AU2003303641A1 - Anti-inflammatory medicaments - Google Patents
Anti-inflammatory medicaments Download PDFInfo
- Publication number
- AU2003303641A1 AU2003303641A1 AU2003303641A AU2003303641A AU2003303641A1 AU 2003303641 A1 AU2003303641 A1 AU 2003303641A1 AU 2003303641 A AU2003303641 A AU 2003303641A AU 2003303641 A AU2003303641 A AU 2003303641A AU 2003303641 A1 AU2003303641 A1 AU 2003303641A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- pct
- formula
- phenyl
- 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
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- 239000003814 drug Substances 0.000 title description 10
- 230000003110 anti-inflammatory effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 216
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
- -1 heterocyclylaminos Chemical group 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 239000003446 ligand Substances 0.000 claims description 62
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 50
- 230000027455 binding Effects 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 43
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 38
- 108091000080 Phosphotransferase Proteins 0.000 claims description 36
- 102000020233 phosphotransferase Human genes 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 230000004913 activation Effects 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 12
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 206010011703 Cyanosis Diseases 0.000 claims description 10
- 125000000539 amino acid group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
- 206010040070 Septic Shock Diseases 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 206010040047 Sepsis Diseases 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 230000001537 neural effect Effects 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 206010014824 Endotoxic shock Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 102000001253 Protein Kinase Human genes 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 3
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 208000028867 ischemia Diseases 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 108060006633 protein kinase Proteins 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001433 C-terminal amino-acid group Chemical group 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 102220009099 rs1042820 Human genes 0.000 claims description 2
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 230000009149 molecular binding Effects 0.000 claims 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 102220541385 3 beta-hydroxysteroid dehydrogenase/Delta 5->4-isomerase type 1_R71I_mutation Human genes 0.000 claims 1
- 241001181114 Neta Species 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 101150012912 mec-7 gene Proteins 0.000 claims 1
- 102220222128 rs1060500644 Human genes 0.000 claims 1
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- 102220123387 rs80356804 Human genes 0.000 claims 1
- 102220134064 rs886055163 Human genes 0.000 claims 1
- 125000005289 uranyl group Chemical group 0.000 claims 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 description 122
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 61
- 238000005481 NMR spectroscopy Methods 0.000 description 55
- 239000002585 base Substances 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- 150000001412 amines Chemical class 0.000 description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 45
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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| US43741502P | 2002-12-31 | 2002-12-31 | |
| US43730402P | 2002-12-31 | 2002-12-31 | |
| US43748702P | 2002-12-31 | 2002-12-31 | |
| US43740302P | 2002-12-31 | 2002-12-31 | |
| US60/437,487 | 2002-12-31 | ||
| US60/437,304 | 2002-12-31 | ||
| US60/437,403 | 2002-12-31 | ||
| US60/437,415 | 2002-12-31 | ||
| US46380403P | 2003-04-18 | 2003-04-18 | |
| US60/463,804 | 2003-04-18 | ||
| US10/746,460 US7144911B2 (en) | 2002-12-31 | 2003-12-24 | Anti-inflammatory medicaments |
| US10/746,460 | 2003-12-24 | ||
| PCT/US2003/041449 WO2004060306A2 (en) | 2002-12-31 | 2003-12-26 | Anti-inflammatory medicaments |
Publications (1)
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| AU2003303641A1 true AU2003303641A1 (en) | 2004-07-29 |
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| US (7) | US7144911B2 (https=) |
| EP (2) | EP1590344A4 (https=) |
| JP (1) | JP2006514691A (https=) |
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| BR (1) | BR0317872A (https=) |
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| MX (1) | MXPA05007236A (https=) |
| TW (1) | TW200427672A (https=) |
| WO (2) | WO2004060305A2 (https=) |
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- 2003-12-26 AU AU2003303641A patent/AU2003303641A1/en not_active Abandoned
- 2003-12-26 WO PCT/US2003/041449 patent/WO2004060306A2/en not_active Ceased
- 2003-12-30 TW TW092137451A patent/TW200427672A/zh unknown
-
2006
- 2006-01-20 US US11/337,245 patent/US20080187978A1/en not_active Abandoned
- 2006-06-09 US US11/450,850 patent/US7666895B2/en not_active Expired - Fee Related
- 2006-06-09 US US11/450,842 patent/US20090105230A1/en not_active Abandoned
- 2006-06-09 US US11/450,852 patent/US20090069310A1/en not_active Abandoned
- 2006-06-09 US US11/450,849 patent/US7737283B2/en not_active Expired - Fee Related
- 2006-06-09 US US11/450,851 patent/US20090137021A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR0317872A (pt) | 2005-12-06 |
| WO2004060306A2 (en) | 2004-07-22 |
| EP1585734A2 (en) | 2005-10-19 |
| US20040180906A1 (en) | 2004-09-16 |
| US20090137021A1 (en) | 2009-05-28 |
| US7144911B2 (en) | 2006-12-05 |
| US7737283B2 (en) | 2010-06-15 |
| US20080299639A1 (en) | 2008-12-04 |
| US20090069310A1 (en) | 2009-03-12 |
| WO2004060305A2 (en) | 2004-07-22 |
| US20080187978A1 (en) | 2008-08-07 |
| EP1585734A4 (en) | 2007-09-19 |
| MXPA05007236A (es) | 2006-04-27 |
| EP1590344A2 (en) | 2005-11-02 |
| CA2513627A1 (en) | 2004-07-22 |
| US20090105230A1 (en) | 2009-04-23 |
| WO2004060305A3 (en) | 2005-02-10 |
| JP2006514691A (ja) | 2006-05-11 |
| US20090075986A1 (en) | 2009-03-19 |
| TW200427672A (en) | 2004-12-16 |
| US7666895B2 (en) | 2010-02-23 |
| EP1590344A4 (en) | 2007-08-29 |
| WO2004060306A3 (en) | 2005-07-28 |
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Legal Events
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| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE NAME OF THE APPLICANT FROM DECIPHERA PHARMACEUTICALS, INCTO DECIPHERA PHARMACEUTICALS, LLC Free format text: THE NATURE OF THE AMENDMENT IS: AMEND CO-INVENTOR NAME FROM PETRILLO, PETER A. TO PETILLO, PETER A. |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |