BG64624B1 - (бензодиоксанови, бензофуранови или бензопиранови) производни, притежаващи фундусни релаксиращи свойства - Google Patents
(бензодиоксанови, бензофуранови или бензопиранови) производни, притежаващи фундусни релаксиращи свойства Download PDFInfo
- Publication number
- BG64624B1 BG64624B1 BG104372A BG10437200A BG64624B1 BG 64624 B1 BG64624 B1 BG 64624B1 BG 104372 A BG104372 A BG 104372A BG 10437200 A BG10437200 A BG 10437200A BG 64624 B1 BG64624 B1 BG 64624B1
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- BG
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- Prior art keywords
- formula
- alkyl
- hydrogen
- radical
- compounds
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title 1
- 150000001562 benzopyrans Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- -1 hydroxy halogen Chemical group 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 17
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 13
- 238000012360 testing method Methods 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- HTHYHKLEFHPLHL-OAHLLOKOSA-N 1-[3-[[(2r)-3,4-dihydro-2h-chromen-2-yl]methylamino]propyl]-1,3-diazinan-2-one Chemical compound O=C1NCCCN1CCCNC[C@@H]1OC2=CC=CC=C2CC1 HTHYHKLEFHPLHL-OAHLLOKOSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 230000008602 contraction Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000001204 N-oxides Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
- 229940076279 serotonin Drugs 0.000 claims 5
- HTHYHKLEFHPLHL-UHFFFAOYSA-N 1-[3-(3,4-dihydro-2h-chromen-2-ylmethylamino)propyl]-1,3-diazinan-2-one Chemical compound O=C1NCCCN1CCCNCC1OC2=CC=CC=C2CC1 HTHYHKLEFHPLHL-UHFFFAOYSA-N 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 abstract description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 239000000543 intermediate Substances 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000003054 catalyst Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 230000002496 gastric effect Effects 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 210000002784 stomach Anatomy 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 201000006549 dyspepsia Diseases 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000000796 flavoring agent Substances 0.000 description 7
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- BSRHATGBRQMDRF-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-2-ylmethanamine Chemical class C1=CC=C2OC(CN)CCC2=C1 BSRHATGBRQMDRF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 108010037444 diisopropylglutathione ester Proteins 0.000 description 6
- 235000003599 food sweetener Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 235000019634 flavors Nutrition 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000003044 adaptive effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
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- 208000002551 irritable bowel syndrome Diseases 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002040 relaxant effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010021518 Impaired gastric emptying Diseases 0.000 description 3
- 125000000815 N-oxide group Chemical group 0.000 description 3
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 238000005984 hydrogenation reaction Methods 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 235000019198 oils Nutrition 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
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- 235000020357 syrup Nutrition 0.000 description 3
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- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 2
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010059186 Early satiety Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
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- GSHUZVSNIBLGMR-UHFFFAOYSA-N calcium;1,1-dioxo-1,2-benzothiazol-3-one Chemical compound [Ca].C1=CC=C2C(=O)NS(=O)(=O)C2=C1 GSHUZVSNIBLGMR-UHFFFAOYSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UJRJCSCBZXLGKF-UHFFFAOYSA-N nickel rhenium Chemical compound [Ni].[Re] UJRJCSCBZXLGKF-UHFFFAOYSA-N 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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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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- 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
- C07D405/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97203808 | 1997-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG104372A BG104372A (en) | 2000-12-29 |
| BG64624B1 true BG64624B1 (bg) | 2005-09-30 |
Family
ID=8229014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG104372A BG64624B1 (bg) | 1997-12-05 | 2000-04-24 | (бензодиоксанови, бензофуранови или бензопиранови) производни, притежаващи фундусни релаксиращи свойства |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US6133277A (cs) |
| EP (1) | EP1036073B8 (cs) |
| JP (1) | JP2001525407A (cs) |
| KR (1) | KR100591605B1 (cs) |
| CN (1) | CN1155597C (cs) |
| AR (1) | AR017195A1 (cs) |
| AT (1) | ATE334125T1 (cs) |
| AU (1) | AU748669B2 (cs) |
| BG (1) | BG64624B1 (cs) |
| BR (1) | BR9814256A (cs) |
| CA (1) | CA2311669C (cs) |
| CO (1) | CO5011114A1 (cs) |
| CZ (1) | CZ297895B6 (cs) |
| DE (1) | DE69835372T2 (cs) |
| EA (1) | EA003365B1 (cs) |
| EE (1) | EE04438B1 (cs) |
| ES (1) | ES2270541T3 (cs) |
| HR (1) | HRP20000340B1 (cs) |
| HU (1) | HU224813B1 (cs) |
| ID (1) | ID24616A (cs) |
| IL (1) | IL136529A (cs) |
| MY (1) | MY124586A (cs) |
| NO (1) | NO320727B1 (cs) |
| NZ (1) | NZ503603A (cs) |
| PL (1) | PL191144B1 (cs) |
| SK (1) | SK286268B6 (cs) |
| TR (1) | TR200001542T2 (cs) |
| TW (1) | TW577886B (cs) |
| UA (1) | UA70308C2 (cs) |
| WO (1) | WO1999029687A1 (cs) |
| ZA (1) | ZA9811081B (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133277A (en) | 1997-12-05 | 2000-10-17 | Janssen Pharmaceutica N.V. | (Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
| EP1187829B1 (en) * | 1999-06-02 | 2003-12-10 | Janssen Pharmaceutica N.V. | Aminoalkyl substituted (benzodioxan, benzofuran or benzopyran) derivatives |
| CN1131862C (zh) * | 1999-06-02 | 2003-12-24 | 詹森药业有限公司 | 经吡咯烷基、哌啶基或高哌啶基取代的(苯并二噁烷,苯并呋喃或苯并吡喃)衍生物 |
| JO2352B1 (en) * | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Compounds for the treatment of non-adaptation of the bottom of the uterus |
| JO2654B1 (en) * | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
| JO2409B1 (en) * | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
| US6688079B2 (en) | 2001-04-18 | 2004-02-10 | Kraft Foods Holdings, Inc. | Method for manufacturing flexible packages having slide closures |
| EP1445324A4 (en) * | 2001-11-09 | 2005-02-16 | Kaneka Corp | PROCESS FOR PRODUCING OPTICALLY ACTIVE CHROMAN DERIVATIVE AND INTERMEDIATE PRODUCT |
| ES2199086B1 (es) | 2002-07-31 | 2005-06-01 | Cepa Schwarz Pharma Sl | Nuevos derivados de cicloalcanodionas, procedimiento para su preparacion y sus aplicaciones farmacologicas. |
| US7071821B2 (en) * | 2003-05-14 | 2006-07-04 | Bellsouth Intellectual Property Corporation | Method and system for alerting a person to a situation |
| ITTO20030140U1 (it) * | 2003-09-16 | 2005-03-17 | Interfila Srl | Matita cosmetica |
| US7514461B2 (en) * | 2003-09-19 | 2009-04-07 | Edison Pharmaceuticals, Inc. | Chroman derivatives |
| WO2005054209A1 (en) | 2003-11-20 | 2005-06-16 | Janssen Pharmaceutica N.V. | 7-phenylalkyl substituted 2-quinolinones and 2 quinoxalinones as poly(adp-ribose) polymerase inhibitors |
| US7855207B2 (en) | 2003-11-20 | 2010-12-21 | Janssen Pharmaceutica, Nv | 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(adpribose) polymerase inhibitors |
| ES2238015B1 (es) * | 2004-01-30 | 2006-11-01 | Cepa Schwarz Pharma, S.L. | Derivados de cicloalcanodionas con actividad neuroprotectora. |
| SG154432A1 (en) | 2004-06-30 | 2009-08-28 | Janssen Pharmaceutica Nv | Quinazolinedione derivatives as parp inhibitors |
| CA2569826C (en) | 2004-06-30 | 2013-07-16 | Janssen Pharmaceutica N.V. | Substituted 2-alkyl quinazolinone derivatives as parp inhibitors |
| JP4852540B2 (ja) | 2004-06-30 | 2012-01-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｐａｒｐ阻害剤としてのフタラジン誘導体 |
| DE102004032277A1 (de) * | 2004-07-02 | 2006-01-19 | Basell Polyolefine Gmbh | Verfahren zur racemoselektiven Synthese von ansa-Metallocenen |
| RU2391350C2 (ru) * | 2004-07-02 | 2010-06-10 | Базелль Полиолефине Гмбх | Способ рацемоселективного синтеза анса-металлоценов |
| WO2006089053A2 (en) | 2005-02-17 | 2006-08-24 | Wyeth | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| WO2006116165A1 (en) * | 2005-04-22 | 2006-11-02 | Wyeth | Chromane and chromene derivatives and uses thereof |
| WO2008015538A2 (en) * | 2006-07-31 | 2008-02-07 | Schwarz Pharma S.L. | Use of diaza- and thiaza-cycloalkanediones for preventing and/or treating pain and /or migraine |
| US20080033050A1 (en) | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| US8503431B2 (en) * | 2006-08-25 | 2013-08-06 | Wireless Wonders Ltd. | Mobile phone related indirect communication system and method |
| SI2134691T1 (sl) | 2007-03-08 | 2012-06-29 | Janssen Pharmaceutica Nv | Derivati kvinolina kot PARP in TANK inhibitorji |
| JP5017703B2 (ja) * | 2007-05-16 | 2012-09-05 | 住友ゴム工業株式会社 | ビードエイペックスおよびタイヤ |
| WO2009053373A1 (en) | 2007-10-26 | 2009-04-30 | Janssen Pharmaceutica Nv | Quinolinone derivatives as parp inhibitors |
| RU2490260C2 (ru) | 2008-03-27 | 2013-08-20 | Янссен Фармацевтика Нв | Тетрагидрофенантридиноны и тетрагидроциклопентахинолиноны в качестве ингибиторов parp и ингибиторов полимеризации тубулина |
| AU2009228945B2 (en) | 2008-03-27 | 2013-05-02 | Janssen Pharmaceutica Nv | Quinazolinone derivatives as tubulin polymerization inhibitors |
| SG11201405117SA (en) | 2012-02-24 | 2014-09-26 | Lupin Ltd | Substituted chroman compounds as calcium sensing receptor modulators |
| DE102012206062B4 (de) | 2012-04-13 | 2019-09-12 | Adidas Ag | Schuhoberteil |
| WO2014102592A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Oxime/substituted quinoxaline-type piperidine compounds and uses thereof |
| DE102013207163B4 (de) | 2013-04-19 | 2022-09-22 | Adidas Ag | Schuhoberteil |
| DE102014220087B4 (de) | 2014-10-02 | 2016-05-12 | Adidas Ag | Flachgestricktes Schuhoberteil für Sportschuhe |
| EP3397643A1 (en) | 2015-12-30 | 2018-11-07 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Pt(IV) PRODRUGS |
Citations (7)
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|---|---|---|---|---|
| DE2400094A1 (de) * | 1973-01-04 | 1974-07-18 | Janssen Pharmaceutica Nv | 1-geschweifte klammer auf 1- eckige klammer auf 2-(1,4-benzodioxan-2-yl) -2-hydroxyaethyl eckige klammer zu -4-piperidyl geschweifte klammer zu -2-benzimidazolinone, verfahren zu iherer herstellung und arzneimittel |
| US5137901A (en) * | 1988-07-28 | 1992-08-11 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| EP0546388A1 (de) * | 1991-12-09 | 1993-06-16 | Bayer Ag | Azaheterocyclylmethyl-chromane als Wirkstoffe zur Behandlung von Erkrankungen des Zentralnervensystems |
| WO1993017017A1 (en) * | 1992-02-27 | 1993-09-02 | Janssen Pharmaceutica N.V. | [(benzodioxan, benzofuran or benzopyran)-alkylamino] alkyl substituted guanidines as selective vascoconstrictors |
| WO1995005383A1 (en) * | 1993-08-19 | 1995-02-23 | Janssen Pharmaceutica N.V. | Vasocontrictive dihydrobenzopyran derivatives |
| US5541199A (en) * | 1995-06-02 | 1996-07-30 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
| WO1997028157A1 (fr) * | 1996-02-01 | 1997-08-07 | Pierre Fabre Medicament | Nouveaux derives de la piperidine substitues en position 4 par un groupe imidazolidin-2-on-1-yl-ethyl, tetrahydropyrimidin-2-on-1-yl-ethyl, et 1,3-dia-zepin-2-on-1-yl-ethyl, et leurs applications comme antagonistes des recepteurs alpha-2 adrenergiques |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929801A (en) * | 1973-11-20 | 1975-12-30 | Janssen Pharmaceutica Nv | 2-Benzimidazolinones |
| GB1599296A (en) * | 1977-07-06 | 1981-09-30 | Brewster D L | Ice making machine |
| GR71865B (cs) * | 1978-03-20 | 1983-07-07 | Ciba Geigy | |
| DE2852945A1 (de) * | 1978-12-07 | 1980-06-26 | Boehringer Sohn Ingelheim | Benzodioxanyl-hydroxyaethylpiperidyl- imidazolidinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4329348A (en) * | 1979-02-26 | 1982-05-11 | Ciba-Geigy Corporation | N-Oxacyclic-alkylpiperidines as psychostimulants |
| US4239348A (en) * | 1979-11-30 | 1980-12-16 | Hughes Aircraft Company | High resolution AC silicon MOS light-valve substrate |
| DE4319038A1 (de) * | 1993-06-08 | 1994-12-15 | Bayer Ag | Verwendung von teilweise bekannten substituierten Chromanen als Arzneimittel, neue Wirkstoffe und Verfahren zu ihrer Herstellung |
| US5696653A (en) * | 1996-12-13 | 1997-12-09 | Phase Metrics | Tooling for holding a head gimbal assembly |
| US6133277A (en) * | 1997-12-05 | 2000-10-17 | Janssen Pharmaceutica N.V. | (Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
-
1998
- 1998-11-16 US US09/192,686 patent/US6133277A/en not_active Expired - Lifetime
- 1998-11-25 TW TW087119526A patent/TW577886B/zh not_active IP Right Cessation
- 1998-11-27 KR KR1020007003796A patent/KR100591605B1/ko not_active Expired - Fee Related
- 1998-11-27 CZ CZ20002018A patent/CZ297895B6/cs not_active IP Right Cessation
- 1998-11-27 NZ NZ503603A patent/NZ503603A/en unknown
- 1998-11-27 DE DE69835372T patent/DE69835372T2/de not_active Expired - Lifetime
- 1998-11-27 SK SK803-2000A patent/SK286268B6/sk not_active IP Right Cessation
- 1998-11-27 TR TR2000/01542T patent/TR200001542T2/xx unknown
- 1998-11-27 BR BR9814256-9A patent/BR9814256A/pt not_active Application Discontinuation
- 1998-11-27 EP EP98966603A patent/EP1036073B8/en not_active Expired - Lifetime
- 1998-11-27 EA EA200000616A patent/EA003365B1/ru not_active IP Right Cessation
- 1998-11-27 AT AT98966603T patent/ATE334125T1/de not_active IP Right Cessation
- 1998-11-27 CN CNB988118319A patent/CN1155597C/zh not_active Expired - Fee Related
- 1998-11-27 ID IDW20001041D patent/ID24616A/id unknown
- 1998-11-27 WO PCT/EP1998/007771 patent/WO1999029687A1/en active IP Right Grant
- 1998-11-27 PL PL341007A patent/PL191144B1/pl not_active IP Right Cessation
- 1998-11-27 EE EEP200000328A patent/EE04438B1/xx not_active IP Right Cessation
- 1998-11-27 ES ES98966603T patent/ES2270541T3/es not_active Expired - Lifetime
- 1998-11-27 IL IL13652998A patent/IL136529A/xx not_active IP Right Cessation
- 1998-11-27 UA UA2000053031A patent/UA70308C2/uk unknown
- 1998-11-27 CA CA2311669A patent/CA2311669C/en not_active Expired - Lifetime
- 1998-11-27 HR HR20000340A patent/HRP20000340B1/xx not_active IP Right Cessation
- 1998-11-27 AU AU24127/99A patent/AU748669B2/en not_active Ceased
- 1998-11-27 HU HU0004492A patent/HU224813B1/hu not_active IP Right Cessation
- 1998-11-27 JP JP2000524281A patent/JP2001525407A/ja active Pending
- 1998-12-01 MY MYPI98005442A patent/MY124586A/en unknown
- 1998-12-01 CO CO98071204A patent/CO5011114A1/es unknown
- 1998-12-03 ZA ZA9811081A patent/ZA9811081B/xx unknown
- 1998-12-04 AR ARP980106182A patent/AR017195A1/es active IP Right Grant
-
2000
- 2000-04-19 NO NO20002074A patent/NO320727B1/no not_active IP Right Cessation
- 2000-04-24 BG BG104372A patent/BG64624B1/bg unknown
- 2000-08-18 US US09/641,485 patent/US6495547B1/en not_active Expired - Lifetime
-
2002
- 2002-04-03 US US10/116,590 patent/US6747045B2/en not_active Expired - Lifetime
- 2002-09-05 US US10/235,623 patent/US6852714B2/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2400094A1 (de) * | 1973-01-04 | 1974-07-18 | Janssen Pharmaceutica Nv | 1-geschweifte klammer auf 1- eckige klammer auf 2-(1,4-benzodioxan-2-yl) -2-hydroxyaethyl eckige klammer zu -4-piperidyl geschweifte klammer zu -2-benzimidazolinone, verfahren zu iherer herstellung und arzneimittel |
| US5137901A (en) * | 1988-07-28 | 1992-08-11 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| EP0546388A1 (de) * | 1991-12-09 | 1993-06-16 | Bayer Ag | Azaheterocyclylmethyl-chromane als Wirkstoffe zur Behandlung von Erkrankungen des Zentralnervensystems |
| WO1993017017A1 (en) * | 1992-02-27 | 1993-09-02 | Janssen Pharmaceutica N.V. | [(benzodioxan, benzofuran or benzopyran)-alkylamino] alkyl substituted guanidines as selective vascoconstrictors |
| WO1995005383A1 (en) * | 1993-08-19 | 1995-02-23 | Janssen Pharmaceutica N.V. | Vasocontrictive dihydrobenzopyran derivatives |
| US5541199A (en) * | 1995-06-02 | 1996-07-30 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
| WO1997028157A1 (fr) * | 1996-02-01 | 1997-08-07 | Pierre Fabre Medicament | Nouveaux derives de la piperidine substitues en position 4 par un groupe imidazolidin-2-on-1-yl-ethyl, tetrahydropyrimidin-2-on-1-yl-ethyl, et 1,3-dia-zepin-2-on-1-yl-ethyl, et leurs applications comme antagonistes des recepteurs alpha-2 adrenergiques |
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