CA2618586A1 - Nouveau 1,2,3-t.pi.azolylmethyle-benzothiophene substitues ou -indole et leur utilisation en tant qu'inhibiteurs de biosynthese leukot.pi.ene - Google Patents

Nouveau 1,2,3-t.pi.azolylmethyle-benzothiophene substitues ou -indole et leur utilisation en tant qu'inhibiteurs de biosynthese leukot.pi.ene Download PDF

Info

Publication number: CA2618586A1
Authority: CA; Canada
Prior art keywords: compound; group; 6alkyl; substituted; phenyl
Prior art date: 2005-08-11
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

CA002618586A

Other languages

English (en)

Inventor

Carl Berthelette

Claude Dufresne

Lianhai Li

Zhaoyin Wang

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.)

Merck Canada Inc

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.)

2005-08-11

Filing date

2006-08-08

Publication date

2007-02-15

2006-08-08 Application filed by Individual filed Critical Individual

2007-02-15 Publication of CA2618586A1 publication Critical patent/CA2618586A1/fr

Status Abandoned legal-status Critical Current

Links

230000015572 biosynthetic process Effects 0.000 title claims abstract description 33
150000002617 leukotrienes Chemical class 0.000 title claims description 29
239000003112 inhibitor Substances 0.000 title abstract description 30
OPAAUNGTUYYIEV-UHFFFAOYSA-N 4-(1-benzothiophen-2-ylmethyl)-2H-triazole Chemical class N1N=NC(=C1)CC=1SC2=C(C=1)C=CC=C2 OPAAUNGTUYYIEV-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 224
238000011282 treatment Methods 0.000 claims description 53
238000000034 method Methods 0.000 claims description 44
125000001153 fluoro group Chemical group F* 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
-1 (i) -F Chemical class 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
201000010099 disease Diseases 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
201000001320 Atherosclerosis Diseases 0.000 claims description 23
208000006673 asthma Diseases 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 17
230000003143 atherosclerotic effect Effects 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
239000012453 solvate Substances 0.000 claims description 14
125000001309 chloro group Chemical group Cl* 0.000 claims description 13
241000282414 Homo sapiens Species 0.000 claims description 10
238000003786 synthesis reaction Methods 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
201000010105 allergic rhinitis Diseases 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
208000024891 symptom Diseases 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
206010039085 Rhinitis allergic Diseases 0.000 claims description 5
230000009471 action Effects 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
230000004968 inflammatory condition Effects 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
238000011321 prophylaxis Methods 0.000 claims description 5
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 14
230000001120 cytoprotective effect Effects 0.000 abstract description 9
239000000924 antiasthmatic agent Substances 0.000 abstract description 6
230000003266 anti-allergic effect Effects 0.000 abstract description 5
230000001088 anti-asthma Effects 0.000 abstract description 5
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 5
230000002757 inflammatory effect Effects 0.000 abstract description 3
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 248
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 108
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
239000000203 mixture Substances 0.000 description 89
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 70
229910052757 nitrogen Inorganic materials 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
235000019439 ethyl acetate Nutrition 0.000 description 39
238000001704 evaporation Methods 0.000 description 36
230000008020 evaporation Effects 0.000 description 36
239000012044 organic layer Substances 0.000 description 36
238000005481 NMR spectroscopy Methods 0.000 description 35
239000012298 atmosphere Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 35
229910001868 water Inorganic materials 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 29
229910052740 iodine Inorganic materials 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
239000012267 brine Substances 0.000 description 23
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 20
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 19
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 19
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000007832 Na2SO4 Substances 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000013543 active substance Substances 0.000 description 14
239000008346 aqueous phase Substances 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 10
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
238000003556 assay Methods 0.000 description 10
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
150000004702 methyl esters Chemical class 0.000 description 10
208000037260 Atherosclerotic Plaque Diseases 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000003110 anti-inflammatory effect Effects 0.000 description 9
238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 9
239000000843 powder Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
229940125369 inhaled corticosteroids Drugs 0.000 description 8
239000003826 tablet Substances 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
239000002253 acid Substances 0.000 description 7
150000001540 azides Chemical class 0.000 description 7
239000002775 capsule Substances 0.000 description 7
208000029078 coronary artery disease Diseases 0.000 description 7
230000006378 damage Effects 0.000 description 7
239000007788 liquid Substances 0.000 description 7
150000003852 triazoles Chemical class 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 6
101000620009 Homo sapiens Polyunsaturated fatty acid 5-lipoxygenase Proteins 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
239000000556 agonist Substances 0.000 description 6
239000000730 antalgic agent Substances 0.000 description 6
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
230000003902 lesion Effects 0.000 description 6
239000003446 ligand Substances 0.000 description 6
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
GRDZDJKDTAVDCQ-UHFFFAOYSA-N 3-(trifluoromethyl)pent-1-yn-3-ol Chemical compound CCC(O)(C#C)C(F)(F)F GRDZDJKDTAVDCQ-UHFFFAOYSA-N 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000002835 absorbance Methods 0.000 description 5
229960001138 acetylsalicylic acid Drugs 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000000202 analgesic effect Effects 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
230000037396 body weight Effects 0.000 description 5
230000031709 bromination Effects 0.000 description 5
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000010949 copper Substances 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229960000905 indomethacin Drugs 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 5
DYXRPCJFAUISEU-UHFFFAOYSA-N methyl 3-phenyl-6-[[4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)triazol-1-yl]methyl]-1-benzothiophene-2-carboxylate Chemical compound N1=NC(C(O)(CC)C(F)(F)F)=CN1CC1=CC=C(C(=C(S2)C(=O)OC)C=3C=CC=CC=3)C2=C1 DYXRPCJFAUISEU-UHFFFAOYSA-N 0.000 description 5
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
150000005599 propionic acid derivatives Chemical class 0.000 description 5
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 5
IDOVNPILCUGJLW-UHFFFAOYSA-N 3-(3-fluorophenyl)-6-[[4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)triazol-1-yl]methyl]-1-benzothiophene-2-carbonitrile Chemical compound N1=NC(C(O)(CC)C(F)(F)F)=CN1CC1=CC=C(C(=C(S2)C#N)C=3C=C(F)C=CC=3)C2=C1 IDOVNPILCUGJLW-UHFFFAOYSA-N 0.000 description 4
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
150000001242 acetic acid derivatives Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 4
229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 4
229940114079 arachidonic acid Drugs 0.000 description 4
235000021342 arachidonic acid Nutrition 0.000 description 4
125000001743 benzylic group Chemical group 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
229910000024 caesium carbonate Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000002648 combination therapy Methods 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
230000002255 enzymatic effect Effects 0.000 description 4
ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 4
230000002265 prevention Effects 0.000 description 4
LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
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238000010561 standard procedure Methods 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000011550 stock solution Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
VHUHEHFTHOOWND-UHFFFAOYSA-N 1,1,1-trifluoro-2-[1-[[2-(hydroxymethyl)-3-phenyl-1-benzothiophen-6-yl]methyl]triazol-4-yl]butan-2-ol Chemical compound N1=NC(C(O)(CC)C(F)(F)F)=CN1CC1=CC=C(C(=C(CO)S2)C=3C=CC=CC=3)C2=C1 VHUHEHFTHOOWND-UHFFFAOYSA-N 0.000 description 3
LODIXKDJLMMIHE-UHFFFAOYSA-N 1-phenyl-5-[[4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)triazol-1-yl]methyl]indole-2-carboxamide Chemical compound N1=NC(C(O)(CC)C(F)(F)F)=CN1CC1=CC=C(N(C(=C2)C(N)=O)C=3C=CC=CC=3)C2=C1 LODIXKDJLMMIHE-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
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150000001467 thiazolidinediones Chemical class 0.000 description 1
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HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 description 1
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GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
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125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
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239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000019158 vitamin B6 Nutrition 0.000 description 1
239000011726 vitamin B6 Substances 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
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239000011709 vitamin E Substances 0.000 description 1
229940045999 vitamin b 12 Drugs 0.000 description 1
229940009349 vytorin Drugs 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
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238000002424 x-ray crystallography Methods 0.000 description 1
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MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
229940072168 zocor Drugs 0.000 description 1
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1

Classifications

- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- 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
- 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
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

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

CA002618586A 2005-08-11 2006-08-08 Nouveau 1,2,3-t.pi.azolylmethyle-benzothiophene substitues ou -indole et leur utilisation en tant qu'inhibiteurs de biosynthese leukot.pi.ene Abandoned CA2618586A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US70736205P	2005-08-11	2005-08-11
US60/707,362		2005-08-11
PCT/CA2006/001306 WO2007016784A1 (fr)	2005-08-11	2006-08-08	Nouveau 1,2,3-tπazolylméthyle-benzothiophène substitués ou -indole et leur utilisation en tant qu’inhibiteurs de biosynthèse leukotπène

Publications (1)

Publication Number	Publication Date
CA2618586A1 true CA2618586A1 (fr)	2007-02-15

Family

ID=37727061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002618586A Abandoned CA2618586A1 (fr)	2005-08-11	2006-08-08	Nouveau 1,2,3-t.pi.azolylmethyle-benzothiophene substitues ou -indole et leur utilisation en tant qu'inhibiteurs de biosynthese leukot.pi.ene

Country Status (5)

Country	Link
EP (1)	EP1915369A4 (fr)
JP (1)	JP2009504575A (fr)
AU (1)	AU2006279211A1 (fr)
CA (1)	CA2618586A1 (fr)
WO (1)	WO2007016784A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR065093A1 (es)	2007-02-05	2009-05-13	Merck Frosst Canada Ltd	Compuestos farmacéuticos inhibidores de la biosintesis de leucotrienos
US8592402B2 (en)	2009-08-04	2013-11-26	Amira Pharmaceuticals, Inc.	Compounds as lysophosphatidic acid receptor antagonists
GB2474120B (en)	2009-10-01	2011-12-21	Amira Pharmaceuticals Inc	Compounds as Lysophosphatidic acid receptor antagonists
JP6030567B2 (ja)	2010-12-07	2016-11-24	アミラファーマシューティカルス，インコーポレーテッド	多環式ｌｐａ１アンタゴニストおよびその使用
JP2014508111A (ja)	2010-12-07	2014-04-03	アミラファーマシューティカルス，インコーポレーテッド	リゾフォスファチジン酸受容体アンタゴニスト、その線維症の治療における使用
US8541587B2 (en)	2011-04-05	2013-09-24	Amira Pharmaceuticals, Inc.	Lysophosphatidic acid receptor antagonists
WO2012166415A1 (fr)	2011-05-27	2012-12-06	Amira Pharmaceuticals, Inc.	Inhibiteurs hétérocycliques d'autotaxine et leurs utilisations
JP6697809B2 (ja)	2015-03-06	2020-05-27	ファーマケア，インク．	フッ素化リシルオキシダーゼ様２阻害剤とその使用
EP3509594A4 (fr)	2016-09-07	2020-05-06	Pharmakea, Inc.	Utilisations d'un inhibiteur d'homologue 2 de lysyl-oxydase
EA201990621A1 (ru)	2016-09-07	2019-09-30	Фармакеа, Инк.	Кристаллические формы ингибитора лизилоксидаза-подобного белка 2 и способы получения

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SK278998B6 (sk) *	1991-02-01	1998-05-06	Merck Sharp & Dohme Limited	Deriváty imidazolu, triazolu a tetrazolu, spôsob i
CN1802372B (zh) *	2003-06-11	2010-05-12	麦克弗罗斯特加拿大有限公司	7＇-(1,3-噻唑-2-基)-硫代香豆素及其作为白三烯生物合成抑制剂的应用

2006
- 2006-08-08 WO PCT/CA2006/001306 patent/WO2007016784A1/fr active Application Filing
- 2006-08-08 EP EP06775086A patent/EP1915369A4/fr not_active Withdrawn
- 2006-08-08 CA CA002618586A patent/CA2618586A1/fr not_active Abandoned
- 2006-08-08 JP JP2008525348A patent/JP2009504575A/ja not_active Withdrawn
- 2006-08-08 AU AU2006279211A patent/AU2006279211A1/en not_active Abandoned

Also Published As

Publication number	Publication date
JP2009504575A (ja)	2009-02-05
WO2007016784A1 (fr)	2007-02-15
AU2006279211A1 (en)	2007-02-15
EP1915369A4 (fr)	2010-09-08
EP1915369A1 (fr)	2008-04-30

Publication	Publication Date	Title
US7960409B2 (en)	2011-06-14	Pharmaceutical phenylquinoline and chromen-2-one triazole compounds
CA2600727C (fr)	2011-06-14	Derives de coumarine substituee par un thiadiazole et leur utilisation en tant qu'inhibiteur de biosynthese de leucotriene
CA2618586A1 (fr)	2007-02-15	Nouveau 1,2,3-t.pi.azolylmethyle-benzothiophene substitues ou -indole et leur utilisation en tant qu'inhibiteurs de biosynthese leukot.pi.ene
US20100137371A1 (en)	2010-06-03	Novel Pharmaceutical Compounds
US5527827A (en)	1996-06-18	Bisarylcarbinol cinnamic acids as inhibitors of leukotriene biosynthesis
US20090054483A1 (en)	2009-02-26	Substituted Quinolines as Inhibitors of Leukotriene Biosynthesis

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