CA2502429A1 - Antiinflammation agents - Google Patents
Antiinflammation agents Download PDFInfo
- Publication number
- CA2502429A1 CA2502429A1 CA002502429A CA2502429A CA2502429A1 CA 2502429 A1 CA2502429 A1 CA 2502429A1 CA 002502429 A CA002502429 A CA 002502429A CA 2502429 A CA2502429 A CA 2502429A CA 2502429 A1 CA2502429 A1 CA 2502429A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- aryl
- heteroaryl
- compound
- 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
- 239000002260 anti-inflammatory agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
- 201000010099 disease Diseases 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000015181 infectious disease Diseases 0.000 claims abstract description 11
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 11
- 230000002503 metabolic effect Effects 0.000 claims abstract description 9
- 230000002458 infectious effect Effects 0.000 claims abstract description 8
- 230000002062 proliferating effect Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 235
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 109
- -1 tetrahydrobenzofuryl Chemical group 0.000 claims description 104
- 125000001072 heteroaryl group Chemical group 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 79
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 239000000651 prodrug Substances 0.000 claims description 18
- 102000000589 Interleukin-1 Human genes 0.000 claims description 16
- 108010002352 Interleukin-1 Proteins 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 108010050904 Interferons Proteins 0.000 claims description 9
- 102000014150 Interferons Human genes 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229940079322 interferon Drugs 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 6
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 239000003246 corticosteroid Substances 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000004927 fusion Effects 0.000 claims description 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 6
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
- 108010036949 Cyclosporine Proteins 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 5
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims description 5
- 229960001967 tacrolimus Drugs 0.000 claims description 5
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 108010008165 Etanercept Proteins 0.000 claims description 4
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims description 4
- 239000003472 antidiabetic agent Substances 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 229960002170 azathioprine Drugs 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229960004397 cyclophosphamide Drugs 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000026278 immune system disease Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 229960002930 sirolimus Drugs 0.000 claims description 4
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 4
- XHVAWZZCDCWGBK-WYRLRVFGSA-M Aurothioglucose Chemical compound OC[C@H]1O[C@H](S[Au])[C@H](O)[C@@H](O)[C@@H]1O XHVAWZZCDCWGBK-WYRLRVFGSA-M 0.000 claims description 3
- 229930105110 Cyclosporin A Natural products 0.000 claims description 3
- 108010072051 Glatiramer Acetate Proteins 0.000 claims description 3
- 102000019223 Interleukin-1 receptor Human genes 0.000 claims description 3
- 108050006617 Interleukin-1 receptor Proteins 0.000 claims description 3
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims description 3
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- FHEAIOHRHQGZPC-KIWGSFCNSA-N acetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FHEAIOHRHQGZPC-KIWGSFCNSA-N 0.000 claims description 3
- 229960001799 aurothioglucose Drugs 0.000 claims description 3
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- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
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- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 3
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- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 claims description 2
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- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 claims description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
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- Rheumatology (AREA)
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- Oncology (AREA)
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- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Pain & Pain Management (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42253102P | 2002-10-31 | 2002-10-31 | |
| US60/422,531 | 2002-10-31 | ||
| PCT/US2003/029143 WO2004041285A1 (en) | 2002-10-31 | 2003-09-19 | Antiinflammation agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2502429A1 true CA2502429A1 (en) | 2004-05-21 |
Family
ID=32312522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002502429A Abandoned CA2502429A1 (en) | 2002-10-31 | 2003-09-19 | Antiinflammation agents |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7199119B2 (https=) |
| EP (1) | EP1556053A4 (https=) |
| JP (1) | JP2006512313A (https=) |
| AU (1) | AU2003270701B2 (https=) |
| CA (1) | CA2502429A1 (https=) |
| WO (1) | WO2004041285A1 (https=) |
Families Citing this family (122)
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| US20030220646A1 (en) * | 2002-05-23 | 2003-11-27 | Thelen Sarah L. | Method and apparatus for reducing femoral fractures |
| US7112676B2 (en) * | 2002-11-04 | 2006-09-26 | Hoffmann-La Roche Inc. | Pyrimido compounds having antiproliferative activity |
| UA82358C2 (uk) * | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
| JP2006522756A (ja) * | 2003-04-10 | 2006-10-05 | エフ．ホフマン−ラ ロシュ アーゲー | ピリミド化合物 |
| DE10323345A1 (de) * | 2003-05-23 | 2004-12-16 | Zentaris Gmbh | Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren |
| GB0315950D0 (en) * | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| BRPI0413558A (pt) | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| MXPA06002199A (es) | 2003-08-27 | 2006-05-22 | 3M Innovative Properties Co | Imidazoquinolinas sustituidas con grupos ariloxi o arilalquilenoxi. |
| CA2537763A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| CA2540541C (en) | 2003-10-03 | 2012-03-27 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| TW200526656A (en) | 2003-10-03 | 2005-08-16 | 3M Innovative Properties Co | Pyrazolopyridines and analogs thereof |
| US7897767B2 (en) | 2003-11-14 | 2011-03-01 | 3M Innovative Properties Company | Oxime substituted imidazoquinolines |
| WO2005048945A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| WO2005051317A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| JP2007517035A (ja) | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| DE102004005172A1 (de) * | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
| WO2005094531A2 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US20050256154A1 (en) * | 2004-05-04 | 2005-11-17 | Kin-Chun Luk | 4-Amino-thieno[3,2-c]pyridine-7-carboxylic acid amides |
| KR100822681B1 (ko) * | 2004-05-04 | 2008-04-17 | 에프. 호프만-라 로슈 아게 | Ｉｋｋ 억제제로서의 티에노피리다진 |
| KR100796965B1 (ko) * | 2004-05-04 | 2008-01-22 | 에프. 호프만-라 로슈 아게 | Ｉｋｋ 저해제로서의 티에노피리딘 |
| EP1753428A4 (en) * | 2004-05-14 | 2010-09-15 | Abbott Lab | INHIBITORS OF KINASES AS THERAPEUTIC AGENTS |
| WO2005117860A1 (en) * | 2004-06-03 | 2005-12-15 | Asmacure Ltée | Method of treating and preventing arthritis, cutaneous and cardiovascular inflammatory-related diseases using nicotinic receptor agonists |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| JP4675586B2 (ja) * | 2004-06-23 | 2011-04-27 | 壽製薬株式会社 | 高血圧症及び血清高尿酸血症の重複発症の治療のための薬剤 |
| US7576212B2 (en) * | 2004-12-09 | 2009-08-18 | Xention Limited | Thieno[2,3-B] pyridines as potassium channel inhibitors |
| AU2005326708C1 (en) | 2004-12-30 | 2012-08-30 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| JP5543068B2 (ja) | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| CA2597587A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| JP2008538550A (ja) | 2005-04-01 | 2008-10-30 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物 |
| JP2008535832A (ja) | 2005-04-01 | 2008-09-04 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ピラゾロピリジン−１，４−ジアミン、およびそのアナログ |
| JP2009502996A (ja) * | 2005-08-04 | 2009-01-29 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | ＩＫＫ−β阻害剤との組合せ |
| JP2009504692A (ja) * | 2005-08-16 | 2009-02-05 | エフ．ホフマン−ラ ロシュ アーゲー | 新規４−アミノ−チエノ［３，２−ｃ］ピリジン−７−カルボン酸アミド |
| CA2621830C (en) * | 2005-09-15 | 2013-12-03 | F. Hoffmann-La Roche Ag | 4-amino-thieno[3,2-c]pyridine-7-carboxylic acid derivatives |
| ATE553108T1 (de) * | 2005-11-08 | 2012-04-15 | Hoffmann La Roche | Thiazoloä4,5-cüpyridinderivative als antagonisten des mglu5-rezeptors |
| GB0525164D0 (en) * | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| US7465795B2 (en) * | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| AU2006327300A1 (en) * | 2005-12-20 | 2007-06-28 | Astrazeneca Ab | Substituted Cinnoline derivatives as GABAa-receptor modulators and method for their synthesis |
| KR100846988B1 (ko) * | 2006-03-06 | 2008-07-16 | 제일약품주식회사 | 신규한 티에노피리미딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 함유하는 약학조성물 |
| EP2038289A2 (en) | 2006-04-21 | 2009-03-25 | Amgen Inc. | Thieno-[2,3-d]pyrimidine and thieno-pyridazine compounds and methods of use |
| US7537063B2 (en) * | 2006-06-26 | 2009-05-26 | Cindi Michelle La Croix | Thrush and white line medicinal delivery system |
| US7932390B2 (en) * | 2006-06-29 | 2011-04-26 | Hoffman-La Roche Inc. | Substituted thieno[3,2-C]pyridine carboxylic acid derivatives |
| US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| US7968556B2 (en) * | 2006-10-19 | 2011-06-28 | Signal Pharmaceuticals, Llc | Heteroaryl compounds, compositions thereof, and methods of treatment therewith |
| US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
| US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8998846B2 (en) | 2006-11-20 | 2015-04-07 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
| US8414909B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| AR067028A1 (es) * | 2007-06-19 | 2009-09-30 | Astrazeneca Ab | Compuestos y usos de los mismos 849 |
| RU2327486C1 (ru) * | 2007-07-04 | 2008-06-27 | Валентина Васильевна Малиновская | Лекарственное средство для лечения инфекционно-воспалительных заболеваний, обладающее иммуномодулирующим, антивирусным, антибактериальным, антиоксидантным, мембраностабилизирующим, противовоспалительным, антитоксическим свойствами |
| MX2010001636A (es) * | 2007-08-14 | 2010-03-15 | Hoffmann La Roche | Derivados de pirazolo[3,4-d]-pirimidina como agentes antiproliferativos. |
| CN102177157A (zh) * | 2008-08-12 | 2011-09-07 | 西特里斯药业公司 | 作为沉默调节蛋白调节剂的苯并*唑类、苯并噻唑类和相关的类似物 |
| CN102271515B (zh) | 2008-10-31 | 2014-07-02 | 健泰科生物技术公司 | 吡唑并嘧啶jak抑制剂化合物和方法 |
| EP2243481A1 (en) | 2009-04-24 | 2010-10-27 | PamGene B.V. | Irak kinase family as novel drug target for Alzheimer |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| DE102009033208A1 (de) | 2009-07-15 | 2011-01-20 | Merck Patent Gmbh | Aminopyridinderivate |
| ES2587509T3 (es) * | 2009-09-18 | 2016-10-25 | Zhanggui Wu | Derivados de tieno[2,3-d]piridazina y uso terapéutico de los mismos para la inhibición de proteína cinasa |
| MY177695A (en) | 2009-10-26 | 2020-09-23 | Signal Pharm Llc | Methods of synthesis and purification of heteroaryl compounds |
| WO2011056561A1 (en) | 2009-10-27 | 2011-05-12 | Beth Israel Deaconess Medical Center | Methods and compositions for the generation and use of conformation-specific antibodies |
| JO3437B1 (ar) | 2009-10-30 | 2019-10-20 | Esai R & D Man Co Ltd | أجسام مضادة محسنة مضادة للفراكتالكين البشري واستخداماتها |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| WO2011100502A1 (en) | 2010-02-11 | 2011-08-18 | OSI Pharmaceuticals, LLC | 7-aminofuropyridine derivatives |
| CA2793024A1 (en) * | 2010-03-17 | 2011-09-22 | F. Hoffmann-La Roche Ag | Imidazopyridine compounds, compositions and methods of use |
| AU2011281015B2 (en) | 2010-07-23 | 2015-09-24 | President And Fellows Of Harvard College | Tricyclic proteasome activity enhancing compounds |
| MX2013003019A (es) | 2010-09-15 | 2013-05-28 | Hoffmann La Roche | Compuestos de azabenzotiazol, composiciones y metodos de uso. |
| MX2013005445A (es) | 2010-11-19 | 2013-07-29 | Hoffmann La Roche | Pirazolopiridinas y el uso de pirazolopiridinas como inhibidores de tirosina cinasa 2 (tyk2). |
| US8703941B2 (en) | 2011-01-10 | 2014-04-22 | Nimbus Iris, Inc. | IRAK inhibitors and uses thereof |
| WO2012149334A2 (en) | 2011-04-27 | 2012-11-01 | Beth Israel Deaconess Medical Center, Inc. | Methods and compositions for the generation and use of conformation-specific antibodies |
| KR101978537B1 (ko) | 2011-10-19 | 2019-05-14 | 시그날 파마소티칼 엘엘씨 | Tor 키나제 억제제를 사용한 암의 치료 |
| JP6076370B2 (ja) | 2011-12-02 | 2017-02-08 | シグナル ファーマシューティカルズ，エルエルシー | ７−（６−（２−ヒドロキシプロパン−２−イル）ピリジン−３−イル）−１−（（トランス）−４−メトキシシクロヘキシル）−３，４−ジヒドロピラジノ［２，３−ｂ］ピラジン−２（１Ｈ）−オンの薬剤組成物、その固体形態、およびその使用方法 |
| CN104582705A (zh) * | 2012-01-10 | 2015-04-29 | 林伯士艾瑞斯公司 | 白介素-1受体相关激酶(irak)抑制剂和其用途 |
| CA2861464C (en) * | 2012-01-25 | 2018-03-06 | Proteostasis Therapeutics, Inc. | Proteasome activity modulating tricyclic compounds |
| TWI615143B (zh) | 2012-02-24 | 2018-02-21 | 標誌製藥公司 | 使用ｔｏｒ激酶抑制劑組合療法以治療癌症之方法 |
| US9206221B2 (en) * | 2012-04-06 | 2015-12-08 | Wisconsin Alumni Research Foundation | Amphiphilic compounds |
| HK1210696A1 (en) | 2012-07-11 | 2016-05-06 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| WO2014011906A2 (en) | 2012-07-11 | 2014-01-16 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| AU2013203714B2 (en) | 2012-10-18 | 2015-12-03 | Signal Pharmaceuticals, Llc | Inhibition of phosphorylation of PRAS40, GSK3-beta or P70S6K1 as a marker for TOR kinase inhibitory activity |
| EP2914296B2 (en) | 2012-11-01 | 2021-09-29 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| JP2016505012A (ja) | 2013-01-10 | 2016-02-18 | ニンバス アイリス， インコーポレイテッド | Ｉｒａｋ阻害剤およびその使用 |
| EP2945636B1 (en) | 2013-01-16 | 2017-06-28 | Signal Pharmaceuticals, LLC | Substituted pyrrolopyrimidine compounds, compositions thereof, and methods of treatment therewith |
| US8778365B1 (en) | 2013-01-31 | 2014-07-15 | Merz Pharmaceuticals, Llc | Topical compositions and methods for making and using same |
| US20160024051A1 (en) | 2013-03-15 | 2016-01-28 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| BR112015026292B1 (pt) | 2013-04-17 | 2022-04-12 | Signal Pharmaceuticals, Llc | Uso de 1-etil-7-(2-metil-6-(1h-1,2,4-triazol-3-il)piridin-3-il)-3,4-dihidropirazino [2,3-b]pirazin-2(1h)- ona e métodos in vitro |
| US9937169B2 (en) | 2013-04-17 | 2018-04-10 | Signal Pharmaceuticals, Llc | Methods for treating cancer using dihydropyrazino-pyrazine compound combination therapy |
| BR112015026297B1 (pt) | 2013-04-17 | 2022-08-23 | Signal Pharmaceuticals, Llc | Uso de um inibidor da quinase tor e quinazolinona 5-substituída, composição farmacêutica que os compreende, e kit |
| TW201527300A (zh) | 2013-04-17 | 2015-07-16 | Signal Pharm Llc | 關於１－乙基－７－（２－甲基－６－（１Ｈ－１，２，４－三唑－３－基）吡啶－３－基）－３，４－二氫吡并［２，３－ｂ］吡－２（１Ｈ）－酮之醫藥調配物、方法、固態型式及使用方法 |
| AU2014254052B2 (en) | 2013-04-17 | 2019-06-06 | Signal Pharmaceuticals, Llc | Treatment of cancer with dihydropyrazino-pyrazines |
| US9782427B2 (en) | 2013-04-17 | 2017-10-10 | Signal Pharmaceuticals, Llc | Methods for treating cancer using TOR kinase inhibitor combination therapy |
| TW201521725A (zh) | 2013-04-17 | 2015-06-16 | Signal Pharm Llc | 使用ｔｏｒ激酶抑制劑組合療法以治療癌症之方法 |
| EP3003313A1 (en) | 2013-05-29 | 2016-04-13 | Signal Pharmaceuticals, LLC | Pharmaceutical compositions of 7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-1-((trans)-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one, a solid form thereof and methods of their use |
| SG11201509842SA (en) | 2013-05-30 | 2015-12-30 | Infinity Pharmaceuticals Inc | Treatment of cancers using pi3 kinase isoform modulators |
| JP6509838B2 (ja) * | 2013-06-26 | 2019-05-08 | アッヴィ・インコーポレイテッド | Ｂｔｋ阻害薬としての一級カルボキサミド類 |
| BR112016006319A2 (pt) | 2013-09-27 | 2017-08-01 | Nimbus Iris Inc | inibidores de irak e usos dos mesmos |
| UA115388C2 (uk) | 2013-11-21 | 2017-10-25 | Пфайзер Інк. | 2,6-заміщені пуринові похідні та їх застосування в лікуванні проліферативних захворювань |
| EP3131552B1 (en) | 2014-04-16 | 2020-07-15 | Signal Pharmaceuticals, LLC | Methods for treating cancer using tor kinase inhibitor combination therapy |
| US9718824B2 (en) | 2014-04-16 | 2017-08-01 | Signal Pharmaceuticals, Llc | Solid forms comprising 7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-1-((trans)-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, and a coformer, compositions and methods of use thereof |
| US9512129B2 (en) | 2014-04-16 | 2016-12-06 | Signal Pharmaceuticals, Llc | Solid forms comprising 1-ethyl-7-(2-methyl-6-(1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one and a coformer |
| NZ714742A (en) | 2014-04-16 | 2017-04-28 | Signal Pharm Llc | Solid forms of 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one, compositions thereof and methods of their use |
| PE20211782A1 (es) | 2014-05-23 | 2021-09-08 | Hoffmann La Roche | Compuestos de 5-cloro-2-difluorometoxifenil pirazolopirimidina, composiciones y metodos de uso de los mismos |
| NZ629796A (en) | 2014-07-14 | 2015-12-24 | Signal Pharm Llc | Amorphous form of 4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-n-methylbenzamide, compositions thereof and methods of their use |
| EA201790189A1 (ru) | 2014-07-14 | 2017-11-30 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Способы лечения злокачественного новообразования с использованием замещенных пирролопиримидиновых соединений, композиции на их основе |
| WO2016126726A1 (en) | 2015-02-02 | 2016-08-11 | Forma Therapeutics, Inc. | Bicyclic [4,6,0] hydroxamic acids as hdac6 inhibitors |
| SG11201708622UA (en) | 2015-02-02 | 2017-11-29 | Forma Therapeutics Inc | 3-aryl-4-amido-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors |
| EP3472131B1 (en) | 2016-06-17 | 2020-02-19 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as hdac inhibitors |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| HUE071047T2 (hu) | 2016-08-31 | 2025-07-28 | Mapi Pharma Ltd | Glatiramer-acetátot tartalmazó depórendszerek |
| EP3541817B1 (en) * | 2016-11-17 | 2020-12-23 | Bristol-Myers Squibb Company | Imidazopyridazine modulators of il-12, il-23 and/or ifn-alpha |
| CN110382052A (zh) | 2017-03-26 | 2019-10-25 | Mapi医药公司 | 用于治疗进展型形式的多发性硬化症的格拉替雷储库系统 |
| WO2018215389A1 (en) | 2017-05-22 | 2018-11-29 | F. Hoffmann-La Roche Ag | Therapeutic compounds and compositions, and methods of use thereof |
| EP3641772B1 (en) | 2017-06-22 | 2023-08-02 | Celgene Corporation | Treatment of hepatocellular carcinoma characterized by hepatitis b virus infection |
| CN109402240B (zh) * | 2019-01-08 | 2020-08-25 | 圣湘生物科技股份有限公司 | 核酸释放剂、核酸pcr扩增方法和pcr扩增试剂盒 |
| US12605387B2 (en) | 2020-07-24 | 2026-04-21 | Secura Bio, Inc. | Treatment of cancers using PI3 kinase isoform modulators |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3663559A (en) * | 1969-12-03 | 1972-05-16 | Union Carbide Corp | Preparation of oxo-furo-pyridines from furylvinyl isocyanates |
| US3845065A (en) * | 1972-02-18 | 1974-10-29 | Merck & Co Inc | 4-oxo-4,5-dihydrothieno(3,2-c)pyridines |
| US3903095A (en) * | 1972-02-18 | 1975-09-02 | Merck & Co Inc | Certain substituted-thieno{8 3,2-c{9 -pyridines |
| DE2458965C3 (de) * | 1974-12-13 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | 3-Amino-indazol-N-carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| EP0708772B1 (en) | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
| US6022884A (en) * | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| WO2000038683A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| SI1194425T1 (sl) | 1999-06-23 | 2005-12-31 | Sanofi Aventis Deutschland | Substituirani benzimidazoli |
| AU778042B2 (en) * | 1999-10-19 | 2004-11-11 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| US6649654B1 (en) * | 1999-11-23 | 2003-11-18 | The Regents Of The University Of California | Methods for identifying and using IKK inhibitors |
| PT1254138E (pt) | 2000-02-09 | 2005-09-30 | Novartis Ag | Derivados de piridina que inibem a angiogenese e/ou o receptor de tirosina cinase do vegf |
| GB0003154D0 (en) | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| WO2001068648A1 (en) | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| AU2002211827B2 (en) | 2000-10-03 | 2006-12-14 | Bristol-Myers Squibb Company | Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same |
| WO2002030423A1 (en) | 2000-10-12 | 2002-04-18 | Smithkline Beecham Corporation | NF-λB INHIBITORS |
| EP1324759A4 (en) | 2000-10-12 | 2004-05-12 | Smithkline Beecham Corp | NF - G (K) B INHIBITORS |
| CA2427284A1 (en) | 2000-10-26 | 2002-05-30 | Tularik Inc. | Antiinflammation agents |
| AP1893A (en) * | 2000-12-01 | 2008-09-23 | Osi Pharm Inc | Compounds specific to adenosine A1, A2A and A3 receptor and uses thereof |
| JP2002193938A (ja) | 2000-12-01 | 2002-07-10 | Bayer Ag | ４−アリールピリジン誘導体 |
| US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
| US6506772B1 (en) * | 2000-12-15 | 2003-01-14 | Hoffmann-La Roche Inc. | Substituted [1,2,4]triazolo[1,5a]pyridine derivatives with activity as adenosine receptor ligands |
| MXPA03006817A (es) | 2001-02-01 | 2003-11-13 | Bristol Myers Squibb Co | Metodo de tratamiento de enfermedades inflamatorias e inmunes usando inhibidores de la ikb cinasa (ikk). |
| WO2002076985A1 (en) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| IL158574A0 (en) | 2001-05-24 | 2004-05-12 | Leo Pharma As | Novel pyridyl cyanoguanidine compounds |
| US20030045515A1 (en) | 2001-05-24 | 2003-03-06 | Lise Binderup | Combination medicament for treatment of neoplastic diseases |
| WO2002094265A1 (en) | 2001-05-24 | 2002-11-28 | Leo Pharma A/S | A method of modulating nf-$g(k)b activity |
| SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| JP2005507892A (ja) | 2001-09-19 | 2005-03-24 | ファルマシア・コーポレーション | 炎症の治療のための置換されたピラゾリルベンゼンスルファミド化合物 |
| MXPA04002667A (es) | 2001-09-19 | 2004-06-18 | Pharmacia Corp | Compuestos de pirazolilo sustituido para el tratamiento de la inflacion. |
| BR0212613A (pt) | 2001-09-19 | 2004-08-31 | Pharmacia Corp | Compostos de indazol substituìdos para o tratamento de inflamação |
| ATE363473T1 (de) | 2001-09-19 | 2007-06-15 | Pharmacia Corp | Substituierte pyrazoloverbindungen zur behandlung von entzündungen |
| DE60229975D1 (de) | 2001-10-04 | 2009-01-02 | Smithkline Beecham Corp | Nf-kb-inhibitoren |
| AU2002356871A1 (en) | 2001-10-30 | 2003-05-12 | Pharmacia Corporation | Heteroaromatic carboxamide derivatives for the treatment of inflammation |
| WO2003040131A1 (en) | 2001-11-07 | 2003-05-15 | F. Hoffmann-La Roche Ag | Aminopyrimidines and pyridines |
| DE60217532T8 (de) | 2001-11-07 | 2008-02-07 | Millennium Pharmaceuticals, Inc., Cambridge | Carboline derivate als ikb-inhibitoren zur behandlung des m ultiplen myelomas |
| US6659654B2 (en) * | 2002-02-13 | 2003-12-09 | Hon Hai Precision Ind. Co., Ltd. | Multi-core optical fiber connector |
| BR0307796A (pt) | 2002-02-19 | 2004-12-21 | Pharmacia Corp | Derivados tricìclicos de pirazol para o tratamento de inflamação |
| ES2291628T3 (es) | 2002-04-03 | 2008-03-01 | Bristol-Myers Squibb Company | Compuestos triciclicos a base de tiofeno y composiciones farmaceuticas que comprenden dichos compuestos. |
| TW200403991A (en) | 2002-04-11 | 2004-03-16 | Smithkline Beecham Corp | NF-κb inhibitors |
| EP1501805A1 (en) | 2002-05-09 | 2005-02-02 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| WO2003103648A1 (ja) | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | 糖尿病治療薬 |
| WO2003103658A1 (ja) | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | 免疫関連プロテインキナーゼ阻害剤 |
| AU2003240935A1 (en) | 2002-06-06 | 2003-12-22 | Smithkline Beecham Corporation | Nf-kb inhibitors |
| DK1513516T3 (da) | 2002-06-06 | 2009-10-19 | Boehringer Ingelheim Pharma | Substitueret 3-amino-thieno(2,3-b)-pyridin-2-carboxylsyreamid-forbindelser og fremgangsmåder til fremstilling og deres anvendelser |
| AU2003249683A1 (en) | 2002-06-06 | 2003-12-22 | Smithkline Beecham Corporation | Nf-:b inhibitors |
| EP1530565A1 (en) | 2002-07-19 | 2005-05-18 | Pharmacia Corporation | Substituted thiophene carboxamide compounds for the treatment of inflammation |
-
2003
- 2003-09-19 JP JP2004549954A patent/JP2006512313A/ja not_active Ceased
- 2003-09-19 US US10/666,857 patent/US7199119B2/en not_active Expired - Fee Related
- 2003-09-19 WO PCT/US2003/029143 patent/WO2004041285A1/en not_active Ceased
- 2003-09-19 AU AU2003270701A patent/AU2003270701B2/en not_active Ceased
- 2003-09-19 EP EP03752410A patent/EP1556053A4/en not_active Withdrawn
- 2003-09-19 CA CA002502429A patent/CA2502429A1/en not_active Abandoned
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2007
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| AU2003270701A1 (en) | 2004-06-07 |
| EP1556053A1 (en) | 2005-07-27 |
| JP2006512313A (ja) | 2006-04-13 |
| US20070155777A1 (en) | 2007-07-05 |
| US7199119B2 (en) | 2007-04-03 |
| WO2004041285A1 (en) | 2004-05-21 |
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