SK59999A3 - Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents - Google Patents

Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents Download PDF

Info

Publication number: SK59999A3
Authority: SK; Slovakia
Prior art keywords: phenyl; benzenesulfonamide; trifluoromethyl; pyrazol; alkyl
Prior art date: 1996-11-19

Application number

SK599-99A

Other languages

English (en)

Slovak (sk)

Inventor

Jaime L Masferrer

Amiram Raz

Original Assignee

Searle & Co

Priority date (The priority date 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 date listed.)

1996-11-19

Filing date

1997-11-19

Publication date

2000-01-18

1997-11-19 Application filed by Searle & Co filed Critical Searle & Co

2000-01-18 Publication of SK59999A3 publication Critical patent/SK59999A3/sk

Links

239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims abstract description 28
238000000034 method Methods 0.000 title claims description 38
239000004037 angiogenesis inhibitor Substances 0.000 title 1
-1 dihydrophthyl Chemical group 0.000 claims description 165
125000000217 alkyl group Chemical group 0.000 claims description 56
230000033115 angiogenesis Effects 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 18
239000000126 substance Substances 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
125000001145 hydrido group Chemical group *[H] 0.000 claims description 15
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 15
125000001188 haloalkyl group Chemical group 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
230000002265 prevention Effects 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 12
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
206010027476 Metastases Diseases 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
125000004438 haloalkoxy group Chemical group 0.000 claims description 9
230000009401 metastasis Effects 0.000 claims description 9
125000002971 oxazolyl group Chemical group 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000000842 isoxazolyl group Chemical group 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
206010029113 Neovascularisation Diseases 0.000 claims description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
125000001769 aryl amino group Chemical group 0.000 claims description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
239000011737 fluorine Substances 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
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
201000009273 Endometriosis Diseases 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
125000006001 difluoroethyl group Chemical group 0.000 claims description 3
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
125000006343 heptafluoro propyl group Chemical group 0.000 claims description 3
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
SZHKSRZKPUOAGO-UHFFFAOYSA-N 1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CCC1 SZHKSRZKPUOAGO-UHFFFAOYSA-N 0.000 claims description 2
RSABMOYFBOLDLO-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound CC1=CC=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 RSABMOYFBOLDLO-UHFFFAOYSA-N 0.000 claims description 2
RIZFWOPNUQFLEF-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1-(4-methylsulfonylphenyl)imidazole Chemical compound N=1C(C)=CN(C=2C=CC(=CC=2)S(C)(=O)=O)C=1C1=CC=C(Cl)C=C1 RIZFWOPNUQFLEF-UHFFFAOYSA-N 0.000 claims description 2
PEUVGLHBVHFKPT-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazole Chemical compound C1=CC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 PEUVGLHBVHFKPT-UHFFFAOYSA-N 0.000 claims description 2
KYNAWJZJGXEMMS-UHFFFAOYSA-N 2-chloro-1-methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=C(Cl)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 KYNAWJZJGXEMMS-UHFFFAOYSA-N 0.000 claims description 2
FQJOALWXRJKJFW-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 FQJOALWXRJKJFW-UHFFFAOYSA-N 0.000 claims description 2
HLSMDYHXAPYMPD-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-1-(2-phenylethyl)-5-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=C1C(F)(F)F)C=2C=CC(F)=CC=2)=NN1CCC1=CC=CC=C1 HLSMDYHXAPYMPD-UHFFFAOYSA-N 0.000 claims description 2
QDPWDPOAKFQYJR-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-phenyl-1,3-oxazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(C=2C=CC=CC=2)O1 QDPWDPOAKFQYJR-UHFFFAOYSA-N 0.000 claims description 2
UUVBGFWWLRWVAV-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-5-thiophen-2-yl-2-(trifluoromethyl)-1h-imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2SC=CC=2)NC(C(F)(F)F)=N1 UUVBGFWWLRWVAV-UHFFFAOYSA-N 0.000 claims description 2
NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
MOHZCSPHJUIPJF-UHFFFAOYSA-N 5-(4-fluorophenyl)-4-(4-methylsulfonylphenyl)-2-(trifluoromethyl)-1h-imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)NC(C(F)(F)F)=N1 MOHZCSPHJUIPJF-UHFFFAOYSA-N 0.000 claims description 2
APMIVVBYHLSFJD-UHFFFAOYSA-N 5-(difluoromethyl)-4-(4-methylsulfonylphenyl)-3-phenyl-1,2-oxazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C(F)F)ON=C1C1=CC=CC=C1 APMIVVBYHLSFJD-UHFFFAOYSA-N 0.000 claims description 2
208000007135 Retinal Neovascularization Diseases 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
125000004391 aryl sulfonyl group Chemical group 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
229940007550 benzyl acetate Drugs 0.000 claims description 2
210000004996 female reproductive system Anatomy 0.000 claims description 2
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 2
125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
LWIFWMYFVZYWMS-UHFFFAOYSA-N 1,2-difluoro-3-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=C(F)C=CC=2)F)CCC1 LWIFWMYFVZYWMS-UHFFFAOYSA-N 0.000 claims 1
GWMFOHRUWPDLIP-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-2-phenyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=C1 GWMFOHRUWPDLIP-UHFFFAOYSA-N 0.000 claims 1
JQDLRYPRLMZWFM-UHFFFAOYSA-N 1-methylsulfanyl-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)CCC1 JQDLRYPRLMZWFM-UHFFFAOYSA-N 0.000 claims 1
KSFMAASFLCWROX-UHFFFAOYSA-N 2,4-dichloro-1-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)CCC1 KSFMAASFLCWROX-UHFFFAOYSA-N 0.000 claims 1
AGCRHVNIFLDQNI-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazol-2-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N=C(CC(O)=O)O1 AGCRHVNIFLDQNI-UHFFFAOYSA-N 0.000 claims 1
AMTZZFUBJIWXKB-UHFFFAOYSA-N 2-tert-butyl-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-1,3-oxazole Chemical compound O1C(C(C)(C)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 AMTZZFUBJIWXKB-UHFFFAOYSA-N 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
RSYPHTZEXAJUHX-UHFFFAOYSA-N 4-[2-(3-fluoro-4-methoxyphenyl)cyclopenten-1-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1=C(C=2C=CC(=CC=2)S(N)(=O)=O)CCC1 RSYPHTZEXAJUHX-UHFFFAOYSA-N 0.000 claims 1
UFAWCYIJMWUQEO-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)-4,4-dimethylcyclopenten-1-yl]benzenesulfonamide Chemical compound C1C(C)(C)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(S(N)(=O)=O)C=C1 UFAWCYIJMWUQEO-UHFFFAOYSA-N 0.000 claims 1
SEOHAKCJVHNLFU-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)cyclopenten-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CCC1 SEOHAKCJVHNLFU-UHFFFAOYSA-N 0.000 claims 1
NTIRVNBDXWODFR-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-4,4-dimethylcyclopenten-1-yl]benzenesulfonamide Chemical compound C1C(C)(C)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(N)(=O)=O)C=C1 NTIRVNBDXWODFR-UHFFFAOYSA-N 0.000 claims 1
PISBIZMMMDTULP-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)cyclopenten-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC(F)=CC=2)CCC1 PISBIZMMMDTULP-UHFFFAOYSA-N 0.000 claims 1
FVYLDRLDRJJWDM-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound C1=NC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(N)(=O)=O)C=C1 FVYLDRLDRJJWDM-UHFFFAOYSA-N 0.000 claims 1
LBHBDZDYQHVSDV-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)phenyl]-5-(trifluoromethyl)-1H-pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C2=C(NN=C2)C(F)(F)F)=CC=C1C1=CC=C(F)C=C1 LBHBDZDYQHVSDV-UHFFFAOYSA-N 0.000 claims 1
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
125000006414 CCl Chemical group ClC* 0.000 claims 1
125000005553 heteroaryloxy group Chemical group 0.000 claims 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
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 1
230000002491 angiogenic effect Effects 0.000 abstract description 4
125000004432 carbon atom Chemical group C* 0.000 description 30
239000003112 inhibitor Substances 0.000 description 19
125000003545 alkoxy group Chemical group 0.000 description 16
108010037462 Cyclooxygenase 2 Proteins 0.000 description 15
102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 15
229940034982 antineoplastic agent Drugs 0.000 description 14
239000002246 antineoplastic agent Substances 0.000 description 14
239000002585 base Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 13
239000002253 acid Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
125000002768 hydroxyalkyl group Chemical group 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000005843 halogen group Chemical group 0.000 description 9
150000002460 imidazoles Chemical class 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 8
125000003282 alkyl amino group Chemical group 0.000 description 8
125000003710 aryl alkyl group Chemical group 0.000 description 8
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
125000004434 sulfur atom Chemical group 0.000 description 8
125000004183 alkoxy alkyl group Chemical group 0.000 description 7
201000010099 disease Diseases 0.000 description 7
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 7
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229960002066 vinorelbine Drugs 0.000 description 1
IQDSXWRQCKDBMW-NSFJATOBSA-N vintriptol Chemical compound C([C@@H](C[C@@](O)(CC)C1)C[C@@]2(C3=C(OC)C=C4N(C)[C@H]5[C@@]([C@@H]([C@]6(CC)C=CCN7CC[C@]5([C@H]67)C4=C3)O)(O)C(=O)N[C@@H](CC=3C4=CC=CC=C4NC=3)C(=O)OCC)C(=O)OC)N1CCC1=C2NC2=CC=CC=C12 IQDSXWRQCKDBMW-NSFJATOBSA-N 0.000 description 1
229950003415 vintriptol Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229950005839 vinzolidine Drugs 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
229960000641 zorubicin Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Oncology (AREA)
Ophthalmology & Optometry (AREA)
Reproductive Health (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)

SK599-99A 1996-11-19 1997-11-19 Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents SK59999A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3140496P	1996-11-19	1996-11-19
PCT/US1997/021489 WO1998022101A2 (en)	1996-11-19	1997-11-19	Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents

Publications (1)

Publication Number	Publication Date
SK59999A3 true SK59999A3 (en)	2000-01-18

Family

ID=21859277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK599-99A SK59999A3 (en)	1996-11-19	1997-11-19	Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents

Country Status (19)

Country	Link
EP (1)	EP0941080A2 (id)
JP (1)	JP2001505564A (id)
KR (1)	KR20000053362A (id)
CN (1)	CN1247470A (id)
AU (1)	AU730211B2 (id)
BR (1)	BR9713522A (id)
CA (1)	CA2270469C (id)
CZ (1)	CZ176899A3 (id)
ID (1)	ID21979A (id)
IL (1)	IL129604A (id)
NO (1)	NO992309D0 (id)
NZ (1)	NZ335853A (id)
PL (2)	PL194717B1 (id)
RO (1)	RO118566B1 (id)
RU (1)	RU2268716C2 (id)
SK (1)	SK59999A3 (id)
TR (1)	TR199901703T2 (id)
UA (1)	UA70294C2 (id)
WO (1)	WO1998022101A2 (id)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6515014B2 (en)	1995-06-02	2003-02-04	G. D. Searle & Co.	Thiophene substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors
US6512121B2 (en)	1998-09-14	2003-01-28	G.D. Searle & Co.	Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors
NZ333399A (en)	1997-12-24	2000-05-26	Sankyo Co	Cyclooxygenase-2 inhibitors (COX-2) for the prevention and treatment of tumors, cachexia and tumor-metastasis
US20030013739A1 (en) *	1998-12-23	2003-01-16	Pharmacia Corporation	Methods of using a combination of cyclooxygenase-2 selective inhibitors and thalidomide for the treatment of neoplasia
US6858598B1 (en)	1998-12-23	2005-02-22	G. D. Searle & Co.	Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
AU2592600A (en) *	1998-12-23	2000-07-31	G.D. Searle & Co.	Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6833373B1 (en)	1998-12-23	2004-12-21	G.D. Searle & Co.	Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
ATE306263T1 (de) *	1999-03-10	2005-10-15	Searle Llc	Zusammensetzungen zur verabreichung eines cyclooxygenase-2-hemmers an tiere
RU2268054C2 (ru) *	1999-07-29	2006-01-20	Амджен Инк.	Сочетанная терапия с использованием пентафторбензолсульфонамидов
IL152097A0 (en)	2000-05-19	2003-05-29	Applied Research Systems	Use of pyrazole derivatives for treating infertility
WO2002039958A2 (en)	2000-11-03	2002-05-23	Tularik Inc.	Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents
KR100686537B1 (ko) *	2001-12-28	2007-02-27	씨제이 주식회사	사이클로옥시게나제-2 의 저해제로서 선택성이 뛰어난디아릴 1,2,4-트리아졸 유도체
EP1530475A2 (en) *	2002-07-17	2005-05-18	Warner-Lambert Company LLC	Pharmaceutical compositions comprising an allosteric carboxylic inhibitor of matrix metalloproteinase-13 and a selective inhibitor of cyclooxygenase-2
KR100484525B1 (ko) *	2002-10-15	2005-04-20	씨제이 주식회사	이소티아졸 유도체, 그 제조방법 및 약제학적 조성물
RU2316295C1 (ru) *	2006-03-16	2008-02-10	Федеральное государственное учреждение "Межотраслевой научно-технический комплекс "Микрохирургия глаза" имени академика С.Н. Федорова Федерального агентства по здравоохранению и социальному развитию	Способ консервативного лечения гемангиомы придаточного аппарата глаза и орбиты у детей
AT504159A1 (de) *	2006-08-16	2008-03-15	Marlyn Nutraceuticals Inc	Verwendung von proteasen
RU2475257C1 (ru) *	2011-06-22	2013-02-20	Людмила Николаевна Третьяк	Средство для повышения адаптируемости организма к экстремальным условиям
GB2496135B (en) *	2011-11-01	2015-03-18	Valirx Plc	Inhibitors of the interaction between a Src family kinase and an androgen receptor or estradiol receptor for treatment of endometriosis

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0679157B1 (en) *	1993-01-15	1997-11-19	G.D. Searle & Co.	Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents
US5436265A (en) *	1993-11-12	1995-07-25	Merck Frosst Canada, Inc.	1-aroyl-3-indolyl alkanoic acids and derivatives thereof useful as anti-inflammatory agents
US5466823A (en) *	1993-11-30	1995-11-14	G.D. Searle & Co.	Substituted pyrazolyl benzenesulfonamides
DE69422306T4 (de) *	1993-11-30	2000-09-07	G.D. Searle & Co., Chicago	Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen
US5521213A (en) *	1994-08-29	1996-05-28	Merck Frosst Canada, Inc.	Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2
WO1996019469A1 (en) *	1994-12-21	1996-06-27	Merck Frosst Canada Inc.	Diaryl-2-(5h)-furanones as cox-2 inhibitors
US5691374A (en) *	1995-05-18	1997-11-25	Merck Frosst Canada Inc.	Diaryl-5-oxygenated-2-(5H) -furanones as COX-2 inhibitors

1997
- 1997-11-19 BR BR9713522A patent/BR9713522A/pt not_active Application Discontinuation
- 1997-11-19 NZ NZ335853A patent/NZ335853A/en not_active Application Discontinuation
- 1997-11-19 IL IL12960497A patent/IL129604A/en not_active IP Right Cessation
- 1997-11-19 WO PCT/US1997/021489 patent/WO1998022101A2/en not_active Ceased
- 1997-11-19 RO RO99-00572A patent/RO118566B1/ro unknown
- 1997-11-19 AU AU72982/98A patent/AU730211B2/en not_active Ceased
- 1997-11-19 PL PL97373973A patent/PL194717B1/pl unknown
- 1997-11-19 JP JP52396098A patent/JP2001505564A/ja not_active Withdrawn
- 1997-11-19 KR KR1019990704392A patent/KR20000053362A/ko not_active Withdrawn
- 1997-11-19 CN CN97181368A patent/CN1247470A/zh active Pending
- 1997-11-19 RU RU99112952/14A patent/RU2268716C2/ru not_active IP Right Cessation
- 1997-11-19 CZ CZ991768A patent/CZ176899A3/cs unknown
- 1997-11-19 ID IDW990379A patent/ID21979A/id unknown
- 1997-11-19 TR TR1999/01703T patent/TR199901703T2/xx unknown
- 1997-11-19 CA CA002270469A patent/CA2270469C/en not_active Expired - Fee Related
- 1997-11-19 EP EP97949579A patent/EP0941080A2/en not_active Withdrawn
- 1997-11-19 SK SK599-99A patent/SK59999A3/sk unknown
- 1997-11-19 UA UA99063447A patent/UA70294C2/uk unknown
1999
- 1999-04-30 PL PL333370A patent/PL191793B1/pl unknown
- 1999-05-12 NO NO992309A patent/NO992309D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
PL333370A1 (en)	1999-12-06
TR199901703T2 (xx)	2000-07-21
PL191793B1 (pl)	2006-07-31
KR20000053362A (ko)	2000-08-25
CA2270469A1 (en)	1998-05-28
ID21979A (id)	1999-08-19
IL129604A (en)	2004-08-31
AU7298298A (en)	1998-06-10
CN1247470A (zh)	2000-03-15
RO118566B1 (ro)	2003-07-30
UA70294C2 (en)	2004-10-15
NO992309L (no)	1999-05-12
WO1998022101A3 (en)	1998-06-25
EP0941080A2 (en)	1999-09-15
CZ176899A3 (cs)	1999-10-13
NZ335853A (en)	2002-02-01
CA2270469C (en)	2007-04-10
PL194717B1 (pl)	2007-06-29
BR9713522A (pt)	2000-03-21
JP2001505564A (ja)	2001-04-24
IL129604A0 (en)	2000-02-29
NO992309D0 (no)	1999-05-12
RU2268716C2 (ru)	2006-01-27
AU730211B2 (en)	2001-03-01
WO1998022101A2 (en)	1998-05-28

Publication	Publication Date	Title
US6025353A (en)	2000-02-15	Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents
RU2239429C2 (ru)	2004-11-10	Способ применения ингибиторов циклооксигеназы-2 для лечения и профилактики неоплазии
US5972986A (en)	1999-10-26	Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia
RU2268716C2 (ru)	2006-01-27	Способ применения ингибиторов циклооксигеназы-2 в качестве антиангиогенных средств
WO1998016227A9 (en)	1998-07-30	Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia
HUP9903342A2 (hu)	2000-02-28	Ciklooxigenáz-2 inhibitorok alkalmazása angiogenezissel kapcsolatos rendellenességek kezelésére és megelőzésére szolgáló gyógyászati készítmények előállítására
IL154502A (en)	2004-09-27	Use of cyclooxygenase-2 inhibitors in the preparation of medicaments for treating angiogenesis-related disorders
HK1026149A (en)	2000-12-08	Method of using cyclooxygenase-2 inhibitors as anti-angiogenic agents
NZ517374A (en)	2003-10-31	Method of using cycloozygenase-2 inhibitors to prevent a neoplasia that produces a prostaglandin