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
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- 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
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- 239000012298 atmosphere Substances 0.000 description 12
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- 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
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- 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
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- 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
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- 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
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- 239000008194 pharmaceutical composition Substances 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- 150000003254 radicals Chemical class 0.000 description 5
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- 229920001817 Agar Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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 |
| US6255304B1 (en) | 1997-05-30 | 2001-07-03 | Pharmacia & Upjohn Company | Oxazolidinone antibacterial agents having a thiocarbonyl functionality |
| DE69829846T2 (de) * | 1997-05-30 | 2006-02-23 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Antibakteriell wirksam oxazolidinone mit einer thiocarbonylfunktionalität |
| 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 |
| EP1054874B1 (en) * | 1998-02-13 | 2002-08-28 | PHARMACIA & UPJOHN COMPANY | Substituted aminophenyl isoxazoline derivatives useful as antimicrobials |
| EP1060179A1 (en) * | 1998-02-25 | 2000-12-20 | PHARMACIA & UPJOHN COMPANY | Substituted aminomethyl isoxazoline derivatives useful as antimicrobials |
| BR9910971A (pt) | 1998-06-05 | 2001-02-13 | Astrazeneca Ab | Composto, processos para a preparação de um composto e para produzir um efeito antibacteriano em um animal de sangue quente, uso de um composto, e, composição farmacêutica |
| TW572757B (en) * | 1998-08-24 | 2004-01-21 | Bristol Myers Squibb Co | Novel isoxazolinone antibacterial agents |
| US6420349B1 (en) | 1998-08-24 | 2002-07-16 | Bristol-Myers Squibb Company | 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 |
| WO2002059116A2 (en) | 2000-12-21 | 2002-08-01 | Pharmacia & Upjohn Company | Antimicrobial quinolone derivatives and use of the same to treat bacterial infections |
| AU2002222682B8 (en) * | 2000-12-26 | 2008-05-29 | Research Foundation Itsuu Laboratory | Tropolone Derivatives |
| JP2005512975A (ja) | 2001-10-25 | 2005-05-12 | アストラゼネカ アクチボラグ | 抗菌薬として有用なイソキサゾリン誘導体 |
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| CA2515311A1 (en) * | 2003-02-07 | 2004-08-19 | Warner-Lambert Company Llc | Antibacterial agents |
| WO2004069244A1 (en) * | 2003-02-07 | 2004-08-19 | Warner-Lambert Company Llc | Oxazolidinone derivatives n-substituted by a bicyclic ring, for use as antibacterial agents |
| 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 |
| US20080262056A1 (en) * | 2004-08-06 | 2008-10-23 | Pfizer Inc | Oxindole Oxazolidinones as Antibacterial Agents |
| AU2005285130B2 (en) * | 2004-09-10 | 2011-09-15 | Syngenta Limited | Substituted isoxazoles as fungicides |
| ES2682303T3 (es) * | 2010-08-05 | 2018-09-19 | Zoetis Services Llc | Derivados de isoxazolina como agentes antiparasitarios |
| US9173887B2 (en) | 2010-12-22 | 2015-11-03 | 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 |
| CZ288788B6 (cs) * | 1992-12-08 | 2001-09-12 | Pharmacia & Upjohn Company | Antibakteriální fenyloxazolidinony substituované troponem |
| DK0730587T3 (da) * | 1993-11-26 | 2000-04-10 | Pfizer | 3-phenyl-2-isoxazoliner som anti-inflammatoriske midler |
| DE4425612A1 (de) * | 1994-07-20 | 1996-04-04 | Bayer Ag | 6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone |
| DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| US5710159A (en) * | 1996-05-09 | 1998-01-20 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
-
1997
- 1997-08-15 AU AU39736/97A patent/AU3973697A/en not_active Abandoned
- 1997-08-15 EP EP97937156A patent/EP0920421B1/en not_active Expired - Lifetime
- 1997-08-15 PT PT97937156T patent/PT920421E/pt unknown
- 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
- 1997-08-15 AT AT97937156T patent/ATE227277T1/de not_active IP Right Cessation
- 1997-08-15 WO PCT/US1997/013934 patent/WO1998007708A1/en not_active Ceased
- 1997-08-15 DK DK97937156T patent/DK0920421T3/da active
- 1997-08-15 ES ES97937156T patent/ES2186916T3/es not_active Expired - Lifetime
- 1997-08-15 DE DE69716925T patent/DE69716925T2/de 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 |
|---|---|
| ATE227277T1 (de) | 2002-11-15 |
| US6093736A (en) | 2000-07-25 |
| PT920421E (pt) | 2003-03-31 |
| EP0920421A1 (en) | 1999-06-09 |
| AU3973697A (en) | 1998-03-06 |
| DE69716925D1 (de) | 2002-12-12 |
| WO1998007708A1 (en) | 1998-02-26 |
| ES2186916T3 (es) | 2003-05-16 |
| DK0920421T3 (da) | 2003-03-10 |
| US5990136A (en) | 1999-11-23 |
| EP0920421B1 (en) | 2002-11-06 |
| JP2000516245A (ja) | 2000-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |