JP4887297B2 - 新規二環式抗生物質 - Google Patents
新規二環式抗生物質 Download PDFInfo
- Publication number
- JP4887297B2 JP4887297B2 JP2007532823A JP2007532823A JP4887297B2 JP 4887297 B2 JP4887297 B2 JP 4887297B2 JP 2007532823 A JP2007532823 A JP 2007532823A JP 2007532823 A JP2007532823 A JP 2007532823A JP 4887297 B2 JP4887297 B2 JP 4887297B2
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- JP
- Japan
- Prior art keywords
- methoxy
- pyran
- tetrahydro
- methyl
- pyrido
- 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.)
- Expired - Fee Related
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- 125000002619 bicyclic group Chemical group 0.000 title description 8
- 239000003242 anti bacterial agent Substances 0.000 title description 7
- 229940088710 antibiotic agent Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 500
- -1 CH 2 CH 2 Chemical group 0.000 claims description 409
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 43
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 29
- 208000015181 infectious disease Diseases 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- VUHCPMIDSUGHNO-UHFFFAOYSA-N 6-methoxy-1,5-naphthyridin-4-amine Chemical compound N1=CC=C(N)C2=NC(OC)=CC=C21 VUHCPMIDSUGHNO-UHFFFAOYSA-N 0.000 claims description 22
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 229910052720 vanadium Inorganic materials 0.000 claims description 19
- SZHYPQDQYNLZJP-UHFFFAOYSA-N 3-oxo-4h-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid Chemical compound S1CC(=O)NC2=NC(C(=O)O)=CC=C21 SZHYPQDQYNLZJP-UHFFFAOYSA-N 0.000 claims description 18
- DMBFCTCQROWGDZ-UHFFFAOYSA-N 8-aminoquinoline-2-carbonitrile Chemical compound C1=C(C#N)N=C2C(N)=CC=CC2=C1 DMBFCTCQROWGDZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 claims description 7
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 229940080818 propionamide Drugs 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- OZPJIRXJDSOKHR-QUCCMNQESA-N (3r,6s)-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-[(6-methoxyquinolin-4-yl)oxymethyl]-3,6-dihydro-2h-pyran-3-amine Chemical compound O1CCOC2=CC(CN[C@H]3CO[C@@H](C=C3)COC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 OZPJIRXJDSOKHR-QUCCMNQESA-N 0.000 claims description 4
- SAWUQEVPMWWDHE-MJGOQNOKSA-N (3r,6s)-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-6-[[6-(trifluoromethoxy)quinolin-4-yl]oxymethyl]oxan-3-amine Chemical compound O1CCOC2=CC(CN[C@@H]3CC[C@H](OC3)COC3=CC=NC4=CC=C(C=C43)OC(F)(F)F)=CC=C21 SAWUQEVPMWWDHE-MJGOQNOKSA-N 0.000 claims description 4
- RYJFLQNHKUSOSN-QUURXOELSA-N 2-[(2r,3r,6s)-3-(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)-6-[(6-methoxyquinolin-4-yl)oxymethyl]oxan-2-yl]ethanol Chemical compound O1CCOC2=CC(CN[C@@H]3CC[C@H](O[C@@H]3CCO)COC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 RYJFLQNHKUSOSN-QUURXOELSA-N 0.000 claims description 4
- ZGRCWCPMDGISKX-UHFFFAOYSA-N 2-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-3-yl]oxy-n-(6-methoxy-1,5-naphthyridin-4-yl)acetamide Chemical compound O1CCOC2=CC(CN3CCCC(C3)OCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 ZGRCWCPMDGISKX-UHFFFAOYSA-N 0.000 claims description 4
- IBKNBOIAZHYDGT-UHFFFAOYSA-N 3-[(2,3-dihydro-1,4-benzodioxin-6-ylmethylamino)methyl]-n-(6-methoxy-1,5-naphthyridin-4-yl)cyclohexane-1-carboxamide Chemical compound O1CCOC2=CC(CNCC3CCCC(C3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 IBKNBOIAZHYDGT-UHFFFAOYSA-N 0.000 claims description 4
- LWQFODXSZNXRJK-UHFFFAOYSA-N 3-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-3-yl]-n-(6-methoxy-1,5-naphthyridin-4-yl)propanamide Chemical compound O1CCOC2=CC(CN3CCCC(C3)CCC(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 LWQFODXSZNXRJK-UHFFFAOYSA-N 0.000 claims description 4
- SGJJRJCYWAKOAB-UHFFFAOYSA-N 4-[3-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-3-yl]propoxy]-6-methoxyquinoline Chemical compound O1CCOC2=CC(CN3CCCC(C3)CCCOC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 SGJJRJCYWAKOAB-UHFFFAOYSA-N 0.000 claims description 4
- ZIEKVRDXDUZMKV-QZTJIDSGSA-N 6-[[[(3r,6r)-6-[2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]oxan-3-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](OC3)CCC3=CC=NC4=CC=C(N=C43)OC)=CC=C21 ZIEKVRDXDUZMKV-QZTJIDSGSA-N 0.000 claims description 4
- XTVIZXPGQNSAAD-CSMHICIZSA-N 6-[[[(3r,6s)-6-[(1r,2r)-1,2-dihydroxy-2-(2-methoxyquinolin-8-yl)ethyl]oxan-3-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](OC3)[C@H](O)[C@H](O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 XTVIZXPGQNSAAD-CSMHICIZSA-N 0.000 claims description 4
- AEXGVGHPHQYFRY-WBVHZDCISA-N 6-[[[(3r,6s)-6-[(6-methoxyquinazolin-4-yl)oxymethyl]oxan-3-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](OC3)COC3=NC=NC4=CC=C(C=C43)OC)=CC=C21 AEXGVGHPHQYFRY-WBVHZDCISA-N 0.000 claims description 4
- OLCCWRYDKCOIAL-WBVHZDCISA-N 6-[[[(3r,6s)-6-[[6-(difluoromethoxy)quinolin-4-yl]oxymethyl]oxan-3-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CC[C@H](OC3)COC3=CC=NC4=CC=C(C=C43)OC(F)F)=CC=C21 OLCCWRYDKCOIAL-WBVHZDCISA-N 0.000 claims description 4
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- UZRUMQUUKVUMDW-MSOLQXFVSA-N COC1=NC2=C(C=CC=C2C=C1)OC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O Chemical compound COC1=NC2=C(C=CC=C2C=C1)OC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O UZRUMQUUKVUMDW-MSOLQXFVSA-N 0.000 claims description 4
- ATPPWLOWFZEMHD-RTBURBONSA-N COC=1C=C2C(=CC=NC2=CC1)CC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O Chemical compound COC=1C=C2C(=CC=NC2=CC1)CC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O ATPPWLOWFZEMHD-RTBURBONSA-N 0.000 claims description 4
- XYSAVGPMHCKSAR-IAGOWNOFSA-N COC=1C=C2C(=NC=NC2=CC1)CC[C@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O Chemical compound COC=1C=C2C(=NC=NC2=CC1)CC[C@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O XYSAVGPMHCKSAR-IAGOWNOFSA-N 0.000 claims description 4
- URUTUUJBQUGCPL-GOEBONIOSA-N COC=1C=C2C(=NC=NC2=CC1)OC[C@H]1CC[C@@H](CN1)NCC=1C=CC=2SCC(NC2N1)=O Chemical compound COC=1C=C2C(=NC=NC2=CC1)OC[C@H]1CC[C@@H](CN1)NCC=1C=CC=2SCC(NC2N1)=O URUTUUJBQUGCPL-GOEBONIOSA-N 0.000 claims description 4
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- MQOAHXYINJFQIW-SUMWQHHRSA-N COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1NC[C@H](CC1)NCC=1C=CC=2SCC(NC2N1)=O Chemical compound COC=1N=C2C(=CC=NC2=CC1)NC(=O)[C@@H]1NC[C@H](CC1)NCC=1C=CC=2SCC(NC2N1)=O MQOAHXYINJFQIW-SUMWQHHRSA-N 0.000 claims description 4
- ZHLREKUJEDPHPP-WBVHZDCISA-N COc1ccc2ncnc(OC[C@H]3OC[C@H](NCc4ccc5SCC(=O)Nc5n4)C=C3)c2c1 Chemical compound COc1ccc2ncnc(OC[C@H]3OC[C@H](NCc4ccc5SCC(=O)Nc5n4)C=C3)c2c1 ZHLREKUJEDPHPP-WBVHZDCISA-N 0.000 claims description 4
- RPZKLORZJGAGKW-MSOLQXFVSA-N FC=1C=C(C=C2C(=CC=NC12)CC[C@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O)OC Chemical compound FC=1C=C(C=C2C(=CC=NC12)CC[C@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O)OC RPZKLORZJGAGKW-MSOLQXFVSA-N 0.000 claims description 4
- WUQJSSZDEKOWSM-CVEARBPZSA-N FC=1C=C(C=C2C(=CC=NC12)OC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O)OC Chemical compound FC=1C=C(C=C2C(=CC=NC12)OC[C@@H]1CC[C@H](CO1)NCC=1C=CC=2SCC(NC2N1)=O)OC WUQJSSZDEKOWSM-CVEARBPZSA-N 0.000 claims description 4
- BTWQMHQCJBRYSE-UHFFFAOYSA-N N-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-1-[3-[(6-methoxyquinolin-4-yl)oxymethyl]cyclohexyl]methanamine Chemical compound O1CCOC2=CC(CNCC3CCCC(C3)COC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 BTWQMHQCJBRYSE-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
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- HYVROMBCNMMAHD-ZJUUUORDSA-N tert-butyl n-[(3r,6s)-6-(2-hydroxyethyl)oxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](CCO)OC1 HYVROMBCNMMAHD-ZJUUUORDSA-N 0.000 description 1
- JFRDAJHOMKAWKJ-BDAKNGLRSA-N tert-butyl n-[(3r,6s)-6-(iodomethyl)oxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](CI)OC1 JFRDAJHOMKAWKJ-BDAKNGLRSA-N 0.000 description 1
- GPZRZAWTGUGMPB-AUENNLLBSA-N tert-butyl n-[(3r,6s)-6-[(1r,2r)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1,2-dihydroxyethyl]oxan-3-yl]carbamate Chemical compound C([C@H]1[C@H](O)[C@H](O)C2=C(F)C=NC3=CC=C(N=C32)OC)C[C@@H](NC(=O)OC(C)(C)C)CO1 GPZRZAWTGUGMPB-AUENNLLBSA-N 0.000 description 1
- UFWYCGUABLMAIH-PVAVHDDUSA-N tert-butyl n-[(3r,6s)-6-[(1s)-1-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]oxan-3-yl]carbamate Chemical compound C([C@H]1[C@@H](O)CC2=CC=NC3=CC=C(N=C32)OC)C[C@@H](NC(=O)OC(C)(C)C)CO1 UFWYCGUABLMAIH-PVAVHDDUSA-N 0.000 description 1
- JIDWDTKCBYAIFJ-NHAHKUSKSA-N tert-butyl n-[(3r,6s)-6-[(1s,2s)-1,2-dihydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]oxan-3-yl]carbamate Chemical compound C([C@H]1[C@@H](O)[C@@H](O)C2=CC=NC3=CC=C(N=C32)OC)C[C@@H](NC(=O)OC(C)(C)C)CO1 JIDWDTKCBYAIFJ-NHAHKUSKSA-N 0.000 description 1
- QPWWFBVVWVKMJE-ZBFHGGJFSA-N tert-butyl n-[(3r,6s)-6-[(6-methoxyquinolin-4-yl)oxymethyl]oxan-3-yl]carbamate Chemical compound C12=CC(OC)=CC=C2N=CC=C1OC[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)CO1 QPWWFBVVWVKMJE-ZBFHGGJFSA-N 0.000 description 1
- SWYMLLWXJQSYOH-HIFBNBFRSA-N tert-butyl n-[(3r,6s)-6-[(e)-2-(6-methoxy-1,5-naphthyridin-4-yl)ethenyl]oxan-3-yl]carbamate Chemical compound C12=NC(OC)=CC=C2N=CC=C1\C=C\[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)CO1 SWYMLLWXJQSYOH-HIFBNBFRSA-N 0.000 description 1
- CZJXTYUOEUGEDS-SLLSNFPASA-N tert-butyl n-[(3r,6s)-6-[(e)-2-(6-methoxyquinolin-4-yl)ethenyl]oxan-3-yl]carbamate Chemical compound C12=CC(OC)=CC=C2N=CC=C1\C=C\[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)CO1 CZJXTYUOEUGEDS-SLLSNFPASA-N 0.000 description 1
- ABKQDNYYKUYMQD-SFYZADRCSA-N tert-butyl n-[(3r,6s)-6-carbamoyloxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](C(N)=O)OC1 ABKQDNYYKUYMQD-SFYZADRCSA-N 0.000 description 1
- BGPQBSLWCUUQJR-NXEZZACHSA-N tert-butyl n-[(3r,6s)-6-ethenyloxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](C=C)OC1 BGPQBSLWCUUQJR-NXEZZACHSA-N 0.000 description 1
- MHWXWINFGYHRDC-NXEZZACHSA-N tert-butyl n-[(3r,6s)-6-ethynyloxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](C#C)OC1 MHWXWINFGYHRDC-NXEZZACHSA-N 0.000 description 1
- RWOHBVPVOZWRMG-BDAKNGLRSA-N tert-butyl n-[(3r,6s)-6-formyloxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](C=O)OC1 RWOHBVPVOZWRMG-BDAKNGLRSA-N 0.000 description 1
- LKBZAGUOZDYGKG-DTWKUNHWSA-N tert-butyl n-[(3s,6r)-6-(hydroxymethyl)oxan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CC[C@H](CO)OC1 LKBZAGUOZDYGKG-DTWKUNHWSA-N 0.000 description 1
- GRCYJTGPLQQLOX-DZGCQCFKSA-N tert-butyl n-[(3s,6r)-6-[(1-phenyltetrazol-5-yl)sulfonylmethyl]oxan-3-yl]carbamate Chemical compound O1C[C@@H](NC(=O)OC(C)(C)C)CC[C@@H]1CS(=O)(=O)C1=NN=NN1C1=CC=CC=C1 GRCYJTGPLQQLOX-DZGCQCFKSA-N 0.000 description 1
- UFWYCGUABLMAIH-BHYGNILZSA-N tert-butyl n-[(3s,6r)-6-[(1s)-1-hydroxy-2-(6-methoxy-1,5-naphthyridin-4-yl)ethyl]oxan-3-yl]carbamate Chemical compound C([C@@H]1[C@@H](O)CC2=CC=NC3=CC=C(N=C32)OC)C[C@H](NC(=O)OC(C)(C)C)CO1 UFWYCGUABLMAIH-BHYGNILZSA-N 0.000 description 1
- DBWREWKJBLECNR-UHFFFAOYSA-N tert-butyl n-[[3-(hydroxymethyl)cyclohexyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCCC(CO)C1 DBWREWKJBLECNR-UHFFFAOYSA-N 0.000 description 1
- CMVVPOBIZHZLEI-UHFFFAOYSA-N tert-butyl n-[[3-[(2-cyanoquinolin-8-yl)carbamoyl]cyclohexyl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCCC1C(=O)NC1=CC=CC2=CC=C(C#N)N=C12 CMVVPOBIZHZLEI-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2004/010762 | 2004-09-24 | ||
| EP2004010762 | 2004-09-24 | ||
| EP2005007731 | 2005-07-15 | ||
| EPPCT/EP2005/007731 | 2005-07-15 | ||
| PCT/EP2005/010154 WO2006032466A2 (en) | 2004-09-24 | 2005-09-20 | New bicyclic antibiotics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008514563A JP2008514563A (ja) | 2008-05-08 |
| JP2008514563A5 JP2008514563A5 (https=) | 2011-12-08 |
| JP4887297B2 true JP4887297B2 (ja) | 2012-02-29 |
Family
ID=36090370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532823A Expired - Fee Related JP4887297B2 (ja) | 2004-09-24 | 2005-09-20 | 新規二環式抗生物質 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP4887297B2 (https=) |
| AR (1) | AR050958A1 (https=) |
| CA (1) | CA2580621A1 (https=) |
| TW (1) | TW200615267A (https=) |
| WO (1) | WO2006032466A2 (https=) |
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| EP1845995A4 (en) * | 2005-01-25 | 2010-03-03 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
| MX2007014507A (es) * | 2005-05-24 | 2008-02-07 | Astrazeneca Ab | Aminopiperidin quinolinas y sus analogos azaisostericos con actividad antibacteriana. |
| MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| ATE536351T1 (de) | 2006-01-26 | 2011-12-15 | Actelion Pharmaceuticals Ltd | Tetrahydropyran-antibiotika |
| ES2353829T3 (es) | 2006-02-15 | 2011-03-07 | Actelion Pharmaceuticals Ltd. | Derivados antibioticos de etanol o de 1,2-etanodiolciclohexilo. |
| CA2643962A1 (en) * | 2006-03-10 | 2007-09-20 | Actelion Pharmaceuticals Ltd | Antibiotic compounds |
| EP2001887B1 (en) | 2006-04-06 | 2010-09-15 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| TW200815425A (en) * | 2006-06-08 | 2008-04-01 | Speedel Experimenta Ag | 2,5-disubstituted piperidines |
| EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
| TW200819457A (en) * | 2006-08-30 | 2008-05-01 | Actelion Pharmaceuticals Ltd | Spiro antibiotic derivatives |
| CL2007003693A1 (es) * | 2006-12-22 | 2008-06-27 | Actelion Pharmaceuticals Ltd | Compuestos derivados de pirido [3,2-b] [1,4] tiazina; composicion farmaceutica que contiene dichos compuestos; y su uso en el tratamiento de infecciones bacterianas. |
| CL2008001002A1 (es) | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| CL2008001003A1 (es) | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| AU2008240764C1 (en) | 2007-04-20 | 2011-10-20 | Glaxo Group Limited | Tricyclic nitrogen containing compounds as antibacterial agents |
| ATE520687T1 (de) * | 2007-06-15 | 2011-09-15 | Actelion Pharmaceuticals Ltd | 3-amino-6-(1-amino-ethyl)-tetrahydropyranderiva e |
| EP2005995A1 (en) * | 2007-06-22 | 2008-12-24 | Glaxo Group Limited | Heterocyclic compounds for the treatment of tuberculosis |
| PL2245028T3 (pl) | 2007-12-18 | 2012-07-31 | Actelion Pharmaceuticals Ltd | Pochodne 5-aminocyklilometyloksazolidyn-2-onu |
| EP2080761A1 (en) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Compounds |
| ES2411930T3 (es) | 2008-02-20 | 2013-07-09 | Actelion Pharmaceuticals Ltd. | Compuestos antibióticos azatricíclicos |
| TW200944529A (en) | 2008-04-15 | 2009-11-01 | Actelion Pharmaceuticals Ltd | Tricyclic antibiotics |
| MX2010012855A (es) | 2008-06-03 | 2010-12-21 | Actelion Pharmaceuticals Ltd | Derivados de [4-(1-amino-etil)-ciclohexil]-metil-amina y [6-(1-amino-etil)-tetrahidro-piran-3-il]-metil-amina como antibacterianos. |
| CN102105467A (zh) | 2008-08-04 | 2011-06-22 | 埃科特莱茵药品有限公司 | 三环烷氨基甲基噁唑烷酮衍生物 |
| DK2344495T3 (en) | 2008-10-07 | 2015-02-02 | Actelion Pharmaceuticals Ltd | TRICYCLIC OXAZOLIDINON ANTIBIOTIC COMPOUNDS |
| EP2352734A1 (en) | 2008-10-17 | 2011-08-10 | Glaxo Group Limited | Tricyclic nitrogen compounds used as antibacterials |
| BRPI0921038A2 (pt) | 2008-11-17 | 2019-09-24 | Hoffmann La Roche | ácido naftilacéticos |
| AU2009325902B2 (en) | 2008-12-12 | 2015-01-29 | Idorsia Pharmaceuticals Ltd | 5-amino-2-(1-hydroxy-ethyl)-tetrahydropyran derivatives |
| US8318940B2 (en) | 2009-01-15 | 2012-11-27 | Glaxo Group Limited | Naphthyridin-2 (1 H)-one compounds useful as antibacterials |
| AU2010206161B2 (en) | 2009-01-21 | 2014-08-07 | Basilea Pharmaceutica Ag | Novel bicyclic antibiotics |
| AR076222A1 (es) | 2009-04-09 | 2011-05-26 | Actelion Pharmaceuticals Ltd | Derivados 2-hidroxietil-1h-quinolin-ona y sus analogos azaisotericos con actividad antibacteriana y composiciones farmaceuticas que los contienen |
| BR112013007566A2 (pt) | 2010-09-28 | 2016-08-02 | Panacea Biotec Ltd | novos compostos bicíclicos |
| SG193002A1 (en) | 2011-03-10 | 2013-09-30 | Daiichi Sankyo Co Ltd | Dispiropyrrolidine derivative |
| EP2685828A4 (en) * | 2011-03-17 | 2014-08-13 | Merck Sharp & Dohme | SUBSTITUTED 3-AZABICYCLO [3,1,0-] HEXAN DERIVATIVES AS CCR2 ANTAGONISTS |
| KR102143660B1 (ko) * | 2011-06-17 | 2020-08-11 | 화이자 안티-인펙티브스 에이비 | 트랜스-7-옥소-6-(술포옥시)-1,6-디아자비시클로[3,2,1]옥탄-2-카르복스아미드 및 그의 염을 포함하는 헤테로시클릭 화합물의 제조 방법 |
| CA2840060A1 (en) * | 2011-06-27 | 2013-01-03 | Kyorin Pharmaceutical Co., Ltd. | Bridged bicyclic compounds for the treatment of bacterial infections |
| US8470884B2 (en) | 2011-11-09 | 2013-06-25 | Hoffmann-La Roche Inc. | Alkenyl naphthylacetic acids |
| TW201326180A (zh) | 2011-11-30 | 2013-07-01 | Actelion Pharmaceuticals Ltd | ３，７－二取代八氫－２Ｈ－吡啶并［４，３－ｅ］［１，３］□嗪－２－酮抗生素 |
| US10702521B2 (en) | 2014-08-22 | 2020-07-07 | Glaxosmithkline Intellectual Property Development Limited | Methods for treating neisseria gonorrhoeae infection with substituted 1,2-dihydro-2A,5,8A-triazaacenaphthylene-3,8-diones |
| TW201722965A (zh) | 2015-08-16 | 2017-07-01 | 葛蘭素史密斯克藍智慧財產發展有限公司 | 用於抗菌應用之化合物 |
| DK3676297T3 (da) * | 2017-09-01 | 2023-08-14 | Denali Therapeutics Inc | Forbindelser, sammensætninger og fremgangsmåder |
| MY202326A (en) | 2017-09-14 | 2024-04-24 | Daiichi Sankyo Co Ltd | Compound having cyclic structure |
| CN109082280B (zh) * | 2018-11-05 | 2020-07-28 | 宁夏中星显示材料有限公司 | 一种液晶材料的制备方法 |
| US12091392B2 (en) | 2019-02-13 | 2024-09-17 | Denali Therapeutics Inc. | Compounds, compositions and methods |
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| WO2003064421A1 (en) * | 2002-01-29 | 2003-08-07 | Glaxo Group Limited | Aminopiperidine derivatives |
| WO2004002992A1 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Compounds |
| WO2004002490A2 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Piperidine compounds as antibacterials |
| WO2004035569A2 (de) * | 2002-10-10 | 2004-04-29 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue verbindungen mit antibakterieller aktivität |
| DE10256405A1 (de) * | 2002-12-02 | 2004-06-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen, die Topoisomerase IV inhibieren |
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| DE10316081A1 (de) * | 2003-04-08 | 2004-10-21 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
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- 2005-09-20 JP JP2007532823A patent/JP4887297B2/ja not_active Expired - Fee Related
- 2005-09-20 WO PCT/EP2005/010154 patent/WO2006032466A2/en not_active Ceased
- 2005-09-20 CA CA002580621A patent/CA2580621A1/en not_active Abandoned
- 2005-09-21 TW TW094132686A patent/TW200615267A/zh unknown
- 2005-09-26 AR ARP050104029A patent/AR050958A1/es unknown
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| WO2004089942A2 (en) * | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| WO2003064421A1 (en) * | 2002-01-29 | 2003-08-07 | Glaxo Group Limited | Aminopiperidine derivatives |
| WO2004002992A1 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Compounds |
| WO2004002490A2 (en) * | 2002-06-26 | 2004-01-08 | Glaxo Group Limited | Piperidine compounds as antibacterials |
| WO2004035569A2 (de) * | 2002-10-10 | 2004-04-29 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue verbindungen mit antibakterieller aktivität |
| DE10256405A1 (de) * | 2002-12-02 | 2004-06-17 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen, die Topoisomerase IV inhibieren |
| WO2006012396A1 (en) * | 2004-07-22 | 2006-02-02 | Glaxo Group Limited | Antibacterial agents |
| WO2006021448A1 (en) * | 2004-08-25 | 2006-03-02 | Morphochem Aktiengesellschaft für kombinatorische Chemie | Novel compounds having an anti-bacterial activity |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2580621A1 (en) | 2006-03-30 |
| TW200615267A (en) | 2006-05-16 |
| WO2006032466A2 (en) | 2006-03-30 |
| JP2008514563A (ja) | 2008-05-08 |
| WO2006032466A3 (en) | 2006-12-14 |
| AR050958A1 (es) | 2006-12-06 |
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