JP2003502367A - インドール化合物 - Google Patents
インドール化合物Info
- Publication number
- JP2003502367A JP2003502367A JP2001504372A JP2001504372A JP2003502367A JP 2003502367 A JP2003502367 A JP 2003502367A JP 2001504372 A JP2001504372 A JP 2001504372A JP 2001504372 A JP2001504372 A JP 2001504372A JP 2003502367 A JP2003502367 A JP 2003502367A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- indole
- carboxylic acid
- acp
- compounds
- 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.)
- Pending
Links
- 150000002475 indoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- QIBVDZGBSOSZJZ-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methoxy]-1-(4-phenoxyphenyl)sulfonylindole-2-carboxylic acid Chemical compound C=1C=C2N(S(=O)(=O)C=3C=CC(OC=4C=CC=CC=4)=CC=3)C(C(=O)O)=CC2=CC=1OCC1=C(Cl)C=CC=C1Cl QIBVDZGBSOSZJZ-UHFFFAOYSA-N 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- PNVVAAUQNQAZLK-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methoxy]-1-(4-phenylphenyl)sulfonylindole-2-carboxylic acid Chemical compound C=1C=C2N(S(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)C(C(=O)O)=CC2=CC=1OCC1=C(Cl)C=CC=C1Cl PNVVAAUQNQAZLK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 abstract description 9
- 108010039731 Fatty Acid Synthases Proteins 0.000 abstract description 6
- 102000015303 Fatty Acid Synthases Human genes 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229940088710 antibiotic agent Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- -1 2,6-dichlorophenyl Chemical group 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 5
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- ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001851 biosynthetic effect Effects 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 230000001580 bacterial effect Effects 0.000 description 3
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- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
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- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
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- 150000004702 methyl esters Chemical class 0.000 description 3
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- 239000003755 preservative agent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 2
- 108010019608 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase Proteins 0.000 description 2
- 102100037149 3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial Human genes 0.000 description 2
- SYQNUQSGEWNWKV-XUIVZRPNSA-N 4-hydroxy-3,5-dimethyl-5-(2-methyl-buta-1,3-dienyl)-5h-thiophen-2-one Chemical compound C=CC(/C)=C/[C@@]1(C)SC(=O)C(C)=C1O SYQNUQSGEWNWKV-XUIVZRPNSA-N 0.000 description 2
- QIZPONOMFWAPRR-UHFFFAOYSA-N 4-phenoxybenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1OC1=CC=CC=C1 QIZPONOMFWAPRR-UHFFFAOYSA-N 0.000 description 2
- SGPALOFSVGSQQQ-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methoxy]-1h-indole-2-carboxylic acid Chemical compound C=1C=C2NC(C(=O)O)=CC2=CC=1OCC1=C(Cl)C=CC=C1Cl SGPALOFSVGSQQQ-UHFFFAOYSA-N 0.000 description 2
- SYQNUQSGEWNWKV-UHFFFAOYSA-N 5R-Thiolactomycin Natural products C=CC(C)=CC1(C)SC(=O)C(C)=C1O SYQNUQSGEWNWKV-UHFFFAOYSA-N 0.000 description 2
- 108700037654 Acyl carrier protein (ACP) Proteins 0.000 description 2
- 102000048456 Acyl carrier protein (ACP) Human genes 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000206602 Eukaryota Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-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)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
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- 208000027096 gram-negative bacterial infections Diseases 0.000 description 2
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- 238000000338 in vitro Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 230000035699 permeability Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
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- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
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- 150000002632 lipids Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
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- 239000008176 lyophilized powder Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-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)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- IMZPLFBALSDXHR-UHFFFAOYSA-N methyl 5-[(2,6-dichlorophenyl)methoxy]-1h-indole-2-carboxylate Chemical compound C=1C=C2NC(C(=O)OC)=CC2=CC=1OCC1=C(Cl)C=CC=C1Cl IMZPLFBALSDXHR-UHFFFAOYSA-N 0.000 description 1
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- 229940050176 methyl chloride Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 235000013379 molasses Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- ZSLZBFCDCINBPY-YHBLMJDYSA-N s-[2-[3-[[(2r)-4-[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] ethanethioate 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)NCCS[14C](=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-YHBLMJDYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 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
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- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14055899P | 1999-06-23 | 1999-06-23 | |
| US60/140,558 | 1999-06-23 | ||
| PCT/US2000/017244 WO2000078309A1 (en) | 1999-06-23 | 2000-06-22 | Indole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003502367A true JP2003502367A (ja) | 2003-01-21 |
| JP2003502367A5 JP2003502367A5 (https=) | 2007-08-23 |
Family
ID=22491792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001504372A Pending JP2003502367A (ja) | 1999-06-23 | 2000-06-22 | インドール化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6469046B1 (https=) |
| EP (1) | EP1187607A4 (https=) |
| JP (1) | JP2003502367A (https=) |
| AU (1) | AU5633300A (https=) |
| CO (1) | CO5180605A1 (https=) |
| HK (1) | HK1044481A1 (https=) |
| WO (1) | WO2000078309A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007100066A1 (ja) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | １７βＨＳＤｔｙｐｅ５阻害剤 |
| JP2013542960A (ja) * | 2010-11-08 | 2013-11-28 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッド | 脂肪酸シンターゼ阻害剤 |
Families Citing this family (20)
| 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 |
| US6730684B1 (en) | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| US6762201B1 (en) | 1999-10-08 | 2004-07-13 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| HU230030B1 (hu) | 1999-10-08 | 2015-05-28 | Debiopharm International Sa | Fab I inhibitorok |
| EP1560584B1 (en) * | 2001-04-06 | 2009-01-14 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1575951B1 (en) * | 2002-12-06 | 2014-06-25 | Debiopharm International SA | Heterocyclic compounds, methods of making them and their use in therapy |
| WO2004082586A2 (en) | 2003-03-17 | 2004-09-30 | Affinium Pharmaceuticals, Inc. | Phamaceutical compositions comprising inhibitors of fab i and further antibiotics |
| DK1828167T3 (da) * | 2004-06-04 | 2014-10-20 | Debiopharm Int Sa | Acrylamidderivater som antibiotiske midler |
| KR20080075027A (ko) * | 2005-12-05 | 2008-08-13 | 아피늄 파마슈티컬스, 인크. | Ｆａｂｉ 억제제 및 항박테리아제로서의헤테로시클릴아크릴아미드 화합물 |
| JP5468899B2 (ja) | 2006-07-20 | 2014-04-09 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉインヒビターとしてのアクリルアミド誘導体 |
| EP2125802A4 (en) | 2007-02-16 | 2014-08-20 | Debiopharm Int Sa | SALTS, PRODRUGS AND POLYMORPHES OF FAB I INHIBITORS |
| AU2013279021C1 (en) | 2012-06-19 | 2017-03-16 | Debiopharm International 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 |
| ES2753386T3 (es) | 2013-03-13 | 2020-04-08 | Forma Therapeutics Inc | Derivados de 2-hidroxi-1-{4-[(4-fenil)fenil]carbonil}piperazin-1-il}etano-1-ona y compuestos relacionados como inhibidores de sintasa de ácido graso (FASN) para el tratamiento del cáncer |
| RS61312B1 (sr) | 2016-02-26 | 2021-02-26 | Debiopharm Int Sa | Lek za lečenje infekcija dijabetskog stopala |
| WO2019199979A1 (en) * | 2018-04-10 | 2019-10-17 | The General Hospital Corporation | Antibacterial compounds |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
| TN2021000159A1 (en) | 2019-02-14 | 2023-04-04 | Debiopharm Int Sa | Afabicin formulation, method for making the same and uses thereof |
| SG11202113174SA (en) | 2019-06-14 | 2021-12-30 | Debiopharm Int Sa | Medicament and use thereof for treating bacterial infections involving biofilm |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5482960A (en) | 1994-11-14 | 1996-01-09 | Warner-Lambert Company | Nonpeptide endothelin antagonists |
-
2000
- 2000-06-19 CO CO00045411A patent/CO5180605A1/es not_active Application Discontinuation
- 2000-06-22 AU AU56333/00A patent/AU5633300A/en not_active Abandoned
- 2000-06-22 HK HK02106181.4A patent/HK1044481A1/zh unknown
- 2000-06-22 EP EP00941654A patent/EP1187607A4/en not_active Withdrawn
- 2000-06-22 US US09/980,304 patent/US6469046B1/en not_active Expired - Fee Related
- 2000-06-22 WO PCT/US2000/017244 patent/WO2000078309A1/en not_active Ceased
- 2000-06-22 JP JP2001504372A patent/JP2003502367A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007100066A1 (ja) * | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | １７βＨＳＤｔｙｐｅ５阻害剤 |
| US7855225B2 (en) | 2006-03-02 | 2010-12-21 | Astellas Pharma Inc. | 17βHSD type 5 inhibitor |
| JP2013542960A (ja) * | 2010-11-08 | 2013-11-28 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッド | 脂肪酸シンターゼ阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000078309A1 (en) | 2000-12-28 |
| EP1187607A4 (en) | 2004-01-28 |
| EP1187607A1 (en) | 2002-03-20 |
| HK1044481A1 (zh) | 2002-10-25 |
| AU5633300A (en) | 2001-01-09 |
| CO5180605A1 (es) | 2002-07-30 |
| US6469046B1 (en) | 2002-10-22 |
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