CA2360366A1 - Utilisation de 3-isoxazolidinones et d'hydroxylaminoacides pour le traitement d'infections - Google Patents
Utilisation de 3-isoxazolidinones et d'hydroxylaminoacides pour le traitement d'infections Download PDFInfo
- Publication number
- CA2360366A1 CA2360366A1 CA002360366A CA2360366A CA2360366A1 CA 2360366 A1 CA2360366 A1 CA 2360366A1 CA 002360366 A CA002360366 A CA 002360366A CA 2360366 A CA2360366 A CA 2360366A CA 2360366 A1 CA2360366 A1 CA 2360366A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- dimethyl
- chlorophenyl
- chloro
- isoxazolidinone
- 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.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims description 19
- 208000015181 infectious disease Diseases 0.000 title claims description 11
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 title description 5
- 150000002443 hydroxylamines Chemical class 0.000 title 1
- 150000001875 compounds Chemical group 0.000 claims abstract description 61
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 203
- 241000894006 Bacteria Species 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 244000045947 parasite Species 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 201000004792 malaria Diseases 0.000 claims description 5
- 241000193403 Clostridium Species 0.000 claims description 4
- 241000186216 Corynebacterium Species 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 241000589989 Helicobacter Species 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241000588653 Neisseria Species 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 241000607534 Aeromonas Species 0.000 claims description 3
- 208000000230 African Trypanosomiasis Diseases 0.000 claims description 3
- 206010001986 Amoebic dysentery Diseases 0.000 claims description 3
- 241000589876 Campylobacter Species 0.000 claims description 3
- 208000003495 Coccidiosis Diseases 0.000 claims description 3
- 208000008953 Cryptosporidiosis Diseases 0.000 claims description 3
- 206010011502 Cryptosporidiosis infection Diseases 0.000 claims description 3
- 206010023076 Isosporiasis Diseases 0.000 claims description 3
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 3
- 208000004554 Leishmaniasis Diseases 0.000 claims description 3
- 241000588621 Moraxella Species 0.000 claims description 3
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 claims description 3
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 claims description 3
- 208000006775 Sarcocystosis Diseases 0.000 claims description 3
- 201000005485 Toxoplasmosis Diseases 0.000 claims description 3
- 208000005448 Trichomonas Infections Diseases 0.000 claims description 3
- 206010044620 Trichomoniasis Diseases 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 208000007456 balantidiasis Diseases 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 201000006592 giardiasis Diseases 0.000 claims description 3
- 208000029080 human African trypanosomiasis Diseases 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 244000052769 pathogen Species 0.000 claims description 3
- 201000000317 pneumocystosis Diseases 0.000 claims description 3
- 201000002612 sleeping sickness Diseases 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims description 2
- XPLAOPDRQZQLDW-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(F)C=C1F XPLAOPDRQZQLDW-UHFFFAOYSA-N 0.000 claims description 2
- ZTMOLOVAQWCURR-UHFFFAOYSA-N 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(Cl)=CC=C1Cl ZTMOLOVAQWCURR-UHFFFAOYSA-N 0.000 claims description 2
- XPXZSOWIHDVVDU-UHFFFAOYSA-N 2-[(2-bromo-4-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(F)C=C1Br XPXZSOWIHDVVDU-UHFFFAOYSA-N 0.000 claims description 2
- YQPIKUDPKJDPHS-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Br YQPIKUDPKJDPHS-UHFFFAOYSA-N 0.000 claims description 2
- VUGAGFDYOGGZQW-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-5-chloro-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(Cl)ON1CC1=CC=CC=C1Br VUGAGFDYOGGZQW-UHFFFAOYSA-N 0.000 claims description 2
- XRQDYLGWKVMPCH-UHFFFAOYSA-N 2-[(2-chloro-4-methoxyphenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound ClC1=CC(OC)=CC=C1CN1C(=O)C(C)(C)CO1 XRQDYLGWKVMPCH-UHFFFAOYSA-N 0.000 claims description 2
- LIGJLLLFKITYIY-UHFFFAOYSA-N 2-[(2-chloro-5-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(F)=CC=C1Cl LIGJLLLFKITYIY-UHFFFAOYSA-N 0.000 claims description 2
- LGEFDLILYZYQOK-UHFFFAOYSA-N 2-[(2-chloro-5-methoxyphenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound COC1=CC=C(Cl)C(CN2C(C(C)(C)CO2)=O)=C1 LGEFDLILYZYQOK-UHFFFAOYSA-N 0.000 claims description 2
- KMCVRANMVXCYQW-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=C(F)C=CC=C1Cl KMCVRANMVXCYQW-UHFFFAOYSA-N 0.000 claims description 2
- KQLPIFSABCVSDV-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-(3-methylbut-3-enoxy)-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCC(=C)C)ON1CC1=CC=CC=C1Cl KQLPIFSABCVSDV-UHFFFAOYSA-N 0.000 claims description 2
- QGWXZNNRJWBKCM-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-pentoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCCCC)ON1CC1=CC=CC=C1Cl QGWXZNNRJWBKCM-UHFFFAOYSA-N 0.000 claims description 2
- DENWPYVXRADMNG-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-phenoxy-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1OC1=CC=CC=C1 DENWPYVXRADMNG-UHFFFAOYSA-N 0.000 claims description 2
- IXEKXPSCCDIZFF-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-phenylmethoxy-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1OCC1=CC=CC=C1 IXEKXPSCCDIZFF-UHFFFAOYSA-N 0.000 claims description 2
- FJFRVNKWPLREDS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-propan-2-yloxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OC(C)C)ON1CC1=CC=CC=C1Cl FJFRVNKWPLREDS-UHFFFAOYSA-N 0.000 claims description 2
- WMKOKZDCJOJNEL-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-5-propoxy-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCC)ON1CC1=CC=CC=C1Cl WMKOKZDCJOJNEL-UHFFFAOYSA-N 0.000 claims description 2
- OOPRQLRDWZCIHG-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-(2-methoxyethoxy)-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCOC)ON1CC1=CC=CC=C1Cl OOPRQLRDWZCIHG-UHFFFAOYSA-N 0.000 claims description 2
- DVYVYQGHBXLBNB-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-cyclopentyloxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1OC1CCCC1 DVYVYQGHBXLBNB-UHFFFAOYSA-N 0.000 claims description 2
- ASGSCGAJFYIXOJ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-ethoxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCC)ON1CC1=CC=CC=C1Cl ASGSCGAJFYIXOJ-UHFFFAOYSA-N 0.000 claims description 2
- CVKBVXIBJOVFMS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-hexoxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCCCCC)ON1CC1=CC=CC=C1Cl CVKBVXIBJOVFMS-UHFFFAOYSA-N 0.000 claims description 2
- MDZOMCCXUBFSBT-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-hydroxy-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(O)ON1CC1=CC=CC=C1Cl MDZOMCCXUBFSBT-UHFFFAOYSA-N 0.000 claims description 2
- OSEIFEMBMMQYPR-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C(Cl)=C1 OSEIFEMBMMQYPR-UHFFFAOYSA-N 0.000 claims description 2
- FETSJLMCIHGQTG-UHFFFAOYSA-N 2-[(4-bromo-2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Br)C=C1Cl FETSJLMCIHGQTG-UHFFFAOYSA-N 0.000 claims description 2
- XDJDFJFLEIEKIF-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C=C1 XDJDFJFLEIEKIF-UHFFFAOYSA-N 0.000 claims description 2
- BXKAQBOFZXUEQK-UHFFFAOYSA-N 2-[(4-fluoro-2-iodophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC=C(F)C=C1I BXKAQBOFZXUEQK-UHFFFAOYSA-N 0.000 claims description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- RQTWOIBDPIJMND-UHFFFAOYSA-N 3-bromo-n-[(2-bromophenyl)methyl]-n-hydroxy-2,2-dimethylpropanamide Chemical compound BrCC(C)(C)C(=O)N(O)CC1=CC=CC=C1Br RQTWOIBDPIJMND-UHFFFAOYSA-N 0.000 claims description 2
- SDQDJSJXPJPIBQ-UHFFFAOYSA-N 3-chloro-4-[(4,4-dimethyl-3-oxo-1,2-oxazolidin-2-yl)methyl]benzonitrile Chemical compound O=C1C(C)(C)CON1CC1=CC=C(C#N)C=C1Cl SDQDJSJXPJPIBQ-UHFFFAOYSA-N 0.000 claims description 2
- NIEBYXBPASQMET-UHFFFAOYSA-N 3-chloro-n-[(2,4-dichlorophenyl)methyl]-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)CC1=CC=C(Cl)C=C1Cl NIEBYXBPASQMET-UHFFFAOYSA-N 0.000 claims description 2
- ZGBBCGIQIYTCEV-UHFFFAOYSA-N 3-chloro-n-[(2-chlorophenyl)methyl]-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)CC1=CC=CC=C1Cl ZGBBCGIQIYTCEV-UHFFFAOYSA-N 0.000 claims description 2
- YSYWVPRIQDHPAU-UHFFFAOYSA-N 3-chloro-n-[(2-chlorophenyl)methyl]-n-methoxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(OC)CC1=CC=CC=C1Cl YSYWVPRIQDHPAU-UHFFFAOYSA-N 0.000 claims description 2
- MLOLDVZNRHOUAY-UHFFFAOYSA-N 3-chloro-n-[(2-fluorophenyl)methyl]-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)CC1=CC=CC=C1F MLOLDVZNRHOUAY-UHFFFAOYSA-N 0.000 claims description 2
- QWQDXMNZBZANEB-UHFFFAOYSA-N 3-chloro-n-hydroxy-2,2-dimethyl-n-[(2-methylphenyl)methyl]propanamide Chemical compound CC1=CC=CC=C1CN(O)C(=O)C(C)(C)CCl QWQDXMNZBZANEB-UHFFFAOYSA-N 0.000 claims description 2
- TVIRPTGZIJUNGS-UHFFFAOYSA-N 3-chloro-n-hydroxy-2,2-dimethyl-n-phenylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)C1=CC=CC=C1 TVIRPTGZIJUNGS-UHFFFAOYSA-N 0.000 claims description 2
- XZRQUDHPTBDXRO-UHFFFAOYSA-N 4,4-dimethyl-2-[(2,4,5-trichlorophenyl)methyl]-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1CC1=CC(Cl)=C(Cl)C=C1Cl XZRQUDHPTBDXRO-UHFFFAOYSA-N 0.000 claims description 2
- MFCVJVSUKRTRFE-UHFFFAOYSA-N 4,4-dimethyl-2-[(2-methylphenyl)methyl]-1,2-oxazolidin-3-one Chemical compound CC1=CC=CC=C1CN1C(=O)C(C)(C)CO1 MFCVJVSUKRTRFE-UHFFFAOYSA-N 0.000 claims description 2
- UEUTYYINEWCCOV-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)CON1C1=CC=CC=C1 UEUTYYINEWCCOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- IMSRJPMLEXEDMH-UHFFFAOYSA-N 5-anilino-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O1N(CC=2C(=CC=CC=2)Cl)C(=O)C(C)(C)C1NC1=CC=CC=C1 IMSRJPMLEXEDMH-UHFFFAOYSA-N 0.000 claims description 2
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- 229930101283 tetracycline Natural products 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960003962 trifluridine Drugs 0.000 description 1
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
- 229960003281 tyrothricin Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) 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)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
L'invention concerne des médicaments contenant au moins un composé de formule générale (I), ainsi que leur utilisation pour le traitement thérapeutique et prophylactique d'infections chez l'homme et chez les animaux, provoquées par des bactéries, champignons et parasites.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19900907 | 1999-01-13 | ||
| DE19900907.4 | 1999-01-13 | ||
| DE19903666.7 | 1999-01-30 | ||
| DE19903666A DE19903666A1 (de) | 1999-01-13 | 1999-01-30 | Arzneimittel mit einem Gehalt an 3-Isoxazolidinonen und Hydroxylaminsäuren als Wirkstoff und ihre Verwendung |
| PCT/EP2000/000165 WO2000041473A2 (fr) | 1999-01-13 | 2000-01-12 | Utilisation de 3-isoxazolidinones et d'hydroxylaminoacides pour le traitement d'infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2360366A1 true CA2360366A1 (fr) | 2000-07-20 |
Family
ID=26051290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002360366A Abandoned CA2360366A1 (fr) | 1999-01-13 | 2000-01-12 | Utilisation de 3-isoxazolidinones et d'hydroxylaminoacides pour le traitement d'infections |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1143941A3 (fr) |
| JP (1) | JP2002534440A (fr) |
| CN (1) | CN1342078A (fr) |
| AU (1) | AU2436600A (fr) |
| BR (1) | BR0007491A (fr) |
| CA (1) | CA2360366A1 (fr) |
| CZ (1) | CZ20012380A3 (fr) |
| HU (1) | HUP0105412A2 (fr) |
| IL (1) | IL143795A0 (fr) |
| NO (1) | NO20013464L (fr) |
| PL (1) | PL350128A1 (fr) |
| SK (1) | SK9502001A3 (fr) |
| TR (1) | TR200102019T2 (fr) |
| WO (1) | WO2000041473A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023247301A1 (fr) * | 2022-06-22 | 2023-12-28 | Syngenta Crop Protection Ag | Composes herbicides |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| EP1443930A1 (fr) | 2001-10-25 | 2004-08-11 | AstraZeneca AB | Derives d'isoxazoline utilises en tant qu'agents antimicrobiens |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL45174A (en) * | 1973-08-10 | 1976-12-31 | Merck & Co Inc | Antibacterial preparations containing a compound of the type 3-fluoro-D-alanine and a cyclocarrin compound that is converted in the nitrogen atom |
| US3911007A (en) * | 1974-08-08 | 1975-10-07 | Searle & Co | N-substituted N-benzyloxy-2-methyl-2-(4-halophenoxy)propionamides |
| FR2290442A1 (fr) * | 1974-11-06 | 1976-06-04 | Aries Robert | Nouvelles rifamycines |
| DE3686632T2 (de) * | 1985-04-30 | 1993-01-21 | Takeda Chemical Industries Ltd | Antibiotische derivate, ihre herstellung und verwendung. |
| GB8531838D0 (en) * | 1985-12-30 | 1986-02-05 | Wellcome Found | Aryl derivatives |
| JPS63119462A (ja) * | 1986-11-05 | 1988-05-24 | Takeda Chem Ind Ltd | 五員環n−スルホ化合物 |
| JPS63119476A (ja) * | 1986-11-05 | 1988-05-24 | Takeda Chem Ind Ltd | イソキサゾリドン誘導体 |
| US5288896A (en) * | 1992-01-15 | 1994-02-22 | Warner-Lambert Company | 3,5-di-t-butyl-4-hydroxylphenylmethylhydroxylamines and their derivatives, pharmaceutical compositions, and methods of use therefor |
| ATE169621T1 (de) * | 1993-03-16 | 1998-08-15 | British Biotech Pharm | Hydroxamsaeurederivate als metalloproteinase inhibitoren |
| NZ271893A (en) * | 1993-08-23 | 1997-11-24 | Immunex Corp | Inhibitors of tnf-alpha secretion |
| GB9401129D0 (en) * | 1994-01-21 | 1994-03-16 | British Bio Technology | Hydroxamic acid derivatives as metalloproteinase inhibitors |
| WO1996013263A2 (fr) * | 1994-11-01 | 1996-05-09 | Research Corporation Technologies, Inc. | Methodes de traitement de maladies virales par des inhibiteurs de la biosynthese des sphingolipides |
| US5919790A (en) * | 1996-10-11 | 1999-07-06 | Warner-Lambert Company | Hydroxamate inhibitors of interleukin-1β converting enzyme |
| US6251913B1 (en) * | 1997-03-28 | 2001-06-26 | Zeneca Limited | Hydroxamic acids substituted by heterocycles useful for inhibition of tumor necrosis factor |
| AUPO721997A0 (en) * | 1997-06-06 | 1997-07-03 | Queensland Institute Of Medical Research, The | Anticancer compounds |
-
2000
- 2000-01-12 PL PL00350128A patent/PL350128A1/xx not_active Application Discontinuation
- 2000-01-12 SK SK950-2001A patent/SK9502001A3/sk unknown
- 2000-01-12 WO PCT/EP2000/000165 patent/WO2000041473A2/fr not_active Ceased
- 2000-01-12 CZ CZ20012380A patent/CZ20012380A3/cs unknown
- 2000-01-12 IL IL14379500A patent/IL143795A0/xx unknown
- 2000-01-12 HU HU0105412A patent/HUP0105412A2/hu unknown
- 2000-01-12 TR TR2001/02019T patent/TR200102019T2/xx unknown
- 2000-01-12 JP JP2000593097A patent/JP2002534440A/ja active Pending
- 2000-01-12 CA CA002360366A patent/CA2360366A1/fr not_active Abandoned
- 2000-01-12 CN CN00802779A patent/CN1342078A/zh active Pending
- 2000-01-12 EP EP00902582A patent/EP1143941A3/fr not_active Withdrawn
- 2000-01-12 AU AU24366/00A patent/AU2436600A/en not_active Abandoned
- 2000-01-12 BR BR0007491-8A patent/BR0007491A/pt not_active Application Discontinuation
-
2001
- 2001-07-12 NO NO20013464A patent/NO20013464L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023247301A1 (fr) * | 2022-06-22 | 2023-12-28 | Syngenta Crop Protection Ag | Composes herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1342078A (zh) | 2002-03-27 |
| HUP0105412A2 (hu) | 2002-05-29 |
| EP1143941A2 (fr) | 2001-10-17 |
| BR0007491A (pt) | 2001-11-20 |
| NO20013464D0 (no) | 2001-07-12 |
| TR200102019T2 (tr) | 2002-04-22 |
| WO2000041473A2 (fr) | 2000-07-20 |
| EP1143941A3 (fr) | 2002-02-06 |
| AU2436600A (en) | 2000-08-01 |
| PL350128A1 (en) | 2002-11-04 |
| SK9502001A3 (en) | 2002-05-09 |
| JP2002534440A (ja) | 2002-10-15 |
| CZ20012380A3 (cs) | 2002-01-16 |
| IL143795A0 (en) | 2002-04-21 |
| NO20013464L (no) | 2001-09-12 |
| WO2000041473A3 (fr) | 2001-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |