AU2436600A - Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of infections - Google Patents

Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of infections Download PDF

Info

Publication number: AU2436600A
Authority: AU; Australia
Prior art keywords: methyl; dimethyl; chlorophenyl; chloro; isoxazolidinone
Prior art date: 1999-01-13
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

Application number

AU24366/00A

Other languages

English (en)

Inventor

Hassan Jomaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Jomaa Pharmaka GmbH

Original Assignee

Jomaa Pharmaka GmbH

Priority date (The priority date 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 date listed.)

1999-01-13

Filing date

2000-01-12

Publication date

2000-08-01

1999-01-30 Priority claimed from DE19903666A external-priority patent/DE19903666A1/de

2000-01-12 Application filed by Jomaa Pharmaka GmbH filed Critical Jomaa Pharmaka GmbH

2000-08-01 Publication of AU2436600A publication Critical patent/AU2436600A/en

Status Abandoned legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims description 18
208000015181 infectious disease Diseases 0.000 title claims description 10
QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 title description 7
150000002443 hydroxylamines Chemical class 0.000 title 1
-1 t-butyldimethylsilyl group Chemical group 0.000 claims description 188
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 75
241000894006 Bacteria Species 0.000 claims description 66
150000001875 compounds Chemical class 0.000 claims description 58
239000000126 substance Substances 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
244000045947 parasite Species 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 14
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 12
125000003118 aryl group Chemical group 0.000 claims description 12
241000233866 Fungi Species 0.000 claims description 9
125000000068 chlorophenyl group Chemical group 0.000 claims description 9
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
125000003277 amino group Chemical group 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
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
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
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
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
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 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
RPPFVHPKAYJEOH-UHFFFAOYSA-N 2,4,4-trimethyl-1,2-oxazolidin-3-one Chemical compound CN1OCC(C)(C)C1=O RPPFVHPKAYJEOH-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
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
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
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
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
WJRGCYNFNBPPOR-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylbutanethioamide Chemical compound OC(C(C(=S)N)(C)C)C WJRGCYNFNBPPOR-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
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
OVXXYSVFCQYBMW-UHFFFAOYSA-N 5-but-3-enoxy-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OCCC=C)ON1CC1=CC=CC=C1Cl OVXXYSVFCQYBMW-UHFFFAOYSA-N 0.000 claims description 2
VLYYUPWEEGQFIL-UHFFFAOYSA-N 5-butan-2-yloxy-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(OC(C)CC)ON1CC1=CC=CC=C1Cl VLYYUPWEEGQFIL-UHFFFAOYSA-N 0.000 claims description 2
WYJKNTLYOUZFMS-UHFFFAOYSA-N 5-chloro-2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound O=C1C(C)(C)C(Cl)ON1CC1=CC=CC=C1Cl WYJKNTLYOUZFMS-UHFFFAOYSA-N 0.000 claims description 2
241000606750 Actinobacillus Species 0.000 claims description 2
241000186046 Actinomyces Species 0.000 claims description 2
241000203716 Actinomycetaceae Species 0.000 claims description 2
241000607534 Aeromonas Species 0.000 claims description 2
241000607525 Aeromonas salmonicida Species 0.000 claims description 2
241001112741 Bacillaceae Species 0.000 claims description 2
241000193830 Bacillus <bacterium> Species 0.000 claims description 2
241000606662 Bartonellaceae Species 0.000 claims description 2
241000588807 Bordetella Species 0.000 claims description 2
241000589968 Borrelia Species 0.000 claims description 2
241000589969 Borreliella burgdorferi Species 0.000 claims description 2
241000589562 Brucella Species 0.000 claims description 2
241000589877 Campylobacter coli Species 0.000 claims description 2
241000589874 Campylobacter fetus Species 0.000 claims description 2
241000589875 Campylobacter jejuni Species 0.000 claims description 2
241001647378 Chlamydia psittaci Species 0.000 claims description 2
241000606153 Chlamydia trachomatis Species 0.000 claims description 2
241000606069 Chlamydiaceae Species 0.000 claims description 2
241000186225 Corynebacterium pseudotuberculosis Species 0.000 claims description 2
241000186427 Cutibacterium acnes Species 0.000 claims description 2
241000187831 Dermatophilus Species 0.000 claims description 2
241000588921 Enterobacteriaceae Species 0.000 claims description 2
241000194033 Enterococcus Species 0.000 claims description 2
241000588722 Escherichia Species 0.000 claims description 2
241000606790 Haemophilus Species 0.000 claims description 2
241000590002 Helicobacter pylori Species 0.000 claims description 2
241000588748 Klebsiella Species 0.000 claims description 2
241000589248 Legionella Species 0.000 claims description 2
241000589246 Legionellaceae Species 0.000 claims description 2
241000589902 Leptospira Species 0.000 claims description 2
241000589901 Leptospiraceae Species 0.000 claims description 2
241000186781 Listeria Species 0.000 claims description 2
241000186779 Listeria monocytogenes Species 0.000 claims description 2
208000016604 Lyme disease Diseases 0.000 claims description 2
201000009906 Meningitis Diseases 0.000 claims description 2
241000192017 Micrococcaceae Species 0.000 claims description 2
241000192041 Micrococcus Species 0.000 claims description 2
241000588622 Moraxella bovis Species 0.000 claims description 2
241000186360 Mycobacteriaceae Species 0.000 claims description 2
241000186359 Mycobacterium Species 0.000 claims description 2
241000186367 Mycobacterium avium Species 0.000 claims description 2
241000186366 Mycobacterium bovis Species 0.000 claims description 2
241000186362 Mycobacterium leprae Species 0.000 claims description 2
241000187479 Mycobacterium tuberculosis Species 0.000 claims description 2
241000204031 Mycoplasma Species 0.000 claims description 2
241000202934 Mycoplasma pneumoniae Species 0.000 claims description 2
241000204034 Mycoplasmataceae Species 0.000 claims description 2
241000588652 Neisseria gonorrhoeae Species 0.000 claims description 2
241000588656 Neisseriaceae Species 0.000 claims description 2
241000187654 Nocardia Species 0.000 claims description 2
241000606752 Pasteurellaceae Species 0.000 claims description 2
241000607568 Photobacterium Species 0.000 claims description 2
241000607000 Plesiomonas Species 0.000 claims description 2
241001430313 Propionibacteriaceae Species 0.000 claims description 2
241000186429 Propionibacterium Species 0.000 claims description 2
241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
241000588768 Providencia Species 0.000 claims description 2
241000947836 Pseudomonadaceae Species 0.000 claims description 2
241000589516 Pseudomonas Species 0.000 claims description 2
241000316848 Rhodococcus <scale insect> Species 0.000 claims description 2
241000606683 Rickettsiaceae Species 0.000 claims description 2
241000607142 Salmonella Species 0.000 claims description 2
241000607720 Serratia Species 0.000 claims description 2
241000607768 Shigella Species 0.000 claims description 2
241000589971 Spirochaetaceae Species 0.000 claims description 2
241000191940 Staphylococcus Species 0.000 claims description 2
241000194018 Streptococcaceae Species 0.000 claims description 2
241000194017 Streptococcus Species 0.000 claims description 2
241000589886 Treponema Species 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
241000202898 Ureaplasma Species 0.000 claims description 2
241000607598 Vibrio Species 0.000 claims description 2
241000544286 Vibrio anguillarum Species 0.000 claims description 2
241000607626 Vibrio cholerae Species 0.000 claims description 2
241000607493 Vibrionaceae Species 0.000 claims description 2
241000589634 Xanthomonas Species 0.000 claims description 2
241000607734 Yersinia <bacteria> Species 0.000 claims description 2
241000607447 Yersinia enterocolitica Species 0.000 claims description 2
241000607477 Yersinia pseudotuberculosis Species 0.000 claims description 2
241001148129 Yersinia ruckeri Species 0.000 claims description 2
CEQIXZYPNJXYTH-UHFFFAOYSA-N [(3-chloro-2,2-dimethylpropanoyl)-[(2-chlorophenyl)methyl]amino] 2-chloroacetate Chemical compound ClCC(C)(C)C(=O)N(OC(=O)CCl)CC1=CC=CC=C1Cl CEQIXZYPNJXYTH-UHFFFAOYSA-N 0.000 claims description 2
FSNPCONRFIAPJC-UHFFFAOYSA-N [(3-chloro-2,2-dimethylpropanoyl)-[(2-chlorophenyl)methyl]amino] acetate Chemical compound ClCC(C)(C)C(=O)N(OC(=O)C)CC1=CC=CC=C1Cl FSNPCONRFIAPJC-UHFFFAOYSA-N 0.000 claims description 2
RRHWDAMAYRCSTP-UHFFFAOYSA-N [(3-chloro-2,2-dimethylpropanoyl)-[(2-chlorophenyl)methyl]amino] n-methylcarbamate Chemical compound CNC(=O)ON(C(=O)C(C)(C)CCl)CC1=CC=CC=C1Cl RRHWDAMAYRCSTP-UHFFFAOYSA-N 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
FHUKASKVKWSLCY-UHFFFAOYSA-N bixlozone Chemical compound O=C1C(C)(C)CON1CC1=CC=C(Cl)C=C1Cl FHUKASKVKWSLCY-UHFFFAOYSA-N 0.000 claims description 2
230000008029 eradication Effects 0.000 claims description 2
238000000034 method Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
PIYIYBKUWPMENA-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-n,3-dihydroxy-2,2-dimethylpropanamide Chemical compound OCC(C)(C)C(=O)N(O)CC1=CC=CC=C1Cl PIYIYBKUWPMENA-UHFFFAOYSA-N 0.000 claims description 2
JZKYTHRXOHJRLM-UHFFFAOYSA-N n-benzyl-3-chloro-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)N(O)CC1=CC=CC=C1 JZKYTHRXOHJRLM-UHFFFAOYSA-N 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
241000894007 species Species 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
229940098232 yersinia enterocolitica Drugs 0.000 claims description 2
KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims 2
230000002265 prevention Effects 0.000 claims 2
GSTHDSZHKQPYGZ-UHFFFAOYSA-N (1-amino-1-oxopropan-2-yl) n-phenylcarbamate Chemical compound NC(=O)C(C)OC(=O)NC1=CC=CC=C1 GSTHDSZHKQPYGZ-UHFFFAOYSA-N 0.000 claims 1
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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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)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

AU24366/00A 1999-01-13 2000-01-12 Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of infections Abandoned AU2436600A (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE19900907		1999-01-13
DE19900907		1999-01-13
DE19903666A DE19903666A1 (de)	1999-01-13	1999-01-30	Arzneimittel mit einem Gehalt an 3-Isoxazolidinonen und Hydroxylaminsäuren als Wirkstoff und ihre Verwendung
DE19903666		1999-01-30
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
AU2436600A true AU2436600A (en)	2000-08-01

Family

ID=26051290

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU24366/00A Abandoned AU2436600A (en)	1999-01-13	2000-01-12	Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of 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)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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
US7022705B2 (en)	2001-10-25	2006-04-04	Astrazeneca Ab	Isoxazoline derivatives useful as antimicrobials
GB202209172D0 (en) *	2022-06-22	2022-08-10	Syngenta Crop Protection Ag	Improvements in or relating to organic compounds

Family Cites Families (15)

* Cited by examiner, † Cited by third party
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
EP0219923B1 (fr) *	1985-04-30	1992-09-02	Takeda Chemical Industries, Ltd.	Dérivés antibiotiques, leur préparation et leur application
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
WO1994021625A1 (fr) *	1993-03-16	1994-09-29	British Biotech Pharmaceuticals Limited	Derives d'acide hydroxamique utilises comme inhibiteurs de metalloproteinase
FI960803L (fi) *	1993-08-23	1996-04-22	Immunex Corp	TNF-alfa-sekreetion inhibiittoreita
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
AU6843298A (en) *	1997-03-28	1998-10-22	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 WO PCT/EP2000/000165 patent/WO2000041473A2/fr not_active Ceased
- 2000-01-12 PL PL00350128A patent/PL350128A1/xx not_active Application Discontinuation
- 2000-01-12 IL IL14379500A patent/IL143795A0/xx unknown
- 2000-01-12 TR TR2001/02019T patent/TR200102019T2/xx unknown
- 2000-01-12 AU AU24366/00A patent/AU2436600A/en not_active Abandoned
- 2000-01-12 EP EP00902582A patent/EP1143941A3/fr not_active Withdrawn
- 2000-01-12 BR BR0007491-8A patent/BR0007491A/pt not_active Application Discontinuation
- 2000-01-12 SK SK950-2001A patent/SK9502001A3/sk unknown
- 2000-01-12 JP JP2000593097A patent/JP2002534440A/ja active Pending
- 2000-01-12 CN CN00802779A patent/CN1342078A/zh active Pending
- 2000-01-12 HU HU0105412A patent/HUP0105412A2/hu unknown
- 2000-01-12 CZ CZ20012380A patent/CZ20012380A3/cs unknown
- 2000-01-12 CA CA002360366A patent/CA2360366A1/fr not_active Abandoned
2001
- 2001-07-12 NO NO20013464A patent/NO20013464L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2000041473A3 (fr)	2001-11-29
PL350128A1 (en)	2002-11-04
CN1342078A (zh)	2002-03-27
CA2360366A1 (fr)	2000-07-20
NO20013464D0 (no)	2001-07-12
TR200102019T2 (tr)	2002-04-22
IL143795A0 (en)	2002-04-21
WO2000041473A2 (fr)	2000-07-20
JP2002534440A (ja)	2002-10-15
SK9502001A3 (en)	2002-05-09
EP1143941A3 (fr)	2002-02-06
HUP0105412A2 (hu)	2002-05-29
EP1143941A2 (fr)	2001-10-17
CZ20012380A3 (cs)	2002-01-16
NO20013464L (no)	2001-09-12
BR0007491A (pt)	2001-11-20

Publication	Publication Date	Title
JP2002511406A (ja)	2002-04-16	感染症の治療および予防処置のための有機リン化合物の使用
US6638957B1 (en)	2003-10-28	Use of compounds with a nitrogen-oxygen heterocycle
CA2352549A1 (fr)	2000-06-02	Utilisation de derives de phosphonoformate pour traiter des infections
AU754378B2 (en)	2002-11-14	Organophosphorous compounds and the use thereof
CA2344867A1 (fr)	2000-03-30	Utilisation des derives de l'acide aminoalkylphosphonique pour la production de medicaments pour le traitement therapeutique et prophylactique dd'infections ou en tant que fongicide, bactericide ou herbicide pour vegetaux
AU2436600A (en)	2000-08-01	Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of infections
JP2002535354A (ja)	2002-10-22	感染症の予防および治療処置のための有機リン化合物の使用
AU1859100A (en)	2000-06-13	Use of phosphonoformic acid derivatives for treating infections
ZA200105007B (en)	2002-06-19	Use of 3-isoxazolidinones and hydroxylamine acids for the treatment of infections.
JP2004505011A (ja)	2004-02-19	感染治療のための有機リン化合物の使用
AU2003261554A1 (en)	2003-12-04	Organophosphorus containing preparations and applications therefor
MXPA01002979A (en)	2003-11-07	Use of organophosphorous compounds for producing medicaments for the therapeutic and prophylactic treatment of infections or as a fungicide, bactericide or herbicide for plants
CZ2001989A3 (cs)	2001-07-11	Použití fosfororganických sloučenin pro výrobu léčiv pro terapeutické a profylaktické ošetřování infekcí nebo jako fungicid, baktericid či herbicid u rostlin

Legal Events

Date	Code	Title	Description
2004-08-12	MK5	Application lapsed section 142(2)(e) - patent request and compl. specification not accepted