AU730211B2 - Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents - Google Patents

Info

Publication number

AU730211B2

AU730211B2 AU72982/98A AU7298298A AU730211B2 AU 730211 B2 AU730211 B2 AU 730211B2 AU 72982/98 A AU72982/98 A AU 72982/98A AU 7298298 A AU7298298 A AU 7298298A AU 730211 B2 AU730211 B2 AU 730211B2

Authority

AU

Australia

Prior art keywords

alkyl

phenyl

pyrazol

trifluoromethyl

aryl

Prior art date

1996-11-19

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 53
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims description 34
• 239000004037 angiogenesis inhibitor Substances 0.000 title description 2
• -1 thiazolyJ- Chemical group 0.000 claims description 294
• 150000003254 radicals Chemical class 0.000 claims description 85
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 73
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 150000001875 compounds Chemical class 0.000 claims description 60
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
• 229910052799 carbon Inorganic materials 0.000 claims description 45
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 38
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 230000033115 angiogenesis Effects 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 20
• 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 19
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 19
• 208000035475 disorder Diseases 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
• 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 206010027476 Metastases Diseases 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 230000009401 metastasis Effects 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 206010029113 Neovascularisation Diseases 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 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
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 239000004305 biphenyl Substances 0.000 claims description 4
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 210000004996 female reproductive system Anatomy 0.000 claims description 4
• 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 3
• 208000007135 Retinal Neovascularization Diseases 0.000 claims description 3
• 229940022663 acetate Drugs 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• 229940007550 benzyl acetate Drugs 0.000 claims description 3
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• UJSFKTUZOASIPA-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 UJSFKTUZOASIPA-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000005110 aryl thio group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 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 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 2
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 5
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
• 208000001969 capillary hemangioma Diseases 0.000 claims 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
• IBPHXKCFBXEFQP-UHFFFAOYSA-N 1,1,1,2,2-pentafluoroethane Chemical class F[C](F)C(F)(F)F IBPHXKCFBXEFQP-UHFFFAOYSA-N 0.000 claims 1
• GYVQJKAKUBGYSE-UHFFFAOYSA-N 1-(fluoromethyl)imidazole Chemical compound FCN1C=CN=C1 GYVQJKAKUBGYSE-UHFFFAOYSA-N 0.000 claims 1
• RLXUXICUOSILHE-UHFFFAOYSA-N 1-(trifluoromethyl)imidazole Chemical compound FC(F)(F)N1C=CN=C1 RLXUXICUOSILHE-UHFFFAOYSA-N 0.000 claims 1
• JDCLOWORQIDWQP-UHFFFAOYSA-N 1-(trifluoromethyl)pyrazole Chemical compound FC(F)(F)N1C=CC=N1 JDCLOWORQIDWQP-UHFFFAOYSA-N 0.000 claims 1
• OOVPOOSHEJECDK-UHFFFAOYSA-N 4-(2-phenylethyl)-5-(trifluoromethyl)-1H-pyrazole Chemical compound C1(=CC=CC=C1)CCC=1C(=NNC=1)C(F)(F)F OOVPOOSHEJECDK-UHFFFAOYSA-N 0.000 claims 1
• IIQIBRLYHGPETH-UHFFFAOYSA-N 4-[4-(hydroxymethyl)triazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1N=NC(CO)=C1 IIQIBRLYHGPETH-UHFFFAOYSA-N 0.000 claims 1
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