DE69716925T2 - Isoxazoline derivate und ihre verwendung als antimikroben - Google Patents
Isoxazoline derivate und ihre verwendung als antimikrobenInfo
- Publication number
- DE69716925T2 DE69716925T2 DE69716925T DE69716925T DE69716925T2 DE 69716925 T2 DE69716925 T2 DE 69716925T2 DE 69716925 T DE69716925 T DE 69716925T DE 69716925 T DE69716925 T DE 69716925T DE 69716925 T2 DE69716925 T2 DE 69716925T2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- methyl
- isoxazolyl
- acetamide
- phenyl
- 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
Links
- 150000002547 isoxazolines Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- -1 (±)-N-[[4,5-Dihydro-3-[4-[1-(4-oxo-2-thiadiazolinyl)-3,6-dihydro-2H-pyridin-4-yl]-3,5 -difluorophenyl]-5-isoxazolyl]methyl]acetamide Chemical compound 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZPNPRXYSBVYQRW-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-pyridin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)N2CC=CCC2)=N1 ZPNPRXYSBVYQRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- LGLMAJVQLRZTNE-UHFFFAOYSA-N tert-butyl 4-[4-[5-(acetamidomethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CC=2)C(=O)OC(C)(C)C)=N1 LGLMAJVQLRZTNE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- UZDQAKCZSLBAOL-QGZVFWFLSA-N n-[[(5r)-3-[4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1[C@@H](CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CC=2)C(=O)CO)=N1 UZDQAKCZSLBAOL-QGZVFWFLSA-N 0.000 claims description 4
- GTQULBMUHWIQCZ-UHFFFAOYSA-N n-[[3-[4-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CC=2)C(C)=O)=N1 GTQULBMUHWIQCZ-UHFFFAOYSA-N 0.000 claims description 4
- QWAWTNNQWBSDDT-UHFFFAOYSA-N n-[[3-[4-(4-methoxy-5-oxocyclohepta-1,3,6-trien-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound C1=CC(=O)C(OC)=CC=C1C1=CC=C(C=2CC(CNC(C)=O)ON=2)C=C1 QWAWTNNQWBSDDT-UHFFFAOYSA-N 0.000 claims description 4
- NRALJEUUKOLTFO-UHFFFAOYSA-N n-[[3-[4-(thian-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C2CCSCC2)=N1 NRALJEUUKOLTFO-UHFFFAOYSA-N 0.000 claims description 4
- UZDQAKCZSLBAOL-UHFFFAOYSA-N n-[[3-[4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CC=2)C(=O)CO)=N1 UZDQAKCZSLBAOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- HRVZACOQSFRTKH-MRXNPFEDSA-N n-[[(5r)-3-(4-pyridin-4-ylphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1[C@@H](CNC(=O)C)CC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=N1 HRVZACOQSFRTKH-MRXNPFEDSA-N 0.000 claims description 3
- POXYVDFDXYIXRT-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-(thian-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCSCC3)=C(F)C=2)=N1 POXYVDFDXYIXRT-UHFFFAOYSA-N 0.000 claims description 3
- IBLBWRVAOWITGU-UHFFFAOYSA-N n-[[3-[3-fluoro-4-(thian-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCSCC3)=CC=2)=N1 IBLBWRVAOWITGU-UHFFFAOYSA-N 0.000 claims description 3
- PNJMIKJZKBMSSU-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-pyran-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCOCC=2)=N1 PNJMIKJZKBMSSU-UHFFFAOYSA-N 0.000 claims description 3
- BYSSENUPTFVDBR-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-thiopyran-4-yl)-3,5-difluorophenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCSCC=3)=C(F)C=2)=N1 BYSSENUPTFVDBR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- XDGXPUWESVCNHF-UHFFFAOYSA-N N-[[3-[3-fluoro-4-[1-(4-oxothiadiazol-5-yl)-3,6-dihydro-2H-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O=C1N=NSC1N1CCC(=CC1)C1=C(C=C(C=C1)C1=NOC(C1)CNC(C)=O)F XDGXPUWESVCNHF-UHFFFAOYSA-N 0.000 claims description 2
- NXXGWJQIEZFTKF-UHFFFAOYSA-N N-[[3-[3-fluoro-4-[1-(4-oxothiadiazol-5-yl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O=C1N=NSC1N1CCC(CC1)C1=C(C=C(C=C1)C1=NOC(C1)CNC(C)=O)F NXXGWJQIEZFTKF-UHFFFAOYSA-N 0.000 claims description 2
- FGTHJJZHHHMURK-UHFFFAOYSA-N N-[[3-[4-[1-(4-oxothiadiazol-5-yl)-3,6-dihydro-2H-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O=C1N=NSC1N1CCC(=CC1)C1=CC=C(C=C1)C1=NOC(C1)CNC(C)=O FGTHJJZHHHMURK-UHFFFAOYSA-N 0.000 claims description 2
- NUNHLATUJOIOAI-UHFFFAOYSA-N N-[[3-[4-[1-(4-oxothiadiazol-5-yl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O=C1N=NSC1N1CCC(CC1)C1=CC=C(C=C1)C1=NOC(C1)CNC(C)=O NUNHLATUJOIOAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- JIFUJSOILXJUCP-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-(4-methoxy-5-oxocyclohepta-1,3,6-trien-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound C1=CC(=O)C(OC)=CC=C1C1=C(F)C=C(C=2CC(CNC(C)=O)ON=2)C=C1F JIFUJSOILXJUCP-UHFFFAOYSA-N 0.000 claims description 2
- BUALKJBTSMBMMS-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCN(CC=3)C(=O)CO)=C(F)C=2)=N1 BUALKJBTSMBMMS-UHFFFAOYSA-N 0.000 claims description 2
- LYICOQOSBQRDGX-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCN(CC3)C(=O)CO)=C(F)C=2)=N1 LYICOQOSBQRDGX-UHFFFAOYSA-N 0.000 claims description 2
- BGTAJQSYNKLJQY-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCN(CC=3)C=3SC(C)=NN=3)=C(F)C=2)=N1 BGTAJQSYNKLJQY-UHFFFAOYSA-N 0.000 claims description 2
- JJZSPKWKDZNLKX-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCN(CC3)C=3SC(C)=NN=3)=C(F)C=2)=N1 JJZSPKWKDZNLKX-UHFFFAOYSA-N 0.000 claims description 2
- FBQRNEPVACMDRS-UHFFFAOYSA-N n-[[3-[3-fluoro-4-(4-methoxy-5-oxocyclohepta-1,3,6-trien-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound C1=CC(=O)C(OC)=CC=C1C1=CC=C(C=2CC(CNC(C)=O)ON=2)C=C1F FBQRNEPVACMDRS-UHFFFAOYSA-N 0.000 claims description 2
- ZDALXWVBHZTTFU-UHFFFAOYSA-N n-[[3-[3-fluoro-4-(oxan-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCOCC3)=CC=2)=N1 ZDALXWVBHZTTFU-UHFFFAOYSA-N 0.000 claims description 2
- ICEQPDLVSZXHHS-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCN(CC=3)C(=O)CO)=CC=2)=N1 ICEQPDLVSZXHHS-UHFFFAOYSA-N 0.000 claims description 2
- ARCMSUCTQZNZAG-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCN(CC3)C(=O)CO)=CC=2)=N1 ARCMSUCTQZNZAG-UHFFFAOYSA-N 0.000 claims description 2
- POSFVJGLSTWABU-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCN(CC=3)C=3SC(C)=NN=3)=CC=2)=N1 POSFVJGLSTWABU-UHFFFAOYSA-N 0.000 claims description 2
- OEXFVQLHZUBTAL-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCN(CC3)C=3SC(C)=NN=3)=CC=2)=N1 OEXFVQLHZUBTAL-UHFFFAOYSA-N 0.000 claims description 2
- IPZWKWFRYSNTRN-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-pyran-4-yl)-3,5-difluorophenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCOCC=3)=C(F)C=2)=N1 IPZWKWFRYSNTRN-UHFFFAOYSA-N 0.000 claims description 2
- ZWLBGPZGRAMCHK-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-pyran-4-yl)-3-fluorophenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCOCC=3)=CC=2)=N1 ZWLBGPZGRAMCHK-UHFFFAOYSA-N 0.000 claims description 2
- OJTAGZBBXMFKEK-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C=3CCSCC=3)=CC=2)=N1 OJTAGZBBXMFKEK-UHFFFAOYSA-N 0.000 claims description 2
- OFLKFKZIUYCCSD-UHFFFAOYSA-N n-[[3-[4-(3,6-dihydro-2h-thiopyran-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCSCC=2)=N1 OFLKFKZIUYCCSD-UHFFFAOYSA-N 0.000 claims description 2
- BMSAYUZOKUITAF-UHFFFAOYSA-N n-[[3-[4-(oxan-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C2CCOCC2)=N1 BMSAYUZOKUITAF-UHFFFAOYSA-N 0.000 claims description 2
- HARZNABJYQHOBT-UHFFFAOYSA-N n-[[3-[4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C2CCN(CC2)C(=O)CO)=N1 HARZNABJYQHOBT-UHFFFAOYSA-N 0.000 claims description 2
- YRUDDYNHKFKTTL-UHFFFAOYSA-N n-[[3-[4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CC=2)C=2SC(C)=NN=2)=N1 YRUDDYNHKFKTTL-UHFFFAOYSA-N 0.000 claims description 2
- KFITZXAUVFBIGM-UHFFFAOYSA-N n-[[3-[4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C2CCN(CC2)C=2SC(C)=NN=2)=N1 KFITZXAUVFBIGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 11
- 150000002825 nitriles Chemical class 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- 241000186367 Mycobacterium avium Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000004599 antimicrobial Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 description 3
- 208000022362 bacterial infectious disease Diseases 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 3
- 239000001974 tryptic soy broth Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000606125 Bacteroides Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241001112696 Clostridia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- QPTIGFZECTYUGC-UHFFFAOYSA-N [3-(4-pyridin-4-ylphenyl)-1,2-oxazol-5-yl]methanamine Chemical compound O1C(CN)=CC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=N1 QPTIGFZECTYUGC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000003971 isoxazolinyl group Chemical group 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- SIMWTRCFFSTNMG-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)CO)CC1 SIMWTRCFFSTNMG-AWEZNQCLSA-N 0.000 description 2
- PVEHHMPFRIYOQZ-UHFFFAOYSA-N n-[[3-(4-bromophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(Br)=CC=2)=N1 PVEHHMPFRIYOQZ-UHFFFAOYSA-N 0.000 description 2
- GSDJEQKAFUBQFV-UHFFFAOYSA-N n-[[3-(4-trimethylstannylphenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)[Sn](C)(C)C)=N1 GSDJEQKAFUBQFV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical class [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- YCBWXJZXFUKDPU-UHFFFAOYSA-N trimethyl(pyridin-4-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=NC=C1 YCBWXJZXFUKDPU-UHFFFAOYSA-N 0.000 description 2
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 2
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
- 108010050327 trypticase-soy broth Proteins 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 description 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- 125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 description 1
- AZWHPGZNOIYGFB-UHFFFAOYSA-N 1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1(C)CC(C)(C(O)=O)CC(C)(C(O)=O)C1 AZWHPGZNOIYGFB-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- QXMJAMBPNHRAPD-UHFFFAOYSA-N 1-oxido-3h-oxathiazol-1-ium Chemical compound [O-][O+]1SNC=C1 QXMJAMBPNHRAPD-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical group C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- IVHKZCSZELZKSJ-UHFFFAOYSA-N 2-hydroxyethyl sulfonate Chemical compound OCCOS(=O)=O IVHKZCSZELZKSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QWSQNLKNOPXCKY-UHFFFAOYSA-N 3h-1,2,4-dithiazole 1-oxide Chemical compound O=S1SCN=C1 QWSQNLKNOPXCKY-UHFFFAOYSA-N 0.000 description 1
- CHPTUAHBVDCEPL-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-ylmethanamine Chemical compound NCC1CC=NO1 CHPTUAHBVDCEPL-UHFFFAOYSA-N 0.000 description 1
- PHVFVPURCHVDBP-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-ylmethanol Chemical class OCC1CC=NO1 PHVFVPURCHVDBP-UHFFFAOYSA-N 0.000 description 1
- ZOPFQZFNZNMZEF-UHFFFAOYSA-N 4-bromo-n-hydroxybenzenecarboximidoyl chloride Chemical compound ON=C(Cl)C1=CC=C(Br)C=C1 ZOPFQZFNZNMZEF-UHFFFAOYSA-N 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- ZRDLQVIEHKAGPA-UHFFFAOYSA-N 5-(azidomethyl)-4,5-dihydro-1,2-oxazole Chemical compound [N-]=[N+]=NCC1CC=NO1 ZRDLQVIEHKAGPA-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- WXTVTJMZFUSBCG-UHFFFAOYSA-N N-[[3-[4-[1-(2-hydroxyacetyl)-2,3,6,7-tetrahydroazepin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=CC(=CC=2)C=2CCN(CCC=2)C(=O)CO)=N1 WXTVTJMZFUSBCG-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical compound N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007478 blood agar base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZPNPRXYSBVYQRW-MRXNPFEDSA-N n-[[(5r)-3-[4-(3,6-dihydro-2h-pyridin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1[C@@H](CNC(=O)C)CC(C=2C=CC(=CC=2)N2CC=CCC2)=N1 ZPNPRXYSBVYQRW-MRXNPFEDSA-N 0.000 description 1
- CIDMLMSQKFERPR-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-(oxan-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CCOCC3)=C(F)C=2)=N1 CIDMLMSQKFERPR-UHFFFAOYSA-N 0.000 description 1
- AXQOAGTVCXXTKY-UHFFFAOYSA-N n-[[3-[3,5-difluoro-4-[1-(2-hydroxyacetyl)-2,3,6,7-tetrahydroazepin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(=C(F)C=2)C=2CCN(CCC=2)C(=O)CO)=N1 AXQOAGTVCXXTKY-UHFFFAOYSA-N 0.000 description 1
- LFHLJXIEHQXGEF-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(2-hydroxyacetyl)-2,3,6,7-tetrahydroazepin-4-yl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(=CC=2)C=2CCN(CCC=2)C(=O)CO)=N1 LFHLJXIEHQXGEF-UHFFFAOYSA-N 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical group C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- QVWDCTQRORVHHT-UHFFFAOYSA-N tropone Chemical group O=C1C=CC=CC=C1 QVWDCTQRORVHHT-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2428796P | 1996-08-21 | 1996-08-21 | |
| PCT/US1997/013934 WO1998007708A1 (en) | 1996-08-21 | 1997-08-15 | Isoxazoline derivatives useful as antimicrobials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69716925D1 DE69716925D1 (de) | 2002-12-12 |
| DE69716925T2 true DE69716925T2 (de) | 2003-09-11 |
Family
ID=21819822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69716925T Expired - Fee Related DE69716925T2 (de) | 1996-08-21 | 1997-08-15 | Isoxazoline derivate und ihre verwendung als antimikroben |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5990136A (enExample) |
| EP (1) | EP0920421B1 (enExample) |
| JP (1) | JP2000516245A (enExample) |
| AT (1) | ATE227277T1 (enExample) |
| AU (1) | AU3973697A (enExample) |
| DE (1) | DE69716925T2 (enExample) |
| DK (1) | DK0920421T3 (enExample) |
| ES (1) | ES2186916T3 (enExample) |
| PT (1) | PT920421E (enExample) |
| WO (1) | WO1998007708A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| BR9815518A (pt) * | 1997-05-30 | 2000-11-21 | Upjohn Co | Agentes antibacterianos de oxazolidinona tendo funcionalidade de tiocarbonila |
| US6255304B1 (en) | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| NZ506292A (en) * | 1998-02-13 | 2003-05-30 | Upjohn Co | Substituted aminophenyl isoxazoline methylamide derivatives useful as antimicrobials |
| JP2002504550A (ja) * | 1998-02-25 | 2002-02-12 | ファルマシア・アンド・アップジョン・カンパニー | 抗微生物剤として有用な置換アミノメチルイソオキサゾリン誘導体 |
| NZ508174A (en) | 1998-06-05 | 2003-10-31 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| US6420349B1 (en) | 1998-08-24 | 2002-07-16 | Bristol-Myers Squibb Company | Isoxazolinone antibacterial agents |
| TW572757B (en) * | 1998-08-24 | 2004-01-21 | Bristol Myers Squibb Co | Novel isoxazolinone antibacterial agents |
| GB9928568D0 (en) * | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| US6465456B2 (en) | 2000-06-29 | 2002-10-15 | Bristol-Myers Squibb Company | Isoxazolinone antibacterial agents |
| JP2004518677A (ja) | 2000-12-21 | 2004-06-24 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌性キノロン誘導体および細菌感染を治療するためのその使用 |
| CA2432409A1 (en) * | 2000-12-26 | 2002-07-11 | Research Foundation Itsuu Laboratory | Tropolone derivative |
| EP1443930A1 (en) * | 2001-10-25 | 2004-08-11 | AstraZeneca AB | Isoxazoline derivatives useful as antimicrobials |
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| EP1594494A1 (en) * | 2003-02-07 | 2005-11-16 | Warner-Lambert Company LLC | Oxazolidinone derivatives n-substituted by a bicyclic ring, for use as antibacterial agents |
| JP2006516991A (ja) * | 2003-02-07 | 2006-07-13 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 抗菌剤 |
| US7304050B2 (en) * | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| WO2005082900A2 (en) * | 2004-01-28 | 2005-09-09 | Pharmacia & Upjohn Company Llc | Oxazolidinone amidoximes as antibacterial agents |
| CN101001853A (zh) * | 2004-08-06 | 2007-07-18 | 法玛西雅厄普约翰有限责任公司 | 作为抗细菌剂的含羟吲哚的唑烷酮类 |
| AU2005285130B2 (en) * | 2004-09-10 | 2011-09-15 | Syngenta Limited | Substituted isoxazoles as fungicides |
| CN103270036B (zh) * | 2010-08-05 | 2015-11-25 | 佐蒂斯有限责任公司 | 作为抗寄生物剂的异噁唑啉衍生物 |
| EP2655362A1 (en) | 2010-12-22 | 2013-10-30 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| WO2014055352A1 (en) * | 2012-10-03 | 2014-04-10 | Shell Oil Company | Optimizing performance of a drilling assembly |
| WO2021000297A1 (en) | 2019-07-03 | 2021-01-07 | Merck Sharp & Dohme Corp. | Compounds and methods of use thereof as antibacterial agents |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL137326C (enExample) * | 1967-08-26 | |||
| US4283403A (en) * | 1976-06-14 | 1981-08-11 | Eli Lilly And Company | Substituted isoxazolines for control of plant phytopathogens |
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| AU670842B2 (en) * | 1992-12-08 | 1996-08-01 | Pharmacia & Upjohn Company | Tropone-substituted phenyloxazolidinone antibacterial agents |
| EP0730587B1 (en) * | 1993-11-26 | 1999-12-08 | Pfizer Inc. | 3-phenyl-2-isoxazolines as antiinflammatory agents |
| DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| DE4425612A1 (de) * | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| US5710159A (en) * | 1996-05-09 | 1998-01-20 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
-
1997
- 1997-08-15 DK DK97937156T patent/DK0920421T3/da active
- 1997-08-15 DE DE69716925T patent/DE69716925T2/de not_active Expired - Fee Related
- 1997-08-15 WO PCT/US1997/013934 patent/WO1998007708A1/en not_active Ceased
- 1997-08-15 EP EP97937156A patent/EP0920421B1/en not_active Expired - Lifetime
- 1997-08-15 AT AT97937156T patent/ATE227277T1/de not_active IP Right Cessation
- 1997-08-15 ES ES97937156T patent/ES2186916T3/es not_active Expired - Lifetime
- 1997-08-15 PT PT97937156T patent/PT920421E/pt unknown
- 1997-08-15 AU AU39736/97A patent/AU3973697A/en not_active Abandoned
- 1997-08-15 JP JP10510781A patent/JP2000516245A/ja not_active Withdrawn
- 1997-08-15 US US08/999,753 patent/US5990136A/en not_active Expired - Fee Related
-
1999
- 1999-08-31 US US09/386,647 patent/US6093736A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0920421A1 (en) | 1999-06-09 |
| PT920421E (pt) | 2003-03-31 |
| AU3973697A (en) | 1998-03-06 |
| US6093736A (en) | 2000-07-25 |
| ATE227277T1 (de) | 2002-11-15 |
| WO1998007708A1 (en) | 1998-02-26 |
| ES2186916T3 (es) | 2003-05-16 |
| DK0920421T3 (da) | 2003-03-10 |
| EP0920421B1 (en) | 2002-11-06 |
| US5990136A (en) | 1999-11-23 |
| DE69716925D1 (de) | 2002-12-12 |
| JP2000516245A (ja) | 2000-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69716925T2 (de) | Isoxazoline derivate und ihre verwendung als antimikroben | |
| DE69902634T2 (de) | Substituierte aminophenylisoxazolinderivate verwendbar als antimikrobielle agenzien | |
| DE60205030T2 (de) | Oxazolidinon- und/oder isoxazolinderivate als antibakterielle mittel | |
| US6365751B1 (en) | Antibiotic oxazolidinone derivatives | |
| DE69829846T2 (de) | Antibakteriell wirksam oxazolidinone mit einer thiocarbonylfunktionalität | |
| DE69632074T2 (de) | Oxazolidinone mit tricyclische substituente als antibacterielle mittel | |
| DE69616366T2 (de) | Phenyloxazolidinone mit einer c-c-bindung zu 4-8 gliedrigen heterocyclen | |
| DE60210654T2 (de) | Aryl substituierte oxazolidinone mit antibacterieller activität | |
| DE60212959T2 (de) | Eine sulfonimid-gruppe enthaltende oxazolidinone als antibiotika | |
| DE69717630T2 (de) | 3-phenyl-furan-(5h)-2-on- und dihydrofuran-2-on-derivate als antibakterielle mittel | |
| DE60222645T2 (de) | Verfahren zur herstellung von oxazolidinonen | |
| DE60206154T2 (de) | Bicyclo[3,1,0]hexan als strukturelement enthaltende oxazolidinon-antibiotika und deren derivate | |
| US6281210B1 (en) | Benzoic acid esters of oxazolidinones having a hydroxyacetylpiperazine substituent | |
| US20040014967A1 (en) | Amide-containing compound having improved solubility and method of improving the solubility of an amide-containing compound | |
| US7279494B2 (en) | Antimicrobial [3.1.0] bicyclohexylphenyl-oxazolidinone derivatives and analogues | |
| CA2501352A1 (en) | Antimicrobial [3.1.0] bicyclic oxazolidinone derivatives | |
| DE60304360T2 (de) | N-aryl-2-oxazolidinone und deren derivate | |
| US6825225B2 (en) | Bicyclic isoxazolinones as antibacterial agents | |
| EP1660488A1 (en) | Novel antimicrobial aryloxazolidinone compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |