HRP20000061A2 - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- HRP20000061A2 HRP20000061A2 HR20000061A HRP20000061A HRP20000061A2 HR P20000061 A2 HRP20000061 A2 HR P20000061A2 HR 20000061 A HR20000061 A HR 20000061A HR P20000061 A HRP20000061 A HR P20000061A HR P20000061 A2 HRP20000061 A2 HR P20000061A2
- Authority
- HR
- Croatia
- Prior art keywords
- dichlorobenzyl
- carboxylic acid
- indole
- 4alkyl
- yield
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 118
- 150000002148 esters Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 101710155857 C-C motif chemokine 2 Proteins 0.000 claims abstract description 33
- 238000001727 in vivo Methods 0.000 claims abstract description 26
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
- -1 carboxy, trifluoromethoxy, amino Chemical group 0.000 claims description 84
- 102100021943 C-C motif chemokine 2 Human genes 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- KXPXBRFMJIIDDD-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-3-methylindole-2-carboxylic acid Chemical compound C12=CC=CC=C2C(C)=C(C(O)=O)N1CC1=CC=C(Cl)C(Cl)=C1 KXPXBRFMJIIDDD-UHFFFAOYSA-N 0.000 claims description 2
- RYKBAXLGJFVKHU-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-fluoroindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(F)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 RYKBAXLGJFVKHU-UHFFFAOYSA-N 0.000 claims description 2
- CWBFXLNEPCROQA-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-hydroxyindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(O)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 CWBFXLNEPCROQA-UHFFFAOYSA-N 0.000 claims description 2
- XXZFOOVRCMARER-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-methoxyindole-2-carboxylic acid Chemical compound OC(=O)C1=CC=2C(OC)=CC=CC=2N1CC1=CC=C(Cl)C(Cl)=C1 XXZFOOVRCMARER-UHFFFAOYSA-N 0.000 claims description 2
- BQWSAQCYWUJROX-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-pyridin-2-ylindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=3N=CC=CC=3)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 BQWSAQCYWUJROX-UHFFFAOYSA-N 0.000 claims description 2
- KWJQWINCFFDBNF-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-pyridin-3-ylindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=3C=NC=CC=3)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 KWJQWINCFFDBNF-UHFFFAOYSA-N 0.000 claims description 2
- BYIIVVGXHIJYPS-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-thiophen-2-ylindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C=3SC=CC=3)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 BYIIVVGXHIJYPS-UHFFFAOYSA-N 0.000 claims description 2
- ZDVIRSPTOFRFBN-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-thiophen-3-ylindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(C3=CSC=C3)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 ZDVIRSPTOFRFBN-UHFFFAOYSA-N 0.000 claims description 2
- DQKTXPJNUGHTLY-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-(trifluoromethyl)indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 DQKTXPJNUGHTLY-UHFFFAOYSA-N 0.000 claims description 2
- JXQJWMUSDDUYOB-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methylindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(C)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 JXQJWMUSDDUYOB-UHFFFAOYSA-N 0.000 claims description 2
- YTXZWIOUWVRTFN-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-nitroindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC([N+]([O-])=O)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 YTXZWIOUWVRTFN-UHFFFAOYSA-N 0.000 claims description 2
- LOJNFRIYBAPNOH-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-6-fluoroindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(F)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 LOJNFRIYBAPNOH-UHFFFAOYSA-N 0.000 claims description 2
- KTEPDNJLCVLUTQ-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]indole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC2=CC(C(O)=O)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 KTEPDNJLCVLUTQ-UHFFFAOYSA-N 0.000 claims description 2
- SRWGFNIPGKCMQA-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-5-nitroindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC([N+]([O-])=O)=CC=C2N1CC1=CC=CC(Cl)=C1 SRWGFNIPGKCMQA-UHFFFAOYSA-N 0.000 claims description 2
- OCJIWGUXLOMFIS-UHFFFAOYSA-N 1-[(3-methylphenyl)methyl]-5-nitroindole-2-carboxylic acid Chemical compound CC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(O)=O)[N+]([O-])=O)=C1 OCJIWGUXLOMFIS-UHFFFAOYSA-N 0.000 claims description 2
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- IKONQGMYCPSPSH-CHWSQXEVSA-N 3-[(1r,2r)-2-carboxycyclopropyl]-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C(C1=CC=CC=C11)=C(C(O)=O)N1CC1=CC=C(Cl)C(Cl)=C1 IKONQGMYCPSPSH-CHWSQXEVSA-N 0.000 claims description 2
- SCTGCTBYVQQMFM-UHFFFAOYSA-N 3-bromo-1-[[3-(trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=C(Br)C2=CC=CC=C2N1CC1=CC=CC(C(F)(F)F)=C1 SCTGCTBYVQQMFM-UHFFFAOYSA-N 0.000 claims description 2
- MBRUEOFHPTUYJT-UHFFFAOYSA-N 3-bromo-5-chloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=C(Br)C2=CC(Cl)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 MBRUEOFHPTUYJT-UHFFFAOYSA-N 0.000 claims description 2
- GUJYRNHDMZPGLT-UHFFFAOYSA-N 3-chloro-1-[(3,4-dichlorophenyl)methyl]-5-fluoroindole-2-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C2=CC(F)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 GUJYRNHDMZPGLT-UHFFFAOYSA-N 0.000 claims description 2
- YENBKZUDSJSMQP-UHFFFAOYSA-N 4-(3-aminophenyl)-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound NC1=CC=CC(C=2C=3C=C(N(CC=4C=C(Cl)C(Cl)=CC=4)C=3C=CC=2)C(O)=O)=C1 YENBKZUDSJSMQP-UHFFFAOYSA-N 0.000 claims description 2
- XDWPMAKSOJITSN-UHFFFAOYSA-N 4-amino-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC=2C(N)=CC=CC=2N1CC1=CC=C(Cl)C(Cl)=C1 XDWPMAKSOJITSN-UHFFFAOYSA-N 0.000 claims description 2
- UFJKKGHGPPWTHG-UHFFFAOYSA-N 4-chloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=C(Cl)C=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 UFJKKGHGPPWTHG-UHFFFAOYSA-N 0.000 claims description 2
- LYVPVEATWGJOFE-UHFFFAOYSA-N 5,6-dichloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Cl)=C(Cl)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 LYVPVEATWGJOFE-UHFFFAOYSA-N 0.000 claims description 2
- ASHZLURJHGQWMH-UHFFFAOYSA-N 5-chloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(Cl)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 ASHZLURJHGQWMH-UHFFFAOYSA-N 0.000 claims description 2
- SWKGEPRFDNMDQY-UHFFFAOYSA-N 5-fluoro-1-[[3-(trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(C(F)(F)F)=C1 SWKGEPRFDNMDQY-UHFFFAOYSA-N 0.000 claims description 2
- IGGSLGJRSFUOBF-UHFFFAOYSA-N 5-nitro-1-[[3-(trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC([N+]([O-])=O)=CC=C2N1CC1=CC=CC(C(F)(F)F)=C1 IGGSLGJRSFUOBF-UHFFFAOYSA-N 0.000 claims description 2
- CFZWZOOHTJWCPX-UHFFFAOYSA-N 6-chloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(Cl)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 CFZWZOOHTJWCPX-UHFFFAOYSA-N 0.000 claims description 2
- AFMCXACOGDPOND-UHFFFAOYSA-N 6-fluoro-1-[[3-(trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=C(F)C=C2N1CC1=CC=CC(C(F)(F)F)=C1 AFMCXACOGDPOND-UHFFFAOYSA-N 0.000 claims description 2
- FWUBYIZVKVARPD-UHFFFAOYSA-N 7-chloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC(Cl)=C2N1CC1=CC=C(Cl)C(Cl)=C1 FWUBYIZVKVARPD-UHFFFAOYSA-N 0.000 claims description 2
- 206010001889 Alveolitis Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 206010040914 Skin reaction Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 2
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 2
- 230000035483 skin reaction Effects 0.000 claims description 2
- 231100000430 skin reaction Toxicity 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- BFIFONQPMYJRRC-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-7-fluoroindole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC(F)=C2N1CC1=CC=C(Cl)C(Cl)=C1 BFIFONQPMYJRRC-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 230000005951 type IV hypersensitivity Effects 0.000 claims 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 102000000018 Chemokine CCL2 Human genes 0.000 abstract 2
- 238000000034 method Methods 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 37
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- 230000002349 favourable effect Effects 0.000 description 29
- 239000007787 solid Substances 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012467 final product Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 102000004497 CCR2 Receptors Human genes 0.000 description 7
- 108010017312 CCR2 Receptors Proteins 0.000 description 7
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- INZPNADHWWBTHZ-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-5-[4-(dimethylamino)phenyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC(C=3C=CC(=CC=3)N(C)C)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 INZPNADHWWBTHZ-UHFFFAOYSA-N 0.000 description 1
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- SVPFOOIQVJJVEU-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-5-thiophen-2-ylindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC(C=3SC=CC=3)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 SVPFOOIQVJJVEU-UHFFFAOYSA-N 0.000 description 1
- FNDLAZGAEKXVCD-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-6-(trifluoromethyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=C(C(F)(F)F)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 FNDLAZGAEKXVCD-UHFFFAOYSA-N 0.000 description 1
- JRPXWIDMHKZQLN-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-6-fluoroindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=C(F)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 JRPXWIDMHKZQLN-UHFFFAOYSA-N 0.000 description 1
- PDBZBJAVNLZGII-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-6-nitroindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=C([N+]([O-])=O)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 PDBZBJAVNLZGII-UHFFFAOYSA-N 0.000 description 1
- GZRACXFFZSZHHX-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-6-thiophen-2-ylindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=C(C=3SC=CC=3)C=C2N1CC1=CC=C(Cl)C(Cl)=C1 GZRACXFFZSZHHX-UHFFFAOYSA-N 0.000 description 1
- ZTDUXVSBRQFEIH-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-7-(trifluoromethyl)indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC(C(F)(F)F)=C2N1CC1=CC=C(Cl)C(Cl)=C1 ZTDUXVSBRQFEIH-UHFFFAOYSA-N 0.000 description 1
- APJCRLKAIAVSNY-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-7-fluoroindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC(F)=C2N1CC1=CC=C(Cl)C(Cl)=C1 APJCRLKAIAVSNY-UHFFFAOYSA-N 0.000 description 1
- HJMJAHOWAAEAMV-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-7-methoxyindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC(OC)=C2N1CC1=CC=C(Cl)C(Cl)=C1 HJMJAHOWAAEAMV-UHFFFAOYSA-N 0.000 description 1
- JTMLBLAWBSQOCR-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]-7-methylindole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC(C)=C2N1CC1=CC=C(Cl)C(Cl)=C1 JTMLBLAWBSQOCR-UHFFFAOYSA-N 0.000 description 1
- PZIJQOVUEZJAGC-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 PZIJQOVUEZJAGC-UHFFFAOYSA-N 0.000 description 1
- SNFBFLWZUXLNOB-UHFFFAOYSA-N ethyl 1-[(4-chlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CC=CC=C2N1CC1=CC=C(Cl)C=C1 SNFBFLWZUXLNOB-UHFFFAOYSA-N 0.000 description 1
- GLSYARFJOAOUKJ-UHFFFAOYSA-N ethyl 2-[(4-bromophenyl)hydrazinylidene]propanoate Chemical compound CCOC(=O)C(C)=NNC1=CC=C(Br)C=C1 GLSYARFJOAOUKJ-UHFFFAOYSA-N 0.000 description 1
- JQQPLSWOCXGGJE-UHFFFAOYSA-N ethyl 3-acetyl-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=C(C(C)=O)C2=CC=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 JQQPLSWOCXGGJE-UHFFFAOYSA-N 0.000 description 1
- NEVIDQDHDQCAAT-UHFFFAOYSA-N ethyl 3-amino-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=C(N)C2=CC=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 NEVIDQDHDQCAAT-UHFFFAOYSA-N 0.000 description 1
- MBPGDUZEBODBNA-UHFFFAOYSA-N ethyl 3-bromo-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=C(Br)C2=CC=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 MBPGDUZEBODBNA-UHFFFAOYSA-N 0.000 description 1
- SVEJMAGNQFGKBJ-UHFFFAOYSA-N ethyl 3-chloro-1-[(3,4-dichlorophenyl)methyl]-5-fluoroindole-2-carboxylate Chemical compound CCOC(=O)C1=C(Cl)C2=CC(F)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 SVEJMAGNQFGKBJ-UHFFFAOYSA-N 0.000 description 1
- UHTMDXSOGQARCU-UHFFFAOYSA-N ethyl 3-formyl-1h-indole-2-carboxylate Chemical compound C1=CC=C2C(C=O)=C(C(=O)OCC)NC2=C1 UHTMDXSOGQARCU-UHFFFAOYSA-N 0.000 description 1
- OFZCLHMMWHJZCX-UHFFFAOYSA-N ethyl 4,5-dichloro-1-[(3,4-dichlorophenyl)methyl]indole-2-carboxylate Chemical compound CCOC(=O)C1=CC2=C(Cl)C(Cl)=CC=C2N1CC1=CC=C(Cl)C(Cl)=C1 OFZCLHMMWHJZCX-UHFFFAOYSA-N 0.000 description 1
- PISLFLJLHWFZPG-UHFFFAOYSA-N ethyl 4,5-dichloro-1h-indole-2-carboxylate Chemical compound ClC1=CC=C2NC(C(=O)OCC)=CC2=C1Cl PISLFLJLHWFZPG-UHFFFAOYSA-N 0.000 description 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229950000550 sodium metrizoate Drugs 0.000 description 1
- WINYCIXPFGVTOS-UHFFFAOYSA-M sodium;dichloromethane;hydroxide Chemical compound [OH-].[Na+].ClCCl WINYCIXPFGVTOS-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
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- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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Classifications
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- 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
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- 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
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
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- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Toxicology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- External Artificial Organs (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9716657.3A GB9716657D0 (en) | 1997-08-07 | 1997-08-07 | Chemical compounds |
PCT/GB1998/002341 WO1999007351A2 (en) | 1997-08-07 | 1998-08-04 | Indole derivatives and their use as mcp-1 antagonists |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000061A2 true HRP20000061A2 (en) | 2000-12-31 |
Family
ID=10817097
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000061A HRP20000061A2 (en) | 1997-08-07 | 2000-02-03 | Chemical compounds |
Country Status (28)
Country | Link |
---|---|
US (2) | US6441004B1 (ja) |
EP (1) | EP1003504B1 (ja) |
JP (1) | JP3863722B2 (ja) |
KR (1) | KR20010022318A (ja) |
CN (1) | CN1265591A (ja) |
AT (1) | ATE244007T1 (ja) |
AU (1) | AU745907C (ja) |
BR (1) | BR9811818A (ja) |
CA (1) | CA2297290A1 (ja) |
CZ (1) | CZ294600B6 (ja) |
DE (1) | DE69816091T2 (ja) |
DK (1) | DK1003504T3 (ja) |
ES (1) | ES2201517T3 (ja) |
GB (1) | GB9716657D0 (ja) |
HK (1) | HK1027979A1 (ja) |
HR (1) | HRP20000061A2 (ja) |
HU (1) | HUP0004301A3 (ja) |
ID (1) | ID23666A (ja) |
IL (1) | IL133989A0 (ja) |
NO (1) | NO20000573L (ja) |
NZ (1) | NZ502056A (ja) |
PL (1) | PL338948A1 (ja) |
PT (1) | PT1003504E (ja) |
RU (1) | RU2217142C2 (ja) |
SK (1) | SK284408B6 (ja) |
TR (1) | TR200000289T2 (ja) |
WO (1) | WO1999007351A2 (ja) |
ZA (1) | ZA987090B (ja) |
Families Citing this family (102)
Publication number | Priority date | Publication date | Assignee | Title |
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GB9716657D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
FR2768146B1 (fr) | 1997-09-05 | 2000-05-05 | Oreal | Nouveaux composes de la famille des indole-carboxyliques et leur utilisation |
GB9902452D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
GB9902453D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
GB9902459D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
FR2796274B1 (fr) | 1999-07-16 | 2001-09-21 | Oreal | Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses derives pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
FR2796279B1 (fr) * | 1999-07-16 | 2001-09-21 | Oreal | Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses derives pour le traitement de la seborrhee |
GB0000625D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
GB0000626D0 (en) * | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
CA2427499A1 (en) | 2000-10-10 | 2002-04-18 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppar-.gamma. binding agents |
HUP0303540A2 (hu) | 2000-12-20 | 2004-01-28 | Bristol-Myers Squibb Pharma Co. | Diaminok mint kemokin receptor aktivitás modulátorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk |
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JP2004529113A (ja) | 2001-03-07 | 2004-09-24 | ファイザー・プロダクツ・インク | ケモカイン受容体活性のモジュレーター |
ES2180436B1 (es) * | 2001-06-04 | 2003-11-01 | Menarini Lab | Nuevos indoles como inhibidores de la ciclooxigenasa- ii |
EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
US7842693B2 (en) | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
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TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
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US7291615B2 (en) | 2003-05-01 | 2007-11-06 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
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US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
WO2004108671A1 (en) * | 2003-06-06 | 2004-12-16 | Suven Life Sciences Limited | Substituted indoles with serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them |
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US7332521B2 (en) * | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
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JP2008502672A (ja) * | 2004-06-18 | 2008-01-31 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
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