LT4879B - Pirazolino dariniai, jų gavimas ir jų panaudojimas vaistams - Google Patents

Pirazolino dariniai, jų gavimas ir jų panaudojimas vaistams Download PDF

Info

Publication number: LT4879B
Authority: LT; Lithuania
Prior art keywords: dihydro; pyrazole; trifluoromethyl; aminosulfonylphenyl; methylsulfonylphenyl
Prior art date: 1998-05-29

Application number

LT2000108A

Other languages

English (en)

Lithuanian (lt)

Other versions

LT2000108A (en

Inventor

Maria Rosa Cuberes-Altisent

Juana Maria Berrocal-Romero

Maria Montserrat Contijoch-Llobet

Jordi Frigola-Constansa

Original Assignee

Laboratorios Del Dr. Esteve,S.A.

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.)

1998-05-29

Filing date

2000-11-28

Publication date

2002-01-25

2000-11-28 Application filed by Laboratorios Del Dr. Esteve,S.A. filed Critical Laboratorios Del Dr. Esteve,S.A.

2001-09-25 Publication of LT2000108A publication Critical patent/LT2000108A/xx

2002-01-25 Publication of LT4879B publication Critical patent/LT4879B/lt

Links

150000003219 pyrazolines Chemical class 0.000 title claims abstract description 20
239000003814 drug Substances 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 63
238000000034 method Methods 0.000 claims abstract description 36
108010037462 Cyclooxygenase 2 Proteins 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 20
206010061218 Inflammation Diseases 0.000 claims abstract description 15
230000004054 inflammatory process Effects 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
208000002193 Pain Diseases 0.000 claims abstract description 5
206010037660 Pyrexia Diseases 0.000 claims abstract description 4
206010003246 arthritis Diseases 0.000 claims abstract description 4
102000010907 Cyclooxygenase 2 Human genes 0.000 claims abstract 2
230000001404 mediated effect Effects 0.000 claims abstract 2
-1 methyl fluoromethyl difluoromethyl trifluoromethyl carboxylic acid Chemical compound 0.000 claims description 61
239000000203 mixture Substances 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 27
239000000460 chlorine Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
229910052731 fluorine Inorganic materials 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 12
230000005764 inhibitory process Effects 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 7
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 7
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
230000002757 inflammatory effect Effects 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 5
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
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 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
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 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
239000012346 acetyl chloride Substances 0.000 claims description 3
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 description 3
150000007530 organic bases Chemical class 0.000 claims description 3
YACZNKGYISHAOT-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(O)=O)C1 YACZNKGYISHAOT-UHFFFAOYSA-N 0.000 claims description 2
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
125000005599 alkyl carboxylate group Chemical group 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
KJGXEXQQMOLYDH-UHFFFAOYSA-N methyl 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-3,4-dihydropyrazole-5-carboxylate Chemical compound C1C(C(=O)OC)=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C1C1=CC=C(C)C=C1 KJGXEXQQMOLYDH-UHFFFAOYSA-N 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
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
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 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
FTMOPUYNYHRMFN-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C(=CC(Cl)=CC=2)Cl)N=C(C(F)(F)F)C1 FTMOPUYNYHRMFN-UHFFFAOYSA-N 0.000 claims 1
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
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
RTHYHPLQWLNMPZ-UHFFFAOYSA-N 2-(4-chloro-2-methylphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound CC1=CC(Cl)=CC=C1N1C(C=2C=CC(=CC=2)S(C)(=O)=O)CC(C(F)(F)F)=N1 RTHYHPLQWLNMPZ-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
ICDOEQFGMOCZMV-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC=CC=2)CC(C(F)(F)F)=N1 ICDOEQFGMOCZMV-UHFFFAOYSA-N 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
MYEDBOXTBGKCOU-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)CC(C(F)(F)F)=N1 MYEDBOXTBGKCOU-UHFFFAOYSA-N 0.000 claims 1
FRQSGXCNDIYEIH-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C(=CC=CC=2)F)CC(C(F)(F)F)=N1 FRQSGXCNDIYEIH-UHFFFAOYSA-N 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
UCLTWOHUTQRYOX-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=C(F)C=CC=2)CC(C(F)(F)F)=N1 UCLTWOHUTQRYOX-UHFFFAOYSA-N 0.000 claims 1
SCPUBMXALQFIJC-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(F)=CC=2)CC(C(F)(F)F)=N1 SCPUBMXALQFIJC-UHFFFAOYSA-N 0.000 claims 1
DUWSUJBWSUSJSF-UHFFFAOYSA-N 3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C(C(F)(F)F)C1 DUWSUJBWSUSJSF-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
SALWHXXPZFQWIF-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-2-phenyl-5-(trifluoromethyl)-3,4-dihydropyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1N(C=2C=CC=CC=2)N=C(C(F)(F)F)C1 SALWHXXPZFQWIF-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
SCJYUURHLNBEIH-UHFFFAOYSA-N 3-phenyl-2-(4-sulfamoylphenyl)-3,4-dihydropyrazole-5-carboxamide Chemical compound C1C(C(=O)N)=NN(C=2C=CC(=CC=2)S(N)(=O)=O)C1C1=CC=CC=C1 SCJYUURHLNBEIH-UHFFFAOYSA-N 0.000 claims 1
WXELPGWWHJCPHS-UHFFFAOYSA-N 4-[3-(2,4-dichlorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)CC(C(F)(F)F)=N1 WXELPGWWHJCPHS-UHFFFAOYSA-N 0.000 claims 1
JQBARVBPEJYKGP-UHFFFAOYSA-N 4-[3-(2,4-dimethoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 JQBARVBPEJYKGP-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
GGIFCPPVQVEHCG-UHFFFAOYSA-N 4-[3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound FC1=CC(C)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 GGIFCPPVQVEHCG-UHFFFAOYSA-N 0.000 claims 1
ASUHJSUSKBNECS-UHFFFAOYSA-N 4-[3-(2-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC=CC=2)F)CC(C(F)(F)F)=N1 ASUHJSUSKBNECS-UHFFFAOYSA-N 0.000 claims 1
FFZJOJGVAOJVOA-UHFFFAOYSA-N 4-[3-(3,4-difluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=C(F)C(F)=CC=2)CC(C(F)(F)F)=N1 FFZJOJGVAOJVOA-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
WWTIGFLZKWDAKZ-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-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)CC(C(F)(F)F)=N1 WWTIGFLZKWDAKZ-UHFFFAOYSA-N 0.000 claims 1
DASSSRCBIOPSDJ-UHFFFAOYSA-N 4-[3-(3-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC(C2N(N=C(C2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 DASSSRCBIOPSDJ-UHFFFAOYSA-N 0.000 claims 1
AXMQEIGLBBEBIR-UHFFFAOYSA-N 4-[3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)F)CC(C(F)(F)F)=N1 AXMQEIGLBBEBIR-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
FBBVAAMIUGCGKM-UHFFFAOYSA-N 4-[3-(4-fluoro-2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(F)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 FBBVAAMIUGCGKM-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
QAPXFHIPWJILOM-UHFFFAOYSA-N 4-[3-(4-methoxy-2-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 QAPXFHIPWJILOM-UHFFFAOYSA-N 0.000 claims 1
VBHSLDFADJEMET-UHFFFAOYSA-N 4-[3-(4-methoxy-3-methylphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=C(C)C(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 VBHSLDFADJEMET-UHFFFAOYSA-N 0.000 claims 1
BSYNCTSOUUMGKG-UHFFFAOYSA-N 4-[3-(4-methoxyphenyl)-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(C=2C=CC(=CC=2)S(N)(=O)=O)N=C(C(F)(F)F)C1 BSYNCTSOUUMGKG-UHFFFAOYSA-N 0.000 claims 1
VEMICYBXEGHMIY-UHFFFAOYSA-N 4-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C(F)(F)F)=N1 VEMICYBXEGHMIY-UHFFFAOYSA-N 0.000 claims 1
IFRATYFQLPOODQ-UHFFFAOYSA-N 4-[3-[4-(trifluoromethoxy)phenyl]-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(OC(F)(F)F)=CC=2)CC(C(F)(F)F)=N1 IFRATYFQLPOODQ-UHFFFAOYSA-N 0.000 claims 1
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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
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DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
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239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
TZUYFNORLRBWLP-UHFFFAOYSA-N ethanimidoyl chloride Chemical compound CC(Cl)=N TZUYFNORLRBWLP-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
231100001014 gastrointestinal tract lesion Toxicity 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
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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
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BRWZPVRDOUWXKE-UHFFFAOYSA-N methylsulfanylmethane;trifluoroborane Chemical compound CSC.FB(F)F BRWZPVRDOUWXKE-UHFFFAOYSA-N 0.000 description 1
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231100000417 nephrotoxicity Toxicity 0.000 description 1
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235000005985 organic acids Nutrition 0.000 description 1
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FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
229940012982 picot Drugs 0.000 description 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
229960002702 piroxicam Drugs 0.000 description 1
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230000003334 potential effect Effects 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
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
230000009467 reduction Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
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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)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (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)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

LT2000108A 1998-05-29 2000-11-28 Pirazolino dariniai, jų gavimas ir jų panaudojimas vaistams LT4879B (lt)

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
LT2000108A LT2000108A (en)	2001-09-25
LT4879B true LT4879B (lt)	2002-01-25

Family

ID=8303969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LT2000108A LT4879B (lt)	1998-05-29	2000-11-28	Pirazolino dariniai, jų gavimas ir jų panaudojimas vaistams

Country Status (32)

Country	Link
US (2)	USRE38963E1 (fr)
EP (1)	EP1083171B1 (fr)
JP (1)	JP4633928B2 (fr)
KR (1)	KR100603666B1 (fr)
CN (1)	CN1189459C (fr)
AR (1)	AR018402A1 (fr)
AT (1)	ATE265437T1 (fr)
AU (1)	AU752001B2 (fr)
BG (1)	BG64950B1 (fr)
BR (1)	BR9910801A (fr)
CA (1)	CA2333475C (fr)
CO (1)	CO5031241A1 (fr)
CU (1)	CU22995A3 (fr)
CZ (1)	CZ298391B6 (fr)
DE (1)	DE69916828T2 (fr)
DK (1)	DK1083171T3 (fr)
ES (2)	ES2137138B1 (fr)
GE (1)	GEP20043237B (fr)
HU (1)	HUP0102102A3 (fr)
IS (1)	IS2040B (fr)
LT (1)	LT4879B (fr)
LV (1)	LV12632B (fr)
NO (1)	NO316600B1 (fr)
NZ (1)	NZ508990A (fr)
PL (1)	PL344412A1 (fr)
PT (1)	PT1083171E (fr)
RU (1)	RU2233272C2 (fr)
SI (1)	SI20580B (fr)
SK (1)	SK285550B6 (fr)
TW (1)	TW572898B (fr)
WO (1)	WO1999062884A1 (fr)
ZA (1)	ZA200007638B (fr)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU771668C (en)	1999-06-16	2005-08-11	Temple University - Of The Commonwealth System Of Higher Education	1-(4-sulfamylaryl)-3-substituted-5-aryl-2-pyrazolines as inhibitors of cyclooxygenase-2
KR100793668B1 (ko)	1999-12-08	2008-01-10	파마시아 코포레이션	강화된 생체이용률을 지닌 고체상 형태의 셀레콕시브
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.
ES2275218T3 (es)	2003-05-07	2007-06-01	Osteologix A/S	Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos.
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.
WO2007009699A2 (fr) *	2005-07-15	2007-01-25	Laboratorios Del Dr. Esteve, S.A	Utilisation de composes pyrazoliniques substitues et de leurs derives contre des affections associees au systeme des cannabinoides
EP1749526A1 (fr) *	2005-07-15	2007-02-07	Laboratorios Del Dr. Esteve, S.A.	Utilisation des derivés de la pyrazoline pour le traitement des troubles alimentaires, comme l'obesité ou le syndrome métabolique chez les patients diabetiques
WO2007009693A1 (fr) *	2005-07-15	2007-01-25	Laboratorios Del Dr.Esteve, S.A	Combinaison d'un compose pyrazolinique substitue et medicament utilise pour des troubles en lien avec les aliments
WO2007009692A1 (fr) *	2005-07-15	2007-01-25	Laboratorios Del Dr. Esteve, S.A	Utilisation de composes de pyrazoline substituee pour le traitement de troubles de l'alimentation dont l'obesite ou le syndrome metabolique chez des patients a diabete developpe.
EP1743892A1 (fr) *	2005-07-15	2007-01-17	Laboratorios del Dr. Esteve S.A.	Composés pyrazoline substitués, leur préparation et utilisation comme médicaments
WO2007009702A2 (fr) *	2005-07-15	2007-01-25	Laboratorios Del Dr. Esteve, S.A.	Composes de pyrazoline substitues, leur preparation et leur utilisation comme medicaments
WO2007009683A2 (fr) *	2005-07-15	2007-01-25	Laboratorios Del Dr.Esteve, S.A.	Formulations pharmaceutiques comprenant des composes de pyrazoline substitues
EP1743636A1 (fr) *	2005-07-15	2007-01-17	Laboratorios Del Dr. Esteve, S.A.	Combinaison d'une pyrazoline substituée avec un agent utilisé contre les dérangements alimentaires
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1999
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Publication number	Publication date
JP4633928B2 (ja)	2011-02-16
NO20006029L (no)	2001-01-26
BR9910801A (pt)	2001-11-27
HUP0102102A2 (hu)	2002-03-28
CZ298391B6 (cs)	2007-09-19
JP2002516908A (ja)	2002-06-11
HUP0102102A3 (en)	2002-06-28
NZ508990A (en)	2002-12-20
CA2333475A1 (fr)	1999-12-09
CA2333475C (fr)	2009-12-08
WO1999062884A1 (fr)	1999-12-09
SI20580B (sl)	2007-10-31
AR018402A1 (es)	2001-11-14
ES2137138A1 (es)	1999-12-01
PL344412A1 (en)	2001-11-05
BG64950B1 (bg)	2006-10-31
TW572898B (en)	2004-01-21
SK285550B6 (sk)	2007-03-01
LV12632B (en)	2001-07-20
ES2221382T3 (es)	2004-12-16
ES2137138B1 (es)	2000-09-16
AU752001B2 (en)	2002-09-05
IS5736A (is)	2000-11-28
NO20006029D0 (no)	2000-11-28
SI20580A (sl)	2001-12-31
CZ20004418A3 (en)	2001-06-13
KR100603666B1 (ko)	2006-07-24
US6353117B1 (en)	2002-03-05
BG105005A (en)	2001-08-31
CN1189459C (zh)	2005-02-16
CO5031241A1 (es)	2001-04-27
LT2000108A (en)	2001-09-25
GEP20043237B (en)	2004-05-25
EP1083171B1 (fr)	2004-04-28
NO316600B1 (no)	2004-03-01
SK18072000A3 (sk)	2001-07-10
ATE265437T1 (de)	2004-05-15
PT1083171E (pt)	2004-09-30
AU3932999A (en)	1999-12-20
ZA200007638B (en)	2001-11-13
CN1307566A (zh)	2001-08-08
DE69916828D1 (de)	2004-06-03
LV12632A (lv)	2001-03-20
DK1083171T3 (da)	2004-08-09
CU22995A3 (es)	2004-10-12
KR20010052437A (ko)	2001-06-25
IS2040B (is)	2005-08-15
USRE38963E1 (en)	2006-01-31
RU2233272C2 (ru)	2004-07-27
EP1083171A1 (fr)	2001-03-14
DE69916828T2 (de)	2005-04-14

Legal Events

Date	Code	Title	Description
2009-01-26	MM9A	Lapsed patents	Effective date: 20080527

Publication	Publication Date	Title
LT4879B (lt)	2002-01-25	Pirazolino dariniai, jų gavimas ir jų panaudojimas vaistams
DE69422306T2 (de)	2000-05-18	Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen
US5434178A (en)	1995-07-18	1,3,5 trisubstituted pyrazole compounds for treatment of inflammation
US5508426A (en)	1996-04-16	Substituted pyrazolyl benzenesulfonamide compounds for the treatment of inflammation
TWI449696B (zh)	2014-08-21	以５員雜環為主之ｐ３８激酶抑制劑
JPH09505828A (ja)	1997-06-10	炎症治療用１，５−ジフェニルピラゾール化合物
Tsuji et al.	1997	Studies on anti-inflammatory agents. IV. Synthesis and pharmacological properties of 1, 5-diarylpyrazoles and related derivatives
EA022799B1 (ru)	2016-03-31	Пиразолилзамещенные производные угольной кислоты в качестве модуляторов рецептора простациклина (pgi2), применимые для лечения связанных с ним нарушений
KR19990063989A (ko)	1999-07-26	염증 치료용의 1,3,5-삼치환된 피라졸 화합물
MXPA00011839A (en)	2001-09-07	Pyrazoline derivatives, their preparation and application as medicaments
AU2005212833A1 (en)	2005-08-25	Pyrazoline derivatives useful for the treatment of cancer
KR840002242B1 (ko)	1984-12-07	신규 이미다졸 화합물의 제조방법
ES2325569B1 (es)	2010-03-22	Compuestos de pirazolina cicloalcanosustituidos, su preparacion y su uso como medicamentos.
HK1137992A1 (en)	2010-08-13	Sulfonylpyrazoline carboxamidine derivatives as 5-ht6 antagonists
HK1137992B (en)	2014-03-28	Sulfonylpyrazoline carboxamidine derivatives as 5-ht6 antagonists
HK1013649B (en)	2000-07-07	Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation