HRP980411A2 - Indole compounds as anti-inflammatory/analgesic agents - Google Patents
Indole compounds as anti-inflammatory/analgesic agentsInfo
- Publication number
- HRP980411A2 HRP980411A2 HRPCT/IB97/00917A HRP980411A HRP980411A2 HR P980411 A2 HRP980411 A2 HR P980411A2 HR P980411 A HRP980411 A HR P980411A HR P980411 A2 HRP980411 A2 HR P980411A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- chloro
- indole
- amino
- benzoyl
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title description 5
- 239000002260 anti-inflammatory agent Substances 0.000 title description 3
- 230000003110 anti-inflammatory effect Effects 0.000 title description 3
- 239000000730 antalgic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 429
- 238000000034 method Methods 0.000 claims description 395
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 184
- -1 SO2N(C1-4 alkyl)2 Chemical group 0.000 claims description 167
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 152
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 115
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 89
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 89
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- JQBVWECLVPFPBU-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-phenylmethanone Chemical compound N1C2=CC(Cl)=CC=C2C(N)=C1C(=O)C1=CC=CC=C1 JQBVWECLVPFPBU-UHFFFAOYSA-N 0.000 claims description 43
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 42
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 19
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- WNVKEVNNZCDMGF-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(3-chlorophenyl)methanone Chemical compound N1C2=CC(Cl)=CC=C2C(N)=C1C(=O)C1=CC=CC(Cl)=C1 WNVKEVNNZCDMGF-UHFFFAOYSA-N 0.000 claims description 15
- YMRYZSIABUBQFV-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)N)=C1 YMRYZSIABUBQFV-UHFFFAOYSA-N 0.000 claims description 15
- ZLCQCULRCSPJEA-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(4-methylpyridin-2-yl)methanone Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)N)=C1 ZLCQCULRCSPJEA-UHFFFAOYSA-N 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- KROYZOGMYPAPER-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(4-chloropyridin-2-yl)methanone Chemical compound N1C2=CC(Cl)=CC=C2C(N)=C1C(=O)C1=CC(Cl)=CC=N1 KROYZOGMYPAPER-UHFFFAOYSA-N 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 150000003180 prostaglandins Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 9
- NIGQVFUTQCFPEM-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(4-methoxypyridin-2-yl)methanone Chemical compound COC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)N)=C1 NIGQVFUTQCFPEM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- SLFRPRQBDNXBRQ-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 SLFRPRQBDNXBRQ-UHFFFAOYSA-N 0.000 claims description 8
- WZNZJPHRXPRQFH-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)propanethioamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=S)CC)=C1C(=O)C1=CC=CC=C1 WZNZJPHRXPRQFH-UHFFFAOYSA-N 0.000 claims description 8
- IGASGUVSVZVKNR-UHFFFAOYSA-N n-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC(Cl)=C1 IGASGUVSVZVKNR-UHFFFAOYSA-N 0.000 claims description 8
- KKOYCUUTXVDLTD-UHFFFAOYSA-N n-[6-chloro-2-(3-methylbenzoyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC(C)=C1 KKOYCUUTXVDLTD-UHFFFAOYSA-N 0.000 claims description 8
- GECBAXQWFZYKDC-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-pyridin-2-ylmethanone Chemical compound N1C2=CC(Cl)=CC=C2C(N)=C1C(=O)C1=CC=CC=N1 GECBAXQWFZYKDC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- RFYHKKXXJJGDEM-UHFFFAOYSA-N n-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]propanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC)=C1C(=O)C1=CC=CC(Cl)=C1 RFYHKKXXJJGDEM-UHFFFAOYSA-N 0.000 claims description 7
- FTFJXEXHTMPLKQ-UHFFFAOYSA-N n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]-2-hydroxy-2-methylpropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C(C)(O)C)=C1C(=O)C1=CC(Cl)=CC=N1 FTFJXEXHTMPLKQ-UHFFFAOYSA-N 0.000 claims description 7
- XJNHUPKQEAPVNV-UHFFFAOYSA-N n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]propanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC)=C1C(=O)C1=CC(Cl)=CC=N1 XJNHUPKQEAPVNV-UHFFFAOYSA-N 0.000 claims description 7
- IGESIALMTHTDSA-UHFFFAOYSA-N n-[6-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC(C)=CC=N1 IGESIALMTHTDSA-UHFFFAOYSA-N 0.000 claims description 7
- CIIQTVBWYYSMOR-UHFFFAOYSA-N n-[6-chloro-2-(cyclohexanecarbonyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1CCCCC1 CIIQTVBWYYSMOR-UHFFFAOYSA-N 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- ZQULDAHHZCNPSS-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-3-methylbutanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC(C)C)=C1C(=O)C1=CC=CC=C1 ZQULDAHHZCNPSS-UHFFFAOYSA-N 0.000 claims description 6
- QDQPHHCDRXHCLL-UHFFFAOYSA-N n-[6-chloro-2-[3-(hydroxymethyl)furan-2-carbonyl]-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C=1OC=CC=1CO QDQPHHCDRXHCLL-UHFFFAOYSA-N 0.000 claims description 6
- 244000052769 pathogen Species 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- HNZVPKAOOUGOTP-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(3-bromophenyl)methanone Chemical compound N1C2=CC(Cl)=CC=C2C(N)=C1C(=O)C1=CC=CC(Br)=C1 HNZVPKAOOUGOTP-UHFFFAOYSA-N 0.000 claims description 5
- XHXBBVMHBSNJNK-UHFFFAOYSA-N (3-amino-6-chloro-1h-indol-2-yl)-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)N)=C1 XHXBBVMHBSNJNK-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- GSXUABJGAFNNDE-UHFFFAOYSA-N n-(2-benzoyl-6-nitro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC([N+]([O-])=O)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 GSXUABJGAFNNDE-UHFFFAOYSA-N 0.000 claims description 5
- GCRJTJLJIWNDJP-UHFFFAOYSA-N n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC(Cl)=CC=N1 GCRJTJLJIWNDJP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 101100533890 Hypocrea jecorina (strain QM6a) sor3 gene Proteins 0.000 claims description 4
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 4
- LALRCDGZOGXDCE-UHFFFAOYSA-N [1-[[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]amino]-2-methyl-1-oxopropan-2-yl] acetate Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C(C)(C)OC(=O)C)=C1C(=O)C1=CC(Cl)=CC=N1 LALRCDGZOGXDCE-UHFFFAOYSA-N 0.000 claims description 4
- IULNKQAGAJOFDP-UHFFFAOYSA-N [6-chloro-3-(dimethylamino)-1h-indol-2-yl]-phenylmethanone Chemical compound N1C2=CC(Cl)=CC=C2C(N(C)C)=C1C(=O)C1=CC=CC=C1 IULNKQAGAJOFDP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005518 carboxamido group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- HFACYUKCVFNBJY-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-(dimethylamino)acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CN(C)C)=C1C(=O)C1=CC=CC=C1 HFACYUKCVFNBJY-UHFFFAOYSA-N 0.000 claims description 4
- SLPJUQNVHZRTDX-UHFFFAOYSA-N n-(2-benzoyl-6-cyano-1h-indol-3-yl)acetamide Chemical compound N1C2=CC(C#N)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 SLPJUQNVHZRTDX-UHFFFAOYSA-N 0.000 claims description 4
- ZQWOWEOTEUHMDE-UHFFFAOYSA-N n-(2-benzoyl-6-fluoro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC(F)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 ZQWOWEOTEUHMDE-UHFFFAOYSA-N 0.000 claims description 4
- MOTMURUCKUSSTA-UHFFFAOYSA-N n-[2-(4-aminopyridine-2-carbonyl)-6-chloro-1h-indol-3-yl]propanamide;hydrochloride Chemical compound Cl.N1C2=CC(Cl)=CC=C2C(NC(=O)CC)=C1C(=O)C1=CC(N)=CC=N1 MOTMURUCKUSSTA-UHFFFAOYSA-N 0.000 claims description 4
- ZNEKINWKDHPVKZ-UHFFFAOYSA-N n-[6-chloro-2-(3-fluorobenzoyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC(F)=C1 ZNEKINWKDHPVKZ-UHFFFAOYSA-N 0.000 claims description 4
- CZSQXCATLAFYBL-UHFFFAOYSA-N n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]-n-methylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(N(C(C)=O)C)=C1C(=O)C1=CC(Cl)=CC=N1 CZSQXCATLAFYBL-UHFFFAOYSA-N 0.000 claims description 4
- BTQAZZJOMXWIAR-UHFFFAOYSA-N n-[6-chloro-2-(pyrazine-2-carbonyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CN=CC=N1 BTQAZZJOMXWIAR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- AHOVAZJZNPBOTE-JTQLQIEISA-N (2s)-n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-hydroxypropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)[C@@H](O)C)=C1C(=O)C1=CC=CC=C1 AHOVAZJZNPBOTE-JTQLQIEISA-N 0.000 claims description 3
- OSZOBHGYASWPTR-QMMMGPOBSA-N (2s)-n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]-2-hydroxypropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)[C@@H](O)C)=C1C(=O)C1=CC(Cl)=CC=N1 OSZOBHGYASWPTR-QMMMGPOBSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- ODKXGHXBAFEWFX-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-chlorobenzamide Chemical compound C=1C=CC=CC=1C(=O)C=1NC2=CC(Cl)=CC=C2C=1NC(=O)C1=CC=CC=C1Cl ODKXGHXBAFEWFX-UHFFFAOYSA-N 0.000 claims description 3
- FRHKIJNDENAYCL-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-cyclopropylacetamide Chemical compound C=1C=CC=CC=1C(=O)C=1NC2=CC(Cl)=CC=C2C=1NC(=O)CC1CC1 FRHKIJNDENAYCL-UHFFFAOYSA-N 0.000 claims description 3
- MMJBDHCMLDLODA-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-methoxyacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)COC)=C1C(=O)C1=CC=CC=C1 MMJBDHCMLDLODA-UHFFFAOYSA-N 0.000 claims description 3
- CUIFOQRNCGUFLI-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-methoxypropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C(C)OC)=C1C(=O)C1=CC=CC=C1 CUIFOQRNCGUFLI-UHFFFAOYSA-N 0.000 claims description 3
- GWUDXYODAWOBOJ-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-2-methylpropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C(C)C)=C1C(=O)C1=CC=CC=C1 GWUDXYODAWOBOJ-UHFFFAOYSA-N 0.000 claims description 3
- ZCAWAEKOAZATKQ-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)-3,3,3-trifluoropropanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC(F)(F)F)=C1C(=O)C1=CC=CC=C1 ZCAWAEKOAZATKQ-UHFFFAOYSA-N 0.000 claims description 3
- LRAUWPWBLMJUCE-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)C=1NC2=CC(Cl)=CC=C2C=1NC(=O)C1=CC=CC=C1 LRAUWPWBLMJUCE-UHFFFAOYSA-N 0.000 claims description 3
- MKRSAXJTVTUBSA-UHFFFAOYSA-N n-(2-benzoyl-6-chloro-1h-indol-3-yl)butanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CCC)=C1C(=O)C1=CC=CC=C1 MKRSAXJTVTUBSA-UHFFFAOYSA-N 0.000 claims description 3
- YRIYWPSKQIWXMO-UHFFFAOYSA-N n-[2-(3-aminobenzoyl)-6-chloro-1h-indol-3-yl]acetamide;hydrochloride Chemical compound Cl.N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC(N)=C1 YRIYWPSKQIWXMO-UHFFFAOYSA-N 0.000 claims description 3
- VWFCWHSBOMFUHM-UHFFFAOYSA-N n-[2-(3-bromobenzoyl)-6-chloro-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC(Br)=C1 VWFCWHSBOMFUHM-UHFFFAOYSA-N 0.000 claims description 3
- IIPJCIODWYNSTR-UHFFFAOYSA-N n-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]-3-methylbutanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC(C)C)=C1C(=O)C1=CC=CC(Cl)=C1 IIPJCIODWYNSTR-UHFFFAOYSA-N 0.000 claims description 3
- WBWKGNUMLFBJEU-UHFFFAOYSA-N n-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]-n-methylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(N(C(C)=O)C)=C1C(=O)C1=CC=CC(Cl)=C1 WBWKGNUMLFBJEU-UHFFFAOYSA-N 0.000 claims description 3
- ZTELQEOBSNUTSZ-UHFFFAOYSA-N n-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]butanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CCC)=C1C(=O)C1=CC=CC(Cl)=C1 ZTELQEOBSNUTSZ-UHFFFAOYSA-N 0.000 claims description 3
- OLKZCPMPQCCNBT-UHFFFAOYSA-N n-[6-chloro-2-(3-methoxybenzoyl)-1h-indol-3-yl]acetamide Chemical compound COC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)NC(C)=O)=C1 OLKZCPMPQCCNBT-UHFFFAOYSA-N 0.000 claims description 3
- ANSMGURCLPRFKT-UHFFFAOYSA-N n-[6-chloro-2-(3-methylbenzoyl)-1h-indol-3-yl]-2-methoxyacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)COC)=C1C(=O)C1=CC=CC(C)=C1 ANSMGURCLPRFKT-UHFFFAOYSA-N 0.000 claims description 3
- GTWPFIGCEFVGKH-UHFFFAOYSA-N n-[6-chloro-2-(3-methylbenzoyl)-1h-indol-3-yl]propanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC)=C1C(=O)C1=CC=CC(C)=C1 GTWPFIGCEFVGKH-UHFFFAOYSA-N 0.000 claims description 3
- HVDZRMXHNGWJNC-UHFFFAOYSA-N n-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]-3-methylbutanamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)CC(C)C)=C1C(=O)C1=CC(Cl)=CC=N1 HVDZRMXHNGWJNC-UHFFFAOYSA-N 0.000 claims description 3
- QOUCINDCRFHMCD-UHFFFAOYSA-N n-[6-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]-3-methylbutanamide Chemical compound COC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)NC(=O)CC(C)C)=C1 QOUCINDCRFHMCD-UHFFFAOYSA-N 0.000 claims description 3
- PXNALBLRWFOUSM-UHFFFAOYSA-N n-[6-chloro-2-(pyridine-2-carbonyl)-1h-indol-3-yl]acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=N1 PXNALBLRWFOUSM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
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- QAODDCFRDDRUAH-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(3-fluorobenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(F)=C1 QAODDCFRDDRUAH-UHFFFAOYSA-N 0.000 description 2
- DNTJEFKCTFZUHN-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(3-nitrobenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC([N+]([O-])=O)=C1 DNTJEFKCTFZUHN-UHFFFAOYSA-N 0.000 description 2
- MXYVORNZVGUFAL-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(3-phenylmethoxybenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 MXYVORNZVGUFAL-UHFFFAOYSA-N 0.000 description 2
- WIEYVVHVFWBUGC-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(4-chlorobenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(Cl)C=C1 WIEYVVHVFWBUGC-UHFFFAOYSA-N 0.000 description 2
- FGDUJTICLGRILU-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(4-methoxybenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(OC)C=C1 FGDUJTICLGRILU-UHFFFAOYSA-N 0.000 description 2
- QDSQAABVOYTZSG-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(4-methylbenzoyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(C)C=C1 QDSQAABVOYTZSG-UHFFFAOYSA-N 0.000 description 2
- LXIBDRLPBAXDPZ-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(naphthalene-2-carbonyl)indole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OCC)C(C(=O)C=3C=C4C=CC=CC4=CC=3)=C(NC(C)=O)C2=C1 LXIBDRLPBAXDPZ-UHFFFAOYSA-N 0.000 description 2
- IKTUROKJPZQTET-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(pyrazine-2-carbonyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CN=CC=N1 IKTUROKJPZQTET-UHFFFAOYSA-N 0.000 description 2
- CXBGGBOZVAFLDY-UHFFFAOYSA-N ethyl 3-acetamido-6-chloro-2-(thiophene-2-carbonyl)indole-1-carboxylate Chemical compound CC(=O)NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CS1 CXBGGBOZVAFLDY-UHFFFAOYSA-N 0.000 description 2
- WPORAVZIAFFMTO-UHFFFAOYSA-N ethyl 3-amino-2-[3,4-bis(methoxymethoxy)benzoyl]-6-chloroindole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(OCOC)C(OCOC)=C1 WPORAVZIAFFMTO-UHFFFAOYSA-N 0.000 description 2
- FBIATOXKUQONAN-UHFFFAOYSA-N ethyl 3-amino-2-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridine-2-carbonyl]-6-chloroindole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(CO[Si](C)(C)C(C)(C)C)=CC=N1 FBIATOXKUQONAN-UHFFFAOYSA-N 0.000 description 2
- CSWFVUJQSCFCHA-UHFFFAOYSA-N ethyl 3-amino-2-[4-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]pyridine-2-carbonyl]-6-chloroindole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=CC=N1 CSWFVUJQSCFCHA-UHFFFAOYSA-N 0.000 description 2
- HYELZINFLNFOFP-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-4-chloroindole-1-carboxylate Chemical compound NC=1C2=C(Cl)C=CC=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 HYELZINFLNFOFP-UHFFFAOYSA-N 0.000 description 2
- IWWKBHWFXRZAJN-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-4-fluoroindole-1-carboxylate Chemical compound NC=1C2=C(F)C=CC=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 IWWKBHWFXRZAJN-UHFFFAOYSA-N 0.000 description 2
- MFLCYAMYRLIUOQ-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-5,6-dimethoxyindole-1-carboxylate Chemical compound NC=1C2=CC(OC)=C(OC)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 MFLCYAMYRLIUOQ-UHFFFAOYSA-N 0.000 description 2
- ALNOYPZXMCXZCL-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-5-bromoindole-1-carboxylate Chemical compound NC=1C2=CC(Br)=CC=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 ALNOYPZXMCXZCL-UHFFFAOYSA-N 0.000 description 2
- QNMLTAZCUMXKIZ-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-5-chloroindole-1-carboxylate Chemical compound NC=1C2=CC(Cl)=CC=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 QNMLTAZCUMXKIZ-UHFFFAOYSA-N 0.000 description 2
- AUHQHUHFMHBMCJ-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-6-(trifluoromethyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(C(F)(F)F)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 AUHQHUHFMHBMCJ-UHFFFAOYSA-N 0.000 description 2
- QGNIOHIMPGSLOS-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-6-cyanoindole-1-carboxylate Chemical compound NC=1C2=CC=C(C#N)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 QGNIOHIMPGSLOS-UHFFFAOYSA-N 0.000 description 2
- RHZZWJZJDHFGNF-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-6-fluoroindole-1-carboxylate Chemical compound NC=1C2=CC=C(F)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 RHZZWJZJDHFGNF-UHFFFAOYSA-N 0.000 description 2
- DZMIIJZUEVTUTN-UHFFFAOYSA-N ethyl 3-amino-2-benzoyl-6-methylindole-1-carboxylate Chemical compound NC=1C2=CC=C(C)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC=C1 DZMIIJZUEVTUTN-UHFFFAOYSA-N 0.000 description 2
- OUVNYMQUIKMUFG-UHFFFAOYSA-N ethyl 3-amino-5-chloro-2-(3-chlorobenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC(Cl)=CC=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(Cl)=C1 OUVNYMQUIKMUFG-UHFFFAOYSA-N 0.000 description 2
- WNHQIWREZDZHJQ-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(2,2-dimethylpropanoyl)indole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OCC)C(C(=O)C(C)(C)C)=C(N)C2=C1 WNHQIWREZDZHJQ-UHFFFAOYSA-N 0.000 description 2
- PAPVKLTXIONJHW-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3,5-difluorobenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(F)=CC(F)=C1 PAPVKLTXIONJHW-UHFFFAOYSA-N 0.000 description 2
- NWBDVQOFKYIJLM-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-cyanobenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(C#N)=C1 NWBDVQOFKYIJLM-UHFFFAOYSA-N 0.000 description 2
- SNHUKZOQHCQWKQ-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-methylbenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(C)=C1 SNHUKZOQHCQWKQ-UHFFFAOYSA-N 0.000 description 2
- XBHZTNRHIHKJSG-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-methylcyclohexanecarbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1CCCC(C)C1 XBHZTNRHIHKJSG-UHFFFAOYSA-N 0.000 description 2
- HCVUKMDVEKQWBF-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-methylpyridine-2-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=NC=CC=C1C HCVUKMDVEKQWBF-UHFFFAOYSA-N 0.000 description 2
- UUYWMONZOOHSFB-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-nitrobenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC([N+]([O-])=O)=C1 UUYWMONZOOHSFB-UHFFFAOYSA-N 0.000 description 2
- NHODUMCAGDDSMD-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-phenylmethoxybenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 NHODUMCAGDDSMD-UHFFFAOYSA-N 0.000 description 2
- SLPITGBWDKODJO-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(3-sulfamoylbenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(S(N)(=O)=O)=C1 SLPITGBWDKODJO-UHFFFAOYSA-N 0.000 description 2
- PFBBQMPVIJDGAJ-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(4-chloro-3-methylbenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(Cl)C(C)=C1 PFBBQMPVIJDGAJ-UHFFFAOYSA-N 0.000 description 2
- MOAJYYQCJKGMKW-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(4-methoxybenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(OC)C=C1 MOAJYYQCJKGMKW-UHFFFAOYSA-N 0.000 description 2
- CKAMREMCGJPLMC-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(4-methoxypyridine-2-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(OC)=CC=N1 CKAMREMCGJPLMC-UHFFFAOYSA-N 0.000 description 2
- IOXCNGWXHXZYPO-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(4-methylbenzenecarbothioyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=S)C1=CC=C(C)C=C1 IOXCNGWXHXZYPO-UHFFFAOYSA-N 0.000 description 2
- VXMFGDBRPMVVPS-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(4-methylpyridine-2-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(C)=CC=N1 VXMFGDBRPMVVPS-UHFFFAOYSA-N 0.000 description 2
- PNVMTMLCHXTVOH-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(5-chloro-2-nitrobenzoyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O PNVMTMLCHXTVOH-UHFFFAOYSA-N 0.000 description 2
- KHARKJIFQFIAGI-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(cyclohexanecarbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1CCCCC1 KHARKJIFQFIAGI-UHFFFAOYSA-N 0.000 description 2
- JKKBXKHVFTXUOP-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(furan-3-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C=1C=COC=1 JKKBXKHVFTXUOP-UHFFFAOYSA-N 0.000 description 2
- AJDDWOIOELZYPT-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(naphthalene-2-carbonyl)indole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OCC)C(C(=O)C=3C=C4C=CC=CC4=CC=3)=C(N)C2=C1 AJDDWOIOELZYPT-UHFFFAOYSA-N 0.000 description 2
- POGYKNGBGZLPDA-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(pyrazine-2-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CN=CC=N1 POGYKNGBGZLPDA-UHFFFAOYSA-N 0.000 description 2
- USWLUKWHBKGABZ-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(pyridine-3-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CN=C1 USWLUKWHBKGABZ-UHFFFAOYSA-N 0.000 description 2
- KFVNXLAGRPXFLR-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(pyridine-4-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=NC=C1 KFVNXLAGRPXFLR-UHFFFAOYSA-N 0.000 description 2
- SWOAHMUJVRVHIW-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-(thiophene-2-carbonyl)indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CS1 SWOAHMUJVRVHIW-UHFFFAOYSA-N 0.000 description 2
- ROXXIGIRCACYCO-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-[3-(hydroxymethyl)furan-2-carbonyl]indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C=1OC=CC=1CO ROXXIGIRCACYCO-UHFFFAOYSA-N 0.000 description 2
- KTAJGLPHBRJDBX-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-[3-(trifluoromethyl)benzoyl]indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=CC(C(F)(F)F)=C1 KTAJGLPHBRJDBX-UHFFFAOYSA-N 0.000 description 2
- MPJKOCXCAPOQOH-UHFFFAOYSA-N ethyl 3-amino-6-chloro-2-[4-(trifluoromethoxy)benzoyl]indole-1-carboxylate Chemical compound NC=1C2=CC=C(Cl)C=C2N(C(=O)OCC)C=1C(=O)C1=CC=C(OC(F)(F)F)C=C1 MPJKOCXCAPOQOH-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- ZJLZJOYMOMMKHQ-UHFFFAOYSA-N ethyl n-(2,5-dicyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC(C#N)=CC=C1C#N ZJLZJOYMOMMKHQ-UHFFFAOYSA-N 0.000 description 2
- TYJWLNZNZHOOTM-UHFFFAOYSA-N ethyl n-(2-cyano-4,5-dimethoxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC(OC)=C(OC)C=C1C#N TYJWLNZNZHOOTM-UHFFFAOYSA-N 0.000 description 2
- TXXZIBHQWMGCQB-UHFFFAOYSA-N ethyl n-(2-cyano-4-fluorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(F)C=C1C#N TXXZIBHQWMGCQB-UHFFFAOYSA-N 0.000 description 2
- HQRQPTJXKPOXCO-UHFFFAOYSA-N ethyl n-(2-cyano-5-fluorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC(F)=CC=C1C#N HQRQPTJXKPOXCO-UHFFFAOYSA-N 0.000 description 2
- WIXDOFZRIGCVAB-UHFFFAOYSA-N ethyl n-(2-cyano-5-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC(C)=CC=C1C#N WIXDOFZRIGCVAB-UHFFFAOYSA-N 0.000 description 2
- BPHFPNNTTCTGEK-UHFFFAOYSA-N ethyl n-(2-cyano-5-nitrophenyl)carbamate Chemical compound CCOC(=O)NC1=CC([N+]([O-])=O)=CC=C1C#N BPHFPNNTTCTGEK-UHFFFAOYSA-N 0.000 description 2
- PCFFUYNDZRZDOP-UHFFFAOYSA-N ethyl n-(3-chloro-2-cyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(Cl)=C1C#N PCFFUYNDZRZDOP-UHFFFAOYSA-N 0.000 description 2
- NQFAHYWFJMMSLF-UHFFFAOYSA-N ethyl n-(4-bromo-2-cyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Br)C=C1C#N NQFAHYWFJMMSLF-UHFFFAOYSA-N 0.000 description 2
- XCMLPBNNBDPVDU-UHFFFAOYSA-N ethyl n-(4-chloro-2-cyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1C#N XCMLPBNNBDPVDU-UHFFFAOYSA-N 0.000 description 2
- INGPQTQDYHWDER-UHFFFAOYSA-N ethyl n-[2-cyano-5-(trifluoromethyl)phenyl]carbamate Chemical compound CCOC(=O)NC1=CC(C(F)(F)F)=CC=C1C#N INGPQTQDYHWDER-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- AAZISYQLZVRBEU-UHFFFAOYSA-N methyl 3-(3-amino-6-chloro-1h-indole-2-carbonyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)N)=C1 AAZISYQLZVRBEU-UHFFFAOYSA-N 0.000 description 2
- LDXATYQUMWAZBN-UHFFFAOYSA-N methyl 6-methoxy-3-nitro-1h-indole-2-carboxylate Chemical compound COC1=CC=C2C([N+]([O-])=O)=C(C(=O)OC)NC2=C1 LDXATYQUMWAZBN-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- YHUWRCXFDAITEK-UHFFFAOYSA-N n,5-dimethoxy-n-methyl-3-nitro-1h-indole-2-carboxamide Chemical compound C1=C(OC)C=C2C([N+]([O-])=O)=C(C(=O)N(C)OC)NC2=C1 YHUWRCXFDAITEK-UHFFFAOYSA-N 0.000 description 2
- DWOPLHLZQMOPBU-UHFFFAOYSA-N n-(2-benzoyl-1h-indol-3-yl)acetamide Chemical compound N1C2=CC=CC=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 DWOPLHLZQMOPBU-UHFFFAOYSA-N 0.000 description 2
- DZTKDVZFZQVHQO-UHFFFAOYSA-N n-(2-benzoyl-4-chloro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC=CC(Cl)=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 DZTKDVZFZQVHQO-UHFFFAOYSA-N 0.000 description 2
- UNEJCZHZTDHCHR-UHFFFAOYSA-N n-(2-benzoyl-4-fluoro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC=CC(F)=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 UNEJCZHZTDHCHR-UHFFFAOYSA-N 0.000 description 2
- WWHMRNXGIVFLNT-UHFFFAOYSA-N n-(2-benzoyl-5,6-dimethoxy-1h-indol-3-yl)acetamide Chemical compound CC(=O)NC=1C=2C=C(OC)C(OC)=CC=2NC=1C(=O)C1=CC=CC=C1 WWHMRNXGIVFLNT-UHFFFAOYSA-N 0.000 description 2
- YRPWSYDGSIFYCX-UHFFFAOYSA-N n-(2-benzoyl-5-bromo-1h-indol-3-yl)acetamide Chemical compound N1C2=CC=C(Br)C=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 YRPWSYDGSIFYCX-UHFFFAOYSA-N 0.000 description 2
- KLJURXLENZIMHP-UHFFFAOYSA-N n-(2-benzoyl-5-chloro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC=C(Cl)C=C2C(NC(=O)C)=C1C(=O)C1=CC=CC=C1 KLJURXLENZIMHP-UHFFFAOYSA-N 0.000 description 2
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
- 229960003676 tenidap Drugs 0.000 description 1
- 229950009638 tepoxalin Drugs 0.000 description 1
- XYKWNRUXCOIMFZ-UHFFFAOYSA-N tepoxalin Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CCC(=O)N(C)O)=N1 XYKWNRUXCOIMFZ-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 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
- 208000004371 toothache Diseases 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IB9700917 | 1997-07-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP980411A2 true HRP980411A2 (en) | 1999-04-30 |
Family
ID=11004592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRPCT/IB97/00917A HRP980411A2 (en) | 1997-07-23 | 1998-07-22 | Indole compounds as anti-inflammatory/analgesic agents |
Country Status (19)
Country | Link |
---|---|
US (1) | US6300363B1 (ja) |
EP (1) | EP1001934B1 (ja) |
JP (1) | JP3267635B2 (ja) |
AP (1) | AP9801302A0 (ja) |
AR (1) | AR016523A1 (ja) |
AT (1) | ATE228503T1 (ja) |
AU (1) | AU8030598A (ja) |
BR (2) | BR9811533A (ja) |
CA (1) | CA2295063C (ja) |
CO (1) | CO4810382A1 (ja) |
DE (1) | DE69809758T2 (ja) |
DK (1) | DK1001934T3 (ja) |
ES (1) | ES2184280T3 (ja) |
HR (1) | HRP980411A2 (ja) |
MA (1) | MA26526A1 (ja) |
PA (1) | PA8456101A1 (ja) |
PT (1) | PT1001934E (ja) |
TN (1) | TNSN98140A1 (ja) |
WO (1) | WO1999005104A1 (ja) |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
FR2774097B1 (fr) * | 1998-01-28 | 2000-09-29 | Bio Merieux | Utilisation de derives d'indolamine dans la detection d'une activite de peptidase ou dans la detection de micro-organismes |
US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
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WO1997013767A1 (de) * | 1995-10-09 | 1997-04-17 | Chemisch Pharmazeutische Forschungsgesellschaft Mbh | Heterocyclisch substituierte 1-indolcarboxamide als cyclooxygenase-2 inhibitoren |
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Also Published As
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ATE228503T1 (de) | 2002-12-15 |
AP9801302A0 (en) | 2000-01-23 |
WO1999005104A1 (en) | 1999-02-04 |
ES2184280T3 (es) | 2003-04-01 |
AU8030598A (en) | 1999-02-16 |
CO4810382A1 (es) | 1999-06-30 |
EP1001934A1 (en) | 2000-05-24 |
CA2295063C (en) | 2005-10-18 |
EP1001934B1 (en) | 2002-11-27 |
US6300363B1 (en) | 2001-10-09 |
DE69809758T2 (de) | 2003-04-10 |
BR9812095A (pt) | 2000-07-18 |
DE69809758D1 (de) | 2003-01-09 |
CA2295063A1 (en) | 1999-02-04 |
TNSN98140A1 (fr) | 2005-03-15 |
BR9811533A (pt) | 2000-08-29 |
PA8456101A1 (es) | 2000-05-24 |
PT1001934E (pt) | 2003-02-28 |
JP2000513386A (ja) | 2000-10-10 |
JP3267635B2 (ja) | 2002-03-18 |
DK1001934T3 (da) | 2002-12-30 |
AR016523A1 (es) | 2001-07-25 |
MA26526A1 (fr) | 2004-12-20 |
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