HRP20090360T1 - Derivati n-hidroksiamida i njihova upotreba - Google Patents
Derivati n-hidroksiamida i njihova upotreba Download PDFInfo
- Publication number
- HRP20090360T1 HRP20090360T1 HR20090360T HRP20090360T HRP20090360T1 HR P20090360 T1 HRP20090360 T1 HR P20090360T1 HR 20090360 T HR20090360 T HR 20090360T HR P20090360 T HRP20090360 T HR P20090360T HR P20090360 T1 HRP20090360 T1 HR P20090360T1
- Authority
- HR
- Croatia
- Prior art keywords
- carbonyl
- methyl
- methylpiperazin
- piperazin
- dihydroxy
- Prior art date
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims abstract 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 17
- 125000003118 aryl group Chemical group 0.000 claims abstract 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 15
- -1 4-pyridin-2-ylpiperazin-1-yl Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 206010016654 Fibrosis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000004761 fibrosis Effects 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- ULBJVNGTZVUWBI-COXVUDFISA-N (2s,3s)-3-[(2r)-4-(3-chlorophenyl)-2-methylpiperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=CC(Cl)=C1 ULBJVNGTZVUWBI-COXVUDFISA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- IJVKWNVXKJNXAO-DLBZAZTESA-N (2r,3s)-2-hydroxy-3-[4-(4-methoxyphenyl)piperazine-1-carbonyl]-5-methylhexanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)[C@@H](CC(C)C)[C@@H](O)C(O)=O)CC1 IJVKWNVXKJNXAO-DLBZAZTESA-N 0.000 claims 1
- JFZCXFVDXXSQBP-GXFFZTMASA-N (2r,3s)-2-hydroxy-3-methyl-4-oxo-4-[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)C)CCN1C1=CC=C(OC(F)(F)F)C=C1 JFZCXFVDXXSQBP-GXFFZTMASA-N 0.000 claims 1
- VSXDTGKRPJYHAG-DLBZAZTESA-N (2r,3s)-2-hydroxy-5-methyl-3-(4-phenyl-3,6-dihydro-2h-pyridine-1-carbonyl)hexanoic acid Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCC(C=2C=CC=CC=2)=C1 VSXDTGKRPJYHAG-DLBZAZTESA-N 0.000 claims 1
- ZNLMMSINSZUAAI-DZGCQCFKSA-N (2r,3s)-2-hydroxy-5-methyl-3-(4-pyridin-2-ylpiperazine-1-carbonyl)hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=CC=N1 ZNLMMSINSZUAAI-DZGCQCFKSA-N 0.000 claims 1
- GFWXEYFFOXCYSV-QWHCGFSZSA-N (2r,3s)-2-hydroxy-5-methyl-3-(4-pyrimidin-2-ylpiperazine-1-carbonyl)hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=NC=CC=N1 GFWXEYFFOXCYSV-QWHCGFSZSA-N 0.000 claims 1
- WMCTYKQRLUTLPF-JKSUJKDBSA-N (2r,3s)-2-hydroxy-5-methyl-3-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=NOC(C=2C=CC=CC=2)=N1 WMCTYKQRLUTLPF-JKSUJKDBSA-N 0.000 claims 1
- AKFVJNZRPPPUHA-LSDHHAIUSA-N (2r,3s)-2-hydroxy-5-methyl-3-[4-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=NOC(C=2C=CN=CC=2)=N1 AKFVJNZRPPPUHA-LSDHHAIUSA-N 0.000 claims 1
- CGIZUCMKYYEOPX-GXTWGEPZSA-N (2r,3s)-2-hydroxy-5-methyl-3-[4-(5-thiophen-2-yl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=NOC(C=2SC=CC=2)=N1 CGIZUCMKYYEOPX-GXTWGEPZSA-N 0.000 claims 1
- DBPDKQAUOILJNF-JKSUJKDBSA-N (2r,3s)-2-hydroxy-5-methyl-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]hexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(C(F)(F)F)C=C1 DBPDKQAUOILJNF-JKSUJKDBSA-N 0.000 claims 1
- IXSOMRRAFSTBDN-LUKYLMHMSA-N (2r,3s)-3-[(1s,4s)-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@H](CC(C)C)[C@@H](O)C(=O)NO)[H])N2C1=CC=C(F)C=C1 IXSOMRRAFSTBDN-LUKYLMHMSA-N 0.000 claims 1
- MYKJUZSYKWWTNH-IVMMDQJWSA-N (2r,3s)-3-[(2r)-4-(5-chloropyridin-2-yl)-2-methylpiperazine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(Cl)C=N1 MYKJUZSYKWWTNH-IVMMDQJWSA-N 0.000 claims 1
- XKDZQWIGQUPITR-IVMMDQJWSA-N (2r,3s)-3-[(2r)-4-(5-chloropyridin-2-yl)-2-methylpiperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=C(Cl)C=N1 XKDZQWIGQUPITR-IVMMDQJWSA-N 0.000 claims 1
- NGLHNIQZOBNLPF-XJKSGUPXSA-N (2r,3s)-3-[4-(2-fluorophenyl)piperazine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=CC=C1F NGLHNIQZOBNLPF-XJKSGUPXSA-N 0.000 claims 1
- RNLFRPDVHDPRMF-XJKSGUPXSA-N (2r,3s)-3-[4-(2-fluorophenyl)piperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=CC=C1F RNLFRPDVHDPRMF-XJKSGUPXSA-N 0.000 claims 1
- AXKRJWMSSNSPBL-DLBZAZTESA-N (2r,3s)-3-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCC(C=2C=CC(Cl)=CC=2)=C1 AXKRJWMSSNSPBL-DLBZAZTESA-N 0.000 claims 1
- BTBNKVHAODOHII-DLBZAZTESA-N (2r,3s)-3-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCC(C=2C=CC(Cl)=CC=2)=C1 BTBNKVHAODOHII-DLBZAZTESA-N 0.000 claims 1
- BVVCTYGQEXLXDF-DLBZAZTESA-N (2r,3s)-3-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCC(C=2C=CC(F)=CC=2)=C1 BVVCTYGQEXLXDF-DLBZAZTESA-N 0.000 claims 1
- HJVAAOHIYJNGCN-DLBZAZTESA-N (2r,3s)-3-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCC(C=2C=CC(F)=CC=2)=C1 HJVAAOHIYJNGCN-DLBZAZTESA-N 0.000 claims 1
- YSBVKFPWGCLACH-JKSUJKDBSA-N (2r,3s)-3-[4-(4-fluorophenyl)piperazine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(F)C=C1 YSBVKFPWGCLACH-JKSUJKDBSA-N 0.000 claims 1
- QORMEULMZBGBNQ-JKSUJKDBSA-N (2r,3s)-3-[4-(4-fluorophenyl)piperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=C(F)C=C1 QORMEULMZBGBNQ-JKSUJKDBSA-N 0.000 claims 1
- KPMGZALZQOVQOY-DZGCQCFKSA-N (2r,3s)-3-[4-(5-bromopyridin-2-yl)piperazine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(Br)C=N1 KPMGZALZQOVQOY-DZGCQCFKSA-N 0.000 claims 1
- COFYIHLUCKOOOA-DZGCQCFKSA-N (2r,3s)-3-[4-(5-bromopyridin-2-yl)piperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=C(Br)C=N1 COFYIHLUCKOOOA-DZGCQCFKSA-N 0.000 claims 1
- FBSDXTKJAOTYBS-DZGCQCFKSA-N (2r,3s)-3-[4-(5-chloropyridin-2-yl)piperazine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(Cl)C=N1 FBSDXTKJAOTYBS-DZGCQCFKSA-N 0.000 claims 1
- XJFFZFLODKTTOM-DZGCQCFKSA-N (2r,3s)-3-[4-(5-chloropyridin-2-yl)piperazine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=C(Cl)C=N1 XJFFZFLODKTTOM-DZGCQCFKSA-N 0.000 claims 1
- AJLLJKGXRHVCOT-DLBZAZTESA-N (2r,3s)-3-[4-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carbonyl]-2-hydroxy-5-methylhexanoic acid Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(O)=O)CC(C)C)CCC1C1=NN=C(C=2C=CC(F)=CC=2)O1 AJLLJKGXRHVCOT-DLBZAZTESA-N 0.000 claims 1
- OZUHUHKNSHCQRX-DLBZAZTESA-N (2r,3s)-3-[4-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carbonyl]-n,2-dihydroxy-5-methylhexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCC1C1=NN=C(C=2C=CC(F)=CC=2)O1 OZUHUHKNSHCQRX-DLBZAZTESA-N 0.000 claims 1
- SPGFGZHNGBLBET-RBUKOAKNSA-N (2r,3s)-3-benzyl-2-hydroxy-4-oxo-4-[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]butanoic acid Chemical compound C([C@@H]([C@@H](O)C(O)=O)C(=O)N1CCN(CC1)C=1C=CC(OC(F)(F)F)=CC=1)C1=CC=CC=C1 SPGFGZHNGBLBET-RBUKOAKNSA-N 0.000 claims 1
- ZLVIDIPOUZHNMV-RBUKOAKNSA-N (2r,3s)-3-benzyl-n,2-dihydroxy-4-oxo-4-[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]butanamide Chemical compound C([C@@H]([C@@H](O)C(=O)NO)C(=O)N1CCN(CC1)C=1C=CC(OC(F)(F)F)=CC=1)C1=CC=CC=C1 ZLVIDIPOUZHNMV-RBUKOAKNSA-N 0.000 claims 1
- OFHDMPBTOCFQHK-GXFFZTMASA-N (2r,3s)-n,2-dihydroxy-3-methyl-4-oxo-4-[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]butanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)C)CCN1C1=CC=C(OC(F)(F)F)C=C1 OFHDMPBTOCFQHK-GXFFZTMASA-N 0.000 claims 1
- ORQUXFASHNIOLB-DLBZAZTESA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-(4-phenyl-3,6-dihydro-2h-pyridine-1-carbonyl)hexanamide Chemical compound C1N(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCC(C=2C=CC=CC=2)=C1 ORQUXFASHNIOLB-DLBZAZTESA-N 0.000 claims 1
- RDSZMKNROGVWNY-QWHCGFSZSA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-(4-pyrimidin-2-ylpiperazine-1-carbonyl)hexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=NC=CC=N1 RDSZMKNROGVWNY-QWHCGFSZSA-N 0.000 claims 1
- GSFQMVBMHQNULH-JKSUJKDBSA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=NOC(C=2C=CC=CC=2)=N1 GSFQMVBMHQNULH-JKSUJKDBSA-N 0.000 claims 1
- OPEXYJWLLGSYBM-LSDHHAIUSA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-[4-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=NOC(C=2C=CN=CC=2)=N1 OPEXYJWLLGSYBM-LSDHHAIUSA-N 0.000 claims 1
- FTEAQKPWIAGRJR-GXTWGEPZSA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-[4-(5-thiophen-2-yl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]hexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=NOC(C=2SC=CC=2)=N1 FTEAQKPWIAGRJR-GXTWGEPZSA-N 0.000 claims 1
- JICNEXNENQTHIO-JKSUJKDBSA-N (2r,3s)-n,2-dihydroxy-5-methyl-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]hexanamide Chemical compound C1CN(C(=O)[C@H]([C@@H](O)C(=O)NO)CC(C)C)CCN1C1=CC=C(C(F)(F)F)C=C1 JICNEXNENQTHIO-JKSUJKDBSA-N 0.000 claims 1
- LXHMBELHJWWAOY-JENJKZFGSA-N (2s)-2-hydroxy-3-methyl-4-[(2r)-2-methyl-4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]-4-oxobutanoic acid Chemical compound C1[C@@H](C)N(C(=O)C([C@H](O)C(O)=O)C)CCN1C1=CC=C(OC(F)(F)F)C=C1 LXHMBELHJWWAOY-JENJKZFGSA-N 0.000 claims 1
- COFJWLJZCMGUFR-JENJKZFGSA-N (2s)-n,2-dihydroxy-3-methyl-4-[(2r)-2-methyl-4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]-4-oxobutanamide Chemical compound C1[C@@H](C)N(C(=O)C([C@H](O)C(=O)NO)C)CCN1C1=CC=C(OC(F)(F)F)C=C1 COFJWLJZCMGUFR-JENJKZFGSA-N 0.000 claims 1
- BVNICMZKNDSVDH-JLSDUUJJSA-N (2s,3s)-2-hydroxy-3-[(2r)-4-(3-methoxyphenyl)-2-methylpiperazine-1-carbonyl]-5-methylhexanoic acid Chemical compound COC1=CC=CC(N2C[C@@H](C)N(CC2)C(=O)[C@@H](CC(C)C)[C@H](O)C(O)=O)=C1 BVNICMZKNDSVDH-JLSDUUJJSA-N 0.000 claims 1
- ZFKPBRSSOJWQNA-JLSDUUJJSA-N (2s,3s)-2-hydroxy-3-[(2r)-4-(4-methoxyphenyl)-2-methylpiperazine-1-carbonyl]-5-methylhexanoic acid Chemical compound C1=CC(OC)=CC=C1N1C[C@@H](C)N(C(=O)[C@@H](CC(C)C)[C@H](O)C(O)=O)CC1 ZFKPBRSSOJWQNA-JLSDUUJJSA-N 0.000 claims 1
- JOPLGPIHYYHEPW-XGRCMKMKSA-N (2s,3s)-2-hydroxy-3-[(2r)-4-(6-methoxynaphthalen-2-yl)-2-methylpiperazine-1-carbonyl]-5-methylhexanoic acid Chemical compound C1=CC2=CC(OC)=CC=C2C=C1N1CCN(C(=O)[C@@H](CC(C)C)[C@H](O)C(O)=O)[C@H](C)C1 JOPLGPIHYYHEPW-XGRCMKMKSA-N 0.000 claims 1
- VFQLRAIQGUNNLE-NJAFHUGGSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(4-methylphenyl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(C)C=C1 VFQLRAIQGUNNLE-NJAFHUGGSA-N 0.000 claims 1
- NJNQYXQEFLICIY-JLSDUUJJSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(S(C)(=O)=O)C=C1 NJNQYXQEFLICIY-JLSDUUJJSA-N 0.000 claims 1
- UCVZKXUWWLRLHN-LEOXJPRUSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(4-phenylphenyl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(C=2C=CC=CC=2)C=C1 UCVZKXUWWLRLHN-LEOXJPRUSA-N 0.000 claims 1
- ODWSIZZWUYQBKH-UXPWSPDFSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(4-propoxyphenyl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1=CC(OCCC)=CC=C1N1C[C@@H](C)N(C(=O)[C@@H](CC(C)C)[C@H](O)C(O)=O)CC1 ODWSIZZWUYQBKH-UXPWSPDFSA-N 0.000 claims 1
- RUEXRESLKVAQLP-UXPWSPDFSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(4-propylphenyl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1=CC(CCC)=CC=C1N1C[C@@H](C)N(C(=O)[C@@H](CC(C)C)[C@H](O)C(O)=O)CC1 RUEXRESLKVAQLP-UXPWSPDFSA-N 0.000 claims 1
- NZBFFUUWFWCXOH-AGHHOFFYSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-(5-phenylpyridin-2-yl)piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(C=2C=CC=CC=2)C=N1 NZBFFUUWFWCXOH-AGHHOFFYSA-N 0.000 claims 1
- MVRIMNLQYYHESW-COXVUDFISA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-[4-(trifluoromethoxy)phenyl]piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(OC(F)(F)F)C=C1 MVRIMNLQYYHESW-COXVUDFISA-N 0.000 claims 1
- OTNUTZMJSIHNBO-COXVUDFISA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC=C(C(F)(F)F)C=C1 OTNUTZMJSIHNBO-COXVUDFISA-N 0.000 claims 1
- PRKIMBFHIHDSBC-INWMFGNUSA-N (2s,3s)-2-hydroxy-5-methyl-3-[(2r)-2-methyl-4-[4-(trifluoromethyl)pyridin-2-yl]piperazine-1-carbonyl]hexanoic acid Chemical compound C1[C@@H](C)N(C(=O)[C@H]([C@H](O)C(O)=O)CC(C)C)CCN1C1=CC(C(F)(F)F)=CC=N1 PRKIMBFHIHDSBC-INWMFGNUSA-N 0.000 claims 1
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Classifications
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/20—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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PL1660471T3 (pl) * | 2003-08-23 | 2011-10-31 | Vernalis R&D Ltd | Pochodne kwasu hydroksamowego jako inhibitory metaloproteinaz |
JP4950070B2 (ja) * | 2005-01-31 | 2012-06-13 | メルク セローノ ソシエテ アノニム | N−ヒドロキシアミド誘導体及びその使用 |
CN101573333B (zh) | 2006-10-28 | 2013-06-12 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
WO2008079945A2 (en) * | 2006-12-20 | 2008-07-03 | University Of South Florida | Rock inhibitors and uses thereof |
JO2959B1 (en) * | 2007-05-14 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Mono-hydrochloric salts for histone dacetylase inhibitor |
WO2017041228A1 (zh) * | 2015-09-08 | 2017-03-16 | 浙江九洲药业股份有限公司 | 六氢呋喃并呋喃醇衍生物的制备方法、其中间体及其制备方法 |
WO2018081167A1 (en) * | 2016-10-24 | 2018-05-03 | Yumanity Therapeutics | Compounds and uses thereof |
WO2019018795A1 (en) * | 2017-07-20 | 2019-01-24 | Yumanity Therapeutics | COMPOUNDS AND USES THEREOF |
CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
EP3492454A1 (en) * | 2017-11-30 | 2019-06-05 | Step Pharma S.A.S. | Compounds |
US11655246B2 (en) | 2017-11-30 | 2023-05-23 | Step Pharma S.A.S. | Aminothiazole compounds as inhibitors of CTPS1 |
EP3717465A1 (en) | 2017-11-30 | 2020-10-07 | Step Pharma S.A.S. | Compounds |
MA52365A (fr) | 2018-04-25 | 2021-03-03 | Yumanity Therapeutics Inc | Composés et leurs utilisations |
WO2019241131A1 (en) | 2018-06-11 | 2019-12-19 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine m1 receptor antagonists |
EP3870574B1 (en) | 2018-10-23 | 2023-01-04 | Step Pharma S.A.S. | Aminopyrimidine/pyrazine derivatives as ctps1 inhibitors |
CN114729044A (zh) * | 2019-10-07 | 2022-07-08 | 帕珀莱恩医疗公司 | 毒蕈碱型乙酰胆碱m1受体拮抗剂 |
US11752149B2 (en) | 2019-12-02 | 2023-09-12 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
CN115780487B (zh) * | 2023-01-05 | 2023-05-05 | 河北东丽新材料有限公司 | 一种萃取剂及利用其处理4,4`-联苯醚二酐生产固废的方法 |
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WO1995029892A1 (en) * | 1994-04-28 | 1995-11-09 | The Du Pont Merck Pharmaceutical Company | Hydroxamic acid and amino acid derivatives and their use as anti-arthritic agents |
GB9411598D0 (en) * | 1994-06-09 | 1994-08-03 | Hoffmann La Roche | Hydroxamic acid derivatives |
GB9702088D0 (en) | 1997-01-31 | 1997-03-19 | Pharmacia & Upjohn Spa | Matrix metalloproteinase inhibitors |
US6797820B2 (en) | 1999-12-17 | 2004-09-28 | Vicuron Pharmaceuticals Inc. | Succinate compounds, compositions and methods of use and preparation |
WO2001083461A1 (fr) | 2000-04-28 | 2001-11-08 | Shionogi & Co., Ltd. | Derives de thiazole et d'oxazole |
GB0208176D0 (en) * | 2002-04-09 | 2002-05-22 | Novartis Ag | Organic compounds |
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- 2005-07-25 AU AU2005266313A patent/AU2005266313B2/en not_active Ceased
- 2005-07-25 ES ES05772035T patent/ES2325836T3/es active Active
- 2005-07-25 US US11/572,761 patent/US8008302B2/en not_active Expired - Fee Related
- 2005-07-25 PL PL05772035T patent/PL1771421T3/pl unknown
- 2005-07-25 EP EP05772035A patent/EP1771421B1/en active Active
- 2005-07-25 KR KR1020077004004A patent/KR20070046873A/ko active IP Right Grant
- 2005-07-25 EA EA200700037A patent/EA012584B1/ru not_active IP Right Cessation
- 2005-07-25 RS RSP-2009/0316A patent/RS50980B/sr unknown
- 2005-07-25 CA CA2570903A patent/CA2570903C/en not_active Expired - Fee Related
- 2005-07-25 PT PT05772035T patent/PT1771421E/pt unknown
- 2005-07-25 CN CN2005800250862A patent/CN1989106B/zh not_active Expired - Fee Related
- 2005-07-25 MX MX2007001022A patent/MX2007001022A/es active IP Right Grant
- 2005-07-25 JP JP2007523074A patent/JP5226307B2/ja not_active Expired - Fee Related
- 2005-07-25 AT AT05772035T patent/ATE430133T1/de active
- 2005-07-25 WO PCT/EP2005/053616 patent/WO2006010751A1/en active Application Filing
- 2005-07-25 DE DE602005014236T patent/DE602005014236D1/de active Active
- 2005-07-25 SI SI200530725T patent/SI1771421T1/sl unknown
- 2005-07-25 DK DK05772035T patent/DK1771421T3/da active
- 2005-07-26 AR ARP050103093A patent/AR050435A1/es not_active Application Discontinuation
-
2007
- 2007-01-11 IL IL180682A patent/IL180682A/en not_active IP Right Cessation
- 2007-02-21 NO NO20070994A patent/NO20070994L/no not_active Application Discontinuation
-
2009
- 2009-06-23 HR HR20090360T patent/HRP20090360T1/hr unknown
- 2009-06-30 CY CY20091100695T patent/CY1109194T1/el unknown
-
2011
- 2011-06-08 US US13/155,411 patent/US8247437B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
AR050435A1 (es) | 2006-10-25 |
US8247437B2 (en) | 2012-08-21 |
AU2005266313A1 (en) | 2006-02-02 |
US20080021028A1 (en) | 2008-01-24 |
US20110263628A1 (en) | 2011-10-27 |
RS50980B (sr) | 2010-10-31 |
ATE430133T1 (de) | 2009-05-15 |
PL1771421T3 (pl) | 2009-08-31 |
BRPI0513878A (pt) | 2008-05-20 |
JP5226307B2 (ja) | 2013-07-03 |
NO20070994L (no) | 2007-04-26 |
JP2008507575A (ja) | 2008-03-13 |
EA200700037A1 (ru) | 2007-08-31 |
ES2325836T3 (es) | 2009-09-21 |
PT1771421E (pt) | 2009-05-25 |
US8008302B2 (en) | 2011-08-30 |
EA012584B1 (ru) | 2009-10-30 |
AU2005266313B2 (en) | 2011-08-25 |
CA2570903C (en) | 2013-09-17 |
KR20070046873A (ko) | 2007-05-03 |
CA2570903A1 (en) | 2006-02-02 |
SI1771421T1 (sl) | 2009-10-31 |
WO2006010751A1 (en) | 2006-02-02 |
CN1989106B (zh) | 2013-12-04 |
CY1109194T1 (el) | 2014-07-02 |
IL180682A0 (en) | 2007-06-03 |
EP1771421A1 (en) | 2007-04-11 |
EP1771421B1 (en) | 2009-04-29 |
DE602005014236D1 (de) | 2009-06-10 |
CN1989106A (zh) | 2007-06-27 |
MX2007001022A (es) | 2007-04-12 |
IL180682A (en) | 2011-11-30 |
DK1771421T3 (da) | 2009-07-13 |
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