SI20115A - Spojine in sestavki za zdravljenje bolezni, povezanih z aktivnostjo serinskih proteaz, zlasti triptaze - Google Patents

Info

Publication number

SI20115A

SI20115A SI9720094A SI9720094A SI20115A SI 20115 A SI20115 A SI 20115A SI 9720094 A SI9720094 A SI 9720094A SI 9720094 A SI9720094 A SI 9720094A SI 20115 A SI20115 A SI 20115A

Authority

SI

Slovenia

Prior art keywords

benzoimidazol

ethyl

compound

alkyl

methyl

Prior art date

1997-04-07

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 374
• 239000000203 mixture Substances 0.000 title claims abstract description 151
• 108060005989 Tryptase Proteins 0.000 title abstract description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 28
• 201000010099 disease Diseases 0.000 title description 26
• 102000001400 Tryptase Human genes 0.000 title description 23
• 230000000694 effects Effects 0.000 title description 8
• 102000012479 Serine Proteases Human genes 0.000 title description 3
• 108010022999 Serine Proteases Proteins 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 42
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 238000002360 preparation method Methods 0.000 claims abstract description 12
• 210000002345 respiratory system Anatomy 0.000 claims abstract description 5
• 230000000699 topical effect Effects 0.000 claims abstract description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
• 206010010741 Conjunctivitis Diseases 0.000 claims abstract description 3
• -1 amino, carboxy, carbamoyl Chemical group 0.000 claims description 338
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 192
• 125000000217 alkyl group Chemical group 0.000 claims description 102
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 88
• 125000005842 heteroatom Chemical group 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 125000006413 ring segment Chemical group 0.000 claims description 32
• 239000005711 Benzoic acid Substances 0.000 claims description 31
• 235000010233 benzoic acid Nutrition 0.000 claims description 31
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 30
• 239000000651 prodrug Substances 0.000 claims description 27
• 229940002612 prodrug Drugs 0.000 claims description 27
• 125000002947 alkylene group Chemical group 0.000 claims description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000001931 aliphatic group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000002723 alicyclic group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 16
• 125000004423 acyloxy group Chemical group 0.000 claims description 14
• SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
• OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000003943 azolyl group Chemical group 0.000 claims description 11
• 150000002431 hydrogen Chemical group 0.000 claims description 11
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 239000000443 aerosol Substances 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
• FNLQDVXHDNFXIY-UHFFFAOYSA-N 3h-benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=NC2=C1 FNLQDVXHDNFXIY-UHFFFAOYSA-N 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 230000009385 viral infection Effects 0.000 claims description 6
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
• 125000001118 alkylidene group Chemical group 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• FEPAORUNILXIKL-UHFFFAOYSA-N C(CC)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 Chemical compound C(CC)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 FEPAORUNILXIKL-UHFFFAOYSA-N 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 239000000843 powder Substances 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• FTNBVAOKBGAXCR-UHFFFAOYSA-N 2-[2-[[2-[1-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3-(2-methoxyethyl)benzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound C1=C2N(CCOC)C(C(C)C=3NC=4CCN(CC=4N=3)C(C)=N)=NC2=CC=C1C(=O)NCCOC1=CC=CC=C1C(O)=O FTNBVAOKBGAXCR-UHFFFAOYSA-N 0.000 claims description 3
• MTWFINXLTMNGCU-UHFFFAOYSA-N 2-[2-[[3-methyl-2-[1-(4,6,7-trifluoro-1h-benzimidazol-2-yl)ethyl]benzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=C(F)C=C(F)C(F)=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(O)=O MTWFINXLTMNGCU-UHFFFAOYSA-N 0.000 claims description 3
• PCCUPAKWDDHPKB-UHFFFAOYSA-N 5-chloro-2-[2-[[2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=C(Cl)C=C1C(O)=O PCCUPAKWDDHPKB-UHFFFAOYSA-N 0.000 claims description 3
• 239000000808 adrenergic beta-agonist Substances 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
• GIHLYBBKNGKPHR-UHFFFAOYSA-N 2-[(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)methyl]-n-(2-hydroxy-2-naphthalen-1-ylethyl)-3-methylbenzimidazole-5-carboxamide Chemical compound C1=CC=C2C(C(O)CNC(=O)C3=CC=C4N=C(N(C4=C3)C)CC=3NC=4CCN(CC=4N=3)C(=N)C)=CC=CC2=C1 GIHLYBBKNGKPHR-UHFFFAOYSA-N 0.000 claims description 2
• SYWNNHDBRIRLIJ-UHFFFAOYSA-N 2-[2-[[2-[1-(5-ethanimidoyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3-methylbenzimidazole-5-carbonyl]amino]ethoxy]benzoic acid Chemical compound N=1C=2CN(C(C)=N)CCC=2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(O)=O SYWNNHDBRIRLIJ-UHFFFAOYSA-N 0.000 claims description 2
• OLZJYKTXRMALAB-UHFFFAOYSA-N C(C)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 Chemical compound C(C)C=1NC2=C(N1)C=CC(=C2)C(=O)NCCC2=CC=CC1=CC=CC=C21 OLZJYKTXRMALAB-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 150000001204 N-oxides Chemical class 0.000 claims description 2
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 2
• 229960001022 fenoterol Drugs 0.000 claims description 2
• LSLYOANBFKQKPT-UHFFFAOYSA-N fenoterol Chemical compound C=1C(O)=CC(O)=CC=1C(O)CNC(C)CC1=CC=C(O)C=C1 LSLYOANBFKQKPT-UHFFFAOYSA-N 0.000 claims description 2
• 229960002848 formoterol Drugs 0.000 claims description 2
• BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 2
• WURDECGZGWCLLG-UHFFFAOYSA-N n-[2-(2-carbamoylphenoxy)ethyl]-2-[1-[6-(diaminomethylideneamino)-1h-benzimidazol-2-yl]ethyl]-3-methylbenzimidazole-5-carboxamide Chemical compound N=1C2=CC(NC(N)=N)=CC=C2NC=1C(C)C(N(C1=C2)C)=NC1=CC=C2C(=O)NCCOC1=CC=CC=C1C(N)=O WURDECGZGWCLLG-UHFFFAOYSA-N 0.000 claims description 2
• 229960002052 salbutamol Drugs 0.000 claims description 2
• 229960000195 terbutaline Drugs 0.000 claims description 2
• 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• 125000004924 2-naphthylethyl group Chemical group C1=C(C=CC2=CC=CC=C12)CC* 0.000 claims 1
• 206010019909 Hernia Diseases 0.000 claims 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
• 125000004104 aryloxy group Chemical group 0.000 claims 1
• 108091022884 dihydropyrimidinase Proteins 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 208000006673 asthma Diseases 0.000 abstract description 27
• 210000003630 histaminocyte Anatomy 0.000 abstract description 13
• 230000002265 prevention Effects 0.000 abstract description 5
• 206010039085 Rhinitis allergic Diseases 0.000 abstract description 4
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• 238000001819 mass spectrum Methods 0.000 description 205
• 229940087827 biolon Drugs 0.000 description 149
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 92
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
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• 239000000243 solution Substances 0.000 description 56
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
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• 239000002244 precipitate Substances 0.000 description 38
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• 238000001914 filtration Methods 0.000 description 23
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• 239000012299 nitrogen atmosphere Substances 0.000 description 18
• 238000005481 NMR spectroscopy Methods 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
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• 241001465754 Metazoa Species 0.000 description 11
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• 239000000427 antigen Substances 0.000 description 7
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• 239000002585 base Substances 0.000 description 7
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
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• 235000011152 sodium sulphate Nutrition 0.000 description 7
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• 230000004047 hyperresponsiveness Effects 0.000 description 6
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• 208000026935 allergic disease Diseases 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
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