ES2334574T3 - Compuestos de tipo hidrazida y su uso en unas composiciones farmaceuticas para el tratamiento de las enfermedades cardiovasculares. - Google Patents
Compuestos de tipo hidrazida y su uso en unas composiciones farmaceuticas para el tratamiento de las enfermedades cardiovasculares. Download PDFInfo
- Publication number
- ES2334574T3 ES2334574T3 ES05717518T ES05717518T ES2334574T3 ES 2334574 T3 ES2334574 T3 ES 2334574T3 ES 05717518 T ES05717518 T ES 05717518T ES 05717518 T ES05717518 T ES 05717518T ES 2334574 T3 ES2334574 T3 ES 2334574T3
- Authority
- ES
- Spain
- Prior art keywords
- atom
- group
- formula
- radical
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 90
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 208000024172 Cardiovascular disease Diseases 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 43
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 150000002632 lipids Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WIIROLNZSHKQBP-VXLYETTFSA-N N-[(E)-(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]-1-benzothiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(O)=C1\C=N\NC(=O)C1=CC2=CC=CC=C2S1 WIIROLNZSHKQBP-VXLYETTFSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000006806 disease prevention Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 150000003463 sulfur Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 206010051113 Arterial restenosis Diseases 0.000 claims description 2
- 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 2
- BJDIXEJPIMNAAO-UHFFFAOYSA-N N-[(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]furan-2-carboxamide Chemical compound COC1=CC(OC)=CC(O)=C1C=NNC(=O)C1=CC=CO1 BJDIXEJPIMNAAO-UHFFFAOYSA-N 0.000 claims description 2
- XPRGQFQLEOSLLX-LZYBPNLTSA-N N-[(E)-(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]-5-methylthiophene-2-carboxamide Chemical compound COC1=CC(OC)=CC(O)=C1\C=N\NC(=O)C1=CC=C(C)S1 XPRGQFQLEOSLLX-LZYBPNLTSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- OTZZLFLYYBVBKH-XIBKSJEISA-N chembl1999456 Chemical compound OC1=C(Br)C=C(Br)C=C1\C=N/NC(=O)CSCC(=O)N\N=C/C1=CC(Br)=CC(Br)=C1O OTZZLFLYYBVBKH-XIBKSJEISA-N 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 208000006132 lipodystrophy Diseases 0.000 claims description 2
- 230000004060 metabolic process Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 22
- 102000004895 Lipoproteins Human genes 0.000 abstract description 13
- 108090001030 Lipoproteins Proteins 0.000 abstract description 13
- 238000009825 accumulation Methods 0.000 abstract description 13
- 150000003839 salts Chemical class 0.000 abstract description 8
- 101001074035 Homo sapiens Zinc finger protein GLI2 Proteins 0.000 abstract description 7
- 102100035558 Zinc finger protein GLI2 Human genes 0.000 abstract description 7
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- GZAMHVSGBNTFCB-UHFFFAOYSA-N 2-cyclopropyl-N-[(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]quinoline-4-carboxamide Chemical compound COC1=CC(OC)=CC(O)=C1C=NNC(=O)C1=CC(C2CC2)=NC2=CC=CC=C12 GZAMHVSGBNTFCB-UHFFFAOYSA-N 0.000 abstract 2
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 230000002402 anti-lipaemic effect Effects 0.000 abstract 1
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- 230000001966 cerebroprotective effect Effects 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 230000001553 hepatotropic effect Effects 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000003367 polycyclic group Polymers 0.000 abstract 1
- 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 description 86
- 241000699670 Mus sp. Species 0.000 description 44
- 235000012000 cholesterol Nutrition 0.000 description 42
- 235000005911 diet Nutrition 0.000 description 33
- 230000037213 diet Effects 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 23
- 102000013918 Apolipoproteins E Human genes 0.000 description 19
- 108010025628 Apolipoproteins E Proteins 0.000 description 19
- 241000700159 Rattus Species 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 15
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 15
- 239000005715 Fructose Substances 0.000 description 14
- 229930091371 Fructose Natural products 0.000 description 13
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 13
- 150000003626 triacylglycerols Chemical class 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 11
- 210000002540 macrophage Anatomy 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000005259 measurement Methods 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 229940125396 insulin Drugs 0.000 description 8
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 8
- 102000004877 Insulin Human genes 0.000 description 7
- 108090001061 Insulin Proteins 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 229960003105 metformin Drugs 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 230000002526 effect on cardiovascular system Effects 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 208000032928 Dyslipidaemia Diseases 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 108010010234 HDL Lipoproteins Proteins 0.000 description 5
- 102000015779 HDL Lipoproteins Human genes 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 210000000709 aorta Anatomy 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 235000021590 normal diet Nutrition 0.000 description 5
- 238000011552 rat model Methods 0.000 description 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 4
- 210000000579 abdominal fat Anatomy 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000004060 quinone imines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 108010089254 Cholesterol oxidase Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 102000003992 Peroxidases Human genes 0.000 description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 3
- 230000000923 atherogenic effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002224 dissection Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002466 imines Chemical group 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 108040007629 peroxidase activity proteins Proteins 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- PRDFBSVERLRRMY-UHFFFAOYSA-N 2'-(4-ethoxyphenyl)-5-(4-methylpiperazin-1-yl)-2,5'-bibenzimidazole Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CC=C(C=3NC4=CC(=CC=C4N=3)N3CCN(C)CC3)C=C2N1 PRDFBSVERLRRMY-UHFFFAOYSA-N 0.000 description 2
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
- 206010003178 Arterial thrombosis Diseases 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- 102000049320 CD36 Human genes 0.000 description 2
- 108010045374 CD36 Antigens Proteins 0.000 description 2
- 101100168093 Caenorhabditis elegans cogc-2 gene Proteins 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- 101100055876 Mus musculus Apoe gene Proteins 0.000 description 2
- 101100221487 Mus musculus Cog2 gene Proteins 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000012980 RPMI-1640 medium Substances 0.000 description 2
- 108010055297 Sterol Esterase Proteins 0.000 description 2
- 102000000019 Sterol Esterase Human genes 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 230000007214 atherothrombosis Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 2
- 229960000815 ezetimibe Drugs 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 231100000304 hepatotoxicity Toxicity 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 230000007056 liver toxicity Effects 0.000 description 2
- 102000006240 membrane receptors Human genes 0.000 description 2
- 108020004084 membrane receptors Proteins 0.000 description 2
- 208000030159 metabolic disease Diseases 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 2
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 101150037123 APOE gene Proteins 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- 206010000077 Abdominal mass Diseases 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 102000005862 Angiotensin II Human genes 0.000 description 1
- 101800000733 Angiotensin-2 Proteins 0.000 description 1
- 102100029470 Apolipoprotein E Human genes 0.000 description 1
- 101710095339 Apolipoprotein E Proteins 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 210000003771 C cell Anatomy 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 108010004103 Chylomicrons Proteins 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 206010015548 Euthanasia Diseases 0.000 description 1
- 101100226596 Gallus gallus FABP gene Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- NPGIHFRTRXVWOY-UHFFFAOYSA-N Oil red O Chemical compound Cc1ccc(C)c(c1)N=Nc1cc(C)c(cc1C)N=Nc1c(O)ccc2ccccc12 NPGIHFRTRXVWOY-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000012891 Ringer solution Substances 0.000 description 1
- 101100379247 Salmo trutta apoa1 gene Proteins 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000008578 acute process Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 229940127217 antithrombotic drug Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 231100001012 cardiac lesion Toxicity 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-4-en-3-one Chemical compound C1CC2=CC(=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 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 210000000497 foam cell Anatomy 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000007654 ischemic lesion Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 108010022197 lipoprotein cholesterol Proteins 0.000 description 1
- 230000008604 lipoprotein metabolism Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960004329 metformin hydrochloride Drugs 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- 210000002824 peroxisome Anatomy 0.000 description 1
- 239000007971 pharmaceutical suspension Substances 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000009862 primary prevention Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0400913A FR2865732B1 (fr) | 2004-01-30 | 2004-01-30 | Composes de type hydrazide et leur utilisation dans des compositions pharmaceutiques pour le traitement des maladies cardiovasculaires |
| FR0400913 | 2004-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2334574T3 true ES2334574T3 (es) | 2010-03-12 |
Family
ID=34746342
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05717518T Expired - Lifetime ES2334574T3 (es) | 2004-01-30 | 2005-01-31 | Compuestos de tipo hidrazida y su uso en unas composiciones farmaceuticas para el tratamiento de las enfermedades cardiovasculares. |
| ES09166657T Expired - Lifetime ES2398479T3 (es) | 2004-01-30 | 2005-01-31 | Compuestos de tipo hidrazida y su uso en unas composiciones farmacéuticas para el tratamiento de las enfermedades cardiovasculares |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09166657T Expired - Lifetime ES2398479T3 (es) | 2004-01-30 | 2005-01-31 | Compuestos de tipo hidrazida y su uso en unas composiciones farmacéuticas para el tratamiento de las enfermedades cardiovasculares |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20070161697A1 (https=) |
| EP (2) | EP1709027B1 (https=) |
| JP (1) | JP5047629B2 (https=) |
| CN (1) | CN100588655C (https=) |
| AT (1) | ATE444961T1 (https=) |
| AU (1) | AU2005217174B2 (https=) |
| BR (1) | BRPI0507248A (https=) |
| CA (1) | CA2554439A1 (https=) |
| DE (1) | DE602005017007D1 (https=) |
| DK (1) | DK2113502T3 (https=) |
| ES (2) | ES2334574T3 (https=) |
| FR (1) | FR2865732B1 (https=) |
| PT (2) | PT1709027E (https=) |
| WO (1) | WO2005082882A1 (https=) |
| ZA (1) | ZA200606909B (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006132583A1 (en) * | 2005-06-07 | 2006-12-14 | Innate Pharmaceuticals Ab | Method and means for preventing and inhibiting respiratory disease, atherosclerosis and osteoporosis caused by chlamydia pneumoniae infection |
| EP2338879A1 (en) | 2009-12-15 | 2011-06-29 | Arteria | New phenylhydrazone derivatives and their use as pharmaceuticals |
| WO2012027548A1 (en) * | 2010-08-25 | 2012-03-01 | The Feinstein Institute For Medical Research | Compounds and methods for prevention and treatment of alzheimer's and other diseases |
| CN103044284A (zh) * | 2011-10-13 | 2013-04-17 | 南京大学 | 香草酸酰腙类衍生物及其制备和用途 |
| WO2014028946A2 (en) * | 2012-08-17 | 2014-02-20 | The Broad Institute, Inc. | Modulators of hepatic lipoprotein metabolism |
| CN103613514B (zh) * | 2013-10-30 | 2015-05-13 | 西北师范大学 | 荧光比色识别氰根离子的有机双金属凝胶及其制备和应用 |
| CN104860866B (zh) * | 2015-05-25 | 2018-07-17 | 厦门大学 | 5-(取代碳酰氨基)-1h-吲哚-2-碳酰肼衍生物及其制备方法和应用 |
| CN104829597B (zh) * | 2015-05-25 | 2018-07-17 | 厦门大学 | 1h-吲哚-2-碳酰肼衍生物及其制备方法和用途 |
| CN105348170B (zh) * | 2015-11-06 | 2019-02-05 | 厦门大学 | 1-(2-(碳酰肼取代基团)-1h-吲哚-5-基)-3-取代脲衍生物及制备方法 |
| AU2017375687B2 (en) | 2016-09-26 | 2023-09-14 | Qingdao Primedicine Pharmaceutical Co., Ltd. | N-methyl-D-aspartate receptor allosteric modulators and methods for their use |
| PL233208B1 (pl) * | 2018-09-17 | 2019-09-30 | Politechnika Wroclawska | Iminowe pochodne aldehydów salicylowych i hydrazydu kwasu 4-hydroksybenzoesowego oraz sposób ich wytwarzania |
| WO2023060161A1 (en) * | 2021-10-06 | 2023-04-13 | The Research Foundation For The State University Of New York | Anti-fungals compounds targeting the synthesis of fungal sphingolipids |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB762187A (en) * | 1952-10-09 | 1956-11-28 | Bayer Ag | Metal complexes of hydrazide-hydrazones and process for producing the same |
| JPS4819628B1 (https=) * | 1969-01-07 | 1973-06-14 | ||
| US3859281A (en) * | 1971-07-01 | 1975-01-07 | American Home Prod | 2,6-dichlorobenzylidenehydrazides |
| US3829492A (en) * | 1972-02-04 | 1974-08-13 | Rohm & Haas | Fungicidal salicylaldehyde hydrazones and azines |
| US3963480A (en) * | 1973-04-11 | 1976-06-15 | Sterling Drug Inc. | Herbicidal pyrrole-2-carboxamides |
| JPS62501709A (ja) * | 1985-02-11 | 1987-07-09 | ジ・アップジョン・カンパニ− | 駆虫薬ピリジニル・アシルヒドラゾン、その使用方法および組成物 |
| US5424333A (en) * | 1985-10-21 | 1995-06-13 | Rohm And Haas Company | Anthelmintic N'-substituted-N,N'-disubstitutedhydrazines |
| US6005113A (en) * | 1996-05-15 | 1999-12-21 | Molecular Probes, Inc. | Long wavelength dyes for infrared tracing |
| JPH11106371A (ja) * | 1997-07-04 | 1999-04-20 | Nisshin Flour Milling Co Ltd | アシルヒドラゾン誘導体 |
| JP2001233767A (ja) * | 2000-02-25 | 2001-08-28 | Shionogi & Co Ltd | アポａｉ発現亢進剤 |
| US20020128292A1 (en) * | 2000-12-07 | 2002-09-12 | Cai Sui Xiong | Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| JP2004525118A (ja) * | 2001-01-22 | 2004-08-19 | アルパイダ アーゲー | 新規ヒドラゾン類 |
| DE20108608U1 (de) * | 2001-05-23 | 2001-08-09 | Wella Ag, 64295 Darmstadt | 2,5-Diamino-benzaldehyd-Derivate und diese Verbindungen enthaltende Färbemittel |
| EP1462105A1 (en) * | 2003-03-28 | 2004-09-29 | Procorde GmbH | Activation specific inhibitors of NF-kB and method of treating inflammatory processes in cardio-vascular diseases |
| DE10348022A1 (de) * | 2003-10-15 | 2005-05-25 | Imtm Gmbh | Neue Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| CA2653787C (en) * | 2006-05-31 | 2016-06-21 | Mochida Pharmaceutical Co., Ltd. | Composition for preventing the occurrence of cardiovascular event in multiple risk patient |
-
2004
- 2004-01-30 FR FR0400913A patent/FR2865732B1/fr not_active Expired - Fee Related
-
2005
- 2005-01-31 PT PT05717518T patent/PT1709027E/pt unknown
- 2005-01-31 CN CN200580009749A patent/CN100588655C/zh not_active Expired - Fee Related
- 2005-01-31 ZA ZA200606909A patent/ZA200606909B/en unknown
- 2005-01-31 AU AU2005217174A patent/AU2005217174B2/en not_active Ceased
- 2005-01-31 US US10/587,697 patent/US20070161697A1/en not_active Abandoned
- 2005-01-31 ES ES05717518T patent/ES2334574T3/es not_active Expired - Lifetime
- 2005-01-31 BR BRPI0507248-4A patent/BRPI0507248A/pt not_active IP Right Cessation
- 2005-01-31 DE DE602005017007T patent/DE602005017007D1/de not_active Expired - Lifetime
- 2005-01-31 JP JP2006550247A patent/JP5047629B2/ja not_active Expired - Fee Related
- 2005-01-31 AT AT05717518T patent/ATE444961T1/de not_active IP Right Cessation
- 2005-01-31 CA CA002554439A patent/CA2554439A1/fr not_active Abandoned
- 2005-01-31 ES ES09166657T patent/ES2398479T3/es not_active Expired - Lifetime
- 2005-01-31 PT PT91666578T patent/PT2113502E/pt unknown
- 2005-01-31 WO PCT/FR2005/000199 patent/WO2005082882A1/fr not_active Ceased
- 2005-01-31 EP EP05717518A patent/EP1709027B1/fr not_active Expired - Lifetime
- 2005-01-31 EP EP09166657A patent/EP2113502B1/fr not_active Expired - Lifetime
- 2005-01-31 DK DK09166657.8T patent/DK2113502T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200606909B (en) | 2007-12-27 |
| EP1709027B1 (fr) | 2009-10-07 |
| ATE444961T1 (de) | 2009-10-15 |
| EP2113502A1 (fr) | 2009-11-04 |
| ES2398479T3 (es) | 2013-03-19 |
| EP1709027A1 (fr) | 2006-10-11 |
| DE602005017007D1 (de) | 2009-11-19 |
| CA2554439A1 (fr) | 2005-09-09 |
| WO2005082882A1 (fr) | 2005-09-09 |
| FR2865732B1 (fr) | 2007-10-12 |
| EP2113502B1 (fr) | 2012-11-14 |
| AU2005217174A1 (en) | 2005-09-09 |
| DK2113502T3 (da) | 2013-02-18 |
| AU2005217174B2 (en) | 2010-04-01 |
| FR2865732A1 (fr) | 2005-08-05 |
| JP5047629B2 (ja) | 2012-10-10 |
| CN1950356A (zh) | 2007-04-18 |
| BRPI0507248A (pt) | 2007-06-26 |
| PT1709027E (pt) | 2010-01-13 |
| US20070161697A1 (en) | 2007-07-12 |
| JP2007519691A (ja) | 2007-07-19 |
| CN100588655C (zh) | 2010-02-10 |
| PT2113502E (pt) | 2013-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4316794B2 (ja) | イソキノリン誘導体及び医薬 | |
| ES2334574T3 (es) | Compuestos de tipo hidrazida y su uso en unas composiciones farmaceuticas para el tratamiento de las enfermedades cardiovasculares. | |
| BR112012007828B1 (pt) | compostos inibidores da xantina oxidase, processo para preparar os compostos, e, composição farmacêutica para a inibição da xantina oxidase | |
| CN102216316A (zh) | 取代胺衍生物及以其为有效成分的药物组合物 | |
| EP3441389B1 (en) | Pyrazole-oxazolidinone compound for anti-hepatitis b virus | |
| AU2982701A (en) | Diazepan derivatives or salts thereof | |
| Huang et al. | Identification of novel uracil derivatives incorporating benzoic acid moieties as highly potent Dipeptidyl Peptidase-IV inhibitors | |
| ES2782357T3 (es) | Inhibidores de IRE 1 alfa | |
| WO2005021486A1 (ja) | エステル誘導体及びその医薬用途 | |
| JP2003183254A (ja) | ２−アシルアミノ−３，５−ジシアノピリジン誘導体又はその塩 | |
| MX2008000875A (es) | Compuestos farmaceuticos novedosos. | |
| JP6231621B2 (ja) | 新規ベンゾアゼピン誘導体及びその医薬用途 | |
| EP2917204B1 (fr) | Derives de 1h-indole-3-carboxamide et leurs utilisation comme antagonistes du p2y12 | |
| JPH0753500A (ja) | グアニジノ安息香酸誘導体及びこれらを有効成分とする蛋白分解酵素阻害剤 | |
| WO2006093339A1 (ja) | シンナモイル化合物の用途 | |
| WO2006100922A1 (ja) | シンナモイル化合物及びその用途 | |
| CN114401948A (zh) | 用于改善认知功能和对抗物质成瘾的噻唑和二苯基取代的亚砜 | |
| JP2023506321A (ja) | 心臓病の治療のための心筋細胞増殖活性を有する複素環式誘導体の使用 | |
| PT1535612E (pt) | Tratamento da hiperuricemia | |
| TWI643847B (zh) | Novel benzoazepine derivatives and their medical uses | |
| US4628057A (en) | Tetrahydro-β-carboline derivatives and treatment of liver diseases | |
| WO2008140214A1 (en) | Use of aminothiophene derivative for preventing or treating ischemic diseases | |
| EP3929184A1 (en) | ((((3-halophenyl)(phenyl)methyl)sulfinyl)methyl)thiophene compounds and diastereomeric forms thereof for use in improving cognitive functions | |
| TW202235408A (zh) | 化合物 | |
| CN119421881A (zh) | 酯类化合物及其应用 |