JP2009511516A5 - - Google Patents
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- Publication number
- JP2009511516A5 JP2009511516A5 JP2008534894A JP2008534894A JP2009511516A5 JP 2009511516 A5 JP2009511516 A5 JP 2009511516A5 JP 2008534894 A JP2008534894 A JP 2008534894A JP 2008534894 A JP2008534894 A JP 2008534894A JP 2009511516 A5 JP2009511516 A5 JP 2009511516A5
- Authority
- JP
- Japan
- Prior art keywords
- ylmethyl
- aminopyridin
- alkylene
- propionic acid
- imidazol
- 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.)
- Granted
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- -1 benzoimidazolinyl Chemical group 0.000 claims 41
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 125000002971 oxazolyl group Chemical group 0.000 claims 7
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 6
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 6
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 6
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 5
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 5
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- BYJWOQJVWRUSFB-UHFFFAOYSA-N 3-(4-aminocyclohexyl)-2-[1-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1CC(N)CCC1CC(C(O)=O)C(N=C1)=CN1CC1=NN=C(C2CC2)S1 BYJWOQJVWRUSFB-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000005438 isoindazolyl group Chemical group 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- HKPURFXCABALOT-CYBMUJFWSA-N (2r)-3-(6-aminopyridin-3-yl)-2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1C[C@@H](C(O)=O)C(N=C1)=CN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HKPURFXCABALOT-CYBMUJFWSA-N 0.000 claims 1
- HKPURFXCABALOT-ZDUSSCGKSA-N (2s)-3-(6-aminopyridin-3-yl)-2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1C[C@H](C(O)=O)C(N=C1)=CN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HKPURFXCABALOT-ZDUSSCGKSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- GPDUGVOFBWFPJM-UHFFFAOYSA-N 3-(6-amino-5-methylpyridin-3-yl)-2-[1-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound N1=C(N)C(C)=CC(CC(C(O)=O)C=2N=CN(CC=3SC(=NN=3)C3CC3)C=2)=C1 GPDUGVOFBWFPJM-UHFFFAOYSA-N 0.000 claims 1
- HUFICPNMQKBWFK-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(4-bromothiophen-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC(Br)=CS1 HUFICPNMQKBWFK-UHFFFAOYSA-N 0.000 claims 1
- WUFULKRXLAAIOW-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclobutyl-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(C2CCC2)=C1 WUFULKRXLAAIOW-UHFFFAOYSA-N 0.000 claims 1
- JUCDKZGTEYNOQG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclobutyl-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(C2CCC2)S1 JUCDKZGTEYNOQG-UHFFFAOYSA-N 0.000 claims 1
- LJOQOHFLKRBWLX-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclohexyl-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(C2CCCCC2)=C1 LJOQOHFLKRBWLX-UHFFFAOYSA-N 0.000 claims 1
- WGPAYPGNQWEVGZ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclohexyl-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(C2CCCCC2)S1 WGPAYPGNQWEVGZ-UHFFFAOYSA-N 0.000 claims 1
- JRZVWHJISNBLPC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclopentyl-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(C2CCCC2)S1 JRZVWHJISNBLPC-UHFFFAOYSA-N 0.000 claims 1
- ROGQHVIEDHZKCC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-cyclopropyl-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(C2CC2)=C1 ROGQHVIEDHZKCC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DSTAIOCBKUINOO-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-methyl-1,2-oxazol-3-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound O1C(C)=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=N1 DSTAIOCBKUINOO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ICRUBEPJCVPMNL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-phenyl-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=CC=CC=2)=C1 ICRUBEPJCVPMNL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- MYVMXNFSPZGCOB-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(6-chlorothieno[2,3-b]pyridin-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC2=CC=C(Cl)N=C2S1 MYVMXNFSPZGCOB-UHFFFAOYSA-N 0.000 claims 1
- DYKKMTWSDXRXGT-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]ethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CCC1=NOC(C=2SC(Cl)=CC=2)=C1 DYKKMTWSDXRXGT-UHFFFAOYSA-N 0.000 claims 1
- YHJNZSKQHOMKIL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-5-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CN=C(C=2SC(Cl)=CC=2)S1 YHJNZSKQHOMKIL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AKUMJFBHNQSTIM-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-[4-[(4-chlorophenyl)methoxy]phenyl]-1,2,4-oxadiazol-5-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=NC(C=2C=CC(OCC=3C=CC(Cl)=CC=3)=CC=2)=NO1 AKUMJFBHNQSTIM-UHFFFAOYSA-N 0.000 claims 1
- ICBMGIUWMBBJRF-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC(C=2C=CC=CC=2)=C(C(F)(F)F)S1 ICBMGIUWMBBJRF-UHFFFAOYSA-N 0.000 claims 1
- WPFJLHZJMTWIBH-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(2,3-dihydro-1,4-benzodioxin-6-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=2C=C3OCCOC3=CC=2)=C1 WPFJLHZJMTWIBH-UHFFFAOYSA-N 0.000 claims 1
- UVBCJMPJTVONRR-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(2,3-dihydro-1h-inden-5-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=2C=C3CCCC3=CC=2)=C1 UVBCJMPJTVONRR-UHFFFAOYSA-N 0.000 claims 1
- FALBXQNLRHETDZ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(2-chlorophenyl)-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(=CC=CC=2)Cl)=C1 FALBXQNLRHETDZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- AJHZUDWPXOSAML-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1,2,4-oxadiazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound CC1=NOC(C)=C1C1=NC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 AJHZUDWPXOSAML-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BUFFRJSTCDQUNK-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-benzylphenyl)-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=CC(CC=3C=CC=CC=3)=CC=2)=C1 BUFFRJSTCDQUNK-UHFFFAOYSA-N 0.000 claims 1
- BLFNAQGIRJIUTL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-butan-2-ylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(C)CC)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 BLFNAQGIRJIUTL-UHFFFAOYSA-N 0.000 claims 1
- PNSLFOKYEVQVMK-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-butylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 PNSLFOKYEVQVMK-UHFFFAOYSA-N 0.000 claims 1
- ZKGJPEMZDXKWFR-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-cyclohexylphenyl)-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=CC(=CC=2)C2CCCCC2)=C1 ZKGJPEMZDXKWFR-UHFFFAOYSA-N 0.000 claims 1
- QJCNZXFWTRTHFG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-cyclopentylphenyl)-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=CC(=CC=2)C2CCCC2)=C1 QJCNZXFWTRTHFG-UHFFFAOYSA-N 0.000 claims 1
- ZHTNBODNAJHAKP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-fluorophenyl)-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=CC(F)=CC=2)=C1 ZHTNBODNAJHAKP-UHFFFAOYSA-N 0.000 claims 1
- AHHNSQCMCDOMKL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-methoxyphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 AHHNSQCMCDOMKL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QWZUQMONGXLTQV-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-methylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 QWZUQMONGXLTQV-UHFFFAOYSA-N 0.000 claims 1
- ROQSFKPHGVMRIX-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-propan-2-ylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 ROQSFKPHGVMRIX-UHFFFAOYSA-N 0.000 claims 1
- LYKUWXWTDOODSN-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-propylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 LYKUWXWTDOODSN-UHFFFAOYSA-N 0.000 claims 1
- XTZFIZIBNICGRE-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-tert-butyl-2,6-dimethylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 XTZFIZIBNICGRE-UHFFFAOYSA-N 0.000 claims 1
- LXVHQXHBJWZWOP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(4-tert-butylphenyl)-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 LXVHQXHBJWZWOP-UHFFFAOYSA-N 0.000 claims 1
- GCJYYHXIVLCDLD-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(5,6,7,8-tetrahydronaphthalen-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=2C=C3CCCCC3=CC=2)=C1 GCJYYHXIVLCDLD-UHFFFAOYSA-N 0.000 claims 1
- HKPURFXCABALOT-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-(5-chlorothiophen-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(Cl)=CC=2)=C1 HKPURFXCABALOT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- LCBXXWMEIJJAOI-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-[4-(2-methylpropyl)phenyl]-1,2-oxazol-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=NO1 LCBXXWMEIJJAOI-UHFFFAOYSA-N 0.000 claims 1
- RIUBBCPPYHLKKY-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[5-[4-(2-phenylethyl)phenyl]-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=CC(CCC=3C=CC=CC=3)=CC=2)=C1 RIUBBCPPYHLKKY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JXCVCCWUISUJCZ-UHFFFAOYSA-N 6-amino-2-[1-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]imidazol-4-yl]hexanoic acid Chemical compound C1=NC(C(C(O)=O)CCCCN)=CN1CC1=NN=C(C2CC2)S1 JXCVCCWUISUJCZ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 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 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004623 carbolinyl group Chemical group 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004932 phenoxathinyl group Chemical group 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005049385.8 | 2005-10-15 | ||
| DE102005049385A DE102005049385A1 (de) | 2005-10-15 | 2005-10-15 | Imidazolderivate als Inhibitoren von TAFIa |
| PCT/EP2006/009500 WO2007045339A1 (de) | 2005-10-15 | 2006-09-30 | Imidazolderivate als inhibitoren von tafi-a |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009511516A JP2009511516A (ja) | 2009-03-19 |
| JP2009511516A5 true JP2009511516A5 (https=) | 2009-11-19 |
| JP5266053B2 JP5266053B2 (ja) | 2013-08-21 |
Family
ID=37733974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008534894A Expired - Fee Related 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 |
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=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009103432A2 (en) * | 2008-02-21 | 2009-08-27 | Sanofi-Aventis | Covalently binding imaging probes |
| WO2010050525A1 (ja) | 2008-10-29 | 2010-05-06 | 大正製薬株式会社 | ＴＡＦＩａ阻害活性を有する化合物 |
| BR112012023412A2 (pt) | 2010-03-18 | 2018-05-08 | Daiichi Sankyo Company, Limited | composto, drogra farmacêutica, inibidor de tafia, promotor de fibrinólise, droga preventiva ou terapêutica, composição farmacêutica, e, uso de um composto. |
| EP2548871B1 (en) | 2010-03-18 | 2017-07-19 | Daiichi Sankyo Company, Limited | Cycloalkyl-substituted imidazole derivative |
| KR101799429B1 (ko) | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| KR20160018557A (ko) | 2013-06-10 | 2016-02-17 | 사노피 | TAFIa의 저해제로서의 마크로사이클릭 우레아 유도체, 이의 제법 및 의약품으로서의 이의 용도 |
| MX2022007376A (es) | 2019-12-20 | 2022-09-02 | Tenaya Therapeutics Inc | Fluoroalqull-oxadiazoles y sus usos. |
| US20240252502A1 (en) | 2021-05-04 | 2024-08-01 | Tenaya Therapeutics, Inc. | Hdac6 inhibitors for treatment of metabolic disease and hfpef |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE447557T1 (de) * | 2000-08-17 | 2009-11-15 | Pfizer Ltd | Substitutuierte imidazole als tafia inhibitoren |
| WO2003013526A1 (en) * | 2001-08-08 | 2003-02-20 | Merck & Co. Inc. | Anticoagulant compounds |
| BR0307033A (pt) * | 2002-01-22 | 2004-12-07 | Pfizer | ácidos 3-(imidazolil)-2-aminopropanóicos para o uso como inibidores tafi-a para o tratamento de doenças trombóticas |
-
2005
- 2005-10-15 DE DE102005049385A patent/DE102005049385A1/de not_active Withdrawn
-
2006
- 2006-09-30 PL PL06792327T patent/PL1937673T3/pl unknown
- 2006-09-30 SI SI200632014T patent/SI1937673T1/sl unknown
- 2006-09-30 HU HUE06792327A patent/HUE026577T2/hu unknown
- 2006-09-30 DK DK06792327.6T patent/DK1937673T3/en active
- 2006-09-30 JP JP2008534894A patent/JP5266053B2/ja not_active Expired - Fee Related
- 2006-09-30 EP EP06792327.6A patent/EP1937673B1/de not_active Not-in-force
- 2006-09-30 ES ES06792327.6T patent/ES2558874T3/es active Active
- 2006-09-30 WO PCT/EP2006/009500 patent/WO2007045339A1/de not_active Ceased
- 2006-09-30 PT PT67923276T patent/PT1937673E/pt unknown
-
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
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