JP2010235612A5 - - Google Patents
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- Publication number
- JP2010235612A5 JP2010235612A5 JP2010109145A JP2010109145A JP2010235612A5 JP 2010235612 A5 JP2010235612 A5 JP 2010235612A5 JP 2010109145 A JP2010109145 A JP 2010109145A JP 2010109145 A JP2010109145 A JP 2010109145A JP 2010235612 A5 JP2010235612 A5 JP 2010235612A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- arylcarbonylamino
- alkoxy
- pharmaceutically acceptable
- substituted
- Prior art date
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- -1 cyano, amino Chemical group 0.000 claims 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 125000004986 diarylamino group Chemical group 0.000 claims 2
- 229910052736 halogen Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- NKJXMLIWSJATEE-UHFFFAOYSA-N Cc(cc1)ccc1C(NO)=N Chemical compound Cc(cc1)ccc1C(NO)=N NKJXMLIWSJATEE-UHFFFAOYSA-N 0.000 description 8
- 0 *[N+](c(cc1)cc2c1nc(-c1cc(-c3ccccc3)ccc1)[n]2O)[O-] Chemical compound *[N+](c(cc1)cc2c1nc(-c1cc(-c3ccccc3)ccc1)[n]2O)[O-] 0.000 description 7
- CUEKBBQYAWCAFY-UHFFFAOYSA-N Cc(cc1)c(C)cc1[NH+]([O-])O Chemical compound Cc(cc1)c(C)cc1[NH+]([O-])O CUEKBBQYAWCAFY-UHFFFAOYSA-N 0.000 description 7
- GKDIAVWPXOXCBW-UHFFFAOYSA-N Cc(cc1)ccc1C(NO)=C Chemical compound Cc(cc1)ccc1C(NO)=C GKDIAVWPXOXCBW-UHFFFAOYSA-N 0.000 description 2
- UNFAAXQGZJDPCX-UHFFFAOYSA-N NCc(cc1)ccc1C(NO)=N Chemical compound NCc(cc1)ccc1C(NO)=N UNFAAXQGZJDPCX-UHFFFAOYSA-N 0.000 description 2
- OPGWBTKZYLRPRW-UHFFFAOYSA-N Nc1cc(C(NO)=N)ccc1 Chemical compound Nc1cc(C(NO)=N)ccc1 OPGWBTKZYLRPRW-UHFFFAOYSA-N 0.000 description 2
- CPCBKIRIGJHCAX-UHFFFAOYSA-N C/[O]=C(/c1ncccc1)\Nc(cc1)ccc1-c1nc(ccc([N+]([O-])=O)c2)c2[n]1O Chemical compound C/[O]=C(/c1ncccc1)\Nc(cc1)ccc1-c1nc(ccc([N+]([O-])=O)c2)c2[n]1O CPCBKIRIGJHCAX-UHFFFAOYSA-N 0.000 description 1
- RHYIYQDBAQJCPY-UHFFFAOYSA-N CC(C)(C)C(Nc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+]([O-])=O)=O Chemical compound CC(C)(C)C(Nc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+]([O-])=O)=O RHYIYQDBAQJCPY-UHFFFAOYSA-N 0.000 description 1
- LZRKZIPAKYUIHX-UHFFFAOYSA-N CC(C)(C)OC(NCc(cc1)ccc1C(NO)=N)O Chemical compound CC(C)(C)OC(NCc(cc1)ccc1C(NO)=N)O LZRKZIPAKYUIHX-UHFFFAOYSA-N 0.000 description 1
- VIPMBJSGYWWHAO-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1C(N)=O Chemical compound CC(C)(C)c(cc1)ccc1C(N)=O VIPMBJSGYWWHAO-UHFFFAOYSA-N 0.000 description 1
- WZNUDZBRAFIOQX-UHFFFAOYSA-N CC(Nc(cccc1)c1-c1nc(ccc([N+]([O-])=O)c2)c2[n]1O)=O Chemical compound CC(Nc(cccc1)c1-c1nc(ccc([N+]([O-])=O)c2)c2[n]1O)=O WZNUDZBRAFIOQX-UHFFFAOYSA-N 0.000 description 1
- RMGFSSKOGFNSDW-UHFFFAOYSA-O CC(Nc1cc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)ccc1)=O Chemical compound CC(Nc1cc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)ccc1)=O RMGFSSKOGFNSDW-UHFFFAOYSA-O 0.000 description 1
- ZQPVJMLHNCFVNG-UHFFFAOYSA-N CC1(C)C(C)=CC([NH+]([O-])O)=CC1 Chemical compound CC1(C)C(C)=CC([NH+]([O-])O)=CC1 ZQPVJMLHNCFVNG-UHFFFAOYSA-N 0.000 description 1
- VVZYBQHJHUXXPG-UHFFFAOYSA-N CC1(C2=CC([N+](O)=O)=CC1)N=C(c1cc(C(F)(F)F)ccc1)N2O Chemical compound CC1(C2=CC([N+](O)=O)=CC1)N=C(c1cc(C(F)(F)F)ccc1)N2O VVZYBQHJHUXXPG-UHFFFAOYSA-N 0.000 description 1
- RIEAJIVEXCZCIX-UHFFFAOYSA-N CN(C)c(cc1)ccc1-c1nc(ccc([N+](O)=O)c2)c2[n]1O Chemical compound CN(C)c(cc1)ccc1-c1nc(ccc([N+](O)=O)c2)c2[n]1O RIEAJIVEXCZCIX-UHFFFAOYSA-N 0.000 description 1
- GEBBAUHUTGGURH-UHFFFAOYSA-N CN(C)c1cccc(-c([n](c2c3)O)nc2ccc3[N+]2([O-])OC2)c1 Chemical compound CN(C)c1cccc(-c([n](c2c3)O)nc2ccc3[N+]2([O-])OC2)c1 GEBBAUHUTGGURH-UHFFFAOYSA-N 0.000 description 1
- YSKSOUNHUMDIEN-UHFFFAOYSA-N CN(C1c(cccc2)c2OC)c(ccc([N+](O)=O)c2)c2N1O Chemical compound CN(C1c(cccc2)c2OC)c(ccc([N+](O)=O)c2)c2N1O YSKSOUNHUMDIEN-UHFFFAOYSA-N 0.000 description 1
- NZZZOYVRPOWZJQ-UHFFFAOYSA-N CNc1cccc(C(N)=O)c1 Chemical compound CNc1cccc(C(N)=O)c1 NZZZOYVRPOWZJQ-UHFFFAOYSA-N 0.000 description 1
- IQMOCCRAIJWKAG-UHFFFAOYSA-N CO[NH+](c(cc12)ccc1nc(-c1cc(N)ccc1)[n]2O)[O-] Chemical compound CO[NH+](c(cc12)ccc1nc(-c1cc(N)ccc1)[n]2O)[O-] IQMOCCRAIJWKAG-UHFFFAOYSA-N 0.000 description 1
- KPPMTHUVVOUFOC-UHFFFAOYSA-N COc(cc(cc1)-c([n](c2c3)O)nc2ccc3[NH+]([O-])O)c1O Chemical compound COc(cc(cc1)-c([n](c2c3)O)nc2ccc3[NH+]([O-])O)c1O KPPMTHUVVOUFOC-UHFFFAOYSA-N 0.000 description 1
- DPFLFJZJMBZUNI-UHFFFAOYSA-N COc(cc1)cc(OC)c1-c1nc(ccc([N+](O)=O)c2)c2[n]1O Chemical compound COc(cc1)cc(OC)c1-c1nc(ccc([N+](O)=O)c2)c2[n]1O DPFLFJZJMBZUNI-UHFFFAOYSA-N 0.000 description 1
- HOEJMWBAZBZFER-UHFFFAOYSA-N COc(cc1)ccc1-c1nc(ccc([N+](O)=O)c2)c2[n]1O Chemical compound COc(cc1)ccc1-c1nc(ccc([N+](O)=O)c2)c2[n]1O HOEJMWBAZBZFER-UHFFFAOYSA-N 0.000 description 1
- FGCLDLAXLPHEEW-UHFFFAOYSA-N COc(ccc(-c1nc(ccc([N+]([O-4])=O)c2)c2[n]1O)c1)c1OC Chemical compound COc(ccc(-c1nc(ccc([N+]([O-4])=O)c2)c2[n]1O)c1)c1OC FGCLDLAXLPHEEW-UHFFFAOYSA-N 0.000 description 1
- CKSUEGYEOOXEBA-UHFFFAOYSA-N COc1cc(-c([n](c2c3)O)nc2ccc3[N+]([O-])=O)ccc1 Chemical compound COc1cc(-c([n](c2c3)O)nc2ccc3[N+]([O-])=O)ccc1 CKSUEGYEOOXEBA-UHFFFAOYSA-N 0.000 description 1
- MKPKUFYFBXOKTE-UHFFFAOYSA-N COc1cc(-c2nc(ccc([NH+]([O-])O)c3)c3[n]2O)cc(OC)c1OC Chemical compound COc1cc(-c2nc(ccc([NH+]([O-])O)c3)c3[n]2O)cc(OC)c1OC MKPKUFYFBXOKTE-UHFFFAOYSA-N 0.000 description 1
- ZJFPNRIWCSCUFT-UHFFFAOYSA-N CSc1ccc(C(Nc(c2c3)ccc3[N+]([O-])=O)N2O)cc1 Chemical compound CSc1ccc(C(Nc(c2c3)ccc3[N+]([O-])=O)N2O)cc1 ZJFPNRIWCSCUFT-UHFFFAOYSA-N 0.000 description 1
- DZHMAZFAUFAUHA-UHFFFAOYSA-N Cc(c(C)c1)ccc1[N+](O)=O Chemical compound Cc(c(C)c1)ccc1[N+](O)=O DZHMAZFAUFAUHA-UHFFFAOYSA-N 0.000 description 1
- UHBGYFCCKRAEHA-UHFFFAOYSA-N Cc(cc1)ccc1C(N)=O Chemical compound Cc(cc1)ccc1C(N)=O UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 description 1
- KJMNPGUHEUTHMR-UHFFFAOYSA-N Cc1cccc(C(NO)=N)c1 Chemical compound Cc1cccc(C(NO)=N)c1 KJMNPGUHEUTHMR-UHFFFAOYSA-N 0.000 description 1
- UAKAWWHOQNNATR-UHFFFAOYSA-N Cc1ccccc1C(NO)=N Chemical compound Cc1ccccc1C(NO)=N UAKAWWHOQNNATR-UHFFFAOYSA-N 0.000 description 1
- UACPBQAEDQTXMM-UHFFFAOYSA-N N=C(c(cc1)ccc1NCc1ccccc1)NO Chemical compound N=C(c(cc1)ccc1NCc1ccccc1)NO UACPBQAEDQTXMM-UHFFFAOYSA-N 0.000 description 1
- CLPULQLDSKYGSQ-UHFFFAOYSA-N N=C(c(cc1)ccc1NS(=O)=O)NO Chemical compound N=C(c(cc1)ccc1NS(=O)=O)NO CLPULQLDSKYGSQ-UHFFFAOYSA-N 0.000 description 1
- TUHCVZPTDBUXMQ-UHFFFAOYSA-N N=C(c(cc1)ccc1Oc1ccccc1)NO Chemical compound N=C(c(cc1)ccc1Oc1ccccc1)NO TUHCVZPTDBUXMQ-UHFFFAOYSA-N 0.000 description 1
- FJNGCQFGXMNISZ-UHFFFAOYSA-N N=C(c1ccc(CNC(c2ccccc2)=O)cc1)NO Chemical compound N=C(c1ccc(CNC(c2ccccc2)=O)cc1)NO FJNGCQFGXMNISZ-UHFFFAOYSA-N 0.000 description 1
- CLAHOZSYMRNIPY-UHFFFAOYSA-N NC(NCCO)=O Chemical compound NC(NCCO)=O CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 description 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N NC(c(cc1)ccc1Cl)=O Chemical compound NC(c(cc1)ccc1Cl)=O BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 description 1
- MJTGQALMWUUPQM-UHFFFAOYSA-N NC(c1cc(Cl)ccc1)=O Chemical compound NC(c1cc(Cl)ccc1)=O MJTGQALMWUUPQM-UHFFFAOYSA-N 0.000 description 1
- SXLQKSLYHNACFX-UHFFFAOYSA-N NC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=N Chemical compound NC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=N SXLQKSLYHNACFX-UHFFFAOYSA-N 0.000 description 1
- KGPOBHINXYYIPO-UHFFFAOYSA-O NC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=O Chemical compound NC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=O KGPOBHINXYYIPO-UHFFFAOYSA-O 0.000 description 1
- PHBWXPZUQTVKQT-UHFFFAOYSA-N Nc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+](O)=O Chemical compound Nc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+](O)=O PHBWXPZUQTVKQT-UHFFFAOYSA-N 0.000 description 1
- OZHAUABVHPMKOM-UHFFFAOYSA-N Nc(cccc1)c1-c([n](c1c2)O)nc1ccc2[N+]([O-])=O Chemical compound Nc(cccc1)c1-c([n](c1c2)O)nc1ccc2[N+]([O-])=O OZHAUABVHPMKOM-UHFFFAOYSA-N 0.000 description 1
- CFZHYRNQLHEHJS-UHFFFAOYSA-N Nc(cccc1)c1C(NO)=N Chemical compound Nc(cccc1)c1C(NO)=N CFZHYRNQLHEHJS-UHFFFAOYSA-N 0.000 description 1
- PKSNJHUPPDGFEC-UHFFFAOYSA-O OC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=O Chemical compound OC(c1cccc(-c([n](c2c3)O)nc2ccc3[N+](O)=O)c1)=O PKSNJHUPPDGFEC-UHFFFAOYSA-O 0.000 description 1
- SFVUPDINIWVHFW-UHFFFAOYSA-N O[n](c1c2)c(-c(cc3)cc4c3OCO4)nc1ccc2[N+](O)=O Chemical compound O[n](c1c2)c(-c(cc3)cc4c3OCO4)nc1ccc2[N+](O)=O SFVUPDINIWVHFW-UHFFFAOYSA-N 0.000 description 1
- RXBPQXKJPKUQCN-UHFFFAOYSA-O O[n](c1c2)c(-c(cc3)ccc3NC(c3ccccc3)=O)nc1ccc2[N+](O)=O Chemical compound O[n](c1c2)c(-c(cc3)ccc3NC(c3ccccc3)=O)nc1ccc2[N+](O)=O RXBPQXKJPKUQCN-UHFFFAOYSA-O 0.000 description 1
- VPJPTIGPSYBTPQ-UHFFFAOYSA-O O[n](c1c2)c(-c(cc3)ccc3NC(c3cnccc3)=O)nc1ccc2[N+](O)=O Chemical compound O[n](c1c2)c(-c(cc3)ccc3NC(c3cnccc3)=O)nc1ccc2[N+](O)=O VPJPTIGPSYBTPQ-UHFFFAOYSA-O 0.000 description 1
- WGUJGAHMTSMEGO-UHFFFAOYSA-N O[n](c1c2)c(-c3cc(OC(F)(F)F)ccc3)nc1ccc2[N+](O)=O Chemical compound O[n](c1c2)c(-c3cc(OC(F)(F)F)ccc3)nc1ccc2[N+](O)=O WGUJGAHMTSMEGO-UHFFFAOYSA-N 0.000 description 1
- WAFBZWKGUZVAOG-UHFFFAOYSA-N O[n]1c(-c2cc(-[n]3cccc3)ccc2)nc(cc2)c1cc2[N+](O)=O Chemical compound O[n]1c(-c2cc(-[n]3cccc3)ccc2)nc(cc2)c1cc2[N+](O)=O WAFBZWKGUZVAOG-UHFFFAOYSA-N 0.000 description 1
- QXZHGVLHHAUZOD-UHFFFAOYSA-N O[n]1c(-c2cc(Br)ccc2)nc(cc2)c1cc2[N+](O)=O Chemical compound O[n]1c(-c2cc(Br)ccc2)nc(cc2)c1cc2[N+](O)=O QXZHGVLHHAUZOD-UHFFFAOYSA-N 0.000 description 1
- XEFRWYWCTGFUNI-UHFFFAOYSA-O Oc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+](O)=O Chemical compound Oc(cc1)ccc1-c([n](c1c2)O)nc1ccc2[N+](O)=O XEFRWYWCTGFUNI-UHFFFAOYSA-O 0.000 description 1
- QMOBWYOTYUWHPA-UHFFFAOYSA-N [O-2][N+](C(C=C12)=CC(C3)C13N=C(c(cccc1)c1Br)N2O)=O Chemical compound [O-2][N+](C(C=C12)=CC(C3)C13N=C(c(cccc1)c1Br)N2O)=O QMOBWYOTYUWHPA-UHFFFAOYSA-N 0.000 description 1
- IVSJJXWLAXDQQT-UHFFFAOYSA-N [O-4][N+](c(cc12)ccc1nc(-c(cc1)ccc1NCCO)[n]2O)=O Chemical compound [O-4][N+](c(cc12)ccc1nc(-c(cc1)ccc1NCCO)[n]2O)=O IVSJJXWLAXDQQT-UHFFFAOYSA-N 0.000 description 1
- FOYREYGSLHFBRV-UHFFFAOYSA-N [O-][N+](c(cc12)ccc1nc(-c(cc1)ccc1NC(C1CCCCC1)=O)[n]2O)=O Chemical compound [O-][N+](c(cc12)ccc1nc(-c(cc1)ccc1NC(C1CCCCC1)=O)[n]2O)=O FOYREYGSLHFBRV-UHFFFAOYSA-N 0.000 description 1
- LSCZBBHTIUCHRK-UHFFFAOYSA-N [O-][N+](c(cc12)ccc1nc(-c(cccc1)c1NC(c1ccc[o]1)=O)[n]2O)=O Chemical compound [O-][N+](c(cc12)ccc1nc(-c(cccc1)c1NC(c1ccc[o]1)=O)[n]2O)=O LSCZBBHTIUCHRK-UHFFFAOYSA-N 0.000 description 1
- PAAAOMDCHZADHV-UHFFFAOYSA-N [O-][N+](c(cc12)ccc1nc(-c1cc(NC(c3ccc[o]3)=O)ccc1)[n]2O)=O Chemical compound [O-][N+](c(cc12)ccc1nc(-c1cc(NC(c3ccc[o]3)=O)ccc1)[n]2O)=O PAAAOMDCHZADHV-UHFFFAOYSA-N 0.000 description 1
- ZHRJLSAZMWHPNS-UHFFFAOYSA-N [O-][N+](c(cc12)ccc1nc(-c1cc(NC(c3ccccc3)=O)ccc1)[n]2O)=O Chemical compound [O-][N+](c(cc12)ccc1nc(-c1cc(NC(c3ccccc3)=O)ccc1)[n]2O)=O ZHRJLSAZMWHPNS-UHFFFAOYSA-N 0.000 description 1
- VEDKLSAVOFGKEE-UHFFFAOYSA-N [O-][N+]1(c(cc23)ccc2nc(-c(cccc2)c2NC(c2c[o]cc2)=O)[n]3O)OC1 Chemical compound [O-][N+]1(c(cc23)ccc2nc(-c(cccc2)c2NC(c2c[o]cc2)=O)[n]3O)OC1 VEDKLSAVOFGKEE-UHFFFAOYSA-N 0.000 description 1
- CPIFHUDZTIOEGM-UHFFFAOYSA-N [O-][NH+](c(cc12)ccc1nc(-c(cc1)ccc1NC(c1ccc[o]1)=O)[n]2O)[O-] Chemical compound [O-][NH+](c(cc12)ccc1nc(-c(cc1)ccc1NC(c1ccc[o]1)=O)[n]2O)[O-] CPIFHUDZTIOEGM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42331902P | 2002-11-01 | 2002-11-01 | |
| US60/423,319 | 2002-11-01 | ||
| US42591602P | 2002-11-13 | 2002-11-13 | |
| US60/425,916 | 2002-11-13 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004550495A Division JP2006513162A (ja) | 2002-11-01 | 2003-11-03 | 転写因子調節化合物およびその使用方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012039805A Division JP2012131813A (ja) | 2002-11-01 | 2012-02-27 | 転写因子調節化合物およびその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010235612A JP2010235612A (ja) | 2010-10-21 |
| JP2010235612A5 true JP2010235612A5 (enExample) | 2012-04-12 |
| JP5175316B2 JP5175316B2 (ja) | 2013-04-03 |
Family
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| WO2007016292A2 (en) * | 2005-07-27 | 2007-02-08 | Vertex Pharmaceuticals Incorporated | Heterocyclic amides as biofilm modulators |
| US7825154B2 (en) | 2005-08-12 | 2010-11-02 | The United States Of America As Represented By The Secretary Of The Army | Small molecule inhibitors of botulinum neurotoxins |
| WO2007053945A1 (en) * | 2005-11-09 | 2007-05-18 | Kane Biotech Inc. | Oral anti-microbial composition comprising competence-stimulating peptide |
| CN101626765B (zh) * | 2006-06-23 | 2012-12-26 | 帕拉特克药品公司 | 转录因子调节化合物及其使用方法 |
| MX2009005783A (es) * | 2006-12-01 | 2009-10-28 | Laclede Inc | Uso de enzimas hidroliticas y oxidativas para disolver bio-peliculas en los oidos. |
| EP2139474A2 (en) * | 2007-03-27 | 2010-01-06 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| EP2000140A1 (en) | 2007-06-05 | 2008-12-10 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Use of derivatives of 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine or of 3-oxo-2,3-dihydro-5H-imidazolo[3,2-a]pyrimidine for the preparation of pharmaceutical compositions intended for the treatment of cancer |
| JP5552121B2 (ja) * | 2008-09-04 | 2014-07-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン産生のインドリジン阻害剤 |
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| WO2010124097A2 (en) * | 2009-04-22 | 2010-10-28 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| WO2011151620A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2011151617A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2011151619A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| CA2801274C (en) * | 2010-06-01 | 2021-06-15 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile-associated disease |
| WO2011151618A2 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile-associated disease |
| US9382226B2 (en) * | 2010-07-21 | 2016-07-05 | Merck Sharp & Dohme Corp. | Aldosterone synthase inhibitors |
| CN105394046B (zh) | 2010-10-25 | 2019-03-01 | 范德比尔特大学 | 用于抑制昆虫宿主感觉的组合物 |
| US9677978B2 (en) * | 2011-05-02 | 2017-06-13 | José Carlos Lapenna | Fixative solution, for fixation and preservation of biological samples |
| CA2835328C (en) | 2011-05-06 | 2019-10-15 | Vanderbilt University | Compositions for inhibition of insect sensing |
| US9079935B2 (en) | 2012-08-13 | 2015-07-14 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting Clostridium-difficile associated disease |
| ITMI20132192A1 (it) * | 2013-12-23 | 2015-06-24 | Purisa S R L | Composti antimicrobici |
| US20180000793A1 (en) | 2015-02-06 | 2018-01-04 | Ernesto Abel-Santos | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
| CN107529746B (zh) | 2015-03-25 | 2021-09-07 | 范德比尔特大学 | 作为orco介导的气味感觉干扰剂的二元组合物 |
| US10472687B2 (en) | 2016-01-08 | 2019-11-12 | Institute For Systems Biology | Methods to identify antituberculosis compounds |
| US10738056B2 (en) | 2017-09-15 | 2020-08-11 | Aduro Biotech Inc. | Pyrazolopyrimidinone compounds and uses thereof |
| JP7730803B2 (ja) | 2019-07-17 | 2025-08-28 | サミット （オックスフォード） リミティド | リジニラゾールの調製方法およびその結晶形態 |
| JP7458622B2 (ja) * | 2019-09-18 | 2024-04-01 | 学校法人東京農業大学 | 抗生物質耐性微生物の耐性を低下させる物質及び抗生物質耐性微生物の耐性を低下させる方法 |
| CN110840897B (zh) * | 2019-11-28 | 2023-08-08 | 河北旺发生物科技有限公司 | 金属β-内酰胺酶抑制剂 |
| CN111166743B (zh) * | 2020-01-02 | 2022-03-22 | 中国医学科学院医药生物技术研究所 | 一类含噻唑结构化合物的抗感染用途 |
| GB202100470D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Solid tablet dosage for of ridinilazole |
| GB202100471D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Preparation of antibacterial compounds |
| US12220421B2 (en) | 2021-09-09 | 2025-02-11 | The Boards Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las | Inhibitors of C. difficile spore germination |
| KR102968141B1 (ko) * | 2023-11-28 | 2026-05-22 | 주식회사 에스씨바이오 | 반추동물의 메탄 저감제 |
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| CA2002859C (en) * | 1988-11-29 | 1998-12-29 | Jean P. F. Van Wauwe | Method of treating epithelial disorders |
| WO1998017267A1 (en) * | 1996-10-23 | 1998-04-30 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
| CA2341409A1 (en) * | 1998-08-31 | 2000-03-09 | Merck And Co., Inc. | Novel angiogenesis inhibitors |
| WO2004001058A2 (en) * | 2001-05-04 | 2003-12-31 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
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2003
- 2003-11-03 EP EP03783155A patent/EP1558341A4/en not_active Withdrawn
- 2003-11-03 CA CA2504448A patent/CA2504448C/en not_active Expired - Fee Related
- 2003-11-03 WO PCT/US2003/035205 patent/WO2004041209A2/en not_active Ceased
- 2003-11-03 JP JP2004550495A patent/JP2006513162A/ja active Pending
- 2003-11-03 AU AU2003291226A patent/AU2003291226B2/en not_active Ceased
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2010
- 2010-05-11 JP JP2010109145A patent/JP5175316B2/ja not_active Expired - Fee Related
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2012
- 2012-02-27 JP JP2012039805A patent/JP2012131813A/ja active Pending