SK283534B6 - Bicyklické arylkarboxamidy a farmaceutický prostriedok s ich obsahom - Google Patents
Bicyklické arylkarboxamidy a farmaceutický prostriedok s ich obsahom Download PDFInfo
- Publication number
- SK283534B6 SK283534B6 SK644-99A SK64499A SK283534B6 SK 283534 B6 SK283534 B6 SK 283534B6 SK 64499 A SK64499 A SK 64499A SK 283534 B6 SK283534 B6 SK 283534B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- carboxamide
- bicyclic
- arylcarboxamides
- methoxy
- Prior art date
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- -1 Bicyclic aryl carboxamides Chemical class 0.000 title claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract description 8
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 22
- 125000002619 bicyclic group Chemical group 0.000 claims description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000003857 carboxamides Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 102000003390 tumor necrosis factor Human genes 0.000 claims 2
- 125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- NKESBLJNJIVASL-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C(F)(F)F)=NC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl NKESBLJNJIVASL-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 abstract description 3
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 abstract description 3
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 abstract 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 291
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 156
- 150000001875 compounds Chemical class 0.000 description 113
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000007787 solid Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000003818 flash chromatography Methods 0.000 description 26
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 241000700605 Viruses Species 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 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 8
- XDFOGDIBNCBIRK-UHFFFAOYSA-N N-(3,5-dichloropyridin-4-yl)formamide Chemical compound ClC1=CN=CC(Cl)=C1NC=O XDFOGDIBNCBIRK-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011593 sulfur Chemical group 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- ISIQAMHROGZHOV-UHFFFAOYSA-N 3,5-dichloropyridin-4-amine Chemical compound NC1=C(Cl)C=NC=C1Cl ISIQAMHROGZHOV-UHFFFAOYSA-N 0.000 description 4
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 4
- CFCZQLDVZBJWOA-UHFFFAOYSA-N 4-methoxy-2-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC=CC2=C1NC(C(F)(F)F)=N2 CFCZQLDVZBJWOA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- 235000010262 sodium metabisulphite Nutrition 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 230000006433 tumor necrosis factor production Effects 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- FLWMKOLMAQIIAM-UHFFFAOYSA-N 2-acetyl-7-methoxy-3-methylbenzimidazole-4-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)C2=C1N=C(C(C)=O)N2C FLWMKOLMAQIIAM-UHFFFAOYSA-N 0.000 description 3
- ATRYWXPOISMRKP-UHFFFAOYSA-N 2-ethyl-4-methoxy-1,3-benzoxazole Chemical compound C1=CC=C2OC(CC)=NC2=C1OC ATRYWXPOISMRKP-UHFFFAOYSA-N 0.000 description 3
- VNAMULLNUDYWHP-UHFFFAOYSA-N 2-ethyl-4-methoxy-1,3-benzoxazole-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2OC(CC)=NC2=C1OC VNAMULLNUDYWHP-UHFFFAOYSA-N 0.000 description 3
- VHCOEXCZDAHYMW-UHFFFAOYSA-N 4-methoxy-1,3-benzoxazole Chemical compound COC1=CC=CC2=C1N=CO2 VHCOEXCZDAHYMW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 206010003246 arthritis Diseases 0.000 description 3
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- 150000001556 benzimidazoles Chemical class 0.000 description 3
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- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 238000000844 transformation Methods 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- MGQPBXGHGXFKJW-UHFFFAOYSA-N 1,3-benzoxazol-4-ol Chemical compound OC1=CC=CC2=C1N=CO2 MGQPBXGHGXFKJW-UHFFFAOYSA-N 0.000 description 2
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- KCVSWZZMFOZVAD-UHFFFAOYSA-N 1-(4-methoxy-1,3-benzoxazol-2-yl)ethanone Chemical compound COC1=CC=CC2=C1N=C(C(C)=O)O2 KCVSWZZMFOZVAD-UHFFFAOYSA-N 0.000 description 2
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- MKJGHYWJIPWPPZ-UHFFFAOYSA-N 2-ethyl-1,3-benzoxazol-4-ol Chemical compound C1=CC=C2OC(CC)=NC2=C1O MKJGHYWJIPWPPZ-UHFFFAOYSA-N 0.000 description 2
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- RWZGROULVAKNFN-UHFFFAOYSA-N 4-bromo-7-methoxy-2-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC=C(Br)C2=C1N=C(C(F)(F)F)N2 RWZGROULVAKNFN-UHFFFAOYSA-N 0.000 description 2
- XEMWIQXNNYDDID-UHFFFAOYSA-N 4-methoxy-1,3-benzoxazole-7-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)C2=C1N=CO2 XEMWIQXNNYDDID-UHFFFAOYSA-N 0.000 description 2
- PVJIKYOICPVACV-UHFFFAOYSA-N 4-methoxy-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound COC1=CC=CC2=C1N=C(C(F)(F)F)N2C PVJIKYOICPVACV-UHFFFAOYSA-N 0.000 description 2
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9623860.5A GB9623860D0 (en) | 1996-11-15 | 1996-11-15 | Novel compounds |
| GBGB9708062.6A GB9708062D0 (en) | 1997-04-22 | 1997-04-22 | Novel compounds |
| PCT/GB1997/003154 WO1998022460A1 (en) | 1996-11-15 | 1997-11-17 | Bicyclic aryl carboxamides and their therapeutic use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK64499A3 SK64499A3 (en) | 2000-03-13 |
| SK283534B6 true SK283534B6 (sk) | 2003-09-11 |
Family
ID=26310411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK644-99A SK283534B6 (sk) | 1996-11-15 | 1997-11-17 | Bicyklické arylkarboxamidy a farmaceutický prostriedok s ich obsahom |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6353010B1 (enExample) |
| EP (1) | EP0944616B1 (enExample) |
| JP (1) | JP2001504479A (enExample) |
| KR (1) | KR20000053274A (enExample) |
| CN (1) | CN1114604C (enExample) |
| AT (1) | ATE242234T1 (enExample) |
| AU (1) | AU726590B2 (enExample) |
| BR (1) | BR9713507A (enExample) |
| CA (1) | CA2268037A1 (enExample) |
| CZ (1) | CZ158299A3 (enExample) |
| DE (1) | DE69722656T2 (enExample) |
| DK (1) | DK0944616T3 (enExample) |
| ES (1) | ES2200163T3 (enExample) |
| HU (1) | HUP0000189A3 (enExample) |
| ID (1) | ID21698A (enExample) |
| IL (1) | IL129337A0 (enExample) |
| NO (1) | NO992337L (enExample) |
| NZ (1) | NZ335197A (enExample) |
| RU (1) | RU2176642C2 (enExample) |
| SK (1) | SK283534B6 (enExample) |
| TR (1) | TR199901730T2 (enExample) |
| WO (1) | WO1998022460A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000198734A (ja) * | 1998-12-30 | 2000-07-18 | Pfizer Inc | 胃運動性減弱および関連疾患の治療のための運動性増強薬 |
| GB0003254D0 (en) * | 2000-02-11 | 2000-04-05 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| GB0003256D0 (en) | 2000-02-11 | 2000-04-05 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| KR20040010713A (ko) * | 2001-06-15 | 2004-01-31 | 야마노우치세이야쿠 가부시키가이샤 | 페닐피리딘 카보닐 피페라진 유도체 |
| US20040131614A1 (en) * | 2002-07-19 | 2004-07-08 | Abbott Biotechnology Ltd. | Treatment of pulmonary disorders using TNFalpha inhibitor |
| CN1902193B (zh) | 2003-12-04 | 2011-07-13 | 沃泰克斯药物股份有限公司 | 可用作蛋白激酶抑制剂的喹喔啉 |
| US20070225308A1 (en) * | 2004-03-15 | 2007-09-27 | Kyowa Hakko Kogyo Co.,Ltd. | 2-Amino Quinazoline Derivative |
| AU2006214184B2 (en) * | 2005-02-17 | 2012-02-02 | Albany Molecular Research, Inc. | Benzoxazole carboxamides for treating CINV and IBS-D |
| US20060223849A1 (en) * | 2005-03-14 | 2006-10-05 | Mjalli Adnan M | Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors |
| JP5757495B2 (ja) | 2005-05-16 | 2015-07-29 | アッヴィ バイオテクノロジー リミテッド | びらん性多発性関節炎の治療のためのｔｎｆ阻害剤の使用 |
| MX2008010645A (es) * | 2006-02-20 | 2008-10-14 | Astellas Pharma Inc | Derivado de amida o sal del mismo. |
| US9605064B2 (en) | 2006-04-10 | 2017-03-28 | Abbvie Biotechnology Ltd | Methods and compositions for treatment of skin disorders |
| WO2008063213A2 (en) | 2006-04-10 | 2008-05-29 | Abbott Biotechnology Ltd. | Uses and compositions for treatment of psoriatic arthritis |
| WO2008019363A2 (en) * | 2006-08-07 | 2008-02-14 | Albany Molecular Research, Inc. | 2-alkylbenzoxazole carboxamides as 5ht3 modulators |
| US20100056791A1 (en) * | 2006-09-01 | 2010-03-04 | Yasushi Kohno | Pyrazolopyridine carboxamide derivative and phosphodiesterase (pde) inhibitor containing the same |
| NZ575410A (en) * | 2006-09-07 | 2012-03-30 | Biogen Idec Inc | 2-(1H-Indazol-3-ylamino)-1H-benzimidazole derivatives |
| EP2171451A4 (en) | 2007-06-11 | 2011-12-07 | Abbott Biotech Ltd | METHOD FOR TREATING JUVENILIAN IDIOPATHIC ARTHRITIS |
| CL2008001933A1 (es) | 2007-06-29 | 2009-09-25 | Millennium Pharm Inc | Compuestos derivados de pirimidina, inhibidores de la raf quinasa; compuestos intermediarios; procedimiento de preparacion; composicion farmaceutica; y su uso para tratar trastornos proliferativos, cardiacos, neurodegenerativos, inflamatorios, oseos, inmunologicos enfermedad viral, entre otros. |
| CA2752885A1 (en) | 2009-02-27 | 2010-09-02 | Ambit Biosciences Corporation | Jak kinase modulating quinazoline derivatives and methods of use thereof |
| EP2611789A1 (en) | 2010-09-01 | 2013-07-10 | Ambit Biosciences Corporation | Quinazoline compounds and methods of use thereof |
| CA2874303C (en) * | 2012-06-11 | 2020-10-13 | Ucb Biopharma Sprl | Tnf -alpha modulating benz imidazoles |
| WO2014037340A1 (de) * | 2012-09-05 | 2014-03-13 | Bayer Cropscience Ag | Verwendung substituierter 2-amidobenzimidazole, 2-amidobenzoxazole und 2-amidobenzothiazole oder deren salze als wirkstoffe gegen abiotischen pflanzenstress |
| CN108440333A (zh) * | 2018-03-29 | 2018-08-24 | 江苏道博化工有限公司 | 分散染料中间体的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50140442A (enExample) | 1974-04-16 | 1975-11-11 | ||
| EP0116938A1 (en) | 1983-02-14 | 1984-08-29 | Usv Pharmaceutical Corporation | Benzoheterocyclic carbamates |
| DE3835660A1 (de) * | 1988-03-25 | 1989-10-12 | Bayer Ag | 7-substituierte 2-carbonamido-benzthiazol-3-oxide |
| DE4014937A1 (de) | 1990-05-10 | 1991-11-14 | Bayer Ag | 2,3-disubstituierte chinoxaline als leistungsfoerderer fuer tiere |
| GB9219634D0 (en) | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| GB9219632D0 (en) | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| AU675680B2 (en) | 1992-10-14 | 1997-02-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE4237617A1 (de) | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| GB9301660D0 (en) | 1993-01-28 | 1993-03-17 | Smithkline Beecham Plc | Pharmaceuticals |
| GB9306578D0 (en) | 1993-03-30 | 1993-05-26 | Merck Sharp & Dohme | Therapeutic agents |
| ES2152414T3 (es) * | 1994-07-22 | 2001-02-01 | Byk Gulden Lomberg Chem Fab | Dihidrobenzofuranos. |
| US6083961A (en) | 1994-08-03 | 2000-07-04 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole compounds as bradykinin antagonists |
| AU699489B2 (en) * | 1994-10-12 | 1998-12-03 | Euro-Celtique S.A. | Novel benzoxazoles |
| US5665737B1 (en) | 1994-10-12 | 1999-02-16 | Euro Celtique Sa | Substituted benzoxazoles |
-
1997
- 1997-11-17 HU HU0000189A patent/HUP0000189A3/hu unknown
- 1997-11-17 JP JP52334598A patent/JP2001504479A/ja not_active Ceased
- 1997-11-17 AU AU49602/97A patent/AU726590B2/en not_active Ceased
- 1997-11-17 TR TR1999/01730T patent/TR199901730T2/xx unknown
- 1997-11-17 KR KR1019990704253A patent/KR20000053274A/ko not_active Withdrawn
- 1997-11-17 BR BR9713507-0A patent/BR9713507A/pt unknown
- 1997-11-17 EP EP97912370A patent/EP0944616B1/en not_active Expired - Lifetime
- 1997-11-17 NZ NZ335197A patent/NZ335197A/xx unknown
- 1997-11-17 CZ CZ991582A patent/CZ158299A3/cs unknown
- 1997-11-17 ES ES97912370T patent/ES2200163T3/es not_active Expired - Lifetime
- 1997-11-17 ID IDW990356A patent/ID21698A/id unknown
- 1997-11-17 CA CA002268037A patent/CA2268037A1/en not_active Abandoned
- 1997-11-17 DK DK97912370T patent/DK0944616T3/da active
- 1997-11-17 SK SK644-99A patent/SK283534B6/sk unknown
- 1997-11-17 CN CN97199650A patent/CN1114604C/zh not_active Expired - Fee Related
- 1997-11-17 AT AT97912370T patent/ATE242234T1/de not_active IP Right Cessation
- 1997-11-17 IL IL12933797A patent/IL129337A0/xx not_active IP Right Cessation
- 1997-11-17 RU RU99112569/04A patent/RU2176642C2/ru not_active IP Right Cessation
- 1997-11-17 DE DE69722656T patent/DE69722656T2/de not_active Expired - Fee Related
- 1997-11-17 WO PCT/GB1997/003154 patent/WO1998022460A1/en not_active Ceased
-
1999
- 1999-05-14 NO NO992337A patent/NO992337L/no not_active Application Discontinuation
- 1999-10-21 US US09/422,473 patent/US6353010B1/en not_active Expired - Fee Related
-
2002
- 2002-01-14 US US10/050,005 patent/US20020094987A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO992337D0 (no) | 1999-05-14 |
| NZ335197A (en) | 2000-11-24 |
| HUP0000189A3 (en) | 2002-01-28 |
| EP0944616B1 (en) | 2003-06-04 |
| CN1237168A (zh) | 1999-12-01 |
| NO992337L (no) | 1999-05-14 |
| SK64499A3 (en) | 2000-03-13 |
| KR20000053274A (ko) | 2000-08-25 |
| CZ158299A3 (cs) | 1999-09-15 |
| JP2001504479A (ja) | 2001-04-03 |
| BR9713507A (pt) | 2000-02-29 |
| IL129337A0 (en) | 2000-02-17 |
| DK0944616T3 (da) | 2003-09-29 |
| ATE242234T1 (de) | 2003-06-15 |
| HUP0000189A2 (hu) | 2001-04-28 |
| AU4960297A (en) | 1998-06-10 |
| TR199901730T2 (xx) | 1999-09-21 |
| US6353010B1 (en) | 2002-03-05 |
| US20020094987A1 (en) | 2002-07-18 |
| EP0944616A1 (en) | 1999-09-29 |
| ES2200163T3 (es) | 2004-03-01 |
| RU2176642C2 (ru) | 2001-12-10 |
| ID21698A (id) | 1999-07-15 |
| DE69722656T2 (de) | 2004-05-13 |
| AU726590B2 (en) | 2000-11-09 |
| CN1114604C (zh) | 2003-07-16 |
| CA2268037A1 (en) | 1998-05-28 |
| WO1998022460A1 (en) | 1998-05-28 |
| DE69722656D1 (de) | 2003-07-10 |
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