DE60019954T2 - Fab i hemmer - Google Patents
Fab i hemmer Download PDFInfo
- Publication number
- DE60019954T2 DE60019954T2 DE60019954T DE60019954T DE60019954T2 DE 60019954 T2 DE60019954 T2 DE 60019954T2 DE 60019954 T DE60019954 T DE 60019954T DE 60019954 T DE60019954 T DE 60019954T DE 60019954 T2 DE60019954 T2 DE 60019954T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- alkyl
- amino
- phenyl
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 33
- -1 2-amino-5- {N-methyl-N - [(1-methylindol-2-yl) methyl] carbamoyl} phenyl Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 14
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- WYOGULYJJIXRCP-UHFFFAOYSA-N 3-[(n-acetylanilino)methyl]-4-amino-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C=1C2=CC=CC=C2N(C)C=1CN(C)C(=O)C(C=1)=CC=C(N)C=1CN(C(C)=O)C1=CC=CC=C1 WYOGULYJJIXRCP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- AWTBJNJPBKTHEV-UHFFFAOYSA-N 3-[(acetyl-methyl-amino)-methyl]-4-amino-n-methyl-n-(1-methyl-1h-indol-2-ylmethyl)-benzamide Chemical compound C=1C2=CC=CC=C2N(C)C=1CN(C)C(=O)C1=CC=C(N)C(CN(C)C(C)=O)=C1 AWTBJNJPBKTHEV-UHFFFAOYSA-N 0.000 claims description 3
- QVQNIGLHOQOTTI-UHFFFAOYSA-N 3-[(n-acetyl-4-hydroxyanilino)methyl]-4-amino-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C=1C2=CC=CC=C2N(C)C=1CN(C)C(=O)C(C=1)=CC=C(N)C=1CN(C(C)=O)C1=CC=C(O)C=C1 QVQNIGLHOQOTTI-UHFFFAOYSA-N 0.000 claims description 3
- VGDMSHISMQWLKD-UHFFFAOYSA-N 3-[[acetyl(ethoxy)amino]methyl]-4-amino-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C1=C(N)C(CN(OCC)C(C)=O)=CC(C(=O)N(C)CC=2N(C3=CC=CC=C3C=2)C)=C1 VGDMSHISMQWLKD-UHFFFAOYSA-N 0.000 claims description 3
- PIHVXOGXPFFNHK-UHFFFAOYSA-N 3-[[acetyl(methyl)amino]methyl]-4-amino-n-methyl-n-[(1-methylindol-3-yl)methyl]benzamide Chemical compound C=1N(C)C2=CC=CC=C2C=1CN(C)C(=O)C1=CC=C(N)C(CN(C)C(C)=O)=C1 PIHVXOGXPFFNHK-UHFFFAOYSA-N 0.000 claims description 3
- ZSKFNLKQCSUJHZ-UHFFFAOYSA-N 4-amino-3-[[(2-cyclopentylacetyl)-methylamino]methyl]-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C=1C2=CC=CC=C2N(C)C=1CN(C)C(=O)C(C=1)=CC=C(N)C=1CN(C)C(=O)CC1CCCC1 ZSKFNLKQCSUJHZ-UHFFFAOYSA-N 0.000 claims description 3
- WJTDJBFUPIXKDK-UHFFFAOYSA-N 4-amino-3-[[(2-hydroxy-4-methylpentanoyl)-methylamino]methyl]-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C1=C(N)C(CN(C)C(=O)C(O)CC(C)C)=CC(C(=O)N(C)CC=2N(C3=CC=CC=C3C=2)C)=C1 WJTDJBFUPIXKDK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 2
- LAZCTCAVDMHWTQ-UHFFFAOYSA-N 4-amino-3-[[(2-hydroxyacetyl)-methylamino]methyl]-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C1=C(N)C(CN(C)C(=O)CO)=CC(C(=O)N(C)CC=2N(C3=CC=CC=C3C=2)C)=C1 LAZCTCAVDMHWTQ-UHFFFAOYSA-N 0.000 claims description 2
- QVWXEBZTEMIIMU-UHFFFAOYSA-N 4-amino-3-[[[2-hydroxy-3-(1h-indol-3-yl)propanoyl]-methylamino]methyl]-n-methyl-n-[(1-methylindol-2-yl)methyl]benzamide Chemical compound C1=CC=C2C(CC(O)C(=O)N(C)CC=3C(N)=CC=C(C=3)C(=O)N(CC=3N(C4=CC=CC=C4C=3)C)C)=CNC2=C1 QVWXEBZTEMIIMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- 239000007787 solid Substances 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 238000000746 purification Methods 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 241000588724 Escherichia coli Species 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 14
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 13
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 13
- RQTMFCFEMHFARI-UHFFFAOYSA-N 4-amino-3-[(propanoylamino)methyl]benzoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCC(=O)NCC1=CC(C(O)=O)=CC=C1N RQTMFCFEMHFARI-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000012267 brine Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 9
- BMINWSYCLTUQSH-UHFFFAOYSA-N n-methyl-1-(1-methylindol-2-yl)methanamine Chemical compound C1=CC=C2N(C)C(CNC)=CC2=C1 BMINWSYCLTUQSH-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 229960003500 triclosan Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QZTKDVCDBIDYMD-UHFFFAOYSA-N 2,2'-[(2-amino-2-oxoethyl)imino]diacetic acid Chemical compound NC(=O)CN(CC(O)=O)CC(O)=O QZTKDVCDBIDYMD-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003242 anti bacterial agent Substances 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YVBFINKTQPUKJG-UHFFFAOYSA-N tert-butyl 4-amino-3-(methylaminomethyl)benzoate Chemical compound CNCC1=CC(C(=O)OC(C)(C)C)=CC=C1N YVBFINKTQPUKJG-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- 102000015303 Fatty Acid Synthases Human genes 0.000 description 4
- 108010039731 Fatty Acid Synthases Proteins 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- KFWWCMJSYSSPSK-PAXLJYGASA-N crotonoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)/C=C/C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 KFWWCMJSYSSPSK-PAXLJYGASA-N 0.000 description 4
- UQIDNSKBUXCODH-UHFFFAOYSA-N diazaborine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1B(O)C2=CC=CC=C2C=N1 UQIDNSKBUXCODH-UHFFFAOYSA-N 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- XBIIKDVOUWNBDK-UHFFFAOYSA-N tert-butyl 3-(methylaminomethyl)-4-nitrobenzoate Chemical compound CNCC1=CC(C(=O)OC(C)(C)C)=CC=C1[N+]([O-])=O XBIIKDVOUWNBDK-UHFFFAOYSA-N 0.000 description 4
- MMKNQAMPQDXIGB-UHFFFAOYSA-N 3-[[acetyl(ethoxy)amino]methyl]-4-aminobenzoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCON(C(C)=O)CC1=CC(C(O)=O)=CC=C1N MMKNQAMPQDXIGB-UHFFFAOYSA-N 0.000 description 3
- XDTTUTIFWDAMIX-UHFFFAOYSA-N 3-methyl-4-nitrobenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1[N+]([O-])=O XDTTUTIFWDAMIX-UHFFFAOYSA-N 0.000 description 3
- VPLQHVAPEVLDRE-UHFFFAOYSA-N 4-amino-3-[(4-phenylbutanoylamino)methyl]benzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1CNC(=O)CCCC1=CC=CC=C1 VPLQHVAPEVLDRE-UHFFFAOYSA-N 0.000 description 3
- FPMWWBGYPJCXCU-UHFFFAOYSA-N 4-amino-3-[[(2-hydroxy-4-methylpentanoyl)-methylamino]methyl]benzoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(C)CC(O)C(=O)N(C)CC1=CC(C(O)=O)=CC=C1N FPMWWBGYPJCXCU-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 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 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000193998 Streptococcus pneumoniae Species 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000008121 dextrose Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- FRLLPWADCHCBBY-UHFFFAOYSA-N ethyl 1-methylindole-2-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)OCC)=CC2=C1 FRLLPWADCHCBBY-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- MIEPSGVCFRDTDU-UHFFFAOYSA-N n,1-dimethylindole-2-carboxamide Chemical compound C1=CC=C2N(C)C(C(=O)NC)=CC2=C1 MIEPSGVCFRDTDU-UHFFFAOYSA-N 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Semiconductor Lasers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15852999P | 1999-10-08 | 1999-10-08 | |
| US158529P | 1999-10-08 | ||
| PCT/US2000/027591 WO2001026654A1 (en) | 1999-10-08 | 2000-10-06 | Fab i inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60019954D1 DE60019954D1 (en) | 2005-06-09 |
| DE60019954T2 true DE60019954T2 (de) | 2006-02-23 |
Family
ID=22568552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60019954T Expired - Lifetime DE60019954T2 (de) | 1999-10-08 | 2000-10-06 | Fab i hemmer |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1225895B1 (enExample) |
| JP (1) | JP4961084B2 (enExample) |
| AT (1) | ATE294578T1 (enExample) |
| AU (1) | AU1192501A (enExample) |
| CO (1) | CO5251401A1 (enExample) |
| DE (1) | DE60019954T2 (enExample) |
| HK (1) | HK1049610A1 (enExample) |
| WO (1) | WO2001026654A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO5180550A1 (es) | 1999-04-19 | 2002-07-30 | Smithkline Beecham Corp | Inhibidores de fab i |
| CO5370679A1 (es) | 1999-06-01 | 2004-02-27 | Smithkline Beecham Corp | Inhibidores fab 1 |
| JP4831907B2 (ja) * | 1999-10-08 | 2011-12-07 | アフィニアム・ファーマシューティカルズ・インコーポレイテッド | ＦａｂＩ阻害剤 |
| US6762201B1 (en) | 1999-10-08 | 2004-07-13 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| US6730684B1 (en) * | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| PE20010635A1 (es) | 1999-10-08 | 2001-08-15 | Smithkline Beecham Corp | Inhibidores de fab i utiles para el tratamiento de infecciones bacterianas |
| US20030055037A1 (en) * | 2000-10-06 | 2003-03-20 | Delombaert Stephane | Benzimidazole and indole derivatives as CRF receptor modulators |
| DK1560584T3 (da) | 2001-04-06 | 2009-05-18 | Affinium Pharm Inc | Fab I inhibitorer |
| AU2003298937A1 (en) * | 2002-12-06 | 2004-06-30 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
| CA2519429C (en) * | 2003-03-17 | 2013-08-06 | Affinium Pharmaceuticals, Inc. | Pharmaceutical compositions comprising inhibitors of fab i and further antibiotics |
| DK1879877T3 (da) | 2005-05-03 | 2013-04-15 | Ranbaxy Lab Ltd | Antimikrobielle midler |
| CN101203504B (zh) * | 2005-05-03 | 2012-11-14 | 兰贝克赛实验室有限公司 | 抗微生物剂 |
| JP2009533315A (ja) * | 2006-04-10 | 2009-09-17 | ランバクシー ラボラトリーズ リミテッド | 抗菌剤 |
| WO2008009122A1 (en) | 2006-07-20 | 2008-01-24 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab i inhibitors |
| WO2008098374A1 (en) | 2007-02-16 | 2008-08-21 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab i inhibitors |
| CA2842531C (en) | 2011-08-10 | 2019-07-16 | Janssen R&D Ireland | Antibacterial piperidinyl substituted 3,4-dihydro-1h-[1,8]naphthyridinones |
| EP2742044B1 (en) | 2011-08-10 | 2019-12-04 | Janssen Sciences Ireland Unlimited Company | Antibacterial homopiperidinyl substituted 3,4-dihydro-1h-[1,8]naphthyridinones |
| JO3611B1 (ar) | 2011-08-10 | 2020-08-27 | Janssen Sciences Ireland Uc | سايكلو بنتا (سي (بيرول 4,3 ثاني هيدرو 1 hمستبدله [8,1] نافثيريدينونات مضادة للجراثيم |
| NZ702695A (en) | 2012-06-19 | 2015-10-30 | Debiopharm Int Sa | Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
| EA201590331A1 (ru) | 2012-08-10 | 2016-05-31 | Янссен Сайенсиз Айрлэнд Юси | Новые антибактериальные соединения |
| CA2879623C (en) | 2012-08-10 | 2021-11-02 | Janssen Sciences Ireland Uc | Fused bicyclic azole heterocycle as inhibitors of the enzyme fabi |
| ES2842443T3 (es) | 2016-02-26 | 2021-07-14 | Debiopharm Int Sa | Medicamento para el tratamiento de infecciones del pie diabético |
| IL285204B2 (en) | 2019-02-14 | 2025-02-01 | Debiopharm Int Sa | Formulation of apavicin, method for its preparation |
| EP3982975A1 (en) | 2019-06-14 | 2022-04-20 | Debiopharm International SA | Afabicin for use for treating bacterial infections involving biofilm |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207679B1 (en) * | 1997-06-19 | 2001-03-27 | Sepracor, Inc. | Antimicrobial agents uses and compositions related thereto |
| US5932743A (en) * | 1997-08-21 | 1999-08-03 | American Home Products Corporation | Methods for the solid phase synthesis of substituted indole compounds |
-
2000
- 2000-10-06 AT AT00973420T patent/ATE294578T1/de not_active IP Right Cessation
- 2000-10-06 HK HK03100340.4A patent/HK1049610A1/zh unknown
- 2000-10-06 EP EP00973420A patent/EP1225895B1/en not_active Expired - Lifetime
- 2000-10-06 CO CO00076101A patent/CO5251401A1/es not_active Application Discontinuation
- 2000-10-06 AU AU11925/01A patent/AU1192501A/en not_active Abandoned
- 2000-10-06 DE DE60019954T patent/DE60019954T2/de not_active Expired - Lifetime
- 2000-10-06 JP JP2001529444A patent/JP4961084B2/ja not_active Expired - Fee Related
- 2000-10-06 WO PCT/US2000/027591 patent/WO2001026654A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU1192501A (en) | 2001-04-23 |
| EP1225895B1 (en) | 2005-05-04 |
| EP1225895A1 (en) | 2002-07-31 |
| ATE294578T1 (de) | 2005-05-15 |
| JP4961084B2 (ja) | 2012-06-27 |
| WO2001026654A1 (en) | 2001-04-19 |
| CO5251401A1 (es) | 2003-02-28 |
| EP1225895A4 (en) | 2002-11-13 |
| HK1049610A1 (zh) | 2003-05-23 |
| JP2003511415A (ja) | 2003-03-25 |
| DE60019954D1 (en) | 2005-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |