RU2564661C2 - Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ - Google Patents
Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ Download PDFInfo
- Publication number
- RU2564661C2 RU2564661C2 RU2012129930/04A RU2012129930A RU2564661C2 RU 2564661 C2 RU2564661 C2 RU 2564661C2 RU 2012129930/04 A RU2012129930/04 A RU 2012129930/04A RU 2012129930 A RU2012129930 A RU 2012129930A RU 2564661 C2 RU2564661 C2 RU 2564661C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- compound
- alkyl
- mmol
- formula
- Prior art date
Links
- 150000001467 thiazolidinediones Chemical class 0.000 title abstract description 9
- 208000030159 metabolic disease Diseases 0.000 title abstract description 7
- 101150014691 PPARA gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 293
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 24
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 13
- 229940126062 Compound A Drugs 0.000 claims description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 16
- 239000000126 substance Substances 0.000 abstract description 16
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 12
- 208000008589 Obesity Diseases 0.000 abstract description 10
- 235000020824 obesity Nutrition 0.000 abstract description 10
- 230000004770 neurodegeneration Effects 0.000 abstract description 6
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 6
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
- -1 methoxy, ethoxy Chemical group 0.000 description 121
- 125000001931 aliphatic group Chemical group 0.000 description 108
- 125000000217 alkyl group Chemical group 0.000 description 100
- 235000002639 sodium chloride Nutrition 0.000 description 91
- 150000003839 salts Chemical class 0.000 description 77
- 239000000243 solution Substances 0.000 description 73
- 125000001072 heteroaryl group Chemical group 0.000 description 72
- 235000019439 ethyl acetate Nutrition 0.000 description 71
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 125000003118 aryl group Chemical group 0.000 description 61
- 239000011541 reaction mixture Substances 0.000 description 59
- 125000003545 alkoxy group Chemical group 0.000 description 54
- 239000000203 mixture Substances 0.000 description 54
- 229910052736 halogen Inorganic materials 0.000 description 48
- 150000002367 halogens Chemical class 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 45
- 239000011734 sodium Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- 238000002360 preparation method Methods 0.000 description 39
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 37
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 34
- 108010016731 PPAR gamma Proteins 0.000 description 32
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 32
- 239000012267 brine Substances 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 30
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- 125000004043 oxo group Chemical group O=* 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 21
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 19
- 229910004373 HOAc Inorganic materials 0.000 description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 19
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- 125000003368 amide group Chemical group 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 125000002619 bicyclic group Chemical group 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 229960001948 caffeine Drugs 0.000 description 14
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 125000002252 acyl group Chemical group 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000004913 activation Effects 0.000 description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
- 125000003435 aroyl group Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 125000004104 aryloxy group Chemical group 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
- YAUMOGALQJYOJQ-UHFFFAOYSA-N 5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC(C(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 YAUMOGALQJYOJQ-UHFFFAOYSA-N 0.000 description 10
- IRNJSRAGRIZIHD-UHFFFAOYSA-N 5-[[4-[2-(5-ethyl-2-pyridinyl)-2-oxoethoxy]phenyl]methyl]thiazolidine-2,4-dione Chemical compound N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 IRNJSRAGRIZIHD-UHFFFAOYSA-N 0.000 description 10
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- 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 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000012258 stirred mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 8
- 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 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 108020001756 ligand binding domains Proteins 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 229940124597 therapeutic agent Drugs 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
- 0 OC(C(Cc(cc1)ccc1OC*c1cc(C(F)(F)F)ccc1)S1)NC1=O Chemical compound OC(C(Cc(cc1)ccc1OC*c1cc(C(F)(F)F)ccc1)S1)NC1=O 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 230000002860 competitive effect Effects 0.000 description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 5
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229960004586 rosiglitazone Drugs 0.000 description 5
- 239000007909 solid dosage form Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000006172 buffering agent Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 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 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229960005095 pioglitazone Drugs 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000159 protein binding assay Methods 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 4
- RLRHEMOZZVFTOC-UHFFFAOYSA-N 5-[[4-[2-(3-chlorophenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound ClC1=CC=CC(C(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 RLRHEMOZZVFTOC-UHFFFAOYSA-N 0.000 description 3
- MMVHXECWPUECHM-UHFFFAOYSA-N 5-[[4-[2-(3-fluorophenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound FC1=CC=CC(C(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 MMVHXECWPUECHM-UHFFFAOYSA-N 0.000 description 3
- VHVXWJDPJASGLJ-UHFFFAOYSA-N 5-[[4-[2-(4-fluorophenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 VHVXWJDPJASGLJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- JMNFLHLUKPBOQV-UHFFFAOYSA-N COCC(O1)=C(N)OC1=O Chemical compound COCC(O1)=C(N)OC1=O JMNFLHLUKPBOQV-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229940123464 Thiazolidinedione Drugs 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000000785 adrenergic beta-1 receptor agonist Substances 0.000 description 3
- 239000000808 adrenergic beta-agonist Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000002050 diffraction method Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 description 3
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- JTRNQXJBIZLFMI-YVLHZVERSA-N (5z)-5-[[4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC=C1C(O)COC(C=C1)=CC=C1\C=C/1C(=O)NC(=O)S\1 JTRNQXJBIZLFMI-YVLHZVERSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- YZPBMJZGHIBDAM-UHFFFAOYSA-N 2-(2-fluorophenyl)oxirane Chemical compound FC1=CC=CC=C1C1OC1 YZPBMJZGHIBDAM-UHFFFAOYSA-N 0.000 description 2
- JAIRKHCPVDKYCX-UHFFFAOYSA-N 2-(2-methoxyphenyl)oxirane Chemical compound COC1=CC=CC=C1C1OC1 JAIRKHCPVDKYCX-UHFFFAOYSA-N 0.000 description 2
- YVMKRPGFBQGEBF-UHFFFAOYSA-N 2-(3-chlorophenyl)oxirane Chemical compound ClC1=CC=CC(C2OC2)=C1 YVMKRPGFBQGEBF-UHFFFAOYSA-N 0.000 description 2
- HNBRZCKMGQHNJA-UHFFFAOYSA-N 2-(3-fluorophenyl)oxirane Chemical compound FC1=CC=CC(C2OC2)=C1 HNBRZCKMGQHNJA-UHFFFAOYSA-N 0.000 description 2
- IJUUWUSPXYGGKY-UHFFFAOYSA-N 2-(3-methoxyphenyl)oxirane Chemical compound COC1=CC=CC(C2OC2)=C1 IJUUWUSPXYGGKY-UHFFFAOYSA-N 0.000 description 2
- ICVNPQMUUHPPOK-UHFFFAOYSA-N 2-(4-fluorophenyl)oxirane Chemical compound C1=CC(F)=CC=C1C1OC1 ICVNPQMUUHPPOK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- JBTHBTSSMDDZEH-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)-2-hydroxyethoxy]benzaldehyde Chemical compound C=1C=CC=C(F)C=1C(O)COC1=CC=C(C=O)C=C1 JBTHBTSSMDDZEH-UHFFFAOYSA-N 0.000 description 2
- YFDPWIWWVHDHHV-UHFFFAOYSA-N 4-[2-(3-chlorophenyl)-2-hydroxyethoxy]benzaldehyde Chemical compound C=1C=CC(Cl)=CC=1C(O)COC1=CC=C(C=O)C=C1 YFDPWIWWVHDHHV-UHFFFAOYSA-N 0.000 description 2
- REDLCWTVOOVURK-UHFFFAOYSA-N 4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde Chemical compound COC1=CC=CC=C1C(O)COC1=CC=C(C=O)C=C1 REDLCWTVOOVURK-UHFFFAOYSA-N 0.000 description 2
- NEOHGQHFAJJLCE-UHFFFAOYSA-N 4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzaldehyde Chemical compound COC1=CC=CC(C(O)COC=2C=CC(C=O)=CC=2)=C1 NEOHGQHFAJJLCE-UHFFFAOYSA-N 0.000 description 2
- CBSOPWMHWCBQLT-UHFFFAOYSA-N 5-[(4-phenacyloxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C(=O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O CBSOPWMHWCBQLT-UHFFFAOYSA-N 0.000 description 2
- IUPRGKRCEIKQKP-UHFFFAOYSA-N 5-[[4-(2-hydroxy-2-phenylethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O IUPRGKRCEIKQKP-UHFFFAOYSA-N 0.000 description 2
- RWFYLNYGVYFTST-UHFFFAOYSA-N 5-[[4-(2-hydroxy-2-phenylethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C(O)COC(C=C1)=CC=C1C=C1SC(=O)NC1=O RWFYLNYGVYFTST-UHFFFAOYSA-N 0.000 description 2
- IFQTTXNHJAOPTH-UHFFFAOYSA-N 5-[[4-[2-(2-fluorophenyl)-2-hydroxyethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC=C(F)C=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O IFQTTXNHJAOPTH-UHFFFAOYSA-N 0.000 description 2
- HRAMDLIGGDIZQZ-UHFFFAOYSA-N 5-[[4-[2-(2-fluorophenyl)-2-hydroxyethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC=C(F)C=1C(O)COC(C=C1)=CC=C1C=C1SC(=O)NC1=O HRAMDLIGGDIZQZ-UHFFFAOYSA-N 0.000 description 2
- OXHSWPDYQGAFEI-UHFFFAOYSA-N 5-[[4-[2-(2-fluorophenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound FC1=CC=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OXHSWPDYQGAFEI-UHFFFAOYSA-N 0.000 description 2
- KAPTWVJENIPELD-UHFFFAOYSA-N 5-[[4-[2-(2-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 KAPTWVJENIPELD-UHFFFAOYSA-N 0.000 description 2
- NPYXLMBFTNFZJN-UHFFFAOYSA-N 5-[[4-[2-(3-chlorophenyl)-2-hydroxyethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC(Cl)=CC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O NPYXLMBFTNFZJN-UHFFFAOYSA-N 0.000 description 2
- CKBRGANSZFJOCP-UHFFFAOYSA-N 5-[[4-[2-(3-chlorophenyl)-2-hydroxyethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC(Cl)=CC=1C(O)COC(C=C1)=CC=C1C=C1SC(=O)NC1=O CKBRGANSZFJOCP-UHFFFAOYSA-N 0.000 description 2
- IDXQCXVBTJEBBC-UHFFFAOYSA-N 5-[[4-[2-(3-fluorophenyl)-2-hydroxyethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC(F)=CC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O IDXQCXVBTJEBBC-UHFFFAOYSA-N 0.000 description 2
- UZDBUHARNHZKSR-UHFFFAOYSA-N 5-[[4-[2-(3-fluorophenyl)-2-hydroxyethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=CC(F)=CC=1C(O)COC(C=C1)=CC=C1C=C1SC(=O)NC1=O UZDBUHARNHZKSR-UHFFFAOYSA-N 0.000 description 2
- IIGWSNXQHIPVGU-UHFFFAOYSA-N 5-[[4-[2-(4-fluorophenyl)-2-hydroxyethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(F)C=CC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O IIGWSNXQHIPVGU-UHFFFAOYSA-N 0.000 description 2
- JNSMTGNTYMDJQX-UHFFFAOYSA-N 5-[[4-[2-(4-fluorophenyl)-2-hydroxyethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(F)C=CC=1C(O)COC(C=C1)=CC=C1C=C1SC(=O)NC1=O JNSMTGNTYMDJQX-UHFFFAOYSA-N 0.000 description 2
- JYNMCZSAZCFOPL-UHFFFAOYSA-N 5-[[4-[2-(4-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 JYNMCZSAZCFOPL-UHFFFAOYSA-N 0.000 description 2
- SQJJTGQJZOPUFT-UHFFFAOYSA-N 5-[[4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC=C1C(O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 SQJJTGQJZOPUFT-UHFFFAOYSA-N 0.000 description 2
- GTVRJNNFXVMASB-UHFFFAOYSA-N 5-[[4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC(C(O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 GTVRJNNFXVMASB-UHFFFAOYSA-N 0.000 description 2
- DRZMAAKQUYCSSZ-UHFFFAOYSA-N 5-[[4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=CC(C(O)COC=2C=CC(C=C3C(NC(=O)S3)=O)=CC=2)=C1 DRZMAAKQUYCSSZ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108090000204 Dipeptidase 1 Proteins 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 102100039556 Galectin-4 Human genes 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 2
- 241001272567 Hominoidea Species 0.000 description 2
- 101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 2
- 101000741790 Homo sapiens Peroxisome proliferator-activated receptor gamma Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- NAHKCCQHPPPSLC-UHFFFAOYSA-N O=C(C(Cc(cc1)ccc1OCCc1ccccc1)S1)NC1=O Chemical compound O=C(C(Cc(cc1)ccc1OCCc1ccccc1)S1)NC1=O NAHKCCQHPPPSLC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 229940124639 Selective inhibitor Drugs 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 210000003486 adipose tissue brown Anatomy 0.000 description 2
- 239000000048 adrenergic agonist Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000005001 aminoaryl group Chemical group 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 102000006635 beta-lactamase Human genes 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 238000012875 competitive assay Methods 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000001700 mitochondrial membrane Anatomy 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 2
- 125000004971 nitroalkyl group Chemical group 0.000 description 2
- 239000012740 non-selective inhibitor Substances 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 125000005542 phthalazyl group Chemical group 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- PQCFIIIBRQVVGW-UHFFFAOYSA-M potassium;5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [K+].COC1=CC=CC(C(=O)COC=2C=CC(CC3C([N-]C(=O)S3)=O)=CC=2)=C1 PQCFIIIBRQVVGW-UHFFFAOYSA-M 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 2
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- QKLXBIHSGMPUQS-FGZHOGPDSA-M (3r,5r)-7-[4-(4-fluorophenyl)-2,5-dimethyl-1-phenylpyrrol-3-yl]-3,5-dihydroxyheptanoate Chemical compound CC1=C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C(C)N1C1=CC=CC=C1 QKLXBIHSGMPUQS-FGZHOGPDSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- FJQZXCPWAGYPSD-UHFFFAOYSA-N 1,3,4,6-tetrachloro-3a,6a-diphenylimidazo[4,5-d]imidazole-2,5-dione Chemical compound ClN1C(=O)N(Cl)C2(C=3C=CC=CC=3)N(Cl)C(=O)N(Cl)C12C1=CC=CC=C1 FJQZXCPWAGYPSD-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
- YNQXOOPPJWSXMW-UHFFFAOYSA-N 1-ethenyl-2-fluorobenzene Chemical compound FC1=CC=CC=C1C=C YNQXOOPPJWSXMW-UHFFFAOYSA-N 0.000 description 1
- ZJSKEGAHBAHFON-UHFFFAOYSA-N 1-ethenyl-3-fluorobenzene Chemical compound FC1=CC=CC(C=C)=C1 ZJSKEGAHBAHFON-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- RTPJBMWUVSTBPC-UHFFFAOYSA-N 2-(2-chlorophenyl)oxirane Chemical compound ClC1=CC=CC=C1C1OC1 RTPJBMWUVSTBPC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ARHIWOBUUAPVTB-UHFFFAOYSA-N 2-(4-methoxyphenyl)oxirane Chemical compound C1=CC(OC)=CC=C1C1OC1 ARHIWOBUUAPVTB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- MGUBQPRSQWCLCX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C.CN1C(=O)NC(=O)C2=C1N=CN2C MGUBQPRSQWCLCX-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- JGGLHDVNQCTLAV-UHFFFAOYSA-N 4-(2-hydroxy-2-phenylethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1C(O)COC1=CC=C(C=O)C=C1 JGGLHDVNQCTLAV-UHFFFAOYSA-N 0.000 description 1
- JGGLHDVNQCTLAV-OAHLLOKOSA-N 4-[(2s)-2-hydroxy-2-phenylethoxy]benzaldehyde Chemical compound C([C@@H](O)C=1C=CC=CC=1)OC1=CC=C(C=O)C=C1 JGGLHDVNQCTLAV-OAHLLOKOSA-N 0.000 description 1
- ZUCFOGQIKVVNAM-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)-2-hydroxyethoxy]benzaldehyde Chemical compound C=1C=CC(F)=CC=1C(O)COC1=CC=C(C=O)C=C1 ZUCFOGQIKVVNAM-UHFFFAOYSA-N 0.000 description 1
- CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 description 1
- 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
- KIDSZAGMJRDBTD-UHFFFAOYSA-N 5-[[4-[2-(2-chlorophenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 KIDSZAGMJRDBTD-UHFFFAOYSA-N 0.000 description 1
- MOFCPMNFNJGTGI-UHFFFAOYSA-N 5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 MOFCPMNFNJGTGI-UHFFFAOYSA-N 0.000 description 1
- ZAQBQXQEWVKYJO-UHFFFAOYSA-N 5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;sulfuric acid Chemical compound OS(O)(=O)=O.N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 ZAQBQXQEWVKYJO-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- WGXSAZUGFXLJPQ-UHFFFAOYSA-N C/[O]=C\C(COc1ccc(CC(C(N2)=O)SC2=O)cc1)c1ccccc1Cl Chemical compound C/[O]=C\C(COc1ccc(CC(C(N2)=O)SC2=O)cc1)c1ccccc1Cl WGXSAZUGFXLJPQ-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- DVRWJKZUVBVGEQ-ZENAZSQFSA-N CC(O[C@@H](COc1ccc(CC(C(N2)=O)SC2=O)cc1)c1cc(Cl)ccc1)=O Chemical compound CC(O[C@@H](COc1ccc(CC(C(N2)=O)SC2=O)cc1)c1cc(Cl)ccc1)=O DVRWJKZUVBVGEQ-ZENAZSQFSA-N 0.000 description 1
- DUYHCMNMUYYIJP-UHFFFAOYSA-N CCc(cc1)cnc1C(COc1ccc(CC(C)(C(N2)=O)SC2=O)cc1)=O Chemical compound CCc(cc1)cnc1C(COc1ccc(CC(C)(C(N2)=O)SC2=O)cc1)=O DUYHCMNMUYYIJP-UHFFFAOYSA-N 0.000 description 1
- MHEVYYJAMRRSPS-DIAVIDTQSA-N CCc1cnc([C@@H](COc2ccc(CC(C)(C(N3)=O)SC3=O)cc2)O)cc1 Chemical compound CCc1cnc([C@@H](COc2ccc(CC(C)(C(N3)=O)SC3=O)cc2)O)cc1 MHEVYYJAMRRSPS-DIAVIDTQSA-N 0.000 description 1
- PWUCBURCYLEPDW-OYKVQYDMSA-N CCc1cnc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)OC(CCC(O)=O)=O)cc1 Chemical compound CCc1cnc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)OC(CCC(O)=O)=O)cc1 PWUCBURCYLEPDW-OYKVQYDMSA-N 0.000 description 1
- ZFSJTUQDFQCRDW-UHFFFAOYSA-N COc(c(C(COc1ccc(CC(C(N2)=O)SC2=O)cc1)C=O)ccc1)c1N(C(C(Cc(cc1)ccc1OCC(c1cc(Cl)ccc1)O)S1)=O)C1=O Chemical compound COc(c(C(COc1ccc(CC(C(N2)=O)SC2=O)cc1)C=O)ccc1)c1N(C(C(Cc(cc1)ccc1OCC(c1cc(Cl)ccc1)O)S1)=O)C1=O ZFSJTUQDFQCRDW-UHFFFAOYSA-N 0.000 description 1
- GTVRJNNFXVMASB-BHWOMJMDSA-N COc1cc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)ccc1 Chemical compound COc1cc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)ccc1 GTVRJNNFXVMASB-BHWOMJMDSA-N 0.000 description 1
- UWGAAIIHFPBFJN-TZHYSIJRSA-N COc1ccc([C@@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)cc1 Chemical compound COc1ccc([C@@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)cc1 UWGAAIIHFPBFJN-TZHYSIJRSA-N 0.000 description 1
- SQHAQKILCVTNDU-FIWHBWSRSA-N COc1ccc([C@@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)OC(CCCC(O)=O)=O)cc1 Chemical compound COc1ccc([C@@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)OC(CCCC(O)=O)=O)cc1 SQHAQKILCVTNDU-FIWHBWSRSA-N 0.000 description 1
- UWGAAIIHFPBFJN-BHWOMJMDSA-N COc1ccc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)cc1 Chemical compound COc1ccc([C@H](COc2ccc(CC(C(N3)=O)SC3=O)cc2)O)cc1 UWGAAIIHFPBFJN-BHWOMJMDSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VLCWGADMKVYRBZ-UHFFFAOYSA-N Cc1ccc(C(CC=O)COc2ccc(CC(C(N3)=O)SC3=O)cc2)cc1 Chemical compound Cc1ccc(C(CC=O)COc2ccc(CC(C(N3)=O)SC3=O)cc2)cc1 VLCWGADMKVYRBZ-UHFFFAOYSA-N 0.000 description 1
- GESXVGSMDCZIAQ-UHFFFAOYSA-N Cc1ccc(C(COc2ccc(CC(C(N3)=O)SC3=O)cc2)OS(N)(=O)=O)cc1 Chemical compound Cc1ccc(C(COc2ccc(CC(C(N3)=O)SC3=O)cc2)OS(N)(=O)=O)cc1 GESXVGSMDCZIAQ-UHFFFAOYSA-N 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 238000002957 GeneBLAzer Methods 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 241000288105 Grus Species 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 108091016366 Histone-lysine N-methyltransferase EHMT1 Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000012741 Laemmli sample buffer Substances 0.000 description 1
- 102000016267 Leptin Human genes 0.000 description 1
- 108010092277 Leptin Proteins 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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- AYUWJGCHDJEWKD-UHFFFAOYSA-N O=C(C(Cc(cc1)ccc1OCCc(cc1)ccc1Cl)S1)NC1=O Chemical compound O=C(C(Cc(cc1)ccc1OCCc(cc1)ccc1Cl)S1)NC1=O AYUWJGCHDJEWKD-UHFFFAOYSA-N 0.000 description 1
- CGDGWYFFAALKJB-UHFFFAOYSA-N OCC(COc1ccc(CC(C(N2COc3cccc(CCOc4ccc(CC(C(N5)=O)SC5=O)cc4)c3)=O)SC2=O)cc1)c1cc(F)ccc1 Chemical compound OCC(COc1ccc(CC(C(N2COc3cccc(CCOc4ccc(CC(C(N5)=O)SC5=O)cc4)c3)=O)SC2=O)cc1)c1cc(F)ccc1 CGDGWYFFAALKJB-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 239000007997 Tricine buffer Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- UWAOJIWUVCMBAZ-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-dimethylazanium;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UWAOJIWUVCMBAZ-UHFFFAOYSA-N 0.000 description 1
- ADJGILYWRFPXQS-UHFFFAOYSA-N [4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl] 2-(5-ethylpyridin-2-yl)acetate Chemical compound N1=CC(CC)=CC=C1CC(=O)OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 ADJGILYWRFPXQS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005354 acylalkyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 230000011759 adipose tissue development Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 125000005021 aminoalkenyl group Chemical group 0.000 description 1
- 125000005214 aminoheteroaryl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 229940125388 beta agonist Drugs 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229950001653 cilomilast Drugs 0.000 description 1
- 229960004588 cilostazol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- BALGDZWGNCXXES-UHFFFAOYSA-N cyclopentane;propanoic acid Chemical compound CCC(O)=O.C1CCCC1 BALGDZWGNCXXES-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 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
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000667 effect on insulin Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 description 1
- 210000000497 foam cell Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000014101 glucose homeostasis Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000002660 insulin-secreting cell Anatomy 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- 238000004989 laser desorption mass spectroscopy Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
- 229940039781 leptin Drugs 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000004322 lipid homeostasis Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229940045623 meridia Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 210000000107 myocyte Anatomy 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 229940041678 oral spray Drugs 0.000 description 1
- 239000000668 oral spray Substances 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021400 peanut butter Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000002824 peroxisome Anatomy 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- BITXWGSHQGLFDD-UHFFFAOYSA-M potassium;5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [K+].N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)[N-]C(=O)S1 BITXWGSHQGLFDD-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960002586 roflumilast Drugs 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- OZJDMAGRSNXUOZ-UHFFFAOYSA-M sodium;5-[[4-[2-(3-methoxyphenyl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [Na+].COC1=CC=CC(C(=O)COC=2C=CC(CC3C([N-]C(=O)S3)=O)=CC=2)=C1 OZJDMAGRSNXUOZ-UHFFFAOYSA-M 0.000 description 1
- CSJLSCCIEWQXHW-UHFFFAOYSA-M sodium;5-[[4-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [Na+].N1=CC(CC)=CC=C1C(=O)COC(C=C1)=CC=C1CC1C(=O)[N-]C(=O)S1 CSJLSCCIEWQXHW-UHFFFAOYSA-M 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LXUQDZITPQYMIR-UHFFFAOYSA-N thiourea;urea Chemical compound NC(N)=O.NC(N)=S LXUQDZITPQYMIR-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 229940002552 xenical Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/34—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- A61P3/08—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
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28676509P | 2009-12-15 | 2009-12-15 | |
| US61/286,765 | 2009-12-15 | ||
| PCT/US2010/060439 WO2011084453A1 (en) | 2009-12-15 | 2010-12-15 | Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012129930A RU2012129930A (ru) | 2014-01-27 |
| RU2564661C2 true RU2564661C2 (ru) | 2015-10-10 |
Family
ID=43501294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012129930/04A RU2564661C2 (ru) | 2009-12-15 | 2010-12-15 | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8912335B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2513070B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5634526B2 (cg-RX-API-DMAC7.html) |
| KR (3) | KR102029560B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102753539B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010340055B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2783468C (cg-RX-API-DMAC7.html) |
| DK (1) | DK2513070T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2658168T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE038042T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2012006725A (cg-RX-API-DMAC7.html) |
| NO (1) | NO2513070T3 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ600390A (cg-RX-API-DMAC7.html) |
| PL (1) | PL2513070T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2564661C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011084453A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2564661C2 (ru) | 2009-12-15 | 2015-10-10 | МЕТАБОЛИК СОЛЮШНЗ ДЕВЕЛОПМЕНТ КОМПАНИ, ЭлЭлСи | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ |
| UA116217C2 (uk) | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
| CA2895875A1 (en) | 2012-12-21 | 2014-06-26 | Sanofi | Exendin-4 derivatives |
| KR102349803B1 (ko) | 2013-07-22 | 2022-01-12 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 대사 질환의 치료를 위한 ppar-절약 화합물 |
| WO2015086733A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Dual glp-1/glucagon receptor agonists |
| EP3080154B1 (en) | 2013-12-13 | 2018-02-07 | Sanofi | Dual glp-1/gip receptor agonists |
| WO2015086730A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Non-acylated exendin-4 peptide analogues |
| EP3080150B1 (en) | 2013-12-13 | 2018-08-01 | Sanofi | Exendin-4 peptide analogues as dual glp-1/gip receptor agonists |
| TW201625669A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自艾塞那肽－４（Ｅｘｅｎｄｉｎ－４）之肽類雙重ＧＬＰ－１／升糖素受體促效劑 |
| TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重ｇｌｐ－１／昇糖素受體激動劑之艾塞那肽－４衍生物 |
| TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自ｅｘｅｎｄｉｎ－４之雙重ｇｌｐ－１／升糖素受體促效劑 |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
| AR105284A1 (es) | 2015-07-10 | 2017-09-20 | Sanofi Sa | Derivados de exendina-4 como agonistas peptídicos duales específicos de los receptores de glp-1 / glucagón |
| US20210038566A1 (en) | 2018-02-08 | 2021-02-11 | Enyo Pharma | Use of modulators of neet proteins for the treatment of infection |
| CN111689934B (zh) * | 2020-06-24 | 2022-08-02 | 郑州大学 | 14-脱羟-13-脱氢穿心莲内酯-12-磺酸钾的单晶体及制备方法 |
| GB202210503D0 (en) | 2022-07-18 | 2022-08-31 | Univ Court Univ Of Glasgow | Materials and methods for treatment of chronic myeloid leukemia (CML) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155845A1 (en) * | 1984-03-21 | 1985-09-25 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| EP0193256A1 (en) * | 1985-01-19 | 1986-09-03 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| RU2323004C2 (ru) * | 1995-06-20 | 2008-04-27 | Такеда Фармасьютикал Компани Лимитед | Фармацевтическая композиция |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| WO1985004170A1 (fr) | 1984-03-21 | 1985-09-26 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, leur procede de preparation et compositions medicinales les contenant |
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| WO1986002073A1 (fr) | 1984-10-03 | 1986-04-10 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant |
| US5167228A (en) | 1987-06-26 | 1992-12-01 | Brigham And Women's Hospital | Assessment and modification of endogenous circadian phase and amplitude |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5143930A (en) | 1990-02-07 | 1992-09-01 | Sankyo Company, Limited | Thiazolidine derivatives with anti-diabetic activity, their preparation and their use |
| US5356913A (en) | 1990-02-09 | 1994-10-18 | The Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| EP0579733B1 (en) | 1991-04-11 | 2001-06-20 | PHARMACIA & UPJOHN COMPANY | Thiazolidinedione derivatives, production and use thereof |
| US5441971A (en) | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| NO302471B1 (no) | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| IL118778A (en) | 1995-07-03 | 1999-07-14 | Sankyo Co | Pharmaceutical compositions for the treatment of arteriosclerosis and xanthoma containing an hmg-coa reductase inhibitor |
| US7407978B2 (en) | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| AU776162B2 (en) | 1999-04-29 | 2004-08-26 | City Of Hope | Pentoxifylline, pioglitazone and metformin are inhibitors of formation of advanced glycation endproducts (AGE's) |
| US6331596B1 (en) | 1999-06-28 | 2001-12-18 | Basf Corporation | Method of preparing carbamate-functional polymers |
| WO2001000579A1 (en) | 1999-06-30 | 2001-01-04 | Tularik Inc. | COMPOUNDS FOR THE MODULATION OF PPARη ACTIVITY |
| AU6118001A (en) | 2000-05-03 | 2001-11-12 | Tularik Inc | Combination therapeutic compositions and methods of use |
| AU2002226365A1 (en) | 2000-12-01 | 2002-06-11 | Novartis Ag | Combinations of an angiotensin receptor antagonist and an anti-hypertensive drug or a statin, for the treatment of sexual dysfunction |
| EE200300519A (et) | 2001-04-26 | 2004-02-16 | L�civa, a.s. | Meetod pioglitasooni kui suhkurtõvevastase aine saamiseks |
| AU2002337749A1 (en) | 2001-09-28 | 2003-04-07 | Teva Pharmaceutical Industries Ltd. | Pioglitazone hydrochloride |
| AUPS236902A0 (en) | 2002-05-16 | 2002-06-13 | Northern Sydney Area Health Service | Composition and method for treating hypertension |
| AU2003272072A1 (en) | 2002-07-16 | 2004-02-02 | Cadila Healthcare Limited | A process to prepare pioglitazone via several intermediates. |
| US20060083784A1 (en) | 2002-08-07 | 2006-04-20 | Smithkline Beecham Corporation | Amorphous pharmaceutical compositions |
| US7230016B2 (en) | 2003-05-13 | 2007-06-12 | Synthon Ip Inc. | Pioglitazone salts, such as pioglitazone sulfate, and pharmaceutical compositions and processes using the same |
| WO2005021542A2 (en) | 2003-08-28 | 2005-03-10 | Ranbaxy Laboratories Limited | Process for the preparation of pioglitazone |
| AR047541A1 (es) | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
| JP4475983B2 (ja) | 2004-03-03 | 2010-06-09 | 学校法人日本大学 | Ｂｍａｌ１を阻害する方法 |
| AU2005288080B2 (en) | 2004-09-28 | 2011-10-13 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compound |
| NZ571872A (en) | 2006-03-16 | 2011-05-27 | Metabolic Solutions Dev Co | Combination therapies of thiazolidinedione analogues and glucocorticoid agonists |
| ES2654908T3 (es) | 2006-03-16 | 2018-02-15 | Metabolic Solutions Development Company Llc | Análogos de tiazolidindiona para el tratamiento de enfermedades mediadas por una inflamación metabólica |
| CN101454006B (zh) | 2006-03-16 | 2012-12-26 | 新陈代谢解决方案开发公司 | 用于治疗高血压以及用于降低血脂的噻唑烷二酮类似物 |
| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| JP5371988B2 (ja) | 2007-09-14 | 2013-12-18 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 高血圧を処置するためのチアゾリジンジオン類似体 |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| SI2222272T1 (sl) | 2008-08-07 | 2013-03-29 | Pulmagen Therapeutics (Inflammation) Limited | Zdravljenje respiratorne bolezni. |
| WO2010105048A1 (en) | 2009-03-12 | 2010-09-16 | Metabolic Solutions Development Company | Thiazolidinedione analogues |
| WO2011017244A1 (en) | 2009-08-05 | 2011-02-10 | Metabolic Solutions Development Company | Polymorphs of 5-(4-(2-(5-ethylpyridin-2-yl)-2-oxoethoxy)benzyl)-1,3-thiazolidine-2,4-dione (mitoglitazone) |
| KR20120092712A (ko) | 2009-12-15 | 2012-08-21 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 진성 당뇨병 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 |
| RU2564661C2 (ru) | 2009-12-15 | 2015-10-10 | МЕТАБОЛИК СОЛЮШНЗ ДЕВЕЛОПМЕНТ КОМПАНИ, ЭлЭлСи | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ |
| JP2013514371A (ja) | 2009-12-15 | 2013-04-25 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 肥満および他の代謝性疾患の処置のためのＰＰＡＲγ温存チアゾリジンジオンならびに組み合わせ物 |
| EP3202401B1 (en) | 2009-12-15 | 2019-10-23 | Cirius Therapeutics, Inc. | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| JP2013525362A (ja) | 2010-04-21 | 2013-06-20 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | チアゾリジンジオン類似体 |
-
2010
- 2010-12-15 RU RU2012129930/04A patent/RU2564661C2/ru active
- 2010-12-15 KR KR1020177010102A patent/KR102029560B1/ko active Active
- 2010-12-15 MX MX2012006725A patent/MX2012006725A/es active IP Right Grant
- 2010-12-15 KR KR1020127018388A patent/KR20120107493A/ko not_active Ceased
- 2010-12-15 ES ES10796247.4T patent/ES2658168T3/es active Active
- 2010-12-15 AU AU2010340055A patent/AU2010340055B2/en active Active
- 2010-12-15 NZ NZ600390A patent/NZ600390A/xx unknown
- 2010-12-15 JP JP2012544740A patent/JP5634526B2/ja active Active
- 2010-12-15 PL PL10796247T patent/PL2513070T3/pl unknown
- 2010-12-15 US US13/515,508 patent/US8912335B2/en active Active
- 2010-12-15 NO NO10796247A patent/NO2513070T3/no unknown
- 2010-12-15 WO PCT/US2010/060439 patent/WO2011084453A1/en not_active Ceased
- 2010-12-15 KR KR1020187022229A patent/KR102029611B1/ko active Active
- 2010-12-15 EP EP10796247.4A patent/EP2513070B1/en active Active
- 2010-12-15 DK DK10796247.4T patent/DK2513070T3/en active
- 2010-12-15 CN CN201080063893.4A patent/CN102753539B/zh active Active
- 2010-12-15 HU HUE10796247A patent/HUE038042T2/hu unknown
- 2010-12-15 CA CA2783468A patent/CA2783468C/en active Active
-
2014
- 2014-10-30 US US14/528,163 patent/US9126959B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155845A1 (en) * | 1984-03-21 | 1985-09-25 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| EP0193256A1 (en) * | 1985-01-19 | 1986-09-03 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
| RU2323004C2 (ru) * | 1995-06-20 | 2008-04-27 | Такеда Фармасьютикал Компани Лимитед | Фармацевтическая композиция |
Non-Patent Citations (4)
| Title |
|---|
| KULKARNI SANTOSH S. et al.: "Three-dimensional quantitative structure activity relationships (3-D-QSAR) of antihyperglycemic agents", BIOORGANIC & MEDICINAL CHEMISTRY, 1999, vol.7, p.1475-1485. * |
| SOHDA T. et al: "Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones", ARZNEIMITTEL-FORSCHUNG, DRUG RESEARCH, 1990, vol.40, no.1, p.37-42. * |
| STEPHEN M.BERGE et al.: "Pharmaceuticals salts", JOURNAL OF PHARMACEUTICAL SCIENCES, 1977, vol.66, no.1, p.1-16, . RICHARD J.BASTIN et al.: "Salt selection and optimization procedures for pharmaceutical new chemical entities", ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, vol.4, no.5, p.427-435, . * |
| TAKASHI SOHDA et al.: "Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)-benzyl]thiazolidine-2,4-dione (ADD-3878) and its derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, 1982, vol.30, no.10, p.3580-3600. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2658168T3 (es) | 2018-03-08 |
| NO2513070T3 (cg-RX-API-DMAC7.html) | 2018-04-07 |
| AU2010340055A1 (en) | 2012-06-28 |
| MX2012006725A (es) | 2012-06-28 |
| KR20180089569A (ko) | 2018-08-08 |
| KR20120107493A (ko) | 2012-10-02 |
| NZ600390A (en) | 2013-08-30 |
| US20120309975A1 (en) | 2012-12-06 |
| EP2513070B1 (en) | 2017-11-08 |
| HUE038042T2 (hu) | 2018-09-28 |
| CA2783468C (en) | 2018-10-09 |
| RU2012129930A (ru) | 2014-01-27 |
| DK2513070T3 (en) | 2018-01-22 |
| PL2513070T3 (pl) | 2018-05-30 |
| WO2011084453A1 (en) | 2011-07-14 |
| US20150051406A1 (en) | 2015-02-19 |
| HK1174330A1 (en) | 2013-06-07 |
| KR102029560B1 (ko) | 2019-10-07 |
| US8912335B2 (en) | 2014-12-16 |
| AU2010340055B2 (en) | 2014-07-24 |
| US9126959B2 (en) | 2015-09-08 |
| KR20170044214A (ko) | 2017-04-24 |
| CN102753539A (zh) | 2012-10-24 |
| EP2513070A1 (en) | 2012-10-24 |
| JP2013514367A (ja) | 2013-04-25 |
| KR102029611B1 (ko) | 2019-10-07 |
| CA2783468A1 (en) | 2011-07-14 |
| CN102753539B (zh) | 2015-09-09 |
| JP5634526B2 (ja) | 2014-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2564661C2 (ru) | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ | |
| RU2570424C2 (ru) | Рапп-поддерживающие тиазолидиндионы и их комбинации для лечения нейродегенеративных заболеваний | |
| KR20120092712A (ko) | 진성 당뇨병 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 | |
| KR20120092714A (ko) | 비만 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 | |
| RU2594725C2 (ru) | Синтез соединений тиазолидиндиона | |
| RU2593370C2 (ru) | Новый способ синтеза соединений тиазолидиндиона | |
| WO2012149083A1 (en) | Ppar-sparing thiazolidinediones for the treatment of kidney related diseases | |
| HK1174330B (en) | Ppar-sparing thiazolidinedione salts for the treatment of metabolic diseases | |
| HK1176305A (en) | Ppar-sparing thiazolidinediones and combinations for the treatment of obesity and other metabolic diseases | |
| HK1174554A (en) | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC41 | Official registration of the transfer of exclusive right |
Effective date: 20160810 |
|
| PD4A | Correction of name of patent owner |