UA82888C2 - Benzimidazole, benzthiazole and benzoxazole derivatives and their use as lta4h modulators - Google Patents

Info

Publication number

UA82888C2

UA82888C2 UAA200601432A UAA200601432A UA82888C2 UA 82888 C2 UA82888 C2 UA 82888C2 UA A200601432 A UAA200601432 A UA A200601432A UA A200601432 A UAA200601432 A UA A200601432A UA 82888 C2 UA82888 C2 UA 82888C2

Authority

UA

Ukraine

Prior art keywords

yloxy

benzothiazol

benzyl

piperidin

group

Prior art date

2003-07-28

Links

• Espacenet
• Global Dossier
• Discuss

• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 13
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 2
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
• 206010061218 Inflammation Diseases 0.000 claims abstract description 30
• 230000004054 inflammatory process Effects 0.000 claims abstract description 30
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
• 230000000694 effects Effects 0.000 claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims description 502
• 238000000034 method Methods 0.000 claims description 383
• -1 1,3- dihydroindol-2-one-1-yl Chemical group 0.000 claims description 304
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 268
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 259
• 229910052757 nitrogen Inorganic materials 0.000 claims description 154
• 229910052799 carbon Inorganic materials 0.000 claims description 143
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 141
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 130
• 125000001424 substituent group Chemical group 0.000 claims description 106
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 95
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 76
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 64
• 229920006395 saturated elastomer Polymers 0.000 claims description 50
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 49
• 150000001408 amides Chemical class 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 239000002253 acid Substances 0.000 claims description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 230000015572 biosynthetic process Effects 0.000 claims description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims description 38
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 29
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
• 125000004193 piperazinyl group Chemical group 0.000 claims description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 125000003386 piperidinyl group Chemical group 0.000 claims description 20
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 17
• 102000004190 Enzymes Human genes 0.000 claims description 17
• 108090000790 Enzymes Proteins 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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• 230000001404 mediated effect Effects 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims description 14
• 239000004202 carbamide Substances 0.000 claims description 13
• 229940047889 isobutyramide Drugs 0.000 claims description 13
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• 208000006673 asthma Diseases 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 12
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 11
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
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• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
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• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
• HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 150000004677 hydrates Chemical class 0.000 claims description 9
• NSQMWZLLTGEDQU-UHFFFAOYSA-N 2-aminocyclobutane-1-carboxylic acid Chemical compound NC1CCC1C(O)=O NSQMWZLLTGEDQU-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 150000002170 ethers Chemical class 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 201000006417 multiple sclerosis Diseases 0.000 claims description 8
• 210000002700 urine Anatomy 0.000 claims description 8
• 229910052727 yttrium Inorganic materials 0.000 claims description 8
• ZMQJXJKADGZNSO-UHFFFAOYSA-N 2-[4-(piperazin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCNCC1 ZMQJXJKADGZNSO-UHFFFAOYSA-N 0.000 claims description 7
• 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 description 7
• 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 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 229930195733 hydrocarbon Natural products 0.000 claims description 7
• 150000002430 hydrocarbons Chemical class 0.000 claims description 7
• 229940080818 propionamide Drugs 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
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 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
• 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 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
• 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 description 6
• LXFBZMAHNZSEJG-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CN1CCOCC1 LXFBZMAHNZSEJG-UHFFFAOYSA-N 0.000 claims description 6
• 239000004215 Carbon black (E152) Substances 0.000 claims description 6
• 125000003368 amide group Chemical group 0.000 claims description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 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 6
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 229910052770 Uranium Inorganic materials 0.000 claims description 5
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
• 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
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• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
• 230000002757 inflammatory effect Effects 0.000 claims description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 10
• 229940057054 1,3-dimethylurea Drugs 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
• MMPJZYXYNRYMQR-UHFFFAOYSA-N 4-chloro-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1OC(C=C1)=CC=C1CN1CCCCC1 MMPJZYXYNRYMQR-UHFFFAOYSA-N 0.000 claims 5
• 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 5
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 5
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• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 5
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• 210000005056 cell body Anatomy 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
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