ES2211315B1 - Nuevos compuestos triciclicos. - Google Patents
Nuevos compuestos triciclicos.Info
- Publication number
- ES2211315B1 ES2211315B1 ES200202590A ES200202590A ES2211315B1 ES 2211315 B1 ES2211315 B1 ES 2211315B1 ES 200202590 A ES200202590 A ES 200202590A ES 200202590 A ES200202590 A ES 200202590A ES 2211315 B1 ES2211315 B1 ES 2211315B1
- Authority
- ES
- Spain
- Prior art keywords
- dihydro
- benzoxepino
- thio
- acid
- difluoroquinolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 137
- 238000002360 preparation method Methods 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 10
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims abstract description 8
- 230000001575 pathological effect Effects 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 7
- -1 monoalkylamino Chemical group 0.000 claims description 197
- 239000002253 acid Substances 0.000 claims description 94
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 87
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 25
- 229920002554 vinyl polymer Polymers 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 235000019260 propionic acid Nutrition 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 208000024780 Urticaria Diseases 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000002685 pulmonary effect Effects 0.000 claims description 6
- PMSGXRLYMCEJQU-ZZXKWVIFSA-N 9-[(e)-2-(6,7-difluoroquinolin-2-yl)ethenyl]-11-[2-(2h-tetrazol-5-yl)ethylsulfanyl]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridine Chemical compound N1=C2C=C(F)C(F)=CC2=CC=C1\C=C\C(C=C12)=CC=C1OCC1=NC=CC=C1C2SCCC1=NN=NN1 PMSGXRLYMCEJQU-ZZXKWVIFSA-N 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 208000001640 Fibromyalgia Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010061876 Obstruction Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 230000008485 antagonism Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 206010011796 Cystitis interstitial Diseases 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 230000004075 alteration Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 46
- 239000005557 antagonist Substances 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 208000037765 diseases and disorders Diseases 0.000 abstract description 6
- 230000004071 biological effect Effects 0.000 abstract description 2
- 230000001629 suppression Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
- 239000000047 product Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 14
- 235000012239 silicon dioxide Nutrition 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 11
- 229910052906 cristobalite Inorganic materials 0.000 description 11
- 229910052682 stishovite Inorganic materials 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 229910052905 tridymite Inorganic materials 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000002841 Lewis acid Substances 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
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- 210000004072 lung Anatomy 0.000 description 5
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- LWLWVLMRYZVTMZ-UHFFFAOYSA-N pyrido[2,3-b]azepin-5-one Chemical compound O=C1C=CC=NC2=NC=CC=C12 LWLWVLMRYZVTMZ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 5
- QQJODMUSGDSKPF-UHFFFAOYSA-N 2-(chloromethyl)benzaldehyde Chemical class ClCC1=CC=CC=C1C=O QQJODMUSGDSKPF-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
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- 229920002261 Corn starch Polymers 0.000 description 4
- 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 4
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
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- 229960001375 lactose Drugs 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
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- 238000004448 titration Methods 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
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- OEBIVOHKFYSBPE-UHFFFAOYSA-N 4-Benzyloxybenzyl alcohol Chemical compound C1=CC(CO)=CC=C1OCC1=CC=CC=C1 OEBIVOHKFYSBPE-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 201000003883 Cystic fibrosis Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 239000013543 active substance Substances 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
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- 125000002757 morpholinyl group Chemical group 0.000 description 3
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- 102000004169 proteins and genes Human genes 0.000 description 3
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- 125000003226 pyrazolyl group Chemical group 0.000 description 3
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- 229920006395 saturated elastomer Polymers 0.000 description 3
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- 230000000802 nitrating effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002920 oxepines Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- DWRGLIHFAJTMGM-UHFFFAOYSA-N thiohydroxylamine;hydrochloride Chemical compound Cl.SN DWRGLIHFAJTMGM-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/06—Antimigraine agents
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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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Hydrogenated Pyridines (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200202590A ES2211315B1 (es) | 2002-11-12 | 2002-11-12 | Nuevos compuestos triciclicos. |
| PCT/EP2003/012581 WO2004043966A1 (en) | 2002-11-12 | 2003-11-11 | New tricyclic derivatives as ltd4 antagonists |
| RU2005118757/04A RU2330855C2 (ru) | 2002-11-12 | 2003-11-11 | Новые трициклические производные, как антагонисты ltd4 |
| US10/534,487 US7557212B2 (en) | 2002-11-12 | 2003-11-11 | Tricyclic derivatives as LTD4 antagonists |
| EP03779886A EP1560834B1 (en) | 2002-11-12 | 2003-11-11 | New tricyclic derivatives as ltd4 antagonists |
| BR0315462-9A BR0315462A (pt) | 2002-11-12 | 2003-11-11 | Composto, composição farmacêutica, uso de um composto, método para o tratamento de um sujeito que sofre de uma condição patológica ou de doença susceptìvel de alìvio por antagonismo de receptores de ltd4 e produto de combinação |
| CNB2003801085261A CN100379742C (zh) | 2002-11-12 | 2003-11-11 | 用作ltd4拮抗剂的新型三环衍生物 |
| JP2004550982A JP2006508116A (ja) | 2002-11-12 | 2003-11-11 | Ｌｔｄ４アンタゴニストとしての新規三環式誘導体 |
| UAA200505509A UA80996C2 (en) | 2002-11-12 | 2003-11-11 | Tricyclic derivatives as ltd4 antagonists, process for the preparation thereof, intermediate, pharmaceutical composition based thereon, use thereof |
| KR1020057008474A KR20050074605A (ko) | 2002-11-12 | 2003-11-11 | Ｌｔｄ4 길항근으로서의 신규 트리시클릭 유도체 |
| DE60321810T DE60321810D1 (de) | 2002-11-12 | 2003-11-11 | Neue tricyclische derivate als ltd4 antagonisten |
| CA002505491A CA2505491A1 (en) | 2002-11-12 | 2003-11-11 | New tricyclic derivatives as ltd4 antagonists |
| MXPA05005017A MXPA05005017A (es) | 2002-11-12 | 2003-11-11 | Nuevos derivados triciclicos como antagonistas ltd4. |
| AT03779886T ATE399170T1 (de) | 2002-11-12 | 2003-11-11 | Neue tricyclische derivate als ltd4 antagonisten |
| ES03779886T ES2306906T3 (es) | 2002-11-12 | 2003-11-11 | Nuevos derivados triciclicos como antagonistas de ltd4. |
| AU2003288032A AU2003288032A1 (en) | 2002-11-12 | 2003-11-11 | New tricyclic derivatives as ltd4 antagonists |
| ZA200503806A ZA200503806B (en) | 2002-11-12 | 2005-05-11 | New tricyclic derivatives as LTD4 antagonists |
| EC2005005844A ECSP055844A (es) | 2002-11-12 | 2005-06-09 | Nuevos compuestos triciclicos |
| CO05056627A CO5700775A2 (es) | 2002-11-12 | 2005-06-10 | Nuevos derivados triciclicos como antagonistas de ltd4 |
| NO20052858A NO20052858L (no) | 2002-11-12 | 2005-06-13 | Nye tricykliske forbindelser som LTD4-antagonister |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200202590A ES2211315B1 (es) | 2002-11-12 | 2002-11-12 | Nuevos compuestos triciclicos. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2211315A1 ES2211315A1 (es) | 2004-07-01 |
| ES2211315B1 true ES2211315B1 (es) | 2005-10-16 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200202590A Expired - Fee Related ES2211315B1 (es) | 2002-11-12 | 2002-11-12 | Nuevos compuestos triciclicos. |
| ES03779886T Expired - Lifetime ES2306906T3 (es) | 2002-11-12 | 2003-11-11 | Nuevos derivados triciclicos como antagonistas de ltd4. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03779886T Expired - Lifetime ES2306906T3 (es) | 2002-11-12 | 2003-11-11 | Nuevos derivados triciclicos como antagonistas de ltd4. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7557212B2 (enExample) |
| EP (1) | EP1560834B1 (enExample) |
| JP (1) | JP2006508116A (enExample) |
| KR (1) | KR20050074605A (enExample) |
| CN (1) | CN100379742C (enExample) |
| AT (1) | ATE399170T1 (enExample) |
| AU (1) | AU2003288032A1 (enExample) |
| BR (1) | BR0315462A (enExample) |
| CA (1) | CA2505491A1 (enExample) |
| CO (1) | CO5700775A2 (enExample) |
| DE (1) | DE60321810D1 (enExample) |
| EC (1) | ECSP055844A (enExample) |
| ES (2) | ES2211315B1 (enExample) |
| MX (1) | MXPA05005017A (enExample) |
| NO (1) | NO20052858L (enExample) |
| RU (1) | RU2330855C2 (enExample) |
| UA (1) | UA80996C2 (enExample) |
| WO (1) | WO2004043966A1 (enExample) |
| ZA (1) | ZA200503806B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| NZ551666A (en) | 2004-05-31 | 2010-07-30 | Almirall Lab | Combinations comprising antimuscarinic agents and beta-adrenergic agonists |
| ES2257152B1 (es) | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| US8207186B2 (en) | 2005-06-23 | 2012-06-26 | Merck Sharp & Dohme Corp. | Benzocycloheptapyridines as inhibitors of the receptor tyrosine kinase MET |
| CA2624656A1 (en) * | 2005-10-21 | 2007-05-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| TW200813021A (en) | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
| ES2298049B1 (es) | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| AU2012320010B2 (en) | 2011-07-26 | 2017-03-30 | Sun Pharma Advanced Research Company Ltd. | Quinoline-, quinoxaline or benzothiazole based cysteinyl leukotriene antagonists (LTD4) |
| JP2019081709A (ja) * | 2016-03-18 | 2019-05-30 | 石原産業株式会社 | 有害生物防除剤 |
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| NZ228888A (en) * | 1988-04-28 | 1991-12-23 | Schering Corp | Derivatives of piperidine, piperidylidene and piperazine and pharmaceutical compositions |
| NZ234883A (en) * | 1989-08-22 | 1995-01-27 | Merck Frosst Canada Inc | Quinolin-2-ylmethoxy indole derivatives, preparation and pharmaceutical compositions thereof |
| EP0685478B1 (en) * | 1993-02-16 | 2001-10-24 | Ube Industries, Ltd. | Quinoline derivatives |
| CO4990946A1 (es) * | 1997-11-25 | 2000-12-26 | Schering Corp | Antagonistas del receptor de trombina |
| AU2230101A (en) * | 1999-12-28 | 2001-07-09 | Ube Industries, Ltd. | Tricyclic compounds |
| JP2006151809A (ja) * | 2002-12-26 | 2006-06-15 | Ube Ind Ltd | ベンゾシクロヘプタピリジン化合物 |
-
2002
- 2002-11-12 ES ES200202590A patent/ES2211315B1/es not_active Expired - Fee Related
-
2003
- 2003-11-11 ES ES03779886T patent/ES2306906T3/es not_active Expired - Lifetime
- 2003-11-11 CN CNB2003801085261A patent/CN100379742C/zh not_active Expired - Fee Related
- 2003-11-11 KR KR1020057008474A patent/KR20050074605A/ko not_active Withdrawn
- 2003-11-11 DE DE60321810T patent/DE60321810D1/de not_active Expired - Lifetime
- 2003-11-11 CA CA002505491A patent/CA2505491A1/en not_active Abandoned
- 2003-11-11 AU AU2003288032A patent/AU2003288032A1/en not_active Abandoned
- 2003-11-11 AT AT03779886T patent/ATE399170T1/de not_active IP Right Cessation
- 2003-11-11 JP JP2004550982A patent/JP2006508116A/ja active Pending
- 2003-11-11 BR BR0315462-9A patent/BR0315462A/pt not_active IP Right Cessation
- 2003-11-11 MX MXPA05005017A patent/MXPA05005017A/es not_active Application Discontinuation
- 2003-11-11 WO PCT/EP2003/012581 patent/WO2004043966A1/en not_active Ceased
- 2003-11-11 UA UAA200505509A patent/UA80996C2/uk unknown
- 2003-11-11 RU RU2005118757/04A patent/RU2330855C2/ru not_active IP Right Cessation
- 2003-11-11 US US10/534,487 patent/US7557212B2/en not_active Expired - Fee Related
- 2003-11-11 EP EP03779886A patent/EP1560834B1/en not_active Expired - Lifetime
-
2005
- 2005-05-11 ZA ZA200503806A patent/ZA200503806B/en unknown
- 2005-06-09 EC EC2005005844A patent/ECSP055844A/es unknown
- 2005-06-10 CO CO05056627A patent/CO5700775A2/es unknown
- 2005-06-13 NO NO20052858A patent/NO20052858L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1735618A (zh) | 2006-02-15 |
| NO20052858D0 (no) | 2005-06-13 |
| AU2003288032A1 (en) | 2004-06-03 |
| EP1560834B1 (en) | 2008-06-25 |
| ES2306906T3 (es) | 2008-11-16 |
| ATE399170T1 (de) | 2008-07-15 |
| MXPA05005017A (es) | 2005-08-03 |
| US7557212B2 (en) | 2009-07-07 |
| UA80996C2 (en) | 2007-11-26 |
| CA2505491A1 (en) | 2004-05-27 |
| DE60321810D1 (de) | 2008-08-07 |
| US20060116363A1 (en) | 2006-06-01 |
| BR0315462A (pt) | 2005-08-23 |
| ES2211315A1 (es) | 2004-07-01 |
| EP1560834A1 (en) | 2005-08-10 |
| JP2006508116A (ja) | 2006-03-09 |
| ECSP055844A (es) | 2005-09-20 |
| ZA200503806B (en) | 2006-08-30 |
| CN100379742C (zh) | 2008-04-09 |
| RU2005118757A (ru) | 2006-02-27 |
| WO2004043966A1 (en) | 2004-05-27 |
| RU2330855C2 (ru) | 2008-08-10 |
| KR20050074605A (ko) | 2005-07-18 |
| NO20052858L (no) | 2005-08-12 |
| CO5700775A2 (es) | 2006-11-30 |
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