ZA200601716B - Benzimidazole, benzthiazole and benzoxazole derivatives and their use as LTA4H, modulators - Google Patents
Benzimidazole, benzthiazole and benzoxazole derivatives and their use as LTA4H, modulators Download PDFInfo
- Publication number
- ZA200601716B ZA200601716B ZA200601716A ZA200601716A ZA200601716B ZA 200601716 B ZA200601716 B ZA 200601716B ZA 200601716 A ZA200601716 A ZA 200601716A ZA 200601716 A ZA200601716 A ZA 200601716A ZA 200601716 B ZA200601716 B ZA 200601716B
- Authority
- ZA
- South Africa
- Prior art keywords
- ethyl
- yloxy
- benzothiazol
- piperidin
- phenoxy
- Prior art date
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- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 title claims description 91
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 45
- 101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 title claims 73
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 368
- 229910052757 nitrogen Inorganic materials 0.000 claims description 240
- -1 Benzothiazol-2-yloxy Chemical group 0.000 claims description 232
- 125000005842 heteroatom Chemical group 0.000 claims description 163
- 125000000623 heterocyclic group Chemical group 0.000 claims description 155
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 145
- 229910052799 carbon Inorganic materials 0.000 claims description 145
- 238000000034 method Methods 0.000 claims description 143
- 150000001875 compounds Chemical class 0.000 claims description 142
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 142
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 100
- 125000001424 substituent group Chemical group 0.000 claims description 98
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 65
- 235000019260 propionic acid Nutrition 0.000 claims description 51
- 150000002148 esters Chemical class 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 47
- 206010061218 Inflammation Diseases 0.000 claims description 44
- 230000004054 inflammatory process Effects 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 38
- 150000001408 amides Chemical class 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 28
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
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- 208000006673 asthma Diseases 0.000 claims description 22
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 22
- 230000001404 mediated effect Effects 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 21
- 238000006467 substitution reaction Methods 0.000 claims description 21
- 208000019693 Lung disease Diseases 0.000 claims description 19
- 201000006417 multiple sclerosis Diseases 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 13
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- JFYFFICGEIKUMA-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 JFYFFICGEIKUMA-UHFFFAOYSA-N 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 6
- GCSDZVIXDKZKFO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzoxazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2O1 GCSDZVIXDKZKFO-UHFFFAOYSA-N 0.000 claims description 6
- HGLXZYVILQDPRO-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1h-benzimidazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2N1 HGLXZYVILQDPRO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 229940080818 propionamide Drugs 0.000 claims description 6
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- IQTADKJWOJRVNV-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzothiazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2S1 IQTADKJWOJRVNV-UHFFFAOYSA-N 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 229960004063 propylene glycol Drugs 0.000 claims description 5
- 235000013772 propylene glycol Nutrition 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- KWCUTOWTFFAFGD-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-n-propan-2-ylsulfonylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NS(=O)(=O)C(C)C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 KWCUTOWTFFAFGD-UHFFFAOYSA-N 0.000 claims description 4
- MOQCNLBYCQEEOO-UHFFFAOYSA-N 2-[4-[2-(4-benzylpiperidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCC1CC1=CC=CC=C1 MOQCNLBYCQEEOO-UHFFFAOYSA-N 0.000 claims description 4
- FHNXSUARUMPPBX-UHFFFAOYSA-N 2-[4-[2-(4-methylpiperidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C1CC(C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 FHNXSUARUMPPBX-UHFFFAOYSA-N 0.000 claims description 4
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- QFDISQIDKZUABE-UHFFFAOYSA-N 1,1'-bipiperidine Chemical compound C1CCCCN1N1CCCCC1 QFDISQIDKZUABE-UHFFFAOYSA-N 0.000 claims description 3
- QEEKSUQXDWTJIW-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QEEKSUQXDWTJIW-UHFFFAOYSA-N 0.000 claims description 3
- FDTVVMYDEDPLPY-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 FDTVVMYDEDPLPY-UHFFFAOYSA-N 0.000 claims description 3
- PDTIFQAUDNZZIV-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-yloxy)phenoxy]propyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 PDTIFQAUDNZZIV-UHFFFAOYSA-N 0.000 claims description 3
- GLTMBLQAEJWHDD-UHFFFAOYSA-N 1-[4-(1,3-benzoxazol-2-yloxy)phenoxy]-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCC(O)CN1CCCC1 GLTMBLQAEJWHDD-UHFFFAOYSA-N 0.000 claims description 3
- KSTQAHVAEMPYHX-UHFFFAOYSA-N 2-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl-propylamino]ethanol Chemical compound C1=CC(OCCN(CCO)CCC)=CC=C1OC1=NC2=CC=CC=C2O1 KSTQAHVAEMPYHX-UHFFFAOYSA-N 0.000 claims description 3
- MJLBZFXLDHOOMN-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethoxy)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCCC1 MJLBZFXLDHOOMN-UHFFFAOYSA-N 0.000 claims description 3
- SSQAGYBYJTZVJM-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 SSQAGYBYJTZVJM-UHFFFAOYSA-N 0.000 claims description 3
- JYGZPGXROUXHGB-UHFFFAOYSA-N 2-[4-[2-(azetidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCC1 JYGZPGXROUXHGB-UHFFFAOYSA-N 0.000 claims description 3
- QUBMVPYHQPAMID-UHFFFAOYSA-N 2-[4-[2-(tetrazol-2-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1N=CN=N1 QUBMVPYHQPAMID-UHFFFAOYSA-N 0.000 claims description 3
- FYPBSNZDJJJSKL-UHFFFAOYSA-N 2-[4-[2-[4-(2h-tetrazol-5-yl)piperidin-1-yl]ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCC1C1=NN=NN1 FYPBSNZDJJJSKL-UHFFFAOYSA-N 0.000 claims description 3
- OOPWCKHMMFFPRZ-UHFFFAOYSA-N 3-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl-benzylamino]propanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CCC(=O)O)CC1=CC=CC=C1 OOPWCKHMMFFPRZ-UHFFFAOYSA-N 0.000 claims description 3
- IKCVCAQFEIOACD-UHFFFAOYSA-N 4-[2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]ethyl]morpholine Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CCN1CCOCC1 IKCVCAQFEIOACD-UHFFFAOYSA-N 0.000 claims description 3
- BIZVFRGJJTYCDX-UHFFFAOYSA-N ethyl 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C1CCC(=O)N1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BIZVFRGJJTYCDX-UHFFFAOYSA-N 0.000 claims description 3
- FDSUAPKEGWZEFY-UHFFFAOYSA-N ethyl 2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]tetrazol-5-yl]acetate Chemical compound CCOC(=O)CC1=NN=NN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FDSUAPKEGWZEFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 3
- GWSZYUJFYKFDPN-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GWSZYUJFYKFDPN-UHFFFAOYSA-N 0.000 claims description 3
- GOGSXZRAYQAMOD-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CC)C1CCCCC1 GOGSXZRAYQAMOD-UHFFFAOYSA-N 0.000 claims description 3
- PGNCKSDHQSASSK-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCNC1CC1 PGNCKSDHQSASSK-UHFFFAOYSA-N 0.000 claims description 3
- AREHXWXMLHRGGI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Br)C=C1 AREHXWXMLHRGGI-UHFFFAOYSA-N 0.000 claims description 2
- FQIDMNGIAGRBQM-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 FQIDMNGIAGRBQM-UHFFFAOYSA-N 0.000 claims description 2
- NVSWCWWHQRVUDU-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethoxy)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCOCC1 NVSWCWWHQRVUDU-UHFFFAOYSA-N 0.000 claims description 2
- DDPDHHQNYWOFTO-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCCC1 DDPDHHQNYWOFTO-UHFFFAOYSA-N 0.000 claims description 2
- ICDQXKCQGHKKOJ-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 ICDQXKCQGHKKOJ-UHFFFAOYSA-N 0.000 claims description 2
- KPAQPCYFUAKHTL-UHFFFAOYSA-N 2-[4-(3-piperidin-1-ylpropyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCCN1CCCCC1 KPAQPCYFUAKHTL-UHFFFAOYSA-N 0.000 claims description 2
- DEHCLLRTXGGKRC-UHFFFAOYSA-N 2-[4-(3-pyrrolidin-1-ylpropoxy)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCCN1CCCC1 DEHCLLRTXGGKRC-UHFFFAOYSA-N 0.000 claims description 2
- DSEBKYYZHMQLQD-UHFFFAOYSA-N 2-[4-[2-(4,4-difluoropiperidin-1-yl)ethyl]phenoxy]-1,3-benzothiazole Chemical compound C1CC(F)(F)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 DSEBKYYZHMQLQD-UHFFFAOYSA-N 0.000 claims description 2
- QCSXJTVRWQJEOO-UHFFFAOYSA-N 2-[4-[2-(4-ethylsulfonylpiperazin-1-yl)ethyl]phenoxy]-1,3-benzothiazole Chemical compound C1CN(S(=O)(=O)CC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QCSXJTVRWQJEOO-UHFFFAOYSA-N 0.000 claims description 2
- SGYGJMWFYCKRCR-UHFFFAOYSA-N 2-[4-[2-(5-methylsulfanyltetrazol-1-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound CSC1=NN=NN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 SGYGJMWFYCKRCR-UHFFFAOYSA-N 0.000 claims description 2
- ZTKIUJKOFNKGOK-UHFFFAOYSA-N 2-[4-[2-(5-phenyltetrazol-2-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(N=1)N=NC=1C1=CC=CC=C1 ZTKIUJKOFNKGOK-UHFFFAOYSA-N 0.000 claims description 2
- LVHDUIHFVYXWAA-UHFFFAOYSA-N 2-[4-[2-(tetrazol-1-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1C=NN=N1 LVHDUIHFVYXWAA-UHFFFAOYSA-N 0.000 claims description 2
- GNJMLSXLJRCEOU-UHFFFAOYSA-N 2-[4-[2-[4-(1-benzyltetrazol-5-yl)piperidin-1-yl]ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCC1C1=NN=NN1CC1=CC=CC=C1 GNJMLSXLJRCEOU-UHFFFAOYSA-N 0.000 claims description 2
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- LZNRDTOYJHNQND-UHFFFAOYSA-N 3-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl-(1-methylpiperidin-4-yl)amino]propanoic acid Chemical compound C1CN(C)CCC1N(CCC(O)=O)CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LZNRDTOYJHNQND-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- 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
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Public Health (AREA)
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- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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US (2) | US20050043379A1 (no) |
EP (2) | EP1660491B1 (no) |
JP (2) | JP2007500703A (no) |
KR (2) | KR101149379B1 (no) |
CN (2) | CN100591679C (no) |
AR (2) | AR045729A1 (no) |
AT (2) | ATE403654T1 (no) |
AU (2) | AU2004261628B2 (no) |
BR (2) | BRPI0412345A (no) |
CA (2) | CA2534228A1 (no) |
CY (1) | CY1108560T1 (no) |
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DK (2) | DK1660492T3 (no) |
ES (2) | ES2313079T3 (no) |
HK (2) | HK1092790A1 (no) |
HR (2) | HRP20060039A2 (no) |
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MY (1) | MY145080A (no) |
NO (2) | NO20060771L (no) |
NZ (2) | NZ544970A (no) |
PL (2) | PL1660492T3 (no) |
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RU (2) | RU2359970C2 (no) |
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SI (2) | SI1660492T1 (no) |
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AU2004261628B2 (en) * | 2003-07-28 | 2011-05-12 | Janssen Pharmaceutica N.V. | Benzimidazole, benzthiazole and benzoxazole derivatives and their use as LTA4H modulators |
MX2007012235A (es) * | 2005-03-31 | 2008-03-18 | Johnson & Johnson | Moduladores de leucotrieno a4 hidrolasa de fenilo y piridilo. |
WO2006109085A1 (en) | 2005-04-13 | 2006-10-19 | Astex Therapeutics Limited | Hydroxybenzamide derivatives and their use as inhibitors of hsp90 |
EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
ES2359431T3 (es) * | 2005-09-02 | 2011-05-23 | F. Hoffmann-La Roche Ag | Derivados de benzooxazol, oxazolopiridina, benzotiazol y tiazolopiridina. |
KR101328306B1 (ko) * | 2005-09-21 | 2013-11-11 | 디코드 제네틱스 이에이치에프 | 염증 치료를 위한 lta4h의 바이아릴 치환된헤테로사이클 억제제 |
CA2634699A1 (en) | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of lta4h for treating inflammation |
AU2006327245A1 (en) | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | Biaryl substituted nitrogen containing heterocycle inhibitors of LTA4H for treating inflammation |
US7750012B2 (en) * | 2005-12-21 | 2010-07-06 | Decode Genetics Ehf | Biaryl nitrogen-heterocycle inhibitors of LTA4H for treating inflammation |
DK1976828T3 (en) * | 2005-12-29 | 2017-03-06 | Celtaxsys Inc | DIAMINE DERIVATIVES AS INhibitors of Leukotriene A4 HYDROLASE |
WO2007085357A1 (en) * | 2006-01-30 | 2007-08-02 | Euro-Celtique S.A. | Cyclourea compounds as calcium channel blockers |
US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
US7951829B2 (en) * | 2006-05-03 | 2011-05-31 | Janssen Pharmaceutica Nv | Benzimidazole modulators of VR1 |
AU2007260356B2 (en) * | 2006-06-16 | 2013-01-24 | H. Lundbeck A/S | Crystalline forms of 4- [2- (4-methylphenylsulfanyl) -phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
US7728032B2 (en) * | 2006-08-04 | 2010-06-01 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of LTA4H for treating inflammation |
EP2066800A2 (en) | 2006-08-04 | 2009-06-10 | Decode Genetics EHF | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
WO2008044029A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
CL2008000468A1 (es) * | 2007-02-14 | 2008-08-22 | Janssen Pharmaceutica Nv | Uso de compuestos derivados de heterociclos, inhibidores de leucotrina a4 hidrolasa (lta4h), utiles para tratar o prevenir la dermatitis, acne, infarto al miocardio, dolor, picazon, gingivitis, cancer, artritis, entre otras. |
EP2134704B1 (en) * | 2007-03-08 | 2010-09-22 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
US20100100012A1 (en) * | 2007-03-30 | 2010-04-22 | Yoshihiro Matsumura | Activity intensity measurement device |
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EP2231159A1 (en) * | 2007-11-16 | 2010-09-29 | Abbott Laboratories | Method of treating arthritis |
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PL2294066T3 (pl) | 2008-04-28 | 2015-02-27 | Janssen Pharmaceutica Nv | Benzimidazole jako inhibitory hydroksylazy prolilowej |
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CN102442962A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-烷基四氮唑的生产方法 |
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