KR20080095902A - 단백질 키나제의 억제제로서 유용한 디하이드로디아제핀 - Google Patents
단백질 키나제의 억제제로서 유용한 디하이드로디아제핀 Download PDFInfo
- Publication number
- KR20080095902A KR20080095902A KR1020087022521A KR20087022521A KR20080095902A KR 20080095902 A KR20080095902 A KR 20080095902A KR 1020087022521 A KR1020087022521 A KR 1020087022521A KR 20087022521 A KR20087022521 A KR 20087022521A KR 20080095902 A KR20080095902 A KR 20080095902A
- Authority
- KR
- South Korea
- Prior art keywords
- aliphatic
- compound
- formula
- optionally substituted
- cyclopentyl
- 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.)
- Abandoned
Links
- 0 C(*1)[C@]1c1ccccc1 Chemical compound C(*1)[C@]1c1ccccc1 0.000 description 3
- NHTJBDCHGVHNHO-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O NHTJBDCHGVHNHO-UHFFFAOYSA-N 0.000 description 2
- OJMFTGXNNVNPKN-UHFFFAOYSA-N CC(C)(C)NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O Chemical compound CC(C)(C)NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O OJMFTGXNNVNPKN-UHFFFAOYSA-N 0.000 description 1
- FOKSQPBKSFBTBZ-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O)=O Chemical compound CC(C)(C)OC(N(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O)=O FOKSQPBKSFBTBZ-UHFFFAOYSA-N 0.000 description 1
- WSFFEQOBKFCVFA-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O)=O Chemical compound CC(C)(C)OC(N(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O)=O WSFFEQOBKFCVFA-UHFFFAOYSA-N 0.000 description 1
- YITBTQBRZJZBGW-UHFFFAOYSA-N CC(C)(CN(C(CC1)CC1c1cc(NC(c(cc2)cc(OC)c2Nc(nc2)n3)=O)n[nH]1)c3c2N1C)C1=O Chemical compound CC(C)(CN(C(CC1)CC1c1cc(NC(c(cc2)cc(OC)c2Nc(nc2)n3)=O)n[nH]1)c3c2N1C)C1=O YITBTQBRZJZBGW-UHFFFAOYSA-N 0.000 description 1
- ZNFFJMXGCBIZTO-XUTJKUGGSA-N CC(C)(CN(C1=CCCC1)c(nc(Nc(ccc(C(N[C@H](CC1)CC[C@@H]1O)=O)c1)c1[O]=C)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1=CCCC1)c(nc(Nc(ccc(C(N[C@H](CC1)CC[C@@H]1O)=O)c1)c1[O]=C)nc1)c1N1C)C1=O ZNFFJMXGCBIZTO-XUTJKUGGSA-N 0.000 description 1
- DNKFEIHYIKJNCO-UHFFFAOYSA-N CC(C)(CN(C1C=CCC1)c(nc(Nc1ccccc1)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1C=CCC1)c(nc(Nc1ccccc1)nc1)c1N1C)C1=O DNKFEIHYIKJNCO-UHFFFAOYSA-N 0.000 description 1
- WWMYXBHGWNEGRQ-UHFFFAOYSA-N CC(C)(CN(C1CC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O WWMYXBHGWNEGRQ-UHFFFAOYSA-N 0.000 description 1
- AKYWOSJCHOXPER-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(cc1)ccc1N)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(cc1)ccc1N)nc1)c1N1C)C1=O AKYWOSJCHOXPER-UHFFFAOYSA-N 0.000 description 1
- IKOYBKSNMRYXOZ-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC#N)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC#N)=O)c1)c1OC)nc1)c1N1C)C1=O IKOYBKSNMRYXOZ-UHFFFAOYSA-N 0.000 description 1
- VFFPTWCWZUWXER-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC(CO)O)=O)c1)c1OC)nc1)c1N1C)C1O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC(CO)O)=O)c1)c1OC)nc1)c1N1C)C1O VFFPTWCWZUWXER-UHFFFAOYSA-N 0.000 description 1
- QAJALZJPTGXLHN-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC1CCCC1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC1CCCC1)=O)c1)c1OC)nc1)c1N1C)C1=O QAJALZJPTGXLHN-UHFFFAOYSA-N 0.000 description 1
- OXXJYEQIPPCKQH-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC1CCOCC1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCC1CCOCC1)=O)c1)c1OC)nc1)c1N1C)C1=O OXXJYEQIPPCKQH-UHFFFAOYSA-N 0.000 description 1
- DLESGSRAZVKIHG-FQEVSTJZSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCCN(CC1)C[C@H]1F)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NCCN(CC1)C[C@H]1F)=O)c1)c1OC)nc1)c1N1C)C1=O DLESGSRAZVKIHG-FQEVSTJZSA-N 0.000 description 1
- CKQZCQICBPGDBO-HKWDBMNNSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NC[C@H](CCCC1)[C@@H]1O)=O)c1)c1OC)nc1)c1N1C)C1O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(NC[C@H](CCCC1)[C@@H]1O)=O)c1)c1OC)nc1)c1N1C)C1O CKQZCQICBPGDBO-HKWDBMNNSA-N 0.000 description 1
- QWTKTHIBCCBSCV-UYAOXDASSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(N[C@H](CC1)C[C@@H]1O)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(N[C@H](CC1)C[C@@H]1O)=O)c1)c1OC)nc1)c1N1C)C1=O QWTKTHIBCCBSCV-UYAOXDASSA-N 0.000 description 1
- ZBKMGNOJOBNPAA-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc(cccn1)c1OC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc(cccn1)c1OC)=O)c1)c1OC)nc1)c1N1C)C1=O ZBKMGNOJOBNPAA-UHFFFAOYSA-N 0.000 description 1
- VQABXGLCIBLPOI-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc1ccnc(Cl)c1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc1ccnc(Cl)c1)=O)c1)c1OC)nc1)c1N1C)C1=O VQABXGLCIBLPOI-UHFFFAOYSA-N 0.000 description 1
- GCQXFBJDTOLBTF-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc1nccnc1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C(Nc1nccnc1)=O)c1)c1OC)nc1)c1N1C)C1=O GCQXFBJDTOLBTF-UHFFFAOYSA-N 0.000 description 1
- ONIVTPSMIVIGHU-UHFFFAOYSA-O CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C([NH3+])=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc(ccc(C([NH3+])=O)c1)c1OC)nc1)c1N1C)C1=O ONIVTPSMIVIGHU-UHFFFAOYSA-O 0.000 description 1
- RRCJECRZJOIAPR-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc1cccc(C(NC2CC2)=O)c1)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc1cccc(C(NC2CC2)=O)c1)nc1)c1N1C)C1=O RRCJECRZJOIAPR-UHFFFAOYSA-N 0.000 description 1
- LUZHCQWNCOYFSK-UHFFFAOYSA-N CC(C)(CN(C1CCCC1)c(nc(Nc1cccc([N+]([O-])=O)c1)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc(Nc1cccc([N+]([O-])=O)c1)nc1)c1N1C)C1=O LUZHCQWNCOYFSK-UHFFFAOYSA-N 0.000 description 1
- HNEUKTYZPMHPDO-UHFFFAOYSA-O CC(C)(CN(C1CCCC1)c(nc([NH2+]c(ccc(C(Nc1ncc[s]1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc([NH2+]c(ccc(C(Nc1ncc[s]1)=O)c1)c1OC)nc1)c1N1C)C1=O HNEUKTYZPMHPDO-UHFFFAOYSA-O 0.000 description 1
- LRLFTGOMOBGFBF-UHFFFAOYSA-O CC(C)(CN(C1CCCC1)c(nc([NH2+]c1cccc2c1nc[nH]2)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCCC1)c(nc([NH2+]c1cccc2c1nc[nH]2)nc1)c1N1C)C1=O LRLFTGOMOBGFBF-UHFFFAOYSA-O 0.000 description 1
- KHFRBXATZIZXOE-UHFFFAOYSA-N CC(C)(CN(C1CCN(C)CC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(C)(CN(C1CCN(C)CC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O KHFRBXATZIZXOE-UHFFFAOYSA-N 0.000 description 1
- HGIQFVGANLZKQU-UHFFFAOYSA-N CC(CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCN(C)CC1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCN(C)CC1)=O)c1)c1OC)nc1)c1N1C)C1=O HGIQFVGANLZKQU-UHFFFAOYSA-N 0.000 description 1
- VFBAFXHFFOATDK-UHFFFAOYSA-N CC(CN(C1CCCC1)c(nc(Nc(ccc(C(O)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound CC(CN(C1CCCC1)c(nc(Nc(ccc(C(O)=O)c1)c1OC)nc1)c1N1C)C1=O VFBAFXHFFOATDK-UHFFFAOYSA-N 0.000 description 1
- YEMCNVLASQBVDV-UHFFFAOYSA-N CC(c1ccccc1)NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O Chemical compound CC(c1ccccc1)NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2=O)=O YEMCNVLASQBVDV-UHFFFAOYSA-N 0.000 description 1
- HXRHBOFIVVVXCJ-UHFFFAOYSA-N CC1(C(NC(NC2(C)N(CC3(C)C)C4C=CCCC4)=NC=C2N(C)C3=O)=CC=C2)N2N=CN1 Chemical compound CC1(C(NC(NC2(C)N(CC3(C)C)C4C=CCCC4)=NC=C2N(C)C3=O)=CC=C2)N2N=CN1 HXRHBOFIVVVXCJ-UHFFFAOYSA-N 0.000 description 1
- VWSLLSXLURJCDF-UHFFFAOYSA-N CC1=NCCN1 Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- FRBWMVPZFAKPOU-UHFFFAOYSA-N CCCN(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2O)=O Chemical compound CCCN(CC1)CCC1NC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2(C)C)C3CCCC3)c1N(C)C2O)=O FRBWMVPZFAKPOU-UHFFFAOYSA-N 0.000 description 1
- HNXAAGSXTCHYMR-UHFFFAOYSA-N CC[IH][IH]CN(c1c(N(C)CC2)nc(Nc(c(OC)c3)ccc3C(NC3CCN(C)CC3)=O)nc1)C2=O Chemical compound CC[IH][IH]CN(c1c(N(C)CC2)nc(Nc(c(OC)c3)ccc3C(NC3CCN(C)CC3)=O)nc1)C2=O HNXAAGSXTCHYMR-UHFFFAOYSA-N 0.000 description 1
- PWOVFKYKHWLQOD-UHFFFAOYSA-N CN(CC1)CCC1NC(c(cc1)ccc1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O Chemical compound CN(CC1)CCC1NC(c(cc1)ccc1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O PWOVFKYKHWLQOD-UHFFFAOYSA-N 0.000 description 1
- PLDKMKLIFOBOSW-UHFFFAOYSA-N CN(c1c(N(CC2)C3CCCC3)nc(Nc(ccc(C(NC3CCNCC3)=O)c3)c3OC)nc1)C2=O Chemical compound CN(c1c(N(CC2)C3CCCC3)nc(Nc(ccc(C(NC3CCNCC3)=O)c3)c3OC)nc1)C2=O PLDKMKLIFOBOSW-UHFFFAOYSA-N 0.000 description 1
- IFGUGZRRPFBJKI-UHFFFAOYSA-N CN(c1c(N(CC2)C3CCCC3)nc(Nc(ccc(C(NCCOC)=O)c3)c3OC)nc1)C2=O Chemical compound CN(c1c(N(CC2)C3CCCC3)nc(Nc(ccc(C(NCCOC)=O)c3)c3OC)nc1)C2=O IFGUGZRRPFBJKI-UHFFFAOYSA-N 0.000 description 1
- COHHQNBDIDGAKH-QSVWIEALSA-N CN(c1c(N(CC23CC2)C2CCCC2)nc(Nc(ccc(C(N[C@H](CC2)CC2O)=O)c2)c2OC)nc1)C3=O Chemical compound CN(c1c(N(CC23CC2)C2CCCC2)nc(Nc(ccc(C(N[C@H](CC2)CC2O)=O)c2)c2OC)nc1)C3=O COHHQNBDIDGAKH-QSVWIEALSA-N 0.000 description 1
- XBWVKVCSCJYKTP-UHFFFAOYSA-N CNC(c(cc1)cc(OC)c1Nc(nc1)nc(N(C2CCCC2)C2C3CCC2)c1N(C)C3=O)=O Chemical compound CNC(c(cc1)cc(OC)c1Nc(nc1)nc(N(C2CCCC2)C2C3CCC2)c1N(C)C3=O)=O XBWVKVCSCJYKTP-UHFFFAOYSA-N 0.000 description 1
- AWMSNCZDEVVICA-UHFFFAOYSA-N CNC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O Chemical compound CNC(c(cc1)cc(OC)c1Nc(nc1)nc(N(CC2)C3CCCC3)c1N(C)C2=O)=O AWMSNCZDEVVICA-UHFFFAOYSA-N 0.000 description 1
- JWIYBGVEKGCORU-AWEZNQCLSA-N C[C@@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound C[C@@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O JWIYBGVEKGCORU-AWEZNQCLSA-N 0.000 description 1
- JWIYBGVEKGCORU-CQSZACIVSA-N C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC)=O)c1)c1OC)nc1)c1N1C)C1=O JWIYBGVEKGCORU-CQSZACIVSA-N 0.000 description 1
- ANTWPJPZFVLZPS-MRXNPFEDSA-N C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCC1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCC1)=O)c1)c1OC)nc1)c1N1C)C1=O ANTWPJPZFVLZPS-MRXNPFEDSA-N 0.000 description 1
- VFQMKZZWWOPBKX-QGZVFWFLSA-N C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCCC1)=O)c1)c1OC)nc1)c1N1C)C1=O Chemical compound C[C@H](CN(C1CCCC1)c(nc(Nc(ccc(C(NC1CCCC1)=O)c1)c1OC)nc1)c1N1C)C1=O VFQMKZZWWOPBKX-QGZVFWFLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77299206P | 2006-02-14 | 2006-02-14 | |
| US60/772,992 | 2006-02-14 | ||
| US83137106P | 2006-07-17 | 2006-07-17 | |
| US60/831,371 | 2006-07-17 | ||
| US84935306P | 2006-10-04 | 2006-10-04 | |
| US60/849,353 | 2006-10-04 | ||
| US87620606P | 2006-12-21 | 2006-12-21 | |
| US60/876,206 | 2006-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080095902A true KR20080095902A (ko) | 2008-10-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087022521A Abandoned KR20080095902A (ko) | 2006-02-14 | 2007-02-13 | 단백질 키나제의 억제제로서 유용한 디하이드로디아제핀 |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US7622463B2 (https=) |
| EP (1) | EP1983987B1 (https=) |
| JP (2) | JP5243970B2 (https=) |
| KR (1) | KR20080095902A (https=) |
| AR (1) | AR059505A1 (https=) |
| AT (1) | ATE479434T1 (https=) |
| AU (1) | AU2007215221C1 (https=) |
| CA (1) | CA2652648C (https=) |
| DE (1) | DE602007008837D1 (https=) |
| IL (1) | IL193240A0 (https=) |
| NO (1) | NO20083918L (https=) |
| NZ (1) | NZ570530A (https=) |
| RU (1) | RU2475488C2 (https=) |
| TW (1) | TW200804389A (https=) |
| WO (1) | WO2007095188A2 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220125156A (ko) | 2021-03-04 | 2022-09-14 | 한양대학교 에리카산학협력단 | 피리디닐 피라졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
| KR20230076333A (ko) | 2021-11-24 | 2023-05-31 | 한양대학교 에리카산학협력단 | 이속사졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
| US12552768B2 (en) | 2021-03-04 | 2026-02-17 | Industry-University Cooperation Foundation | Pyridinylpyrazole derivative or pharmaceutically acceptable salt thereof and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200808325A (en) * | 2006-07-06 | 2008-02-16 | Astrazeneca Ab | Novel compounds |
| AU2008228303B2 (en) * | 2007-03-22 | 2012-04-19 | Takeda Pharmaceutical Company Limited | Substituted pyrimidodiazepines useful as PLK1 inhibitors |
| TW200914457A (en) * | 2007-05-31 | 2009-04-01 | Kyowa Hakko Kogyo Kk | Pyrimidodiazepinone derivative |
| JP5129812B2 (ja) * | 2007-06-15 | 2013-01-30 | Msd株式会社 | ビシクロアニリン誘導体 |
| AU2008287339A1 (en) * | 2007-08-15 | 2009-02-19 | Vertex Pharmaceuticals Incorporated | 4-(9-(3, 3-difluorocyclopentyl) -5, 7, 7-trimethyl-6-oxo-6, 7, 8, 9-tetrahydro-5H-pyrimido [4, 5-b][1, 4] diazepin-2-ylamino)-3-methoxybenzamide Derivatives as Inhibitors of the Human Protein Kinases PLK1 to PLK4 for the Treatment of Proliferative Diseases |
| EP2205241B1 (en) | 2007-09-25 | 2014-05-21 | Takeda Pharmaceutical Company Limited | Polo-like kinase inhibitors |
| PL2205603T3 (pl) | 2007-09-28 | 2014-07-31 | Cyclacel Ltd | Pochodne pirymidyny jako inhibitory kinaz białkowych |
| US20090291938A1 (en) * | 2007-11-19 | 2009-11-26 | Takeda Pharmaceutical Company Limited | Polo-like kinase inhibitors |
| WO2009071480A2 (en) * | 2007-12-04 | 2009-06-11 | Nerviano Medical Sciences S.R.L. | Substituted dihydropteridin-6-one derivatives, process for their preparation and their use as kinase inhibitors |
| EP2303889A1 (en) | 2008-06-18 | 2011-04-06 | F. Hoffmann-La Roche AG | Halo-substituted pyrimidodiazepines as plkl inhibitors |
| AU2009271658B2 (en) * | 2008-06-23 | 2014-04-10 | Vertex Pharmaceuticals Incorporated | Protein kinase inhibitors |
| MX2011000021A (es) | 2008-06-23 | 2011-02-24 | Vertex Pharma | Inhibidores de proteina cinasas. |
| RS53347B (sr) | 2008-12-09 | 2014-10-31 | Gilead Sciences, Inc. | Modulatori toll-sličnih receptora |
| EP3828185B1 (en) * | 2009-01-06 | 2024-11-20 | Dana-Farber Cancer Institute, Inc. | Pyrimido-diazepinone kinase scaffold compounds and methods of treating disorders |
| AU2010232644A1 (en) * | 2009-03-31 | 2011-10-20 | Arqule, Inc. | Substituted tetrahydropyrazolo-pyrido-azepin compounds |
| LT3141252T (lt) | 2009-06-17 | 2018-11-12 | Vertex Pharmaceuticals Inc. | Gripo virusų replikacijos inhibitoriai |
| CN102548994A (zh) | 2009-09-25 | 2012-07-04 | 沃泰克斯药物股份有限公司 | 用于制备用作蛋白激酶抑制剂的嘧啶衍生物的方法 |
| CN103492391A (zh) * | 2009-09-25 | 2014-01-01 | 沃泰克斯药物股份有限公司 | 用于制备用作蛋白激酶抑制剂的嘧啶衍生物的方法 |
| TW201201813A (en) | 2010-03-31 | 2012-01-16 | Arqule Inc | Substituted benzo-pyrido-triazolo-diazepine compounds |
| PL2902030T3 (pl) | 2010-05-14 | 2017-07-31 | Dana-Farber Cancer Institute, Inc. | Związki tienotriazolodiazepinowe do leczenia nowotworu |
| MX354217B (es) | 2010-05-14 | 2018-02-19 | Dana Farber Cancer Inst Inc | Composiciones y metodos para el tratamiento de leucemia. |
| EP2571875A4 (en) | 2010-05-14 | 2013-10-30 | Dana Farber Cancer Inst Inc | CONTRACEPTIVE COMPOSITIONS FOR MEN AND METHODS OF USE THEREOF |
| ES2706066T3 (es) | 2010-07-02 | 2019-03-27 | Univ Health Network | Procedimiento dirigido a enfermedades mutantes con PTEN y composiciones para las mismas |
| RU2013132681A (ru) | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| WO2014159392A1 (en) | 2013-03-14 | 2014-10-02 | Dana-Farber Cancer Institute, Inc. | Bromodomain binding reagents and uses thereof |
| WO2014145909A2 (en) | 2013-03-15 | 2014-09-18 | Dana-Farber Cancer Institute, Inc. | Pyrimido-diazepinone compounds and methods of treating disorders |
| US9975896B2 (en) | 2013-07-25 | 2018-05-22 | Dana-Farber Cancer Institute, Inc. | Inhibitors of transcription factors and uses thereof |
| RU2016122654A (ru) | 2013-11-08 | 2017-12-14 | Дана-Фарбер Кэнсер Инститьют, Инк. | Комбинированная терапия злокачественной опухоли с использованием ингибиторов бромодоменового и экстратерминального (вет) белка |
| JP6618901B2 (ja) | 2013-11-13 | 2019-12-11 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| LT3068776T (lt) | 2013-11-13 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Gripo virusų replikacijos inhibitoriai |
| EP3099677A4 (en) | 2014-01-31 | 2017-07-26 | Dana-Farber Cancer Institute, Inc. | Diaminopyrimidine benzenesulfone derivatives and uses thereof |
| US10793571B2 (en) | 2014-01-31 | 2020-10-06 | Dana-Farber Cancer Institute, Inc. | Uses of diazepane derivatives |
| CN105940005A (zh) | 2014-01-31 | 2016-09-14 | 达纳-法伯癌症研究所股份有限公司 | 二氮杂环庚烷衍生物及其用途 |
| JP2017506666A (ja) | 2014-02-28 | 2017-03-09 | テンシャ セラピューティクス,インコーポレイテッド | 高インスリン血症に関連した症状の処置 |
| GB201411581D0 (en) * | 2014-06-30 | 2014-08-13 | Inst Europ Di Oncologia S R L | Compounds inhibiting the enzyme monopolar spindle 1 kinase, pharmaceutical compositions and uses thereof |
| JP6522732B2 (ja) | 2014-07-11 | 2019-05-29 | ギリアード サイエンシーズ, インコーポレイテッド | Hivを治療するためのトール様受容体の調節因子 |
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| CN106793775B (zh) | 2014-08-08 | 2020-06-02 | 达纳-法伯癌症研究所股份有限公司 | 二氢碟啶酮衍生物及其用途 |
| SG11201701520TA (en) | 2014-09-16 | 2017-04-27 | Gilead Sciences Inc | Solid forms of a toll-like receptor modulator |
| KR20170068597A (ko) | 2014-10-27 | 2017-06-19 | 텐샤 세러퓨틱스 인코포레이티드 | 브로모도메인 저해제 |
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| EP3294717B1 (en) | 2015-05-13 | 2020-07-29 | Vertex Pharmaceuticals Inc. | Methods of preparing inhibitors of influenza viruses replication |
| EP3294735B8 (en) | 2015-05-13 | 2022-01-05 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
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| RU2018112953A (ru) | 2015-09-11 | 2019-10-14 | Дана-Фарбер Кэнсер Инститьют, Инк. | Ацетамидтиенотриазолодиазепины и пути их применения |
| EP3347021A4 (en) | 2015-09-11 | 2019-07-24 | Dana-Farber Cancer Institute, Inc. | CYANOTHIENOTRIAZOLDIAZEPINE AND USES THEREOF |
| MX2018006499A (es) | 2015-11-25 | 2018-08-01 | Dana Farber Cancer Inst Inc | Inhibidores de bromodominio bivalentes y usos de los mismos. |
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| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| CA3216162A1 (en) | 2021-04-16 | 2022-10-20 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
| AU2022328698B2 (en) | 2021-08-18 | 2025-02-20 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
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| JPS5638032B2 (https=) | 1972-08-31 | 1981-09-03 | ||
| US3872122A (en) * | 1973-04-16 | 1975-03-18 | Bristol Myers Co | 11 H-Pyrimido{8 4,5-b{9 {8 1,4{9 benzodiazepines |
| US3880855A (en) * | 1973-04-16 | 1975-04-29 | Bristol Myers Co | 5,6-DIHYDRO-11-H-pyrimido{8 4,5-b{9 {8 1,4{9 benzodiazepines |
| JPS51110202A (en) | 1975-03-24 | 1976-09-29 | Susumu Nojima | Denwakyono hyojisochi |
| GB8927872D0 (en) | 1989-12-08 | 1990-02-14 | Beecham Group Plc | Pharmaceuticals |
| US6011029A (en) * | 1996-02-26 | 2000-01-04 | Bristol-Myers Squibb Company | Inhibitors of farnesyl protein transferase |
| US7169778B2 (en) | 1999-09-15 | 2007-01-30 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| MXPA02002938A (es) * | 1999-09-17 | 2004-12-06 | Abbott Gmbh & Co Kg | Inhibidores de cinasa como agentes agentes terapeuticos. |
| US7101869B2 (en) * | 1999-11-30 | 2006-09-05 | Pfizer Inc. | 2,4-diaminopyrimidine compounds useful as immunosuppressants |
| MXPA02005350A (es) | 1999-11-30 | 2002-12-11 | Pfizer Prod Inc | Compuestos de 2,4-diamino pirimidina utiles como supresores de inmunidad. |
| UA76512C2 (en) | 2001-09-04 | 2006-08-15 | Boehringer Ingelheim Pharma | Dihydropteridinones, a method for producing thereof and use thereof as medicament |
| JP3876265B2 (ja) | 2003-02-26 | 2007-01-31 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ジヒドロプテリジノン、その製造方法及び薬物形態での使用 |
| US6861422B2 (en) * | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| DE102004029784A1 (de) | 2004-06-21 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004058337A1 (de) | 2004-12-02 | 2006-06-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten |
| EP2205241B1 (en) | 2007-09-25 | 2014-05-21 | Takeda Pharmaceutical Company Limited | Polo-like kinase inhibitors |
| PL2205603T3 (pl) | 2007-09-28 | 2014-07-31 | Cyclacel Ltd | Pochodne pirymidyny jako inhibitory kinaz białkowych |
| JP4941835B2 (ja) | 2007-09-28 | 2012-05-30 | Toto株式会社 | キャビネット及びキャビネットの施工方法 |
| JP5035192B2 (ja) | 2008-09-19 | 2012-09-26 | コニカミノルタアドバンストレイヤー株式会社 | 駆動機構、駆動装置 |
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2007
- 2007-02-13 US US11/706,070 patent/US7622463B2/en active Active
- 2007-02-13 KR KR1020087022521A patent/KR20080095902A/ko not_active Abandoned
- 2007-02-13 RU RU2008136854/04A patent/RU2475488C2/ru not_active IP Right Cessation
- 2007-02-13 TW TW096105339A patent/TW200804389A/zh unknown
- 2007-02-13 CA CA2652648A patent/CA2652648C/en active Active
- 2007-02-13 NZ NZ570530A patent/NZ570530A/en unknown
- 2007-02-13 AT AT07750530T patent/ATE479434T1/de active
- 2007-02-13 WO PCT/US2007/003699 patent/WO2007095188A2/en not_active Ceased
- 2007-02-13 JP JP2008555299A patent/JP5243970B2/ja active Active
- 2007-02-13 EP EP07750530A patent/EP1983987B1/en active Active
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2008
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2009
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2011
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2013
- 2013-01-21 US US13/745,968 patent/US20140038935A1/en not_active Abandoned
- 2013-01-23 JP JP2013009857A patent/JP2013067666A/ja not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220125156A (ko) | 2021-03-04 | 2022-09-14 | 한양대학교 에리카산학협력단 | 피리디닐 피라졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
| US12552768B2 (en) | 2021-03-04 | 2026-02-17 | Industry-University Cooperation Foundation | Pyridinylpyrazole derivative or pharmaceutically acceptable salt thereof and use thereof |
| KR20230076333A (ko) | 2021-11-24 | 2023-05-31 | 한양대학교 에리카산학협력단 | 이속사졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
| KR20230170623A (ko) | 2021-11-24 | 2023-12-19 | 한양대학교 에리카산학협력단 | 이속사졸 유도체 또는 이의 약학적으로 허용가능한 염 및 이의 용도 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200804389A (en) | 2008-01-16 |
| NO20083918L (no) | 2008-11-12 |
| US20080167289A1 (en) | 2008-07-10 |
| NZ570530A (en) | 2011-09-30 |
| US8022202B2 (en) | 2011-09-20 |
| AU2007215221A1 (en) | 2007-08-23 |
| US7622463B2 (en) | 2009-11-24 |
| US20140038935A1 (en) | 2014-02-06 |
| RU2008136854A (ru) | 2010-03-20 |
| AR059505A1 (es) | 2008-04-09 |
| US20100190765A1 (en) | 2010-07-29 |
| HK1129298A1 (en) | 2009-11-27 |
| ATE479434T1 (de) | 2010-09-15 |
| EP1983987B1 (en) | 2010-09-01 |
| JP2013067666A (ja) | 2013-04-18 |
| JP2009526849A (ja) | 2009-07-23 |
| US20120149898A1 (en) | 2012-06-14 |
| CA2652648C (en) | 2016-10-25 |
| DE602007008837D1 (de) | 2010-10-14 |
| IL193240A0 (en) | 2009-08-03 |
| EP1983987A2 (en) | 2008-10-29 |
| US8394952B2 (en) | 2013-03-12 |
| WO2007095188A3 (en) | 2007-10-25 |
| RU2475488C2 (ru) | 2013-02-20 |
| WO2007095188A2 (en) | 2007-08-23 |
| AU2007215221C1 (en) | 2013-05-30 |
| AU2007215221B2 (en) | 2013-01-17 |
| CA2652648A1 (en) | 2007-08-23 |
| JP5243970B2 (ja) | 2013-07-24 |
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