ZA200601720B - Benzimidazole, benzithiazole and benzoxazole derivatives and their use as LTA4H modulators - Google Patents
Benzimidazole, benzithiazole and benzoxazole derivatives and their use as LTA4H modulators Download PDFInfo
- Publication number
- ZA200601720B ZA200601720B ZA200601720A ZA200601720A ZA200601720B ZA 200601720 B ZA200601720 B ZA 200601720B ZA 200601720 A ZA200601720 A ZA 200601720A ZA 200601720 A ZA200601720 A ZA 200601720A ZA 200601720 B ZA200601720 B ZA 200601720B
- Authority
- ZA
- South Africa
- Prior art keywords
- yloxy
- benzyl
- piperidin
- benzothiazol
- group
- Prior art date
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- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 title claims description 48
- 101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 title claims 34
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 256
- 229910052757 nitrogen Inorganic materials 0.000 claims description 153
- -1 heteroaryl-Cisalkyl Chemical group 0.000 claims description 151
- 229910052799 carbon Inorganic materials 0.000 claims description 115
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 114
- 125000005842 heteroatom Chemical group 0.000 claims description 108
- 125000001424 substituent group Chemical group 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000623 heterocyclic group Chemical group 0.000 claims description 72
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 206010061218 Inflammation Diseases 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 230000004054 inflammatory process Effects 0.000 claims description 33
- 150000002148 esters Chemical class 0.000 claims description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
- 125000004193 piperazinyl group Chemical group 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 150000001408 amides Chemical class 0.000 claims description 21
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
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- 238000006467 substitution reaction Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
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- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 201000004681 Psoriasis Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 208000019693 Lung disease Diseases 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 5
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 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 4
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 4
- 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 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
- 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 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 17
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 17
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 7
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims 6
- BUZBVOKDNAZIIM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BUZBVOKDNAZIIM-UHFFFAOYSA-N 0.000 claims 5
- PLMQGVLYXRYVOO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1h-benzimidazole Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 PLMQGVLYXRYVOO-UHFFFAOYSA-N 0.000 claims 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 5
- 229940047889 isobutyramide Drugs 0.000 claims 5
- 239000003973 paint Substances 0.000 claims 5
- HRGRBUXTSLZJHT-UHFFFAOYSA-N 2-[2-fluoro-4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C(F)=CC=1CN1CCCCC1 HRGRBUXTSLZJHT-UHFFFAOYSA-N 0.000 claims 4
- ZVDOMASQJBYMSO-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 ZVDOMASQJBYMSO-UHFFFAOYSA-N 0.000 claims 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 4
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- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims 4
- 229940080818 propionamide Drugs 0.000 claims 4
- 229940057054 1,3-dimethylurea Drugs 0.000 claims 3
- NUFHDURBLSHZNX-UHFFFAOYSA-N 1-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NUFHDURBLSHZNX-UHFFFAOYSA-N 0.000 claims 3
- BTYHUCROUVOSFY-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BTYHUCROUVOSFY-UHFFFAOYSA-N 0.000 claims 3
- IDRGIXMWFWVVIO-UHFFFAOYSA-N 1-[[4-(1h-benzimidazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 IDRGIXMWFWVVIO-UHFFFAOYSA-N 0.000 claims 3
- JNKRNJIZLGLIJG-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCCCC1 JNKRNJIZLGLIJG-UHFFFAOYSA-N 0.000 claims 3
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims 3
- PBYPGZHIAKLYFN-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-3-carboxylic acid Chemical compound C1CN(C(=O)O)CCC11CCNCC1 PBYPGZHIAKLYFN-UHFFFAOYSA-N 0.000 claims 3
- HTXWCJZXGZUXPD-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HTXWCJZXGZUXPD-UHFFFAOYSA-N 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
- 125000004494 ethyl ester group Chemical group 0.000 claims 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 3
- YTSLVJQQFDKVOS-UHFFFAOYSA-N n-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]propane-1-sulfonamide Chemical compound C1CC(NS(=O)(=O)CCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YTSLVJQQFDKVOS-UHFFFAOYSA-N 0.000 claims 3
- CREOVZBMIBKVON-UHFFFAOYSA-N 1-[2-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]ethyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CREOVZBMIBKVON-UHFFFAOYSA-N 0.000 claims 2
- HFWIFRRHMZLJNF-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HFWIFRRHMZLJNF-UHFFFAOYSA-N 0.000 claims 2
- ZSLLLGHNYUBQPU-UHFFFAOYSA-N 1-[3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-cyclopropylamino]propyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCCN(C1CC1)CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 ZSLLLGHNYUBQPU-UHFFFAOYSA-N 0.000 claims 2
- RVBPILVVAOIPAV-UHFFFAOYSA-N 1-[4-(1,3-benzothiazol-2-yloxy)phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1OC1=NC2=CC=CC=C2S1 RVBPILVVAOIPAV-UHFFFAOYSA-N 0.000 claims 2
- CFTXJKKITUELKJ-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CFTXJKKITUELKJ-UHFFFAOYSA-N 0.000 claims 2
- JWKXNNWNYXKUNZ-UHFFFAOYSA-N 2-[2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-2-oxoethyl]cyclopentan-1-one Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)CC1CCCC1=O JWKXNNWNYXKUNZ-UHFFFAOYSA-N 0.000 claims 2
- WNCUSFCVRSUOKM-UHFFFAOYSA-N 2-[2-fluoro-4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C(F)=CC=1CN1CCCCC1 WNCUSFCVRSUOKM-UHFFFAOYSA-N 0.000 claims 2
- AVRWIZZEDUWJDM-UHFFFAOYSA-N 2-[4-[(4,4-difluoropiperidin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CC(F)(F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AVRWIZZEDUWJDM-UHFFFAOYSA-N 0.000 claims 2
- KUMUDRZJCKKLNV-UHFFFAOYSA-N 2-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN(CC1)CCC1C1=NN=NN1 KUMUDRZJCKKLNV-UHFFFAOYSA-N 0.000 claims 2
- WHQQJWGYHZAHDC-UHFFFAOYSA-N 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propanenitrile Chemical compound C1=CC(CN(CCC#N)C)=CC=C1OC1=NC2=CC=CC=C2S1 WHQQJWGYHZAHDC-UHFFFAOYSA-N 0.000 claims 2
- QQNNAAFXXJNLGN-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QQNNAAFXXJNLGN-UHFFFAOYSA-N 0.000 claims 2
- VSIGIJUYXPEPFK-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-2-one Chemical compound C1CNC(=O)CN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VSIGIJUYXPEPFK-UHFFFAOYSA-N 0.000 claims 2
- IQTFFIWZQWGCCE-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IQTFFIWZQWGCCE-UHFFFAOYSA-N 0.000 claims 2
- XEWLYIXTOJAJNS-UHFFFAOYSA-N 4-methyl-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound N=1C=2C(C)=CC=CC=2SC=1OC(C=C1)=CC=C1CN1CCCCC1 XEWLYIXTOJAJNS-UHFFFAOYSA-N 0.000 claims 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 2
- BLYKQHVKEFOYPK-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]carbamic acid Chemical compound C1CC(NC(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BLYKQHVKEFOYPK-UHFFFAOYSA-N 0.000 claims 2
- NOSINBBPECBLQO-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]thiourea Chemical compound C1CC(NC(=S)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOSINBBPECBLQO-UHFFFAOYSA-N 0.000 claims 2
- GACNDIIZOZQWCU-UHFFFAOYSA-N [2-[[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]amino]-2-oxoethyl] acetate Chemical compound C1CC(NC(=O)COC(=O)C)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GACNDIIZOZQWCU-UHFFFAOYSA-N 0.000 claims 2
- JDVOEZLVRSILGD-UHFFFAOYSA-N [4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-(oxolan-2-yl)methanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCCO1 JDVOEZLVRSILGD-UHFFFAOYSA-N 0.000 claims 2
- JTXYCSAJSQUDSP-UHFFFAOYSA-N [4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]-thiophen-2-ylmethanone Chemical compound C1CN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=CS1 JTXYCSAJSQUDSP-UHFFFAOYSA-N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- BLZWKGRUUCYVQX-UHFFFAOYSA-N ethyl 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BLZWKGRUUCYVQX-UHFFFAOYSA-N 0.000 claims 2
- IDONXSDVZAPFLV-UHFFFAOYSA-N ethyl 2-[4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 IDONXSDVZAPFLV-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- AEVHVVDLIHWAGR-UHFFFAOYSA-N methyl 2-amino-2-oxoacetate Chemical compound COC(=O)C(N)=O AEVHVVDLIHWAGR-UHFFFAOYSA-N 0.000 claims 2
- HCZICZIPHKCVQY-UHFFFAOYSA-N n'-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]-n'-methylpropane-1,3-diamine Chemical compound C1=CC(CN(CCCN)C)=CC=C1OC1=NC2=CC=CC=C2S1 HCZICZIPHKCVQY-UHFFFAOYSA-N 0.000 claims 2
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- 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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- A—HUMAN NECESSITIES
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- 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
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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AU2006286573B2 (en) * | 2005-09-02 | 2012-05-31 | F. Hoffmann-La Roche Ag | Benzooxazole, oxazolopyridine, benzothiazole and thiazolopyridine derivatives |
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US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
WO2008019284A1 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of lta4h for treating inflammation |
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CN101969951B (zh) * | 2007-11-16 | 2012-10-31 | 雅培制药有限公司 | 化合物在制备治疗关节炎的药物中的方法 |
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GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
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JP5746685B2 (ja) | 2009-05-14 | 2015-07-08 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプJanssen Pharmaceutica Naamloze Vennootschap | ロイコトリエンa4加水分解酵素のモジュレーターとしての縮合二環式ヘテロアリール部分を2つ有する化合物 |
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AU2014249168B2 (en) | 2013-03-12 | 2018-07-12 | Celltaxis, Llc | Methods of inhibiting leukotriene A4 hydrolase |
BR112015022864A8 (pt) | 2013-03-14 | 2019-11-26 | Celtaxsys Inc | composto, composição farmacêutica e uso dos mesmos |
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EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
JP6549735B2 (ja) | 2015-06-09 | 2019-07-24 | アッヴィ・インコーポレイテッド | 核内受容体調節剤 |
EP3559249A1 (en) | 2016-12-21 | 2019-10-30 | H. Hoffnabb-La Roche Ag | Method for in vitro glycoengineering of antibodies |
CN107663192B (zh) * | 2017-11-03 | 2019-05-10 | 梯尔希(南京)药物研发有限公司 | 一种雷贝拉唑杂质的制备方法 |
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CN110026557B (zh) * | 2019-05-28 | 2021-08-27 | 南方科技大学 | 一种混合固体颗粒重熔的直写装置及成型方法 |
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- 2004-07-27 CN CNA2004800279067A patent/CN1856490A/zh active Pending
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