JP7410017B2 - 新規なテトラゾール化合物および結核の治療におけるそれらの使用 - Google Patents

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Publication number

JP7410017B2

JP7410017B2 JP2020508427A JP2020508427A JP7410017B2 JP 7410017 B2 JP7410017 B2 JP 7410017B2 JP 2020508427 A JP2020508427 A JP 2020508427A JP 2020508427 A JP2020508427 A JP 2020508427A JP 7410017 B2 JP7410017 B2 JP 7410017B2

Authority

JP

Japan

Prior art keywords

tetrazol

benzenesulfonamide

hydroxyethyl

methyl

mmol

Prior art date

2017-08-17

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.)

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• -1 tetrazole compounds Chemical class 0.000 title claims description 121
• 201000008827 tuberculosis Diseases 0.000 title claims description 43
• 238000011282 treatment Methods 0.000 title claims description 40
• 150000001875 compounds Chemical class 0.000 claims description 169
• 239000000203 mixture Substances 0.000 claims description 91
• 150000003839 salts Chemical class 0.000 claims description 65
• 125000001153 fluoro group Chemical group F* 0.000 claims description 61
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 208000027531 mycobacterial infectious disease Diseases 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 25
• 206010062207 Mycobacterial infection Diseases 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 229940079593 drug Drugs 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 11
• AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 11
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• MINDENKOQXRZKY-UHFFFAOYSA-N N-(2-hydroxyethyl)-4-[2-[(5-methoxypyridin-2-yl)methyl]tetrazol-5-yl]benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=C(C=C1)OC MINDENKOQXRZKY-UHFFFAOYSA-N 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 150000003952 β-lactams Chemical class 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• MWTWVBRUCLGTKZ-UHFFFAOYSA-N C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1OCCCC1 Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1OCCCC1 MWTWVBRUCLGTKZ-UHFFFAOYSA-N 0.000 claims description 5
• ZADGDPAVPJLDBU-UHFFFAOYSA-N FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCCO Chemical compound FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCCO ZADGDPAVPJLDBU-UHFFFAOYSA-N 0.000 claims description 5
• 239000003926 antimycobacterial agent Substances 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• HBUJYEUPIIJJOS-PBHICJAKSA-N (5r)-3-[4-[1-[(2s)-2,3-dihydroxypropanoyl]-3,6-dihydro-2h-pyridin-4-yl]-3,5-difluorophenyl]-5-(1,2-oxazol-3-yloxymethyl)-1,3-oxazolidin-2-one Chemical compound C1N(C(=O)[C@@H](O)CO)CCC(C=2C(=CC(=CC=2F)N2C(O[C@@H](COC3=NOC=C3)C2)=O)F)=C1 HBUJYEUPIIJJOS-PBHICJAKSA-N 0.000 claims description 4
• YVQFTBCCLOPEHL-UHFFFAOYSA-N 2-[[4-[2-(pyridin-4-ylmethyl)tetrazol-5-yl]phenyl]sulfonylamino]acetamide Chemical compound N1=CC=C(C=C1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCC(=O)N YVQFTBCCLOPEHL-UHFFFAOYSA-N 0.000 claims description 4
• AMOTYOFVUWLKOI-UHFFFAOYSA-N 2-fluoro-N-(2-hydroxyethyl)-4-[2-(oxan-2-ylmethyl)tetrazol-5-yl]benzenesulfonamide Chemical compound FC1=C(C=CC(=C1)C=1N=NN(N=1)CC1OCCCC1)S(=O)(=O)NCCO AMOTYOFVUWLKOI-UHFFFAOYSA-N 0.000 claims description 4
• MJNPHLBKHKJDEF-UHFFFAOYSA-N 2h-1$l^{4},2-benzothiazine 1-oxide Chemical compound C1=CC=C2S(=O)NC=CC2=C1 MJNPHLBKHKJDEF-UHFFFAOYSA-N 0.000 claims description 4
• KYZDYKMOJSXPTN-UHFFFAOYSA-N 3-fluoro-4-[2-[(5-fluoropyridin-2-yl)methyl]tetrazol-5-yl]-N-(2-hydroxyethyl)benzenesulfonamide Chemical compound FC=1C=C(C=CC=1C=1N=NN(N=1)CC1=NC=C(C=C1)F)S(=O)(=O)NCCO KYZDYKMOJSXPTN-UHFFFAOYSA-N 0.000 claims description 4
• VMWKDHXOEVMTHN-UHFFFAOYSA-N 4-[2-[(4-fluorophenyl)methyl]tetrazol-5-yl]-N-methylbenzenesulfonamide Chemical compound FC1=CC=C(CN2N=C(N=N2)C2=CC=C(C=C2)S(=O)(=O)NC)C=C1 VMWKDHXOEVMTHN-UHFFFAOYSA-N 0.000 claims description 4
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• OYMPTMAOYQXAGP-UHFFFAOYSA-N C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=C(N=C1)C Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=C(N=C1)C OYMPTMAOYQXAGP-UHFFFAOYSA-N 0.000 claims description 4
• UDQTYDJWLIEAPC-UHFFFAOYSA-N C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=CN=C1 Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=CN=C1 UDQTYDJWLIEAPC-UHFFFAOYSA-N 0.000 claims description 4
• PEUMNWXFNLKOTQ-UHFFFAOYSA-N C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1CCOCC1 Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1CCOCC1 PEUMNWXFNLKOTQ-UHFFFAOYSA-N 0.000 claims description 4
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• DNHBARLXRWKXMG-UHFFFAOYSA-N CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=CC=NC=C1 Chemical compound CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=CC=NC=C1 DNHBARLXRWKXMG-UHFFFAOYSA-N 0.000 claims description 4
• BVCMDHQMUMKUOD-UHFFFAOYSA-N COC1=C(C=CC(=C1)C=1N=NN(N=1)CC1=CC=NC=C1)S(=O)(=O)NC Chemical compound COC1=C(C=CC(=C1)C=1N=NN(N=1)CC1=CC=NC=C1)S(=O)(=O)NC BVCMDHQMUMKUOD-UHFFFAOYSA-N 0.000 claims description 4
• WUIFICKTLNYRRZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1C=1N=NN(N=1)CC1=NC=C(C=C1)F)S(=O)(=O)NCCO Chemical compound ClC=1C=C(C=CC=1C=1N=NN(N=1)CC1=NC=C(C=C1)F)S(=O)(=O)NCCO WUIFICKTLNYRRZ-UHFFFAOYSA-N 0.000 claims description 4
• BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 4
• FSTFRFWIZODANL-UHFFFAOYSA-N FC1=C(C=CC(=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)F)S(=O)(=O)NCCO Chemical compound FC1=C(C=CC(=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)F)S(=O)(=O)NCCO FSTFRFWIZODANL-UHFFFAOYSA-N 0.000 claims description 4
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• VMTAVOKZRSWUIL-UHFFFAOYSA-N FC1=C(C=CC(=C1F)C=1N=NN(N=1)CC1OCCCC1)S(=O)(=O)NCCO Chemical compound FC1=C(C=CC(=C1F)C=1N=NN(N=1)CC1OCCCC1)S(=O)(=O)NCCO VMTAVOKZRSWUIL-UHFFFAOYSA-N 0.000 claims description 4
• KZTYGHVBKKFPKN-UHFFFAOYSA-N FC1=CC=C(CN2N=C(N=N2)C2=CC(=C(C=C2)S(=O)(=O)NCC(=O)N)OC)C=C1 Chemical compound FC1=CC=C(CN2N=C(N=N2)C2=CC(=C(C=C2)S(=O)(=O)NCC(=O)N)OC)C=C1 KZTYGHVBKKFPKN-UHFFFAOYSA-N 0.000 claims description 4
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• XIKPUAQLKWIPAO-UHFFFAOYSA-N FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC(=C(C=C1)S(=O)(=O)NCCO)C Chemical compound FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC(=C(C=C1)S(=O)(=O)NCCO)C XIKPUAQLKWIPAO-UHFFFAOYSA-N 0.000 claims description 4
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• BRFBKYRMHYVMFE-UHFFFAOYSA-N N-(2-hydroxyethyl)-2-methoxy-4-[2-(pyridin-4-ylmethyl)tetrazol-5-yl]benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=C(C=C(C=C1)C=1N=NN(N=1)CC1=CC=NC=C1)OC BRFBKYRMHYVMFE-UHFFFAOYSA-N 0.000 claims description 4
• TZJFMBUGWHCJRZ-UHFFFAOYSA-N N-(2-hydroxyethyl)-4-[2-(pyridazin-4-ylmethyl)tetrazol-5-yl]benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=CN=NC=C1 TZJFMBUGWHCJRZ-UHFFFAOYSA-N 0.000 claims description 4
• ZVHTZXAUQWQAHS-UHFFFAOYSA-N N-(cyanomethyl)-4-[2-[(5-methoxypyrazin-2-yl)methyl]tetrazol-5-yl]benzenesulfonamide Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=C(N=C1)OC ZVHTZXAUQWQAHS-UHFFFAOYSA-N 0.000 claims description 4
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