CA2600681A1 - Pyrimidine carboxylic acid derivatives and use thereof - Google Patents
Pyrimidine carboxylic acid derivatives and use thereof Download PDFInfo
- Publication number
- CA2600681A1 CA2600681A1 CA002600681A CA2600681A CA2600681A1 CA 2600681 A1 CA2600681 A1 CA 2600681A1 CA 002600681 A CA002600681 A CA 002600681A CA 2600681 A CA2600681 A CA 2600681A CA 2600681 A1 CA2600681 A1 CA 2600681A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- alkoxy
- compound
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 110
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 5
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 242
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- -1 nitro, cyano, amino Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000012453 solvate Substances 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical group 0.000 claims description 29
- 239000003112 inhibitor Substances 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Chemical group 0.000 claims description 20
- 229910052801 chlorine Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000012442 inert solvent Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000005557 antagonist Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 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 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 239000000556 agonist Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 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 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000003613 bile acid Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 102000004877 Insulin Human genes 0.000 claims description 5
- 108090001061 Insulin Proteins 0.000 claims description 5
- 230000003178 anti-diabetic effect Effects 0.000 claims description 5
- 229940125753 fibrate Drugs 0.000 claims description 5
- 210000001685 thyroid gland Anatomy 0.000 claims 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 claims description 4
- 239000005541 ACE inhibitor Substances 0.000 claims description 4
- 102000015427 Angiotensins Human genes 0.000 claims description 4
- 108010064733 Angiotensins Proteins 0.000 claims description 4
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
- 229940127218 antiplatelet drug Drugs 0.000 claims description 4
- 239000002876 beta blocker Substances 0.000 claims description 4
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims 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 claims description 4
- 229940125396 insulin Drugs 0.000 claims description 4
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- 239000011664 nicotinic acid Substances 0.000 claims description 4
- 235000001968 nicotinic acid Nutrition 0.000 claims description 4
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 4
- 229940031439 squalene Drugs 0.000 claims 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 claims description 4
- 239000005495 thyroid hormone Substances 0.000 claims description 4
- 229940036555 thyroid hormone Drugs 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- KCJKKFMNAXDVEL-UHFFFAOYSA-N 2-phenyl-4-(2,4,5-trichlorophenoxy)pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=C(Cl)C=C1Cl KCJKKFMNAXDVEL-UHFFFAOYSA-N 0.000 claims description 3
- BUAKMFBGWYVGCD-UHFFFAOYSA-N 4-(2,3-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=CC(OC=2C(=CN=C(N=2)C=2C=CC=CC=2)C(O)=O)=C1C BUAKMFBGWYVGCD-UHFFFAOYSA-N 0.000 claims description 3
- WDZBQJRINYWGMV-UHFFFAOYSA-N 4-(2-methylphenoxy)-2-phenylpyrimidine-5-carboxylic acid Chemical compound CC1=CC=CC=C1OC1=NC(C=2C=CC=CC=2)=NC=C1C(O)=O WDZBQJRINYWGMV-UHFFFAOYSA-N 0.000 claims description 3
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 claims description 3
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 claims description 3
- 229940127470 Lipase Inhibitors Drugs 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- 229940127219 anticoagulant drug Drugs 0.000 claims description 3
- 230000001906 cholesterol absorption Effects 0.000 claims description 3
- 229940030606 diuretics Drugs 0.000 claims description 3
- WWXARJSFXLLRPG-UHFFFAOYSA-N ethyl 2-phenyl-4-(2,4,5-trichlorophenoxy)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC(Cl)=C(Cl)C=C1Cl WWXARJSFXLLRPG-UHFFFAOYSA-N 0.000 claims description 3
- BMUIXCLLFWRJOQ-UHFFFAOYSA-N ethyl 4-(2,3-dimethylphenoxy)-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1OC1=CC=CC(C)=C1C BMUIXCLLFWRJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 126
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 66
- 238000005160 1H NMR spectroscopy Methods 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000000203 mixture Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000004128 high performance liquid chromatography Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000012071 phase Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 238000007429 general method Methods 0.000 description 23
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 235000011181 potassium carbonates Nutrition 0.000 description 20
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 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 17
- 235000019253 formic acid Nutrition 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 description 14
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
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- 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 7
- 239000000047 product Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- 239000000725 suspension Substances 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000008214 LDL Cholesterol Methods 0.000 description 4
- 102000007330 LDL Lipoproteins Human genes 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229960004676 antithrombotic agent Drugs 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000007257 deesterification reaction Methods 0.000 description 4
- 229940012952 fibrinogen Drugs 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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Landscapes
- Health & Medical Sciences (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005011447.4 | 2005-03-12 | ||
| DE102005011447 | 2005-03-12 | ||
| DE102005027150A DE102005027150A1 (de) | 2005-03-12 | 2005-06-11 | Pyrimidincarbonsäure-Derivate und ihre Verwendung |
| DE102005027150.2 | 2005-06-11 | ||
| PCT/EP2006/002054 WO2006097220A1 (de) | 2005-03-12 | 2006-03-07 | Pyrimidincarbonsäure-derivate und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2600681A1 true CA2600681A1 (en) | 2006-09-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002600681A Abandoned CA2600681A1 (en) | 2005-03-12 | 2006-03-07 | Pyrimidine carboxylic acid derivatives and use thereof |
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| Country | Link |
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| US (1) | US20080194598A1 (https=) |
| EP (1) | EP1866289A1 (https=) |
| JP (1) | JP2008533063A (https=) |
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| AU (1) | AU2006224812A1 (https=) |
| BR (1) | BRPI0609207A2 (https=) |
| CA (1) | CA2600681A1 (https=) |
| DE (1) | DE102005027150A1 (https=) |
| DO (1) | DOP2006000062A (https=) |
| GT (1) | GT200600109A (https=) |
| IL (1) | IL185895A0 (https=) |
| MX (1) | MX2007011070A (https=) |
| PE (1) | PE20061348A1 (https=) |
| TW (1) | TW200724532A (https=) |
| UY (1) | UY29416A1 (https=) |
| WO (1) | WO2006097220A1 (https=) |
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| GEP20105099B (en) | 2005-05-06 | 2010-10-25 | Du Pont | Method for preparation of optionally 2-substituted 1,6- dihydrocarboxil acids |
| DE102006043520A1 (de) * | 2006-09-12 | 2008-03-27 | Bayer Healthcare Ag | 2-Phenoxynikotinsäure-Derivate und ihre Verwendung |
| DE102006043519A1 (de) * | 2006-09-12 | 2008-03-27 | Bayer Healthcare Ag | 4-Phenoxynikotinsäure-Derivate und ihre Verwendung |
| EP2155195B1 (en) * | 2007-04-13 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor |
| DE102007042754A1 (de) * | 2007-09-07 | 2009-03-12 | Bayer Healthcare Ag | Substituierte 6-Phenylnikotinsäuren und ihre Verwendung |
| DE102007061757A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 2-Phenylpyrimidin-5-carbonsäuren und ihre Verwendung |
| DE102007061756A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 4-Aminopyrimidin-5-carbonsäuren und ihre Verwendung |
| EP2575821B1 (en) | 2010-05-26 | 2015-08-12 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| RU2013114390A (ru) | 2010-08-31 | 2014-10-10 | СНУ Ар энд ДиБи ФАУНДЕЙШН | Применение фетального репрограммирования посредством ppar-дельта-агониста |
| CA2852957C (en) | 2011-10-28 | 2020-08-04 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease |
| CN104023727B (zh) | 2011-10-28 | 2017-04-05 | 鲁美纳医药公司 | 用于治疗小儿胆汁淤积性肝病的胆汁酸再循环抑制剂 |
| US20140275090A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| CN105228615A (zh) | 2013-03-15 | 2016-01-06 | 鲁美纳医药公司 | 用于治疗巴雷特食管和胃食管返流疾病的胆汁酸再循环抑制剂 |
| PL3923943T3 (pl) | 2019-02-12 | 2024-12-09 | Mirum Pharmaceuticals, Inc. | Zależna od genotypu i dawki odpowiedź na asbti u pacjentów z niedoborem pompy eksportu soli żółciowych |
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| NZ515086A (en) * | 1999-04-28 | 2003-10-31 | Aventis Pharma Gmbh | Di-aryl acid derivatives as PPAR receptor ligands |
| YU39503A (sh) * | 2000-11-22 | 2006-05-25 | F. Hoffmann-La Roche Ag. | Derivati pirimidina |
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- 2006-03-09 AR ARP060100888A patent/AR055744A1/es not_active Application Discontinuation
- 2006-03-10 PE PE2006000274A patent/PE20061348A1/es not_active Application Discontinuation
- 2006-03-10 TW TW095108034A patent/TW200724532A/zh unknown
- 2006-03-10 DO DO2006000062A patent/DOP2006000062A/es unknown
- 2006-03-10 GT GT200600109A patent/GT200600109A/es unknown
- 2006-03-10 UY UY29416A patent/UY29416A1/es not_active Application Discontinuation
-
2007
- 2007-09-11 IL IL185895A patent/IL185895A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DOP2006000062A (es) | 2006-12-15 |
| GT200600109A (es) | 2007-02-14 |
| KR20070116876A (ko) | 2007-12-11 |
| AU2006224812A1 (en) | 2006-09-21 |
| US20080194598A1 (en) | 2008-08-14 |
| PE20061348A1 (es) | 2007-01-28 |
| TW200724532A (en) | 2007-07-01 |
| WO2006097220A1 (de) | 2006-09-21 |
| DE102005027150A1 (de) | 2006-09-28 |
| EP1866289A1 (de) | 2007-12-19 |
| MX2007011070A (es) | 2007-11-07 |
| JP2008533063A (ja) | 2008-08-21 |
| AR055744A1 (es) | 2007-09-05 |
| BRPI0609207A2 (pt) | 2010-03-02 |
| IL185895A0 (en) | 2008-01-06 |
| UY29416A1 (es) | 2006-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |