NO328933B1 - Peptid-deformylaseinhibitorer - Google Patents
Peptid-deformylaseinhibitorer Download PDFInfo
- Publication number
- NO328933B1 NO328933B1 NO20044186A NO20044186A NO328933B1 NO 328933 B1 NO328933 B1 NO 328933B1 NO 20044186 A NO20044186 A NO 20044186A NO 20044186 A NO20044186 A NO 20044186A NO 328933 B1 NO328933 B1 NO 328933B1
- Authority
- NO
- Norway
- Prior art keywords
- ylmethyl
- butyl
- hydroxyformamide
- dioxoimidazolidin
- group
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- RIRAIFMHHKQKAG-INIZCTEOSA-N n-[[(4s)-1-benzyl-4-butyl-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC1=CC=CC=C1 RIRAIFMHHKQKAG-INIZCTEOSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UJLWXVDZHKIFKL-KRWDZBQOSA-N n-[[(4s)-1-benzyl-2,5-dioxo-4-pentylimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCCC)(CN(O)C=O)NC(=O)N1CC1=CC=CC=C1 UJLWXVDZHKIFKL-KRWDZBQOSA-N 0.000 claims description 3
- GAUHJNXMOHNLDA-IBGZPJMESA-N n-[[(4s)-1-benzyl-4-(cyclohexylmethyl)-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound C([C@]1(CN(O)C=O)C(N(CC=2C=CC=CC=2)C(=O)N1)=O)C1CCCCC1 GAUHJNXMOHNLDA-IBGZPJMESA-N 0.000 claims description 3
- HJMQMKMIIQXBEL-INIZCTEOSA-N n-[[(4s)-4-butyl-1-[(3,4-dichlorophenyl)methyl]-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC1=CC=C(Cl)C(Cl)=C1 HJMQMKMIIQXBEL-INIZCTEOSA-N 0.000 claims description 3
- NMIIVJCMAZMYPI-KRWDZBQOSA-N n-[[(4s)-4-butyl-2,5-dioxo-1-phenacylimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC(=O)C1=CC=CC=C1 NMIIVJCMAZMYPI-KRWDZBQOSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- UOBRNYHMJUJSQJ-IBGZPJMESA-N n-[[(4s)-1,4-dibenzyl-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound C([C@]1(CN(O)C=O)C(N(CC=2C=CC=CC=2)C(=O)N1)=O)C1=CC=CC=C1 UOBRNYHMJUJSQJ-IBGZPJMESA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052614 beryl Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 101710181812 Methionine aminopeptidase Proteins 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 108010026809 Peptide deformylase Proteins 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 102100021418 Peptide deformylase, mitochondrial Human genes 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000193998 Streptococcus pneumoniae Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 229930182817 methionine Natural products 0.000 description 3
- PJOHBKYDQKOXFS-INIZCTEOSA-N n-[[(4s)-2,5-dioxo-4-pentyl-1-phenylimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCCC)(CN(O)C=O)NC(=O)N1C1=CC=CC=C1 PJOHBKYDQKOXFS-INIZCTEOSA-N 0.000 description 3
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical class ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000014616 translation Effects 0.000 description 3
- -1 (2R,4S)-4-butyl-2-tert-butyl-3-phenyloxazolidine-4-carboxylic acid methyl ester Chemical compound 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SGLTXXAPTWUPRB-QFIPXVFZSA-N n-[[(4s)-4-butyl-2,5-dioxo-1-[(4-phenylphenyl)methyl]imidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC1=CC=C(C=2C=CC=CC=2)C=C1 SGLTXXAPTWUPRB-QFIPXVFZSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 238000001243 protein synthesis Methods 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- NSSWGDHXMYAZKF-HNNXBMFYSA-N (5s)-3-benzyl-5-butyl-5-(hydroxymethyl)imidazolidine-2,4-dione Chemical compound O=C1[C@](CCCC)(CO)NC(=O)N1CC1=CC=CC=C1 NSSWGDHXMYAZKF-HNNXBMFYSA-N 0.000 description 1
- PEWFEXNVEHOOOR-QFIPXVFZSA-N (5s)-3-benzyl-5-butyl-5-(phenylmethoxyiminomethyl)imidazolidine-2,4-dione Chemical compound N([C@@](C1=O)(CCCC)C=NOCC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 PEWFEXNVEHOOOR-QFIPXVFZSA-N 0.000 description 1
- WAWKDRJMWQSRDW-HNNXBMFYSA-N (5s)-5-(hydroxymethyl)-5-pentyl-3-phenylimidazolidine-2,4-dione Chemical compound O=C1[C@](CCCCC)(CO)NC(=O)N1C1=CC=CC=C1 WAWKDRJMWQSRDW-HNNXBMFYSA-N 0.000 description 1
- VRUUBJQYIPHXNT-INIZCTEOSA-N (5s)-5-butyl-5-(hydroxymethyl)-3-phenacylimidazolidine-2,4-dione Chemical compound O=C1[C@](CCCC)(CO)NC(=O)N1CC(=O)C1=CC=CC=C1 VRUUBJQYIPHXNT-INIZCTEOSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- QFMMGEUCSNAKAD-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)acetamide Chemical compound NC(=O)CC1=CC(Cl)=CC(Cl)=C1 QFMMGEUCSNAKAD-UHFFFAOYSA-N 0.000 description 1
- CKFDLRMIOKJQLB-KRWDZBQOSA-N 2-[(4s)-4-butyl-4-[[formyl(hydroxy)amino]methyl]-2,5-dioxoimidazolidin-1-yl]-n-(3,5-dichlorophenyl)acetamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC(=O)NC1=CC(Cl)=CC(Cl)=C1 CKFDLRMIOKJQLB-KRWDZBQOSA-N 0.000 description 1
- YSBCDCRERWTSPG-KRWDZBQOSA-N 2-[[(4s)-4-butyl-4-[[formyl(hydroxy)amino]methyl]-2,5-dioxoimidazolidin-1-yl]methyl]benzoic acid Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC1=CC=CC=C1C(O)=O YSBCDCRERWTSPG-KRWDZBQOSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 108020005133 Chloroplast RNA Proteins 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 101100072702 Drosophila melanogaster defl gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000698 Formate Dehydrogenases Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 108010072462 Hydroxymethyl and Formyl Transferases Proteins 0.000 description 1
- 102000006933 Hydroxymethyl and Formyl Transferases Human genes 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 241000588655 Moraxella catarrhalis Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PYUSHNKNPOHWEZ-YFKPBYRVSA-N N-formyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC=O PYUSHNKNPOHWEZ-YFKPBYRVSA-N 0.000 description 1
- 125000003001 N-formyl-L-methionyl group Chemical group O=C([H])N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])SC([H])([H])[H] 0.000 description 1
- 101150017629 PDF gene Proteins 0.000 description 1
- 108010064851 Plant Proteins Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- KPKDCJWDDPLVRF-UHFFFAOYSA-N [(2-methylpropan-2-yl)oxycarbonylamino] 2-tert-butylperoxy-2-oxoacetate Chemical compound CC(C)(C)OOC(=O)C(=O)ONC(=O)OC(C)(C)C KPKDCJWDDPLVRF-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000002802 antimicrobial activity assay Methods 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000003763 chloroplast Anatomy 0.000 description 1
- 230000011088 chloroplast localization Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000014304 histidine Nutrition 0.000 description 1
- 150000002411 histidines Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
- 108010057757 methionyl-tRNA formyltransferase Proteins 0.000 description 1
- CUOGQSHIYFHDEM-IONNQARKSA-N methyl (2r,4s)-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate Chemical compound COC(=O)[C@@H]1CO[C@H](C(C)(C)C)N1C=O CUOGQSHIYFHDEM-IONNQARKSA-N 0.000 description 1
- ANSUDRATXSJBLY-VKHMYHEASA-N methyl (2s)-2-amino-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](N)CO ANSUDRATXSJBLY-VKHMYHEASA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- GIILUZLSDNTVQT-IBGZPJMESA-N n-[[(4s)-1-[2-(1-benzofuran-2-yl)-2-oxoethyl]-4-butyl-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CC(=O)C1=CC2=CC=CC=C2O1 GIILUZLSDNTVQT-IBGZPJMESA-N 0.000 description 1
- WKRHYPNQUMKSBC-HNNXBMFYSA-N n-[[(4s)-4-butyl-1-(2-morpholin-4-ylethyl)-2,5-dioxoimidazolidin-4-yl]methyl]-n-hydroxyformamide Chemical compound O=C1[C@](CCCC)(CN(O)C=O)NC(=O)N1CCN1CCOCC1 WKRHYPNQUMKSBC-HNNXBMFYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000081 peptide deformylase inhibitor Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36442302P | 2002-03-13 | 2002-03-13 | |
| PCT/US2003/007509 WO2003077913A1 (en) | 2002-03-13 | 2003-03-13 | Peptide deformylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20044186L NO20044186L (no) | 2004-09-30 |
| NO328933B1 true NO328933B1 (no) | 2010-06-21 |
Family
ID=28041913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20044186A NO328933B1 (no) | 2002-03-13 | 2004-09-30 | Peptid-deformylaseinhibitorer |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20050124677A1 (ru) |
| EP (1) | EP1482930B1 (ru) |
| JP (1) | JP4471663B2 (ru) |
| KR (1) | KR100980145B1 (ru) |
| CN (1) | CN100336809C (ru) |
| AT (1) | ATE514683T1 (ru) |
| AU (1) | AU2003216554A1 (ru) |
| BR (1) | BR0308321A (ru) |
| CA (1) | CA2478331A1 (ru) |
| ES (1) | ES2366396T3 (ru) |
| IL (1) | IL163899A0 (ru) |
| IS (1) | IS7441A (ru) |
| MX (1) | MXPA04008799A (ru) |
| NO (1) | NO328933B1 (ru) |
| NZ (1) | NZ534839A (ru) |
| PL (1) | PL371016A1 (ru) |
| RU (1) | RU2287525C2 (ru) |
| TW (1) | TWI294778B (ru) |
| WO (1) | WO2003077913A1 (ru) |
| ZA (1) | ZA200406973B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7208595B2 (en) * | 2003-07-25 | 2007-04-24 | The Ohio State University Research Foundation | Peptide deformylase inhibitors as novel antibiotics |
| US7705037B2 (en) * | 2005-06-07 | 2010-04-27 | Novartis Ag | 1-substituted pyrrolidin-2-ones and use thereof as peptide deformylase inhibitors |
| NZ583350A (en) * | 2007-08-21 | 2012-03-30 | Senomyx Inc | Heteroaryl-hydantoin derivatives as bitter taste inhibitors |
| DE102009045969B4 (de) * | 2009-10-23 | 2019-01-31 | Technische Universität Bergakademie Freiberg | Verfahren und Mittel zur Spaltung von Estern, Amiden und Thioestern der Ameisensäure |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
| EP0816341A1 (de) * | 1996-07-04 | 1998-01-07 | F. Hoffmann-La Roche Ag | Verfahren zur Herstellung von chiralen Bernsteinsäurederivaten |
| WO2000059285A2 (en) * | 1999-04-02 | 2000-10-12 | Du Pont Pharmaceuticals Company | NOVEL LACTAM INHIBITORS OF MATRIX METALLOPROTEINASES, TNF-α, AND AGGRECANASE |
| WO2002028829A2 (en) | 2000-09-25 | 2002-04-11 | Questcor Pharmaceuticals, Inc. | Peptide deformylase inhibitors |
| WO2002055516A2 (en) * | 2001-01-11 | 2002-07-18 | Bristol Myers Squibb Co | 1,1-DISUBSTITUTED CYCLIC INHIBITORS OF MATRIX METALLOPROTEASE AND TNF-$g(a) |
-
2003
- 2003-03-11 TW TW092105141A patent/TWI294778B/zh not_active IP Right Cessation
- 2003-03-12 NZ NZ534839A patent/NZ534839A/en not_active IP Right Cessation
- 2003-03-12 RU RU2004130454/04A patent/RU2287525C2/ru not_active IP Right Cessation
- 2003-03-12 CN CNB038106507A patent/CN100336809C/zh not_active Expired - Fee Related
- 2003-03-12 AT AT03744644T patent/ATE514683T1/de not_active IP Right Cessation
- 2003-03-12 CA CA002478331A patent/CA2478331A1/en not_active Abandoned
- 2003-03-12 JP JP2003575966A patent/JP4471663B2/ja not_active Expired - Fee Related
- 2003-03-12 AU AU2003216554A patent/AU2003216554A1/en not_active Abandoned
- 2003-03-12 US US10/507,510 patent/US20050124677A1/en not_active Abandoned
- 2003-03-12 EP EP03744644A patent/EP1482930B1/en not_active Expired - Lifetime
- 2003-03-12 ES ES03744644T patent/ES2366396T3/es not_active Expired - Lifetime
- 2003-03-12 PL PL03371016A patent/PL371016A1/xx not_active Application Discontinuation
- 2003-03-13 BR BR0308321-7A patent/BR0308321A/pt not_active IP Right Cessation
- 2003-03-13 KR KR1020047014184A patent/KR100980145B1/ko not_active IP Right Cessation
- 2003-03-13 WO PCT/US2003/007509 patent/WO2003077913A1/en active Application Filing
- 2003-03-13 MX MXPA04008799A patent/MXPA04008799A/es active IP Right Grant
- 2003-03-13 IL IL16389903A patent/IL163899A0/xx unknown
-
2004
- 2004-09-01 ZA ZA200406973A patent/ZA200406973B/en unknown
- 2004-09-08 IS IS7441A patent/IS7441A/is unknown
- 2004-09-30 NO NO20044186A patent/NO328933B1/no not_active IP Right Cessation
-
2007
- 2007-02-16 US US11/675,788 patent/US7745637B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TWI294778B (en) | 2008-03-21 |
| EP1482930A4 (en) | 2006-06-28 |
| PL371016A1 (en) | 2005-06-13 |
| BR0308321A (pt) | 2004-12-28 |
| IS7441A (is) | 2004-09-08 |
| US20050124677A1 (en) | 2005-06-09 |
| NO20044186L (no) | 2004-09-30 |
| EP1482930A1 (en) | 2004-12-08 |
| US20070155810A1 (en) | 2007-07-05 |
| TW200405810A (en) | 2004-04-16 |
| ZA200406973B (en) | 2005-06-23 |
| WO2003077913A1 (en) | 2003-09-25 |
| EP1482930B1 (en) | 2011-06-29 |
| JP4471663B2 (ja) | 2010-06-02 |
| IL163899A0 (en) | 2005-12-18 |
| RU2004130454A (ru) | 2005-04-10 |
| CN1652775A (zh) | 2005-08-10 |
| RU2287525C2 (ru) | 2006-11-20 |
| NZ534839A (en) | 2006-09-29 |
| JP2005525383A (ja) | 2005-08-25 |
| ES2366396T3 (es) | 2011-10-19 |
| US7745637B2 (en) | 2010-06-29 |
| ATE514683T1 (de) | 2011-07-15 |
| CN100336809C (zh) | 2007-09-12 |
| KR100980145B1 (ko) | 2010-09-03 |
| MXPA04008799A (es) | 2004-11-26 |
| KR20040091120A (ko) | 2004-10-27 |
| CA2478331A1 (en) | 2003-09-25 |
| AU2003216554A1 (en) | 2003-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20060211603A1 (en) | Ramoplanin derivatives possessing antibacterial activity | |
| US7745637B2 (en) | Peptide deformylase inhibitors | |
| US20040192719A1 (en) | Peptide deformylase inhibitors | |
| EP1370258B1 (en) | Peptide deformylase inhibitors | |
| US6797730B2 (en) | Peptide deformylase inhibitors | |
| US6897233B2 (en) | Peptide deformylase inhibitors | |
| US7456211B2 (en) | Peptide deformylase inhibitors | |
| EP1515956A1 (en) | Peptide deformylase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |