JP6368367B2 - 置換オキソピリジン誘導体 - Google Patents

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Publication number

JP6368367B2

JP6368367B2 JP2016526776A JP2016526776A JP6368367B2 JP 6368367 B2 JP6368367 B2 JP 6368367B2 JP 2016526776 A JP2016526776 A JP 2016526776A JP 2016526776 A JP2016526776 A JP 2016526776A JP 6368367 B2 JP6368367 B2 JP 6368367B2

Authority

JP

Japan

Prior art keywords

methoxy

mmol

chlorine

chloro

represents hydrogen

Prior art date

2013-10-30

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

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 claims description 163
• -1 methoxy, difluoromethoxy Chemical group 0.000 claims description 154
• 229910052739 hydrogen Inorganic materials 0.000 claims description 122
• 239000001257 hydrogen Substances 0.000 claims description 122
• 150000002431 hydrogen Chemical class 0.000 claims description 86
• 239000000460 chlorine Substances 0.000 claims description 83
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 82
• 229910052801 chlorine Inorganic materials 0.000 claims description 82
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 62
• 208000035475 disorder Diseases 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 238000011282 treatment Methods 0.000 claims description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
• 229910052731 fluorine Inorganic materials 0.000 claims description 45
• 239000011737 fluorine Substances 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
• 230000002265 prevention Effects 0.000 claims description 34
• 239000012453 solvate Substances 0.000 claims description 29
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
• 229910052794 bromium Inorganic materials 0.000 claims description 25
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 230000009424 thromboembolic effect Effects 0.000 claims description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 17
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 239000011630 iodine Substances 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 230000001732 thrombotic effect Effects 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
• 206010019860 Hereditary angioedema Diseases 0.000 claims description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
• 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 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 6
• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 6
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000003566 oxetanyl group Chemical group 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 claims description 5
• 208000030533 eye disease Diseases 0.000 claims description 5
• 230000000968 intestinal effect Effects 0.000 claims description 5
• VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 5
• 208000022873 Ocular disease Diseases 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 230000006806 disease prevention Effects 0.000 claims description 4
• 238000010931 ester hydrolysis Methods 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
• PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims description 2
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 2
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
• NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 321
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 276
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 230
• 238000000034 method Methods 0.000 description 174
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• 239000000203 mixture Substances 0.000 description 171
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 148
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 119
• 235000019439 ethyl acetate Nutrition 0.000 description 107
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 104
• 238000005160 1H NMR spectroscopy Methods 0.000 description 103
• 230000002829 reductive effect Effects 0.000 description 101
• 238000007429 general method Methods 0.000 description 98
• 239000000243 solution Substances 0.000 description 97
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• 239000012043 crude product Substances 0.000 description 88
• 239000012071 phase Substances 0.000 description 84
• 239000011541 reaction mixture Substances 0.000 description 60
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 57
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 56
• 239000012074 organic phase Substances 0.000 description 50
• 239000002904 solvent Substances 0.000 description 48
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 44
• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 42
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 39
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 38
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
• 229920006395 saturated elastomer Polymers 0.000 description 38
• 238000003818 flash chromatography Methods 0.000 description 36
• 239000008346 aqueous phase Substances 0.000 description 35
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
• 229910052938 sodium sulfate Inorganic materials 0.000 description 34
• 235000011152 sodium sulphate Nutrition 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 30
• 238000002953 preparative HPLC Methods 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 108090000113 Plasma Kallikrein Proteins 0.000 description 26
• 230000015271 coagulation Effects 0.000 description 26
• 238000005345 coagulation Methods 0.000 description 26
• 238000004007 reversed phase HPLC Methods 0.000 description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
• 102000003827 Plasma Kallikrein Human genes 0.000 description 24
• 230000015572 biosynthetic process Effects 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 24
• 229910002027 silica gel Inorganic materials 0.000 description 24
• 239000003112 inhibitor Substances 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
• 235000019341 magnesium sulphate Nutrition 0.000 description 22
• 239000011780 sodium chloride Substances 0.000 description 22
• 108010080805 Factor XIa Proteins 0.000 description 21
• 229910052786 argon Inorganic materials 0.000 description 21
• 238000004587 chromatography analysis Methods 0.000 description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
• 238000001994 activation Methods 0.000 description 20
• 239000012442 inert solvent Substances 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• 239000002253 acid Substances 0.000 description 19
• 230000004913 activation Effects 0.000 description 19
• 230000008569 process Effects 0.000 description 19
• 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 18
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 235000019253 formic acid Nutrition 0.000 description 18
• 238000005191 phase separation Methods 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• 108090000190 Thrombin Proteins 0.000 description 15
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 15
• 229910052763 palladium Inorganic materials 0.000 description 15
• 229960004072 thrombin Drugs 0.000 description 15
• 238000000825 ultraviolet detection Methods 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 230000004054 inflammatory process Effects 0.000 description 12
• 239000011259 mixed solution Substances 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 235000011181 potassium carbonates Nutrition 0.000 description 12
• 208000002815 pulmonary hypertension Diseases 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• 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 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 229960001701 chloroform Drugs 0.000 description 11
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• RPNDTVKJMHEOMY-UHFFFAOYSA-N 4-chloro-2-[5-methoxy-1-(4-methoxybutan-2-yl)-2-oxopyridin-4-yl]benzonitrile Chemical compound COCCC(C)n1cc(OC)c(cc1=O)-c1cc(Cl)ccc1C#N RPNDTVKJMHEOMY-UHFFFAOYSA-N 0.000 description 10
• 208000032843 Hemorrhage Diseases 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 208000007536 Thrombosis Diseases 0.000 description 10
• 208000034158 bleeding Diseases 0.000 description 10
• 230000000740 bleeding effect Effects 0.000 description 10
• FBEUDMIHYYXAJG-UHFFFAOYSA-N imidazo[1,2-a]pyridin-6-amine Chemical compound C1=C(N)C=CC2=NC=CN21 FBEUDMIHYYXAJG-UHFFFAOYSA-N 0.000 description 10
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 206010061218 Inflammation Diseases 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000003146 anticoagulant agent Substances 0.000 description 9
• 230000001684 chronic effect Effects 0.000 description 9
• 230000008878 coupling Effects 0.000 description 9
• 238000010168 coupling process Methods 0.000 description 9
• 238000005859 coupling reaction Methods 0.000 description 9
• 230000019491 signal transduction Effects 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• 239000003643 water by type Substances 0.000 description 9
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
• SNEKBLQWKWIZOH-UHFFFAOYSA-N 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1-yl]butanoic acid Chemical compound ClC=1C=CC(=C(C1)C1=CC(N(C=C1OC)C(C(=O)O)CC)=O)C#N SNEKBLQWKWIZOH-UHFFFAOYSA-N 0.000 description 8
• 206010012689 Diabetic retinopathy Diseases 0.000 description 8
• 239000005909 Kieselgur Substances 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 235000019270 ammonium chloride Nutrition 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 150000002170 ethers Chemical class 0.000 description 8
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 8
• 150000008282 halocarbons Chemical class 0.000 description 8
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
• 238000000926 separation method Methods 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 7
• 108010071241 Factor XIIa Proteins 0.000 description 7
• 208000001344 Macular Edema Diseases 0.000 description 7
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 7
• 108010000499 Thromboplastin Proteins 0.000 description 7
• 102000002262 Thromboplastin Human genes 0.000 description 7
• 230000006378 damage Effects 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• PKWHXLCNUIXDIK-UHFFFAOYSA-N ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate Chemical compound C1=C(N)C=CC2=NC(C(=O)OCC)=CN21 PKWHXLCNUIXDIK-UHFFFAOYSA-N 0.000 description 7
• 229920000669 heparin Polymers 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
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