CZ298391B6 - Derivát pyrazolinu, zpusob jeho prípravy, jeho použití a farmaceutický prostredek, který ho obsahuje - Google Patents
Derivát pyrazolinu, zpusob jeho prípravy, jeho použití a farmaceutický prostredek, který ho obsahuje Download PDFInfo
- Publication number
- CZ298391B6 CZ298391B6 CZ20004418A CZ20004418A CZ298391B6 CZ 298391 B6 CZ298391 B6 CZ 298391B6 CZ 20004418 A CZ20004418 A CZ 20004418A CZ 20004418 A CZ20004418 A CZ 20004418A CZ 298391 B6 CZ298391 B6 CZ 298391B6
- Authority
- CZ
- Czechia
- Prior art keywords
- dihydro
- pyrazole
- trifluoromethyl
- methyl
- aminosulfonylphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 150000003219 pyrazolines Chemical class 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- -1 trifluoromethoxy, methylsulfonyl Chemical group 0.000 claims abstract description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims abstract description 23
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 206010061218 Inflammation Diseases 0.000 claims abstract description 18
- 230000004054 inflammatory process Effects 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 5
- 208000035475 disorder Diseases 0.000 claims abstract description 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims abstract 4
- 230000001404 mediated effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- ZZMJXWXXMAAPLI-UHFFFAOYSA-N 4-[3-(2,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(F)=CC=2)F)CC(C(F)(F)F)=N1 ZZMJXWXXMAAPLI-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 241000282412 Homo Species 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 206010037660 Pyrexia Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- HFHHSMJIOSROMS-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C#N)C1 HFHHSMJIOSROMS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 230000005526 G1 to G0 transition Effects 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000005518 carboxamido group Chemical group 0.000 claims 2
- NUUXNKLZACNVSR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC(F)=CC=2)F)N=C(C(F)(F)F)C1 NUUXNKLZACNVSR-UHFFFAOYSA-N 0.000 claims 1
- LLGLLZAAZOGDEB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound FC1=CC(F)=CC=C1N1N=C(C(F)(F)F)CC1 LLGLLZAAZOGDEB-UHFFFAOYSA-N 0.000 claims 1
- WYTGCYYFONATBA-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC(C)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 WYTGCYYFONATBA-UHFFFAOYSA-N 0.000 claims 1
- HSHVCHZVLHORQM-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC=CC=2)Cl)N=C(C(F)(F)F)C1 HSHVCHZVLHORQM-UHFFFAOYSA-N 0.000 claims 1
- SWAUQQYFPQVQSJ-UHFFFAOYSA-N 2-(3-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC=CC(N2C(CC(=N2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 SWAUQQYFPQVQSJ-UHFFFAOYSA-N 0.000 claims 1
- JBRFWCGJQZUHBW-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC(Cl)=CC=2)N=C(C(F)(F)F)C1 JBRFWCGJQZUHBW-UHFFFAOYSA-N 0.000 claims 1
- DXANXCBCSPZANW-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC(F)=CC=2)N=C(C(F)(F)F)C1 DXANXCBCSPZANW-UHFFFAOYSA-N 0.000 claims 1
- BQMJBDAPQSEBHC-UHFFFAOYSA-N 2-(4-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 BQMJBDAPQSEBHC-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- JGJAPXOXMKQZFJ-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)CC(C(F)(F)F)=N1 JGJAPXOXMKQZFJ-UHFFFAOYSA-N 0.000 claims 1
- WGTRCKXLJLADDX-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-methyl-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(F)C=C1 WGTRCKXLJLADDX-UHFFFAOYSA-N 0.000 claims 1
- ACXXZWIJKRQJLQ-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(N)=O)C1 ACXXZWIJKRQJLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- LQUHHIYASKFFMJ-UHFFFAOYSA-N 3-methyl-1h-pyrazole Chemical compound CC=1C=[C]NN=1 LQUHHIYASKFFMJ-UHFFFAOYSA-N 0.000 claims 1
- ZWPZGFZPOQCGAA-UHFFFAOYSA-N 3-phenyl-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC(C(O)=O)=N1 ZWPZGFZPOQCGAA-UHFFFAOYSA-N 0.000 claims 1
- WUVOXVYSEDDJEI-UHFFFAOYSA-N 4-[2-[5-(difluoromethyl)-3-(2,4-dimethylphenyl)-3,4-dihydropyrazol-2-yl]phenyl]aniline Chemical compound NC1=CC=C(C=C1)C1=C(C=CC=C1)N1N=C(CC1C1=C(C=C(C=C1)C)C)C(F)F WUVOXVYSEDDJEI-UHFFFAOYSA-N 0.000 claims 1
- VTYPWKRHGVKCAN-UHFFFAOYSA-N 4-[3-(2,3-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=C(F)C=CC=2)F)CC(C(F)(F)F)=N1 VTYPWKRHGVKCAN-UHFFFAOYSA-N 0.000 claims 1
- SLSINBTZGDBROZ-UHFFFAOYSA-N 4-[3-(2-fluoro-4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound FC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 SLSINBTZGDBROZ-UHFFFAOYSA-N 0.000 claims 1
- FUKIEVBHHBTNDY-UHFFFAOYSA-N 4-[3-(2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 FUKIEVBHHBTNDY-UHFFFAOYSA-N 0.000 claims 1
- INCZYKUDDWCUDZ-UHFFFAOYSA-N 4-[3-(3,4-dimethylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 INCZYKUDDWCUDZ-UHFFFAOYSA-N 0.000 claims 1
- SEEZUXWJFQKHJH-UHFFFAOYSA-N 4-[3-(3-fluoro-4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 SEEZUXWJFQKHJH-UHFFFAOYSA-N 0.000 claims 1
- DGRJCTLVHASBJO-UHFFFAOYSA-N 4-[3-(4-fluoro-2-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound COC1=CC(F)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 DGRJCTLVHASBJO-UHFFFAOYSA-N 0.000 claims 1
- NEVHKLLTWKFJOF-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)CC(C(F)(F)F)=N1 NEVHKLLTWKFJOF-UHFFFAOYSA-N 0.000 claims 1
- MQKGKXATGINIDF-UHFFFAOYSA-N 4-[3-(4-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 MQKGKXATGINIDF-UHFFFAOYSA-N 0.000 claims 1
- XFLCCCUNVGNSHZ-UHFFFAOYSA-N 4-[3-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)CC(C(F)(F)F)=N1 XFLCCCUNVGNSHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- NYHPBHAHZFULOT-UHFFFAOYSA-N 5-methyl-2-(4-methylsulfonylphenyl)-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazole Chemical compound C1C(C)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(C(F)(F)F)C=C1 NYHPBHAHZFULOT-UHFFFAOYSA-N 0.000 claims 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical group C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 claims 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- NCTYCSBNIWUFGY-UHFFFAOYSA-N n-[4-[3-(2,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C(=CC(F)=CC=2)F)CC(C(F)(F)F)=N1 NCTYCSBNIWUFGY-UHFFFAOYSA-N 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 22
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
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- 239000003480 eluent Substances 0.000 description 1
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- 238000009505 enteric coating Methods 0.000 description 1
- TZUYFNORLRBWLP-UHFFFAOYSA-N ethanimidoyl chloride Chemical compound CC(Cl)=N TZUYFNORLRBWLP-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
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- 230000002538 fungal effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- UKJFVOWPUXSBOM-UHFFFAOYSA-N hexane;oxolane Chemical compound C1CCOC1.CCCCCC UKJFVOWPUXSBOM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000000917 hyperalgesic effect Effects 0.000 description 1
- IFWQNANGFZLMEW-UHFFFAOYSA-N hypochlorous acid;(4-methylphenyl)hydrazine Chemical compound ClO.CC1=CC=C(NN)C=C1 IFWQNANGFZLMEW-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 1
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- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- BRWZPVRDOUWXKE-UHFFFAOYSA-N methylsulfanylmethane;trifluoroborane Chemical compound CSC.FB(F)F BRWZPVRDOUWXKE-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
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- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
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- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229940012982 picot Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 210000001991 scapula Anatomy 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 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 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
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- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009801129A ES2137138B1 (es) | 1998-05-29 | 1998-05-29 | Derivados de pirazolinas, su preparacion y su aplicacion como medicamentos. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20004418A3 CZ20004418A3 (en) | 2001-06-13 |
| CZ298391B6 true CZ298391B6 (cs) | 2007-09-19 |
Family
ID=8303969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20004418A CZ298391B6 (cs) | 1998-05-29 | 1999-05-27 | Derivát pyrazolinu, zpusob jeho prípravy, jeho použití a farmaceutický prostredek, který ho obsahuje |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6353117B1 (enExample) |
| EP (1) | EP1083171B1 (enExample) |
| JP (1) | JP4633928B2 (enExample) |
| KR (1) | KR100603666B1 (enExample) |
| CN (1) | CN1189459C (enExample) |
| AR (1) | AR018402A1 (enExample) |
| AT (1) | ATE265437T1 (enExample) |
| AU (1) | AU752001B2 (enExample) |
| BG (1) | BG64950B1 (enExample) |
| BR (1) | BR9910801A (enExample) |
| CA (1) | CA2333475C (enExample) |
| CO (1) | CO5031241A1 (enExample) |
| CU (1) | CU22995A3 (enExample) |
| CZ (1) | CZ298391B6 (enExample) |
| DE (1) | DE69916828T2 (enExample) |
| DK (1) | DK1083171T3 (enExample) |
| ES (2) | ES2137138B1 (enExample) |
| GE (1) | GEP20043237B (enExample) |
| HU (1) | HUP0102102A3 (enExample) |
| IS (1) | IS2040B (enExample) |
| LT (1) | LT4879B (enExample) |
| LV (1) | LV12632B (enExample) |
| NO (1) | NO316600B1 (enExample) |
| NZ (1) | NZ508990A (enExample) |
| PL (1) | PL344412A1 (enExample) |
| PT (1) | PT1083171E (enExample) |
| RU (1) | RU2233272C2 (enExample) |
| SI (1) | SI20580B (enExample) |
| SK (1) | SK285550B6 (enExample) |
| TW (1) | TW572898B (enExample) |
| WO (1) | WO1999062884A1 (enExample) |
| ZA (1) | ZA200007638B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ516553A (en) | 1999-06-16 | 2004-01-30 | Univ Temple | 1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2 and its preparation method |
| DE60016191T2 (de) | 1999-12-08 | 2005-12-22 | Pharmacia Corp., Chicago | Cyclooxygenase-2 hemmer enthaltende zusammensetzungen mit schnellem wirkungseintritt |
| ES2174757B1 (es) * | 2001-04-06 | 2003-11-01 | Esteve Labor Dr | Empleo de derivados de firazolinas en la elaboracion de un medicamentopara la prevencion y/o el tratamiento de enfermedades proliferativas celulares. |
| US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
| US6878729B2 (en) | 2001-05-04 | 2005-04-12 | The Procter & Gamble Company | Medicinal uses of dihydropyrazoles |
| ES2183720B1 (es) | 2001-06-18 | 2004-01-16 | Esteve Labor Dr | Procedimiento para la preparacion de derivados de 1,5-diaril-3-trifluorometil-delta2-pirazolinas racemicas y enantiomericamente puras. |
| WO2004098619A2 (en) | 2003-05-07 | 2004-11-18 | Osteologix A/S | Treating cartilage / bone conditions with water-soluble strontium salts |
| ES2238923B1 (es) * | 2004-02-16 | 2006-11-01 | Laboratorios Del Dr. Esteve, S.A. | Nuevos derivados pirazolinicos sustituidos. |
| US7998996B2 (en) * | 2004-02-17 | 2011-08-16 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| ES2257929B1 (es) * | 2004-07-16 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de pirazolina, procedimiento para su obtencion y utilizacion de los mismos como agentes terapeuticos. |
| ES2278503B1 (es) * | 2005-06-27 | 2008-06-16 | Laboratorios Del Dr. Esteve, S.A. | Epoxidacion de cetonas alfa, beta - insaturadas. |
| WO2007009710A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds: methods for their preparation |
| ES2336883B1 (es) * | 2005-07-15 | 2011-03-22 | Laboratorios Del Dr. Esteve, S.A. | Compuestos de pirazolina sustituidos, con una estereoquimica predeterminada, para la reduccion de trigliceridos en sangre. |
| EP1743636A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Combination of a substituted pyrazoline compound and a drug used in food-related disorders |
| WO2007009703A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | New formulations of substituted pyrazoline compounds |
| ES2330716B1 (es) * | 2005-07-15 | 2010-07-09 | Laboratorios Del Dr.Esteve, S.A. | Formulaciones farmaceuticas de compuestos de pirazolina sustituidos. |
| EP1743643A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | New formulations of substituted pyrazoline compounds |
| EP1743642A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds and their derivatives for the treatment of cannabinoid system-associated diseases |
| WO2007009698A1 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A | Combination of pyrazoline type cannabinoid receptor antagonist and statin |
| EP1745781A1 (en) * | 2005-07-15 | 2007-01-24 | Laboratorios Del Dr. Esteve, S.A. | Combination of pyrazoline type cannabinoid receptor antagonist and statin |
| EP1749526A1 (en) * | 2005-07-15 | 2007-02-07 | Laboratorios Del Dr. Esteve, S.A. | Use of substituted pyrazoline compounds for the treatment of food disorders, including obesity or metabolic syndrome in patients with developed diabetes |
| EP1743638A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios Del Dr. Esteve, S.A. | Pharmaceutical formulations of substituted pyrazoline compounds |
| ES2326725B1 (es) * | 2005-07-15 | 2010-05-11 | Laboratorios Del Dr. Esteve, S.A. | Uso de compuestos de pirazolina sustituidos para el tratamiento de trastornos alimentarios, que incluyen la obesidad o el sindrome metabolico en pacientes con diabetes desarrollada. |
| ES2316306B1 (es) * | 2005-07-15 | 2009-11-23 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de un compuesto de pirazolina sustituido y un farmaco utilizado en trastornos relacionados con los alimentos. |
| WO2007009692A1 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A | Use of substituted pyrazoline compounds for the treatment of food disorders, including obesity or metabolic syndrome in patients with developed diabetes |
| EP1849784A1 (en) * | 2006-04-26 | 2007-10-31 | Laboratorios Del Dr. Esteve, S.A. | Indoline-substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1743892A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1760078A1 (en) * | 2005-07-15 | 2007-03-07 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds; methods for their preparation |
| WO2007009699A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A | Use of substituted pyrazoline compounds and their derivatives for the treatment of cannabinoid system-associated diseases |
| EP1757587A1 (en) * | 2005-07-15 | 2007-02-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| WO2007009706A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| AR061623A1 (es) * | 2006-06-26 | 2008-09-10 | Novartis Ag | Derivados de acido fenilacetico |
| US20100111858A1 (en) * | 2007-01-19 | 2010-05-06 | Howard Carol P | Diangostic and Therapeutic Cyclooxygenase-2 Binding Ligands |
| EP3009137A1 (en) * | 2014-10-16 | 2016-04-20 | Ecuphar N.V. | Pyrazoline-derived compound and its use in a weekly dosage regime against inflammation and pain derived from degenerative joint disease in mammals |
| EP4029502A1 (en) | 2021-01-15 | 2022-07-20 | Ecuphar N.V. | Pyrazoline-derived compound (enflicoxib) for use in the prevention and/or treatment of pain and inflammation associated to surgery in mammals |
| CA3209491A1 (en) | 2021-03-15 | 2022-09-22 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory disease |
| US12208085B2 (en) | 2022-05-31 | 2025-01-28 | Ecuphar Nv | Pyrazoline-derived compound for use in the prevention and/or treatment of pain and inflammation associated to surgery in mammals |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425179A (en) * | 1979-10-18 | 1984-01-10 | Usm Corporation | Adhesive compositions |
| WO1988006583A1 (en) * | 1987-01-05 | 1988-09-07 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5818363A (ja) * | 1981-07-13 | 1983-02-02 | アメリカン・サイアナミド・カンパニ− | 複素環式置換アミノピラゾリン類およびその薬としての用途 |
| PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| AU708964B2 (en) * | 1995-05-25 | 1999-08-19 | G.D. Searle & Co. | Method of preparing 3-haloalkyl-1h-pyrazoles |
| GB9520584D0 (en) * | 1995-10-09 | 1995-12-13 | Fujisawa Pharmaceutical Co | Pyrazole derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
-
1998
- 1998-05-29 ES ES009801129A patent/ES2137138B1/es not_active Expired - Lifetime
-
1999
- 1999-05-27 CA CA002333475A patent/CA2333475C/en not_active Expired - Lifetime
- 1999-05-27 AR ARP990102513A patent/AR018402A1/es active IP Right Grant
- 1999-05-27 SK SK1807-2000A patent/SK285550B6/sk unknown
- 1999-05-27 AT AT99922192T patent/ATE265437T1/de active
- 1999-05-27 CZ CZ20004418A patent/CZ298391B6/cs not_active IP Right Cessation
- 1999-05-27 PL PL99344412A patent/PL344412A1/xx not_active IP Right Cessation
- 1999-05-27 HU HU0102102A patent/HUP0102102A3/hu unknown
- 1999-05-27 GE GEAP19995706A patent/GEP20043237B/en unknown
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- 1999-05-27 KR KR1020007013447A patent/KR100603666B1/ko not_active Expired - Fee Related
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- 2000-11-29 BG BG105005A patent/BG64950B1/bg unknown
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4425179A (en) * | 1979-10-18 | 1984-01-10 | Usm Corporation | Adhesive compositions |
| WO1988006583A1 (en) * | 1987-01-05 | 1988-09-07 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 19990527 |