CA2244189A1 - Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them - Google Patents

Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them Download PDF

Info

Publication number: CA2244189A1
Authority: CA; Canada
Prior art keywords: substituted; compound; salt; carboxy; formula
Prior art date: 1996-01-22
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

Application number

CA002244189A

Other languages

English (en)

French (fr)

Inventor

Masaaki Matsuo

Kazuo Okumura

Shinji Shigenaga

Hiroaki Nishimura

Hiroshi Matsuda

Daijiro Hagiwara

Tadashi Terasaka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Individual

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.)

1996-01-22

Filing date

1997-01-17

Publication date

1997-07-31

1996-01-22 Priority claimed from GBGB9601235.6A external-priority patent/GB9601235D0/en

1996-07-18 Priority claimed from AUPO1111A external-priority patent/AUPO111196A0/en

1997-01-17 Application filed by Individual filed Critical Individual

1997-07-31 Publication of CA2244189A1 publication Critical patent/CA2244189A1/en

Status Abandoned legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
IQDNFLQNJPENQU-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1,3-thiazole Chemical class C1=CSC(C=2OC3=CC=CC=C3C=2)=N1 IQDNFLQNJPENQU-UHFFFAOYSA-N 0.000 title abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 179
-1 carboxy, carboxy Chemical group 0.000 claims abstract description 165
125000003118 aryl group Chemical group 0.000 claims abstract description 123
125000001424 substituent group Chemical group 0.000 claims abstract description 98
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 94
125000003545 alkoxy group Chemical group 0.000 claims abstract description 93
125000000217 alkyl group Chemical group 0.000 claims abstract description 79
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
125000002947 alkylene group Chemical group 0.000 claims abstract description 22
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 17
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 13
150000001875 compounds Chemical class 0.000 claims description 278
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 158
238000006243 chemical reaction Methods 0.000 claims description 117
238000000034 method Methods 0.000 claims description 58
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 36
125000002252 acyl group Chemical group 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
125000003831 tetrazolyl group Chemical group 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
241000282414 Homo sapiens Species 0.000 claims description 5
206010020751 Hypersensitivity Diseases 0.000 claims description 5
206010061218 Inflammation Diseases 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
208000026935 allergic disease Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
238000007257 deesterification reaction Methods 0.000 claims description 5
230000004054 inflammatory process Effects 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
238000006114 decarboxylation reaction Methods 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
238000006264 debenzylation reaction Methods 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 6
238000004519 manufacturing process Methods 0.000 claims 2
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
230000022244 formylation Effects 0.000 claims 1
238000006170 formylation reaction Methods 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000005557 antagonist Substances 0.000 abstract description 4
230000000694 effects Effects 0.000 abstract description 4
239000003112 inhibitor Substances 0.000 abstract description 4
150000002617 leukotrienes Chemical class 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 378
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 359
239000000203 mixture Substances 0.000 description 254
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 216
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 160
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 142
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 130
229940093499 ethyl acetate Drugs 0.000 description 126
235000019439 ethyl acetate Nutrition 0.000 description 126
239000000243 solution Substances 0.000 description 115
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
101150041968 CDC13 gene Proteins 0.000 description 105
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 98
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 91
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
239000012267 brine Substances 0.000 description 66
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 66
229910052943 magnesium sulfate Inorganic materials 0.000 description 65
235000019341 magnesium sulphate Nutrition 0.000 description 65
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 63
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
239000000741 silica gel Substances 0.000 description 57
229910002027 silica gel Inorganic materials 0.000 description 57
239000002904 solvent Substances 0.000 description 54
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
238000001816 cooling Methods 0.000 description 48
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 47
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
239000012044 organic layer Substances 0.000 description 45
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
238000004440 column chromatography Methods 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
238000001914 filtration Methods 0.000 description 32
238000002360 preparation method Methods 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
239000002244 precipitate Substances 0.000 description 28
238000010992 reflux Methods 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
239000012046 mixed solvent Substances 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 25
239000002253 acid Substances 0.000 description 23
229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
235000017557 sodium bicarbonate Nutrition 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
230000002411 adverse Effects 0.000 description 21
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
239000006188 syrup Substances 0.000 description 20
235000020357 syrup Nutrition 0.000 description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
239000000706 filtrate Substances 0.000 description 19
239000005457 ice water Substances 0.000 description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
238000006722 reduction reaction Methods 0.000 description 18
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
239000003960 organic solvent Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
238000010792 warming Methods 0.000 description 14
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 13
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
239000003638 chemical reducing agent Substances 0.000 description 12
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 11
238000000921 elemental analysis Methods 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
235000011181 potassium carbonates Nutrition 0.000 description 11
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
238000010531 catalytic reduction reaction Methods 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 8
125000005605 benzo group Chemical group 0.000 description 8
239000012043 crude product Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 7
JBOPQACSHPPKEP-UHFFFAOYSA-N indoxyl acetate Natural products C1=CC=C2C(OC(=O)C)=CNC2=C1 JBOPQACSHPPKEP-UHFFFAOYSA-N 0.000 description 7
229910052697 platinum Inorganic materials 0.000 description 7
239000008096 xylene Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
229910017052 cobalt Inorganic materials 0.000 description 6
239000010941 cobalt Substances 0.000 description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
239000010949 copper Substances 0.000 description 6
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
150000002148 esters Chemical group 0.000 description 6
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
150000007522 mineralic acids Chemical class 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
239000000725 suspension Substances 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000007529 inorganic bases Chemical class 0.000 description 5
229910052742 iron Inorganic materials 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
239000012528 membrane Substances 0.000 description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
239000003921 oil Substances 0.000 description 5
125000004430 oxygen atom Chemical group O* 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
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 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
201000004624 Dermatitis Diseases 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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239000013058 crude material Substances 0.000 description 1
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125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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235000018417 cysteine Nutrition 0.000 description 1
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CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
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RPQVRRSJUIEITQ-UHFFFAOYSA-N ethyl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]-2-methylindole-3-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OCC)=C(C)N1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 RPQVRRSJUIEITQ-UHFFFAOYSA-N 0.000 description 1
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HGGFMFWUNVGYKR-UHFFFAOYSA-N ethyl 2-[2-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]oxymethyl]-6-methoxyphenoxy]propanoate Chemical compound C1=CC=C(OC)C(OC(C)C(=O)OCC)=C1COC1=CC=C(OC(=C2)C=3SC=C(N=3)C(C)(C)C)C2=C1 HGGFMFWUNVGYKR-UHFFFAOYSA-N 0.000 description 1
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CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
238000002826 magnetic-activated cell sorting Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
MFSPVADDZAXXLU-UHFFFAOYSA-N methyl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]-3-cyanoindole-5-carboxylate Chemical compound C1=C(C#N)C2=CC(C(=O)OC)=CC=C2N1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 MFSPVADDZAXXLU-UHFFFAOYSA-N 0.000 description 1
UCLJDTWKSBYIOR-UHFFFAOYSA-N methyl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]-5-methoxyindazole-3-carboxylate Chemical compound C12=CC=C(OC)C=C2C(C(=O)OC)=NN1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 UCLJDTWKSBYIOR-UHFFFAOYSA-N 0.000 description 1
YUXHQQLBRWTOJV-UHFFFAOYSA-N methyl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]indole-2-carboxylate Chemical compound COC(=O)C1=CC2=CC=CC=C2N1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 YUXHQQLBRWTOJV-UHFFFAOYSA-N 0.000 description 1
UEOIKZLXTKGJLU-UHFFFAOYSA-N methyl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]indole-3-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=CN1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 UEOIKZLXTKGJLU-UHFFFAOYSA-N 0.000 description 1
NQPIEWBAWBFGOB-UHFFFAOYSA-N methyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=C1 NQPIEWBAWBFGOB-UHFFFAOYSA-N 0.000 description 1
AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 1
YGTCKAXXVMBMPP-UHFFFAOYSA-N methyl 2-[5-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]indol-3-yl]acetate Chemical compound C12=CC=C(OCC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C=C2C(CC(=O)OC)=CN1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 YGTCKAXXVMBMPP-UHFFFAOYSA-N 0.000 description 1
PAFUKZMNTQWTPL-UHFFFAOYSA-N methyl 3-cyano-1h-indole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC=C(C#N)C2=C1 PAFUKZMNTQWTPL-UHFFFAOYSA-N 0.000 description 1
KJRFTNVYOAGTHK-UHFFFAOYSA-N methyl 3-hydroxy-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CO KJRFTNVYOAGTHK-UHFFFAOYSA-N 0.000 description 1
XDAUKQXMIHVKGQ-UHFFFAOYSA-N methyl 5-propan-2-yl-1h-indazole-3-carboxylate Chemical compound C1=C(C(C)C)C=C2C(C(=O)OC)=NNC2=C1 XDAUKQXMIHVKGQ-UHFFFAOYSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
XFSSDIWLZFNNKI-UHFFFAOYSA-N n'-(4-propan-2-ylphenyl)acetohydrazide Chemical compound CC(C)C1=CC=C(NNC(C)=O)C=C1 XFSSDIWLZFNNKI-UHFFFAOYSA-N 0.000 description 1
RRNLVICCUZTJOW-UHFFFAOYSA-N n'-hydroxypentanimidamide Chemical compound CCCCC(N)=NO RRNLVICCUZTJOW-UHFFFAOYSA-N 0.000 description 1
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
HLEKYJVHEBHTMR-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O.CCCCC(N)=O HLEKYJVHEBHTMR-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-M phenoxyacetate Chemical compound [O-]C(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-M 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
235000011056 potassium acetate Nutrition 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
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
NWUIWGFIBIRQOK-UHFFFAOYSA-N propan-2-yl 1-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]methyl]-5-phenylmethoxyindazole-3-carboxylate Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)OC(C)C)=NN1CC(C=C1C=2)=CC=C1OC=2C1=NC(C(C)(C)C)=CS1 NWUIWGFIBIRQOK-UHFFFAOYSA-N 0.000 description 1
AVJJCZQJRONPKS-UHFFFAOYSA-N propan-2-yl 5-phenylmethoxy-1h-indazole-3-carboxylate Chemical compound C1=C2C(C(=O)OC(C)C)=NNC2=CC=C1OCC1=CC=CC=C1 AVJJCZQJRONPKS-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
201000006845 reticulosarcoma Diseases 0.000 description 1
208000029922 reticulum cell sarcoma Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
VNMKPQLKEAYMKV-UHFFFAOYSA-M sodium;2-[2-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]oxymethyl]-6-methoxyphenoxy]propanoate Chemical compound [Na+].COC1=CC=CC(COC=2C=C3C=C(OC3=CC=2)C=2SC=C(N=2)C(C)(C)C)=C1OC(C)C([O-])=O VNMKPQLKEAYMKV-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
PQBSMJYDCMUYSU-UHFFFAOYSA-N tert-butyl 2-[3-formyl-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenoxy]acetate Chemical compound CC(C)(C)OC(=O)COC1=CC=C(OCC(=O)OC(C)(C)C)C(C=O)=C1 PQBSMJYDCMUYSU-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002244189A 1996-01-22 1997-01-17 Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them Abandoned CA2244189A1 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB9601235.6		1996-01-22
GBGB9601235.6A GB9601235D0 (en)	1996-01-22	1996-01-22	Novel compounds
AUPO1111A AUPO111196A0 (en)	1996-07-18	1996-07-18	Novel compounds
AUPO1111		1996-07-18

Publications (1)

Publication Number	Publication Date
CA2244189A1 true CA2244189A1 (en)	1997-07-31

Family

ID=25645218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002244189A Abandoned CA2244189A1 (en)	1996-01-22	1997-01-17	Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them

Country Status (12)

Country	Link
US (1)	US5994378A (2)
EP (2)	EP0880519B1 (2)
JP (1)	JP2000503984A (2)
KR (1)	KR19990076788A (2)
CN (1)	CN1209809A (2)
AT (2)	ATE263561T1 (2)
CA (1)	CA2244189A1 (2)
DE (2)	DE69712042T2 (2)
EA (1)	EA199800650A1 (2)
ES (1)	ES2171878T3 (2)
HU (1)	HUP9900424A2 (2)
WO (1)	WO1997027190A1 (2)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9919413D0 (en)	1999-08-18	1999-10-20	Zeneca Ltd	Chemical compounds
WO2001032621A1 (en) *	1999-10-29	2001-05-10	Wakunaga Pharmaceutical Co., Ltd.	Novel indole derivatives and drugs containing the same as the active ingredient
CN100540538C (zh) *	2001-04-16	2009-09-16	田边三菱制药株式会社	高传导率钙-活化k通道开启剂
AU2002323776B2 (en)	2001-08-10	2008-07-31	Nippon Chemiphar Co., Ltd.	Activator for peroxisome proliferator-responsive receptor Delta
JP4276074B2 (ja)	2001-10-12	2009-06-10	日本ケミファ株式会社	ペルオキシソーム増殖剤応答性受容体δの活性化剤
EP1771169A1 (en) *	2004-07-14	2007-04-11	PTC Therapeutics, Inc.	Methods for treating hepatitis c
KR20070091607A (ko) *	2004-10-12	2007-09-11	디코드 제네틱스, 아이엔씨.	폐쇄성 동맥 질환용의 설폰아미드 주변 치환된바이사이클릭 화합물
WO2006046683A1 (en) *	2004-10-25	2006-05-04	Astellas Pharma Inc.	Thiazolylbenzofuran derivatives as leukotriene and prostaglandin d2 receptor antagonists
US7977359B2 (en)	2005-11-04	2011-07-12	Amira Pharmaceuticals, Inc.	5-lipdxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en)	2005-11-04	2013-03-19	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors
GB2431927B (en) *	2005-11-04	2010-03-17	Amira Pharmaceuticals Inc	5-Lipoxygenase-activating protein (FLAP) inhibitors
CA2642668C (en) *	2006-02-15	2013-01-08	Allergan, Inc.	Indole-3-carboxylic acid amide and ester compounds bearing phenyl groups having sphingosine-1-phosphate (s1p) receptor antagonist biological activity
CN101460458A (zh) *	2006-02-15	2009-06-17	阿勒根公司	具有1－磷酸－鞘氨醇(s1p)受体拮抗剂生物活性的带芳基或者杂芳基基团的吲哚－3－羧酸的酰胺、酯、硫代酰胺和硫羟酸酯化合物
ZA200809148B (en)	2006-04-18	2010-01-27	Nippon Chemiphar Co	Activating agent for peroxisome proliferator activated receptor delta
DE102006021733A1 (de) *	2006-05-09	2007-11-22	Bayer Healthcare Ag	3-Tetrazolylindazole und 3-Tetrazolylpyrazolopyridine sowie ihre Verwendung
EP2027117A2 (en) *	2006-05-16	2009-02-25	Decode Genetics EHF	Process for preparing 7-(acryloyl)-indoles
DE102006043443A1 (de) *	2006-09-15	2008-03-27	Bayer Healthcare Ag	Neue aza-bicyclische Verbindungen und ihre Verwendung
US8524917B2 (en)	2007-01-11	2013-09-03	Allergan, Inc.	6-substituted indole-3-carboxylic acid amide compounds having sphingosine-1-phosphate (S1P) receptor antagonist biological activity
JP2010515750A (ja) *	2007-01-11	2010-05-13	アラーガンインコーポレイテッド	スフィンゴシン−１−ホスフェート（ｓ１ｐ）受容体アンタゴニスト生物活性を有する６−置換インドール−３−カルボン酸アミド化合物
JP5474769B2 (ja)	2008-04-15	2014-04-16	日本ケミファ株式会社	ペルオキシソーム増殖剤活性化受容体の活性化剤
US8546431B2 (en)	2008-10-01	2013-10-01	Panmira Pharmaceuticals, Llc	5-lipoxygenase-activating protein (FLAP) inhibitors
DE102008063992A1 (de)	2008-12-19	2010-09-02	Lerner, Zinoviy, Dipl.-Ing.	Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung
NZ601967A (en)	2010-03-12	2015-03-27	Omeros Corp	Pde10 inhibitors and related compositions and methods
CN106986862A (zh)	2010-12-22	2017-07-28	Abbvie 公司	丙型肝炎抑制剂及其用途
AP2015008670A0 (en)	2013-02-21	2015-08-31	Adverio Pharma Gmbh	Forms of methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-B]pyridino-3-yl]pyrimidino-5-yl} methyl carbamate
NZ716462A (en)	2014-04-28	2017-11-24	Omeros Corp	Optically active pde10 inhibitor
NZ716494A (en)	2014-04-28	2017-07-28	Omeros Corp	Processes and intermediates for the preparation of a pde10 inhibitor
KR102586736B1 (ko) *	2014-08-29	2023-10-11	씨에이치디아이 파운데이션, 인코포레이티드	헌팅틴을 단백질 영상화하기 위한 프로브
CN107530313A (zh)	2015-04-24	2018-01-02	奥默罗斯公司	Pde10抑制剂以及相关组合物和方法
WO2017079678A1 (en)	2015-11-04	2017-05-11	Omeros Corporation	Solid state forms of a pde10 inhibitor
AU2018367909B2 (en)	2017-11-17	2022-03-10	Cellix Bio Private Limited	Compositions and methods for the treatment of eye disorders

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2600644B2 (ja) *	1991-08-16	1997-04-16	藤沢薬品工業株式会社	チアゾリルベンゾフラン誘導体
JPH07179856A (ja) *	1993-12-21	1995-07-18	Canon Inc	液晶性化合物、これを含有する液晶組成物、該液晶組成物を用いた液晶素子並びにこれらを用いた表示方法、表示装置

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- 1997-01-17 JP JP9526720A patent/JP2000503984A/ja not_active Ceased
- 1997-01-17 CA CA002244189A patent/CA2244189A1/en not_active Abandoned
- 1997-01-17 AT AT01123263T patent/ATE263561T1/de not_active IP Right Cessation
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- 1997-01-17 WO PCT/JP1997/000073 patent/WO1997027190A1/en not_active Ceased
- 1997-01-17 HU HU9900424A patent/HUP9900424A2/hu unknown
- 1997-01-17 DE DE69712042T patent/DE69712042T2/de not_active Expired - Fee Related
- 1997-01-17 EP EP97900432A patent/EP0880519B1/en not_active Expired - Lifetime
- 1997-01-17 US US09/101,766 patent/US5994378A/en not_active Expired - Fee Related
- 1997-01-17 KR KR1019980704913A patent/KR19990076788A/ko not_active Ceased
- 1997-01-17 DE DE69728581T patent/DE69728581D1/de not_active Expired - Lifetime
- 1997-01-17 ES ES97900432T patent/ES2171878T3/es not_active Expired - Lifetime
- 1997-01-17 EP EP01123263A patent/EP1170009B1/en not_active Expired - Lifetime
- 1997-01-17 EA EA199800650A patent/EA199800650A1/ru unknown
- 1997-01-17 CN CN97191798A patent/CN1209809A/zh active Pending

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Publication number	Publication date
WO1997027190A1 (en)	1997-07-31
EA199800650A1 (ru)	1999-02-25
JP2000503984A (ja)	2000-04-04
ES2171878T3 (es)	2002-09-16
DE69712042T2 (de)	2002-10-02
ATE263561T1 (de)	2004-04-15
KR19990076788A (ko)	1999-10-15
US5994378A (en)	1999-11-30
EP0880519A1 (en)	1998-12-02
EP1170009A2 (en)	2002-01-09
DE69728581D1 (de)	2004-05-13
ATE216384T1 (de)	2002-05-15
EP1170009A3 (en)	2002-01-16
HUP9900424A2 (hu)	1999-05-28
CN1209809A (zh)	1999-03-03
DE69712042D1 (de)	2002-05-23
EP1170009B1 (en)	2004-04-07
EP0880519B1 (en)	2002-04-17

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Date	Code	Title	Description
2002-01-14	EEER	Examination request
2006-01-17	FZDE	Discontinued

Publication	Publication Date	Title
US5994378A (en)	1999-11-30	Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them
US5296495A (en)	1994-03-22	Thiazolylbenzofuran derivatives and pharmaceutical composition comprising the same
AU690620B2 (en)	1998-04-30	Platelet activating factor antagonists: imidazopyridine indoles
ES2293906T3 (es)	2008-04-01	Compuestos de indazol y composiciones farmaceuticas para inhibir proteinas quinasas, y metodos para su uso.
US6069156A (en)	2000-05-30	Indole derivatives as cGMP-PDE inhibitors
US5661159A (en)	1997-08-26	Quinolylbenzofuran derivatives as leukotriene antagonists
JP3119485B2 (ja)	2000-12-18	抗−エイズ薬としての置換インドール類
US20040077877A1 (en)	2004-04-22	Indazole derivatives as JNK inhibitors and compositions and methods related thereto
JPH10130147A (ja)	1998-05-19	異項環置換アシルアミノチアゾールを含む医薬組成物
KR20010031896A (ko)	2001-04-16	시클린 의존성 키나아제의 아미노티아졸 억제제
RS52396B (sr)	2013-02-28	Derivati aminoindazola, postupak izrade i međuproizvodi ovog postupak kao medicinski produkti i farmaceutske kompozicije koje ih sadrže
JP2005527463A (ja)	2005-09-15	Ｃｎｓ疾患を治療するための５−ｈｔ６受容体アフィニティーを有する３−アリールスルホニル−７−ピペラジニル−インドール、−ベンゾフランおよび−ベンゾチオフェン
JPH08507067A (ja)	1996-07-30	Ｈｉｖ逆転写酵素阻害剤
WO2001032621A1 (en)	2001-05-10	Novel indole derivatives and drugs containing the same as the active ingredient
EP0303418A2 (en)	1989-02-15	Substituted indolones, useful in the treatment of heart or asthmatic diseases
JPH11508267A (ja)	1999-07-21	ピラゾール化合物および医薬組成物
HUT70158A (en)	1995-09-28	Process for producing 2-amido-4-phenyl-thiazol derivatives, and pharmaceutical compositions containing them
CN101010297B (zh)	2011-07-27	N-(1h-吲哚基)-1h-吲哚-2-羧酰胺衍生物，它们的制备方法和药用用途
JP2001526287A (ja)	2001-12-18	新たな薬学的に活性な化合物
JPH09509957A (ja)	1997-10-07	免疫調節剤としてのキノリン誘導体
CA2109498A1 (en)	1994-04-29	Benzylidene derivatives
JPH08119936A (ja)	1996-05-14	複素環式誘導体
JP3012338B2 (ja)	2000-02-21	アリールおよびヘテロアリールアルコキシナフタレン誘導体
MX2007016541A (es)	2008-03-07	Compuestos quimicos.
AU1399197A (en)	1997-08-20	Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them