JP2000516245A - 抗菌剤として有用なイソオキサゾリン誘導体類 - Google Patents
抗菌剤として有用なイソオキサゾリン誘導体類Info
- Publication number
- JP2000516245A JP2000516245A JP10510781A JP51078198A JP2000516245A JP 2000516245 A JP2000516245 A JP 2000516245A JP 10510781 A JP10510781 A JP 10510781A JP 51078198 A JP51078198 A JP 51078198A JP 2000516245 A JP2000516245 A JP 2000516245A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dihydro
- phenyl
- methyl
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 8
- 150000002547 isoxazolines Chemical class 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- -1 Phenyl Chemical group 0.000 claims description 157
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 126
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 102
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 5
- 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 5
- 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 5
- 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 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
- TVCVZPPTRJJNOP-UHFFFAOYSA-N 1,2-dihydropyridine-2-carboxylic acid Chemical compound OC(=O)C1NC=CC=C1 TVCVZPPTRJJNOP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229940047583 cetamide Drugs 0.000 claims description 4
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 4
- 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 4
- 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 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 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 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 claims description 2
- ZKZBRRZVXBPEBD-UHFFFAOYSA-N N-[[3-[3-fluoro-4-(1-formylazetidin-3-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CN(C3)C=O)=CC=2)=N1 ZKZBRRZVXBPEBD-UHFFFAOYSA-N 0.000 claims description 2
- YHNCSISJJATYPL-UHFFFAOYSA-N N-[[3-[3-fluoro-4-(1-formylpyrrolidin-3-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]acetamide Chemical compound O1C(CNC(=O)C)CC(C=2C=C(F)C(C3CN(CC3)C=O)=CC=2)=N1 YHNCSISJJATYPL-UHFFFAOYSA-N 0.000 claims description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000014676 Phragmites communis Nutrition 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 208000015181 infectious disease Diseases 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
- 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 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
- 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
- WITIBJZLZRVFIL-UHFFFAOYSA-N n-[[3-[3-fluoro-4-[1-(4-oxo-1,3-thiazol-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=3SCC(=O)N=3)=CC=2)=N1 WITIBJZLZRVFIL-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 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
- QKDVKHUQBUEZOU-UHFFFAOYSA-N n-[[3-[4-[1-(4-oxo-1,3-thiazol-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=2SCC(=O)N=2)=N1 QKDVKHUQBUEZOU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 10
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000005936 piperidyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical group OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 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 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000002904 solvent Substances 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
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012074 organic phase Substances 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
- 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 6
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 238000006352 cycloaddition reaction Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2428796P | 1996-08-21 | 1996-08-21 | |
| US60/024,287 | 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 |
|---|---|
| JP2000516245A true JP2000516245A (ja) | 2000-12-05 |
| JP2000516245A5 JP2000516245A5 (enExample) | 2005-04-07 |
Family
ID=21819822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10510781A Withdrawn JP2000516245A (ja) | 1996-08-21 | 1997-08-15 | 抗菌剤として有用なイソオキサゾリン誘導体類 |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013532719A (ja) * | 2010-08-05 | 2013-08-19 | ゾエティス・エルエルシー | 駆虫剤としてのイソオキサゾリン誘導体 |
| JP2022530709A (ja) * | 2019-07-03 | 2022-06-30 | メルク・シャープ・アンド・ドーム・コーポレーション | 抗菌薬としての化合物及びその使用 |
Families Citing this family (28)
| 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 |
| 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 |
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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013532719A (ja) * | 2010-08-05 | 2013-08-19 | ゾエティス・エルエルシー | 駆虫剤としてのイソオキサゾリン誘導体 |
| JP2022530709A (ja) * | 2019-07-03 | 2022-06-30 | メルク・シャープ・アンド・ドーム・コーポレーション | 抗菌薬としての化合物及びその使用 |
| JP7183455B2 (ja) | 2019-07-03 | 2022-12-05 | メルク・シャープ・アンド・ドーム・エルエルシー | 抗菌薬としての化合物及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0920421A1 (en) | 1999-06-09 |
| DE69716925T2 (de) | 2003-09-11 |
| 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 |
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