RU2268716C2 - Способ применения ингибиторов циклооксигеназы-2 в качестве антиангиогенных средств - Google Patents

Info

Publication number

RU2268716C2

RU2268716C2 RU99112952/14A RU99112952A RU2268716C2 RU 2268716 C2 RU2268716 C2 RU 2268716C2 RU 99112952/14 A RU99112952/14 A RU 99112952/14A RU 99112952 A RU99112952 A RU 99112952A RU 2268716 C2 RU2268716 C2 RU 2268716C2

Authority

RU

Russia

Prior art keywords

radicals

benzenesulfonamide

pyrazol

phenyl

trifluoromethyl

Prior art date

1996-11-19

Links

• Espacenet
• Global Dossier
• Discuss

• 239000002599 prostaglandin synthase inhibitor Substances 0.000 title abstract 2
• 239000004037 angiogenesis inhibitor Substances 0.000 title 1
• 230000033115 angiogenesis Effects 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 206010027476 Metastases Diseases 0.000 claims abstract description 10
• 230000009401 metastasis Effects 0.000 claims abstract description 10
• 239000003814 drug Substances 0.000 claims abstract description 9
• 206010012689 Diabetic retinopathy Diseases 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 50
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 32
• 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 11
• 208000035475 disorder Diseases 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 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 description 6
• 230000001772 anti-angiogenic effect Effects 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 4
• YDUQOLMYSBDZFO-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-phenylpyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C=2C=CC=CC=2)=N1 YDUQOLMYSBDZFO-UHFFFAOYSA-N 0.000 claims description 3
• 201000009273 Endometriosis Diseases 0.000 claims description 3
• 210000004994 reproductive system Anatomy 0.000 claims description 2
• 206010029113 Neovascularisation Diseases 0.000 claims 1
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• 230000004256 retinal image Effects 0.000 claims 1
• 210000001210 retinal vessel Anatomy 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 18
• 238000011321 prophylaxis Methods 0.000 abstract description 13
• 230000000694 effects Effects 0.000 abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract description 5
• 239000000126 substance Substances 0.000 abstract description 5
• -1 halogenated Chemical group 0.000 description 195
• 150000003254 radicals Chemical class 0.000 description 64
• 238000000034 method Methods 0.000 description 39
• 125000004432 carbon atom Chemical group C* 0.000 description 30
• 125000000217 alkyl group Chemical group 0.000 description 26
• 229910052736 halogen Inorganic materials 0.000 description 17
• 239000002246 antineoplastic agent Substances 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
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• 125000003545 alkoxy group Chemical group 0.000 description 14
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• 125000000623 heterocyclic group Chemical group 0.000 description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 description 12
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 125000003282 alkyl amino group Chemical group 0.000 description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
• 125000001188 haloalkyl group Chemical group 0.000 description 10
• 229910052739 hydrogen Inorganic materials 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 10
• 239000003112 inhibitor Substances 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
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 238000010586 diagram Methods 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
• 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
• 239000003795 chemical substances by application Substances 0.000 description 8
• 150000002460 imidazoles Chemical class 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
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 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 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 210000004204 blood vessel Anatomy 0.000 description 7
• 125000004181 carboxyalkyl group Chemical group 0.000 description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 7
• 150000003180 prostaglandins Chemical class 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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• 206010061218 Inflammation Diseases 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000004414 alkyl thio group Chemical group 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 description 6
• 229940088598 enzyme Drugs 0.000 description 6
• 230000004054 inflammatory process Effects 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000004430 oxygen atom Chemical group O* 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
• 150000005840 aryl radicals Chemical class 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 125000005594 diketone group Chemical group 0.000 description 5
• 201000010099 disease Diseases 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 125000004438 haloalkoxy group Chemical group 0.000 description 5
• 150000002431 hydrogen Chemical class 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 125000004076 pyridyl group Chemical group 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 108050007372 Fibroblast Growth Factor Proteins 0.000 description 4
• 102000018233 Fibroblast Growth Factor Human genes 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
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• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
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