HRP20010795A2 - Di-aryl acid derivatives as ppar receptor ligands - Google Patents
Di-aryl acid derivatives as ppar receptor ligands Download PDFInfo
- Publication number
- HRP20010795A2 HRP20010795A2 HR20010795A HRP20010795A HRP20010795A2 HR P20010795 A2 HRP20010795 A2 HR P20010795A2 HR 20010795 A HR20010795 A HR 20010795A HR P20010795 A HRP20010795 A HR P20010795A HR P20010795 A2 HRP20010795 A2 HR P20010795A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- mmol
- compound according
- compound
- image
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 19
- 239000002253 acid Substances 0.000 title abstract description 44
- 101150014691 PPARA gene Proteins 0.000 title 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 31
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims description 332
- -1 2-substituted oxazol-4-yl Chemical group 0.000 claims description 245
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 239000000126 substance Substances 0.000 claims description 40
- 108010016731 PPAR gamma Proteins 0.000 claims description 35
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 206010022489 Insulin Resistance Diseases 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 201000008980 hyperinsulinism Diseases 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 230000037406 food intake Effects 0.000 claims description 3
- 235000012631 food intake Nutrition 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 70
- 102000005962 receptors Human genes 0.000 abstract description 19
- 108020003175 receptors Proteins 0.000 abstract description 19
- 150000001204 N-oxides Chemical class 0.000 abstract description 13
- 239000011230 binding agent Substances 0.000 abstract description 9
- 239000000556 agonist Substances 0.000 abstract description 8
- 239000012453 solvate Substances 0.000 abstract description 6
- 239000005557 antagonist Substances 0.000 abstract description 5
- 150000004677 hydrates Chemical class 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 308
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 184
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 139
- 238000000034 method Methods 0.000 description 107
- 238000006243 chemical reaction Methods 0.000 description 103
- 239000000243 solution Substances 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 239000011541 reaction mixture Substances 0.000 description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 67
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
- 229910052757 nitrogen Inorganic materials 0.000 description 60
- 239000000203 mixture Substances 0.000 description 59
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- 235000019439 ethyl acetate Nutrition 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 238000003756 stirring Methods 0.000 description 47
- 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 44
- 239000002904 solvent Substances 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 125000000623 heterocyclic group Chemical group 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 33
- 235000019341 magnesium sulphate Nutrition 0.000 description 33
- 239000011780 sodium chloride Substances 0.000 description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- 102000023984 PPAR alpha Human genes 0.000 description 27
- 238000004587 chromatography analysis Methods 0.000 description 27
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 102000004877 Insulin Human genes 0.000 description 22
- 108090001061 Insulin Proteins 0.000 description 22
- 229940125396 insulin Drugs 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 125000006413 ring segment Chemical group 0.000 description 21
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 238000007792 addition Methods 0.000 description 19
- 239000002585 base Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 16
- 230000033228 biological regulation Effects 0.000 description 16
- 201000010099 disease Diseases 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 229910000104 sodium hydride Inorganic materials 0.000 description 16
- 125000004434 sulfur atom Chemical group 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
- 125000004475 heteroaralkyl group Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000000018 receptor agonist Substances 0.000 description 15
- 229940044601 receptor agonist Drugs 0.000 description 15
- 229940044551 receptor antagonist Drugs 0.000 description 15
- 239000002464 receptor antagonist Substances 0.000 description 15
- 239000012312 sodium hydride Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 description 14
- 125000003831 tetrazolyl group Chemical group 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 239000013058 crude material Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 238000013019 agitation Methods 0.000 description 12
- 239000003472 antidiabetic agent Substances 0.000 description 12
- 238000007664 blowing Methods 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 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 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 235000011054 acetic acid Nutrition 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 11
- 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 11
- 239000008103 glucose Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 210000001789 adipocyte Anatomy 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 10
- 229940126904 hypoglycaemic agent Drugs 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
- 241000534944 Thia Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- 150000003626 triacylglycerols Chemical class 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 8
- DYFCOWPLQRKJSY-UHFFFAOYSA-N 4-(quinolin-2-ylmethoxy)butan-1-ol Chemical compound C1=CC=CC2=NC(COCCCCO)=CC=C21 DYFCOWPLQRKJSY-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000012190 activator Substances 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 230000004069 differentiation Effects 0.000 description 8
- 235000021588 free fatty acids Nutrition 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 230000001603 reducing effect Effects 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
- BXIOYOGIDBGMRG-UHFFFAOYSA-N 3-(quinolin-2-ylmethoxy)propan-1-ol Chemical compound C1=CC=CC2=NC(COCCCO)=CC=C21 BXIOYOGIDBGMRG-UHFFFAOYSA-N 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 230000014509 gene expression Effects 0.000 description 7
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 7
- 229960003105 metformin Drugs 0.000 description 7
- 235000020824 obesity Nutrition 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 7
- 229960001641 troglitazone Drugs 0.000 description 7
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 102000015779 HDL Lipoproteins Human genes 0.000 description 6
- 108010010234 HDL Lipoproteins Proteins 0.000 description 6
- 108010015181 PPAR delta Proteins 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- UDNSKBMNXZVXKW-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CBr UDNSKBMNXZVXKW-UHFFFAOYSA-N 0.000 description 6
- YRJIMTHQIPOSJR-UHFFFAOYSA-N methyl 2-hydroxy-6-methoxybenzoate Chemical compound COC(=O)C1=C(O)C=CC=C1OC YRJIMTHQIPOSJR-UHFFFAOYSA-N 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000000159 protein binding assay Methods 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- UWPKVVOMIIZSIJ-UHFFFAOYSA-N 2,2-dimethyl-3-(quinolin-2-ylmethoxy)propan-1-ol Chemical compound C1=CC=CC2=NC(COCC(C)(CO)C)=CC=C21 UWPKVVOMIIZSIJ-UHFFFAOYSA-N 0.000 description 5
- WKZPEPYQSLALEE-UHFFFAOYSA-N 2-[2-(bromomethyl)-6-methylphenoxy]acetonitrile Chemical compound CC1=CC=CC(CBr)=C1OCC#N WKZPEPYQSLALEE-UHFFFAOYSA-N 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 102000005720 Glutathione transferase Human genes 0.000 description 5
- 108010070675 Glutathione transferase Proteins 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 229940123464 Thiazolidinedione Drugs 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000012148 binding buffer Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 208000029078 coronary artery disease Diseases 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 108020001756 ligand binding domains Proteins 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- GMVMTWGDXADLTF-UHFFFAOYSA-N methyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)propoxymethyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCOCC1=CC=C(C=CC=C2)C2=N1 GMVMTWGDXADLTF-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- UQSRXQMIXSZGLA-UHFFFAOYSA-N 2,4-dihydroxy-6-methylbenzoic acid ethyl ester Chemical compound CCOC(=O)C1=C(C)C=C(O)C=C1O UQSRXQMIXSZGLA-UHFFFAOYSA-N 0.000 description 4
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 4
- HHGBHMFWGLDWAH-UHFFFAOYSA-N 2-(quinolin-2-ylmethoxy)ethanol Chemical compound C1=CC=CC2=NC(COCCO)=CC=C21 HHGBHMFWGLDWAH-UHFFFAOYSA-N 0.000 description 4
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 4
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 4
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 4
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 208000013016 Hypoglycemia Diseases 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- FARMNDXIOAHJMF-UHFFFAOYSA-N [3-(quinolin-2-ylmethoxy)phenyl]methanol Chemical compound OCC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 FARMNDXIOAHJMF-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- COJRWHSKVYUZHQ-UHFFFAOYSA-N alpha-methyl-3-hydroxybenzyl alcohol Natural products CC(O)C1=CC=CC(O)=C1 COJRWHSKVYUZHQ-UHFFFAOYSA-N 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000003143 atherosclerotic effect Effects 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 239000012039 electrophile Substances 0.000 description 4
- BNAGKEKBEJEVFJ-UHFFFAOYSA-N ethyl 2-hydroxy-6-methyl-4-phenylmethoxybenzoate Chemical compound C1=C(O)C(C(=O)OCC)=C(C)C=C1OCC1=CC=CC=C1 BNAGKEKBEJEVFJ-UHFFFAOYSA-N 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 230000003914 insulin secretion Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XJMULMWDHLJUKP-UHFFFAOYSA-N methyl 2,6-dimethylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1C XJMULMWDHLJUKP-UHFFFAOYSA-N 0.000 description 4
- YCZQUEOMCIRERL-UHFFFAOYSA-N n-(3-hydroxypropyl)-n-(quinolin-2-ylmethyl)acetamide Chemical compound C1=CC=CC2=NC(CN(CCCO)C(=O)C)=CC=C21 YCZQUEOMCIRERL-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003752 polymerase chain reaction Methods 0.000 description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- 238000006268 reductive amination reaction Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 3
- PMRFBLQVGJNGLU-UHFFFAOYSA-N -form-1-(4-Hydroxyphenyl)ethanol Natural products CC(O)C1=CC=C(O)C=C1 PMRFBLQVGJNGLU-UHFFFAOYSA-N 0.000 description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 3
- SWBPKWRVRIRWRL-UHFFFAOYSA-N 2-[2-(bromomethyl)-4-chloro-6-methylphenoxy]acetonitrile Chemical compound CC1=CC(Cl)=CC(CBr)=C1OCC#N SWBPKWRVRIRWRL-UHFFFAOYSA-N 0.000 description 3
- YUHKTJACKOMLEG-UHFFFAOYSA-N 2-[2-methyl-6-[3-(quinolin-2-ylmethoxy)propoxymethyl]phenoxy]acetonitrile Chemical compound CC1=CC=CC(COCCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC#N YUHKTJACKOMLEG-UHFFFAOYSA-N 0.000 description 3
- CIBGXJVJPZCMFX-UHFFFAOYSA-N 2-bromobutanenitrile Chemical compound CCC(Br)C#N CIBGXJVJPZCMFX-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- WTPSVPGTKRIMQM-UHFFFAOYSA-N 3-(quinolin-2-ylamino)propan-1-ol Chemical compound C1=CC=CC2=NC(NCCCO)=CC=C21 WTPSVPGTKRIMQM-UHFFFAOYSA-N 0.000 description 3
- LZUMOJGETJSSAZ-UHFFFAOYSA-N 4-(quinolin-2-ylamino)butan-1-ol Chemical compound C1=CC=CC2=NC(NCCCCO)=CC=C21 LZUMOJGETJSSAZ-UHFFFAOYSA-N 0.000 description 3
- ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 3
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 3
- 208000005623 Carcinogenesis Diseases 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 108010024636 Glutathione Proteins 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229960002632 acarbose Drugs 0.000 description 3
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 3
- 229960001466 acetohexamide Drugs 0.000 description 3
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001345 alkine derivatives Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001413 amino acids Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000036952 cancer formation Effects 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 231100000504 carcinogenesis Toxicity 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229960001761 chlorpropamide Drugs 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
- 238000002648 combination therapy Methods 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 102000037865 fusion proteins Human genes 0.000 description 3
- 108020001507 fusion proteins Proteins 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 3
- 229960001381 glipizide Drugs 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 3
- 125000005368 heteroarylthio group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 3
- 206010020718 hyperplasia Diseases 0.000 description 3
- 208000006575 hypertriglyceridemia Diseases 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 description 3
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- KBAWXNDJQWAGTL-UHFFFAOYSA-N methyl 2-[4-[acetyl(quinolin-2-ylmethyl)amino]butoxymethyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCCN(C(C)=O)CC1=CC=C(C=CC=C2)C2=N1 KBAWXNDJQWAGTL-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000036542 oxidative stress Effects 0.000 description 3
- 210000002824 peroxisome Anatomy 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 3
- 229910052705 radium Inorganic materials 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 210000002027 skeletal muscle Anatomy 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- 238000005556 structure-activity relationship Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000003536 tetrazoles Chemical class 0.000 description 3
- 150000001467 thiazolidinediones Chemical class 0.000 description 3
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 3
- 229960002277 tolazamide Drugs 0.000 description 3
- 229960005371 tolbutamide Drugs 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- VGSJXSLGVQINOL-MHZLTWQESA-N (2s)-2-[4-[2-[(2,4-difluorophenyl)carbamoyl-heptylamino]ethyl]phenoxy]-2-methylbutanoic acid Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCC1=CC=C(O[C@@](C)(CC)C(O)=O)C=C1 VGSJXSLGVQINOL-MHZLTWQESA-N 0.000 description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 2
- VHRUMKCAEVRUBK-GODQJPCRSA-N 15-deoxy-Delta(12,14)-prostaglandin J2 Chemical compound CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O VHRUMKCAEVRUBK-GODQJPCRSA-N 0.000 description 2
- LOSLUMRVUKFVDQ-UHFFFAOYSA-N 2-(2-chloroethyl)quinoline Chemical compound C1=CC=CC2=NC(CCCl)=CC=C21 LOSLUMRVUKFVDQ-UHFFFAOYSA-N 0.000 description 2
- CTTDEBFGDMECPC-UHFFFAOYSA-N 2-(2-formyl-6-methylphenoxy)acetonitrile Chemical compound CC1=CC=CC(C=O)=C1OCC#N CTTDEBFGDMECPC-UHFFFAOYSA-N 0.000 description 2
- AXRVMKOHOIVYCO-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)acetonitrile Chemical compound CC1=CC(Cl)=CC(C)=C1OCC#N AXRVMKOHOIVYCO-UHFFFAOYSA-N 0.000 description 2
- NNAYPIDFVQLEDK-UHFFFAOYSA-N 2-(bromomethyl)quinoline Chemical compound C1=CC=CC2=NC(CBr)=CC=C21 NNAYPIDFVQLEDK-UHFFFAOYSA-N 0.000 description 2
- WWQOHRPIZXCSTA-UHFFFAOYSA-N 2-[(3-iodophenoxy)methyl]naphthalene Chemical compound IC1=CC=CC(OCC=2C=C3C=CC=CC3=CC=2)=C1 WWQOHRPIZXCSTA-UHFFFAOYSA-N 0.000 description 2
- SIZIZUJLNDIVKO-UHFFFAOYSA-N 2-[2-(hydroxymethyl)-6-methylphenoxy]acetonitrile Chemical compound CC1=CC=CC(CO)=C1OCC#N SIZIZUJLNDIVKO-UHFFFAOYSA-N 0.000 description 2
- ZLPRMNXLJDIJDD-UHFFFAOYSA-N 2-[2-methyl-6-[2-(quinolin-2-ylmethoxy)ethoxymethyl]phenoxy]acetonitrile Chemical compound CC1=CC=CC(COCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC#N ZLPRMNXLJDIJDD-UHFFFAOYSA-N 0.000 description 2
- RHKDDSVWRSDQCY-UHFFFAOYSA-N 2-[2-methyl-6-[3-(quinolin-2-ylamino)propoxymethyl]phenoxy]acetonitrile Chemical compound CC1=CC=CC(COCCCNC=2N=C3C=CC=CC3=CC=2)=C1OCC#N RHKDDSVWRSDQCY-UHFFFAOYSA-N 0.000 description 2
- ZUCCMZSEPQEVNF-UHFFFAOYSA-N 2-[3-(chloromethyl)phenoxy]acetonitrile Chemical compound ClCC1=CC=CC(OCC#N)=C1 ZUCCMZSEPQEVNF-UHFFFAOYSA-N 0.000 description 2
- FQYJUMVWCVSLPH-UHFFFAOYSA-N 2-[3-(hydroxymethyl)phenoxy]acetonitrile Chemical compound OCC1=CC=CC(OCC#N)=C1 FQYJUMVWCVSLPH-UHFFFAOYSA-N 0.000 description 2
- FTPYWZVOGZHIML-UHFFFAOYSA-N 2-[4-chloro-2-[[2,2-dimethyl-3-(quinolin-2-ylmethoxy)propoxy]methyl]-6-methylphenoxy]acetonitrile Chemical compound CC1=CC(Cl)=CC(COCC(C)(C)COCC=2N=C3C=CC=CC3=CC=2)=C1OCC#N FTPYWZVOGZHIML-UHFFFAOYSA-N 0.000 description 2
- DNSANEGOVOAFSY-UHFFFAOYSA-N 2-[4-chloro-2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxymethyl]phenoxy]acetonitrile Chemical compound CC1=CC(Cl)=CC(COCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC#N DNSANEGOVOAFSY-UHFFFAOYSA-N 0.000 description 2
- QZQFCSAFZBNYHK-UHFFFAOYSA-N 2-[[3-(chloromethyl)phenoxy]methyl]quinoline Chemical compound ClCC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 QZQFCSAFZBNYHK-UHFFFAOYSA-N 0.000 description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 2
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 description 2
- QYGZXNNXBACFTK-UHFFFAOYSA-N 2-methylpropyl 2,6-dimethylbenzoate Chemical compound CC(C)COC(=O)C1=C(C)C=CC=C1C QYGZXNNXBACFTK-UHFFFAOYSA-N 0.000 description 2
- IYPLMIONUBKTHO-UHFFFAOYSA-N 2-methylpropyl 2-(bromomethyl)-6-methylbenzoate Chemical compound CC(C)COC(=O)C1=C(C)C=CC=C1CBr IYPLMIONUBKTHO-UHFFFAOYSA-N 0.000 description 2
- XASQOYSQXIIRDR-UHFFFAOYSA-N 2-methylpropyl 2-methyl-6-[3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]propoxymethyl]benzoate Chemical compound CC(C)COC(=O)C1=C(C)C=CC=C1COCCCOCC1=COC(C=2C=CC=CC=2)=N1 XASQOYSQXIIRDR-UHFFFAOYSA-N 0.000 description 2
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- AMQIPHZFLIDOCB-UHFFFAOYSA-N 3-(2-hydroxyethyl)phenol Chemical compound OCCC1=CC=CC(O)=C1 AMQIPHZFLIDOCB-UHFFFAOYSA-N 0.000 description 2
- SDJQWNMVKBEBSJ-UHFFFAOYSA-N 3-(hydroxymethyl)-5-methylphenol Chemical compound CC1=CC(O)=CC(CO)=C1 SDJQWNMVKBEBSJ-UHFFFAOYSA-N 0.000 description 2
- UMBGNXDCYYVVOL-UHFFFAOYSA-N 3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]propan-1-ol Chemical compound OCCCOCC1=COC(C=2C=CC=CC=2)=N1 UMBGNXDCYYVVOL-UHFFFAOYSA-N 0.000 description 2
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 2
- XXZVBSPSFVERCB-UHFFFAOYSA-N 3-chloro-2-methylpropanenitrile Chemical compound ClCC(C)C#N XXZVBSPSFVERCB-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- NJCVPQRHRKYSAZ-UHFFFAOYSA-N 3-p-hydroxyphenylpropanol Natural products OCCCC1=CC=C(O)C=C1 NJCVPQRHRKYSAZ-UHFFFAOYSA-N 0.000 description 2
- ANSKJZIDWXDAJW-UHFFFAOYSA-N 4-(chloromethyl)-2-phenyl-1,3-oxazole Chemical compound ClCC1=COC(C=2C=CC=CC=2)=N1 ANSKJZIDWXDAJW-UHFFFAOYSA-N 0.000 description 2
- BEFJEPIMKQDCBC-UHFFFAOYSA-N 5-(3-chloropropyl)-2h-tetrazole Chemical compound ClCCCC1=NN=NN1 BEFJEPIMKQDCBC-UHFFFAOYSA-N 0.000 description 2
- WHKRHBLAJFYZKF-UHFFFAOYSA-N 5-hydroxymethyl-2-methoxy-phenol Natural products COC1=CC=C(CO)C=C1O WHKRHBLAJFYZKF-UHFFFAOYSA-N 0.000 description 2
- WZADRYDUBBGITL-UHFFFAOYSA-N 6-hydroxy-1,3,3-trimethylindol-2-one Chemical compound C1=C(O)C=C2N(C)C(=O)C(C)(C)C2=C1 WZADRYDUBBGITL-UHFFFAOYSA-N 0.000 description 2
- BBMZNBFIUFTOHL-UHFFFAOYSA-N 6-methoxy-1,3,3-trimethylindol-2-one Chemical compound COC1=CC=C2C(C)(C)C(=O)N(C)C2=C1 BBMZNBFIUFTOHL-UHFFFAOYSA-N 0.000 description 2
- HUWLHNLABRKIED-UHFFFAOYSA-N 6-methoxy-3,3-dimethyl-1h-indol-2-one Chemical compound COC1=CC=C2C(C)(C)C(=O)NC2=C1 HUWLHNLABRKIED-UHFFFAOYSA-N 0.000 description 2
- XWCKMYJGFPERAV-UHFFFAOYSA-N 6-methoxy-3-methyl-1,3-dihydroindol-2-one Chemical compound COC1=CC=C2C(C)C(=O)NC2=C1 XWCKMYJGFPERAV-UHFFFAOYSA-N 0.000 description 2
- 201000005670 Anovulation Diseases 0.000 description 2
- 206010002659 Anovulatory cycle Diseases 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100035882 Catalase Human genes 0.000 description 2
- 108010053835 Catalase Proteins 0.000 description 2
- 108020004635 Complementary DNA Proteins 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 201000001376 Familial Combined Hyperlipidemia Diseases 0.000 description 2
- 101710107035 Gamma-glutamyltranspeptidase Proteins 0.000 description 2
- 101710173228 Glutathione hydrolase proenzyme Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000008214 LDL Cholesterol Methods 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 101710117029 Peroxisome proliferator-activated receptor delta Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- OANKJSUXMPAWAT-UHFFFAOYSA-N Sylvopinol Chemical compound COC1=CC(O)=CC(CO)=C1 OANKJSUXMPAWAT-UHFFFAOYSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 231100000552 anovulation Toxicity 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000002402 anti-lipaemic effect Effects 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000003915 cell function Effects 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 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 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FHHWZGATCXNKTF-UHFFFAOYSA-N ethyl 2,4-bis[(4-fluorophenyl)methoxy]-6-methylbenzoate Chemical compound C1=C(OCC=2C=CC(F)=CC=2)C(C(=O)OCC)=C(C)C=C1OCC1=CC=C(F)C=C1 FHHWZGATCXNKTF-UHFFFAOYSA-N 0.000 description 2
- QCQISWYYMODQDN-UHFFFAOYSA-N ethyl 2-methyl-4-phenylmethoxy-6-(3-phenylpropoxy)benzoate Chemical compound C1=C(OCCCC=2C=CC=CC=2)C(C(=O)OCC)=C(C)C=C1OCC1=CC=CC=C1 QCQISWYYMODQDN-UHFFFAOYSA-N 0.000 description 2
- DGOWIHQRBZBCME-UHFFFAOYSA-N ethyl 2-methyl-6-(4-methylpentoxy)-4-phenylmethoxybenzoate Chemical compound C1=C(OCCCC(C)C)C(C(=O)OCC)=C(C)C=C1OCC1=CC=CC=C1 DGOWIHQRBZBCME-UHFFFAOYSA-N 0.000 description 2
- HHCVCIMMALLVHM-UHFFFAOYSA-N ethyl 2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxy]benzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1OCCCCOCC1=CC=C(C=CC=C2)C2=N1 HHCVCIMMALLVHM-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 102000006640 gamma-Glutamyltransferase Human genes 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 229960004580 glibenclamide Drugs 0.000 description 2
- 229960000346 gliclazide Drugs 0.000 description 2
- 230000014101 glucose homeostasis Effects 0.000 description 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 230000002440 hepatic effect Effects 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 201000010066 hyperandrogenism Diseases 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 206010024627 liposarcoma Diseases 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000009245 menopause Effects 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- XVKPDWPIZJGGNX-UHFFFAOYSA-N methyl 2-[3-[acetyl(quinolin-2-ylmethyl)amino]propoxymethyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCN(C(C)=O)CC1=CC=C(C=CC=C2)C2=N1 XVKPDWPIZJGGNX-UHFFFAOYSA-N 0.000 description 2
- NDUXRVMJOYAHDX-UHFFFAOYSA-N methyl 2-[[2,2-dimethyl-3-(quinolin-2-ylmethoxy)propoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCC(C)(C)COCC1=CC=C(C=CC=C2)C2=N1 NDUXRVMJOYAHDX-UHFFFAOYSA-N 0.000 description 2
- YOJKRRVXVIKZTM-UHFFFAOYSA-N methyl 2-methoxy-6-[4-(quinolin-2-ylmethoxy)butoxy]benzoate Chemical compound COC(=O)C1=C(OC)C=CC=C1OCCCCOCC1=CC=C(C=CC=C2)C2=N1 YOJKRRVXVIKZTM-UHFFFAOYSA-N 0.000 description 2
- NSCNKWNFTMDQBR-UHFFFAOYSA-N methyl 2-methyl-6-[3-(quinolin-2-ylamino)propoxymethyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCNC1=CC=C(C=CC=C2)C2=N1 NSCNKWNFTMDQBR-UHFFFAOYSA-N 0.000 description 2
- NGGVVHMFZGVYJI-UHFFFAOYSA-N methyl 2-methyl-6-[4-(quinolin-2-ylamino)butoxymethyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCCNC1=CC=C(C=CC=C2)C2=N1 NGGVVHMFZGVYJI-UHFFFAOYSA-N 0.000 description 2
- FNYASKUQUQEDEB-UHFFFAOYSA-N methyl 2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxymethyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCCOCC1=CC=C(C=CC=C2)C2=N1 FNYASKUQUQEDEB-UHFFFAOYSA-N 0.000 description 2
- XXYCNXPVXHGCOK-UHFFFAOYSA-N methyl 2-methyl-6-[5-(quinolin-2-ylmethoxy)pentoxymethyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COCCCCCOCC1=CC=C(C=CC=C2)C2=N1 XXYCNXPVXHGCOK-UHFFFAOYSA-N 0.000 description 2
- QBGXRXBGZKPMGR-UHFFFAOYSA-N methyl 6-[3-(bromomethyl)phenyl]hexanoate Chemical compound COC(=O)CCCCCC1=CC=CC(CBr)=C1 QBGXRXBGZKPMGR-UHFFFAOYSA-N 0.000 description 2
- PFLUTVKVYZFUCY-UHFFFAOYSA-N methyl 6-[3-(hydroxymethyl)phenyl]hexanoate Chemical compound COC(=O)CCCCCC1=CC=CC(CO)=C1 PFLUTVKVYZFUCY-UHFFFAOYSA-N 0.000 description 2
- LKUDCDPSCBHWER-UHFFFAOYSA-N methyl 6-[3-[(1,3,3-trimethyl-2-oxoindol-6-yl)oxymethyl]phenyl]hexanoate Chemical compound COC(=O)CCCCCC1=CC=CC(COC=2C=C3C(C(C(=O)N3C)(C)C)=CC=2)=C1 LKUDCDPSCBHWER-UHFFFAOYSA-N 0.000 description 2
- DOJHMLXXNKKHAH-UHFFFAOYSA-N methyl 6-[3-[tert-butylsilyloxy(diphenyl)methyl]phenyl]hexanoate Chemical compound COC(CCCCCC1=CC(=CC=C1)C(O[SiH2]C(C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1)=O DOJHMLXXNKKHAH-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000003614 peroxisome proliferator Substances 0.000 description 2
- 230000004526 pharmaceutical effect Effects 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 2
- 230000003248 secreting effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 229910000080 stannane Inorganic materials 0.000 description 2
- 230000010009 steroidogenesis Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- NMYZNJVBOKEHHZ-UHFFFAOYSA-N tert-butyl-[(3-iodophenyl)methoxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC1=CC=CC(I)=C1 NMYZNJVBOKEHHZ-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 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
- 125000001425 triazolyl group Chemical group 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Natural products COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000011534 wash buffer Substances 0.000 description 2
- ITYNGVSTWVVPIC-DHGKCCLASA-N (-)-allo-Aromadendrene Chemical compound C([C@@H]1[C@H]2C1(C)C)CC(=C)[C@@H]1[C@H]2[C@H](C)CC1 ITYNGVSTWVVPIC-DHGKCCLASA-N 0.000 description 1
- IIPCTBAMTPCGJK-UHFFFAOYSA-N (3-sulfanylphenyl)methanol Chemical compound OCC1=CC=CC(S)=C1 IIPCTBAMTPCGJK-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- PDGODEDWTDRGNE-UHFFFAOYSA-N 1,2-dihydro-2,7-naphthyridine Chemical class C1=NC=C2CNC=CC2=C1 PDGODEDWTDRGNE-UHFFFAOYSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- 125000000182 1,4-naphthoquinonyl group Chemical group C1(C(=CC(C2=CC=CC=C12)=O)*)=O 0.000 description 1
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
- XZKFBZOAIGFZSU-UHFFFAOYSA-N 1-bromo-4-methylpentane Chemical compound CC(C)CCCBr XZKFBZOAIGFZSU-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-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
- MLEMNSVJFXSVPB-UHFFFAOYSA-N 2,4-bis[(4-fluorophenyl)methoxy]-6-methylbenzoic acid Chemical compound C=1C(OCC=2C=CC(F)=CC=2)=C(C(O)=O)C(C)=CC=1OCC1=CC=C(F)C=C1 MLEMNSVJFXSVPB-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- JSXTUKSOFJPTFV-UHFFFAOYSA-N 2,6-dibromo-1h-pyridazine Chemical compound BrN1NC(Br)=CC=C1 JSXTUKSOFJPTFV-UHFFFAOYSA-N 0.000 description 1
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
- HCBHQDKBSKYGCK-UHFFFAOYSA-N 2,6-dimethylbenzoic acid Chemical compound CC1=CC=CC(C)=C1C(O)=O HCBHQDKBSKYGCK-UHFFFAOYSA-N 0.000 description 1
- SPBQMQLTSMVQKI-UHFFFAOYSA-N 2-(1-chloroethyl)quinoline Chemical compound C1=CC=CC2=NC(C(Cl)C)=CC=C21 SPBQMQLTSMVQKI-UHFFFAOYSA-N 0.000 description 1
- JVNCFFFHVBWVBR-UHFFFAOYSA-N 2-(1-hydroxyethyl)phenol Chemical compound CC(O)C1=CC=CC=C1O JVNCFFFHVBWVBR-UHFFFAOYSA-N 0.000 description 1
- QWZBWROUTWGTDT-UHFFFAOYSA-N 2-(1-hydroxypropyl)phenol Chemical compound CCC(O)C1=CC=CC=C1O QWZBWROUTWGTDT-UHFFFAOYSA-N 0.000 description 1
- JMRYQHZADMWCBL-UHFFFAOYSA-N 2-(2-chloro-2-phenylethyl)quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CC(Cl)C1=CC=CC=C1 JMRYQHZADMWCBL-UHFFFAOYSA-N 0.000 description 1
- BUDKTSZMYKWZEN-UHFFFAOYSA-N 2-(2-chloropropyl)quinoline Chemical compound C1=CC=CC2=NC(CC(Cl)C)=CC=C21 BUDKTSZMYKWZEN-UHFFFAOYSA-N 0.000 description 1
- ABFCOJLLBHXNOU-UHFFFAOYSA-N 2-(2-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=CC=C1O ABFCOJLLBHXNOU-UHFFFAOYSA-N 0.000 description 1
- HQIVJIVEUGNTQM-UHFFFAOYSA-N 2-(2-hydroxypropyl)phenol Chemical compound CC(O)CC1=CC=CC=C1O HQIVJIVEUGNTQM-UHFFFAOYSA-N 0.000 description 1
- TYNMOIYXEIAPHL-UHFFFAOYSA-N 2-(3-hydroxypropyl)phenol Chemical compound OCCCC1=CC=CC=C1O TYNMOIYXEIAPHL-UHFFFAOYSA-N 0.000 description 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
- FHGYGKQYTPEOPT-UHFFFAOYSA-N 2-(chloromethyl)-4-methylquinoline Chemical compound C1=CC=C2C(C)=CC(CCl)=NC2=C1 FHGYGKQYTPEOPT-UHFFFAOYSA-N 0.000 description 1
- HJCDOCDHYGMKFX-UHFFFAOYSA-N 2-(chloromethyl)-6,8-dimethylquinoline Chemical compound N1=C(CCl)C=CC2=CC(C)=CC(C)=C21 HJCDOCDHYGMKFX-UHFFFAOYSA-N 0.000 description 1
- IFOZFMPOHZGLBK-UHFFFAOYSA-N 2-(chloromethyl)-6-methoxyquinoline Chemical compound N1=C(CCl)C=CC2=CC(OC)=CC=C21 IFOZFMPOHZGLBK-UHFFFAOYSA-N 0.000 description 1
- CSLGYHQUXRUXPX-UHFFFAOYSA-N 2-(chloromethyl)-6-methylquinoline Chemical compound N1=C(CCl)C=CC2=CC(C)=CC=C21 CSLGYHQUXRUXPX-UHFFFAOYSA-N 0.000 description 1
- BWRZMNAKJWZHKT-UHFFFAOYSA-N 2-(chloromethyl)-6-nitroquinoline Chemical compound N1=C(CCl)C=CC2=CC([N+](=O)[O-])=CC=C21 BWRZMNAKJWZHKT-UHFFFAOYSA-N 0.000 description 1
- OVSFGFRGUYAGHH-UHFFFAOYSA-N 2-(chloromethyl)-8-methylquinoline Chemical compound C1=C(CCl)N=C2C(C)=CC=CC2=C1 OVSFGFRGUYAGHH-UHFFFAOYSA-N 0.000 description 1
- UALKLXNEPXDAKT-UHFFFAOYSA-N 2-(cyclohexylmethoxy)-6-methyl-4-phenylmethoxybenzoic acid Chemical compound C=1C(OCC2CCCCC2)=C(C(O)=O)C(C)=CC=1OCC1=CC=CC=C1 UALKLXNEPXDAKT-UHFFFAOYSA-N 0.000 description 1
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
- ZUVDVLYXIZFDRM-UHFFFAOYSA-N 2-(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(CO)=C1 ZUVDVLYXIZFDRM-UHFFFAOYSA-N 0.000 description 1
- KXBMNJFFWQYGGV-UHFFFAOYSA-N 2-[2-(chloromethyl)cyclobutyl]acetonitrile Chemical compound ClCC1CCC1CC#N KXBMNJFFWQYGGV-UHFFFAOYSA-N 0.000 description 1
- DIXMJTJBYQCSET-UHFFFAOYSA-N 2-[2-(chloromethyl)cyclohexyl]acetonitrile Chemical compound ClCC1CCCCC1CC#N DIXMJTJBYQCSET-UHFFFAOYSA-N 0.000 description 1
- RTSXIOCMBYEXTP-UHFFFAOYSA-N 2-[2-methyl-6-[2-(quinolin-2-ylmethoxy)ethoxymethyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(COCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC(O)=O RTSXIOCMBYEXTP-UHFFFAOYSA-N 0.000 description 1
- GWJSEXUFRSOTCE-UHFFFAOYSA-N 2-[2-methyl-6-[3-(quinolin-2-ylamino)propoxymethyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(COCCCNC=2N=C3C=CC=CC3=CC=2)=C1OCC(O)=O GWJSEXUFRSOTCE-UHFFFAOYSA-N 0.000 description 1
- FHHVXELDGGDXGN-UHFFFAOYSA-N 2-[2-methyl-6-[3-(quinolin-2-ylmethoxy)propoxymethyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(COCCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC(O)=O FHHVXELDGGDXGN-UHFFFAOYSA-N 0.000 description 1
- HQXSZYBYBJKWGD-UHFFFAOYSA-N 2-[2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxymethyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(COCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC(O)=O HQXSZYBYBJKWGD-UHFFFAOYSA-N 0.000 description 1
- WQJJNJOOYIKRFL-UHFFFAOYSA-N 2-[3-[acetyl(quinolin-2-ylmethyl)amino]propoxymethyl]-6-methylbenzoic acid Chemical compound C=1C=C2C=CC=CC2=NC=1CN(C(=O)C)CCCOCC1=CC=CC(C)=C1C(O)=O WQJJNJOOYIKRFL-UHFFFAOYSA-N 0.000 description 1
- VGSJXSLGVQINOL-UHFFFAOYSA-N 2-[4-[2-[(2,4-difluorophenyl)carbamoyl-heptylamino]ethyl]phenoxy]-2-methylbutanoic acid Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCC1=CC=C(OC(C)(CC)C(O)=O)C=C1 VGSJXSLGVQINOL-UHFFFAOYSA-N 0.000 description 1
- GWBCLWLJCJMXNE-UHFFFAOYSA-N 2-[4-[acetyl(quinolin-2-ylmethyl)amino]butoxymethyl]-6-methylbenzoic acid Chemical compound C=1C=C2C=CC=CC2=NC=1CN(C(=O)C)CCCCOCC1=CC=CC(C)=C1C(O)=O GWBCLWLJCJMXNE-UHFFFAOYSA-N 0.000 description 1
- YKCMOXAVSXWRRG-UHFFFAOYSA-N 2-[4-chloro-2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxymethyl]phenoxy]acetic acid Chemical compound CC1=CC(Cl)=CC(COCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1OCC(O)=O YKCMOXAVSXWRRG-UHFFFAOYSA-N 0.000 description 1
- IGVXLTZIFKWNKU-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(quinolin-2-ylmethoxy)propoxy]methyl]-6-methylbenzoic acid Chemical compound CC1=CC=CC(COCC(C)(C)COCC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O IGVXLTZIFKWNKU-UHFFFAOYSA-N 0.000 description 1
- QKLZLOJHWRTHQQ-UHFFFAOYSA-N 2-bromobutanenitrile;3-bromobutanenitrile Chemical compound CCC(Br)C#N.CC(Br)CC#N QKLZLOJHWRTHQQ-UHFFFAOYSA-N 0.000 description 1
- WTDNWEITCUMXGW-UHFFFAOYSA-N 2-chlorobutanenitrile Chemical compound CCC(Cl)C#N WTDNWEITCUMXGW-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- AAUQLHHARJUJEH-UHFFFAOYSA-N 2-hydroxy-5-methoxybenzoic acid Natural products COC1=CC=CC(O)=C1C(O)=O AAUQLHHARJUJEH-UHFFFAOYSA-N 0.000 description 1
- ZYWBFPCOBKPQKY-UHFFFAOYSA-N 2-methoxy-6-[4-(quinolin-2-ylmethoxy)butoxy]benzoic acid Chemical compound COC1=CC=CC(OCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O ZYWBFPCOBKPQKY-UHFFFAOYSA-N 0.000 description 1
- MPMLEHKZZHAVJJ-UHFFFAOYSA-N 2-methyl-4-phenylmethoxy-6-(3-phenylpropoxy)benzoic acid Chemical compound C=1C(OCCCC=2C=CC=CC=2)=C(C(O)=O)C(C)=CC=1OCC1=CC=CC=C1 MPMLEHKZZHAVJJ-UHFFFAOYSA-N 0.000 description 1
- XPRZJWZPAAHCEE-UHFFFAOYSA-N 2-methyl-4-phenylmethoxy-6-[4-(quinolin-2-ylmethoxy)butoxy]benzoic acid Chemical compound C=1C(OCCCCOCC=2N=C3C=CC=CC3=CC=2)=C(C(O)=O)C(C)=CC=1OCC1=CC=CC=C1 XPRZJWZPAAHCEE-UHFFFAOYSA-N 0.000 description 1
- ZPDMKVCMXOUGOS-UHFFFAOYSA-N 2-methyl-6-(4-methylpentoxy)-4-phenylmethoxybenzoic acid Chemical compound CC1=C(C(O)=O)C(OCCCC(C)C)=CC(OCC=2C=CC=CC=2)=C1 ZPDMKVCMXOUGOS-UHFFFAOYSA-N 0.000 description 1
- GLAPDNYDUUZPAZ-UHFFFAOYSA-N 2-methyl-6-[3-(quinolin-2-ylamino)propoxymethyl]benzoic acid Chemical compound CC1=CC=CC(COCCCNC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O GLAPDNYDUUZPAZ-UHFFFAOYSA-N 0.000 description 1
- PHNJBAREMRHBAG-UHFFFAOYSA-N 2-methyl-6-[3-(quinolin-2-ylmethoxy)propoxymethyl]benzoic acid Chemical compound CC1=CC=CC(COCCCOCC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O PHNJBAREMRHBAG-UHFFFAOYSA-N 0.000 description 1
- WLHOBCUVPMOXAT-UHFFFAOYSA-N 2-methyl-6-[3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]propoxymethyl]benzoic acid Chemical compound CC1=CC=CC(COCCCOCC=2N=C(OC=2)C=2C=CC=CC=2)=C1C(O)=O WLHOBCUVPMOXAT-UHFFFAOYSA-N 0.000 description 1
- ZHJLQOSAIDDEDP-UHFFFAOYSA-N 2-methyl-6-[4-(quinolin-2-ylamino)butoxymethyl]benzoic acid Chemical compound CC1=CC=CC(COCCCCNC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O ZHJLQOSAIDDEDP-UHFFFAOYSA-N 0.000 description 1
- SCMQDEDDUCNXRD-UHFFFAOYSA-N 2-methyl-6-[4-(quinolin-2-ylmethoxy)butoxy]benzoic acid Chemical compound CC1=CC=CC(OCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O SCMQDEDDUCNXRD-UHFFFAOYSA-N 0.000 description 1
- MBERXHOUBRPIHW-UHFFFAOYSA-N 2-methyl-6-[5-(quinolin-2-ylmethoxy)pentoxymethyl]benzoic acid Chemical compound CC1=CC=CC(COCCCCCOCC=2N=C3C=CC=CC3=CC=2)=C1C(O)=O MBERXHOUBRPIHW-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000004105 2-pyridyl group Chemical class N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 1
- ZWEWBWNQZUJOIF-UHFFFAOYSA-N 3-(1-hydroxypropyl)phenol Chemical compound CCC(O)C1=CC=CC(O)=C1 ZWEWBWNQZUJOIF-UHFFFAOYSA-N 0.000 description 1
- QBXLGKAGMWXECL-UHFFFAOYSA-N 3-(2-hydroxypropyl)phenol Chemical compound CC(O)CC1=CC=CC(O)=C1 QBXLGKAGMWXECL-UHFFFAOYSA-N 0.000 description 1
- TVQDIGAZKJXXLX-UHFFFAOYSA-N 3-(3-hydroxypropyl)phenol Chemical compound OCCCC1=CC=CC(O)=C1 TVQDIGAZKJXXLX-UHFFFAOYSA-N 0.000 description 1
- SVORLQBKNKTJOV-UHFFFAOYSA-N 3-(chloromethyl)-4-(dimethylamino)butanenitrile Chemical compound CN(C)CC(CCl)CC#N SVORLQBKNKTJOV-UHFFFAOYSA-N 0.000 description 1
- UHZCXLUFPJDCQA-UHFFFAOYSA-N 3-(chloromethyl)-4-cyclopropylbutanenitrile Chemical compound N#CCC(CCl)CC1CC1 UHZCXLUFPJDCQA-UHFFFAOYSA-N 0.000 description 1
- XFNXKKGBNAKDHW-UHFFFAOYSA-N 3-(chloromethyl)-4-methoxybutanenitrile Chemical compound COCC(CCl)CC#N XFNXKKGBNAKDHW-UHFFFAOYSA-N 0.000 description 1
- GDONRPJGPFTIBH-UHFFFAOYSA-N 3-(chloromethyl)but-3-enenitrile Chemical compound ClCC(=C)CC#N GDONRPJGPFTIBH-UHFFFAOYSA-N 0.000 description 1
- TUFGRUYJSRQVKH-UHFFFAOYSA-N 3-(chloromethyl)hex-3-enenitrile Chemical compound CCC=C(CCl)CC#N TUFGRUYJSRQVKH-UHFFFAOYSA-N 0.000 description 1
- DSOGFOBIDOVCHN-UHFFFAOYSA-N 3-(chloromethyl)quinoline Chemical compound C1=CC=CC2=CC(CCl)=CN=C21 DSOGFOBIDOVCHN-UHFFFAOYSA-N 0.000 description 1
- VWFMIMNSQXLOHE-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methoxyphenol Chemical compound COC1=CC=C(O)C=C1CO VWFMIMNSQXLOHE-UHFFFAOYSA-N 0.000 description 1
- XBPRAIIIFOIDQE-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C=C1CO XBPRAIIIFOIDQE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- JJAFJTDYZBZDQM-UHFFFAOYSA-N 3-benzyl-4-chlorobutanenitrile Chemical compound N#CCC(CCl)CC1=CC=CC=C1 JJAFJTDYZBZDQM-UHFFFAOYSA-N 0.000 description 1
- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 description 1
- USFXKDONTUYBAU-UHFFFAOYSA-N 3-chlorobutanenitrile Chemical compound CC(Cl)CC#N USFXKDONTUYBAU-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- QGCCNWSXJHGUNL-UHFFFAOYSA-N 3-iodo-benzyl alcohol Chemical compound OCC1=CC=CC(I)=C1 QGCCNWSXJHGUNL-UHFFFAOYSA-N 0.000 description 1
- FXTKWBZFNQHAAO-UHFFFAOYSA-N 3-iodophenol Chemical compound OC1=CC=CC(I)=C1 FXTKWBZFNQHAAO-UHFFFAOYSA-N 0.000 description 1
- IPPQNXSAJZOTJZ-UHFFFAOYSA-N 3-methylsalicylaldehyde Chemical compound CC1=CC=CC(C=O)=C1O IPPQNXSAJZOTJZ-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
- DOFIAZGYBIBEGI-UHFFFAOYSA-N 3-sulfanylphenol Chemical compound OC1=CC=CC(S)=C1 DOFIAZGYBIBEGI-UHFFFAOYSA-N 0.000 description 1
- WEKMUBUZJDWJIR-UHFFFAOYSA-N 4-(1-hydroxypropyl)phenol Chemical compound CCC(O)C1=CC=C(O)C=C1 WEKMUBUZJDWJIR-UHFFFAOYSA-N 0.000 description 1
- RODZBUUMGRIALV-UHFFFAOYSA-N 4-(2-hydroxypropyl)phenol Chemical compound CC(O)CC1=CC=C(O)C=C1 RODZBUUMGRIALV-UHFFFAOYSA-N 0.000 description 1
- OLSKQWRLRYMCAO-UHFFFAOYSA-N 4-(chloromethyl)quinoline Chemical compound C1=CC=C2C(CCl)=CC=NC2=C1 OLSKQWRLRYMCAO-UHFFFAOYSA-N 0.000 description 1
- HSKGHUJMBLYPDO-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methylphenol Chemical compound CC1=CC(CO)=CC=C1O HSKGHUJMBLYPDO-UHFFFAOYSA-N 0.000 description 1
- IMPDSJJLYGGTPW-UHFFFAOYSA-N 4-(hydroxymethyl)-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1CO IMPDSJJLYGGTPW-UHFFFAOYSA-N 0.000 description 1
- MEIVQIJCALKJAE-UHFFFAOYSA-N 4-(hydroxymethyl)-3-methylphenol Chemical compound CC1=CC(O)=CC=C1CO MEIVQIJCALKJAE-UHFFFAOYSA-N 0.000 description 1
- JZYHHLHDFCMSLA-UHFFFAOYSA-N 4-chloro-2,3-dimethylpentanenitrile Chemical compound CC(Cl)C(C)C(C)C#N JZYHHLHDFCMSLA-UHFFFAOYSA-N 0.000 description 1
- VWYKSJIPZHRLNO-UHFFFAOYSA-N 4-chloro-2,6-dimethylphenol Chemical compound CC1=CC(Cl)=CC(C)=C1O VWYKSJIPZHRLNO-UHFFFAOYSA-N 0.000 description 1
- KTAUPADQJBKLBF-UHFFFAOYSA-N 4-chloro-3,3-dimethylpentanenitrile Chemical compound CC(Cl)C(C)(C)CC#N KTAUPADQJBKLBF-UHFFFAOYSA-N 0.000 description 1
- MMZMROHDQCJAJT-UHFFFAOYSA-N 4-chloro-4-oxobutanoic acid Chemical compound OC(=O)CCC(Cl)=O MMZMROHDQCJAJT-UHFFFAOYSA-N 0.000 description 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 1
- 125000004229 4H-chromen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(OC(*)=C([H])C2([H])[H])=C1[H] 0.000 description 1
- 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 description 1
- XGYCFBRLHVWRLV-UHFFFAOYSA-N 5-(hydroxymethyl)-2-methylphenol Chemical compound CC1=CC=C(CO)C=C1O XGYCFBRLHVWRLV-UHFFFAOYSA-N 0.000 description 1
- GWFUGTNHAGBOML-UHFFFAOYSA-N 5-(quinolin-2-ylmethoxy)pentan-1-ol Chemical compound C1=CC=CC2=NC(COCCCCCO)=CC=C21 GWFUGTNHAGBOML-UHFFFAOYSA-N 0.000 description 1
- NDMZZQRNZFWMEZ-UHFFFAOYSA-N 5-bromo-1h-pyridin-2-one Chemical compound OC1=CC=C(Br)C=N1 NDMZZQRNZFWMEZ-UHFFFAOYSA-N 0.000 description 1
- VTUDATOSQGYWML-UHFFFAOYSA-N 5-bromo-1h-pyrimidin-2-one Chemical compound OC1=NC=C(Br)C=N1 VTUDATOSQGYWML-UHFFFAOYSA-N 0.000 description 1
- BBGYMCKJHQIXLY-UHFFFAOYSA-N 5-chloro-4-methylpentanenitrile Chemical compound ClCC(C)CCC#N BBGYMCKJHQIXLY-UHFFFAOYSA-N 0.000 description 1
- JSAWFGSXRPCFSW-UHFFFAOYSA-N 5-chloropentanenitrile Chemical compound ClCCCCC#N JSAWFGSXRPCFSW-UHFFFAOYSA-N 0.000 description 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
- IIKRBPAOZJLVIR-UHFFFAOYSA-N 6-[3-(naphthalen-2-ylmethoxy)phenyl]hexanoic acid Chemical compound OC(=O)CCCCCC1=CC=CC(OCC=2C=C3C=CC=CC3=CC=2)=C1 IIKRBPAOZJLVIR-UHFFFAOYSA-N 0.000 description 1
- GYNUSHOPFHYCBG-UHFFFAOYSA-N 6-[3-[(1,3,3-trimethyl-2-oxoindol-6-yl)oxymethyl]phenyl]hexanoic acid Chemical compound C1=C2N(C)C(=O)C(C)(C)C2=CC=C1OCC1=CC=CC(CCCCCC(O)=O)=C1 GYNUSHOPFHYCBG-UHFFFAOYSA-N 0.000 description 1
- UMRPHASUHVKTMO-UHFFFAOYSA-N 6-[3-[[tert-butyl(diphenyl)silyl]oxymethyl]phenyl]hexan-1-ol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC1=CC=CC(CCCCCCO)=C1 UMRPHASUHVKTMO-UHFFFAOYSA-N 0.000 description 1
- XDTJPJTXMLGVNR-UHFFFAOYSA-N 6-[3-[[tert-butyl(diphenyl)silyl]oxymethyl]phenyl]hexanoic acid Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC1=CC=CC(CCCCCC(O)=O)=C1 XDTJPJTXMLGVNR-UHFFFAOYSA-N 0.000 description 1
- VHSCPQNPCSPACW-UHFFFAOYSA-N 6-bromo-2h-pyrazin-3-one Chemical compound BrC1=NCC(=O)N=C1 VHSCPQNPCSPACW-UHFFFAOYSA-N 0.000 description 1
- PLKNMBFMTVKLEW-UHFFFAOYSA-N 6-chlorohexanenitrile Chemical compound ClCCCCCC#N PLKNMBFMTVKLEW-UHFFFAOYSA-N 0.000 description 1
- OXOQGUGIJKUSRP-UHFFFAOYSA-N 6-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=C2CC(=O)NC2=C1 OXOQGUGIJKUSRP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 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 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- ACXASCLNDQMJPJ-UHFFFAOYSA-N C(C)(C)(C)[SiH2]OC(C=1C=C(C=CC1)CCCCCC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)(C)(C)[SiH2]OC(C=1C=C(C=CC1)CCCCCC(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1 ACXASCLNDQMJPJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 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
- 206010009944 Colon cancer Diseases 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical group C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 101100326341 Drosophila melanogaster brun gene Proteins 0.000 description 1
- 206010072268 Drug-induced liver injury Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 208000013875 Heart injury Diseases 0.000 description 1
- 208000016988 Hemorrhagic Stroke Diseases 0.000 description 1
- 101000979342 Homo sapiens Nuclear factor NF-kappa-B p105 subunit Proteins 0.000 description 1
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 1
- 101000741790 Homo sapiens Peroxisome proliferator-activated receptor gamma Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- 102000003746 Insulin Receptor Human genes 0.000 description 1
- 108010001127 Insulin Receptor Proteins 0.000 description 1
- 208000032382 Ischaemic stroke Diseases 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 208000004852 Lung Injury Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000028389 Nerve injury Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102100023050 Nuclear factor NF-kappa-B p105 subunit Human genes 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 108010044210 PPAR-beta Proteins 0.000 description 1
- 108091008768 PPARγ1 Proteins 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005864 Sulphur Substances 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
- 241001061127 Thione Species 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
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 206010069363 Traumatic lung injury Diseases 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 206010047513 Vision blurred Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002293 adipogenic effect Effects 0.000 description 1
- 210000003486 adipose tissue brown Anatomy 0.000 description 1
- 230000011759 adipose tissue development Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 230000000578 anorexic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000000778 atheroprotective effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 229960000516 bezafibrate Drugs 0.000 description 1
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- HZBOQOXQPRQKTF-UHFFFAOYSA-N bis(4-methylphenyl) 2,3-dihydroxybutanedioate Chemical class C1=CC(C)=CC=C1OC(=O)C(O)C(O)C(=O)OC1=CC=C(C)C=C1 HZBOQOXQPRQKTF-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 150000005752 bromopyridines Chemical class 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000006189 buccal tablet Substances 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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
- 230000007423 decrease Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 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
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 125000005072 dihydrothiopyranyl group Chemical group S1C(CCC=C1)* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- IONILKJMORGLHT-UHFFFAOYSA-N ethyl 2-(cyclohexylmethoxy)-6-methyl-4-phenylmethoxybenzoate Chemical compound C1=C(OCC2CCCCC2)C(C(=O)OCC)=C(C)C=C1OCC1=CC=CC=C1 IONILKJMORGLHT-UHFFFAOYSA-N 0.000 description 1
- KWXBNUYCDMPLEQ-UHFFFAOYSA-N ethyl 2-hydroxy-6-methylbenzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1O KWXBNUYCDMPLEQ-UHFFFAOYSA-N 0.000 description 1
- VESYBXQUEPVTOS-UHFFFAOYSA-N ethyl 3-(chloromethyl)-4-cyanobutanoate Chemical compound CCOC(=O)CC(CCl)CC#N VESYBXQUEPVTOS-UHFFFAOYSA-N 0.000 description 1
- CEEHFWSNEHHQPJ-UHFFFAOYSA-N ethyl 5-hydroxy-7-oxo-2-phenyl-8-prop-2-enylpyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=C2N(CC=C)C(=O)C(C(=O)OCC)=C(O)C2=CN=C1C1=CC=CC=C1 CEEHFWSNEHHQPJ-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- HDVRLUFGYQYLFJ-UHFFFAOYSA-N flamenol Chemical compound COC1=CC(O)=CC(O)=C1 HDVRLUFGYQYLFJ-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 230000004190 glucose uptake Effects 0.000 description 1
- 210000002503 granulosa cell Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 102000054223 human PPARA Human genes 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000000222 hyperoxic effect Effects 0.000 description 1
- 230000000999 hypotriglyceridemic effect Effects 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 208000020658 intracerebral hemorrhage Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 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
- 150000002615 leukotriene B4 derivatives Chemical class 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-M leukotriene B4(1-) Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC([O-])=O VNYSSYRCGWBHLG-AMOLWHMGSA-M 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229960003646 lysine Drugs 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GIJIKNIHYNIDSJ-UHFFFAOYSA-N methyl 1-benzofuran-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=CC2=C1 GIJIKNIHYNIDSJ-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004457 myocytus nodalis Anatomy 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- BEWMMIJYSRELRT-UHFFFAOYSA-N n-(4-hydroxybutyl)-n-(quinolin-2-ylmethyl)acetamide Chemical compound C1=CC=CC2=NC(CN(CCCCO)C(=O)C)=CC=C21 BEWMMIJYSRELRT-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WWIFXRIEPIGRDO-UHFFFAOYSA-N n-methyl-2-phenyl-n-(2-phenylethyl)acetamide Chemical class C=1C=CC=CC=1CC(=O)N(C)CCC1=CC=CC=C1 WWIFXRIEPIGRDO-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 235000020830 overeating Nutrition 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 150000003176 prostaglandin J2 derivatives Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical class [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003893 regulation of appetite Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 230000000250 revascularization Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 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
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical group 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 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
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13145599P | 1999-04-28 | 1999-04-28 | |
PCT/US2000/011833 WO2000064888A1 (en) | 1999-04-28 | 2000-04-28 | Di-aryl acid derivatives as ppar receptor ligands |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20010795A2 true HRP20010795A2 (en) | 2003-02-28 |
Family
ID=22449544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20010795A HRP20010795A2 (en) | 1999-04-28 | 2001-10-26 | Di-aryl acid derivatives as ppar receptor ligands |
Country Status (28)
Country | Link |
---|---|
US (2) | US6635655B1 (es) |
EP (1) | EP1177187B1 (es) |
JP (1) | JP4598278B2 (es) |
KR (1) | KR100709498B1 (es) |
CN (2) | CN101070316A (es) |
AT (1) | ATE368037T1 (es) |
AU (1) | AU781266B2 (es) |
BR (1) | BR0010605A (es) |
CA (1) | CA2370250C (es) |
CZ (1) | CZ20013833A3 (es) |
DE (1) | DE60035682T2 (es) |
DK (1) | DK1177187T3 (es) |
EE (1) | EE200100556A (es) |
ES (1) | ES2287016T3 (es) |
HK (1) | HK1045515B (es) |
HR (1) | HRP20010795A2 (es) |
HU (1) | HUP0201291A3 (es) |
IL (2) | IL145922A0 (es) |
MX (1) | MXPA01010880A (es) |
NO (1) | NO323643B1 (es) |
NZ (1) | NZ515086A (es) |
PL (1) | PL196957B1 (es) |
PT (1) | PT1177187E (es) |
RU (1) | RU2267484C2 (es) |
SK (1) | SK15532001A3 (es) |
WO (1) | WO2000064888A1 (es) |
YU (1) | YU72201A (es) |
ZA (1) | ZA200108798B (es) |
Families Citing this family (224)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000064876A1 (en) | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
US6503949B1 (en) * | 1999-05-17 | 2003-01-07 | Noro Nordisk A/S | Glucagon antagonists/inverse agonists |
EP1206464A4 (en) * | 1999-08-23 | 2002-12-18 | Smithkline Beecham Corp | FATTY ACID SYNTHASE INHIBITORS |
US6414002B1 (en) | 1999-09-22 | 2002-07-02 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
TWI302149B (en) | 1999-09-22 | 2008-10-21 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
KR20020081424A (ko) * | 2000-03-09 | 2002-10-26 | 아벤티스 파마 도이칠란트 게엠베하 | Ppar 매개인자의 치료학적 용도 |
JP2001261654A (ja) * | 2000-03-21 | 2001-09-26 | Mitsui Chemicals Inc | キノリン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
PE20020665A1 (es) | 2000-06-15 | 2002-08-14 | Pharmacia Corp | ACIDO CICLOALQUIL FENIL ALCANOICO COMO ANTAGONISTA DE INTEGRINAS OVß3 |
US6531494B1 (en) | 2001-08-29 | 2003-03-11 | Pharmacia Corporation | Gem-substituted αvβ3 antagonists |
HN2001000224A (es) | 2000-10-19 | 2002-06-13 | Pfizer | Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos. |
WO2002064632A2 (en) * | 2001-02-01 | 2002-08-22 | Smithkline Beecham Corporation | Crystallized ppar$g(a) ligand binding domain polypeptide and screening methods employing same |
WO2002079162A1 (fr) * | 2001-03-28 | 2002-10-10 | Eisai Co., Ltd. | Acides carboxyliques |
WO2002081428A1 (fr) | 2001-03-30 | 2002-10-17 | Eisai Co., Ltd. | Compose de benzene et sel de ce compose |
TWI311133B (en) | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
EP1387713A1 (en) * | 2001-05-04 | 2004-02-11 | Pfizer Products Inc. | Method of preventing type 2 diabetes with aerosolized insulin |
GB0111523D0 (en) * | 2001-05-11 | 2001-07-04 | Glaxo Group Ltd | Chemical compounds |
JPWO2002098840A1 (ja) | 2001-06-04 | 2004-09-16 | エーザイ株式会社 | カルボン酸誘導体及びその塩もしくはそのエステルからなる医薬 |
JP4399253B2 (ja) | 2001-06-20 | 2010-01-13 | ワイス | プラスミノゲンアクチベーターインヒビター−1(pai−1)のインヒビターとしての、置換されたインドール酸誘導体 |
TWI224101B (en) | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
WO2003006022A1 (en) * | 2001-07-09 | 2003-01-23 | Dr. Reddy's Laboratories Ltd. | Tetrahydroquinoline derivatives and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
US20110065129A1 (en) | 2001-07-27 | 2011-03-17 | Lowe Derek B | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
AR036237A1 (es) | 2001-07-27 | 2004-08-25 | Bayer Corp | Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento |
US6869967B2 (en) | 2001-07-30 | 2005-03-22 | Novo Nordisk A/S | Peroxisome proliferator-activated receptor (PPAR) active vinyl carboxylic acid derivatives |
WO2003016265A1 (fr) * | 2001-08-17 | 2003-02-27 | Eisai Co., Ltd. | Compose cyclique et agoniste du recepteur ppar |
US7399777B2 (en) | 2001-08-31 | 2008-07-15 | Sanofi-Aventis Deutschland Gmbh | Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmceuticals |
CA2458210C (en) | 2001-08-31 | 2011-09-20 | Aventis Pharma Deutschland Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as ppar-activators |
US6884812B2 (en) | 2001-08-31 | 2005-04-26 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmaceuticals |
AR037097A1 (es) | 2001-10-05 | 2004-10-20 | Novartis Ag | Compuestos acilsulfonamidas, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de un medicamento |
TW200303742A (en) | 2001-11-21 | 2003-09-16 | Novartis Ag | Organic compounds |
UA82835C2 (en) | 2001-12-03 | 2008-05-26 | Reddys Lab Ltd Dr | ?-aryl-?-oxysubstituted propionuc acid derivatives and pharmaceutical composition based thereon |
SE0104333D0 (sv) * | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
GB0229931D0 (en) | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
GB0314079D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
US20050250831A1 (en) * | 2002-02-21 | 2005-11-10 | Gibson Tracey A | Peroxisome proliferator activated receptor modulators |
US6716842B2 (en) | 2002-04-05 | 2004-04-06 | Warner-Lambert Company, Llc | Antidiabetic agents |
US7223796B2 (en) | 2002-04-11 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Acyl-4-carboxyphenylurea derivatives, processes for preparing them and their use |
US7078404B2 (en) | 2002-04-11 | 2006-07-18 | Sanofi-Aventis Deutschland Gmbh | Acyl-3-carboxyphenylurea derivatives, processes for preparing them and their use |
MXPA04009961A (es) | 2002-04-12 | 2004-12-13 | Pfizer | Compuestos de imidazol como agentes anti-inflamatorios y analgesicos. |
MXPA04009960A (es) * | 2002-04-12 | 2004-12-13 | Pfizer | Compuestos de pirazol como agentes anti-inflamatorios y analgesicos. |
US7049341B2 (en) | 2002-06-07 | 2006-05-23 | Aventis Pharma Deutschland Gmbh | N-benzoylureidocinnamic acid derivatives, processes for preparing them and their use |
US7351858B2 (en) | 2002-06-20 | 2008-04-01 | Astrazeneca Ab | Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance |
ATE386013T1 (de) | 2002-06-20 | 2008-03-15 | Astrazeneca Ab | Ortho-substituierte benzoesäurederivate zur behandlung von insulinresistenz |
SE0201937D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
ES2261556T3 (es) * | 2002-06-21 | 2006-11-16 | Prime European Therapeuticals S.P.A. (Euticals S.P.A.) | Acido 2-bromometil-6-benzoico y un procedimiento para la prepararacion del mismo. |
PL374860A1 (en) | 2002-07-09 | 2005-11-14 | Bristol-Myers Squibb Company | Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method |
AU2003281040A1 (en) * | 2002-07-10 | 2004-02-02 | Sumitomo Pharmaceuticals Co., Ltd. | Biaryl derivatives |
US7262220B2 (en) | 2002-07-11 | 2007-08-28 | Sanofi-Aventis Deutschland Gmbh | Urea- and urethane-substituted acylureas, process for their preparation and their use |
DE10231370B4 (de) | 2002-07-11 | 2006-04-06 | Sanofi-Aventis Deutschland Gmbh | Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
MXPA05000053A (es) | 2002-07-12 | 2005-04-08 | Aventis Pharma Gmbh | Benzoilureas heterociclicamente sustituidas, metodo para su produccion y su uso como medicamentos. |
US7078423B2 (en) | 2002-07-18 | 2006-07-18 | Inotek Pharmaceuticals Corporation | 5-Aryltetrazole compounds, compositions thereof, and uses therefor |
US7087631B2 (en) | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
CN1688540A (zh) * | 2002-09-05 | 2005-10-26 | 诺沃挪第克公司 | 新颖的乙烯基羧酸衍生物以及它们的治疗用途 |
JP2004123732A (ja) * | 2002-09-10 | 2004-04-22 | Takeda Chem Ind Ltd | 5員複素環化合物 |
US20040157922A1 (en) | 2002-10-04 | 2004-08-12 | Aventis Pharma Deutschland Gmbh | Carboxyalkoxy-substituted acyl-carboxyphenylurea derivatives and their use as medicaments |
US7208504B2 (en) | 2002-10-12 | 2007-04-24 | Sanofi-Aventis Deutschland Gmbh | Bicyclic inhibitors of hormone sensitive lipase |
KR20050055790A (ko) * | 2002-10-28 | 2005-06-13 | 노보 노르디스크 에이/에스 | Ppar 매개 질환의 치료에 유용한 신규 화합물 |
WO2004048341A1 (ja) * | 2002-11-28 | 2004-06-10 | Sumitomo Pharmaceuticals Co., Ltd. | 新規ヘテロアリール誘導体 |
DE60324183D1 (en) | 2002-12-10 | 2008-11-27 | Wyeth Corp | Aryl-, aryloxy- und alkyloxysubstituierte 1h-indol-3-yl-glyoxylsäurederivateals inhibitoren des plasminogenaktivatorinhibitors-1 (pai-1) |
DE60306548T2 (de) | 2002-12-10 | 2007-06-21 | Wyeth | Substituierte 3-carbonyl-1-yl-essigsäure-derivate als plasminogen aktivator inhibitor(pai-1) inhibitoren |
UA80453C2 (en) | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
DE60306547T2 (de) | 2002-12-10 | 2007-06-28 | Wyeth | Substituierte 3-alkyl- und 3-arylalkyl-1h-indol-1-yl-essigsäure-derivate als plasminogen-aktivator |
DE10258007B4 (de) | 2002-12-12 | 2006-02-09 | Sanofi-Aventis Deutschland Gmbh | Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel |
US6653334B1 (en) * | 2002-12-27 | 2003-11-25 | Kowa Co., Ltd. | Benzoxazole compound and pharmaceutical composition containing the same |
US6794401B2 (en) | 2003-01-17 | 2004-09-21 | Bexel Pharmaceuticals, Inc. | Amino acid phenoxy ethers |
US7521465B2 (en) | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
US7781464B2 (en) | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
US7179941B2 (en) | 2003-01-23 | 2007-02-20 | Sanofi-Aventis Deutschland Gmbh | Carbonylamino-substituted acyl phenyl urea derivatives, process for their preparation and their use |
WO2004073606A2 (en) * | 2003-02-14 | 2004-09-02 | Eli Lilly And Company | Sulfonamide derivatives as ppar modulators |
US7196114B2 (en) | 2003-02-17 | 2007-03-27 | Sanofi-Aventis Deutschland Gmbh | Substituted 3-(benzoylureido) thiophene derivatives, processes for preparing them and their use |
DE10308353A1 (de) | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US7148246B2 (en) | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
DE10308351A1 (de) | 2003-02-27 | 2004-11-25 | Aventis Pharma Deutschland Gmbh | 1,3-substituierte Cycloalkylderivate mit sauren, meist heterocyclischen Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE10308352A1 (de) | 2003-02-27 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Arylcycloalkylderivate mit verzweigten Seitenketten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
DE10308355A1 (de) | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
US7501440B2 (en) | 2003-03-07 | 2009-03-10 | Sanofi-Aventis Deutschland Gmbh | Substituted benzoylureidopyridylpiperidine-and-pyrrolidinecarboxylic acid derivatives, processes for preparing them and their use |
US6989462B2 (en) | 2003-03-25 | 2006-01-24 | Sanofi-Aventis Deutschland Gmbh | Synthesis of 2-chloromethyl-6-methylbenzoic ester |
DE10313228A1 (de) * | 2003-03-25 | 2004-10-21 | Aventis Pharma Deutschland Gmbh | Synthese von 2-Chlormethyl-6-methylbenzoesäureestern |
DE10314610A1 (de) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | Neues Diphenylazetidinon mit verbesserten physiologischen Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindungen enthaltende Arzneimittel und dessen Verwendung |
CA2521135A1 (en) * | 2003-04-07 | 2004-10-28 | Kalypsys, Inc. | N-containing heteroaromatic compounds as modulators of ppars and methods of treating metabolic disorders |
US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
JP2006525329A (ja) | 2003-04-30 | 2006-11-09 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | 置換カルボン酸類 |
TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
JP2009513523A (ja) | 2003-07-08 | 2009-04-02 | ノバルティス アクチエンゲゼルシャフト | ベンゼンスルホニルアミノ化合物およびそれらを含む医薬組成物 |
RU2356889C2 (ru) | 2003-07-17 | 2009-05-27 | Плекссикон, Инк. | Соединения, являющиеся активными по отношению к рецепторам, активируемым пролифератором пероксисом |
US7348338B2 (en) * | 2003-07-17 | 2008-03-25 | Plexxikon, Inc. | PPAR active compounds |
US7094800B2 (en) | 2003-07-25 | 2006-08-22 | Sanofi-Aventis Deutschland Gmbh | Cyanopyrrolidides, process for their preparation and their use as medicaments |
US7008957B2 (en) | 2003-07-25 | 2006-03-07 | Sanofi-Aventis Deutschland Gmbh | Bicyclic cyanoheterocycles, process for their preparation and their use as medicaments |
US7094794B2 (en) | 2003-07-28 | 2006-08-22 | Sanofi-Aventis Deutschland Gmbh | Substituted thiazole-benzoisothiazole dioxide derivatives, process for their preparation and their use |
DE10335092B3 (de) | 2003-08-01 | 2005-02-03 | Aventis Pharma Deutschland Gmbh | Substituierte Benzoylureido-o-benzoylamide, Verfahren zu deren Herstellung und deren Verwendung |
US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
US7442805B2 (en) | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
US7087576B2 (en) | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
JP2007527416A (ja) | 2003-10-31 | 2007-09-27 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ペルオキシソーム増殖因子活性化受容体(ppar)二重作動薬として有用なフェノキシ酢酸誘導体 |
AU2004293013B2 (en) | 2003-11-19 | 2011-04-28 | Metabasis Therapeutics, Inc. | Novel phosphorus-containing thyromimetics |
US7470706B2 (en) | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
US7498341B2 (en) | 2004-01-31 | 2009-03-03 | Sanofi Aventis Deutschland Gmbh | Heterocyclically substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
DE102004005172A1 (de) * | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
DE602004004631D1 (de) | 2004-04-01 | 2007-03-22 | Sanofi Aventis Deutschland | Oxadiazolone, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pharmazeutika |
US7297817B2 (en) * | 2004-04-13 | 2007-11-20 | Cephalon France | Thio-substituted arylmethanesulfinyl derivatives |
CA2575039A1 (en) * | 2004-08-11 | 2006-02-16 | Kyorin Pharmaceutical Co., Ltd. | Novel cyclic amino benzoic acid derivative |
CN101039936A (zh) | 2004-08-23 | 2007-09-19 | 惠氏公司 | 作为i-型纤溶酶原激活剂抑制剂(pai-1)调节剂用于治疗血栓形成和心血管疾病的唑基-萘基酸 |
DE102004046623A1 (de) * | 2004-09-25 | 2006-03-30 | Bayer Healthcare Ag | Neue Pyrimidin-Derivate und ihre Verwendung |
AU2005302475A1 (en) * | 2004-10-28 | 2006-05-11 | The Institutes For Pharmaceutical Discovery, Llc | Substituted phenylalkanoic acids |
CA2588953A1 (en) * | 2004-11-30 | 2006-06-08 | Plexxikon, Inc. | Ppar active compounds |
EP1671633A1 (en) | 2004-12-17 | 2006-06-21 | Sanofi-Aventis Deutschland GmbH | Use of PPAR agonists for the treatment of congestive heart failure |
NZ555982A (en) | 2004-12-30 | 2011-01-28 | Astex Therapeutics Ltd | Pyrazole compounds that modulate the activity of CDK, GSK and aurora kinases |
US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
JPWO2006075638A1 (ja) * | 2005-01-14 | 2008-06-12 | 大日本住友製薬株式会社 | 新規ヘテロアリール誘導体 |
DE102005027150A1 (de) * | 2005-03-12 | 2006-09-28 | Bayer Healthcare Ag | Pyrimidincarbonsäure-Derivate und ihre Verwendung |
CN101189231B (zh) * | 2005-03-23 | 2011-05-18 | 杏林制药株式会社 | 环状氨基苯基链烷酸衍生物 |
WO2006129164A1 (en) | 2005-05-31 | 2006-12-07 | Pfizer Japan Inc. | Substituted aryloxy-n-bicyclomethyl acetamide compounds as vr1 antagonists |
DE102005026762A1 (de) | 2005-06-09 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Azolopyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen |
DE102005029382B3 (de) * | 2005-06-24 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Alkoxymethylyl-substituierte Benzoesäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
CA2613522A1 (en) | 2005-06-27 | 2007-01-04 | Exelixis, Inc. | Imidazole based lxr modulators |
US8410109B2 (en) | 2005-07-29 | 2013-04-02 | Resverlogix Corp. | Pharmaceutical compositions for the prevention and treatment of complex diseases and their delivery by insertable medical devices |
US7754717B2 (en) * | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
CN101263115A (zh) | 2005-08-17 | 2008-09-10 | 惠氏公司 | 经取代吲哚和其用途 |
AU2006287528A1 (en) * | 2005-09-07 | 2007-03-15 | Plexxikon, Inc. | 1 , 4 and 1 , 5-disubstituted indole derivatives for use as PPAR active compounds |
WO2007030567A2 (en) * | 2005-09-07 | 2007-03-15 | Plexxikon, Inc. | Pparactive compounds |
CA2621474A1 (en) * | 2005-09-07 | 2007-03-15 | Plexxikon, Inc. | 1,3-disubstituted indole derivatives for use as ppar modulators |
CN101272784A (zh) | 2005-09-29 | 2008-09-24 | 塞诺菲-安万特股份有限公司 | 苯基-和吡啶基-1,2,4-噁二唑酮衍生物、它们的制备方法和它们作为药物的用途 |
EP1968579A1 (en) | 2005-12-30 | 2008-09-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
FR2902789A1 (fr) * | 2006-06-21 | 2007-12-28 | Genfit Sa | Derives de 1,3-diphenylpropane substitues, preparations et utilisations |
DE102006028862A1 (de) | 2006-06-23 | 2007-12-27 | Merck Patent Gmbh | 3-Amino-imidazo[1,2-a]pyridinderivate |
JP5523829B2 (ja) | 2006-06-29 | 2014-06-18 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
JP2010510202A (ja) | 2006-11-17 | 2010-04-02 | ファイザー株式会社 | 置換ビシクロカルボキシアミド化合物 |
KR20090094125A (ko) | 2006-12-08 | 2009-09-03 | 엑셀리시스, 인코포레이티드 | Lxr 및 fxr 조절자 |
DE102007002260A1 (de) | 2007-01-16 | 2008-07-31 | Sanofi-Aventis | Verwendung von substituierten Pyranonsäurederivaten zur Herstellung von Medikamenten zur Behandlung des Metabolischen Syndroms |
DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
WO2008092231A1 (en) | 2007-02-01 | 2008-08-07 | Resverlogix Corp. | Compounds for the prevention and treatment of cardiovascular diseases |
DE102007008420A1 (de) | 2007-02-21 | 2008-08-28 | Merck Patent Gmbh | Benzimidazolderivate |
PE20090159A1 (es) * | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
CN101381302B (zh) * | 2007-09-07 | 2013-04-03 | 上海睿智化学研究有限公司 | 2-溴甲基-6-甲基苯甲酰氯/溴的制备方法 |
WO2009042435A1 (en) | 2007-09-21 | 2009-04-02 | Array Biopharma Inc. | Pyridin-2 -yl-amino-i, 2, 4 -thiadiazole derivatives as glucokinase activators for the treatment of diabetes mellitus |
CA2700088A1 (en) * | 2007-09-26 | 2009-04-02 | Astellas Pharma Inc. | Quinolone derivative |
DE102007048716A1 (de) | 2007-10-11 | 2009-04-23 | Merck Patent Gmbh | Imidazo[1,2-a]pyrimidinderivate |
DE102007063671A1 (de) | 2007-11-13 | 2009-06-25 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
AU2008338963A1 (en) * | 2007-12-13 | 2009-06-25 | Sri International | PPAR-delta ligands and methods of their use |
DE102008017590A1 (de) | 2008-04-07 | 2009-10-08 | Merck Patent Gmbh | Glucopyranosidderivate |
DE102008018675A1 (de) | 2008-04-14 | 2009-10-15 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Carbonsäure-Derivate und ihre Verwendung |
AU2009262252B2 (en) | 2008-06-26 | 2013-05-02 | Resverlogix Corp. | Methods of preparing quinazolinone derivatives |
TW201014822A (en) | 2008-07-09 | 2010-04-16 | Sanofi Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
MX354134B (es) | 2008-07-23 | 2018-02-14 | Arena Pharm Inc | Derivados de acido 1,2,3,4-tetrahidrociclopenta [b] indol-3-il) acetico sustituidos utiles en el tratamiento de enfermedades autoinmune e inflamatorias. |
CA2733671C (en) | 2008-08-27 | 2018-01-02 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
ES2463097T3 (es) | 2009-01-08 | 2014-05-27 | Resverlogix Corp. | Compuestos para la prevención y el tratamiento de enfermedades cardiovasculares |
US20120046364A1 (en) | 2009-02-10 | 2012-02-23 | Metabasis Therapeutics, Inc. | Novel Sulfonic Acid-Containing Thyromimetics, and Methods for Their Use |
DE102009012314A1 (de) | 2009-03-09 | 2010-09-16 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Alkylcarbonsäuren und ihre Verwendung |
JP5795304B2 (ja) | 2009-03-18 | 2015-10-14 | レスバーロジックス コーポレイション | 新規抗炎症剤 |
KR102215167B1 (ko) | 2009-04-22 | 2021-02-16 | 리스버로직스 코퍼레이션 | 신규한 소염제 |
CN102573473B (zh) | 2009-06-09 | 2015-05-27 | 加利福尼亚资本权益有限责任公司 | 用作hedgehog 信号转导抑制剂的异喹啉、喹啉和喹唑啉衍生物 |
US8877924B2 (en) | 2009-06-09 | 2014-11-04 | NantBio Inc. | Benzyl substituted triazine derivatives and their therapeutical applications |
AU2010258853B2 (en) | 2009-06-09 | 2014-07-31 | Nantbio, Inc. | Triazine derivatives and their therapeutical applications |
SG178880A1 (en) | 2009-08-26 | 2012-04-27 | Sanofi Sa | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
CN103539785B (zh) | 2009-08-28 | 2015-09-23 | 艾尼纳制药公司 | ***素受体调节剂 |
BR112012007349A2 (pt) | 2009-10-02 | 2019-09-24 | Sanofi Sa | uso de composto com atividade inibidora de sglt-1/sglt-2 para produção de medicamentos para tratamento de doenças ósseas. |
DE102009046115A1 (de) | 2009-10-28 | 2011-09-08 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 3-Phenylpropansäuren und ihre Verwendung |
EP4148045A1 (en) | 2010-01-27 | 2023-03-15 | Arena Pharmaceuticals, Inc. | Intermediate compounds for the preparation of (r)-2-(7-(4-cyclopentyl-3- (trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl)acetic acid and salts thereof |
WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
SG10201501575VA (en) | 2010-03-03 | 2015-04-29 | Arena Pharm Inc | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
DE102011006974A1 (de) | 2011-04-07 | 2012-10-11 | Bayer Pharma Aktiengesellschaft | Substituierte 1-Benzylcycloalkylcarbonsäuren und ihre Verwendung |
CA2819880C (en) | 2010-12-07 | 2019-01-22 | Bayer Intellectual Property Gmbh | Substituted 1-benzylcycloalkylcarboxlic acids and use thereof |
DE102010062544A1 (de) | 2010-12-07 | 2012-06-14 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 1-Benzylcycloalkylcarbonsäuren und ihre Verwendung |
MX2013006768A (es) | 2010-12-23 | 2013-07-22 | Pfizer | Moduladores de receptor de glucagon. |
IL227559A (en) | 2011-02-08 | 2016-04-21 | Pfizer | Glucagon receptor modulator |
MX346644B (es) | 2011-02-25 | 2017-03-14 | Arena Pharm Inc | Moduladores de receptores canabinoides. |
US9597340B2 (en) | 2011-02-25 | 2017-03-21 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
ES2932441T3 (es) | 2011-02-25 | 2023-01-19 | Arena Pharm Inc | Formas cristalinas y procesos para la preparación de azaciclos condensados (moduladores de los receptores cannabinoides) |
WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
DE102011007272A1 (de) | 2011-04-13 | 2012-10-18 | Bayer Pharma Aktiengesellschaft | Verzweigte 3-Phenylpropionsäure-Derivate und ihre Verwendung |
KR20140023441A (ko) | 2011-07-22 | 2014-02-26 | 화이자 인코포레이티드 | 퀴놀린일 글루카곤 수용체 조절제 |
WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
US9207002B2 (en) | 2011-10-12 | 2015-12-08 | International Business Machines Corporation | Contaminant separator for a vapor-compression refrigeration apparatus |
US8713955B2 (en) * | 2011-10-12 | 2014-05-06 | International Business Machines Corporation | Intra-condenser contaminant extractor for a vapor-compression refrigeration apparatus |
PT2773354T (pt) | 2011-11-01 | 2019-07-17 | Resverlogix Corp | Formulações orais de libertação imediata para quinazolinonas substituídas |
DE102012208530A1 (de) | 2012-05-22 | 2013-11-28 | Bayer Pharma AG | Substituierte Piperidinoacetamide und ihre Verwendung |
US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
WO2014080290A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Cyclic amines as bromodomain inhibitors |
WO2014096965A2 (en) | 2012-12-21 | 2014-06-26 | Rvx Therapeutics Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
EP2961746B1 (en) | 2013-02-28 | 2018-01-03 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效rock1及rock2抑制劑之苯基吡唑衍生物 |
ES2654161T3 (es) | 2013-05-28 | 2018-02-12 | Astrazeneca Ab | Compuestos químicos |
PT3057964T (pt) | 2013-10-14 | 2020-02-25 | Eisai R&D Man Co Ltd | Compostos de quinolina seletivamente substituídos |
JP6483666B2 (ja) | 2013-10-14 | 2019-03-13 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
EP3268007B1 (en) | 2015-03-13 | 2022-11-09 | Resverlogix Corp. | Compositions and therapeutic methods for the treatment of complement-associated diseases |
IL285890B (en) | 2015-06-22 | 2022-07-01 | Arena Pharm Inc | Slate-free crystal of the arginine salt of (Ar)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-4,3,2,1-tetrahydro-cyclopent[b]indole-3-yl ) acetic acid |
CN105037279B (zh) * | 2015-06-25 | 2017-11-03 | 贵州大学 | 含戊二烯酮结构的4‑n取代喹唑啉类衍生物及制备和应用 |
SG11201811161YA (en) | 2016-07-14 | 2019-01-30 | Pfizer | Novel pyrimidine carboxamides as inhibitors of vanin-1 enzyme |
EP3484528B1 (en) | 2016-07-18 | 2020-11-25 | Janssen Pharmaceutica NV | Tau pet imaging ligands |
CN107796791B (zh) * | 2016-08-31 | 2020-08-25 | 陕西师范大学 | 一种基于氧化石墨烯筛选Rev多肽小分子拮抗剂的方法 |
ES2862374T3 (es) | 2016-12-28 | 2021-10-07 | Minoryx Therapeutics S L | Compuestos de isoquinolina, métodos para su preparación y usos terapéuticos de los mismos en afecciones asociadas con la alteración de la actividad de beta galactosidasa |
US11534424B2 (en) | 2017-02-16 | 2022-12-27 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
US11478448B2 (en) | 2017-02-16 | 2022-10-25 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
KR102648947B1 (ko) | 2017-04-26 | 2024-03-18 | 바실리어 파마슈티카 인터내셔널 리미티드 | 푸라자노벤즈이미다졸 및 이의 결정 형태의 제조 공정 |
CN108658908B (zh) | 2017-07-31 | 2019-05-10 | 广州必贝特医药技术有限公司 | 1,3-二取代烯酮类化合物及其应用 |
FI3749669T3 (fi) | 2018-02-06 | 2023-05-26 | Ideaya Biosciences Inc | AHR-modulaattoreita |
WO2019175464A1 (en) | 2018-03-14 | 2019-09-19 | Orion Corporation | Compounds useful as inhibitors of sodium-calcium exchanger (ncx) |
US10905667B2 (en) | 2018-07-24 | 2021-02-02 | Bayer Pharma Aktiengesellschaft | Orally administrable modified-release pharmaceutical dosage form |
US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
JP2023509452A (ja) | 2020-01-03 | 2023-03-08 | バーグ エルエルシー | がんを処置するためのube2kモジュレータとしての多環式アミド |
WO2021169769A1 (zh) * | 2020-02-28 | 2021-09-02 | 四川科伦博泰生物医药股份有限公司 | 芳香族化合物及其药物组合物和用途 |
EP4334298A1 (en) | 2021-06-14 | 2024-03-13 | Scorpion Therapeutics, Inc. | Urea derivatives which can be used to treat cancer |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4794188A (en) * | 1982-12-01 | 1988-12-27 | Usv Pharmaceutical Corporation | Certain unsymmetrical quinolinyl ethers having anti-inflammatory and anti-allergic activity |
CS248922B1 (cs) | 1984-11-28 | 1987-03-12 | Jitka Kahovcova | Smíšený ester kyseliny jantarové s 1-(2,2-dimethyl-2H-chromen- -6-yl)-1-alkanolem a Vl4-{6,7-epoxy-3,7-dimethyloktyloxy)fenyl]- -1-alkanolem a způsob jeho přípravy |
JPS63503139A (ja) * | 1986-03-13 | 1988-11-17 | ローラー インターナショナル(オーバーシーズ)インコーポレーテッド | 高血圧疾患治療剤としてのキノリニルエ−テル又はチオエ−テルテトラゾ−ル類 |
US4920132A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
GB9113628D0 (en) * | 1991-06-25 | 1991-08-14 | Ici Plc | Heterocyclic derivatives |
ATE167181T1 (de) * | 1993-12-09 | 1998-06-15 | Ono Pharmaceutical Co | Naphthylessigsäurederivate als pgez agonisten und antagonisten |
JP3909864B2 (ja) * | 1995-07-26 | 2007-04-25 | 小野薬品工業株式会社 | ナフチルオキシ酢酸誘導体およびそれらを有効成分として含有する薬剤 |
JPH09221473A (ja) * | 1995-10-30 | 1997-08-26 | Kissei Pharmaceut Co Ltd | 3−ヒドロキシ−4−アミノメチルピリジン誘導体およびそれらを含有するメイラード反応阻害剤 |
AU719146B2 (en) * | 1996-02-02 | 2000-05-04 | Merck & Co., Inc. | Antidiabetic agents |
WO1997027847A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
DE69720429T9 (de) * | 1996-02-02 | 2004-09-23 | Merck & Co., Inc. | Heterocyclische verbindungen als antidiabetische mittel und für die behandlung von fettleibigkeit |
WO1997028149A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
JP2001511767A (ja) * | 1996-12-23 | 2001-08-14 | メルク エンド カンパニー インコーポレーテッド | 糖尿病薬 |
AU8750298A (en) * | 1997-08-28 | 1999-03-22 | Ono Pharmaceutical Co. Ltd. | Peroxisome proliferator-activated receptor controllers |
WO1999015520A1 (fr) * | 1997-09-19 | 1999-04-01 | Ono Pharmaceutical Co., Ltd. | Composes de benzene fusionnes ou non fusionnes |
BR9814087A (pt) | 1997-10-17 | 2000-10-03 | Aventis Pharm Prod Inc | Processos para mediar a atividade do receptor de ppar-gama, e para tratar uma condição fisiológica em um paciente |
CN1280574A (zh) * | 1997-10-27 | 2001-01-17 | 雷迪研究基金会 | 新的杂环化合物及其在医药中的应用、它们的制备方法和含有它们的药物组合物 |
DE69828445D1 (de) * | 1998-04-23 | 2005-02-03 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
ES2347428T3 (es) * | 1999-02-01 | 2010-10-29 | EISAI R&D MANAGEMENT CO., LTD. | Compuestos coadyuvantes inmunologicos. |
WO2000064876A1 (en) | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
-
2000
- 2000-04-28 DE DE60035682T patent/DE60035682T2/de not_active Expired - Lifetime
- 2000-04-28 NZ NZ515086A patent/NZ515086A/en unknown
- 2000-04-28 WO PCT/US2000/011833 patent/WO2000064888A1/en active IP Right Grant
- 2000-04-28 CN CNA2007101121732A patent/CN101070316A/zh active Pending
- 2000-04-28 BR BR0010605-4A patent/BR0010605A/pt active Search and Examination
- 2000-04-28 AT AT00928698T patent/ATE368037T1/de not_active IP Right Cessation
- 2000-04-28 CA CA002370250A patent/CA2370250C/en not_active Expired - Fee Related
- 2000-04-28 KR KR1020017013757A patent/KR100709498B1/ko not_active IP Right Cessation
- 2000-04-28 YU YU72201A patent/YU72201A/sh unknown
- 2000-04-28 JP JP2000614240A patent/JP4598278B2/ja not_active Expired - Fee Related
- 2000-04-28 SK SK1553-2001A patent/SK15532001A3/sk unknown
- 2000-04-28 MX MXPA01010880A patent/MXPA01010880A/es active IP Right Grant
- 2000-04-28 PT PT00928698T patent/PT1177187E/pt unknown
- 2000-04-28 EP EP00928698A patent/EP1177187B1/en not_active Expired - Lifetime
- 2000-04-28 HU HU0201291A patent/HUP0201291A3/hu unknown
- 2000-04-28 RU RU2001132080/04A patent/RU2267484C2/ru not_active IP Right Cessation
- 2000-04-28 CN CNB008069085A patent/CN1331862C/zh not_active Expired - Fee Related
- 2000-04-28 IL IL14592200A patent/IL145922A0/xx active IP Right Grant
- 2000-04-28 ES ES00928698T patent/ES2287016T3/es not_active Expired - Lifetime
- 2000-04-28 CZ CZ20013833A patent/CZ20013833A3/cs unknown
- 2000-04-28 DK DK00928698T patent/DK1177187T3/da active
- 2000-04-28 EE EEP200100556A patent/EE200100556A/xx unknown
- 2000-04-28 PL PL351409A patent/PL196957B1/pl unknown
- 2000-04-28 AU AU46895/00A patent/AU781266B2/en not_active Ceased
- 2000-09-14 US US09/662,649 patent/US6635655B1/en not_active Ceased
-
2001
- 2001-10-14 IL IL145922A patent/IL145922A/en not_active IP Right Cessation
- 2001-10-18 NO NO20015075A patent/NO323643B1/no unknown
- 2001-10-24 ZA ZA200108798A patent/ZA200108798B/en unknown
- 2001-10-26 HR HR20010795A patent/HRP20010795A2/hr not_active Application Discontinuation
-
2002
- 2002-09-26 HK HK02107034.1A patent/HK1045515B/zh not_active IP Right Cessation
-
2005
- 2005-10-20 US US11/254,215 patent/USRE40558E1/en not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4598278B2 (ja) | Ppar受容体リガンドとしてのジアリール酸誘導体 | |
RU2278860C2 (ru) | Производные триарил-содержащих кислот в качестве лигандов рецепторов ппар | |
US20030220373A1 (en) | Therapeutic uses of PPAR mediators | |
JP2001509166A (ja) | 糖尿病および肥満の治療のためのβ▲下3▼作動薬としてのチアゾールベンゼンスルホンアミド | |
JP2003525217A (ja) | 肥満治療用薬剤 | |
JP2001520193A (ja) | キノリン誘導体の治療的使用 | |
JP2006523698A (ja) | Ppar変調薬としての(3−{3−(2,4−ビス−トリフルオロメチル−ベンジル)−(5−エチル−ピリミジン−2−イル)−アミノ−プロポキシ}−フェニル)−酢酸および関連化合物、ならびに代謝性障害の処置方法 | |
MXPA01010788A (es) | Derivados de acido tri-arilico como ligando de receptores ppar |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
PNAN | Change of the applicant name, address/residence |
Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, DE |
|
ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20080423 Year of fee payment: 9 |
|
OBST | Application withdrawn |