CA2666177A1 - Acylaminoimidazoles et acylaminothiazoles - Google Patents

Acylaminoimidazoles et acylaminothiazoles Download PDF

Info

Publication number: CA2666177A1
Authority: CA; Canada
Prior art keywords: alkyl; substituents; another; substituted; group
Prior art date: 2006-10-11
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.): Abandoned

Application number

CA002666177A

Other languages

English (en)

Inventor

Marcus Bauser

Anja Buchmueller

Georges Von Degenfeld

Elke Dittrich-Wengenroth

Christoph Gerdes

Mark Jean Gnoth

Dirk Gottschling

Stefan Heitmeier

Martin Hendrix

Johannes Koebberling

Dieter Lang

Ulrich Rester

Uwe Saatmann

Adrian Tersteegen

Astrid Bruens

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Individual

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

2006-10-11

Filing date

2007-10-10

Publication date

2008-04-17

2007-10-10 Application filed by Individual filed Critical Individual

2008-04-17 Publication of CA2666177A1 publication Critical patent/CA2666177A1/fr

Status Abandoned legal-status Critical Current

Links

-1 acyl aminoimidazoles Chemical class 0.000 claims abstract description 113
238000011282 treatment Methods 0.000 claims abstract description 21
239000003814 drug Substances 0.000 claims abstract description 17
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 116
125000001424 substituent group Chemical group 0.000 claims description 104
150000001875 compounds Chemical class 0.000 claims description 98
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical class 0.000 claims description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 23
239000012453 solvate Substances 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
230000008569 process Effects 0.000 claims description 16
238000011321 prophylaxis Methods 0.000 claims description 15
230000009424 thromboembolic effect Effects 0.000 claims description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 12
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 7
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
239000011737 fluorine Substances 0.000 claims description 5
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
208000001435 Thromboembolism Diseases 0.000 abstract description 4
230000006806 disease prevention Effects 0.000 abstract 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 160
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
239000000243 solution Substances 0.000 description 103
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
239000000047 product Substances 0.000 description 92
238000004128 high performance liquid chromatography Methods 0.000 description 87
238000005160 1H NMR spectroscopy Methods 0.000 description 84
239000000203 mixture Substances 0.000 description 66
230000002829 reductive effect Effects 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 37
239000002904 solvent Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
238000012360 testing method Methods 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 31
239000000126 substance Substances 0.000 description 30
108090000190 Thrombin Proteins 0.000 description 27
239000012074 organic phase Substances 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 27
238000002953 preparative HPLC Methods 0.000 description 26
229960004072 thrombin Drugs 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 14
229910000069 nitrogen hydride Inorganic materials 0.000 description 14
239000012071 phase Substances 0.000 description 14
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 13
238000010626 work up procedure Methods 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
229910052796 boron Inorganic materials 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
210000004369 blood Anatomy 0.000 description 11
239000008280 blood Substances 0.000 description 11
230000015271 coagulation Effects 0.000 description 11
238000005345 coagulation Methods 0.000 description 11
208000035475 disorder Diseases 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
239000000725 suspension Substances 0.000 description 11
208000032843 Hemorrhage Diseases 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000002585 base Substances 0.000 description 10
238000012512 characterization method Methods 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
WUAXWQRULBZETB-UHFFFAOYSA-N homoveratric acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC WUAXWQRULBZETB-UHFFFAOYSA-N 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000001994 activation Methods 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
229910052786 argon Inorganic materials 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
208000034158 bleeding Diseases 0.000 description 9
230000000740 bleeding effect Effects 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000004913 activation Effects 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000758 substrate Substances 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
238000005259 measurement Methods 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003146 anticoagulant agent Substances 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
230000023555 blood coagulation Effects 0.000 description 6
229960001701 chloroform Drugs 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
229960002897 heparin Drugs 0.000 description 6
229920000669 heparin Polymers 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000000746 purification Methods 0.000 description 6
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
210000001772 blood platelet Anatomy 0.000 description 5
230000023597 hemostasis Effects 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
JGLXMVNPZCCPSZ-UHFFFAOYSA-N n-(2,5-diphenyl-1h-imidazol-4-yl)-2-(propan-2-ylamino)acetamide Chemical compound CC(C)NCC(=O)NC=1N=C(C=2C=CC=CC=2)NC=1C1=CC=CC=C1 JGLXMVNPZCCPSZ-UHFFFAOYSA-N 0.000 description 5
229910000343 potassium bisulfate Inorganic materials 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000000825 ultraviolet detection Methods 0.000 description 5
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
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 4
BWGQQHQHZJMKJY-UHFFFAOYSA-N 2-(5-fluorothiophen-2-yl)-5-phenyl-1h-imidazol-4-amine Chemical compound NC=1N=C(C=2SC(F)=CC=2)NC=1C1=CC=CC=C1 BWGQQHQHZJMKJY-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
108010074860 Factor Xa Proteins 0.000 description 4
102000009123 Fibrin Human genes 0.000 description 4
108010073385 Fibrin Proteins 0.000 description 4
BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
108010000499 Thromboplastin Proteins 0.000 description 4
102000002262 Thromboplastin Human genes 0.000 description 4
208000007536 Thrombosis Diseases 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000004087 circulation Effects 0.000 description 4
230000002255 enzymatic effect Effects 0.000 description 4
WZKCZNJTDZCNMH-UHFFFAOYSA-N ethyl 2-(3,4-dimethoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC)=C1 WZKCZNJTDZCNMH-UHFFFAOYSA-N 0.000 description 4
229950003499 fibrin Drugs 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000001802 infusion Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000002265 prevention Effects 0.000 description 4
MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
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125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
230000018341 negative regulation of fibrinolysis Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
230000000626 neurodegenerative effect Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
231100000915 pathological change Toxicity 0.000 description 1
230000036285 pathological change Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000001175 peptic effect Effects 0.000 description 1
238000005897 peptide coupling reaction Methods 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960004923 phenprocoumon Drugs 0.000 description 1
DQDAYGNAKTZFIW-UHFFFAOYSA-N phenprocoumon Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=CC=C1 DQDAYGNAKTZFIW-UHFFFAOYSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000003757 phosphotransferase inhibitor Substances 0.000 description 1
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
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229940127126 plasminogen activator Drugs 0.000 description 1
239000002797 plasminogen activator inhibitor Substances 0.000 description 1
230000010118 platelet activation Effects 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000031915 positive regulation of coagulation Effects 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000009979 protective mechanism Effects 0.000 description 1
229960000856 protein c Drugs 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000008844 regulatory mechanism Effects 0.000 description 1
210000002796 renal vein Anatomy 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
238000012552 review Methods 0.000 description 1
ILAROKYJDCBZHJ-UHFFFAOYSA-N s-[(2,4-dimethoxyphenyl)methyl] 5-chlorothiophene-2-carbothioate Chemical compound COC1=CC(OC)=CC=C1CSC(=O)C1=CC=C(Cl)S1 ILAROKYJDCBZHJ-UHFFFAOYSA-N 0.000 description 1
150000003354 serine derivatives Chemical class 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
SLZHLQUFNFXTHB-UHFFFAOYSA-M sodium;5-butan-2-yl-5-ethyl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].CCC(C)C1(CC)C([O-])=NC(=S)NC1=O SLZHLQUFNFXTHB-UHFFFAOYSA-M 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
230000008961 swelling Effects 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000011975 tartaric acid Chemical class 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
108010008704 tert-butoxycarbonyl-isoleucyl-glutamyl-glycyl-arginyl-amidomethylcoumarin Proteins 0.000 description 1
KKRHSODPKYQHDS-CQSZACIVSA-N tert-butyl (4s)-4-[[2-(5-fluorothiophen-2-yl)-5-phenyl-1h-imidazol-4-yl]carbamoyl]-1,3-thiazolidine-3-carboxylate Chemical compound CC(C)(C)OC(=O)N1CSC[C@@H]1C(=O)NC1=C(C=2C=CC=CC=2)NC(C=2SC(F)=CC=2)=N1 KKRHSODPKYQHDS-CQSZACIVSA-N 0.000 description 1
QLSLTMCWDVXFMD-UHFFFAOYSA-N tert-butyl 3-(3,4-dimethoxyphenyl)-4-[[2-[[2-(5-fluorothiophen-2-yl)-5-phenyl-1h-imidazol-4-yl]amino]-2-oxoethyl]-propan-2-ylamino]-4-oxobutanoate Chemical compound C1=C(OC)C(OC)=CC=C1C(CC(=O)OC(C)(C)C)C(=O)N(C(C)C)CC(=O)NC1=C(C=2C=CC=CC=2)NC(C=2SC(F)=CC=2)=N1 QLSLTMCWDVXFMD-UHFFFAOYSA-N 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
150000007979 thiazole derivatives Chemical class 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
238000013169 thromboelastometry Methods 0.000 description 1
230000002885 thrombogenetic effect Effects 0.000 description 1
229960000103 thrombolytic agent Drugs 0.000 description 1
201000005665 thrombophilia Diseases 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
208000004043 venous thromboembolism Diseases 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
229940019333 vitamin k antagonists Drugs 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

CA002666177A 2006-10-11 2007-10-10 Acylaminoimidazoles et acylaminothiazoles Abandoned CA2666177A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE102006048042A DE102006048042A1 (de)	2006-10-11	2006-10-11	Acylaminoimidazole und Acylaminothiazole
DE102006048042.2		2006-10-11
PCT/EP2007/008789 WO2008043533A2 (fr)	2006-10-11	2007-10-10	Acylaminoimidazoles et acylaminothiazoles

Publications (1)

Publication Number	Publication Date
CA2666177A1 true CA2666177A1 (fr)	2008-04-17

Family

ID=39184814

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002666177A Abandoned CA2666177A1 (fr)	2006-10-11	2007-10-10	Acylaminoimidazoles et acylaminothiazoles

Country Status (5)

Country	Link
EP (1)	EP2079708A2 (fr)
JP (1)	JP2010505896A (fr)
CA (1)	CA2666177A1 (fr)
DE (1)	DE102006048042A1 (fr)
WO (1)	WO2008043533A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8044069B2 (en)	2008-10-02	2011-10-25	Abbott Laboratories	Compounds as calcium channel blockers
US8815869B2 (en)	2010-03-18	2014-08-26	Abbvie Inc.	Lactam acetamides as calcium channel blockers
JP2015083542A (ja) *	2012-02-08	2015-04-30	大日本住友製薬株式会社	３位置換プロリン誘導体
WO2015104605A1 (fr) *	2014-01-08	2015-07-16	Wockhardt Limited	Procédé de préparation de rivaroxaban ou d'un sel pharmaceutiquement acceptable de ce dernier
SMT202200134T1 (it)	2018-03-08	2022-05-12	Incyte Corp	Composti di amminopirazindiolo come inibitori di pi3k-y
WO2020010003A1 (fr)	2018-07-02	2020-01-09	Incyte Corporation	DÉRIVÉS D'AMINOPYRAZINE UTILISÉS EN TANT QU'INHIBITEURS DE PI3K-γ

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2842523A1 (fr) *	2002-07-17	2004-01-23	Sanofi Synthelabo	Derives d'acylaminothiazole, leur preparation et leur application en therapeutique
DE602005007717D1 (de) *	2004-03-23	2008-08-07	Pfizer Prod Inc	Imidazolverbindungen zur behandlung von neurodegenerativen erkrankungen
DE102006001574A1 (de) *	2006-01-12	2007-07-19	Bayer Healthcare Ag	Acylaminoimidazole

2006
- 2006-10-11 DE DE102006048042A patent/DE102006048042A1/de not_active Withdrawn
2007
- 2007-10-10 EP EP07818862A patent/EP2079708A2/fr not_active Withdrawn
- 2007-10-10 WO PCT/EP2007/008789 patent/WO2008043533A2/fr not_active Ceased
- 2007-10-10 CA CA002666177A patent/CA2666177A1/fr not_active Abandoned
- 2007-10-10 JP JP2009531766A patent/JP2010505896A/ja active Pending

Also Published As

Publication number	Publication date
WO2008043533A3 (fr)	2008-07-03
JP2010505896A (ja)	2010-02-25
WO2008043533A2 (fr)	2008-04-17
DE102006048042A1 (de)	2008-04-17
EP2079708A2 (fr)	2009-07-22

Publication	Publication Date	Title
RU2660421C2 (ru)	2018-07-06	Бензиламиновые производные
CA2666401A1 (fr)	2008-04-24	Acylaminopyrazoles destines au traitement de maladies cardiovasculaires
JP4598771B2 (ja)	2010-12-15	複素環式化合物
US20100105663A1 (en)	2010-04-29	2-(heteroaryl) alkyl indazole 6-phenyl and thienyl methyl amide as thrombin inhibitors
CA2666177A1 (fr)	2008-04-17	Acylaminoimidazoles et acylaminothiazoles
RU2605600C2 (ru)	2016-12-27	Амино-замещенные производные 3-гетероароиламинопропионовой кислоты и их применение в качестве фармацевтических средств
US20160244437A1 (en)	2016-08-25	Substituted phenylalanine derivatives
CA2653666C (fr)	2014-09-16	Heterocycles substitues par un aryle et leur utilisation
KR20160064100A (ko)	2016-06-07	치환된 페닐알라닌 유도체
US20160237067A1 (en)	2016-08-18	Substituted phenylalanine derivatives
HUT76484A (en)	1997-09-29	Novel tetrasubstituted imidazole derivatives, method for preparing same, and pharmaceutical compositions containing same
EP2173744A1 (fr)	2010-04-14	(oxazolidinon-5-yl-méthyl)-2-thiophène-carboxamides substitués et leur utilisation dans le domaine de la coagulation sanguine
WO2007140982A1 (fr)	2007-12-13	Benzoxazole substitué
TWI740903B (zh)	2021-10-01	新穎吡咯啶衍生物
JP2009507055A (ja)	2009-02-19	イミノオキサゾリジン誘導体およびその使用
WO2007082666A1 (fr)	2007-07-26	Acylaminoimidazoles
CA2653665A1 (fr)	2007-12-06	Derives d'isoindoline-1-one, d'isoindoline-3-one et d'isoindoline-1,3- dione et leur utilisation
CA2653673A1 (fr)	2007-12-06	Derives d'isoindolin-1-one, d'isoindolin-3-one et d' isoindoline-1,3-dione et leur utilisation
CA2653670A1 (fr)	2007-12-06	Heterocycles substitues et son utilisation

Legal Events

Date	Code	Title	Description
2011-10-11	FZDE	Dead