JP2009540013A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009540013A5 JP2009540013A5 JP2009515622A JP2009515622A JP2009540013A5 JP 2009540013 A5 JP2009540013 A5 JP 2009540013A5 JP 2009515622 A JP2009515622 A JP 2009515622A JP 2009515622 A JP2009515622 A JP 2009515622A JP 2009540013 A5 JP2009540013 A5 JP 2009540013A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- diamine
- propyl
- phenyl
- biphenyl
- 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.)
- Pending
Links
- -1 N-methyl-pyrrolidin-2-yl Chemical group 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- XJVURRLJLAEWPY-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N XJVURRLJLAEWPY-UHFFFAOYSA-N 0.000 claims 2
- ZNMOJGFHGNCBDH-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N ZNMOJGFHGNCBDH-UHFFFAOYSA-N 0.000 claims 2
- OLIOEESQEYDHCN-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N)C OLIOEESQEYDHCN-UHFFFAOYSA-N 0.000 claims 2
- OJPSCZOGUPULIV-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N OJPSCZOGUPULIV-UHFFFAOYSA-N 0.000 claims 2
- DFZYQUNTJNOYKF-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N DFZYQUNTJNOYKF-UHFFFAOYSA-N 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- OLOADIMITYBCPD-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N OLOADIMITYBCPD-UHFFFAOYSA-N 0.000 claims 2
- KFLBAUIIAZZPRS-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N KFLBAUIIAZZPRS-UHFFFAOYSA-N 0.000 claims 2
- JQJPZMBCEBVIAF-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N)(F)F Chemical compound FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N)(F)F JQJPZMBCEBVIAF-UHFFFAOYSA-N 0.000 claims 2
- VATDLXQENWRMNZ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N VATDLXQENWRMNZ-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- ARUXVIHBRVIYHM-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1NCCC1)N ARUXVIHBRVIYHM-UHFFFAOYSA-N 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- HUSWKQVZIGTEGL-UHFFFAOYSA-N 1-[4-[3-[[2-(3-chloroanilino)pyrimidin-4-yl]amino]propyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCCNC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 HUSWKQVZIGTEGL-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- XEEXZIORUKKBII-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 XEEXZIORUKKBII-UHFFFAOYSA-N 0.000 claims 1
- PKVDVCMRWCLXKR-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-(piperidin-2-ylmethyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(NC=2N=C(NCC3NCCCC3)C=CN=2)=C1 PKVDVCMRWCLXKR-UHFFFAOYSA-N 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- SWOGFIPFTSZKFV-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-(2-pyridin-3-ylethyl)benzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NCCC1=CC=CN=C1 SWOGFIPFTSZKFV-UHFFFAOYSA-N 0.000 claims 1
- HSRLMIUTLYTNCA-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NCC1=CC=CN=C1 HSRLMIUTLYTNCA-UHFFFAOYSA-N 0.000 claims 1
- MXUDTTFTVAZJRN-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-phenylbenzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NC1=CC=CC=C1 MXUDTTFTVAZJRN-UHFFFAOYSA-N 0.000 claims 1
- DSYWRSXCWXRZEB-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 DSYWRSXCWXRZEB-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- NNRRMDVRQYVILC-UHFFFAOYSA-N 4-(3-morpholin-4-ylpropyl)-2-N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrimidine-2,4-diamine Chemical compound N1(CCOCC1)CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)OC(C(F)F)(F)F)N NNRRMDVRQYVILC-UHFFFAOYSA-N 0.000 claims 1
- IZUKJEPBPHWTTC-UHFFFAOYSA-N 4-(3-morpholin-4-ylpropyl)-2-N-[3-(trifluoromethoxy)phenyl]-1H-pyrimidine-2,4-diamine Chemical compound N1(CCOCC1)CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)OC(F)(F)F)N IZUKJEPBPHWTTC-UHFFFAOYSA-N 0.000 claims 1
- FGFMJNBXUYBHFU-UHFFFAOYSA-N 4-(dimethylamino)-n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 FGFMJNBXUYBHFU-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- ZVQGLJCZBLTDAV-UHFFFAOYSA-N BrC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound BrC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N ZVQGLJCZBLTDAV-UHFFFAOYSA-N 0.000 claims 1
- ZYAXRQJSCOMLLV-UHFFFAOYSA-N C(C)(C)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound C(C)(C)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N ZYAXRQJSCOMLLV-UHFFFAOYSA-N 0.000 claims 1
- LZOVFYYEBIPXGI-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N)Cl Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N)Cl LZOVFYYEBIPXGI-UHFFFAOYSA-N 0.000 claims 1
- XRMOTYJNMUNGTF-UHFFFAOYSA-N C1(=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N)C1=CC=CC=C1 Chemical compound C1(=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N)C1=CC=CC=C1 XRMOTYJNMUNGTF-UHFFFAOYSA-N 0.000 claims 1
- KBOJTKRTWOTNAF-UHFFFAOYSA-N CC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound CC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N KBOJTKRTWOTNAF-UHFFFAOYSA-N 0.000 claims 1
- UDTHCIUTAXVOLN-UHFFFAOYSA-N CC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound CC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N UDTHCIUTAXVOLN-UHFFFAOYSA-N 0.000 claims 1
- RDIODROHMLYAOF-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N RDIODROHMLYAOF-UHFFFAOYSA-N 0.000 claims 1
- BPINCGNLXDOUSA-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N BPINCGNLXDOUSA-UHFFFAOYSA-N 0.000 claims 1
- HNSKHLKERBEJLL-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N HNSKHLKERBEJLL-UHFFFAOYSA-N 0.000 claims 1
- LILFAJSQEBOFTH-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N LILFAJSQEBOFTH-UHFFFAOYSA-N 0.000 claims 1
- NSGATBDKPMVHOS-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N NSGATBDKPMVHOS-UHFFFAOYSA-N 0.000 claims 1
- KADUOGHDRMRGRE-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N KADUOGHDRMRGRE-UHFFFAOYSA-N 0.000 claims 1
- QMOKPWXIKDBANZ-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N QMOKPWXIKDBANZ-UHFFFAOYSA-N 0.000 claims 1
- FFKDBMVEVYAJGY-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N FFKDBMVEVYAJGY-UHFFFAOYSA-N 0.000 claims 1
- WVJMNQWAUSWUMN-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N WVJMNQWAUSWUMN-UHFFFAOYSA-N 0.000 claims 1
- ODVLJNCFMXOQGD-UHFFFAOYSA-N CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound CC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N ODVLJNCFMXOQGD-UHFFFAOYSA-N 0.000 claims 1
- FMEDHUOHDOOANO-UHFFFAOYSA-N CN(C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N)C Chemical compound CN(C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N)C FMEDHUOHDOOANO-UHFFFAOYSA-N 0.000 claims 1
- PYATVZGDUWYEMR-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N)C PYATVZGDUWYEMR-UHFFFAOYSA-N 0.000 claims 1
- LQHBLBNEAOVZLB-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N)C LQHBLBNEAOVZLB-UHFFFAOYSA-N 0.000 claims 1
- OWRZNFIOLXTREQ-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N)C OWRZNFIOLXTREQ-UHFFFAOYSA-N 0.000 claims 1
- FGVLTBYTGJWSEP-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N)C FGVLTBYTGJWSEP-UHFFFAOYSA-N 0.000 claims 1
- JVINEEHBTDPELC-UHFFFAOYSA-N CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N)C Chemical compound CN(C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N)C JVINEEHBTDPELC-UHFFFAOYSA-N 0.000 claims 1
- GLWYYXVEIONQCI-UHFFFAOYSA-N CN1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound CN1CCN(CC1)S(=O)(=O)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N GLWYYXVEIONQCI-UHFFFAOYSA-N 0.000 claims 1
- CKWFBIWVGLIZKO-UHFFFAOYSA-N COC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound COC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N CKWFBIWVGLIZKO-UHFFFAOYSA-N 0.000 claims 1
- BGTBPLWJRXEIGK-UHFFFAOYSA-N COC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound COC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N BGTBPLWJRXEIGK-UHFFFAOYSA-N 0.000 claims 1
- VXDVGEFVQYYNAI-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N VXDVGEFVQYYNAI-UHFFFAOYSA-N 0.000 claims 1
- XPNNFYMDCGMYKZ-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N XPNNFYMDCGMYKZ-UHFFFAOYSA-N 0.000 claims 1
- ZXFVRBBBQDAWTK-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N ZXFVRBBBQDAWTK-UHFFFAOYSA-N 0.000 claims 1
- MVCYKVYQLLMFOJ-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N MVCYKVYQLLMFOJ-UHFFFAOYSA-N 0.000 claims 1
- CIFHLORMJSWRBG-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound COC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N CIFHLORMJSWRBG-UHFFFAOYSA-N 0.000 claims 1
- ZSCMGHDLYJHVCT-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N ZSCMGHDLYJHVCT-UHFFFAOYSA-N 0.000 claims 1
- QJMMJXCPJLCDRK-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N QJMMJXCPJLCDRK-UHFFFAOYSA-N 0.000 claims 1
- MTFWTCBRVATAMV-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N MTFWTCBRVATAMV-UHFFFAOYSA-N 0.000 claims 1
- IYTSNHCRJRRVBK-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N IYTSNHCRJRRVBK-UHFFFAOYSA-N 0.000 claims 1
- ZRFWKEZGNLAWQZ-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N ZRFWKEZGNLAWQZ-UHFFFAOYSA-N 0.000 claims 1
- XYXFVIDHXIGNMH-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound COC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N XYXFVIDHXIGNMH-UHFFFAOYSA-N 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
- 208000006029 Cardiomegaly Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- KEINPEJUHUIJPR-UHFFFAOYSA-N ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCC1CN(CC1)C)N Chemical compound ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCC1CN(CC1)C)N KEINPEJUHUIJPR-UHFFFAOYSA-N 0.000 claims 1
- ALPDZWYURQRTCN-UHFFFAOYSA-N ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N ALPDZWYURQRTCN-UHFFFAOYSA-N 0.000 claims 1
- JTWMLZWSZAWSPL-UHFFFAOYSA-N ClC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound ClC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N JTWMLZWSZAWSPL-UHFFFAOYSA-N 0.000 claims 1
- JQVVYTJJVPHFCV-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NC1CC(NC(C1)(C)C)(C)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NC1CC(NC(C1)(C)C)(C)C)N JQVVYTJJVPHFCV-UHFFFAOYSA-N 0.000 claims 1
- NVEMIBHEORJTDD-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CCNCC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CCNCC1)N NVEMIBHEORJTDD-UHFFFAOYSA-N 0.000 claims 1
- VJGVDXMWPOJSIP-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CN(CCC1)C(C)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CN(CCC1)C(C)C)N VJGVDXMWPOJSIP-UHFFFAOYSA-N 0.000 claims 1
- VJLVEUUBJQCOQX-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CN(CCC1)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CN(CCC1)C)N VJLVEUUBJQCOQX-UHFFFAOYSA-N 0.000 claims 1
- AOGWDMHPKSLZJQ-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CNCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CNCCC1)N AOGWDMHPKSLZJQ-UHFFFAOYSA-N 0.000 claims 1
- BLFUOFCQDHYLHP-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CNCCO1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1CNCCO1)N BLFUOFCQDHYLHP-UHFFFAOYSA-N 0.000 claims 1
- GYNYTBIDOMBHAH-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1N(CCCC1)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCC1N(CCCC1)C)N GYNYTBIDOMBHAH-UHFFFAOYSA-N 0.000 claims 1
- XMYZDJMUUQJLCQ-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCC1N(CCC1)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCC1N(CCC1)C)N XMYZDJMUUQJLCQ-UHFFFAOYSA-N 0.000 claims 1
- RAFTZYIJUVQCNH-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N RAFTZYIJUVQCNH-UHFFFAOYSA-N 0.000 claims 1
- LOMIJYWNPRFDPB-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N LOMIJYWNPRFDPB-UHFFFAOYSA-N 0.000 claims 1
- QZBKXOLOARSLJJ-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)S(=O)(=O)C)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)S(=O)(=O)C)N QZBKXOLOARSLJJ-UHFFFAOYSA-N 0.000 claims 1
- VOECYEYYGHRAIN-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N VOECYEYYGHRAIN-UHFFFAOYSA-N 0.000 claims 1
- CYZYRWDQICJXML-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N CYZYRWDQICJXML-UHFFFAOYSA-N 0.000 claims 1
- CBTPFJFUUXKXQP-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N CBTPFJFUUXKXQP-UHFFFAOYSA-N 0.000 claims 1
- FAQGFKIXTIOJFS-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N FAQGFKIXTIOJFS-UHFFFAOYSA-N 0.000 claims 1
- FUXUVENJPGDPSH-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N FUXUVENJPGDPSH-UHFFFAOYSA-N 0.000 claims 1
- XXVDEDDCQUTZSI-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N XXVDEDDCQUTZSI-UHFFFAOYSA-N 0.000 claims 1
- NRXIRHZMDREEQJ-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N NRXIRHZMDREEQJ-UHFFFAOYSA-N 0.000 claims 1
- MWRCUAXQMOSQPV-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound ClC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N MWRCUAXQMOSQPV-UHFFFAOYSA-N 0.000 claims 1
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims 1
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims 1
- 206010048554 Endothelial dysfunction Diseases 0.000 claims 1
- VSXRDPWEEBKXTD-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)C(F)(F)F)C1(NC=CC(=N1)NCCCN1CCOCC1)N)(F)F Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C1(NC=CC(=N1)NCCCN1CCOCC1)N)(F)F VSXRDPWEEBKXTD-UHFFFAOYSA-N 0.000 claims 1
- SMYWQFPFFNRMSQ-UHFFFAOYSA-N FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N)(F)F Chemical compound FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N)(F)F SMYWQFPFFNRMSQ-UHFFFAOYSA-N 0.000 claims 1
- HJRPUOKJAUCCOZ-UHFFFAOYSA-N FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CNCC1)N)(F)F Chemical compound FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CNCC1)N)(F)F HJRPUOKJAUCCOZ-UHFFFAOYSA-N 0.000 claims 1
- TWAYSJNOTITWEJ-UHFFFAOYSA-N FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NCCC1)N)(F)F Chemical compound FC(C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NCCC1)N)(F)F TWAYSJNOTITWEJ-UHFFFAOYSA-N 0.000 claims 1
- CIRSOEZAPZWBMG-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N)(F)F Chemical compound FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N)(F)F CIRSOEZAPZWBMG-UHFFFAOYSA-N 0.000 claims 1
- HVXSQTFVCUQKCP-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N)(F)F Chemical compound FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N)(F)F HVXSQTFVCUQKCP-UHFFFAOYSA-N 0.000 claims 1
- KJASWRBBNMWTNM-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N)(F)F Chemical compound FC(C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N)(F)F KJASWRBBNMWTNM-UHFFFAOYSA-N 0.000 claims 1
- RPPUVENMPRRZBZ-UHFFFAOYSA-N FC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound FC=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N RPPUVENMPRRZBZ-UHFFFAOYSA-N 0.000 claims 1
- PWCUANAFWFYGGH-UHFFFAOYSA-N FC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound FC=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N PWCUANAFWFYGGH-UHFFFAOYSA-N 0.000 claims 1
- MELRYPIZEZCSKX-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N MELRYPIZEZCSKX-UHFFFAOYSA-N 0.000 claims 1
- HCWJMLKEWIQIRS-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N HCWJMLKEWIQIRS-UHFFFAOYSA-N 0.000 claims 1
- JQWCEDPQXAISOZ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N JQWCEDPQXAISOZ-UHFFFAOYSA-N 0.000 claims 1
- PMRZMCDQWLATBX-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N PMRZMCDQWLATBX-UHFFFAOYSA-N 0.000 claims 1
- FGISXPJRUIJYGK-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N FGISXPJRUIJYGK-UHFFFAOYSA-N 0.000 claims 1
- ZDGREZAYJJATQZ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N ZDGREZAYJJATQZ-UHFFFAOYSA-N 0.000 claims 1
- WWUVXNJBUVZHLO-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound FC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N WWUVXNJBUVZHLO-UHFFFAOYSA-N 0.000 claims 1
- RSZFBHGEIUECQM-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N RSZFBHGEIUECQM-UHFFFAOYSA-N 0.000 claims 1
- JVMUGEMZFCMCAY-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N JVMUGEMZFCMCAY-UHFFFAOYSA-N 0.000 claims 1
- NUGWWKPUROYUJZ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N NUGWWKPUROYUJZ-UHFFFAOYSA-N 0.000 claims 1
- NXVADEWRGMOPOP-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N NXVADEWRGMOPOP-UHFFFAOYSA-N 0.000 claims 1
- SQHVABQNKPVONV-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N SQHVABQNKPVONV-UHFFFAOYSA-N 0.000 claims 1
- YFOVOPLLIJCWAQ-UHFFFAOYSA-N FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound FC=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N YFOVOPLLIJCWAQ-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 206010027525 Microalbuminuria Diseases 0.000 claims 1
- DNAWHDRCMARGDZ-UHFFFAOYSA-N N1(C=NC=C1)CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1(C=NC=C1)CC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N DNAWHDRCMARGDZ-UHFFFAOYSA-N 0.000 claims 1
- PZJKBBRZXXQYIN-UHFFFAOYSA-N N1(CCOCC1)CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)C1=CC=NC=C1)N Chemical compound N1(CCOCC1)CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)C1=CC=NC=C1)N PZJKBBRZXXQYIN-UHFFFAOYSA-N 0.000 claims 1
- SZNXJBDTQLEHAM-UHFFFAOYSA-N N1(CCOCC1)S(=O)(=O)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1(CCOCC1)S(=O)(=O)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N SZNXJBDTQLEHAM-UHFFFAOYSA-N 0.000 claims 1
- STSHXRXBFFMPKM-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N STSHXRXBFFMPKM-UHFFFAOYSA-N 0.000 claims 1
- DESWMRPNRRTUGY-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N DESWMRPNRRTUGY-UHFFFAOYSA-N 0.000 claims 1
- AYYDYIDXBQRICM-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N AYYDYIDXBQRICM-UHFFFAOYSA-N 0.000 claims 1
- ORIWJYJAWYVHHE-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N ORIWJYJAWYVHHE-UHFFFAOYSA-N 0.000 claims 1
- MPUCUOGTQXPDFU-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N MPUCUOGTQXPDFU-UHFFFAOYSA-N 0.000 claims 1
- GJDWIOLHVCRELI-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N GJDWIOLHVCRELI-UHFFFAOYSA-N 0.000 claims 1
- NXVANQICBJWEQL-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N NXVANQICBJWEQL-UHFFFAOYSA-N 0.000 claims 1
- FBLOZTFBQKUQSQ-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N FBLOZTFBQKUQSQ-UHFFFAOYSA-N 0.000 claims 1
- DIONQYBOKDBZJU-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N DIONQYBOKDBZJU-UHFFFAOYSA-N 0.000 claims 1
- GOJBWVKZQUTJAR-UHFFFAOYSA-N N1=CC(=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1=CC(=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N GOJBWVKZQUTJAR-UHFFFAOYSA-N 0.000 claims 1
- ZHPLMPLPUAEQNN-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N ZHPLMPLPUAEQNN-UHFFFAOYSA-N 0.000 claims 1
- QQYNBRNCDMYLJP-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N QQYNBRNCDMYLJP-UHFFFAOYSA-N 0.000 claims 1
- PTYUKOQGNWSFLU-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N PTYUKOQGNWSFLU-UHFFFAOYSA-N 0.000 claims 1
- KCISGFPNSUCCAS-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N KCISGFPNSUCCAS-UHFFFAOYSA-N 0.000 claims 1
- CQMGNTBLUFWIPG-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N CQMGNTBLUFWIPG-UHFFFAOYSA-N 0.000 claims 1
- SXPFTIBEXJLONZ-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N SXPFTIBEXJLONZ-UHFFFAOYSA-N 0.000 claims 1
- XMWQYKGXACEFEJ-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N XMWQYKGXACEFEJ-UHFFFAOYSA-N 0.000 claims 1
- JDYIQEDSPWWBAH-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N JDYIQEDSPWWBAH-UHFFFAOYSA-N 0.000 claims 1
- BNVZPLHRNNBPCQ-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N BNVZPLHRNNBPCQ-UHFFFAOYSA-N 0.000 claims 1
- NFOXWKJDVDEOGP-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CCOCC1)N NFOXWKJDVDEOGP-UHFFFAOYSA-N 0.000 claims 1
- YCMRSWQINMERTR-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1CN=CC1)N YCMRSWQINMERTR-UHFFFAOYSA-N 0.000 claims 1
- BEXNMYBJJNROBK-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N BEXNMYBJJNROBK-UHFFFAOYSA-N 0.000 claims 1
- NNQHHABHOOVJIB-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N NNQHHABHOOVJIB-UHFFFAOYSA-N 0.000 claims 1
- QXDPZUYOLHODKN-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N QXDPZUYOLHODKN-UHFFFAOYSA-N 0.000 claims 1
- QWAQXOXIOSTYMX-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N QWAQXOXIOSTYMX-UHFFFAOYSA-N 0.000 claims 1
- LCWZSBZBJSXCKC-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N LCWZSBZBJSXCKC-UHFFFAOYSA-N 0.000 claims 1
- JPDYRLZUOGHDEU-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N JPDYRLZUOGHDEU-UHFFFAOYSA-N 0.000 claims 1
- XAWIRDCOUUQYLJ-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N XAWIRDCOUUQYLJ-UHFFFAOYSA-N 0.000 claims 1
- PPSMANYCDRNHMV-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC1)C1(NC=CC(=N1)NCCCN1NC=CC1)N PPSMANYCDRNHMV-UHFFFAOYSA-N 0.000 claims 1
- NYVMGTTYZNKWGB-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N NYVMGTTYZNKWGB-UHFFFAOYSA-N 0.000 claims 1
- SBAFATJYIVOJJH-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N SBAFATJYIVOJJH-UHFFFAOYSA-N 0.000 claims 1
- XWHKXFZVKUGIFY-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N XWHKXFZVKUGIFY-UHFFFAOYSA-N 0.000 claims 1
- FIYRXUSZYOYFMQ-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N FIYRXUSZYOYFMQ-UHFFFAOYSA-N 0.000 claims 1
- WZSFHJQWUGGXMQ-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N WZSFHJQWUGGXMQ-UHFFFAOYSA-N 0.000 claims 1
- NIZVWJJFCWQOPS-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N NIZVWJJFCWQOPS-UHFFFAOYSA-N 0.000 claims 1
- ORWYSVLFUNVDLG-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N ORWYSVLFUNVDLG-UHFFFAOYSA-N 0.000 claims 1
- RLPHWKFLNMZXRO-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N RLPHWKFLNMZXRO-UHFFFAOYSA-N 0.000 claims 1
- FIZHKNPCOSKLHJ-UHFFFAOYSA-N N1C=CC2=C(C=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1C=CC2=C(C=CC=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N FIZHKNPCOSKLHJ-UHFFFAOYSA-N 0.000 claims 1
- SBHNSFBTVQVJSJ-UHFFFAOYSA-N N1C=CC2=CC=C(C=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound N1C=CC2=CC=C(C=C12)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N SBHNSFBTVQVJSJ-UHFFFAOYSA-N 0.000 claims 1
- VURLWIFRRBOQIN-UHFFFAOYSA-N N=1C(N)(C=2C=C(C=CC=2)C=2C3=CC=CC=C3NC=2)NC=CC=1NCCCN1CC=NC1 Chemical compound N=1C(N)(C=2C=C(C=CC=2)C=2C3=CC=CC=C3NC=2)NC=CC=1NCCCN1CC=NC1 VURLWIFRRBOQIN-UHFFFAOYSA-N 0.000 claims 1
- GKGUIFUTRVJOJY-UHFFFAOYSA-N NC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound NC=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N GKGUIFUTRVJOJY-UHFFFAOYSA-N 0.000 claims 1
- 108020001621 Natriuretic Peptide Proteins 0.000 claims 1
- 102000004571 Natriuretic peptide Human genes 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- OCVUGQQBVSWGTC-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound O(C1=CC=CC=C1)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N OCVUGQQBVSWGTC-UHFFFAOYSA-N 0.000 claims 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 1
- 206010061481 Renal injury Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- SUJWISZAFCGORT-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CC=CC1)N SUJWISZAFCGORT-UHFFFAOYSA-N 0.000 claims 1
- YAWHPMSFIZWCTH-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N YAWHPMSFIZWCTH-UHFFFAOYSA-N 0.000 claims 1
- RUDOSIFORCXHSN-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCCC1)N RUDOSIFORCXHSN-UHFFFAOYSA-N 0.000 claims 1
- OXQRVLVVYFGATG-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCN(CC1)C)N OXQRVLVVYFGATG-UHFFFAOYSA-N 0.000 claims 1
- VJANXICMIGZYMV-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCNCC1)N VJANXICMIGZYMV-UHFFFAOYSA-N 0.000 claims 1
- LYPMHTBVKCZRSL-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CNCC1)N LYPMHTBVKCZRSL-UHFFFAOYSA-N 0.000 claims 1
- PKSCGMXNIHFXKB-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N Chemical compound S1C(=NC2=C1C=CC=C2)C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1NCCC1)N PKSCGMXNIHFXKB-UHFFFAOYSA-N 0.000 claims 1
- HLHXEMXREFSJQX-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2CCOCC2)N Chemical compound S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2CCOCC2)N HLHXEMXREFSJQX-UHFFFAOYSA-N 0.000 claims 1
- HESHFPORNWWHFX-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2CN=CC2)N Chemical compound S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2CN=CC2)N HESHFPORNWWHFX-UHFFFAOYSA-N 0.000 claims 1
- VDLOBXSUQGPQCJ-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2NC=CC2)N Chemical compound S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)C2(NC=CC(=N2)NCCCN2NC=CC2)N VDLOBXSUQGPQCJ-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010042434 Sudden death Diseases 0.000 claims 1
- AORYQFCEZUFYOB-UHFFFAOYSA-N [3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]methanol Chemical compound OCC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 AORYQFCEZUFYOB-UHFFFAOYSA-N 0.000 claims 1
- GUSFMBLAWAJVOB-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCOCC1)N GUSFMBLAWAJVOB-UHFFFAOYSA-N 0.000 claims 1
- XYGBUXSNCUMZSL-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CN=CC1)N XYGBUXSNCUMZSL-UHFFFAOYSA-N 0.000 claims 1
- LJRRMJYWOCOQHH-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCCC1)N LJRRMJYWOCOQHH-UHFFFAOYSA-N 0.000 claims 1
- ISVPAUMISOSOFK-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1(NC=CC(=N1)NCCCN1CCOCC1)N ISVPAUMISOSOFK-UHFFFAOYSA-N 0.000 claims 1
- PYKBJRCFILHKBM-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CC=CC1)N PYKBJRCFILHKBM-UHFFFAOYSA-N 0.000 claims 1
- WASHFXNNRZGGIB-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCC1)N WASHFXNNRZGGIB-UHFFFAOYSA-N 0.000 claims 1
- TTXZBWXIWOOUTQ-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCCCC1)N TTXZBWXIWOOUTQ-UHFFFAOYSA-N 0.000 claims 1
- YMNLQKMTBPMBKD-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CCNCC1)N YMNLQKMTBPMBKD-UHFFFAOYSA-N 0.000 claims 1
- QFMXFYJUQFZGAW-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1(NC=CC(=N1)NCCCN1CNCC1)N QFMXFYJUQFZGAW-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 1
- 208000015294 blood coagulation disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 108010010352 cardiac glycoside receptors Proteins 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims 1
- 229960005156 digoxin Drugs 0.000 claims 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000008694 endothelial dysfunction Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 claims 1
- 125000004283 imidazolin-2-yl group Chemical group [H]N1C(*)=NC([H])([H])C1([H])[H] 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000037906 ischaemic injury Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000037806 kidney injury Diseases 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 230000002297 mitogenic effect Effects 0.000 claims 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 230000002107 myocardial effect Effects 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- LPEZZRCMMFATCU-UHFFFAOYSA-N n-(3-chlorophenyl)-3-[[4-(3-pyrrolidin-1-ylpropylamino)pyrimidin-2-yl]amino]benzamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 LPEZZRCMMFATCU-UHFFFAOYSA-N 0.000 claims 1
- YUZPJJQMNYQZEI-UHFFFAOYSA-N n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1)=CC=CC=1NC(N=1)=NC=CC=1NCCCN1CCOCC1 YUZPJJQMNYQZEI-UHFFFAOYSA-N 0.000 claims 1
- YYJQKOHYMQFOKT-UHFFFAOYSA-N n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=1)=CC=CC=1NC(N=1)=NC=CC=1NCCCN1CCOCC1 YYJQKOHYMQFOKT-UHFFFAOYSA-N 0.000 claims 1
- VAHUZOKYOQTOIU-UHFFFAOYSA-N n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=1)=CC=CC=1NC(N=1)=NC=CC=1NCCCN1CCOCC1 VAHUZOKYOQTOIU-UHFFFAOYSA-N 0.000 claims 1
- IXXJOYNCHXMOFS-UHFFFAOYSA-N n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(C=1)=CC=CC=1NC(N=1)=NC=CC=1NCCCN1CCOCC1 IXXJOYNCHXMOFS-UHFFFAOYSA-N 0.000 claims 1
- AGDDSINSUPAYRQ-UHFFFAOYSA-N n-benzyl-3-[[4-(3-pyrrolidin-1-ylpropylamino)pyrimidin-2-yl]amino]benzamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCCC3)C=CN=2)=CC=1C(=O)NCC1=CC=CC=C1 AGDDSINSUPAYRQ-UHFFFAOYSA-N 0.000 claims 1
- QTRQTXKYTWVJBQ-UHFFFAOYSA-N n-propan-2-yl-3-[[4-(3-pyrrolidin-1-ylpropylamino)pyrimidin-2-yl]amino]benzamide Chemical compound CC(C)NC(=O)C1=CC=CC(NC=2N=C(NCCCN3CCCC3)C=CN=2)=C1 QTRQTXKYTWVJBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000692 natriuretic peptide Substances 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004292 pyrrolin-2-yl group Chemical group [H]C1([H])N=C(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003087 receptor blocking agent Substances 0.000 claims 1
- 230000036454 renin-angiotensin system Effects 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81395606P | 2006-06-15 | 2006-06-15 | |
| PCT/US2007/071077 WO2007146981A2 (en) | 2006-06-15 | 2007-06-13 | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase c-alpha |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009540013A JP2009540013A (ja) | 2009-11-19 |
| JP2009540013A5 true JP2009540013A5 (https=) | 2010-07-29 |
Family
ID=38608732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009515622A Pending JP2009540013A (ja) | 2006-06-15 | 2007-06-13 | ２−アニリノ−４−（複素環）アミノ−ピリミジン |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20070293494A1 (https=) |
| EP (1) | EP2054392A2 (https=) |
| JP (1) | JP2009540013A (https=) |
| KR (1) | KR20090019011A (https=) |
| CN (1) | CN101506175A (https=) |
| AR (1) | AR061380A1 (https=) |
| AU (1) | AU2007257650A1 (https=) |
| BR (1) | BRPI0713696A2 (https=) |
| CA (1) | CA2653777A1 (https=) |
| CL (1) | CL2007001749A1 (https=) |
| IL (1) | IL195864A0 (https=) |
| MX (1) | MX2008016004A (https=) |
| RU (1) | RU2008152195A (https=) |
| TW (1) | TW200815424A (https=) |
| WO (1) | WO2007146981A2 (https=) |
| ZA (1) | ZA200809941B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007146977A1 (en) * | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-aminoalkyleneaminopyrimidines |
| EA200901133A1 (ru) * | 2007-03-20 | 2010-04-30 | Смитклайн Бичем Корпорейшн | Производные дианилинопиримидина как ингибиторы киназы wee1, фармацевтическая композиция и применение |
| CA2693594A1 (en) * | 2007-07-17 | 2009-01-22 | Rigel Pharmaceuticals, Inc. | Cyclic amine substituted pyrimidinediamines as pkc inhibitors |
| WO2010083240A2 (en) * | 2009-01-14 | 2010-07-22 | Rigel Pharmaceuticals, Inc. | Methods for treating inflammatory disorders using 2,4-pyrimidinediamine compounds |
| JP5658685B2 (ja) * | 2009-01-14 | 2015-01-28 | ライジェル ファーマシューティカルズ， インコーポレイテッド | 炎症性障害の治療のための２，４−ピリミジンジアミン化合物 |
| ES2555982T3 (es) * | 2009-01-15 | 2016-01-12 | Rigel Pharmaceuticals, Inc. | Inhibidores de la proteína quinasa C y usos de los mismos |
| AR076024A1 (es) * | 2009-04-03 | 2011-05-11 | Schering Corp | Derivados de heterociclos biciclicos puenteados y metodos de uso de los mismos |
| EP2483406A2 (en) | 2009-09-30 | 2012-08-08 | President and Fellows of Harvard College | Methods for modulation of autophagy through the modulation of autophagy-inhibiting gene products |
| US20110130415A1 (en) | 2009-12-01 | 2011-06-02 | Rajinder Singh | Protein kinase c inhibitors and uses thereof |
| JP2013517273A (ja) * | 2010-01-13 | 2013-05-16 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | 化合物および方法 |
| US8927547B2 (en) | 2010-05-21 | 2015-01-06 | Noviga Research Ab | Pyrimidine derivatives |
| DK2688883T3 (en) | 2011-03-24 | 2016-09-05 | Noviga Res Ab | pyrimidine |
| CN104169272A (zh) * | 2011-12-23 | 2014-11-26 | 赛尔佐姆有限公司 | 作为激酶抑制剂的嘧啶-2,4-二胺衍生物 |
| CN102746255A (zh) * | 2012-07-24 | 2012-10-24 | 安徽中医学院 | 具有抗肿瘤活性的化合物、制备方法及应用 |
| MX394360B (es) * | 2013-03-14 | 2025-03-24 | Sumitomo Pharma Oncology Inc | Inhibidores de jak2 y alk2 y metodos para su uso. |
| CN106456700B (zh) | 2014-01-29 | 2020-02-18 | 斯特拉斯堡大学 | 糖尿病治疗和预防的新靶标 |
| EP3206691B1 (en) * | 2014-10-14 | 2018-09-19 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| CA3012288A1 (en) * | 2016-02-22 | 2017-08-31 | F.Hoffmann-La Roche Ag | Process for the manufacture of 3-piperazin-1-yl-propylamine derivatives |
| EP3421485A1 (en) | 2017-06-30 | 2019-01-02 | Université de Strasbourg | Peptides for treatment and prevention of hyperglycaemia |
| CN112533602A (zh) | 2018-04-05 | 2021-03-19 | 大日本住友制药肿瘤公司 | Axl激酶抑制剂及其用途 |
| MX2021000977A (es) | 2018-07-26 | 2021-04-12 | Sumitomo Pharma Oncology Inc | Metodos para tratar enfermedades asociadas con expresion anormal de receptor de activina a tipo 1 (acvr1) e inhibidores de acvr1 para uso en los mismos. |
| EP3966207B1 (en) | 2019-05-10 | 2023-11-01 | Deciphera Pharmaceuticals, LLC | Phenylaminopyrimidine amide autophagy inhibitors and methods of use thereof |
| MX2021013662A (es) | 2019-05-10 | 2022-03-11 | Deciphera Pharmaceuticals Llc | Inhibidores de la autofagia de heteroarilaminopirimidina amida y metodos de uso de estos. |
| IL325201A (en) | 2019-06-17 | 2026-02-01 | Deciphera Pharmaceuticals Llc | Aminopyrimidine amide autophagy inhibitors and methods of using them |
| LT4004002T (lt) | 2019-07-22 | 2024-10-25 | Lupin Limited | Makrocikliniai junginiai kaip sting agonistai ir jų naudojimo būdai bei metodai |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437683A (en) * | 1948-03-16 | Pyrimedine compounds and method of | ||
| GB592928A (en) | 1943-06-11 | 1947-10-03 | Francis Henry Swinden Curd | New pyrimidine compounds |
| US2443305A (en) * | 1948-06-15 | Pyrimidine derivatives | ||
| DE833651C (de) | 1943-11-02 | 1952-03-10 | Ici Ltd | Verfahren zur Herstellung von neuen Pyrimidinabkoemmlingen |
| GB587550A (en) | 1944-09-25 | 1947-04-29 | Francis Henry Swinden Curd | New pyrimidine compounds |
| US3445467A (en) | 1964-05-25 | 1969-05-20 | Ciba Geigy Corp | Biphenyl diphenylalkane and diphenylether compounds,amino - substituted on the phenyl rings |
| FR2244520B1 (https=) | 1973-07-06 | 1977-02-04 | Ugine Kuhlmann | |
| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| CZ299380B6 (cs) | 1998-03-27 | 2008-07-09 | Janssen Pharmaceutica N. V. | Pyrimidinová sloucenina, použití této slouceniny pro prípravu léciva, farmaceutický prostredek tutoslouceninu obsahující, zpusob prípravy tohoto prostredku a uvedené slouceniny a kombinace a produktuvedenou slouceninu obsahující |
| EP0945442A1 (en) | 1998-03-27 | 1999-09-29 | Janssen Pharmaceutica N.V. | Trisubstituted pyrimidine derivatives |
| ES2274634T3 (es) * | 1998-08-29 | 2007-05-16 | Astrazeneca Ab | Compuestos de pirimidina. |
| US6518286B1 (en) * | 1999-03-26 | 2003-02-11 | Astrazeneca Ab | Compounds |
| GB9924092D0 (en) * | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
| EP1257546A1 (en) * | 2000-02-17 | 2002-11-20 | Amgen Inc. | Kinase inhibitors |
| GB0016877D0 (en) * | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| KR100874791B1 (ko) * | 2001-05-29 | 2008-12-18 | 바이엘 쉐링 파마 악티엔게젤샤프트 | Ｃｄｋ-억제 피리미딘, 그의 제조방법 및 약제로서의 용도 |
| US6939874B2 (en) * | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
| US7115617B2 (en) * | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| WO2003026664A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Corporation | 2-phenylamino-4- (5-pyrazolylamino) -pyramidine derivatives as kinase inhibitors, in particular, src kinase inhibitors |
| WO2003040141A1 (en) | 2001-09-28 | 2003-05-15 | Bayer Pharmaceuticals Corporation | Oxazolyl-phenyl-2,4-diamino-pyrimidine compounds and methods for treating hyperproliferative disorders |
| EP1453516A2 (de) | 2001-10-17 | 2004-09-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | 5-substituierte 4-amino-2-phenylamino-pyrimdinderivate und ihre verwendung als beta-amyloid modulatoren |
| ATE407678T1 (de) * | 2001-10-17 | 2008-09-15 | Boehringer Ingelheim Pharma | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
| MXPA04004178A (es) * | 2001-11-01 | 2004-09-06 | Janssen Pharmaceutica Nv | Heteroarilaminas como inhibidores de glucogeno cintasa cinasa 3beta. |
| MXPA04007196A (es) * | 2002-01-23 | 2005-06-08 | Bayer Pharmaceuticals Corp | Inhibidores de rho-quinasa. |
| GB0206215D0 (en) * | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| AR039540A1 (es) | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
| BR0316680A (pt) * | 2002-11-28 | 2005-10-18 | Schering Ag | Pirimidinas inibidoras de chk, pdk e akt, sua produção e uso como agentes farmacêuticos |
| WO2004052862A1 (ja) | 2002-12-10 | 2004-06-24 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびその医薬用途 |
| US20050014753A1 (en) * | 2003-04-04 | 2005-01-20 | Irm Llc | Novel compounds and compositions as protein kinase inhibitors |
| WO2005003103A2 (en) | 2003-06-30 | 2005-01-13 | Astrazeneca Ab | 2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases |
| BRPI0413018B8 (pt) | 2003-07-30 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, e, uso de um composto |
| WO2005013996A2 (en) | 2003-08-07 | 2005-02-17 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
| BRPI0506839A (pt) * | 2004-01-16 | 2007-06-12 | Novartis Ag | composições e métodos para induzir a cardiomiogênese |
| EP1751136B1 (en) * | 2004-05-07 | 2014-07-02 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
| AU2005322855B2 (en) * | 2004-12-30 | 2012-09-20 | Exelixis, Inc. | Pyrimidine derivatives as kinase modulators and method of use |
| DE102005016634A1 (de) | 2005-04-12 | 2006-10-19 | Merck Patent Gmbh | Neuartige Aza-Hetercyclen als Kinase-Inhibitoren |
| WO2006124874A2 (en) * | 2005-05-12 | 2006-11-23 | Kalypsys, Inc. | Inhibitors of b-raf kinase |
| WO2006133426A2 (en) | 2005-06-08 | 2006-12-14 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| EP1746096A1 (en) | 2005-07-15 | 2007-01-24 | 4Sc Ag | 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer |
| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| TW200812645A (en) | 2006-06-15 | 2008-03-16 | Serenex Inc | Tetracycline package formulations |
| TW200808705A (en) | 2006-06-15 | 2008-02-16 | Sanofi Aventis | Aryl- and heteroaryl-ethyl-acylguanidine derivatives, their preparation and their application in therapeutics |
| WO2007146977A1 (en) | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-aminoalkyleneaminopyrimidines |
| US20080039433A1 (en) | 2006-06-15 | 2008-02-14 | Smith Alexander D | Stabilized Tetracycline Compositions |
| CL2009000600A1 (es) * | 2008-03-20 | 2010-05-07 | Bayer Cropscience Ag | Uso de compuestos de diaminopirimidina como agentes fitosanitarios; compuestos de diaminopirimidina; su procedimiento de preparacion; agente que los contiene; procedimiento para la preparacion de dicho agente; y procedimiento para combatir plagas de animales y/u hongos dañinos patogenos de plantas. |
| EP2297097A2 (en) * | 2008-06-11 | 2011-03-23 | Irm Llc | Compounds and compositions useful for the treatment of malaria |
| WO2010045306A2 (en) * | 2008-10-16 | 2010-04-22 | Schering Corporation | Azine derivatives and methods of use thereof |
| US20110071158A1 (en) * | 2009-03-18 | 2011-03-24 | Boehringer Ingelheim International Gmbh | New compounds |
| US8410126B2 (en) | 2009-05-29 | 2013-04-02 | Boehringer Ingelheim International Gmbh | Pyrimidine inhibitors of PKTK2 |
-
2007
- 2007-06-13 RU RU2008152195/04A patent/RU2008152195A/ru unknown
- 2007-06-13 BR BRPI0713696-0A patent/BRPI0713696A2/pt not_active IP Right Cessation
- 2007-06-13 JP JP2009515622A patent/JP2009540013A/ja active Pending
- 2007-06-13 AU AU2007257650A patent/AU2007257650A1/en not_active Abandoned
- 2007-06-13 WO PCT/US2007/071077 patent/WO2007146981A2/en not_active Ceased
- 2007-06-13 MX MX2008016004A patent/MX2008016004A/es not_active Application Discontinuation
- 2007-06-13 CA CA002653777A patent/CA2653777A1/en not_active Abandoned
- 2007-06-13 US US11/762,394 patent/US20070293494A1/en not_active Abandoned
- 2007-06-13 CN CNA2007800303500A patent/CN101506175A/zh active Pending
- 2007-06-13 KR KR1020097000717A patent/KR20090019011A/ko not_active Withdrawn
- 2007-06-13 EP EP07798482A patent/EP2054392A2/en not_active Withdrawn
- 2007-06-14 TW TW096121541A patent/TW200815424A/zh unknown
- 2007-06-14 CL CL2007001749A patent/CL2007001749A1/es unknown
- 2007-06-15 AR ARP070102631A patent/AR061380A1/es not_active Application Discontinuation
-
2008
- 2008-11-24 ZA ZA200809941A patent/ZA200809941B/xx unknown
- 2008-12-11 IL IL195864A patent/IL195864A0/en unknown
-
2009
- 2009-05-14 US US12/465,704 patent/US8354407B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009540013A5 (https=) | ||
| RU2008152195A (ru) | 2-анилино-4-(гетероциклил)аминопиримидины, как ингибиторы протеинкиназы с-альфа | |
| TW523511B (en) | Pharmaceutical composition comprising substituted imidazole compounds and process for preparing compounds | |
| US9365539B2 (en) | Prolylcarboxypeptidase inhibitors | |
| TWI336699B (en) | Stat3/5 activation inhibitor | |
| CN1261098C (zh) | p38－α激酶的抑制剂 | |
| SU1297728A3 (ru) | Способ получени @ -гетероциклил-4-пиперидинаминов или их фармацевтически приемлемых солей | |
| AU2008251584B2 (en) | 2-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-3-phenyl pyrazines and pyridines and 3-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-2-phenyl pyridines as 5-HT7 receptor antagonists | |
| CA2437767A1 (en) | Heterocyclic inhibitors of erk2 and uses thereof | |
| JPWO2020038415A5 (https=) | ||
| EA010690B1 (ru) | Трёхзамещённые производные арилов и гетероарилов в качестве модуляторов метаболизма и профилактика и лечение связанных с ними нарушений | |
| CN101616587A (zh) | 吲唑化合物 | |
| DK2621916T3 (en) | Benzazole derivatives as histamine H 4 receptor ligands | |
| JPH08502508A (ja) | ドーパミンレセプターサブタイプリガンド | |
| JPWO2021170109A5 (https=) | ||
| US20040229927A1 (en) | Imidazole derivatives for treatment of allergic and hyperproliferative disorders | |
| EP0882023B1 (en) | Histamine h 3 receptor ligands | |
| SU1694064A3 (ru) | Способ получени N-/бициклических гетероцикло)-4-пиперидинаминов, фармацевтически приемлемой соли присоединени кислоты или стереохимически возможной изомерной ее формы | |
| JPWO2020165834A5 (https=) | ||
| US20130085161A1 (en) | Piperidinyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives | |
| TW211010B (https=) | ||
| JP2007505085A (ja) | ベンゾイミダゾールアセトニトリル | |
| TW200301122A (en) | Kinase inhibitors | |
| JP2009537606A5 (https=) | ||
| KR20010108499A (ko) | 인테그린 수용체 리간드 |