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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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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- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- 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)
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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 |
Country Status (8)
| Country | Link |
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| US (1) | US7745446B2 (enExample) |
| EP (1) | EP1797096B1 (enExample) |
| JP (1) | JP5334414B2 (enExample) |
| AT (1) | ATE517901T1 (enExample) |
| AU (1) | AU2005281704A1 (enExample) |
| 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 |
| EP2298311B1 (en) | 1999-01-13 | 2012-05-09 | Bayer HealthCare LLC | w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| DK1478358T3 (da) | 2002-02-11 | 2013-10-07 | Bayer Healthcare Llc | Sorafenibtosylat til behandling af sygdomme kendetegnet ved unormal angiogenese |
| EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
| PL1663978T3 (pl) | 2003-07-23 | 2008-04-30 | Bayer Healthcare Llc | Fluoropodstawiony omega-karboksyarylodifenylomocznik do leczenia i profilaktyki chorób i stanów |
| JP2008545670A (ja) * | 2005-05-27 | 2008-12-18 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 疾患を処置するためのジアリールウレア類を含む組合せ治療 |
| US8168658B2 (en) | 2006-02-28 | 2012-05-01 | Merck Sharp & Dohme Corp. | Inhibitors of histone deacetylase |
| US9539303B2 (en) | 2006-04-24 | 2017-01-10 | Celgene Corporation | Treatment of Ras-expressing tumors |
| US8957027B2 (en) | 2006-06-08 | 2015-02-17 | Celgene Corporation | Deacetylase inhibitor therapy |
| DE602007011628D1 (de) | 2006-07-06 | 2011-02-10 | Array Biopharma Inc | Dihydrofuropyrimidine als akt-proteinkinaseinhibitoren |
| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| AU2007307489A1 (en) * | 2006-10-06 | 2008-04-17 | Takeda Pharmaceutical Company Limited | Combination drug |
| EP2102230A2 (en) | 2006-12-29 | 2009-09-23 | Gloucester Pharmaceuticals, Inc. | Purifiction of romidepsin |
| JP2010531358A (ja) | 2007-06-27 | 2010-09-24 | メルク・シャープ・エンド・ドーム・コーポレイション | ヒストン脱アセチル化酵素阻害剤としてのピリジル及びピリミジニル誘導体 |
| WO2009002495A1 (en) | 2007-06-27 | 2008-12-31 | Merck & Co., Inc. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| US20100136097A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| US20100135908A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Delivery devices for modulating inflammation |
| US20100135983A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Anti-inflammatory compositions and methods |
| US20100136096A1 (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 |
| 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 |
| KR20120124428A (ko) * | 2009-12-30 | 2012-11-13 | 아르퀼 인코포레이티드 | 치환된 피롤로-아미노피리미딘 화합물 |
| 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 |
| CN103108648A (zh) | 2010-07-12 | 2013-05-15 | 细胞基因公司 | 罗米地辛固体形式及其用途 |
| US8859502B2 (en) | 2010-09-13 | 2014-10-14 | Celgene Corporation | Therapy for MLL-rearranged leukemia |
| UA113875C2 (uk) * | 2012-04-24 | 2017-03-27 | Новартіс Аг | Спосіб лікування стероїдзалежних дерматозів |
| 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 |
| AU2014293013A1 (en) | 2013-07-26 | 2016-03-17 | Race Oncology Ltd. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| 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 |
| EP0464533B1 (de) | 1990-06-28 | 1998-07-29 | Hoechst Aktiengesellschaft | Fusionsproteine mit immunglobulinanteilen, ihre Herstellung und Verwendung |
| WO1994018215A1 (en) | 1993-02-03 | 1994-08-18 | Gensia, Inc. | 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 |
| WO2003033499A2 (en) | 2001-10-15 | 2003-04-24 | Gpc Biotech Inc. | Inhibitors of cyclin-dependent kinases, compositions and uses related thereto |
| US6960584B2 (en) | 2001-04-10 | 2005-11-01 | Merck & Co., Inc. | Inhibitors of Akt activity |
| US7217710B2 (en) | 2001-10-02 | 2007-05-15 | Smithkline Beecham Corporation | Substituted pyrazolopyrimidines |
| US20030199525A1 (en) | 2002-03-21 | 2003-10-23 | Hirst Gavin C. | Kinase inhibitors |
| AU2003225933A1 (en) | 2002-03-22 | 2003-10-13 | Cellular Genomics, Inc. | AN IMPROVED FORMULATION OF CERTAIN PYRAZOLO(3,4-d) PYRIMIDINES AS KINASE MODULATORS |
| ATE478872T1 (de) | 2002-03-28 | 2010-09-15 | Ustav Ex Botan Av Cr V V I I O | 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 |
| WO2004009597A2 (en) | 2002-07-23 | 2004-01-29 | Smithkline Beecham Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| EP1534389A2 (en) | 2002-07-23 | 2005-06-01 | SmithKline Beecham Corporation | Pyrazolopyrimidines as kinase inhibitors |
| JP2005536517A (ja) | 2002-07-23 | 2005-12-02 | スミスクライン ビーチャム コーポレーション | キナーゼインヒビターとしてのピラゾロピリミジン |
| EP1545533A1 (en) | 2002-09-04 | 2005-06-29 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| JP4881558B2 (ja) | 2002-09-04 | 2012-02-22 | シェーリング コーポレイション | サイクリン依存性キナーゼインヒビターとしてのピラゾロピリミジン |
| KR20050057139A (ko) | 2002-09-04 | 2005-06-16 | 쉐링 코포레이션 | 사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘 |
| DE60313872T2 (de) | 2002-09-04 | 2008-01-17 | Schering Corp. | Pyrazoloä1,5-aüpyrimidine als hemmstoffe cyclin-abhängiger kinasen |
| 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 |
| WO2004087707A1 (en) * | 2003-03-31 | 2004-10-14 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
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2005
- 2005-09-05 JP JP2007528889A patent/JP5334414B2/ja not_active Expired - Fee Related
- 2005-09-05 WO PCT/EP2005/054366 patent/WO2006027346A2/en not_active Ceased
- 2005-09-05 AT AT05786968T patent/ATE517901T1/de not_active IP Right Cessation
- 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
- 2005-09-05 EP EP05786968A patent/EP1797096B1/en not_active Expired - Lifetime
- 2005-09-05 ES ES05786968T patent/ES2368930T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006027346A3 (en) | 2006-08-03 |
| WO2006027346A2 (en) | 2006-03-16 |
| CA2578384A1 (en) | 2006-03-16 |
| JP2008512359A (ja) | 2008-04-24 |
| US7745446B2 (en) | 2010-06-29 |
| EP1797096A2 (en) | 2007-06-20 |
| EP1797096B1 (en) | 2011-07-27 |
| ATE517901T1 (de) | 2011-08-15 |
| ES2368930T3 (es) | 2011-11-23 |
| US20070254046A1 (en) | 2007-11-01 |
| AU2005281704A1 (en) | 2006-03-16 |
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