIK-UHFFFAOYSA-N 2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]acetic acid Chemical compound CCC1=NN(CC(O)=O)C(CC)=C1CC1=CC(C)=C(O)C2=C1CCC2 YGOSHXARHJHGIK-UHFFFAOYSA-N 0.000 claims 2
- OFUOCIUIWKDKPA-UHFFFAOYSA-N 3-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1CC1=CC(C)=C(O)C2=C1CCC2 OFUOCIUIWKDKPA-UHFFFAOYSA-N 0.000 claims 2
- ZVHPWMABDPKBKG-UHFFFAOYSA-N 4-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]butanoic acid Chemical compound CC1=NN(CCCC(O)=O)C(C)=C1CC1=CC(C)=C(O)C2=C1CCC2 ZVHPWMABDPKBKG-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 229910004727 OSO3H Inorganic materials 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000003054 hormonal effect Effects 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 208000003532 hypothyroidism Diseases 0.000 claims 2
- 230000002989 hypothyroidism Effects 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 238000009256 replacement therapy Methods 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 239000005495 thyroid hormone Substances 0.000 claims 2
- 229940036555 thyroid hormone Drugs 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- KJIHPGJXPICTFS-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazole Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC(=C1C)C(C)=NN1C1=CC=C(Cl)C=C1 KJIHPGJXPICTFS-UHFFFAOYSA-N 0.000 claims 1
- ZKOWDFOMOFELSZ-UHFFFAOYSA-N 1-(carboxymethyl)-5-(5-chlorothiophen-2-yl)-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazole-3-carboxylic acid Chemical class C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C(O)=O)=NN(CC(O)=O)C=1C1=CC=C(Cl)S1 ZKOWDFOMOFELSZ-UHFFFAOYSA-N 0.000 claims 1
- WTZZXMREEQCSLA-UHFFFAOYSA-N 1-[2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]acetyl]pyrrolidine-2-carboxylic acid Chemical class CCC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(CC)=NN1CC(=O)N1CCCC1C(O)=O WTZZXMREEQCSLA-UHFFFAOYSA-N 0.000 claims 1
- KIYAWPDQZXKCEZ-UHFFFAOYSA-N 1-[2-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]acetyl]pyrrolidine-2-carboxylic acid Chemical class CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC(=O)N1CCCC1C(O)=O KIYAWPDQZXKCEZ-UHFFFAOYSA-N 0.000 claims 1
- WHFCNJNIQJYRIH-UHFFFAOYSA-N 1-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-2-(4-methylsulfonylphenyl)ethanone Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC(=C1C)C(C)=NN1C(=O)CC1=CC=C(S(C)(=O)=O)C=C1 WHFCNJNIQJYRIH-UHFFFAOYSA-N 0.000 claims 1
- AHQFEQSEJVOSPZ-UHFFFAOYSA-N 2-(carboxymethyl)-5-(5-chlorothiophen-2-yl)-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazole-3-carboxylic acid Chemical class C1=C(C)C(OC)=C2CCCC2=C1CC(=C(N(CC(O)=O)N=1)C(O)=O)C=1C1=CC=C(Cl)S1 AHQFEQSEJVOSPZ-UHFFFAOYSA-N 0.000 claims 1
- MGGBOMOYUQGDFI-UHFFFAOYSA-N 2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]-n-(2h-tetrazol-5-yl)acetamide Chemical compound CCC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(CC)=NN1CC(=O)NC1=NN=NN1 MGGBOMOYUQGDFI-UHFFFAOYSA-N 0.000 claims 1
- WMZWUWGEABWINL-UHFFFAOYSA-N 2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound CCC1=NN(CC(=O)NC(C)C)C(CC)=C1CC1=CC(C)=C(O)C2=C1CCC2 WMZWUWGEABWINL-UHFFFAOYSA-N 0.000 claims 1
- DZDKBHQGTOSMEQ-UHFFFAOYSA-N 2-[3,5-diethyl-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]acetohydrazide Chemical compound CCC1=NN(CC(=O)NN)C(CC)=C1CC1=CC(C)=C(OC)C2=C1CCC2 DZDKBHQGTOSMEQ-UHFFFAOYSA-N 0.000 claims 1
- QFSPAUJUCYWYDM-UHFFFAOYSA-N 2-[3,5-diethyl-4-[[6-[(4-fluorophenyl)methyl]-7-hydroxy-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]acetic acid Chemical compound CCC1=NN(CC(O)=O)C(CC)=C1CC1=CC(CC=2C=CC(F)=CC=2)=C(O)C2=C1CCC2 QFSPAUJUCYWYDM-UHFFFAOYSA-N 0.000 claims 1
- LWZJHMLHAKZVBU-UHFFFAOYSA-N 2-[3,5-diethyl-4-[[7-hydroxy-6-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]acetic acid Chemical compound CCC1=NN(CC(O)=O)C(CC)=C1CC1=CC(CN2CCCC2)=C(O)C2=C1CCC2 LWZJHMLHAKZVBU-UHFFFAOYSA-N 0.000 claims 1
- ZLZHLFRZQOSQGS-UHFFFAOYSA-N 2-[3,5-diethyl-4-[[7-hydroxy-6-(pyrrolidine-1-carbonyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]acetic acid Chemical compound CCC1=NN(CC(O)=O)C(CC)=C1CC1=CC(C(=O)N2CCCC2)=C(O)C2=C1CCC2 ZLZHLFRZQOSQGS-UHFFFAOYSA-N 0.000 claims 1
- HWCQMIDZSVLZSA-UHFFFAOYSA-N 2-[3,5-diethyl-4-[[7-methoxy-6-(methoxymethyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]acetic acid Chemical compound CCC1=NN(CC(O)=O)C(CC)=C1CC1=CC(COC)=C(OC)C2=C1CCC2 HWCQMIDZSVLZSA-UHFFFAOYSA-N 0.000 claims 1
- QKIIJZCBKNLRRQ-UHFFFAOYSA-N 2-[3-amino-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-5-(4-methoxyphenyl)pyrazol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(N(N=C1N)CC(O)=O)=C1CC1=CC(C)=C(OC)C2=C1CCC2 QKIIJZCBKNLRRQ-UHFFFAOYSA-N 0.000 claims 1
- XUFHDRLMHJYMRC-UHFFFAOYSA-N 2-[4-(1h-indol-5-ylmethyl)-3,5-dimethylpyrazol-1-yl]ethanol Chemical compound CC1=NN(CCO)C(C)=C1CC1=CC=C(NC=C2)C2=C1 XUFHDRLMHJYMRC-UHFFFAOYSA-N 0.000 claims 1
- PSISVVHFFXMFPR-UHFFFAOYSA-N 2-[4-(1h-indol-5-yloxy)-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1=NN(CC(O)=O)C(C)=C1OC1=CC=C(NC=C2)C2=C1 PSISVVHFFXMFPR-UHFFFAOYSA-N 0.000 claims 1
- RUPSTHYDSSCNME-UHFFFAOYSA-N 2-[4-[(4-hydroxy-3-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1=NN(CC(O)=O)C(C)=C1CC1=CC(C)=C(O)C2=C1CCCC2 RUPSTHYDSSCNME-UHFFFAOYSA-N 0.000 claims 1
- IQFYCVMCQQSWCE-UHFFFAOYSA-N 2-[4-[(7-chloro-2,3-dihydro-1h-inden-4-yl)oxy]-3-thiophen-2-ylpyrazol-1-yl]acetic acid Chemical compound N=1N(CC(=O)O)C=C(OC=2C=3CCCC=3C(Cl)=CC=2)C=1C1=CC=CS1 IQFYCVMCQQSWCE-UHFFFAOYSA-N 0.000 claims 1
- LBJNLXULTCYXQH-UHFFFAOYSA-N 2-[4-[(7-chloro-2,3-dihydro-1h-inden-4-yl)oxy]-5-thiophen-2-ylpyrazol-1-yl]acetic acid Chemical compound OC(=O)CN1N=CC(OC=2C=3CCCC=3C(Cl)=CC=2)=C1C1=CC=CS1 LBJNLXULTCYXQH-UHFFFAOYSA-N 0.000 claims 1
- JLTBQGCQFSSZAX-UHFFFAOYSA-N 2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]-n-(2h-tetrazol-5-yl)acetamide Chemical compound CC1=C(OC=2C=3CCCC=3C(O)=CC=2)C(C)=NN1CC(=O)NC1=NN=NN1 JLTBQGCQFSSZAX-UHFFFAOYSA-N 0.000 claims 1
- HIVZHBIPASCUJI-UHFFFAOYSA-N 2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound OC(=O)C(C)N1N=C(C)C(OC=2C=3CCCC=3C(O)=CC=2)=C1C HIVZHBIPASCUJI-UHFFFAOYSA-N 0.000 claims 1
- URHXEZSHPGQGDN-UHFFFAOYSA-N 2-[4-[(7-hydroxy-3,6-dimethyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1CCC(C(=C(C)C=2)O)=C1C=2CC=1C(C)=NN(CC(O)=O)C=1C URHXEZSHPGQGDN-UHFFFAOYSA-N 0.000 claims 1
- ZVEUWYYDYYWXLH-UHFFFAOYSA-N 2-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-di(propan-2-yl)pyrazol-1-yl]acetic acid Chemical compound CC(C)C1=NN(CC(O)=O)C(C(C)C)=C1CC1=CC(C)=C(O)C2=C1CCC2 ZVEUWYYDYYWXLH-UHFFFAOYSA-N 0.000 claims 1
- KUVKFAWOPJZOGL-UHFFFAOYSA-N 2-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound OC(=O)C(C)N1N=C(C)C(CC=2C=3CCCC=3C(O)=C(C)C=2)=C1C KUVKFAWOPJZOGL-UHFFFAOYSA-N 0.000 claims 1
- DLXKAJPSTAGAEN-UHFFFAOYSA-N 2-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1=NN(CC(O)=O)C(C)=C1OC1=CC(C)=C(O)C2=C1CCC2 DLXKAJPSTAGAEN-UHFFFAOYSA-N 0.000 claims 1
- NRFXPCFVPSHAPP-UHFFFAOYSA-N 2-[4-[(7-methoxy-2,2,6-trimethyl-1,3-dihydroinden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound C1=C(C)C(OC)=C2CC(C)(C)CC2=C1CC=1C(C)=NN(CC(O)=O)C=1C NRFXPCFVPSHAPP-UHFFFAOYSA-N 0.000 claims 1
- QVLZUZCRQNAXJK-UHFFFAOYSA-N 2-[4-[[6-[(4-fluorophenyl)methyl]-7-hydroxy-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1=NN(CC(O)=O)C(C)=C1CC1=CC(CC=2C=CC(F)=CC=2)=C(O)C2=C1CCC2 QVLZUZCRQNAXJK-UHFFFAOYSA-N 0.000 claims 1
- HGTRSGHTTIZEGK-UHFFFAOYSA-N 2-[4-[[7-hydroxy-6-[(4-methylphenyl)methyl]-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound CC1=NN(CC(O)=O)C(C)=C1CC1=CC(CC=2C=CC(C)=CC=2)=C(O)C2=C1CCC2 HGTRSGHTTIZEGK-UHFFFAOYSA-N 0.000 claims 1
- BZSHYKGEJBOWFL-UHFFFAOYSA-N 2-[4-[[7-methoxy-6-methyl-2-(4-nitrophenoxy)-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]acetic acid Chemical compound C1=C(C)C(OC)=C2CC(OC=3C=CC(=CC=3)[N+]([O-])=O)CC2=C1CC=1C(C)=NN(CC(O)=O)C=1C BZSHYKGEJBOWFL-UHFFFAOYSA-N 0.000 claims 1
- RKOVAZFUCNXXSU-UHFFFAOYSA-N 2-[5-amino-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3-(4-methoxyphenyl)pyrazol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(CC(O)=O)C(N)=C1CC1=CC(C)=C(OC)C2=C1CCC2 RKOVAZFUCNXXSU-UHFFFAOYSA-N 0.000 claims 1
- WROWPNNEVNNLLK-UHFFFAOYSA-N 2-[[2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]acetyl]amino]acetic acid Chemical compound CCC1=NN(CC(=O)NCC(O)=O)C(CC)=C1CC1=CC(C)=C(O)C2=C1CCC2 WROWPNNEVNNLLK-UHFFFAOYSA-N 0.000 claims 1
- BKNDTFXUZUPKCX-UHFFFAOYSA-N 2-[[2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]acetyl]amino]acetic acid Chemical compound CC1=NN(CC(=O)NCC(O)=O)C(C)=C1OC1=CC=C(O)C2=C1CCC2 BKNDTFXUZUPKCX-UHFFFAOYSA-N 0.000 claims 1
- QDBLQXQPMSKWSP-UHFFFAOYSA-N 2-[[2-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]acetyl]amino]acetic acid Chemical compound CC1=NN(CC(=O)NCC(O)=O)C(C)=C1CC1=CC(C)=C(O)C2=C1CCC2 QDBLQXQPMSKWSP-UHFFFAOYSA-N 0.000 claims 1
- JAPINHQACBOWSD-UHFFFAOYSA-N 2-[[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]methyl]pentanedioic acid Chemical compound CC1=NN(CC(CCC(O)=O)C(O)=O)C(C)=C1CC1=CC(C)=C(O)C2=C1CCC2 JAPINHQACBOWSD-UHFFFAOYSA-N 0.000 claims 1
- CZCNKAVXCPVJFO-UHFFFAOYSA-N 3-[3,5-diethyl-4-[[6-[(4-fluorophenyl)methyl]-7-hydroxy-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]propanoic acid Chemical compound CCC1=NN(CCC(O)=O)C(CC)=C1CC1=CC(CC=2C=CC(F)=CC=2)=C(O)C2=C1CCC2 CZCNKAVXCPVJFO-UHFFFAOYSA-N 0.000 claims 1
- JIHJVKZSHUSXIU-UHFFFAOYSA-N 3-[3,5-diethyl-4-[[7-hydroxy-6-(pyrrolidin-1-ylmethyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]propanoic acid Chemical compound CCC1=NN(CCC(O)=O)C(CC)=C1CC1=CC(CN2CCCC2)=C(O)C2=C1CCC2 JIHJVKZSHUSXIU-UHFFFAOYSA-N 0.000 claims 1
- PYYSLFJQNJVZTL-UHFFFAOYSA-N 3-[3,5-diethyl-4-[[7-hydroxy-6-(pyrrolidine-1-carbonyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]propanoic acid Chemical compound CCC1=NN(CCC(O)=O)C(CC)=C1CC1=CC(C(=O)N2CCCC2)=C(O)C2=C1CCC2 PYYSLFJQNJVZTL-UHFFFAOYSA-N 0.000 claims 1
- ZFJHPYFTLPWQJV-UHFFFAOYSA-N 3-[3,5-diethyl-4-[[7-methoxy-6-(methoxymethyl)-2,3-dihydro-1h-inden-4-yl]methyl]pyrazol-1-yl]propanoic acid Chemical compound CCC1=NN(CCC(O)=O)C(CC)=C1CC1=CC(COC)=C(OC)C2=C1CCC2 ZFJHPYFTLPWQJV-UHFFFAOYSA-N 0.000 claims 1
- SJGIZFVDOCBRAF-UHFFFAOYSA-N 3-[3-ethoxy-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-5-methylpyrazol-1-yl]propanoic acid Chemical compound CCOC1=NN(CCC(O)=O)C(C)=C1CC1=CC(C)=C(OC)C2=C1CCC2 SJGIZFVDOCBRAF-UHFFFAOYSA-N 0.000 claims 1
- BEJUGZWZPSSNPU-UHFFFAOYSA-N 3-[4-(1h-indol-5-ylmethyl)-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1CC1=CC=C(NC=C2)C2=C1 BEJUGZWZPSSNPU-UHFFFAOYSA-N 0.000 claims 1
- QUNPPIPHEBLXLM-UHFFFAOYSA-N 3-[4-(1h-indol-5-yloxy)-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1OC1=CC=C(NC=C2)C2=C1 QUNPPIPHEBLXLM-UHFFFAOYSA-N 0.000 claims 1
- MYGRDZZMHMPNGD-UHFFFAOYSA-N 3-[4-[(6-chloro-7-hydroxy-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1CC1=CC(Cl)=C(O)C2=C1CCC2 MYGRDZZMHMPNGD-UHFFFAOYSA-N 0.000 claims 1
- MTJXZJJMVLFLAL-UHFFFAOYSA-N 3-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1OC1=CC=C(O)C2=C1CCC2 MTJXZJJMVLFLAL-UHFFFAOYSA-N 0.000 claims 1
- RBORKMMEVUNVJB-UHFFFAOYSA-N 3-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3-thiophen-2-ylpyrazol-1-yl]propanoic acid Chemical compound N=1N(CCC(=O)O)C=C(OC=2C=3CCCC=3C(O)=CC=2)C=1C1=CC=CS1 RBORKMMEVUNVJB-UHFFFAOYSA-N 0.000 claims 1
- YYWZKUOEBVIFTQ-UHFFFAOYSA-N 3-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-5-thiophen-2-ylpyrazol-1-yl]propanoic acid Chemical compound OC(=O)CCN1N=CC(OC=2C=3CCCC=3C(O)=CC=2)=C1C1=CC=CS1 YYWZKUOEBVIFTQ-UHFFFAOYSA-N 0.000 claims 1
- APSJGYZKPFIMEN-UHFFFAOYSA-N 3-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-n-(2h-tetrazol-5-yl)propanamide Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CCC(=O)NC1=NN=NN1 APSJGYZKPFIMEN-UHFFFAOYSA-N 0.000 claims 1
- QNGIHSZAUHRDTQ-UHFFFAOYSA-N 3-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-n-propan-2-ylpropanamide Chemical compound CC(C)NC(=O)CCN1N=C(C)C(CC=2C=3CCCC=3C(O)=C(C)C=2)=C1C QNGIHSZAUHRDTQ-UHFFFAOYSA-N 0.000 claims 1
- UUZGJIISKHTLFT-UHFFFAOYSA-N 3-[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1OC1=CC(C)=C(O)C2=C1CCC2 UUZGJIISKHTLFT-UHFFFAOYSA-N 0.000 claims 1
- RVJKZUJNTAIRGU-UHFFFAOYSA-N 3-[4-[(7-hydroxy-6-propan-2-yl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound C=12CCCC2=C(O)C(C(C)C)=CC=1CC=1C(C)=NN(CCC(O)=O)C=1C RVJKZUJNTAIRGU-UHFFFAOYSA-N 0.000 claims 1
- BRXAEONTSSXVKM-UHFFFAOYSA-N 3-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-n-propan-2-ylsulfonylpropanamide Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C)=NN(CCC(=O)NS(=O)(=O)C(C)C)C=1C BRXAEONTSSXVKM-UHFFFAOYSA-N 0.000 claims 1
- LLPFUQDIKDAAIA-UHFFFAOYSA-N 3-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C)=NN(CCC(O)=O)C=1C LLPFUQDIKDAAIA-UHFFFAOYSA-N 0.000 claims 1
- XTEADIOFAZSIQV-UHFFFAOYSA-N 3-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]propanoic acid Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC1=C(C)N(CCC(O)=O)N=C1C(F)(F)F XTEADIOFAZSIQV-UHFFFAOYSA-N 0.000 claims 1
- UIXIHPGQSBMGQR-UHFFFAOYSA-N 3-[4-[[6-[(4-fluorophenyl)methyl]-7-hydroxy-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1CC1=CC(CC=2C=CC(F)=CC=2)=C(O)C2=C1CCC2 UIXIHPGQSBMGQR-UHFFFAOYSA-N 0.000 claims 1
- ZEPAYOGKPHNWEC-UHFFFAOYSA-N 3-[4-[[7-hydroxy-6-[(4-methylphenyl)methyl]-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(C)=C1CC1=CC(CC=2C=CC(C)=CC=2)=C(O)C2=C1CCC2 ZEPAYOGKPHNWEC-UHFFFAOYSA-N 0.000 claims 1
- VPJOQJWVSRLCGS-UHFFFAOYSA-N 3-[4-[[7-methoxy-6-(4-methoxyphenyl)-2,3-dihydro-1h-inden-4-yl]methyl]-3,5-dimethylpyrazol-1-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(CC2=C(N(CCC(O)=O)N=C2C)C)=C(CCC2)C2=C1OC VPJOQJWVSRLCGS-UHFFFAOYSA-N 0.000 claims 1
- OGTKXIMTDRNUID-UHFFFAOYSA-N 3-[5-ethoxy-4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3-methylpyrazol-1-yl]propanoic acid Chemical compound CC1=NN(CCC(O)=O)C(OCC)=C1CC1=CC(C)=C(OC)C2=C1CCC2 OGTKXIMTDRNUID-UHFFFAOYSA-N 0.000 claims 1
- OHJGXGQFPMRLAJ-UHFFFAOYSA-N 3-[[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]methyl]-2h-1,2,4-oxadiazol-5-one Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC1=NOC(O)=N1 OHJGXGQFPMRLAJ-UHFFFAOYSA-N 0.000 claims 1
- QKHUDUSTKPSFDL-UHFFFAOYSA-N 5-[[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]methyl]-3h-1,3,4-oxadiazol-2-one Chemical compound CCC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(CC)=NN1CC1=NNC(=O)O1 QKHUDUSTKPSFDL-UHFFFAOYSA-N 0.000 claims 1
- LRJKWGNURXCSEC-UHFFFAOYSA-N 5-[[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]methyl]-1,2-dihydropyrazol-3-one Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC1=CC(O)=NN1 LRJKWGNURXCSEC-UHFFFAOYSA-N 0.000 claims 1
- UWCVVRCCMCHLBK-UHFFFAOYSA-N 5-[[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]methyl]-3h-1,3,4-oxadiazol-2-one Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC1=NNC(=O)O1 UWCVVRCCMCHLBK-UHFFFAOYSA-N 0.000 claims 1
- ZHQDOYWFOBWDAN-UHFFFAOYSA-N 6-[[4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]methyl]-2-methyl-1h-pyrimidin-4-one Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC1=CC(=O)NC(C)=N1 ZHQDOYWFOBWDAN-UHFFFAOYSA-N 0.000 claims 1
- DWWKYGYRNOPDEI-UHFFFAOYSA-N 7-[(1-benzyl-3,5-dimethylpyrazol-4-yl)methyl]-5-methyl-2,3-dihydro-1h-inden-4-ol Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CC1=CC=CC=C1 DWWKYGYRNOPDEI-UHFFFAOYSA-N 0.000 claims 1
- LQSJZJCFELWACK-UHFFFAOYSA-N 7-[3,5-dimethyl-1-(2h-tetrazol-5-ylmethyl)pyrazol-4-yl]oxy-2,3-dihydro-1h-inden-4-ol Chemical compound CC1=C(OC=2C=3CCCC=3C(O)=CC=2)C(C)=NN1CC1=NN=NN1 LQSJZJCFELWACK-UHFFFAOYSA-N 0.000 claims 1
- OGMMRVHFXKSHAP-UHFFFAOYSA-N 7-[3,5-dimethyl-1-[2-(2h-tetrazol-5-yl)ethyl]pyrazol-4-yl]oxy-2,3-dihydro-1h-inden-4-ol Chemical compound CC1=C(OC=2C=3CCCC=3C(O)=CC=2)C(C)=NN1CCC1=NN=NN1 OGMMRVHFXKSHAP-UHFFFAOYSA-N 0.000 claims 1
- IXXLPLGIGCSMGV-UHFFFAOYSA-N 7-[[3,5-dimethyl-1-[2-(2h-tetrazol-5-yl)ethyl]pyrazol-4-yl]methyl]-5-methyl-2,3-dihydro-1h-inden-4-ol Chemical compound CC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(C)=NN1CCC1=NN=NN1 IXXLPLGIGCSMGV-UHFFFAOYSA-N 0.000 claims 1
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- OBPXNRIDEWUYKX-UHFFFAOYSA-N [4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-morpholin-4-ylmethanone Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC(=C1C)C(C)=NN1C(=O)N1CCOCC1 OBPXNRIDEWUYKX-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- PEAGZHAKMWIATF-UHFFFAOYSA-N ethyl 2-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)N1N=C(C)C(CC=2C=3CCCC=3C(OC)=C(C)C=2)=C1C PEAGZHAKMWIATF-UHFFFAOYSA-N 0.000 claims 1
- XWMCOBVVCNLYQB-UHFFFAOYSA-N ethyl 3-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)N1N=C(C)C(CC=2C=3CCCC=3C(OC)=C(C)C=2)=C1C XWMCOBVVCNLYQB-UHFFFAOYSA-N 0.000 claims 1
- RXARVZRPEKCMGS-UHFFFAOYSA-N ethyl 4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazole-1-carboxylate Chemical compound CCOC(=O)N1N=C(C)C(CC=2C=3CCCC=3C(OC)=C(C)C=2)=C1C RXARVZRPEKCMGS-UHFFFAOYSA-N 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004898 mitochondrial function Effects 0.000 claims 1
- CPXBJVOHYUFYIZ-UHFFFAOYSA-N n'-hydroxy-2-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]ethanimidamide Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C)=NN(CC(=N)NO)C=1C CPXBJVOHYUFYIZ-UHFFFAOYSA-N 0.000 claims 1
- PAMBKMZFIMLHPS-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[3,5-diethyl-4-[(7-hydroxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]pyrazol-1-yl]acetamide Chemical compound CCC1=C(CC=2C=3CCCC=3C(O)=C(C)C=2)C(CC)=NN1CC(=O)NC1=CC=C(Cl)C=C1 PAMBKMZFIMLHPS-UHFFFAOYSA-N 0.000 claims 1
- RWKCMCNHGAYDIQ-UHFFFAOYSA-N n-[2-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]ethyl]acetamide Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C)=NN(CCNC(C)=O)C=1C RWKCMCNHGAYDIQ-UHFFFAOYSA-N 0.000 claims 1
- CSOVHYZQYZYLGJ-UHFFFAOYSA-N n-[2-[4-[(7-methoxy-6-methyl-2,3-dihydro-1h-inden-4-yl)methyl]-3,5-dimethylpyrazol-1-yl]ethyl]methanesulfonamide Chemical compound C1=C(C)C(OC)=C2CCCC2=C1CC=1C(C)=NN(CCNS(C)(=O)=O)C=1C CSOVHYZQYZYLGJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/06—Antihyperlipidemics
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- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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IN857KO2007 | 2007-06-06 | ||
PCT/IN2008/000345 WO2008149379A2 (en) | 2007-06-06 | 2008-06-02 | Novel compounds |
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US (2) | US8143424B2 (ja) |
EP (1) | EP2061766B1 (ja) |
JP (1) | JP5243537B2 (ja) |
KR (1) | KR101152965B1 (ja) |
CN (1) | CN101772487B (ja) |
AR (1) | AR066155A1 (ja) |
AT (1) | ATE478053T1 (ja) |
AU (1) | AU2008259314B2 (ja) |
CA (1) | CA2698704C (ja) |
CY (1) | CY1110925T1 (ja) |
DE (1) | DE602008002205D1 (ja) |
DK (1) | DK2061766T3 (ja) |
EA (1) | EA019084B1 (ja) |
ES (1) | ES2351274T3 (ja) |
HK (1) | HK1129221A1 (ja) |
HR (1) | HRP20100611T1 (ja) |
IL (1) | IL202515A (ja) |
MX (1) | MX2009013070A (ja) |
NZ (1) | NZ582273A (ja) |
PL (1) | PL2061766T3 (ja) |
PT (1) | PT2061766E (ja) |
RS (1) | RS51501B (ja) |
SI (1) | SI2061766T1 (ja) |
TW (1) | TWI360541B (ja) |
UA (1) | UA98962C2 (ja) |
WO (1) | WO2008149379A2 (ja) |
ZA (1) | ZA200908760B (ja) |
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BR112012025343A2 (pt) * | 2010-04-15 | 2016-06-28 | Merck Patent Gmbh | processo para a preparação de hidroquinonas |
EP2566333A4 (en) * | 2010-05-07 | 2014-04-02 | Univ Leland Stanford Junior | IDENTIFICATION OF STABILIZERS OF MULTIMEDER PROTEINS |
MY170520A (en) | 2012-09-17 | 2019-08-08 | Madrigal Pharmaceuticals Inc | Method of synthesizing thyroid hormone analogs and polymorphs thereof |
CN105530923B (zh) * | 2013-09-09 | 2019-07-23 | 佩洛通治疗公司 | 芳基醚及其用途 |
US9884843B2 (en) | 2013-12-16 | 2018-02-06 | Peloton Therapeutics, Inc. | Cyclic sulfone and sulfoximine analogs and uses thereof |
CN103992225B (zh) * | 2014-03-26 | 2016-01-13 | 安徽师范大学 | 一种水杨醛衍生物及其制备方法 |
JP6543342B2 (ja) | 2014-08-14 | 2019-07-10 | アルハマドシャー,マモウン,エム. | 血清半減期を延長するための、調節可能リンカーを介した薬学的活性剤とトランスサイレチンリガンドのコンジュゲーション |
WO2016066664A1 (en) * | 2014-10-31 | 2016-05-06 | F. Hoffmann-La Roche Ag | New pyridinyloxy- and phenyloxy-pyrazolyl compounds |
WO2016144826A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
WO2016145032A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
US10512626B2 (en) | 2015-03-11 | 2019-12-24 | Peloton Therapeautics, Inc. | Compositions for use in treating glioblastoma |
WO2016144825A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
US10335388B2 (en) | 2015-04-17 | 2019-07-02 | Peloton Therapeutics, Inc. | Combination therapy of a HIF-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
US20180230103A1 (en) * | 2015-11-16 | 2018-08-16 | Lonza Ltd | Method for preparation of 1-methyl-3-(trifluoromethyl)-1h-pyrazol-5-ol |
RU2621163C1 (ru) * | 2016-02-16 | 2017-05-31 | государственное бюджетное образовательное учреждение высшего профессионального образования "Сибирский государственный медицинский университет" Министерства здравоохранения Российской Федерации (ГБОУ ВПО СибГМУ Минздрава России) | Антифибролитическое средство |
JP2019533019A (ja) | 2016-10-18 | 2019-11-14 | マドリガル ファーマシューティカルズ インコーポレイテッドMadrigal Pharmaceuticals,Inc. | Thr−ベータアゴニストで肝臓障害又は脂質障害を治療する方法 |
MA47511A (fr) | 2017-02-17 | 2019-12-25 | Eidos Therapeutics Inc | Procédés de préparation d'ag-10, de ses intermédiaires et de sels correspondants |
EP3768841A4 (en) | 2018-03-23 | 2021-12-08 | Eidos Therapeutics, Inc. | METHODS OF TREATING TTR AMYLOSIS USING AG10 |
BR112020026493A2 (pt) | 2018-08-17 | 2021-03-23 | Eidos Therapeutics, Inc. | Formulações de ag10 |
KR20210064310A (ko) * | 2018-09-22 | 2021-06-02 | 토렌트 파마슈티칼스 리미티드 | 피라졸 화합물의 제조 방법 |
WO2020175957A1 (ko) * | 2019-02-28 | 2020-09-03 | 주식회사 마더스제약 | 피라졸 아마이드 유도체 화합물 및 이의 용도 |
WO2023047203A1 (en) | 2021-09-25 | 2023-03-30 | Torrent Pharmaceuticals Ltd | Combination of omzotirome and antidiabetic agent, antihypertensive agent or anti-dyslipidemic agent |
WO2023164536A1 (en) * | 2022-02-23 | 2023-08-31 | Biohaven Therapeutics Ltd. | Pyrazolyl compounds as kv7 channel activators |
WO2023164537A1 (en) * | 2022-02-23 | 2023-08-31 | Biohaven Therapeutics Ltd. | Pyrazolyl compounds as kv7 channel activators |
WO2023164538A1 (en) * | 2022-02-23 | 2023-08-31 | Biohaven Therapeutics Ltd. | Pyrazolyl compounds as kv7 channel activators |
CN114920635B (zh) * | 2022-04-29 | 2023-05-12 | 郑州原理医药研究院有限公司 | 4-羟基-1-茚酮的制备方法 |
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WO2024089191A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Microbiocidal heterobicyclic dihydrooxadiazine derivatives |
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AU7598596A (en) | 1995-11-01 | 1997-05-22 | Allergan, Inc. | Sulfides, sulfoxides and sulfones disubstituted with a tetrahydronaphthalenyl, chromanyl, thiochromanyl or tetrahydroquinolinyl and substituted phenyl or heteroaryl group, having retinoid-like biological activity |
ATE250573T1 (de) | 1997-02-25 | 2003-10-15 | Akzo Nobel Nv | Azetidin- und pyrrolidinderivate |
CA2321188C (en) | 1998-02-26 | 2008-04-29 | Akzo Nobel N.V. | Derivatives of azetidine and pyrrolidine |
US6240678B1 (en) | 1998-07-09 | 2001-06-05 | Karl Heinz Spether | Capping head with torque adjustment |
DE60012700T2 (de) | 1999-03-01 | 2005-07-28 | Pfizer Products Inc., Groton | Oxamsäure und deren derivate als liganden der thyroid-rezeptoren |
AR018470A1 (es) | 1999-06-01 | 2001-11-14 | Procter & Gamble | Metodo para el tratamiento de la perdida del cabello con un compuesto que no afecta el corazon |
EP1127882A1 (en) | 2000-01-25 | 2001-08-29 | Pfizer Products Inc. | Tetrazole compounds as thyroid receptor ligands |
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US7230025B2 (en) | 2002-09-26 | 2007-06-12 | Pfizer, Inc. | Pyrazole derivatives |
ITRM20030363A1 (it) * | 2003-07-24 | 2005-01-25 | Fernando Goglia | Composizioni comprendenti la 3, 5diiodotironina e uso farmaceutico di esse. |
WO2006128056A2 (en) | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Novel phosphinic acid-containing thyromimetics |
GB0513692D0 (en) * | 2005-07-04 | 2005-08-10 | Karobio Ab | Novel pharmaceutical compositions |
JP5000649B2 (ja) | 2005-07-21 | 2012-08-15 | エフ.ホフマン−ラ ロシュ アーゲー | 甲状腺ホルモン受容体アゴニストとしてのピリダジノン誘導体 |
CA2620425A1 (en) | 2005-08-31 | 2007-03-08 | Bayer Healthcare Llc | Anilinopyrazole derivatives useful for the treatment of diabetes |
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