HRP20050108A2 - Indolinfenilsulfonamidni derivati - Google Patents

Indolinfenilsulfonamidni derivati Download PDF

Info

Publication number: HRP20050108A2
Authority: HR; Croatia
Prior art keywords: compounds; methyl; image; represents hydrogen; alkyl
Prior art date: 2002-07-03

Application number

HR20050108A

Other languages

English (en)

Croatian (hr)

Inventor

Bischoff Hilmar

Dittrich-Wengenroth Elke

Wuttke Martina

Heckroth Heike

Thielemann Wolfgang

Woltering Michael

Otteneder Michael

Original Assignee

Bayer Healthcare Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-07-03

Filing date

2005-02-02

Publication date

2006-04-30

2005-02-02 Application filed by Bayer Healthcare Ag filed Critical Bayer Healthcare Ag

2006-04-30 Publication of HRP20050108A2 publication Critical patent/HRP20050108A2/hr

Links

150000001875 compounds Chemical class 0.000 claims abstract description 117
238000000034 method Methods 0.000 claims abstract description 48
238000011282 treatment Methods 0.000 claims abstract description 17
238000002360 preparation method Methods 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 9
208000029078 coronary artery disease Diseases 0.000 claims abstract description 6
208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 4
208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 4
238000011321 prophylaxis Methods 0.000 claims abstract description 4
-1 phenoxy, benzyloxy Chemical group 0.000 claims description 83
239000001257 hydrogen Substances 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 59
239000002904 solvent Substances 0.000 claims description 53
238000006243 chemical reaction Methods 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 29
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
150000001735 carboxylic acids Chemical class 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
229910052763 palladium Inorganic materials 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 3
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
238000005859 coupling reaction Methods 0.000 claims description 3
239000002270 dispersing agent Substances 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
206010003210 Arteriosclerosis Diseases 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
238000007887 coronary angioplasty Methods 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
230000002265 prevention Effects 0.000 claims 4
201000010099 disease Diseases 0.000 claims 3
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 abstract description 5
108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 abstract description 5
208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract 1
230000003213 activating effect Effects 0.000 abstract 1
230000003389 potentiating effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 84
239000000203 mixture Substances 0.000 description 68
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 42
239000012071 phase Substances 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
238000005160 1H NMR spectroscopy Methods 0.000 description 28
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
239000003112 inhibitor Substances 0.000 description 23
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 23
150000003254 radicals Chemical class 0.000 description 23
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
239000012265 solid product Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 21
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
229910052796 boron Inorganic materials 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
239000012074 organic phase Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000002585 base Substances 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
229910000029 sodium carbonate Inorganic materials 0.000 description 14
235000017550 sodium carbonate Nutrition 0.000 description 14
239000000126 substance Substances 0.000 description 14
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
210000004369 blood Anatomy 0.000 description 11
239000008280 blood Substances 0.000 description 11
229960004132 diethyl ether Drugs 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
235000019253 formic acid Nutrition 0.000 description 10
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 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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 9
229910052784 alkaline earth metal Inorganic materials 0.000 description 9
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 9
239000008103 glucose Substances 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000012360 testing method Methods 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
BXENIYIGPPXPNY-UHFFFAOYSA-N ethyl 2-(4-chlorosulfonyl-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(S(Cl)(=O)=O)C=C1C BXENIYIGPPXPNY-UHFFFAOYSA-N 0.000 description 8
210000002966 serum Anatomy 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 7
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000000556 agonist Substances 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000011592 zinc chloride Substances 0.000 description 7
235000005074 zinc chloride Nutrition 0.000 description 7
229960000549 4-dimethylaminophenol Drugs 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229940125753 fibrate Drugs 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000008901 benefit Effects 0.000 description 5
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000000499 gel Substances 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
150000007522 mineralic acids Chemical class 0.000 description 5
238000002953 preparative HPLC Methods 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
239000008096 xylene Substances 0.000 description 5
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 4
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
HTFXWAOSQODIBI-UHFFFAOYSA-N 2-benzyl-1,3-dihydropyrrolo[3,4-c]pyridine Chemical compound C1C2=CC=NC=C2CN1CC1=CC=CC=C1 HTFXWAOSQODIBI-UHFFFAOYSA-N 0.000 description 4
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000015779 HDL Lipoproteins Human genes 0.000 description 4
108010010234 HDL Lipoproteins Proteins 0.000 description 4
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 4
102000004877 Insulin Human genes 0.000 description 4
108090001061 Insulin Proteins 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
150000001342 alkaline earth metals Chemical class 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
230000003178 anti-diabetic effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
235000010216 calcium carbonate Nutrition 0.000 description 4
235000012000 cholesterol Nutrition 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229940052303 ethers for general anesthesia Drugs 0.000 description 4
ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
229940125396 insulin Drugs 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000008259 solid foam Substances 0.000 description 4
229940031439 squalene Drugs 0.000 description 4
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 4
150000003460 sulfonic acids Chemical class 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
150000003626 triacylglycerols Chemical class 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
238000000825 ultraviolet detection Methods 0.000 description 4
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
WZRRRFSJFQTGGB-UHFFFAOYSA-N 1,3,5-triazinane-2,4,6-trithione Chemical compound S=C1NC(=S)NC(=S)N1 WZRRRFSJFQTGGB-UHFFFAOYSA-N 0.000 description 3
JGLJQNWIFYBINC-UHFFFAOYSA-N 5-bromo-3,7-dimethyl-1h-indole Chemical compound C1=C(Br)C=C2C(C)=CNC2=C1C JGLJQNWIFYBINC-UHFFFAOYSA-N 0.000 description 3
239000005541 ACE inhibitor Substances 0.000 description 3
229940127291 Calcium channel antagonist Drugs 0.000 description 3
102100039556 Galectin-4 Human genes 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
101000608765 Homo sapiens Galectin-4 Proteins 0.000 description 3
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 3
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 3
108060001084 Luciferase Proteins 0.000 description 3
239000005089 Luciferase Substances 0.000 description 3
208000001145 Metabolic Syndrome Diseases 0.000 description 3
102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 3
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 3
239000003146 anticoagulant agent Substances 0.000 description 3
229940127219 anticoagulant drug Drugs 0.000 description 3
229940030600 antihypertensive agent Drugs 0.000 description 3
239000002220 antihypertensive agent Substances 0.000 description 3
229940127218 antiplatelet drug Drugs 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
239000002876 beta blocker Substances 0.000 description 3
229940097320 beta blocking agent Drugs 0.000 description 3
239000003613 bile acid Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000002934 diuretic Substances 0.000 description 3
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000106 platelet aggregation inhibitor Substances 0.000 description 3
230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
238000004007 reversed phase HPLC Methods 0.000 description 3
235000011150 stannous chloride Nutrition 0.000 description 3
108090000721 thyroid hormone receptors Proteins 0.000 description 3
102000004217 thyroid hormone receptors Human genes 0.000 description 3
CMMXCVYESRODNH-UHFFFAOYSA-N trichloroepoxyethane Chemical class ClC1OC1(Cl)Cl CMMXCVYESRODNH-UHFFFAOYSA-N 0.000 description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
RGGOWBBBHWTTRE-UHFFFAOYSA-N (4-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Br)C=C1 RGGOWBBBHWTTRE-UHFFFAOYSA-N 0.000 description 2
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
HNMLDXRDNZWFFF-UHFFFAOYSA-N 2-[2-methyl-4-[[2,3,7-trimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydroindol-1-yl]sulfonyl]phenoxy]acetic acid Chemical compound CC1C(C)C2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC(C)=C2N1S(=O)(=O)C1=CC=C(OCC(O)=O)C(C)=C1 HNMLDXRDNZWFFF-UHFFFAOYSA-N 0.000 description 2
SFXDRPXQXLPDSQ-UHFFFAOYSA-N 2-[2-methyl-4-[[3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]sulfonyl]phenoxy]acetic acid Chemical compound N1=C2C(C(C)C)CN(S(=O)(=O)C=3C=C(C)C(OCC(O)=O)=CC=3)C2=CC=C1C1=CC=C(C(F)(F)F)C=C1 SFXDRPXQXLPDSQ-UHFFFAOYSA-N 0.000 description 2
LSURRPCGGHDEOE-UHFFFAOYSA-N 2-[2-methyl-4-[[7-methyl-3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydroindol-1-yl]sulfonyl]phenoxy]acetic acid Chemical compound CC(C)C1CN(S(=O)(=O)C=2C=C(C)C(OCC(O)=O)=CC=2)C(C(=C2)C)=C1C=C2C1=CC=C(C(F)(F)F)C=C1 LSURRPCGGHDEOE-UHFFFAOYSA-N 0.000 description 2
PBKOUNYCIJCPAU-UHFFFAOYSA-N 2-[4-[(5-bromo-3,3-dimethyl-2h-indol-1-yl)sulfonyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(S(=O)(=O)N2C3=CC=C(Br)C=C3C(C)(C)C2)=C1 PBKOUNYCIJCPAU-UHFFFAOYSA-N 0.000 description 2
ICYBXSGGXATTOJ-UHFFFAOYSA-N 2-[4-[[3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2h-indol-1-yl]sulfonyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(S(=O)(=O)N2C3=CC=C(C=C3C(C)(C)C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ICYBXSGGXATTOJ-UHFFFAOYSA-N 0.000 description 2
IGKLSDRMQGNXHV-UHFFFAOYSA-N 2-[4-[[3,7-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydroindol-1-yl]sulfonyl]-2-methylphenoxy]acetic acid Chemical compound CC1CN(S(=O)(=O)C=2C=C(C)C(OCC(O)=O)=CC=2)C(C(=C2)C)=C1C=C2C1=CC=C(C(F)(F)F)C=C1 IGKLSDRMQGNXHV-UHFFFAOYSA-N 0.000 description 2
ITQLBRJOQSOVNY-UHFFFAOYSA-N 2-[4-[[5-(4-methoxyphenyl)-2,3-dihydroindol-1-yl]sulfonyl]-2-methylphenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(CC2)S(=O)(=O)C=3C=C(C)C(OCC(O)=O)=CC=3)C2=C1 ITQLBRJOQSOVNY-UHFFFAOYSA-N 0.000 description 2
JQPHUAFVUDUEJL-UHFFFAOYSA-N 3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-1h-pyrrolo[3,2-b]pyridine Chemical compound N1=C2C(C(C)C)=CNC2=CC=C1C1=CC=C(C(F)(F)F)C=C1 JQPHUAFVUDUEJL-UHFFFAOYSA-N 0.000 description 2
SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 2
NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 2
ZQXWWDQQCHITFP-UHFFFAOYSA-N 5-bromo-2,3,7-trimethyl-2,3-dihydro-1h-indole Chemical compound CC1C(C)NC2=C1C=C(Br)C=C2C ZQXWWDQQCHITFP-UHFFFAOYSA-N 0.000 description 2
CPLGFHHNPVKTBM-UHFFFAOYSA-N 5-bromo-3,3-dimethyl-1,2-dihydroindole Chemical compound C1=C(Br)C=C2C(C)(C)CNC2=C1 CPLGFHHNPVKTBM-UHFFFAOYSA-N 0.000 description 2
YXWZPQBOZVTFQU-UHFFFAOYSA-N 5-bromo-3,7-dimethyl-2,3-dihydro-1h-indole Chemical compound C1=C(Br)C=C(C)C2=C1C(C)CN2 YXWZPQBOZVTFQU-UHFFFAOYSA-N 0.000 description 2
ITCDUNBENAFNBA-UHFFFAOYSA-N 5-bromo-7-methyl-3-propan-2-yl-1h-indole Chemical compound C1=C(Br)C=C2C(C(C)C)=CNC2=C1C ITCDUNBENAFNBA-UHFFFAOYSA-N 0.000 description 2
OMGNDYJGIRDCKP-UHFFFAOYSA-N 5-bromo-7-methyl-3-propan-2-yl-2,3-dihydro-1h-indole Chemical compound C1=C(Br)C=C(C)C2=C1C(C(C)C)CN2 OMGNDYJGIRDCKP-UHFFFAOYSA-N 0.000 description 2
QATKNWDGIOKJBT-UHFFFAOYSA-N 5-chloro-3-propan-2-yl-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=C(Cl)N=C2C(C(C)C)=CNC2=C1 QATKNWDGIOKJBT-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
102000015427 Angiotensins Human genes 0.000 description 2
108010064733 Angiotensins Proteins 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229940127328 Cholesterol Synthesis Inhibitors Drugs 0.000 description 2
229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 2
230000004568 DNA-binding Effects 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
206010022489 Insulin Resistance Diseases 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
238000008214 LDL Cholesterol Methods 0.000 description 2
108010007622 LDL Lipoproteins Proteins 0.000 description 2
102000007330 LDL Lipoproteins Human genes 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
229940127470 Lipase Inhibitors Drugs 0.000 description 2
229940086609 Lipase inhibitor Drugs 0.000 description 2
102000004895 Lipoproteins Human genes 0.000 description 2
108090001030 Lipoproteins Proteins 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
108010015181 PPAR delta Proteins 0.000 description 2
108010016731 PPAR gamma Proteins 0.000 description 2
102000000536 PPAR gamma Human genes 0.000 description 2
229940124754 PPAR-alpha/gamma agonist Drugs 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
238000000692 Student's t-test Methods 0.000 description 2
229940100389 Sulfonylurea Drugs 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000002333 angiotensin II receptor antagonist Substances 0.000 description 2
230000001539 anorectic effect Effects 0.000 description 2
239000003472 antidiabetic agent Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
230000027455 binding Effects 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
230000001906 cholesterol absorption Effects 0.000 description 2
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
239000000824 cytostatic agent Substances 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
206010061428 decreased appetite Diseases 0.000 description 2
238000007257 deesterification reaction Methods 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
NHFQSFIBSJPLIW-UHFFFAOYSA-N ethyl 2-(2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C NHFQSFIBSJPLIW-UHFFFAOYSA-N 0.000 description 2
HCEWGGOXVMQYMS-UHFFFAOYSA-N ethyl 2-[4-[(5-bromo-2,3-dihydroindol-1-yl)sulfonyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2CC1 HCEWGGOXVMQYMS-UHFFFAOYSA-N 0.000 description 2
PNHDKKARGRCTMT-UHFFFAOYSA-N ethyl 2-[4-[(5-bromo-3,3-dimethyl-2h-indol-1-yl)sulfonyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(C)(C)C1 PNHDKKARGRCTMT-UHFFFAOYSA-N 0.000 description 2
UTUMTYRJANTOBC-UHFFFAOYSA-N ethyl 2-[4-[(5-bromo-3,7-dimethyl-2,3-dihydroindol-1-yl)sulfonyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1S(=O)(=O)N1C2=C(C)C=C(Br)C=C2C(C)C1 UTUMTYRJANTOBC-UHFFFAOYSA-N 0.000 description 2
229950003707 farglitazar Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
208000006575 hypertriglyceridemia Diseases 0.000 description 2
229940126904 hypoglycaemic agent Drugs 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
108020001756 ligand binding domains Proteins 0.000 description 2
230000037356 lipid metabolism Effects 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
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 2
230000010412 perfusion Effects 0.000 description 2
102000013415 peroxidase activity proteins Human genes 0.000 description 2
108040007629 peroxidase activity proteins Proteins 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
229910000160 potassium phosphate Inorganic materials 0.000 description 2
235000011009 potassium phosphates Nutrition 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
125000002098 pyridazinyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
239000002464 receptor antagonist Substances 0.000 description 2
229940044551 receptor antagonist Drugs 0.000 description 2
229910052990 silicon hydride Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000009747 swallowing Effects 0.000 description 2
239000003826 tablet Substances 0.000 description 2
RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
150000001467 thiazolidinediones Chemical class 0.000 description 2
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
230000009261 transgenic effect Effects 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
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 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
AMNXBQPRODZJQR-DITALETJSA-N (2s)-2-cyclopentyl-2-[3-[(2,4-dimethylpyrido[2,3-b]indol-9-yl)methyl]phenyl]-n-[(1r)-2-hydroxy-1-phenylethyl]acetamide Chemical compound C1([C@@H](C=2C=CC=C(C=2)CN2C3=CC=CC=C3C3=C(C)C=C(N=C32)C)C(=O)N[C@@H](CO)C=2C=CC=CC=2)CCCC1 AMNXBQPRODZJQR-DITALETJSA-N 0.000 description 1
LJCBAPRMNYSDOP-LVCYMWGESA-N (2s)-3-(7-carbamimidoylnaphthalen-2-yl)-2-[4-[(3s)-1-ethanimidoylpyrrolidin-3-yl]oxyphenyl]propanoic acid;hydron;chloride;pentahydrate Chemical compound O.O.O.O.O.Cl.C1N(C(=N)C)CC[C@@H]1OC1=CC=C([C@H](CC=2C=C3C=C(C=CC3=CC=2)C(N)=N)C(O)=O)C=C1 LJCBAPRMNYSDOP-LVCYMWGESA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
VJTBVNWEWUHQOT-UHFFFAOYSA-N (4-bromo-2-methylphenyl)hydrazine Chemical compound CC1=CC(Br)=CC=C1NN VJTBVNWEWUHQOT-UHFFFAOYSA-N 0.000 description 1
NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 1
VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
XHEJLXPUJJYRBJ-UHFFFAOYSA-N (6-chloropyridin-3-yl)hydrazine Chemical compound NNC1=CC=C(Cl)N=C1 XHEJLXPUJJYRBJ-UHFFFAOYSA-N 0.000 description 1
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
HBORMJBGPGQHSF-UHFFFAOYSA-N 1-(benzenesulfonyl)-3h-indol-2-one Chemical class O=C1CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 HBORMJBGPGQHSF-UHFFFAOYSA-N 0.000 description 1
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 1
PMGZJNCIQHGNLT-UHFFFAOYSA-N 1-[bis(2,2-dimethylpropanoyloxymethoxy)phosphoryl]-4-(3-phenoxyphenyl)butane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C(S(O)(=O)=O)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PMGZJNCIQHGNLT-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
HXWLJBVVXXBZCM-UHFFFAOYSA-N 2,3-dihydroxypropyl nitrate Chemical compound OCC(O)CO[N+]([O-])=O HXWLJBVVXXBZCM-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
CASCTHHMARGRLB-UHFFFAOYSA-N 2-(3-amino-1,2-benzoxazol-5-yl)-n-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide;hydrochloride Chemical compound Cl.CN(C)CC1=NC=CN1C(C=C1F)=CC=C1NC(=O)C1=CC(C(F)(F)F)=NN1C1=CC=C(ON=C2N)C2=C1 CASCTHHMARGRLB-UHFFFAOYSA-N 0.000 description 1
DEMLYXMVPJAVFU-UHFFFAOYSA-N 2-(chloromethyl)oxirane;2-methyl-1h-imidazole Chemical compound ClCC1CO1.CC1=NC=CN1 DEMLYXMVPJAVFU-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 1
HQSRVYUCBOCBLY-XOOFNSLWSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2s,4r)-2-(4-chlorophenyl)-2-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3O[C@@](CSC=4N(C=NN=4)C)(OC3)C=3C=CC(Cl)=CC=3)=CC=2)C=C1 HQSRVYUCBOCBLY-XOOFNSLWSA-N 0.000 description 1
UOJMJBUYXYEPFX-UHFFFAOYSA-N 2-[4-(4-hydroxy-3-propan-2-ylphenoxy)-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound C1=C(O)C(C(C)C)=CC(OC=2C(=CC(NC(=O)C(O)=O)=CC=2C)C)=C1 UOJMJBUYXYEPFX-UHFFFAOYSA-N 0.000 description 1
CYWFEOLZGQJQKP-UHFFFAOYSA-N 2-[4-[(5-bromo-2,3-dihydroindol-1-yl)sulfonyl]-2-methylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC(S(=O)(=O)N2C3=CC=C(Br)C=C3CC2)=C1 CYWFEOLZGQJQKP-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
AUYYCJSJGJYCDS-UHFFFAOYSA-N 2/3/6893 Natural products IC1=CC(CC(N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-UHFFFAOYSA-N 0.000 description 1
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
RLIFJQIAFXKBQY-UHFFFAOYSA-N 3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical compound N1=C2C(C(C)C)CNC2=CC=C1C1=CC=C(C(F)(F)F)C=C1 RLIFJQIAFXKBQY-UHFFFAOYSA-N 0.000 description 1
NOBZETMXGVAWIM-UHFFFAOYSA-N 4-[(2-carbamimidoyl-3,4-dihydro-1h-isoquinolin-7-yl)oxymethyl]-1-pyridin-4-ylpiperidine-4-carboxylic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=C2CN(C(=N)N)CCC2=CC=C1OCC(CC1)(C(O)=O)CCN1C1=CC=NC=C1 NOBZETMXGVAWIM-UHFFFAOYSA-N 0.000 description 1
PCHYYOCUCGCSBU-UHFFFAOYSA-N 4-bromo-2-methylaniline Chemical compound CC1=CC(Br)=CC=C1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
QEDCHCLHHGGYBT-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1h-indole Chemical compound BrC1=CC=C2NCCC2=C1 QEDCHCLHHGGYBT-UHFFFAOYSA-N 0.000 description 1
QAJYCQZQLVENRZ-UHFFFAOYSA-N 6-chloropyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1 QAJYCQZQLVENRZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
229940123073 Angiotensin antagonist Drugs 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
239000005552 B01AC04 - Clopidogrel Substances 0.000 description 1
239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
239000004072 C09CA03 - Valsartan Substances 0.000 description 1
239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
229920001268 Cholestyramine Polymers 0.000 description 1
KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 description 1
229920002905 Colesevelam Polymers 0.000 description 1
229920002911 Colestipol Polymers 0.000 description 1
XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229940123583 Factor Xa inhibitor Drugs 0.000 description 1
102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 description 1
108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 description 1
101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
102400000321 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 1
FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
208000002705 Glucose Intolerance Diseases 0.000 description 1
206010018429 Glucose tolerance impaired Diseases 0.000 description 1
102000004366 Glucosidases Human genes 0.000 description 1
108010056771 Glucosidases Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
101000741797 Homo sapiens Peroxisome proliferator-activated receptor delta Proteins 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
206010060378 Hyperinsulinaemia Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229940122355 Insulin sensitizer Drugs 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
108010001831 LDL receptors Proteins 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
241000254158 Lampyridae Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
102000057248 Lipoprotein(a) Human genes 0.000 description 1
108010033266 Lipoprotein(a) Proteins 0.000 description 1
102100024640 Low-density lipoprotein receptor Human genes 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
108700010041 Nicotinic acid receptor Proteins 0.000 description 1
108020005497 Nuclear hormone receptor Proteins 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229940126033 PPAR agonist Drugs 0.000 description 1
108010028924 PPAR alpha Proteins 0.000 description 1
102000023984 PPAR alpha Human genes 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
241000254058 Photinus Species 0.000 description 1
229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229940127315 Potassium Channel Openers Drugs 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
102100040918 Pro-glucagon Human genes 0.000 description 1
229940123934 Reductase inhibitor Drugs 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229920001304 Solutol HS 15 Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 1
229940123464 Thiazolidinedione Drugs 0.000 description 1
229940122388 Thrombin inhibitor Drugs 0.000 description 1
102000006601 Thymidine Kinase Human genes 0.000 description 1
108020004440 Thymidine kinase Proteins 0.000 description 1
AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical compound IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
102000040945 Transcription factor Human genes 0.000 description 1
108091023040 Transcription factor Proteins 0.000 description 1
108010004977 Vasopressins Proteins 0.000 description 1
102000002852 Vasopressins Human genes 0.000 description 1
HKPPDMRSVIYYKG-FPDMAROZSA-M [1-[(3R)-1-(2,4-difluorophenyl)-1-hydroxy-3-[2-oxo-3-[4-(tetrazol-1-yl)phenyl]imidazolidin-1-yl]butyl]-1,2,4-triazol-4-ium-4-yl]methyl acetate chloride Chemical compound [Cl-].C[C@H](CC(O)(c1ccc(F)cc1F)n1c[n+](COC(C)=O)cn1)N1CCN(C1=O)c1ccc(cc1)-n1cnnn1 HKPPDMRSVIYYKG-FPDMAROZSA-M 0.000 description 1
229960000446 abciximab Drugs 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001323 aldoses Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229940126317 angiotensin II receptor antagonist Drugs 0.000 description 1
238000010171 animal model Methods 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
229940127217 antithrombotic drug Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
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 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
OIRCOABEOLEUMC-GEJPAHFPSA-N bivalirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 OIRCOABEOLEUMC-GEJPAHFPSA-N 0.000 description 1
229960001500 bivalirudin Drugs 0.000 description 1
108010055460 bivalirudin Proteins 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
229960000830 captopril Drugs 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
229960005110 cerivastatin Drugs 0.000 description 1
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
229960002174 ciprofibrate Drugs 0.000 description 1
KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
229960001214 clofibrate Drugs 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
238000010367 cloning Methods 0.000 description 1
GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
229960003009 clopidogrel Drugs 0.000 description 1
GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 1
229960002604 colestipol Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004590 computer program Methods 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
229940111134 coxibs Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229960001767 dextrothyroxine Drugs 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
229960004042 diazoxide Drugs 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 1
229960002877 dihydralazine Drugs 0.000 description 1
XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
229960002768 dipyridamole Drugs 0.000 description 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
XRKMNJXYOFSTBE-UHFFFAOYSA-N disodium;iron(4+);nitroxyl anion;pentacyanide;dihydrate Chemical compound O.O.[Na+].[Na+].[Fe+4].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].O=[N-] XRKMNJXYOFSTBE-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000132 electrospray ionisation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
238000007824 enzymatic assay Methods 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
238000001952 enzyme assay Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
KSIKVEINAYFQCW-UHFFFAOYSA-N ethyl 2-[2-methyl-4-[[3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydropyrrolo[3,2-b]pyridin-1-yl]sulfonyl]phenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1S(=O)(=O)N1C2=CC=C(C=3C=CC(=CC=3)C(F)(F)F)N=C2C(C(C)C)C1 KSIKVEINAYFQCW-UHFFFAOYSA-N 0.000 description 1
HNHRFRMYABLXDY-UHFFFAOYSA-N ethyl 2-[4-[(5-bromo-2,3,7-trimethyl-2,3-dihydroindol-1-yl)sulfonyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC=C1S(=O)(=O)N1C2=C(C)C=C(Br)C=C2C(C)C1C HNHRFRMYABLXDY-UHFFFAOYSA-N 0.000 description 1
FUBBWDWIGBTUPQ-UHFFFAOYSA-N ethyl 2-[4-[3-[(4-fluorophenyl)-hydroxymethyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(O)C=2C=CC(F)=CC=2)=C1 FUBBWDWIGBTUPQ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
229960000815 ezetimibe Drugs 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960003883 furosemide Drugs 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229960003627 gemfibrozil Drugs 0.000 description 1
229960004580 glibenclamide Drugs 0.000 description 1
229960000346 gliclazide Drugs 0.000 description 1
229960004346 glimepiride Drugs 0.000 description 1
WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
229960001381 glipizide Drugs 0.000 description 1
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 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
230000004110 gluconeogenesis Effects 0.000 description 1
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 1
230000004116 glycogenolysis Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000003451 hyperinsulinaemic effect Effects 0.000 description 1
201000008980 hyperinsulinism Diseases 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000007943 implant Substances 0.000 description 1
229950005809 implitapide Drugs 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000000411 inducer Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000008263 liquid aerosol Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
201000007270 liver cancer Diseases 0.000 description 1
208000014018 liver neoplasm Diseases 0.000 description 1
229960003566 lomitapide Drugs 0.000 description 1
QKVKOFVWUHNEBX-UHFFFAOYSA-N lomitapide mesylate Chemical compound CS(O)(=O)=O.C12=CC=CC=C2C2=CC=CC=C2C1(C(=O)NCC(F)(F)F)CCCCN(CC1)CCC1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QKVKOFVWUHNEBX-UHFFFAOYSA-N 0.000 description 1
229960004773 losartan Drugs 0.000 description 1
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
239000003055 low molecular weight heparin Chemical class 0.000 description 1
229940127215 low-molecular weight heparin Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
210000004962 mammalian cell Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
DKWNMCUOEDMMIN-PKOBYXMFSA-N melagatran Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)[C@H]1N(C(=O)[C@H](NCC(O)=O)C2CCCCC2)CC1 DKWNMCUOEDMMIN-PKOBYXMFSA-N 0.000 description 1
229960002137 melagatran Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
229960003105 metformin Drugs 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229960003632 minoxidil Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
JLTCWSBVQSZVLT-UHFFFAOYSA-N n-[6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxa Chemical compound NCCCCC(C(=O)NCC(N)=O)NC(=O)C1CCCN1C(=O)C1NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(N)CSSC1.N1C(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 JLTCWSBVQSZVLT-UHFFFAOYSA-N 0.000 description 1
125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
229960000698 nateglinide Drugs 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical class COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
102000006255 nuclear receptors Human genes 0.000 description 1
108020004017 nuclear receptors Proteins 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
229960001243 orlistat Drugs 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000003336 oxytocin antagonist Substances 0.000 description 1
229940121361 oxytocin antagonists Drugs 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229960002797 pitavastatin Drugs 0.000 description 1
VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000005180 public health Effects 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
229960002354 repaglinide Drugs 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
229960000672 rosuvastatin Drugs 0.000 description 1
BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229940083618 sodium nitroprusside Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000008275 solid aerosol Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960005187 telmisartan Drugs 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
239000005495 thyroid hormone Substances 0.000 description 1
229940036555 thyroid hormone Drugs 0.000 description 1
PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
229960005001 ticlopidine Drugs 0.000 description 1
COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 description 1
229960003425 tirofiban Drugs 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
229950004514 torcetrapib Drugs 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
229960004699 valsartan Drugs 0.000 description 1
SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
238000012795 verification Methods 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229940019333 vitamin k antagonists Drugs 0.000 description 1
ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
229960001522 ximelagatran Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

HR20050108A 2002-07-03 2005-02-02 Indolinfenilsulfonamidni derivati HRP20050108A2 (hr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10229777A DE10229777A1 (de)	2002-07-03	2002-07-03	Indolin-Phenylsulfonamid-Derivate
PCT/EP2003/006896 WO2004005253A1 (de)	2002-07-03	2003-06-30	Indolin-phenylsulfonamid-derivate

Publications (1)

Publication Number	Publication Date
HRP20050108A2 true HRP20050108A2 (hr)	2006-04-30

Family

ID=29796112

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20050108A HRP20050108A2 (hr)	2002-07-03	2005-02-02	Indolinfenilsulfonamidni derivati

Country Status (26)

Country	Link
US (1)	US20060100230A1 (pt)
EP (1)	EP1519919A1 (pt)
JP (1)	JP2005535649A (pt)
CN (1)	CN1678581A (pt)
AR (1)	AR040352A1 (pt)
AU (1)	AU2003246638A1 (pt)
BR (1)	BR0312549A (pt)
CA (1)	CA2491477A1 (pt)
DE (1)	DE10229777A1 (pt)
EC (1)	ECSP055524A (pt)
GT (1)	GT200300135A (pt)
HN (1)	HN2003000196A (pt)
HR (1)	HRP20050108A2 (pt)
IL (1)	IL165924A0 (pt)
MA (1)	MA27316A1 (pt)
MX (1)	MXPA05000133A (pt)
MY (1)	MY134641A (pt)
NO (1)	NO20050579L (pt)
NZ (1)	NZ537486A (pt)
PE (1)	PE20040645A1 (pt)
RU (1)	RU2328485C2 (pt)
TW (1)	TW200418794A (pt)
UA (1)	UA79003C2 (pt)
UY (1)	UY27878A1 (pt)
WO (1)	WO2004005253A1 (pt)
ZA (1)	ZA200500013B (pt)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10335450A1 (de) *	2003-08-02	2005-02-17	Bayer Ag	Indolin-Sulfanilsäureamide
DE10337839A1 (de) *	2003-08-18	2005-03-17	Bayer Healthcare Ag	Indolin-Derivate
AR045582A1 (es) *	2003-09-05	2005-11-02	Neurogen Corp	Piridinas pirazinas y pirimidinas heteroarilo fusionadas como ligandos receptores de crf1
AR048523A1 (es) *	2004-04-07	2006-05-03	Kalypsys Inc	Compuestos con estructura de aril sulfonamida y sulfonilo como moduladores de ppar y metodos para tratar trastornos metabolicos
ES2352085T3 (es)	2004-05-05	2011-02-15	High Point Pharmaceuticals, Llc	Nuevos compuestos, su preparación y uso.
JP4981662B2 (ja)	2004-05-05	2012-07-25	ハイ・ポイント・ファーマスーティカルズ、エルエルシー	新規の化合物、その製法と使用
FR2869904B1 (fr)	2004-05-07	2006-07-28	Fournier S A Sa Lab	Modulateurs des recepteurs lxr
FR2873694B1 (fr) *	2004-07-27	2006-12-08	Merck Sante Soc Par Actions Si	Nouveaux aza-indoles inhibiteurs de la mtp et apob
CN101421258B (zh) *	2004-10-29	2013-08-21	凯利普西斯公司	作为ppar调节剂的磺酰基取代的双环化合物
HUE039584T2 (hu)	2004-10-29	2019-01-28	Kalypsys Inc	PPAR-modulátor szulfonil-szubsztituált biciklusos vegyületek
CA2593483A1 (en) *	2005-01-18	2006-07-27	Novartis Ag	Methods of use of dual ppar agonist compounds and drug delivery devices containing such compounds
DE102005020230A1 (de) *	2005-04-30	2006-11-09	Bayer Healthcare Ag	Verwendung von Indolin-Phenylsulfonamid-Derivaten
DE102005020229A1 (de) *	2005-04-30	2006-11-09	Bayer Healthcare Ag	Verwendung von Indolin-Phenylsulfonamid-Derivaten
FR2886293B1 (fr) *	2005-05-30	2007-08-24	Fournier S A Sa Lab	Nouveaux composes de l'indoline
US7943669B2 (en)	2005-06-30	2011-05-17	High Point Pharmaceuticals, Llc	Phenoxy acetic acids as PPAR delta activators
FR2890072A1 (fr) *	2005-09-01	2007-03-02	Fournier S A Sa Lab	Nouveaux composesde pyrrolopyridine
CN103224477A (zh)	2005-12-22	2013-07-31	高点制药有限责任公司	作为PPAR-δ活化剂的苯氧基乙酸
CA2645719A1 (en)	2006-03-09	2007-09-13	High Point Pharmaceuticals, Llc	Compounds that modulate ppar activity, their preparation and use
TWI315304B (en)	2006-08-31	2009-10-01	Univ Taipei Medical	Indoline-sulfonamides compounds
EP1932843A1 (en)	2006-12-14	2008-06-18	sanofi-aventis	Sulfonyl-phenyl-2H-(1,2,4) oxadiazole-5-one derivatives, processes for their preparation and their use as pharmaceuticals
WO2008091863A1 (en)	2007-01-23	2008-07-31	Kalypsys, Inc.	Sulfonyl-substituted bicyclic compounds as ppar modulators for the treatment of non-alcoholic steatohepatitis
TW200848021A (en)	2007-03-06	2008-12-16	Wyeth Corp	Sulfonylated heterocycles useful for modulation of the progesterone receptor
PE20090159A1 (es)	2007-03-08	2009-02-21	Plexxikon Inc	COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs
WO2010000353A1 (en) *	2008-06-09	2010-01-07	Sanofi-Aventis	Sulfonamides with heterocycle and oxadiazolone headgroup, processes for their preparation and their use as pharmaceuticals
BRPI0914978A2 (pt) *	2008-06-09	2015-10-27	Sanofi Aventis	sulfonamidas n-heterocíclicas reforçadas com grupo principal de oxadiazolona, processos para sua preparação e seu uso como farmacêuticos
US8410284B2 (en)	2008-10-22	2013-04-02	Merck Sharp & Dohme Corp	Cyclic benzimidazole derivatives useful as anti-diabetic agents
CN102271509A (zh)	2008-10-31	2011-12-07	默沙东公司	用于抗糖尿病药的新型环苯并咪唑衍生物
CA2786314A1 (en)	2010-02-25	2011-09-01	Merck Sharp & Dohme Corp.	Novel cyclic benzimidazole derivatives useful anti-diabetic agents
PE20140192A1 (es)	2010-10-06	2014-02-24	Glaxosmithkline Llc	Derivados de bencimidazol como inhibidores de cinasa pi3
WO2012064744A2 (en)	2010-11-08	2012-05-18	Lycera Corporation	Tetrahydroquinoline and related bicyclic compounds for inhibition of rorϒ activity and the treatment of disease
CN103476258B (zh)	2011-02-25	2017-04-26	默沙东公司	用作抗糖尿病药剂的新的环状氮杂苯并咪唑衍生物
MX367341B (es) *	2012-05-08	2019-08-14	Merck Sharp & Dohme	Tetrahidronaftiridina y compuestos biciclicos relacionados para la inhibicion de la actividad de rorgamma y el tratamiento de enfermedades.
US9394315B2 (en)	2012-05-08	2016-07-19	Lycera Corporation	Tetrahydro[1,8]naphthyridine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease
CA2880901A1 (en)	2012-08-02	2014-02-06	Merck Sharp & Dohme Corp.	Antidiabetic tricyclic compounds
RU2015140066A (ru)	2013-02-22	2017-03-30	Мерк Шарп И Доум Корп.	Противодиабетические бициклические соединения
EP2970119B1 (en)	2013-03-14	2021-11-03	Merck Sharp & Dohme Corp.	Novel indole derivatives useful as anti-diabetic agents
US9745297B2 (en) *	2013-07-30	2017-08-29	Boehringer Ingelheim International Gmbh	Compounds as modulators of RORC
US9487493B2 (en)	2013-09-09	2016-11-08	Vtv Therapeutics Llc	Use of a PPAR-delta agonist for treating muscle atrophy
WO2015051496A1 (en)	2013-10-08	2015-04-16	Merck Sharp & Dohme Corp.	Antidiabetic tricyclic compounds
CN103626767A (zh) *	2013-12-04	2014-03-12	上海药明康德新药开发有限公司	区域选择性的氮杂吲哚及其合成方法
WO2015095795A1 (en)	2013-12-20	2015-06-25	Merck Sharp & Dohme Corp.	TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE
WO2015095792A1 (en)	2013-12-20	2015-06-25	Merck Sharp & Dohme Corp.	Carbamate benzoxaxine propionic acids and acid derivatives for modulation of rorgamma activity and the treatment of disease
WO2015095788A1 (en)	2013-12-20	2015-06-25	Merck Sharp & Dohme Corp.	2-ACYLAMIDOMETHYL AND SULFONYLAMIDOMETHYL BENZOXAZINE CARBAMATES FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE
US10532088B2 (en)	2014-02-27	2020-01-14	Lycera Corporation	Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma and related therapeutic methods
WO2015171558A2 (en)	2014-05-05	2015-11-12	Lycera Corporation	BENZENESULFONAMIDO AND RELATED COMPOUNDS FOR USE AS AGONISTS OF RORγ AND THE TREATEMENT OF DISEASE
JP6728061B2 (ja)	2014-05-05	2020-07-22	リセラ・コーポレイションＬｙｃｅｒａＣｏｒｐｏｒａｔｉｏｎ	ＲＯＲγアゴニストとして用いるテトラヒドロキノリンスルホンアミド及び関連化合物ならびに疾患の治療
WO2016130818A1 (en)	2015-02-11	2016-08-18	Merck Sharp & Dohme Corp.	SUBSTITUTED PYRAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF
US10421751B2 (en)	2015-05-05	2019-09-24	Lycera Corporation	Dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease
JP6838004B2 (ja)	2015-06-11	2021-03-03	リセラ・コーポレイションＬｙｃｅｒａＣｏｒｐｏｒａｔｉｏｎ	ＲＯＲγのアゴニストとしての使用及び疾患の治療のためのアリールジヒドロ−２Ｈ−ベンゾ［ｂ］［１，４］オキサジンスルホンアミド及び関連化合物
JP2018531957A (ja)	2015-10-27	2018-11-01	メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋＳｈａｒｐ＆ＤｏｈｍｅＣｏｒｐ．	ＲＯＲγＴ阻害薬としての置換二環式ピラゾール化合物及びその使用
EP3368535B1 (en)	2015-10-27	2020-12-02	Merck Sharp & Dohme Corp.	Heteroaryl substituted benzoic acids as rorgammat inhibitors and uses thereof
MX2018005004A (es)	2015-10-27	2018-09-12	Merck Sharp & Dohme	Compuestos de indazol substituidos como inhibidores de rorgammat y sus usos.
US11072602B2 (en)	2016-12-06	2021-07-27	Merck Sharp & Dohme Corp.	Antidiabetic heterocyclic compounds
US10968232B2 (en)	2016-12-20	2021-04-06	Merck Sharp & Dohme Corp.	Antidiabetic spirochroman compounds
CN110483509B (zh) *	2019-09-04	2020-08-25	温州大学	一种合成含氮杂环衍生物的方法
CN110627785B (zh) *	2019-09-19	2021-06-25	温州大学	一种1,5-四氢萘啶衍生物的制备方法
JP2023506951A (ja) *	2019-12-18	2023-02-20	ザリージェンツオブザユニバーシティオブカリフォルニア	Ｌｉｎ２８の阻害剤及びその使用方法
TW202220958A (zh) *	2020-08-07	2022-06-01	美商卡司馬療法公司	Ｔｒｐｍｌ調節劑
WO2023147309A1 (en)	2022-01-25	2023-08-03	Reneo Pharmaceuticals, Inc.	Use of ppar-delta agonists in the treatment of disease

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2708605A1 (fr) *	1993-07-30	1995-02-10	Sanofi Sa	Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant.
US5795890A (en) *	1995-09-27	1998-08-18	Ono Pharmaceutical Co., Ltd.	Sulfonamide derivatives
FR2757157B1 (fr) *	1996-12-13	1999-12-31	Sanofi Sa	Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant
WO2002014291A1 (en) *	2000-08-11	2002-02-21	Nippon Chemiphar Co.,Ltd.	PPARδ ACTIVATORS

2002
- 2002-07-03 DE DE10229777A patent/DE10229777A1/de not_active Withdrawn
2003
- 2003-06-30 RU RU2005102592/04A patent/RU2328485C2/ru not_active IP Right Cessation
- 2003-06-30 EP EP03762547A patent/EP1519919A1/de not_active Withdrawn
- 2003-06-30 BR BR0312549-1A patent/BR0312549A/pt not_active IP Right Cessation
- 2003-06-30 CA CA002491477A patent/CA2491477A1/en not_active Abandoned
- 2003-06-30 MX MXPA05000133A patent/MXPA05000133A/es unknown
- 2003-06-30 US US10/519,125 patent/US20060100230A1/en not_active Abandoned
- 2003-06-30 CN CNA038209446A patent/CN1678581A/zh active Pending
- 2003-06-30 UA UAA200500952A patent/UA79003C2/uk unknown
- 2003-06-30 WO PCT/EP2003/006896 patent/WO2004005253A1/de not_active Application Discontinuation
- 2003-06-30 JP JP2004518622A patent/JP2005535649A/ja not_active Withdrawn
- 2003-06-30 NZ NZ537486A patent/NZ537486A/en unknown
- 2003-06-30 AR ARP030102373A patent/AR040352A1/es not_active Application Discontinuation
- 2003-06-30 AU AU2003246638A patent/AU2003246638A1/en not_active Abandoned
- 2003-07-01 MY MYPI20032474A patent/MY134641A/en unknown
- 2003-07-02 GT GT200300135A patent/GT200300135A/es unknown
- 2003-07-02 UY UY27878A patent/UY27878A1/es not_active Application Discontinuation
- 2003-07-02 TW TW092118027A patent/TW200418794A/zh unknown
- 2003-07-02 PE PE2003000668A patent/PE20040645A1/es not_active Application Discontinuation
- 2003-07-02 HN HN2003000196A patent/HN2003000196A/es unknown
2004
- 2004-12-22 IL IL16592404A patent/IL165924A0/xx unknown
2005
- 2005-01-03 EC EC2005005524A patent/ECSP055524A/es unknown
- 2005-01-03 ZA ZA200500013A patent/ZA200500013B/en unknown
- 2005-01-03 MA MA28032A patent/MA27316A1/fr unknown
- 2005-02-02 NO NO20050579A patent/NO20050579L/no not_active Application Discontinuation
- 2005-02-02 HR HR20050108A patent/HRP20050108A2/hr not_active Application Discontinuation

Also Published As

Publication number	Publication date
RU2328485C2 (ru)	2008-07-10
TW200418794A (en)	2004-10-01
US20060100230A1 (en)	2006-05-11
CA2491477A1 (en)	2004-01-15
MXPA05000133A (es)	2005-04-11
WO2004005253A1 (de)	2004-01-15
MA27316A1 (fr)	2005-05-02
AU2003246638A1 (en)	2004-01-23
AR040352A1 (es)	2005-03-30
PE20040645A1 (es)	2004-10-29
ECSP055524A (es)	2005-03-10
UA79003C2 (en)	2007-05-10
UY27878A1 (es)	2004-02-27
CN1678581A (zh)	2005-10-05
ZA200500013B (en)	2006-03-29
DE10229777A1 (de)	2004-01-29
JP2005535649A (ja)	2005-11-24
MY134641A (en)	2007-12-31
NO20050579L (no)	2005-02-02
BR0312549A (pt)	2005-04-26
EP1519919A1 (de)	2005-04-06
NZ537486A (en)	2006-07-28
RU2005102592A (ru)	2005-07-10
HN2003000196A (es)	2004-11-22
IL165924A0 (en)	2006-01-15
GT200300135A (es)	2004-03-17

Publication	Publication Date	Title
HRP20050108A2 (hr)	2006-04-30	Indolinfenilsulfonamidni derivati
RU2345983C2 (ru)	2009-02-10	Гетероциклические соединения и способы применения
US20070060595A1 (en)	2007-03-15	Novel fused heterocyclic compound and use thereof
JP2006509801A (ja)	2006-03-23	新規ｍｃｈ受容体アンタゴニスト
JP6627835B2 (ja)	2020-01-08	Ｋｃｎｑ２〜５チャネル活性化剤
JP2011207907A (ja)	2011-10-20	医薬品としてのアゼピノインドール誘導体
JP2019519485A (ja)	2019-07-11	インドールアミン２，３−ジオキシゲナーゼ阻害剤およびその使用方法
JP2019516682A (ja)	2019-06-20	インドールアミン２，３−ジオキシゲナーゼ阻害剤およびその使用方法
US20070149514A1 (en)	2007-06-28	Indole-phenylsulfonamide derivatives used as ppar-delta activating compounds
CA2589896A1 (en)	2006-06-08	Indole derivatives for use as ppar active compounds
JP2009510073A (ja)	2009-03-12	カルボキシアミン化合物およびその使用方法
WO2005035534A1 (ja)	2005-04-21	複素ビシクロ環および複素トリシクロ環化合物およびその医薬
TWI731420B (zh)	2021-06-21	具有吲哚胺-2,3-雙加氧酶抑制活性的喹啉衍生物及其製備方法、藥物組合物、聯合用藥物與用途
JP2008520715A (ja)	2008-06-19	ナイアシン受容体アゴニスト、そのような化合物を含む組成物、および治療方法
RU2296759C2 (ru)	2007-04-10	N-замещенные 1н-индол-5-пропионовые кислоты, фармацевтическая композиция, содержащая эти соединения, и их применение (варианты)
EP2013170B1 (en)	2012-06-27	4-squarylpiperazine derivatives as antiviral agents
JP6197971B1 (ja)	2017-09-20	Ｋｃｎｑ２〜５チャネル関連疾患の予防および／または治療剤
JP2013534928A (ja)	2013-09-09	新規テトラヒドロキノリン誘導体
JP2007501195A (ja)	2007-01-25	二環式インドリンスルホンアミド誘導体
JP2007501196A (ja)	2007-01-25	Ｐｐａｒ−デルタ調節因子としてのインドリンスルファニル酸アミド化合物
KR20050023388A (ko)	2005-03-09	인돌린 페닐술폰아미드 유도체
JP2007502797A (ja)	2007-02-15	インドリン誘導体
WO2024217513A1 (zh)	2024-10-24	β-catenin/BCL9蛋白-蛋白相互作用抑制剂及其制备方法和应用
WO2021129629A1 (zh)	2021-07-01	Zeste增强子同源物2抑制剂及其用途
AU2003262984A1 (en)	2004-03-19	Indoles having anti-diabetic activity

Legal Events

Date	Code	Title	Description
2006-04-30	A1OB	Publication of a patent application
2006-10-19	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2008-06-27	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20080627 Year of fee payment: 6
2009-09-23	OBST	Application withdrawn