DE102005049385A1 - Imidazolderivate als Inhibitoren von TAFIa - Google Patents
Imidazolderivate als Inhibitoren von TAFIa Download PDFInfo
- Publication number
- DE102005049385A1 DE102005049385A1 DE102005049385A DE102005049385A DE102005049385A1 DE 102005049385 A1 DE102005049385 A1 DE 102005049385A1 DE 102005049385 A DE102005049385 A DE 102005049385A DE 102005049385 A DE102005049385 A DE 102005049385A DE 102005049385 A1 DE102005049385 A1 DE 102005049385A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- compound
- formula
- unsubstituted
- oxadiazolyl
- 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.)
- Withdrawn
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- 239000003112 inhibitor Substances 0.000 title abstract description 17
- 150000002460 imidazoles Chemical class 0.000 title 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 208000005189 Embolism Diseases 0.000 claims abstract description 6
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 238000011321 prophylaxis Methods 0.000 claims abstract description 4
- 230000009863 secondary prevention Effects 0.000 claims abstract description 4
- 201000005665 thrombophilia Diseases 0.000 claims abstract description 4
- -1 benzimidazalinyl Chemical group 0.000 claims description 210
- 238000000034 method Methods 0.000 claims description 70
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 21
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 21
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 21
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 21
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 21
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 21
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 21
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 21
- 125000002971 oxazolyl group Chemical group 0.000 claims description 21
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001544 thienyl group Chemical group 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims description 15
- 229940125670 thienopyridine Drugs 0.000 claims description 15
- 239000002175 thienopyridine Substances 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 8
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000005512 benztetrazolyl group Chemical group 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 8
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000005438 isoindazolyl group Chemical group 0.000 claims description 8
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 8
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 8
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 8
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 8
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 8
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 102000009123 Fibrin Human genes 0.000 claims description 7
- 108010073385 Fibrin Proteins 0.000 claims description 7
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 229950003499 fibrin Drugs 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 238000001356 surgical procedure Methods 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- WQINGXHBCDXEMA-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NOC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=N1 WQINGXHBCDXEMA-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 230000005526 G1 to G0 transition Effects 0.000 claims description 5
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002785 azepinyl group Chemical group 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 239000003880 polar aprotic solvent Substances 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000004623 carbolinyl group Chemical group 0.000 claims description 4
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 4
- 125000000532 dioxanyl group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000003838 furazanyl group Chemical group 0.000 claims description 4
- 230000002439 hemostatic effect Effects 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 4
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- VQSYFXGKPXAZDE-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NN=C(C2CC2)S1 VQSYFXGKPXAZDE-UHFFFAOYSA-N 0.000 claims description 3
- WJYLALUIJRBXNY-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NOC(C=2C=CC=CC=2)=N1 WJYLALUIJRBXNY-UHFFFAOYSA-N 0.000 claims description 3
- JZHRFXBDACOBLH-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-phenyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NN=C(C=2C=CC=CC=2)S1 JZHRFXBDACOBLH-UHFFFAOYSA-N 0.000 claims description 3
- PSYRPDLOGLGUHE-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-tert-butyl-1,2,4-oxadiazol-3-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound O1C(C(C)(C)C)=NC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=N1 PSYRPDLOGLGUHE-UHFFFAOYSA-N 0.000 claims description 3
- LTGZLPZWHMBCQQ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-tert-butyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound S1C(C(C)(C)C)=NN=C1CN1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 LTGZLPZWHMBCQQ-UHFFFAOYSA-N 0.000 claims description 3
- PYJFDCFRJHWHCG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-thiophen-2-yl-1,2-oxazol-3-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NOC(C=2SC=CC=2)=C1 PYJFDCFRJHWHCG-UHFFFAOYSA-N 0.000 claims description 3
- WPDRFDYTKSCKEW-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=NOC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=N1 WPDRFDYTKSCKEW-UHFFFAOYSA-N 0.000 claims description 3
- ZKWUKBXVMGZSRK-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(2-methyl-1,3-thiazol-4-yl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound S1C(C)=NC(C=2ON=C(CN3C=C(N=C3)C(CC=3C=NC(N)=CC=3)C(O)=O)C=2)=C1 ZKWUKBXVMGZSRK-UHFFFAOYSA-N 0.000 claims description 3
- KVOZMFOBFOLFLZ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(3,4-dichlorophenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NOC(C=2C=C(Cl)C(Cl)=CC=2)=C1 KVOZMFOBFOLFLZ-UHFFFAOYSA-N 0.000 claims description 3
- IZXUZHFDRLSZAH-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(3-methylbutyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound O1C(CCC(C)C)=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=N1 IZXUZHFDRLSZAH-UHFFFAOYSA-N 0.000 claims description 3
- CMKGJKIHQGWHGW-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NN=C(C=2C=CC(Cl)=CC=2)S1 CMKGJKIHQGWHGW-UHFFFAOYSA-N 0.000 claims description 3
- DBDCBAFMUMXVJC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(S1)=NN=C1CN1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 DBDCBAFMUMXVJC-UHFFFAOYSA-N 0.000 claims description 3
- LFERXLIMRAUJHG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NN=C(C=2SC(Cl)=CC=2)S1 LFERXLIMRAUJHG-UHFFFAOYSA-N 0.000 claims description 3
- ZYOCPUYBELPPGY-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NOC(C=2C=C(C=CC=2)C(F)(F)F)=N1 ZYOCPUYBELPPGY-UHFFFAOYSA-N 0.000 claims description 3
- TYVOTXDOJSUWPZ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NOC(C=2C=CC(=CC=2)C(F)(F)F)=N1 TYVOTXDOJSUWPZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 3
- 238000001212 derivatisation Methods 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002669 lysines Chemical group 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- BGPQBVSYPNMCPL-UHFFFAOYSA-N methyl 3-(6-aminopyridin-3-yl)-2-[1-[(5-phenyl-1,2-oxazol-3-yl)methyl]imidazol-4-yl]propanoate Chemical compound C=1N(CC2=NOC(=C2)C=2C=CC=CC=2)C=NC=1C(C(=O)OC)CC1=CC=C(N)N=C1 BGPQBVSYPNMCPL-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000018341 negative regulation of fibrinolysis Effects 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 229940127126 plasminogen activator Drugs 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- FOEYMRPOKBCNCR-UHFFFAOYSA-N spiro[2.5]octane Chemical compound C1CC11CCCCC1 FOEYMRPOKBCNCR-UHFFFAOYSA-N 0.000 description 1
- IWDANOJGJIFBEL-UHFFFAOYSA-N spiro[3.4]octane Chemical compound C1CCC21CCCC2 IWDANOJGJIFBEL-UHFFFAOYSA-N 0.000 description 1
- VMWOETMUNAQFAX-UHFFFAOYSA-N spiro[3.5]nonane Chemical compound C1CCC21CCCCC2 VMWOETMUNAQFAX-UHFFFAOYSA-N 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- AEXDMFVPDVVSQJ-UHFFFAOYSA-N trifluoro(trifluoromethylsulfonyl)methane Chemical compound FC(F)(F)S(=O)(=O)C(F)(F)F AEXDMFVPDVVSQJ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005049385A DE102005049385A1 (de) | 2005-10-15 | 2005-10-15 | Imidazolderivate als Inhibitoren von TAFIa |
| JP2008534894A JP5266053B2 (ja) | 2005-10-15 | 2006-09-30 | ＴＡＦＩａのインヒビターとしてのイミダゾール誘導体 |
| PCT/EP2006/009500 WO2007045339A1 (de) | 2005-10-15 | 2006-09-30 | Imidazolderivate als inhibitoren von tafi-a |
| PT67923276T PT1937673E (pt) | 2005-10-15 | 2006-09-30 | Derivados de imidazol como derivados do tafi-a |
| SI200632014T SI1937673T1 (sl) | 2005-10-15 | 2006-09-30 | Imidazolovi derivati kot inhibitorji TAFIa |
| HUE06792327A HUE026577T2 (hu) | 2005-10-15 | 2006-09-30 | Imidazol-származékok mint TAFI-a inhibitorok |
| ES06792327.6T ES2558874T3 (es) | 2005-10-15 | 2006-09-30 | Derivados de imidazol como inhibidores de TAFIa |
| PL06792327T PL1937673T3 (pl) | 2005-10-15 | 2006-09-30 | Pochodne imidazolu jako inhibitory TAFI-A |
| EP06792327.6A EP1937673B1 (de) | 2005-10-15 | 2006-09-30 | Imidazolderivate als inhibitoren von tafi-a |
| DK06792327.6T DK1937673T3 (en) | 2005-10-15 | 2006-09-30 | Imidazolderivater som hæmmere af tafi-a |
| US12/102,105 US8044208B2 (en) | 2005-10-15 | 2008-04-14 | Imidazole derivatives as inhibitors of TAFIa |
| CY20161100053T CY1117379T1 (el) | 2005-10-15 | 2016-01-20 | Παραγωγα ιμιδαζολιου ως αναστολεις toy tafi-a |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005049385A DE102005049385A1 (de) | 2005-10-15 | 2005-10-15 | Imidazolderivate als Inhibitoren von TAFIa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005049385A1 true DE102005049385A1 (de) | 2007-04-19 |
Family
ID=37733974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005049385A Withdrawn DE102005049385A1 (de) | 2005-10-15 | 2005-10-15 | Imidazolderivate als Inhibitoren von TAFIa |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8044208B2 (https=) |
| EP (1) | EP1937673B1 (https=) |
| JP (1) | JP5266053B2 (https=) |
| CY (1) | CY1117379T1 (https=) |
| DE (1) | DE102005049385A1 (https=) |
| DK (1) | DK1937673T3 (https=) |
| ES (1) | ES2558874T3 (https=) |
| HU (1) | HUE026577T2 (https=) |
| PL (1) | PL1937673T3 (https=) |
| PT (1) | PT1937673E (https=) |
| SI (1) | SI1937673T1 (https=) |
| WO (1) | WO2007045339A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2566475A4 (en) * | 2010-05-03 | 2014-03-19 | Sk Biopharmaceuticals Co Ltd | PHARMACEUTICAL COMPOSITIONS FOR INHIBITING APOPTOSIS OF NEURONS OR NERVOUS GENERATION |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009103432A2 (en) * | 2008-02-21 | 2009-08-27 | Sanofi-Aventis | Covalently binding imaging probes |
| NZ592764A (en) * | 2008-10-29 | 2012-08-31 | Taisho Pharmaceutical Co Ltd | Compound having tafia inhibitory activity |
| DK2548871T3 (da) | 2010-03-18 | 2017-11-06 | Daiichi Sankyo Co Ltd | Cycloalkylsubstitueret imidazolderivat |
| KR20130006620A (ko) * | 2010-03-18 | 2013-01-17 | 다이이찌 산쿄 가부시키가이샤 | 시클로프로판카르복실산 유도체 |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| CA2914533A1 (en) | 2013-06-10 | 2014-12-18 | Sanofi | Macrocyclic urea derivatives as inhibitors of tafia, their preparation and their use as pharmaceuticals |
| AU2020407664A1 (en) | 2019-12-20 | 2022-08-18 | Tenaya Therapeutics, Inc. | Fluoroalkyl-oxadiazoles and uses thereof |
| AU2022270657A1 (en) | 2021-05-04 | 2023-11-16 | Tenaya Therapeutics, Inc. | 2-fluoroalkyl-1,3,4-oxadiazol-5-yl-thiazol, hdac6 inhibitors for use in the treatment of metabolic disease and hfpef |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL361054A1 (en) * | 2000-08-17 | 2004-09-20 | Pfizer Inc. | Substituted imidazoles as tafia inhibitors |
| WO2003013526A1 (en) * | 2001-08-08 | 2003-02-20 | Merck & Co. Inc. | Anticoagulant compounds |
| WO2003061653A1 (en) * | 2002-01-22 | 2003-07-31 | Pfizer Limited | 3-(imidazolyl)-2-aminopropanoic acids for use as tafi-a inhibitors for the treatment of thrombotic diseases |
-
2005
- 2005-10-15 DE DE102005049385A patent/DE102005049385A1/de not_active Withdrawn
-
2006
- 2006-09-30 EP EP06792327.6A patent/EP1937673B1/de not_active Not-in-force
- 2006-09-30 HU HUE06792327A patent/HUE026577T2/hu unknown
- 2006-09-30 ES ES06792327.6T patent/ES2558874T3/es active Active
- 2006-09-30 PT PT67923276T patent/PT1937673E/pt unknown
- 2006-09-30 WO PCT/EP2006/009500 patent/WO2007045339A1/de not_active Ceased
- 2006-09-30 JP JP2008534894A patent/JP5266053B2/ja not_active Expired - Fee Related
- 2006-09-30 SI SI200632014T patent/SI1937673T1/sl unknown
- 2006-09-30 PL PL06792327T patent/PL1937673T3/pl unknown
- 2006-09-30 DK DK06792327.6T patent/DK1937673T3/en active
-
2008
- 2008-04-14 US US12/102,105 patent/US8044208B2/en not_active Expired - Fee Related
-
2016
- 2016-01-20 CY CY20161100053T patent/CY1117379T1/el unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2566475A4 (en) * | 2010-05-03 | 2014-03-19 | Sk Biopharmaceuticals Co Ltd | PHARMACEUTICAL COMPOSITIONS FOR INHIBITING APOPTOSIS OF NEURONS OR NERVOUS GENERATION |
| US8841335B2 (en) | 2010-05-03 | 2014-09-23 | Sk Biopharmaceuticals Co., Ltd. | Pharmaceutical composition for inhibiting apoptosis of neuron or neurodegeneration |
| AU2011249223B2 (en) * | 2010-05-03 | 2014-12-11 | Sk Biopharmaceuticals Co., Ltd. | Pharmaceutical composition for inhibiting apoptosis of neuron or neurodegeneration |
| US9290464B2 (en) | 2010-05-03 | 2016-03-22 | Sk Biopharmaceuticals Co., Ltd. | Pharmaceutical composition for inhibiting apoptosis of neuron or neurodegeneration |
Also Published As
| Publication number | Publication date |
|---|---|
| CY1117379T1 (el) | 2017-04-26 |
| HUE026577T2 (hu) | 2016-06-28 |
| WO2007045339A1 (de) | 2007-04-26 |
| SI1937673T1 (sl) | 2016-02-29 |
| EP1937673B1 (de) | 2015-10-21 |
| US8044208B2 (en) | 2011-10-25 |
| DK1937673T3 (en) | 2016-01-25 |
| ES2558874T3 (es) | 2016-02-09 |
| JP2009511516A (ja) | 2009-03-19 |
| EP1937673A1 (de) | 2008-07-02 |
| PL1937673T3 (pl) | 2016-03-31 |
| JP5266053B2 (ja) | 2013-08-21 |
| PT1937673E (pt) | 2016-02-08 |
| US20080262028A1 (en) | 2008-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal | ||
| 8165 | Publication of following application cancelled | ||
| 8181 | Inventor (new situation) |
Inventor name: HEITSCH, HOLGER, DR., 65929 FRANKFURT, DE Inventor name: WEHNER, VOLKMAR, DR., 65929 FRANKFURT, DE Inventor name: KALLUS, CHRISTOPHER, DR., 65929 FRANKFURT, DE |