ZA200204313B - Substituted pyrroles. - Google Patents

Substituted pyrroles. Download PDF

Info

Publication number: ZA200204313B
Authority: ZA; South Africa
Prior art keywords: methyl; indol; dione; pyrrole; compound
Prior art date: 1999-12-22

Application number

ZA200204313A

Other languages

English (en)

Inventor

Nader Fotouhi

Allen John Lovey

Norman Kong

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-12-22

Filing date

2002-05-29

Publication date

2003-08-29

2002-05-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2003-08-29 Publication of ZA200204313B publication Critical patent/ZA200204313B/en

Links

150000003233 pyrroles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 138
239000000203 mixture Substances 0.000 claims description 78
125000001072 heteroaryl group Chemical group 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
-1 4-methyl-piperazinyl Chemical group 0.000 claims description 23
125000000623 heterocyclic group Chemical group 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
206010028980 Neoplasm Diseases 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
230000002062 proliferating effect Effects 0.000 claims description 6
208000026310 Breast neoplasm Diseases 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
210000000481 breast Anatomy 0.000 claims description 4
208000029742 colonic neoplasm Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
238000007911 parenteral administration Methods 0.000 claims description 4
ZYOFIWUHGDZZLH-UHFFFAOYSA-N 3-(6-fluoro-1-methylindol-3-yl)-4-[1-(methoxymethyl)-6-morpholin-4-ylindol-3-yl]pyrrole-2,5-dione Chemical compound C1=C2N(COC)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(F)C=C4N(C)C=3)=O)C2=CC=C1N1CCOCC1 ZYOFIWUHGDZZLH-UHFFFAOYSA-N 0.000 claims description 3
RVRCOUNANDNKAY-UHFFFAOYSA-N 3-(6-imidazol-1-yl-1-methylindol-3-yl)-4-(1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1C=CN=C1 RVRCOUNANDNKAY-UHFFFAOYSA-N 0.000 claims description 3
AEHXCTILZYPQFS-UHFFFAOYSA-N 3-[1-methyl-6-(3-methylimidazol-4-yl)indol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound CN1C=NC=C1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=C1 AEHXCTILZYPQFS-UHFFFAOYSA-N 0.000 claims description 3
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
GSBJOANVGDUKKJ-UHFFFAOYSA-N 3-(1,6-dimethylindol-3-yl)-4-(1-methyl-6-morpholin-4-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C=1N(C)C2=CC(C)=CC=C2C=1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCOCC1 GSBJOANVGDUKKJ-UHFFFAOYSA-N 0.000 claims description 2
WITWKVIMLCAJQR-UHFFFAOYSA-N 3-(1-methyl-6-morpholin-4-ylindol-3-yl)-4-[1-methyl-6-(trifluoromethyl)indol-3-yl]pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)C(F)(F)F)=O)C2=CC=C1N1CCOCC1 WITWKVIMLCAJQR-UHFFFAOYSA-N 0.000 claims description 2
BPNSPYCPVJVODA-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-(1-methyl-6-pyrimidin-5-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C1=CN=CN=C1 BPNSPYCPVJVODA-UHFFFAOYSA-N 0.000 claims description 2
NPJSJJUPHNDSDD-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-(1-methyl-6-thiophen-3-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C=1C=CSC=1 NPJSJJUPHNDSDD-UHFFFAOYSA-N 0.000 claims description 2
RGUSQOZALWZFAV-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-(6-pyrrolidin-1-yl-1h-indol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C([N+]([O-])=O)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CNC1=CC=2N1CCCC1 RGUSQOZALWZFAV-UHFFFAOYSA-N 0.000 claims description 2
RFRLRQNXXGQSSL-UHFFFAOYSA-N 3-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)-4-[1-methyl-6-(trifluoromethyl)indol-3-yl]pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)C(F)(F)F)=O)C2=CC=C1N1CCCC1 RFRLRQNXXGQSSL-UHFFFAOYSA-N 0.000 claims description 2
FLFDOBUXLXSAHF-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-morpholin-4-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCOCC1 FLFDOBUXLXSAHF-UHFFFAOYSA-N 0.000 claims description 2
QONSDUUWOCNFSS-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-pyrazol-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1C=CC=N1 QONSDUUWOCNFSS-UHFFFAOYSA-N 0.000 claims description 2
PLFPRBVJUXUKKJ-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-pyrimidin-5-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2C1=CN=CN=C1 PLFPRBVJUXUKKJ-UHFFFAOYSA-N 0.000 claims description 2
DWVDKQLCWKXKMC-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-thiophen-2-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2C1=CC=CS1 DWVDKQLCWKXKMC-UHFFFAOYSA-N 0.000 claims description 2
IWEOQHZWEROYAN-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[1-methyl-6-(1,2-thiazol-5-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2C1=CC=NS1 IWEOQHZWEROYAN-UHFFFAOYSA-N 0.000 claims description 2
WYYFXECNAYYYQK-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[1-methyl-6-(1-methylimidazol-2-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound CN1C=CN=C1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=CC=C4N(C)C=3)=O)C2=C1 WYYFXECNAYYYQK-UHFFFAOYSA-N 0.000 claims description 2
WCNHHJWNTLCTMV-UHFFFAOYSA-N 3-(1h-indol-3-yl)-4-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=CC=C4NC=3)=O)C2=CC=C1N1CCCC1 WCNHHJWNTLCTMV-UHFFFAOYSA-N 0.000 claims description 2
ZRDBJWGXBIUKMV-UHFFFAOYSA-N 3-(6-bromo-1-methylindol-3-yl)-4-(1-methyl-6-morpholin-4-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Br)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCOCC1 ZRDBJWGXBIUKMV-UHFFFAOYSA-N 0.000 claims description 2
HYPVYVYASYZTBQ-UHFFFAOYSA-N 3-(6-chloro-1-methylindol-3-yl)-4-(6-pyrrolidin-1-yl-1h-indol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Cl)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CNC1=CC=2N1CCCC1 HYPVYVYASYZTBQ-UHFFFAOYSA-N 0.000 claims description 2
WPLMOTDWUIFINF-UHFFFAOYSA-N 3-(6-imidazol-1-yl-1-methylindol-3-yl)-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1N1C=CN=C1 WPLMOTDWUIFINF-UHFFFAOYSA-N 0.000 claims description 2
HSKQEYPXKXWWNI-UHFFFAOYSA-N 3-(6-imidazol-1-yl-1-methylindol-3-yl)-4-(6-methoxy-1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C=1N(C)C2=CC(OC)=CC=C2C=1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1C=CN=C1 HSKQEYPXKXWWNI-UHFFFAOYSA-N 0.000 claims description 2
DGJJEWKXNYUASE-UHFFFAOYSA-N 3-[1-(methoxymethyl)-6-pyrrolidin-1-ylindol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(COC)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1N1CCCC1 DGJJEWKXNYUASE-UHFFFAOYSA-N 0.000 claims description 2
LUDYRLUZWGKVHG-UHFFFAOYSA-N 3-[1-methyl-6-(2-methylimidazol-1-yl)indol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound CC1=NC=CN1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=C1 LUDYRLUZWGKVHG-UHFFFAOYSA-N 0.000 claims description 2
IJAKLJXSMKORAN-UHFFFAOYSA-N 3-[6-(1h-imidazol-2-yl)-1-methylindol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C1=NC=CN1 IJAKLJXSMKORAN-UHFFFAOYSA-N 0.000 claims description 2
ZTMXHKRBUXCPRU-UHFFFAOYSA-N 3-[6-(1h-imidazol-5-yl)-1-methylindol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione;hydrochloride Chemical compound Cl.C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C1=CN=CN1 ZTMXHKRBUXCPRU-UHFFFAOYSA-N 0.000 claims description 2
MGGLOLMTVMUQJL-UHFFFAOYSA-N 3-[6-(2-imidazol-1-ylethoxy)-1-methylindol-3-yl]-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1OCCN1C=CN=C1 MGGLOLMTVMUQJL-UHFFFAOYSA-N 0.000 claims description 2
IQDZUNNCBHJFIZ-UHFFFAOYSA-N 3-[6-(furan-2-yl)-1-methylindol-3-yl]-4-(1h-indol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=CC=C4NC=3)=O)C2=CC=C1C1=CC=CO1 IQDZUNNCBHJFIZ-UHFFFAOYSA-N 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
JDIZHNLZWMMAHJ-UHFFFAOYSA-N 3-(1-methyl-6-morpholin-4-ylindol-3-yl)-4-(1-methyl-6-nitroindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1N1CCOCC1 JDIZHNLZWMMAHJ-UHFFFAOYSA-N 0.000 claims 1
GKECJQFDVYWRIT-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-(1-methyl-6-pyrazol-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1N1C=CC=N1 GKECJQFDVYWRIT-UHFFFAOYSA-N 0.000 claims 1
FJELDZJUNHZKSI-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1N1CCCC1 FJELDZJUNHZKSI-UHFFFAOYSA-N 0.000 claims 1
XZDPLOHEGUNTBJ-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-[1-methyl-6-(1,2-thiazol-5-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C1=CC=NS1 XZDPLOHEGUNTBJ-UHFFFAOYSA-N 0.000 claims 1
FDNDQVRVAFJBSQ-UHFFFAOYSA-N 3-(1-methyl-6-nitroindol-3-yl)-4-[1-methyl-6-(1,3-thiazol-2-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound C1=C2N(C)C=C(C=3C(NC(=O)C=3C=3C4=CC=C(C=C4N(C)C=3)[N+]([O-])=O)=O)C2=CC=C1C1=NC=CS1 FDNDQVRVAFJBSQ-UHFFFAOYSA-N 0.000 claims 1
CPLDSWUMBFVCDU-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-piperidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCCCC1 CPLDSWUMBFVCDU-UHFFFAOYSA-N 0.000 claims 1
OUDGZSFEJDVQPS-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCCC1 OUDGZSFEJDVQPS-UHFFFAOYSA-N 0.000 claims 1
RBXFVCQSWJGFHS-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[1-methyl-6-(1,3-thiazol-2-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2C1=NC=CS1 RBXFVCQSWJGFHS-UHFFFAOYSA-N 0.000 claims 1
YOEBLKJDGBJUPL-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[1-methyl-6-(2-methylpyrazol-3-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound CN1N=CC=C1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=CC=C4N(C)C=3)=O)C2=C1 YOEBLKJDGBJUPL-UHFFFAOYSA-N 0.000 claims 1
DOZPBJAJHJZHHH-UHFFFAOYSA-N 3-(1-methylindol-3-yl)-4-[1-methyl-6-(4-methylpiperazin-1-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound C1CN(C)CCN1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=CC=C4N(C)C=3)=O)C2=C1 DOZPBJAJHJZHHH-UHFFFAOYSA-N 0.000 claims 1
BKCQTCCEGCECMO-UHFFFAOYSA-N 3-(6-bromo-1-methylindol-3-yl)-4-(1-methyl-6-pyrazol-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Br)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1C=CC=N1 BKCQTCCEGCECMO-UHFFFAOYSA-N 0.000 claims 1
JJGCEOSXCVMPLH-UHFFFAOYSA-N 3-(6-bromo-1-methylindol-3-yl)-4-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Br)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCCC1 JJGCEOSXCVMPLH-UHFFFAOYSA-N 0.000 claims 1
DGXDDUAYTVVYJC-UHFFFAOYSA-N 3-(6-bromo-1-methylindol-3-yl)-4-(6-imidazol-1-yl-1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Br)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1C=CN=C1 DGXDDUAYTVVYJC-UHFFFAOYSA-N 0.000 claims 1
NJVGOXAFJMKEOK-UHFFFAOYSA-N 3-(6-bromo-1-methylindol-3-yl)-4-[1-methyl-6-(2-methylpyrazol-3-yl)indol-3-yl]pyrrole-2,5-dione Chemical compound CN1N=CC=C1C1=CC=C(C(=CN2C)C=3C(NC(=O)C=3C=3C4=CC=C(Br)C=C4N(C)C=3)=O)C2=C1 NJVGOXAFJMKEOK-UHFFFAOYSA-N 0.000 claims 1
AJTOODUJJYOVOM-UHFFFAOYSA-N 3-(6-chloro-1-methylindol-3-yl)-4-(1-methyl-6-pyrrolidin-1-ylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(Cl)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CN(C)C1=CC=2N1CCCC1 AJTOODUJJYOVOM-UHFFFAOYSA-N 0.000 claims 1
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XCMVGOHSBPQTHJ-UHFFFAOYSA-N 3-(6-fluoro-1-methylindol-3-yl)-4-(6-morpholin-4-yl-1h-indol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=C(F)C=C2N(C)C=C1C(C(NC1=O)=O)=C1C(C1=CC=2)=CNC1=CC=2N1CCOCC1 XCMVGOHSBPQTHJ-UHFFFAOYSA-N 0.000 claims 1
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239000011248 coating agent Substances 0.000 description 1
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229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
QOYXXYURGXSAAP-UHFFFAOYSA-N methyl 2-(1-methyl-6-morpholin-4-ylindol-3-yl)acetate Chemical compound C=1C=C2C(CC(=O)OC)=CN(C)C2=CC=1N1CCOCC1 QOYXXYURGXSAAP-UHFFFAOYSA-N 0.000 description 1
YVFJSJKSEFNAQT-UHFFFAOYSA-N methyl 2-(6-chloro-1-methylindol-3-yl)-2-oxoacetate Chemical compound ClC1=CC=C2C(C(=O)C(=O)OC)=CN(C)C2=C1 YVFJSJKSEFNAQT-UHFFFAOYSA-N 0.000 description 1
LLTLUNOILJZJHI-UHFFFAOYSA-N methyl 2-(6-cyano-1-methylindol-3-yl)-2-oxoacetate Chemical compound N#CC1=CC=C2C(C(=O)C(=O)OC)=CN(C)C2=C1 LLTLUNOILJZJHI-UHFFFAOYSA-N 0.000 description 1
KRRFYHUBFRJCLU-UHFFFAOYSA-N methyl 2-(6-imidazol-1-yl-1-methylindol-3-yl)acetate Chemical compound C=1C=C2C(CC(=O)OC)=CN(C)C2=CC=1N1C=CN=C1 KRRFYHUBFRJCLU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
LUCDCOFPPWFTBX-UHFFFAOYSA-N propan-2-yl 2-(1-methyl-6-morpholin-4-ylindol-3-yl)ethanimidate;hydrochloride Chemical compound Cl.C=1C=C2C(CC(=N)OC(C)C)=CN(C)C2=CC=1N1CCOCC1 LUCDCOFPPWFTBX-UHFFFAOYSA-N 0.000 description 1
JOEUBPUUCQZRPZ-UHFFFAOYSA-N propan-2-yl 2-(2-methyl-1h-indol-3-yl)ethanimidate;hydrochloride Chemical compound Cl.C1=CC=C2C(CC(=N)OC(C)C)=C(C)NC2=C1 JOEUBPUUCQZRPZ-UHFFFAOYSA-N 0.000 description 1
HDKFLPCEAMPERX-UHFFFAOYSA-N propan-2-yl 2-(6-chloro-1-methylindol-3-yl)ethanimidate;hydrochloride Chemical compound Cl.ClC1=CC=C2C(CC(=N)OC(C)C)=CN(C)C2=C1 HDKFLPCEAMPERX-UHFFFAOYSA-N 0.000 description 1
NXSKAFXOBAPOFO-UHFFFAOYSA-N propan-2-yl 2-(6-methoxy-1-methylindol-3-yl)ethanimidate;hydrochloride Chemical compound Cl.COC1=CC=C2C(CC(=N)OC(C)C)=CN(C)C2=C1 NXSKAFXOBAPOFO-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
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 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
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
OGYWKJKAIAEDQX-UHFFFAOYSA-N tributyl-(3-methylimidazol-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CN1C OGYWKJKAIAEDQX-UHFFFAOYSA-N 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
ULLJBPWMQNTUPF-UHFFFAOYSA-N trimethyl-[2-[[5-(1-methylindol-6-yl)imidazol-1-yl]methoxy]ethyl]silane Chemical compound C1=C2N(C)C=CC2=CC=C1C1=CN=CN1COCC[Si](C)(C)C ULLJBPWMQNTUPF-UHFFFAOYSA-N 0.000 description 1
239000012178 vegetable wax Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07D403/14—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 three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- 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
- 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
- C07D405/14—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 three or more hetero rings
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D417/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

ZA200204313A 1999-12-22 2002-05-29 Substituted pyrroles. ZA200204313B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US17155799P	1999-12-22	1999-12-22

Publications (1)

Publication Number	Publication Date
ZA200204313B true ZA200204313B (en)	2003-08-29

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ID=22624198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200204313A ZA200204313B (en)	1999-12-22	2002-05-29	Substituted pyrroles.

Country Status (28)

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US (1)	US6281356B1 (cs)
EP (1)	EP1242409A2 (cs)
JP (1)	JP2003518112A (cs)
KR (1)	KR100508741B1 (cs)
CN (1)	CN1193027C (cs)
AR (1)	AR027035A1 (cs)
AU (1)	AU782920B2 (cs)
BR (1)	BR0016516A (cs)
CA (1)	CA2394852A1 (cs)
CO (1)	CO5090902A1 (cs)
CZ (1)	CZ20022492A3 (cs)
HK (1)	HK1054382A1 (cs)
HR (1)	HRP20020536A2 (cs)
HU (1)	HUP0204572A3 (cs)
IL (1)	IL150200A0 (cs)
JO (1)	JO2199B1 (cs)
MA (1)	MA26860A1 (cs)
MX (1)	MXPA02006162A (cs)
MY (1)	MY133682A (cs)
NO (1)	NO20022927L (cs)
NZ (1)	NZ519359A (cs)
PE (1)	PE20011098A1 (cs)
PL (1)	PL357603A1 (cs)
RU (1)	RU2261862C2 (cs)
UY (1)	UY26498A1 (cs)
WO (1)	WO2001046178A2 (cs)
YU (1)	YU46302A (cs)
ZA (1)	ZA200204313B (cs)

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Publication number	Priority date	Publication date	Assignee	Title
US20030139373A1 (en) *	2001-11-20	2003-07-24	Breimer Lars Holger	Method for cancer therapy
TWI324064B (en)	2002-04-03	2010-05-01	Novartis Ag	Indolylmaleimide derivatives
GB0303319D0 (en)	2003-02-13	2003-03-19	Novartis Ag	Organic compounds
MX2015012456A (es)	2013-03-15	2016-02-03	Plexxikon Inc	Compuestos heterociclicos y usos de los mismos.
US20140303121A1 (en)	2013-03-15	2014-10-09	Plexxikon Inc.	Heterocyclic compounds and uses thereof
PT3272745T (pt)	2016-07-21	2019-09-27	Inst Farmakologii Polskiej Akademii Nauk	Derivados de indol substituídos com imidazolilo que se ligam ao recetor de serotonina 5-ht7 e composições farmacêuticas dos mesmos
EP3694855A1 (en)	2017-10-13	2020-08-19	Plexxikon Inc.	Solid forms of a compound for modulating kinases

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SK278989B6 (sk)	1988-02-10	1998-05-06	F. Hoffmann-La Roche Ag	Substituované pyroly, ich použitie na výrobu lieči
US5380746A (en)	1989-05-05	1995-01-10	Goedecke Aktiengesellschaft	Bis-(1H-indol-3-YL)-maleinimide derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
IL94274A0 (en) *	1989-05-05	1991-03-10	Goedecke Ag	Maleinimide derivatives,process for the preparation thereof and pharmaceutical compositions containing the same
AU3761393A (en)	1992-03-20	1993-10-21	Wellcome Foundation Limited, The	Indole derivatives with antiviral activity
WO1993018766A1 (en) *	1992-03-20	1993-09-30	The Wellcome Foundation Limited	Further indole derivatives with antiviral activity
DE4217964A1 (de) *	1992-05-30	1993-12-02	Goedecke Ag	Indolocarbazol-Imide und deren Verwendung
PE91698A1 (es)	1996-07-29	1998-12-24	Hoffmann La Roche	Pirroles sustituidos
PE91498A1 (es)	1996-07-29	1998-12-22	Hoffmann La Roche	Pirroles sustituidos
PE91598A1 (es)	1996-07-29	1998-12-24	Hoffmann La Roche	Pirroles sustituidos
EP1064279B1 (en) *	1998-03-17	2003-06-25	F.Hoffmann-La Roche Ag	Substituted bisindolylmaleimides for the inhibition of cell proliferation

2000
- 2000-12-15 US US09/737,685 patent/US6281356B1/en not_active Expired - Fee Related
- 2000-12-19 JO JO2000203A patent/JO2199B1/en active
- 2000-12-20 CO CO00096628A patent/CO5090902A1/es unknown
- 2000-12-20 MY MYPI20006018A patent/MY133682A/en unknown
- 2000-12-20 AR ARP000106792A patent/AR027035A1/es not_active Application Discontinuation
- 2000-12-21 YU YU46302A patent/YU46302A/sh unknown
- 2000-12-21 IL IL15020000A patent/IL150200A0/xx unknown
- 2000-12-21 PE PE2000001386A patent/PE20011098A1/es not_active Application Discontinuation
- 2000-12-21 MX MXPA02006162A patent/MXPA02006162A/es not_active Application Discontinuation
- 2000-12-21 CZ CZ20022492A patent/CZ20022492A3/cs unknown
- 2000-12-21 PL PL00357603A patent/PL357603A1/xx not_active Application Discontinuation
- 2000-12-21 EP EP00991984A patent/EP1242409A2/en not_active Withdrawn
- 2000-12-21 KR KR10-2002-7008019A patent/KR100508741B1/ko not_active IP Right Cessation
- 2000-12-21 UY UY26498A patent/UY26498A1/es not_active Application Discontinuation
- 2000-12-21 CA CA002394852A patent/CA2394852A1/en not_active Abandoned
- 2000-12-21 WO PCT/EP2000/013026 patent/WO2001046178A2/en not_active Application Discontinuation
- 2000-12-21 JP JP2001547088A patent/JP2003518112A/ja active Pending
- 2000-12-21 NZ NZ519359A patent/NZ519359A/en unknown
- 2000-12-21 RU RU2002119557/04A patent/RU2261862C2/ru not_active IP Right Cessation
- 2000-12-21 HU HU0204572A patent/HUP0204572A3/hu unknown
- 2000-12-21 AU AU37267/01A patent/AU782920B2/en not_active Ceased
- 2000-12-21 BR BR0016516-6A patent/BR0016516A/pt not_active IP Right Cessation
- 2000-12-21 CN CNB008173885A patent/CN1193027C/zh not_active Expired - Fee Related
2002
- 2002-05-29 ZA ZA200204313A patent/ZA200204313B/en unknown
- 2002-06-18 NO NO20022927A patent/NO20022927L/no not_active Application Discontinuation
- 2002-06-20 HR HR20020536A patent/HRP20020536A2/hr not_active Application Discontinuation
- 2002-06-21 MA MA26707A patent/MA26860A1/fr unknown
2003
- 2003-09-15 HK HK03106619A patent/HK1054382A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO20022927D0 (no)	2002-06-18
CA2394852A1 (en)	2001-06-28
MXPA02006162A (es)	2002-12-05
NO20022927L (no)	2002-06-18
RU2002119557A (ru)	2004-01-10
UY26498A1 (es)	2001-06-29
EP1242409A2 (en)	2002-09-25
JO2199B1 (en)	2003-12-23
AU782920B2 (en)	2005-09-08
US6281356B1 (en)	2001-08-28
CN1411457A (zh)	2003-04-16
CN1193027C (zh)	2005-03-16
KR20020062365A (ko)	2002-07-25
KR100508741B1 (ko)	2005-08-17
NZ519359A (en)	2004-04-30
PE20011098A1 (es)	2001-10-26
MY133682A (en)	2007-11-30
CO5090902A1 (es)	2001-10-30
JP2003518112A (ja)	2003-06-03
PL357603A1 (en)	2004-07-26
YU46302A (sh)	2005-06-10
HUP0204572A2 (en)	2003-05-28
HK1054382A1 (en)	2003-11-28
CZ20022492A3 (cs)	2003-02-12
IL150200A0 (en)	2002-12-01
AR027035A1 (es)	2003-03-12
BR0016516A (pt)	2002-09-17
WO2001046178A2 (en)	2001-06-28
HRP20020536A2 (en)	2004-08-31
MA26860A1 (fr)	2004-12-20
RU2261862C2 (ru)	2005-10-10
HUP0204572A3 (en)	2004-07-28
WO2001046178A3 (en)	2001-12-06
AU3726701A (en)	2001-07-03

Publication	Publication Date	Title
US5057614A (en)	1991-10-15	Substituted pyrroles
CA2534921C (en)	2011-06-14	Aminotriazole compounds useful as inhibitors of protein kinases
AU638510B2 (en)	1993-07-01	Indole derivatives
EP1606284B1 (en)	2009-12-02	Compositions useful as protein kinase inhibitors
PL168902B1 (pl)	1996-05-31	Sposób wytwarzania nowych indolo-i benzimidazolopodstawionych pochodnych imidazolu i benzimidazolu PL PL
JP2000516588A (ja)	2000-12-12	細胞増殖阻害のための置換ビスインドリルマレイミド
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