DK2669270T3 - Indole-related compounds such as URAT1 inhibitors - Google Patents

Indole-related compounds such as URAT1 inhibitors Download PDF

Info

Publication number: DK2669270T3
Authority: DK; Denmark
Prior art keywords: group; compound; formula; methyl; synthesis
Prior art date: 2011-01-28

Application number

DK12739424.5T

Other languages

Danish (da)

English (en)

Inventor

Keita Nagai

Koh Nagasawa

Hirobumi Takahashi

Motoaki BABA

Shinichi Fujioka

Eri KONDOH

Kenichi Tanaka

Yoshiki Itoh

Original Assignee

Sato Pharma

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.)

2011-01-28

Filing date

2012-01-30

Publication date

2018-02-26

2012-01-30 Application filed by Sato Pharma filed Critical Sato Pharma

2018-02-26 Application granted granted Critical

2018-02-26 Publication of DK2669270T3 publication Critical patent/DK2669270T3/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 873
229940083914 URAT1 inhibitor Drugs 0.000 title abstract description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims abstract description 93
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims abstract description 85
229940116269 uric acid Drugs 0.000 claims abstract description 85
210000004369 blood Anatomy 0.000 claims abstract description 43
239000008280 blood Substances 0.000 claims abstract description 43
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 5
-1 5-tetrazolyl group Chemical group 0.000 claims description 209
150000003839 salts Chemical class 0.000 claims description 51
125000001424 substituent group Chemical group 0.000 claims description 50
125000005843 halogen group Chemical group 0.000 claims description 32
201000001431 Hyperuricemia Diseases 0.000 claims description 25
201000005569 Gout Diseases 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
230000001575 pathological effect Effects 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
206010007027 Calculus urinary Diseases 0.000 claims description 11
208000008281 urolithiasis Diseases 0.000 claims description 11
208000029078 coronary artery disease Diseases 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
230000001154 acute effect Effects 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
230000001684 chronic effect Effects 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
208000031225 myocardial ischemia Diseases 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
KKEHRCXNWIVIHK-UHFFFAOYSA-N 1-[(2-chloro-6-cyclopropylphenyl)methyl]-3-methyl-6-(2h-tetrazol-5-yl)pyrazolo[4,3-b]pyridine Chemical compound C12=CC(C=3NN=NN=3)=CN=C2C(C)=NN1CC1=C(Cl)C=CC=C1C1CC1 KKEHRCXNWIVIHK-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
NWGJXPHFILWYCU-UHFFFAOYSA-N 1-[(2-chloro-6-methylphenyl)methyl]-3-methyl-6-(2h-tetrazol-5-yl)pyrazolo[4,3-b]pyridine Chemical compound C12=CC(C=3NN=NN=3)=CN=C2C(C)=NN1CC1=C(C)C=CC=C1Cl NWGJXPHFILWYCU-UHFFFAOYSA-N 0.000 claims description 3
NZOSXOVFKQTUAJ-UHFFFAOYSA-N 3-chloro-1-[(2-chloro-6-methylphenyl)methyl]-6-(2h-tetrazol-5-yl)pyrazolo[4,3-b]pyridine Chemical compound CC1=CC=CC(Cl)=C1CN1C2=CC(C=3NN=NN=3)=CN=C2C(Cl)=N1 NZOSXOVFKQTUAJ-UHFFFAOYSA-N 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
229910052705 radium Inorganic materials 0.000 claims description 3
229910052701 rubidium Inorganic materials 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
DEEJHEPZVXORGD-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-3-methyl-6-(2h-tetrazol-5-ylmethyl)indazole Chemical compound C12=CC(CC=3NN=NN=3)=CC=C2C(C)=NN1CC1=C(Cl)C=CC=C1Cl DEEJHEPZVXORGD-UHFFFAOYSA-N 0.000 claims description 2
206010018634 Gouty Arthritis Diseases 0.000 claims 4
206010039073 rheumatoid arthritis Diseases 0.000 claims 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
230000003907 kidney function Effects 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
101000821903 Homo sapiens Solute carrier family 22 member 12 Proteins 0.000 abstract description 26
102100021495 Solute carrier family 22 member 12 Human genes 0.000 abstract description 25
239000003638 chemical reducing agent Substances 0.000 abstract description 18
230000002401 inhibitory effect Effects 0.000 abstract description 14
ASUMVAPLXCRBMA-UHFFFAOYSA-N (3,5-dichloro-4-hydroxyphenyl)-(2,3-dihydro-1,4-benzoxazin-4-yl)methanone Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2OCC1 ASUMVAPLXCRBMA-UHFFFAOYSA-N 0.000 abstract description 12
238000000034 method Methods 0.000 description 379
230000008569 process Effects 0.000 description 234
238000003786 synthesis reaction Methods 0.000 description 225
230000015572 biosynthetic process Effects 0.000 description 217
239000011541 reaction mixture Substances 0.000 description 215
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 186
239000007787 solid Substances 0.000 description 180
238000005160 1H NMR spectroscopy Methods 0.000 description 141
239000000243 solution Substances 0.000 description 115
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 107
230000002829 reductive effect Effects 0.000 description 103
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 94
239000000706 filtrate Substances 0.000 description 86
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 83
238000006243 chemical reaction Methods 0.000 description 82
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 78
239000012044 organic layer Substances 0.000 description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
125000006239 protecting group Chemical group 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 66
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 62
238000010898 silica gel chromatography Methods 0.000 description 62
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
239000003795 chemical substances by application Substances 0.000 description 57
XUJCMGVPFWXYGV-UHFFFAOYSA-N 2-(1-benzylindol-6-yl)acetic acid Chemical compound C12=CC(CC(=O)O)=CC=C2C=CN1CC1=CC=CC=C1 XUJCMGVPFWXYGV-UHFFFAOYSA-N 0.000 description 55
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 55
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 47
239000007864 aqueous solution Substances 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 37
238000004519 manufacturing process Methods 0.000 description 37
239000000203 mixture Substances 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000002585 base Substances 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
229910000027 potassium carbonate Inorganic materials 0.000 description 31
239000002904 solvent Substances 0.000 description 29
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 28
238000009472 formulation Methods 0.000 description 27
239000003054 catalyst Substances 0.000 description 26
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 26
HPVRFWQMBYLJRL-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CCl HPVRFWQMBYLJRL-UHFFFAOYSA-N 0.000 description 24
231100000989 no adverse effect Toxicity 0.000 description 24
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
239000002253 acid Substances 0.000 description 23
239000007810 chemical reaction solvent Substances 0.000 description 23
238000001816 cooling Methods 0.000 description 23
239000003814 drug Substances 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
229940079593 drug Drugs 0.000 description 22
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 21
229910052763 palladium Inorganic materials 0.000 description 21
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
239000012267 brine Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 16
230000020477 pH reduction Effects 0.000 description 16
206010003246 arthritis Diseases 0.000 description 15
239000012230 colorless oil Substances 0.000 description 15
230000006870 function Effects 0.000 description 15
PPYQJSQNYMYOQT-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-3-methylindol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=CN1CC1=C(C)C=CC=C1C PPYQJSQNYMYOQT-UHFFFAOYSA-N 0.000 description 14
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 14
239000003446 ligand Substances 0.000 description 14
229910000073 phosphorus hydride Inorganic materials 0.000 description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
230000029142 excretion Effects 0.000 description 13
210000003734 kidney Anatomy 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
235000011054 acetic acid Nutrition 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000004305 biphenyl Substances 0.000 description 11
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
238000013268 sustained release Methods 0.000 description 11
239000012730 sustained-release form Substances 0.000 description 11
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
235000019270 ammonium chloride Nutrition 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
125000001309 chloro group Chemical group Cl* 0.000 description 10
239000007788 liquid Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
208000031226 Hyperlipidaemia Diseases 0.000 description 9
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 9
NBBGUEGQPMVZDY-UHFFFAOYSA-N methyl 2-(3-methyl-1h-indol-6-yl)acetate Chemical compound COC(=O)CC1=CC=C2C(C)=CNC2=C1 NBBGUEGQPMVZDY-UHFFFAOYSA-N 0.000 description 9
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
238000001308 synthesis method Methods 0.000 description 9
IGVKHDGKBABWAV-UHFFFAOYSA-N 1-[(2,6-dimethylphenyl)methyl]-2-methylindole-6-carboxylic acid Chemical compound CC1=CC2=CC=C(C(O)=O)C=C2N1CC1=C(C)C=CC=C1C IGVKHDGKBABWAV-UHFFFAOYSA-N 0.000 description 8
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
WFXSJPPRURCWCL-UHFFFAOYSA-N 4-[1-[(2,6-dimethylphenyl)methyl]indol-6-yl]-4-oxobutanoic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(C(=O)CCC(O)=O)=CC=C2C=C1 WFXSJPPRURCWCL-UHFFFAOYSA-N 0.000 description 8
108010078791 Carrier Proteins Proteins 0.000 description 8
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
208000008589 Obesity Diseases 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 8
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
230000002140 halogenating effect Effects 0.000 description 8
235000020824 obesity Nutrition 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
ZCGRJOYZGDEGBO-VQHVLOKHSA-N (e)-3-[1-[(2,6-dimethylphenyl)methyl]indol-6-yl]prop-2-enoic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(\C=C\C(O)=O)=CC=C2C=C1 ZCGRJOYZGDEGBO-VQHVLOKHSA-N 0.000 description 7
MZERFRNAEKUXQK-UHFFFAOYSA-N 1-[(2,6-dimethylphenyl)methyl]indazole-6-carboxylic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(C(O)=O)=CC=C2C=N1 MZERFRNAEKUXQK-UHFFFAOYSA-N 0.000 description 7
FSJQUSZJKNWCRO-UHFFFAOYSA-N 2-[1-[(2,3-dichlorophenyl)methyl]-3-methylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=NN1CC1=CC=CC(Cl)=C1Cl FSJQUSZJKNWCRO-UHFFFAOYSA-N 0.000 description 7
POZMFUCEDVKJET-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-3-methylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=NN1CC1=C(Cl)C=CC=C1Cl POZMFUCEDVKJET-UHFFFAOYSA-N 0.000 description 7
LWMWFNZVGKSTIH-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-2,3-dihydroindol-6-yl]acetic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(CC(O)=O)=CC=C2CC1 LWMWFNZVGKSTIH-UHFFFAOYSA-N 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
FCICZWOEFTVPJX-UHFFFAOYSA-N 3-[(2,6-dimethylphenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(C(O)=O)=CC=C2N=C1 FCICZWOEFTVPJX-UHFFFAOYSA-N 0.000 description 7
JXHBSSVESZVJSH-UHFFFAOYSA-N 3-[1-[(2,6-dimethylphenyl)methyl]indol-6-yl]-3-hydroxypropanoic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(C(O)CC(O)=O)=CC=C2C=C1 JXHBSSVESZVJSH-UHFFFAOYSA-N 0.000 description 7
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KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
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DYHMGCXIWVASHA-UHFFFAOYSA-N methyl 1-[(2,6-dimethylphenyl)methyl]-2,3-dihydroindole-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2CCN1CC1=C(C)C=CC=C1C DYHMGCXIWVASHA-UHFFFAOYSA-N 0.000 description 4
XSFCGOYXSWQLRV-UHFFFAOYSA-N methyl 1-[(2,6-dimethylphenyl)methyl]-3-ethylindole-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2C(CC)=CN1CC1=C(C)C=CC=C1C XSFCGOYXSWQLRV-UHFFFAOYSA-N 0.000 description 4
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AXKWXKIIQFKMMJ-UHFFFAOYSA-N methyl 1-[(2,6-dimethylphenyl)methyl]indole-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2C=CN1CC1=C(C)C=CC=C1C AXKWXKIIQFKMMJ-UHFFFAOYSA-N 0.000 description 4
FHELGHUHAZYSGO-UHFFFAOYSA-N methyl 1-[(2,6-dimethylphenyl)methyl]pyrrolo[3,2-b]pyridine-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CN=C2C=CN1CC1=C(C)C=CC=C1C FHELGHUHAZYSGO-UHFFFAOYSA-N 0.000 description 4
LLMZNFRVOLCGPX-UHFFFAOYSA-N methyl 2-(1-benzyl-2,3-dihydroindol-6-yl)acetate Chemical compound C12=CC(CC(=O)OC)=CC=C2CCN1CC1=CC=CC=C1 LLMZNFRVOLCGPX-UHFFFAOYSA-N 0.000 description 4
PKHBFWMPKJLKRQ-UHFFFAOYSA-N methyl 2-(3,3-dimethyl-1,2-dihydroindol-6-yl)acetate Chemical compound COC(=O)CC1=CC=C2C(C)(C)CNC2=C1 PKHBFWMPKJLKRQ-UHFFFAOYSA-N 0.000 description 4
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230000037361 pathway Effects 0.000 description 1
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FEDSNBHHWZEYTP-ZFQYHYQMSA-N penbutolol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 FEDSNBHHWZEYTP-ZFQYHYQMSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 description 1
229960003929 perindopril erbumine Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
BZBAYMUKLAYQEO-UHFFFAOYSA-N phenylborane Chemical compound BC1=CC=CC=C1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
239000002590 phosphodiesterase V inhibitor Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
208000030761 polycystic kidney disease Diseases 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
UQASFTAPAVXIOT-UHFFFAOYSA-M potassium;2-[1-[(2,6-dimethylphenyl)methyl]-2,3-dihydroindol-6-yl]acetate Chemical compound [K+].CC1=CC=CC(C)=C1CN1C2=CC(CC([O-])=O)=CC=C2CC1 UQASFTAPAVXIOT-UHFFFAOYSA-M 0.000 description 1
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TUZYXOIXSAXUGO-PZAWKZKUSA-M pravastatin(1-) 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-M 0.000 description 1
229960002386 prazosin hydrochloride Drugs 0.000 description 1
WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
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FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
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MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
GMDGXJQUWIQOLE-UHFFFAOYSA-N prop-2-enylborane Chemical class BCC=C GMDGXJQUWIQOLE-UHFFFAOYSA-N 0.000 description 1
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PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
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IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
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239000001632 sodium acetate Substances 0.000 description 1
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WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
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
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
RRWFKUFMWAQPAL-UHFFFAOYSA-N sodium;dicyclohexylazanide Chemical compound [Na+].C1CCCCC1[N-]C1CCCCC1 RRWFKUFMWAQPAL-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
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241000894007 species Species 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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150000003892 tartrate salts Chemical class 0.000 description 1
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FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960001909 terazosin hydrochloride Drugs 0.000 description 1
JPPXEBLKCSJFQO-UHFFFAOYSA-N tert-butyl 1h-indole-6-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=C2C=CNC2=C1 JPPXEBLKCSJFQO-UHFFFAOYSA-N 0.000 description 1
RTZRUVMEWWPNRR-UHFFFAOYSA-N tert-butyl n-(3-iodo-1h-pyrrolo[2,3-b]pyridin-5-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CN=C2NC=C(I)C2=C1 RTZRUVMEWWPNRR-UHFFFAOYSA-N 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
239000003451 thiazide diuretic agent Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229950008411 tilisolol Drugs 0.000 description 1
PCTNAMGLSYHIPL-UHFFFAOYSA-N tin(4+) tetraazide Chemical class [Sn+4].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] PCTNAMGLSYHIPL-UHFFFAOYSA-N 0.000 description 1
OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
208000012175 toxemia of pregnancy Diseases 0.000 description 1
229960002051 trandolapril Drugs 0.000 description 1
230000032258 transport Effects 0.000 description 1
REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
239000000814 tuberculostatic agent Substances 0.000 description 1
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210000002700 urine Anatomy 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1
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229940102001 zinc bromide Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
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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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
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Chemical Kinetics & Catalysis (AREA)
Urology & Nephrology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DK12739424.5T 2011-01-28 2012-01-30 Indole-related compounds such as URAT1 inhibitors DK2669270T3 (en)

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JP2011016950		2011-01-28
PCT/JP2012/052009 WO2012102405A1 (ja)	2011-01-28	2012-01-30	縮環化合物

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US (2)	US8987473B2 (2)
EP (1)	EP2669270B1 (2)
JP (2)	JP5990106B2 (2)
DK (1)	DK2669270T3 (2)
WO (1)	WO2012102405A1 (2)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2013096496A2 (en) *	2011-12-21	2013-06-27	Allergan, Inc.	Compounds acting at multiple prostaglandin receptors giving a general anti-inflammatory response
WO2014017643A1 (ja)	2012-07-27	2014-01-30	佐藤製薬株式会社	ジフルオロメチレン化合物
CN102875590A (zh) *	2012-10-22	2013-01-16	北京林业大学	芳香族三丁基锡衍生物的制备方法
AU2016236669B2 (en)	2015-03-24	2018-11-08	Shanghai Yingli Pharmaceutical Co., Ltd	Condensed ring derivative, and preparation method, intermediate, pharmaceutical composition and use thereof
CN108473495B (zh)	2015-11-20	2022-04-12	福马治疗有限公司	作为泛素-特异性蛋白酶1抑制剂的嘌呤酮
CN106045898B (zh) *	2016-06-28	2019-05-24	广东东阳光药业有限公司	一种吲哚类化合物及其制备方法和用途
CN106146533B (zh) *	2016-07-14	2018-04-03	华润赛科药业有限责任公司	含硫杂环羧酸类衍生物、其制备方法和应用
CN110121359A (zh)	2016-11-11	2019-08-13	怀特黑德生物制剂研究所	人血浆培养基
TWI774755B (zh) *	2017-04-28	2022-08-21	日商佐藤製藥股份有限公司	二氟甲烯化合物之製造法
AU2018281131B2 (en)	2017-06-08	2022-01-20	Merck Sharp & Dohme Corp.	Pyrazolopyrimidine PDE9 inhibitors
WO2018234807A1 (en) *	2017-06-22	2018-12-27	Curadev Pharma Limited	Heterocyclic small molecule modulators of human sting
MX2021003904A (es)	2018-10-05	2021-10-26	Annapurna Bio Inc	Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor apj.
TW202112774A (zh) *	2019-06-14	2021-04-01	比利時商健生藥品公司	經取代之吡唑并－吡啶醯胺及其作為ｇｌｕｎ２ｂ受體調節劑之用途
CA3143103A1 (en)	2019-06-14	2020-12-17	Janssen Pharmaceutica Nv	Pyridine carbamates and their use as glun2b receptor modulators
BR112021025141A2 (pt)	2019-06-14	2022-01-25	Janssen Pharmaceutica Nv	Pirazolo-piridinas heteroaromáticas substituídas e seu uso como moduladores do receptor glun2b
CN114008052A (zh)	2019-06-14	2022-02-01	詹森药业有限公司	取代的吡唑并-吡嗪以及它们作为GluN2B受体调节剂的用途
MX2021015511A (es)	2019-06-14	2022-01-31	Janssen Pharmaceutica Nv	Carbamatos de pirazina y sus usos como moduladores del receptor glun2b.
GB202013728D0 (en) *	2020-09-01	2020-10-14	Nrg Therapeutics Ltd	Novel compounds
KR20230104781A (ko)	2020-10-05	2023-07-10	인라이븐 테라퓨틱스, 인크.	Bcr-abl 티로신 키나아제의 억제를 위한 5- 및 6-아자인돌 화합물
PT4426434T (pt)	2021-11-02	2025-11-24	Flare Therapeutics Inc	Agonistas inversos de pparg e suas utilizações
CN116715633B (zh) *	2022-04-27	2025-08-12	杭州新元素药业股份有限公司	可用于降尿酸的化合物
WO2026008750A1 (en)	2024-07-05	2026-01-08	Syngenta Crop Protection Ag	Novel carboxamide compounds

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0470543A1 (de) *	1990-08-10	1992-02-12	Dr. Karl Thomae GmbH	Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung
GB9121776D0 (en) *	1991-10-14	1991-11-27	Fujisawa Pharmaceutical Co	Benzimidazole derivatives and process for preparation thereof
HUT76923A (hu)	1994-07-27	1998-01-28	Sankyo Company Limited	Muszkarinreceptorokra alloszterikus hatást kifejtő heterociklusos vegyületek
CA2217707A1 (en)	1995-04-10	1996-10-17	Fujisawa Pharmaceutial Co., Ltd.	Indole derivatives as cgmp-pde inhibitors
US6045398A (en) *	1995-07-10	2000-04-04	International Business Machines Corporation	Battery accepting unit and battery pack
WO1997024334A1 (en)	1995-12-28	1997-07-10	Fujisawa Pharmaceutical Co., Ltd.	Benzimidazole derivatives
AUPO118896A0 (en) *	1996-07-23	1996-08-15	Fujisawa Pharmaceutical Co., Ltd.	New use
AU3899097A (en) *	1996-08-05	1998-02-25	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Substituted aromatic compounds
AU4400597A (en)	1996-10-08	1998-05-05	Fujisawa Pharmaceutical Co., Ltd.	Indole derivatives
JPH10114654A (ja) *	1996-10-09	1998-05-06	Fujisawa Pharmaceut Co Ltd	新規用途
AU745081B2 (en) *	1997-06-27	2002-03-14	Fujisawa Pharmaceutical Co., Ltd.	Sulfonamide compounds and medicinal use thereof
TW453999B (en)	1997-06-27	2001-09-11	Fujisawa Pharmaceutical Co	Benzimidazole derivatives
US6410584B1 (en) *	1998-01-14	2002-06-25	Cell Pathways, Inc.	Method for inhibiting neoplastic cells with indole derivatives
US6358992B1 (en) *	1998-11-25	2002-03-19	Cell Pathways, Inc.	Method of inhibiting neoplastic cells with indole derivatives
WO2000039099A1 (en) *	1998-12-24	2000-07-06	Fujisawa Pharmaceutical Co., Ltd.	Benzimidazole derivatives
JP2003513075A (ja) *	1999-11-05	2003-04-08	スミスクラインビーチャムパブリックリミテッドカンパニー	複合５ｈｔ１ａ、５ｈｔ１ｂおよび５ｈｔ１ｄ受容体活性を有するイソキノリンおよびキナゾリン誘導体
EP1460067A4 (en) *	2001-11-26	2005-12-07	Takeda Pharmaceutical	BICYCLIC DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE
AU2003902860A0 (en)	2003-06-06	2003-06-26	Daicel Chemical Industries, Ltd	Benzimidazole compounds
AR051780A1 (es)	2004-11-29	2007-02-07	Japan Tobacco Inc	Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos
EP1985297A1 (en)	2006-01-27	2008-10-29	Japan Tobacco, Inc.	Carboxylic acid compound and use thereof
US20070197512A1 (en)	2006-01-27	2007-08-23	Japan Tobacco Inc.	Carboxylic Acid Compounds and Use Thereof
WO2007097197A1 (ja)	2006-02-20	2007-08-30	Astellas Pharma Inc.	アミド誘導体またはその塩
KR20080114711A (ko)	2006-03-02	2008-12-31	아스텔라스세이야쿠 가부시키가이샤	17β ＨＳＤ 타입 5 저해제
US8338416B2 (en)	2006-03-16	2012-12-25	Pharmacylics, Inc.	Indole derivatives as inhibitors of histone deacetylase
MX337906B (es) *	2006-10-19	2016-03-28	Signal Pharm Llc	Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas.
BRPI0807961A2 (pt) *	2007-02-13	2017-05-16	Pharmacopeia Llc	agonista de alfa2c adrenorreceptor funcionalmente seletivos.
JP5330989B2 (ja)	2007-04-11	2013-10-30	キッセイ薬品工業株式会社	（アザ）インドール誘導体及びその医薬用途
US9149463B2 (en)	2007-09-18	2015-10-06	The Board Of Trustees Of The Leland Standford Junior University	Methods and compositions of treating a Flaviviridae family viral infection
UA109638C2 (uk)	2008-03-13	2015-09-25		Сполуки та спосіб зниження рівня сечової кислоти
CA2875549A1 (en) *	2008-04-15	2009-10-22	Pharmacyclics, Inc.	Selective inhibitors of histone deacetylase
KR101048448B1 (ko) *	2008-11-21	2011-07-11	한국화학연구원	신규 피라졸로[4,3-ｂ]피리딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물
EP2408449A4 (en)	2009-03-18	2012-08-08	Univ Leland Stanford Junior	METHOD AND COMPOSITIONS FOR TREATING FLAVIVIRIDAE VIRUS INFECTIONS
JP2011246389A (ja) *	2010-05-26	2011-12-08	Oncotherapy Science Ltd	Ｔｔｋ阻害作用を有する縮環ピラゾール誘導体

2012
- 2012-01-30 DK DK12739424.5T patent/DK2669270T3/en active
- 2012-01-30 JP JP2012554878A patent/JP5990106B2/ja not_active Expired - Fee Related
- 2012-01-30 EP EP12739424.5A patent/EP2669270B1/en not_active Not-in-force
- 2012-01-30 WO PCT/JP2012/052009 patent/WO2012102405A1/ja not_active Ceased
- 2012-01-30 US US13/982,200 patent/US8987473B2/en not_active Expired - Fee Related
2015
- 2015-02-11 US US14/619,980 patent/US9359350B2/en not_active Expired - Fee Related
2016
- 2016-08-12 JP JP2016158397A patent/JP6223514B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP5990106B2 (ja)	2016-09-07
JP2017008079A (ja)	2017-01-12
US20140005221A1 (en)	2014-01-02
US9359350B2 (en)	2016-06-07
JP6223514B2 (ja)	2017-11-01
EP2669270A1 (en)	2013-12-04
WO2012102405A1 (ja)	2012-08-02
US8987473B2 (en)	2015-03-24
EP2669270B1 (en)	2018-01-03
US20150203490A1 (en)	2015-07-23
EP2669270A4 (en)	2014-07-02
JPWO2012102405A1 (ja)	2014-07-03

Publication	Publication Date	Title
DK2669270T3 (en)	2018-02-26	Indole-related compounds such as URAT1 inhibitors
US4880804A (en)	1989-11-14	Angiotensin II receptor blocking benzimidazoles
EP1828143B1 (en)	2013-03-20	2-(phenyl or heterocyclic)-1h-phenantrho[9,10-d]imidazoles as mpges-1 inhibitors
DK2380881T3 (en)	2017-05-08	NEW BICYCLIC HETEROCYCLIC COMPOUND
KR100903531B1 (ko)	2009-06-23	티오벤즈이미다졸 유도체
DK2878594T3 (en)	2019-02-04	DIFLUOROMETHYLENE COMPOUND
TW200914449A (en)	2009-04-01	Organic compounds
CN103709154B (zh)	2016-06-15	苯并咪唑衍生物及其制备方法和医药用途
EP2669285A1 (en)	2013-12-04	Pyrazolopyridine derivative or pharmacologically acceptable salt thereof
WO2001090078A1 (en)	2001-11-29	Pyrazole derivatives and their use as gastrin and cholecystokin in receptor ligands
HU221010B1 (hu)	2002-07-29	Imidazo-piridin-származékok és az ezeket tartalmazó gyógyászati készítmények, valamint eljárás előállításukra
KR20160100329A (ko)	2016-08-23	지질 합성의 헤테로사이클릭 조절물질 및 이들의 조합물
RU2126401C1 (ru)	1999-02-20	Производные бензимидазола, их таутомеры или их соли и лекарственное средство с антагонистическим в отношении ангиотензина ii действием
SK8962002A3 (en)	2002-11-06	2-(1h-indol-3-yl)-2-oxo-acetamides with antitumor activity
CN107108575B (zh)	2019-07-26	作为抗组胺剂的新型苯并咪唑衍生物
JP3439643B2 (ja)	2003-08-25	ベンゾイミダゾール化合物
SK297692A3 (en)	1995-09-13	Imidazolylpropene acid substituted derivatives
WO2008015196A1 (en)	2008-02-07	5-,7-bis-substituted imidazo[1,2-a]pyridines
CZ220793A3 (en)	1994-05-18	Imidazopyridines, process of their preparation and pharmaceutical preparations in which they are comprised
JPH0649038A (ja)	1994-02-22	置換ベンゾイミダゾリル誘導体、これらの化合物を含む医薬組成物及びそれらの調製法
DK2781508T3 (en)	2019-03-11	NITROGEN CONCENTRATED RING COMPOUNDS FOR USE AS CRTH2 ANTAGONISTS
WO2003078419A1 (fr)	2003-09-25	Derive du benzothiophenesulfonamide substitue en n
KR100191898B1 (ko)	1999-06-15	벤조푸란계 치환기를 갖는 피리딜 이미다졸 유도체, 그의 제조방법 및 그를 함유하는 혈압강하제
GB2310376A (en)	1997-08-27	Tetrahydropyridine derivatives as dopamine receptor subtype ligands
JPH04257564A (ja)	1992-09-11	縮合イミダゾール誘導体、その製造方法及びそれを含有する循環器官用剤