JP5334414B2 - 新規のピラゾロピリミジン - Google Patents
新規のピラゾロピリミジン Download PDFInfo
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- JP5334414B2 JP5334414B2 JP2007528889A JP2007528889A JP5334414B2 JP 5334414 B2 JP5334414 B2 JP 5334414B2 JP 2007528889 A JP2007528889 A JP 2007528889A JP 2007528889 A JP2007528889 A JP 2007528889A JP 5334414 B2 JP5334414 B2 JP 5334414B2
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- JP
- Japan
- Prior art keywords
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- phenyl
- biphen
- alkyl
- substituted
- 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.)
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- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 407
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 89
- 201000010099 disease Diseases 0.000 claims abstract description 69
- 230000002062 proliferating effect Effects 0.000 claims abstract description 16
- -1 nitro, hydroxyl Chemical group 0.000 claims description 567
- 229910052739 hydrogen Inorganic materials 0.000 claims description 120
- 239000001257 hydrogen Substances 0.000 claims description 117
- 206010028980 Neoplasm Diseases 0.000 claims description 112
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 101
- 229910052757 nitrogen Inorganic materials 0.000 claims description 81
- 201000011510 cancer Diseases 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000005842 heteroatom Chemical group 0.000 claims description 71
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 64
- 239000002246 antineoplastic agent Substances 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 55
- 229910052717 sulfur Inorganic materials 0.000 claims description 55
- 239000011593 sulfur Substances 0.000 claims description 55
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 54
- 229910052760 oxygen Inorganic materials 0.000 claims description 54
- 239000001301 oxygen Substances 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 47
- 238000011282 treatment Methods 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000002950 monocyclic group Chemical group 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 28
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Chemical group 0.000 claims description 20
- 125000002541 furyl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 18
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 230000003211 malignant effect Effects 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 16
- 206010060999 Benign neoplasm Diseases 0.000 claims description 14
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Chemical group 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 9
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 9
- 239000000556 agonist Substances 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 9
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- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 7
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 7
- 229960002584 gefitinib Drugs 0.000 claims description 7
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229960003787 sorafenib Drugs 0.000 claims description 7
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 6
- 102000001708 Protein Isoforms Human genes 0.000 claims description 6
- 108010029485 Protein Isoforms Proteins 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 6
- 229960004316 cisplatin Drugs 0.000 claims description 6
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 6
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 6
- 229960001433 erlotinib Drugs 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 229940043355 kinase inhibitor Drugs 0.000 claims description 6
- IXWNTLSTOZFSCM-YVACAVLKSA-N ombrabulin Chemical compound C1=C(NC(=O)[C@@H](N)CO)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 IXWNTLSTOZFSCM-YVACAVLKSA-N 0.000 claims description 6
- 229950003600 ombrabulin Drugs 0.000 claims description 6
- 229930002330 retinoic acid Natural products 0.000 claims description 6
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 claims description 6
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 6
- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 6
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims description 6
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- 239000004066 vascular targeting agent Substances 0.000 claims description 6
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 5
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 5
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 5
- 102000009058 Death Domain Receptors Human genes 0.000 claims description 5
- 108010049207 Death Domain Receptors Proteins 0.000 claims description 5
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 5
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
- 229960001467 bortezomib Drugs 0.000 claims description 5
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical group C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 5
- 229940127093 camptothecin Drugs 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 5
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 5
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- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 5
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- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 5
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- MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical group O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 claims description 5
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- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP04104283 | 2004-09-06 | ||
| EP04104283.9 | 2004-09-06 | ||
| PCT/EP2005/054366 WO2006027346A2 (en) | 2004-09-06 | 2005-09-05 | Novel pyrazolopyrimidines |
Publications (3)
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| JP2008512359A JP2008512359A (ja) | 2008-04-24 |
| JP2008512359A5 JP2008512359A5 (enExample) | 2013-06-06 |
| JP5334414B2 true JP5334414B2 (ja) | 2013-11-06 |
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| JP2007528889A Expired - Fee Related JP5334414B2 (ja) | 2004-09-06 | 2005-09-05 | 新規のピラゾロピリミジン |
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| Country | Link |
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| US (1) | US7745446B2 (enExample) |
| EP (1) | EP1797096B1 (enExample) |
| JP (1) | JP5334414B2 (enExample) |
| AT (1) | ATE517901T1 (enExample) |
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| CA (1) | CA2578384A1 (enExample) |
| ES (1) | ES2368930T3 (enExample) |
| WO (1) | WO2006027346A2 (enExample) |
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| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ATE556713T1 (de) | 1999-01-13 | 2012-05-15 | Bayer Healthcare Llc | Omega-carboxyarylsubstituierte-diphenyl- harnstoffe als p38-kinasehemmer |
| AU2003209116A1 (en) | 2002-02-11 | 2003-09-04 | Bayer Pharmaceuticals Corporation | Aryl ureas with angiogenesis inhibiting activity |
| PT1636585E (pt) | 2003-05-20 | 2008-03-27 | Bayer Pharmaceuticals Corp | Diarilureias com actividade inibidora de cinase |
| NZ544920A (en) | 2003-07-23 | 2009-11-27 | Bayer Healthcare Llc | 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide and metabolites for the treatment and prevention of diseases and conditions |
| CA2609387A1 (en) * | 2005-05-27 | 2006-11-30 | Bayer Healthcare Ag | Combination therapy comprising diaryl ureas for treating diseases |
| CA2642813A1 (en) | 2006-02-28 | 2007-09-07 | Merck & Co., Inc. | Inhibitors of histone deacetylase |
| EP2012801A4 (en) | 2006-04-24 | 2009-08-05 | Gloucester Pharmaceuticals Inc | GEMCITABINE COMBINATION THERAPY |
| WO2007146730A2 (en) | 2006-06-08 | 2007-12-21 | Gloucester Pharmaceuticals | Deacetylase inhibitor therapy |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| EP2359825A2 (en) * | 2006-10-06 | 2011-08-24 | Takeda Pharmaceutical Company Limited | Combination drug |
| MX2009006969A (es) | 2006-12-29 | 2010-04-07 | Gloucester Pharmaceuticals | Purificacion de romidepsina. |
| WO2009002495A1 (en) | 2007-06-27 | 2008-12-31 | Merck & Co., Inc. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| US8461189B2 (en) | 2007-06-27 | 2013-06-11 | Merck Sharp & Dohme Corp. | Pyridyl derivatives as histone deacetylase inhibitors |
| US20100135983A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Anti-inflammatory compositions and methods |
| US20100136095A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| US20100137246A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Anti-inflammatory compositions and methods |
| US20100136097A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| US20100136094A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| US20100137843A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Delivery devices for modulating inflammation |
| US20100136096A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| AU2010339444A1 (en) * | 2009-12-30 | 2012-07-19 | Arqule, Inc. | Substituted pyrrolo-aminopyrimidine compounds |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| US20130131057A1 (en) | 2010-05-13 | 2013-05-23 | Centro Nacional De Investigaciones Oncologicas (Cnio | New bicyclic compounds as pi3-k and mtor inhibitors |
| UA114074C2 (xx) | 2010-07-12 | 2017-04-25 | Кристалічна форма с ромідепсину та її застосування для лікування шкірної т-клітинної лімфоми або периферичної т-клітинної лімфоми | |
| US8859502B2 (en) | 2010-09-13 | 2014-10-14 | Celgene Corporation | Therapy for MLL-rearranged leukemia |
| BR112014026706A2 (pt) * | 2012-04-24 | 2017-06-27 | Glaxosmithkline Ip No 2 Ltd | método de tratamento para dermatoses responsivas a esteroides |
| AU2013202506B2 (en) | 2012-09-07 | 2015-06-18 | Celgene Corporation | Resistance biomarkers for hdac inhibitors |
| AU2013202507B9 (en) | 2012-11-14 | 2015-08-13 | Celgene Corporation | Inhibition of drug resistant cancer cells |
| KR20160099081A (ko) | 2013-07-26 | 2016-08-19 | 업데이트 파마 인코포레이트 | 비산트렌의 치료 효과 개선용 조합 방법 |
| NZ630311A (en) | 2013-12-27 | 2016-03-31 | Celgene Corp | Romidepsin formulations and uses thereof |
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| US5859205A (en) | 1989-12-21 | 1999-01-12 | Celltech Limited | Humanised antibodies |
| DE59109269D1 (de) | 1990-06-28 | 2005-12-15 | Hoechst Ag | Fusionsproteine mit Immunglobulinanteilen, ihre Herstellung und Verwendung |
| CA2154681A1 (en) | 1993-02-03 | 1994-08-18 | Mark David Erion | Adenosine kinase inhibitors comprising lyxofuranosyl derivatives |
| US6235741B1 (en) * | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| US6245759B1 (en) | 1999-03-11 | 2001-06-12 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| WO2002083675A2 (en) | 2001-04-10 | 2002-10-24 | Merck Sharp & Dohme Limited | Inhibitors of akt activity |
| AU2002341920A1 (en) | 2001-10-02 | 2003-04-14 | Smithkline Beecham Corporation | Chemical compounds |
| PL369742A1 (en) | 2001-10-15 | 2005-05-02 | Gpc Biotech Inc. | Inhibitors of cyclin-dependent kinases, compositions and uses related thereto |
| US20030199525A1 (en) | 2002-03-21 | 2003-10-23 | Hirst Gavin C. | Kinase inhibitors |
| US20030180924A1 (en) | 2002-03-22 | 2003-09-25 | Desimone Robert W. | Formulation of certain pyrazolo [3,4,-d] pyrimidines as kinase modulators |
| DE60237425D1 (de) | 2002-03-28 | 2010-10-07 | Univerzita Palackeho V Olomouc | PyrazoloÄ4,3-dÜpyrimidine, Verfahren zu ihrer Herstellung und therapeutische Anwendung |
| TW200400034A (en) | 2002-05-20 | 2004-01-01 | Bristol Myers Squibb Co | Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors |
| US7181868B2 (en) | 2002-06-26 | 2007-02-27 | Nike, Incorporated | Article of footwear having a sole with a flex control member |
| EP1534389A2 (en) | 2002-07-23 | 2005-06-01 | SmithKline Beecham Corporation | Pyrazolopyrimidines as kinase inhibitors |
| EP1523314A2 (en) | 2002-07-23 | 2005-04-20 | SmithKline Beecham Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| WO2004009602A1 (en) | 2002-07-23 | 2004-01-29 | Smithkline Beecham Corporation | Pyrazolopyrimidines as kinase inhibitors |
| EP1537116B1 (en) | 2002-09-04 | 2010-06-02 | Schering Corporation | Pyrazolopyrimidines suitable for the treatment of cancer diseases |
| DE60313872T2 (de) * | 2002-09-04 | 2008-01-17 | Schering Corp. | Pyrazoloä1,5-aüpyrimidine als hemmstoffe cyclin-abhängiger kinasen |
| AU2003268385B2 (en) | 2002-09-04 | 2006-12-21 | Pharmacopeia, Inc. | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| WO2004022062A1 (en) | 2002-09-04 | 2004-03-18 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| WO2004030671A2 (en) | 2002-10-02 | 2004-04-15 | Merck Patent Gmbh | Use of 4-amino-quinazolines as anti cancer agents |
| WO2004063195A1 (en) | 2003-01-03 | 2004-07-29 | Sloan-Kettering Institute For Cancer Research | Pyridopyrimidine kinase inhibitors |
| EP1608652A1 (en) * | 2003-03-31 | 2005-12-28 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
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2005
- 2005-09-05 CA CA002578384A patent/CA2578384A1/en not_active Abandoned
- 2005-09-05 AU AU2005281704A patent/AU2005281704A1/en not_active Abandoned
- 2005-09-05 US US11/661,111 patent/US7745446B2/en not_active Expired - Fee Related
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- 2005-09-05 WO PCT/EP2005/054366 patent/WO2006027346A2/en not_active Ceased
- 2005-09-05 ES ES05786968T patent/ES2368930T3/es not_active Expired - Lifetime
- 2005-09-05 JP JP2007528889A patent/JP5334414B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
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| EP1797096A2 (en) | 2007-06-20 |
| EP1797096B1 (en) | 2011-07-27 |
| ES2368930T3 (es) | 2011-11-23 |
| WO2006027346A2 (en) | 2006-03-16 |
| WO2006027346A3 (en) | 2006-08-03 |
| CA2578384A1 (en) | 2006-03-16 |
| ATE517901T1 (de) | 2011-08-15 |
| AU2005281704A1 (en) | 2006-03-16 |
| US20070254046A1 (en) | 2007-11-01 |
| US7745446B2 (en) | 2010-06-29 |
| JP2008512359A (ja) | 2008-04-24 |
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