SK12082003A3 - Benzamidínové deriváty - Google Patents
Benzamidínové deriváty Download PDFInfo
- Publication number
- SK12082003A3 SK12082003A3 SK1208-2003A SK12082003A SK12082003A3 SK 12082003 A3 SK12082003 A3 SK 12082003A3 SK 12082003 A SK12082003 A SK 12082003A SK 12082003 A3 SK12082003 A3 SK 12082003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- etooc
- prodrug
- pharmacologically acceptable
- acceptable salt
- Prior art date
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- 150000003937 benzamidines Chemical class 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 285
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000005843 halogen group Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
- 230000002265 prevention Effects 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 230000023555 blood coagulation Effects 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 11
- -1 ethoxycarbonylmethanesulfonyl group Chemical group 0.000 claims description 582
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 191
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 144
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 127
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 46
- 239000000651 prodrug Substances 0.000 claims description 32
- 229940002612 prodrug Drugs 0.000 claims description 32
- BVPDYEMZSMSMSB-UHFFFAOYSA-N sulfamoyl acetate Chemical compound CC(=O)OS(N)(=O)=O BVPDYEMZSMSMSB-UHFFFAOYSA-N 0.000 claims description 27
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 15
- FUYOZIVWKHUWQX-UHFFFAOYSA-N 2-sulfamoylacetic acid Chemical compound NS(=O)(=O)CC(O)=O FUYOZIVWKHUWQX-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 206010053567 Coagulopathies Diseases 0.000 claims description 3
- 201000010849 intracranial embolism Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 125000006017 1-propenyl group Chemical group 0.000 claims description 2
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims description 2
- HPYKRLQBMUPOFA-UHFFFAOYSA-N piperidin-1-ylmethanimine Chemical compound N=CN1CCCCC1 HPYKRLQBMUPOFA-UHFFFAOYSA-N 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims 1
- GIAWKUODPZKSFJ-DUXPYHPUSA-N NC(=N)C1=CC=CC(\C=C\CN(C=2C=CC(OC3CCN(CC3)C=3OCCN=3)=CC=2)S(=O)(=O)CC(O)=O)=C1 Chemical compound NC(=N)C1=CC=CC(\C=C\CN(C=2C=CC(OC3CCN(CC3)C=3OCCN=3)=CC=2)S(=O)(=O)CC(O)=O)=C1 GIAWKUODPZKSFJ-DUXPYHPUSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 77
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 108010074860 Factor Xa Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 335
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 252
- 239000000203 mixture Substances 0.000 description 248
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 231
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 227
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 213
- 238000006243 chemical reaction Methods 0.000 description 207
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 174
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 135
- 239000011541 reaction mixture Substances 0.000 description 122
- 239000007787 solid Substances 0.000 description 114
- 239000002904 solvent Substances 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 239000000243 solution Substances 0.000 description 104
- 239000007858 starting material Substances 0.000 description 82
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 77
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 68
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 60
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 59
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 59
- 239000003480 eluent Substances 0.000 description 58
- 239000000047 product Substances 0.000 description 58
- 238000002953 preparative HPLC Methods 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 49
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
- 239000003153 chemical reaction reagent Substances 0.000 description 44
- 150000008282 halocarbons Chemical class 0.000 description 41
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 40
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 40
- 238000000034 method Methods 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
- 125000006239 protecting group Chemical group 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 30
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 29
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 29
- 238000001816 cooling Methods 0.000 description 28
- 230000035484 reaction time Effects 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 229910052783 alkali metal Inorganic materials 0.000 description 27
- 239000002585 base Substances 0.000 description 27
- 230000002411 adverse Effects 0.000 description 26
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 26
- 235000019270 ammonium chloride Nutrition 0.000 description 26
- 238000010511 deprotection reaction Methods 0.000 description 26
- 239000012442 inert solvent Substances 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 25
- 235000011114 ammonium hydroxide Nutrition 0.000 description 25
- 238000010531 catalytic reduction reaction Methods 0.000 description 25
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 24
- 238000001226 reprecipitation Methods 0.000 description 24
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 23
- 239000008096 xylene Substances 0.000 description 23
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 21
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 20
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 20
- 229940117389 dichlorobenzene Drugs 0.000 description 20
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 150000001408 amides Chemical class 0.000 description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 18
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 18
- 229910052763 palladium Inorganic materials 0.000 description 17
- 150000003462 sulfoxides Chemical class 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- 125000005129 aryl carbonyl group Chemical group 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 14
- 150000008041 alkali metal carbonates Chemical class 0.000 description 14
- 150000002576 ketones Chemical class 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 150000002825 nitriles Chemical class 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- JJNVAUCXGWMFFS-UHFFFAOYSA-N Cl.Cl.S(N)(=O)(=O)CC(=O)O Chemical compound Cl.Cl.S(N)(=O)(=O)CC(=O)O JJNVAUCXGWMFFS-UHFFFAOYSA-N 0.000 description 11
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 11
- 239000003114 blood coagulation factor Substances 0.000 description 11
- 239000003638 chemical reducing agent Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 150000007530 organic bases Chemical class 0.000 description 11
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000007800 oxidant agent Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 10
- 235000015497 potassium bicarbonate Nutrition 0.000 description 10
- 239000011736 potassium bicarbonate Substances 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 9
- 229910052808 lithium carbonate Inorganic materials 0.000 description 9
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 9
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 9
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 9
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 8
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
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- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- DBCAVMLQRAABFF-UHFFFAOYSA-M potassium;carbonic acid;hydrogen carbonate Chemical compound [K+].OC(O)=O.OC([O-])=O DBCAVMLQRAABFF-UHFFFAOYSA-M 0.000 description 1
- 239000012255 powdered metal Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
-
- A—HUMAN NECESSITIES
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- A61K31/402—1-aryl substituted, e.g. piretanide
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- A61K31/42—Oxazoles
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- A61K31/425—Thiazoles
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/48—Sulfur atoms
-
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
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- C07D223/08—Oxygen atoms
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- C07D223/12—Nitrogen atoms not forming part of a nitro radical
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- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001107615 | 2001-04-05 | ||
| PCT/JP2002/003355 WO2002081448A1 (en) | 2001-04-05 | 2002-04-03 | Benzamidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK12082003A3 true SK12082003A3 (sk) | 2004-09-08 |
Family
ID=18959909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1208-2003A SK12082003A3 (sk) | 2001-04-05 | 2002-04-03 | Benzamidínové deriváty |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7030138B2 (cs) |
| EP (1) | EP1375482A4 (cs) |
| KR (1) | KR20030087056A (cs) |
| CN (1) | CN1610666A (cs) |
| AU (1) | AU2002246336B2 (cs) |
| BR (1) | BR0208678A (cs) |
| CA (1) | CA2442904A1 (cs) |
| CO (1) | CO5550436A2 (cs) |
| CZ (1) | CZ20032728A3 (cs) |
| HU (1) | HUP0400384A3 (cs) |
| IL (1) | IL158076A0 (cs) |
| MX (1) | MXPA03009097A (cs) |
| NO (1) | NO20034439L (cs) |
| NZ (1) | NZ528517A (cs) |
| PL (1) | PL363961A1 (cs) |
| RU (1) | RU2256652C1 (cs) |
| SK (1) | SK12082003A3 (cs) |
| WO (1) | WO2002081448A1 (cs) |
| ZA (1) | ZA200307646B (cs) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10162114A1 (de) * | 2001-12-12 | 2003-06-26 | Schering Ag | Neue Amidin-Derivate und deren Verwendung in Arzneimitteln |
| GB0321781D0 (en) | 2003-09-17 | 2003-10-15 | Toppan Printing Company Ltd | Electroluminescent device |
| JP4390113B2 (ja) | 2003-11-10 | 2009-12-24 | ケンブリッジ ディスプレイ テクノロジー リミテッド | ジベンゾシロールポリマー及びその製造方法 |
| GB0329364D0 (en) | 2003-12-19 | 2004-01-21 | Cambridge Display Tech Ltd | Optical device |
| KR100804452B1 (ko) | 2004-03-31 | 2008-02-20 | 닛뽕소다 가부시키가이샤 | 환형 아민 화합물 및 유해 생물 방제제 |
| AU2005228289B2 (en) * | 2004-03-31 | 2008-01-10 | Nippon Soda Co., Ltd. | Cyclic amine compound and pest control agent |
| GB0422391D0 (en) | 2004-10-08 | 2004-11-10 | Cambridge Display Tech Ltd | Light emitting device |
| GB0427266D0 (en) | 2004-12-13 | 2005-01-12 | Cambridge Display Tech Ltd | Phosphorescent OLED |
| US9179518B2 (en) | 2004-12-24 | 2015-11-03 | Cambridge Display Technology Limited | Light emissive device |
| GB2460358B (en) | 2004-12-29 | 2010-01-13 | Cambridge Display Tech Ltd | Rigid amines |
| GB0428445D0 (en) | 2004-12-29 | 2005-02-02 | Cambridge Display Tech Ltd | Blue-shifted triarylamine polymer |
| GB0428444D0 (en) | 2004-12-29 | 2005-02-02 | Cambridge Display Tech Ltd | Conductive polymer compositions in opto-electrical devices |
| GB2426376B (en) * | 2005-05-19 | 2008-12-03 | Cdt Oxford Ltd | Light-emitting device |
| GB0514476D0 (en) | 2005-07-14 | 2005-08-17 | Cambridge Display Tech Ltd | Conductive polymer compositions in opto-electrical devices |
| US8338607B2 (en) | 2005-10-06 | 2012-12-25 | Nippon Soda Co., Ltd. | Cyclic amine compounds and agents for pest control |
| GB2433509A (en) | 2005-12-22 | 2007-06-27 | Cambridge Display Tech Ltd | Arylamine polymer |
| GB0526185D0 (en) | 2005-12-22 | 2006-02-01 | Cambridge Display Tech Ltd | Electronic device |
| GB0526393D0 (en) | 2005-12-23 | 2006-02-08 | Cdt Oxford Ltd | Light emissive device |
| GB2433833A (en) | 2005-12-28 | 2007-07-04 | Cdt Oxford Ltd | Micro-cavity OLED layer structure with transparent electrode |
| WO2007089101A1 (en) * | 2006-01-31 | 2007-08-09 | Dong Wha Pharmaceutical Ind.Co., Ltd. | Novel benzamidine derivatives, process for the preparation thereof and pharmaceutical composition comprising the same |
| GB2434916A (en) * | 2006-02-03 | 2007-08-08 | Cdt Oxford Ltd | OLED for full colour display |
| GB2434915A (en) | 2006-02-03 | 2007-08-08 | Cdt Oxford Ltd | Phosphoescent OLED for full colour display |
| GB0605120D0 (en) | 2006-03-14 | 2006-04-26 | Novartis Ag | Organic Compounds |
| GB2440934B (en) | 2006-04-28 | 2009-12-16 | Cdt Oxford Ltd | Opto-electrical polymers and devices |
| TWI442563B (zh) | 2006-08-01 | 2014-06-21 | 劍橋顯示科技有限公司 | 製造光電裝置之方法 |
| GB0617167D0 (en) * | 2006-08-31 | 2006-10-11 | Cdt Oxford Ltd | Compounds for use in opto-electrical devices |
| GB0617723D0 (en) * | 2006-09-08 | 2006-10-18 | Cambridge Display Tech Ltd | Conductive polymer compositions in opto-electrical devices |
| GB0620045D0 (en) | 2006-10-10 | 2006-11-22 | Cdt Oxford Ltd | Otpo-electrical devices and methods of making the same |
| GB2442724B (en) * | 2006-10-10 | 2009-10-21 | Cdt Oxford Ltd | Light emissive device |
| US20100249402A1 (en) * | 2007-07-27 | 2010-09-30 | Dong Wha Pharmaceutical Co. Ltd. | Novel benzamidine derivatives, process for the preparation thereof and pharmaceutical composition for preventing or treating osteporosis comprising the same |
| GB2454890B (en) | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
| GB2455747B (en) | 2007-12-19 | 2011-02-09 | Cambridge Display Tech Ltd | Electronic devices and methods of making the same using solution processing techniques |
| GB2456788B (en) | 2008-01-23 | 2011-03-09 | Cambridge Display Tech Ltd | White light emitting material |
| GB2466730B (en) * | 2008-01-23 | 2011-04-20 | Cambridge Display Tech Ltd | Phosphorescent compositions and their use in displays |
| GB2458454B (en) | 2008-03-14 | 2011-03-16 | Cambridge Display Tech Ltd | Electronic devices and methods of making the same using solution processing techniques |
| GB2459895B (en) | 2008-05-09 | 2011-04-27 | Cambridge Display Technology Limited | Organic light emissive device |
| AU2009253078B2 (en) * | 2008-05-30 | 2014-04-17 | Novo Nordisk Health Care Ag | Method of controlling a polypeptide modification reaction |
| GB2461527B (en) * | 2008-07-01 | 2011-08-03 | Limited Cambridge Display Technology | Organic electronic device |
| GB2462410B (en) | 2008-07-21 | 2011-04-27 | Cambridge Display Tech Ltd | Compositions and methods for manufacturing light-emissive devices |
| GB2462122B (en) | 2008-07-25 | 2013-04-03 | Cambridge Display Tech Ltd | Electroluminescent materials |
| GB2462314B (en) | 2008-08-01 | 2011-03-16 | Cambridge Display Tech Ltd | Organic light-emiting materials and devices |
| GB0814161D0 (en) | 2008-08-01 | 2008-09-10 | Cambridge Display Tech Ltd | Blue-light emitting material |
| GB0814971D0 (en) | 2008-08-15 | 2008-09-24 | Cambridge Display Tech Ltd | Opto-electrical devices and methods of manufacturing the same |
| GB2462688B (en) * | 2008-08-22 | 2012-03-07 | Cambridge Display Tech Ltd | Opto-electrical devices and methods of manufacturing the same |
| GB2469498B (en) | 2009-04-16 | 2012-03-07 | Cambridge Display Tech Ltd | Polymer and polymerisation method |
| GB2469497B (en) | 2009-04-16 | 2012-04-11 | Cambridge Display Tech Ltd | Polymers comprising fluorene derivative repeat units and their preparation |
| GB0906554D0 (en) | 2009-04-16 | 2009-05-20 | Cambridge Display Tech Ltd | Organic electroluminescent device |
| GB2469500B (en) | 2009-04-16 | 2012-06-06 | Cambridge Display Tech Ltd | Method of forming a polymer |
| GB2475247B (en) | 2009-11-10 | 2012-06-13 | Cambridge Display Tech Ltd | Organic optoelectronic device and method |
| GB2475246B (en) | 2009-11-10 | 2012-02-29 | Cambridge Display Tech Ltd | Organic opto-electronic device and method |
| GB2484253B (en) | 2010-05-14 | 2013-09-11 | Cambridge Display Tech Ltd | Organic light-emitting composition and device |
| GB2487342B (en) | 2010-05-14 | 2013-06-19 | Cambridge Display Tech Ltd | Host polymer comprising conjugated repeat units and non-conjugated repeat units for light-emitting compositions, and organic light-emitting devices |
| GB2485001A (en) | 2010-10-19 | 2012-05-02 | Cambridge Display Tech Ltd | OLEDs |
| GB201122316D0 (en) | 2011-12-23 | 2012-02-01 | Cambridge Display Tech Ltd | Polymer, polymer composition and organic light-emitting device |
| GB2494096B (en) | 2011-01-31 | 2013-12-18 | Cambridge Display Tech Ltd | Polymer |
| CN103339167B (zh) | 2011-01-31 | 2018-01-12 | 剑桥显示技术有限公司 | 聚合物 |
| GB201105582D0 (en) | 2011-04-01 | 2011-05-18 | Cambridge Display Tech Ltd | Organic light-emitting device and method |
| GB201107905D0 (en) | 2011-05-12 | 2011-06-22 | Cambridge Display Tech Ltd | Light-emitting material, composition and device |
| GB201110564D0 (en) | 2011-06-22 | 2011-08-03 | Cambridge Display Tech Ltd | Polymer and optoelectronic device |
| WO2013005028A1 (en) | 2011-07-04 | 2013-01-10 | Cambridge Display Technology Limited | Organic light emitting device and fabrication method thereof |
| GB201111742D0 (en) | 2011-07-08 | 2011-08-24 | Cambridge Display Tech Ltd | Solution |
| GB201210131D0 (en) | 2011-11-02 | 2012-07-25 | Cambridge Display Tech Ltd | Light emitting composition and device |
| GB201118997D0 (en) | 2011-11-03 | 2011-12-14 | Cambridge Display Tech Ltd | Electronic device and method |
| GB201200619D0 (en) | 2012-01-16 | 2012-02-29 | Cambridge Display Tech Ltd | Polymer |
| GB2515909B (en) | 2012-01-31 | 2020-07-15 | Cambridge Display Tech Ltd | Composition comprising a fluorescent light-emitting material and triplet-accepting polymer and use thereof |
| GB2508410A (en) | 2012-11-30 | 2014-06-04 | Cambridge Display Tech Ltd | Polymer and organic electronic device |
| GB2514818B (en) | 2013-06-05 | 2015-12-16 | Cambridge Display Tech Ltd | Polymer and organic electronic device |
| US12092597B2 (en) * | 2021-12-03 | 2024-09-17 | Palo Alto Research Center Incorporated | Arylphosphine nanomaterial constructs for moisture-insensitive formaldehyde gas sensing |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2004A (en) * | 1841-03-12 | Improvement in the manner of constructing and propelling steam-vessels | ||
| ZA928276B (en) | 1991-10-31 | 1993-05-06 | Daiichi Seiyaku Co | Aromatic amidine derivates and salts thereof. |
| PL184824B1 (pl) | 1994-12-02 | 2002-12-31 | Yamanouchi Pharmaceu | Pochodne amidynonaftylowe oraz ich sole oraz kompozycja farmaceutyczna zawierająca pochodną amidynonaftylową lub jej sól |
| TW542822B (en) | 1997-01-17 | 2003-07-21 | Ajinomoto Kk | Benzamidine derivatives |
| AU4166400A (en) | 1999-02-11 | 2000-08-29 | Cor Therapeutics, Inc. | Alkenyl and alkynyl compounds as inhibitors of factor xa |
| US6350761B1 (en) * | 1999-07-30 | 2002-02-26 | Berlex Laboratories, Inc. | Benzenamine derivatives as anti-coagulants |
| MXPA02004218A (es) * | 1999-10-28 | 2002-10-17 | Sankyo Co | Derivados de benzamidina. |
-
2002
- 2002-04-03 PL PL02363961A patent/PL363961A1/xx not_active Application Discontinuation
- 2002-04-03 WO PCT/JP2002/003355 patent/WO2002081448A1/ja not_active Ceased
- 2002-04-03 KR KR10-2003-7012987A patent/KR20030087056A/ko not_active Ceased
- 2002-04-03 CZ CZ20032728A patent/CZ20032728A3/cs unknown
- 2002-04-03 RU RU2003129502/04A patent/RU2256652C1/ru not_active IP Right Cessation
- 2002-04-03 IL IL15807602A patent/IL158076A0/xx unknown
- 2002-04-03 CN CNA028111052A patent/CN1610666A/zh active Pending
- 2002-04-03 NZ NZ528517A patent/NZ528517A/en unknown
- 2002-04-03 AU AU2002246336A patent/AU2002246336B2/en not_active Ceased
- 2002-04-03 HU HU0400384A patent/HUP0400384A3/hu unknown
- 2002-04-03 BR BR0208678-6A patent/BR0208678A/pt not_active IP Right Cessation
- 2002-04-03 SK SK1208-2003A patent/SK12082003A3/sk not_active Application Discontinuation
- 2002-04-03 CA CA002442904A patent/CA2442904A1/en not_active Abandoned
- 2002-04-03 EP EP02714444A patent/EP1375482A4/en not_active Withdrawn
- 2002-04-03 MX MXPA03009097A patent/MXPA03009097A/es unknown
-
2003
- 2003-09-30 ZA ZA200307646A patent/ZA200307646B/xx unknown
- 2003-10-03 NO NO20034439A patent/NO20034439L/no not_active Application Discontinuation
- 2003-10-03 US US10/679,215 patent/US7030138B2/en not_active Expired - Fee Related
- 2003-11-04 CO CO03097568A patent/CO5550436A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0400384A3 (en) | 2008-08-28 |
| CN1610666A (zh) | 2005-04-27 |
| ZA200307646B (en) | 2004-07-13 |
| NO20034439D0 (no) | 2003-10-03 |
| WO2002081448A1 (en) | 2002-10-17 |
| US7030138B2 (en) | 2006-04-18 |
| BR0208678A (pt) | 2004-03-30 |
| PL363961A1 (en) | 2004-11-29 |
| CO5550436A2 (es) | 2005-08-31 |
| NZ528517A (en) | 2004-08-27 |
| RU2003129502A (ru) | 2005-04-10 |
| CA2442904A1 (en) | 2002-10-17 |
| EP1375482A4 (en) | 2005-01-19 |
| RU2256652C1 (ru) | 2005-07-20 |
| NO20034439L (no) | 2003-12-02 |
| HUP0400384A2 (hu) | 2004-09-28 |
| KR20030087056A (ko) | 2003-11-12 |
| IL158076A0 (en) | 2004-03-28 |
| EP1375482A1 (en) | 2004-01-02 |
| CZ20032728A3 (cs) | 2004-02-18 |
| MXPA03009097A (es) | 2004-02-12 |
| US20040147555A1 (en) | 2004-07-29 |
| AU2002246336B2 (en) | 2005-05-19 |
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