UA73187C2 - Substituted in orthoposition amides of anthranilic acid and their use as medicaments - Google Patents

Substituted in orthoposition amides of anthranilic acid and their use as medicaments Download PDF

Info

Publication number: UA73187C2
Authority: UA; Ukraine
Prior art keywords: compounds; diseases; chlorine; group; acid
Prior art date: 2000-05-09

Application number

UA2002129865A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-05-09

Filing date

2001-08-05

Publication date

2005-06-15

2001-08-05 Application filed by Schering Ag filed Critical Schering Ag

2005-06-15 Publication of UA73187C2 publication Critical patent/UA73187C2/uk

Links

239000003814 drug Substances 0.000 title claims abstract description 10
150000001408 amides Chemical class 0.000 title description 20
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 20
201000010099 disease Diseases 0.000 claims description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
229940124597 therapeutic agent Drugs 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
208000003120 Angiofibroma Diseases 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 5
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 5
206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
206010016654 Fibrosis Diseases 0.000 claims description 5
208000010412 Glaucoma Diseases 0.000 claims description 5
206010018364 Glomerulonephritis Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
206010003246 arthritis Diseases 0.000 claims description 5
230000007882 cirrhosis Effects 0.000 claims description 5
208000019425 cirrhosis of liver Diseases 0.000 claims description 5
208000033679 diabetic kidney disease Diseases 0.000 claims description 5
208000030533 eye disease Diseases 0.000 claims description 5
230000003176 fibrotic effect Effects 0.000 claims description 5
201000011066 hemangioma Diseases 0.000 claims description 5
208000017169 kidney disease Diseases 0.000 claims description 5
210000004185 liver Anatomy 0.000 claims description 5
230000003211 malignant effect Effects 0.000 claims description 5
210000003584 mesangial cell Anatomy 0.000 claims description 5
201000003142 neovascular glaucoma Diseases 0.000 claims description 5
201000009925 nephrosclerosis Diseases 0.000 claims description 5
230000035755 proliferation Effects 0.000 claims description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
206010063209 Chronic allograft nephropathy Diseases 0.000 claims description 4
206010052779 Transplant rejections Diseases 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
230000002792 vascular Effects 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
231100000858 damage to nervous tissue Toxicity 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 2
210000000944 nerve tissue Anatomy 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
238000012876 topography Methods 0.000 claims 1
230000033115 angiogenesis Effects 0.000 abstract description 8
230000002085 persistent effect Effects 0.000 abstract description 7
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 abstract description 3
230000001960 triggered effect Effects 0.000 abstract 1
239000002904 solvent Substances 0.000 description 38
239000000243 solution Substances 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 for example Chemical class 0.000 description 18
238000000034 method Methods 0.000 description 17
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
230000003993 interaction Effects 0.000 description 13
125000003277 amino group Chemical group 0.000 description 12
238000009835 boiling Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 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
229960000583 acetic acid Drugs 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
108020003175 receptors Proteins 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
239000000758 substrate Substances 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
108091000080 Phosphotransferase Proteins 0.000 description 4
230000009471 action Effects 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
102000020233 phosphotransferase Human genes 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
238000003828 vacuum filtration Methods 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
238000010934 O-alkylation reaction Methods 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 3
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 3
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
229960004050 aminobenzoic acid Drugs 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 3
239000012089 stop solution Substances 0.000 description 3
QWZHDKGQKYEBKK-UHFFFAOYSA-N 3-aminochromen-2-one Chemical compound C1=CC=C2OC(=O)C(N)=CC2=C1 QWZHDKGQKYEBKK-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
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 2
229910021380 Manganese Chloride Inorganic materials 0.000 description 2
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000012010 growth Effects 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000011630 iodine Chemical group 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910001629 magnesium chloride Inorganic materials 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
239000011572 manganese Substances 0.000 description 2
239000011565 manganese chloride Substances 0.000 description 2
235000002867 manganese chloride Nutrition 0.000 description 2
229940099607 manganese chloride Drugs 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
229940080469 phosphocellulose Drugs 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000008569 process Effects 0.000 description 2
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
238000004448 titration Methods 0.000 description 2
ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
230000008728 vascular permeability Effects 0.000 description 2
229910000166 zirconium phosphate Inorganic materials 0.000 description 2
USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UPPNJZSFIIFBPQ-UHFFFAOYSA-N 2-(pyridin-4-ylmethylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NCC1=CC=NC=C1 UPPNJZSFIIFBPQ-UHFFFAOYSA-N 0.000 description 1
MQMWPBBDMIYYMI-UHFFFAOYSA-N 2-aminophenylglyoxylic acid Chemical compound NC1=CC=CC=C1C(=O)C(O)=O MQMWPBBDMIYYMI-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
ACMLKANOGIVEPB-UHFFFAOYSA-N 2-oxo-2H-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(=O)C(C(=O)O)=CC2=C1 ACMLKANOGIVEPB-UHFFFAOYSA-N 0.000 description 1
XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229940123073 Angiotensin antagonist Drugs 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000032544 Cicatrix Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
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230000008092 positive effect Effects 0.000 description 1
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230000002829 reductive effect Effects 0.000 description 1
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239000000741 silica gel Substances 0.000 description 1
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LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
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RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
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230000004614 tumor growth Effects 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Diabetes (AREA)
Ophthalmology & Optometry (AREA)
Urology & Nephrology (AREA)
Rheumatology (AREA)
Hematology (AREA)
Neurology (AREA)
Obesity (AREA)
Surgery (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Vascular Medicine (AREA)
Neurosurgery (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Transplantation (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UA2002129865A 2000-05-09 2001-08-05 Substituted in orthoposition amides of anthranilic acid and their use as medicaments UA73187C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10023486A DE10023486C1 (de)	2000-05-09	2000-05-09	Ortho substituierte Anthranilsäureamide und deren Verwendung als Arzneimittel
PCT/EP2001/005214 WO2001085719A1 (fr)	2000-05-09	2001-05-08	Amides d'acide anthranilique ortho-substitues et leur utilisation en tant que medicaments

Publications (1)

Publication Number	Publication Date
UA73187C2 true UA73187C2 (en)	2005-06-15

Family

ID=7641923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002129865A UA73187C2 (en)	2000-05-09	2001-08-05	Substituted in orthoposition amides of anthranilic acid and their use as medicaments

Country Status (30)

Country	Link
US (2)	US7081468B2 (fr)
EP (1)	EP1280799B1 (fr)
JP (1)	JP2003532725A (fr)
KR (1)	KR20020094024A (fr)
CN (1)	CN1237062C (fr)
AT (1)	ATE258174T1 (fr)
AU (2)	AU7400101A (fr)
BG (1)	BG107261A (fr)
BR (1)	BR0110621A (fr)
CA (1)	CA2407852A1 (fr)
CZ (1)	CZ20023677A3 (fr)
DE (2)	DE10023486C1 (fr)
DK (1)	DK1280799T3 (fr)
EE (1)	EE04938B1 (fr)
ES (1)	ES2214424T3 (fr)
HR (1)	HRP20020977B1 (fr)
HU (1)	HUP0301954A2 (fr)
IL (2)	IL152578A0 (fr)
MX (1)	MXPA02010915A (fr)
NO (1)	NO323541B1 (fr)
NZ (1)	NZ521700A (fr)
PL (1)	PL358204A1 (fr)
PT (1)	PT1280799E (fr)
RU (1)	RU2264399C2 (fr)
SK (1)	SK15882002A3 (fr)
TR (1)	TR200400912T4 (fr)
UA (1)	UA73187C2 (fr)
WO (1)	WO2001085719A1 (fr)
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ZA (1)	ZA200209896B (fr)

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EP3157521A4 (fr) *	2014-06-20	2018-02-14	Aurigene Discovery Technologies Limited	Composés d'imidazole substitués en tant qu'inhibiteurs de l'irak4
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2000
- 2000-05-09 DE DE10023486A patent/DE10023486C1/de not_active Expired - Fee Related
2001
- 2001-05-08 WO PCT/EP2001/005214 patent/WO2001085719A1/fr not_active Ceased
- 2001-05-08 AU AU7400101A patent/AU7400101A/xx active Pending
- 2001-05-08 JP JP2001582320A patent/JP2003532725A/ja active Pending
- 2001-05-08 HU HU0301954A patent/HUP0301954A2/hu unknown
- 2001-05-08 PL PL01358204A patent/PL358204A1/xx unknown
- 2001-05-08 EE EEP200200625A patent/EE04938B1/xx not_active IP Right Cessation
- 2001-05-08 IL IL15257801A patent/IL152578A0/xx unknown
- 2001-05-08 ES ES01940416T patent/ES2214424T3/es not_active Expired - Lifetime
- 2001-05-08 AU AU2001274001A patent/AU2001274001B2/en not_active Ceased
- 2001-05-08 AT AT01940416T patent/ATE258174T1/de not_active IP Right Cessation
- 2001-05-08 MX MXPA02010915A patent/MXPA02010915A/es active IP Right Grant
- 2001-05-08 US US10/275,480 patent/US7081468B2/en not_active Expired - Fee Related
- 2001-05-08 DK DK01940416T patent/DK1280799T3/da active
- 2001-05-08 RU RU2002131887/04A patent/RU2264399C2/ru not_active IP Right Cessation
- 2001-05-08 YU YU82702A patent/YU82702A/sh unknown
- 2001-05-08 DE DE50101364T patent/DE50101364D1/de not_active Expired - Fee Related
- 2001-05-08 SK SK1588-2002A patent/SK15882002A3/sk unknown
- 2001-05-08 CA CA002407852A patent/CA2407852A1/fr not_active Abandoned
- 2001-05-08 HR HR20020977A patent/HRP20020977B1/xx not_active IP Right Cessation
- 2001-05-08 CZ CZ20023677A patent/CZ20023677A3/cs unknown
- 2001-05-08 CN CNB018091369A patent/CN1237062C/zh not_active Expired - Fee Related
- 2001-05-08 TR TR2004/00912T patent/TR200400912T4/xx unknown
- 2001-05-08 EP EP01940416A patent/EP1280799B1/fr not_active Expired - Lifetime
- 2001-05-08 BR BR0110621-0A patent/BR0110621A/pt not_active IP Right Cessation
- 2001-05-08 KR KR1020027014966A patent/KR20020094024A/ko not_active Abandoned
- 2001-05-08 NZ NZ521700A patent/NZ521700A/en unknown
- 2001-05-08 PT PT01940416T patent/PT1280799E/pt unknown
- 2001-08-05 UA UA2002129865A patent/UA73187C2/uk unknown
2002
- 2002-10-31 IL IL152578A patent/IL152578A/en not_active IP Right Cessation
- 2002-11-08 NO NO20025358A patent/NO323541B1/no unknown
- 2002-11-08 BG BG107261A patent/BG107261A/bg unknown
- 2002-12-05 ZA ZA200209896A patent/ZA200209896B/en unknown
2005
- 2005-09-06 US US11/218,423 patent/US20060014747A1/en not_active Abandoned

Also Published As

Publication number	Publication date
BG107261A (bg)	2003-06-30
PL358204A1 (en)	2004-08-09
DE50101364D1 (de)	2004-02-26
RU2264399C2 (ru)	2005-11-20
WO2001085719A9 (fr)	2001-12-27
DK1280799T3 (da)	2004-05-10
CN1427837A (zh)	2003-07-02
DE10023486C1 (de)	2002-03-14
HK1056728A1 (en)	2004-02-27
US7081468B2 (en)	2006-07-25
NO20025358D0 (no)	2002-11-08
CN1237062C (zh)	2006-01-18
TR200400912T4 (tr)	2004-07-21
KR20020094024A (ko)	2002-12-16
ZA200209896B (en)	2004-03-05
AU7400101A (en)	2001-11-20
BR0110621A (pt)	2003-03-25
US20040102441A1 (en)	2004-05-27
HUP0301954A2 (hu)	2003-09-29
AU2001274001B2 (en)	2007-01-18
CZ20023677A3 (cs)	2003-02-12
MXPA02010915A (es)	2003-07-14
WO2001085719A1 (fr)	2001-11-15
NO323541B1 (no)	2007-06-11
NO20025358L (no)	2002-11-08
IL152578A0 (en)	2003-05-29
NZ521700A (en)	2005-09-30
EE04938B1 (et)	2007-12-17
CA2407852A1 (fr)	2001-11-15
ATE258174T1 (de)	2004-02-15
JP2003532725A (ja)	2003-11-05
EE200200625A (et)	2004-04-15
IL152578A (en)	2008-11-03
EP1280799A1 (fr)	2003-02-05
US20060014747A1 (en)	2006-01-19
YU82702A (sh)	2006-05-25
HRP20020977A2 (en)	2005-02-28
SK15882002A3 (sk)	2003-08-05
HRP20020977B1 (hr)	2008-05-31
EP1280799B1 (fr)	2004-01-21
PT1280799E (pt)	2004-06-30
ES2214424T3 (es)	2004-09-16

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