HRP970414A2 - Substituted pyrroles - Google Patents

Substituted pyrroles Download PDF

Info

Publication number: HRP970414A2
Authority: HR; Croatia
Prior art keywords: methyl; alkyl; hydrogen; compound according; indol
Prior art date: 1996-07-29

Application number

HR60/022,079A

Other languages

English (en)

Croatian (hr)

Inventor

Dennis Dalton Keith

Original Assignee

Dennis Dalton Keith

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.)

1996-07-29

Filing date

1997-07-25

Publication date

1998-06-30

1997-07-25 Application filed by Dennis Dalton Keith filed Critical Dennis Dalton Keith

1998-06-30 Publication of HRP970414A2 publication Critical patent/HRP970414A2/hr

Links

150000003233 pyrroles Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 37
-1 nitro, amino Chemical group 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000007514 bases Chemical class 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
239000000651 prodrug Substances 0.000 claims description 4
229940002612 prodrug Drugs 0.000 claims description 4
DVINAGLCMNECAC-UHFFFAOYSA-N 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-6-carbonitrile Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=C(C=C3N(C)C=2)C#N)C(=O)NC1=O DVINAGLCMNECAC-UHFFFAOYSA-N 0.000 claims description 3
JDFHTCHKNZWWME-UHFFFAOYSA-N 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-6-carboxamide Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=C(C=C3N(C)C=2)C(N)=O)C(=O)NC1=O JDFHTCHKNZWWME-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
SFQHEVSHOZMLHO-UHFFFAOYSA-N 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-5-carbonitrile Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC(=CC=C3N(C)C=2)C#N)C(=O)NC1=O SFQHEVSHOZMLHO-UHFFFAOYSA-N 0.000 claims description 2
MDWMQNXUCMJGRZ-UHFFFAOYSA-N 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-6-carbaldehyde Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=C(C=O)C=C3N(C)C=2)C(=O)NC1=O MDWMQNXUCMJGRZ-UHFFFAOYSA-N 0.000 claims description 2
FIHANSAKBFCDEI-UHFFFAOYSA-N 3-[6-(hydroxymethyl)-1-methylindol-3-yl]-4-(1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=C(CO)C=C3N(C)C=2)C(=O)NC1=O FIHANSAKBFCDEI-UHFFFAOYSA-N 0.000 claims description 2
AQLOOCUUKNWXPG-UHFFFAOYSA-N 3-[6-(methoxymethyl)-1-methylindol-3-yl]-4-(1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=CC=C2C(C3=C(C(NC3=O)=O)C=3C4=CC=C(C=C4N(C)C=3)COC)=CN(C)C2=C1 AQLOOCUUKNWXPG-UHFFFAOYSA-N 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
230000004663 cell proliferation Effects 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
239000008194 pharmaceutical composition Substances 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
239000000243 solution Substances 0.000 description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 12
239000000126 substance Substances 0.000 description 11
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
238000000034 method Methods 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000000969 carrier Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
230000009467 reduction Effects 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
KHBZWURVKMBOJF-UHFFFAOYSA-N propan-2-yl 2-(1-methylindol-3-yl)ethanimidate;hydrochloride Chemical compound Cl.C1=CC=C2C(CC(=N)OC(C)C)=CN(C)C2=C1 KHBZWURVKMBOJF-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
230000001629 suppression Effects 0.000 description 3
GMZLJGSFSROWDH-UHFFFAOYSA-N (1-propan-2-ylindol-6-yl)methanol Chemical compound C1=C(CO)C=C2N(C(C)C)C=CC2=C1 GMZLJGSFSROWDH-UHFFFAOYSA-N 0.000 description 2
FOGAAHLMYPQCJG-UHFFFAOYSA-N 1-methylindole-6-carbonitrile Chemical compound C1=C(C#N)C=C2N(C)C=CC2=C1 FOGAAHLMYPQCJG-UHFFFAOYSA-N 0.000 description 2
DJQOGNYSBOIJKE-UHFFFAOYSA-N 1-methylindole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N(C)C=CC2=C1 DJQOGNYSBOIJKE-UHFFFAOYSA-N 0.000 description 2
WRMZOPANDOHWJU-UHFFFAOYSA-N 1h-indol-6-ylmethanol Chemical compound OCC1=CC=C2C=CNC2=C1 WRMZOPANDOHWJU-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 2
RDUNGWNDEZRPNR-UHFFFAOYSA-N 3-[6-(methoxymethyl)-1-propan-2-ylindol-3-yl]-4-(1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound C1=CC=C2C(C3=C(C(NC3=O)=O)C=3C4=CC=C(C=C4N(C(C)C)C=3)COC)=CN(C)C2=C1 RDUNGWNDEZRPNR-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
QIGUKECNAHDTBJ-UHFFFAOYSA-N 6-(methoxymethyl)-1-propan-2-ylindole Chemical compound COCC1=CC=C2C=CN(C(C)C)C2=C1 QIGUKECNAHDTBJ-UHFFFAOYSA-N 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
230000001028 anti-proliverative effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
239000008298 dragée Substances 0.000 description 2
MHOPHBTXZRCXJY-UHFFFAOYSA-N ethyl 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-6-carboxylate Chemical compound C1=CC=C2C(C3=C(C(NC3=O)=O)C=3C4=CC=C(C=C4N(C)C=3)C(=O)OCC)=CN(C)C2=C1 MHOPHBTXZRCXJY-UHFFFAOYSA-N 0.000 description 2
DONAUJDYIXJJJF-UHFFFAOYSA-N ethyl 1-methylindole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2C=CN(C)C2=C1 DONAUJDYIXJJJF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000003925 fat Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
QFHTWTKDRUFTJW-UHFFFAOYSA-N methyl 1-propan-2-ylindole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CN(C(C)C)C2=C1 QFHTWTKDRUFTJW-UHFFFAOYSA-N 0.000 description 2
FWZSWIXOPWURKN-UHFFFAOYSA-N methyl 3-amino-4-(2,2-dimethoxyethyl)benzoate Chemical compound COC(OC)CC1=CC=C(C(=O)OC)C=C1N FWZSWIXOPWURKN-UHFFFAOYSA-N 0.000 description 2
IUYADMKILLYZCD-UHFFFAOYSA-N methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate Chemical compound COC(OC)CC1=CC=C(C(=O)OC)C=C1[N+]([O-])=O IUYADMKILLYZCD-UHFFFAOYSA-N 0.000 description 2
RTGNZFSMKJWWKA-UHFFFAOYSA-N methyl 4-[2-(dimethylamino)ethenyl]-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(C=CN(C)C)C([N+]([O-])=O)=C1 RTGNZFSMKJWWKA-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000000746 purification Methods 0.000 description 2
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 2
239000012047 saturated solution Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000004001 thioalkyl group Chemical group 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
NSEKMGOCNRXLEG-UHFFFAOYSA-N (1-methylindol-6-yl)methyl acetate Chemical compound CC(=O)OCC1=CC=C2C=CN(C)C2=C1 NSEKMGOCNRXLEG-UHFFFAOYSA-N 0.000 description 1
DYZZFEHAJOLDEX-UHFFFAOYSA-N 1-methylindole-5-carbonitrile Chemical compound N#CC1=CC=C2N(C)C=CC2=C1 DYZZFEHAJOLDEX-UHFFFAOYSA-N 0.000 description 1
QGAKKGIWURKKHV-UHFFFAOYSA-N 1-methylindole-6-carbaldehyde Chemical compound C1=C(C=O)C=C2N(C)C=CC2=C1 QGAKKGIWURKKHV-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
WEFXNTLSKCMIME-UHFFFAOYSA-N 2-(6-cyano-1-methylindol-3-yl)-2-oxoacetyl chloride Chemical compound C1=C(C#N)C=C2N(C)C=C(C(=O)C(Cl)=O)C2=C1 WEFXNTLSKCMIME-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
FGPWYCKELFZGGE-UHFFFAOYSA-N 2-cyanato-2-oxoacetic acid Chemical class OC(=O)C(=O)OC#N FGPWYCKELFZGGE-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
BBEWSMNRCUXQRF-UHFFFAOYSA-N 4-methyl-3-nitrobenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1[N+]([O-])=O BBEWSMNRCUXQRF-UHFFFAOYSA-N 0.000 description 1
FYANEFRVLHNRCQ-UHFFFAOYSA-N 6-(methoxymethyl)-1-methylindole Chemical compound COCC1=CC=C2C=CN(C)C2=C1 FYANEFRVLHNRCQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920003081 Povidone K 30 Polymers 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000001980 alanyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000033077 cellular process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 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
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
239000008190 ground granulate Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
ZOEHAJLQPAVYBU-UHFFFAOYSA-N methyl 1-methyl-3-[4-(1-methylindol-3-yl)-2,5-dioxopyrrol-3-yl]indole-6-carboxylate Chemical compound C1=CC=C2C(C3=C(C(NC3=O)=O)C=3C4=CC=C(C=C4N(C)C=3)C(=O)OC)=CN(C)C2=C1 ZOEHAJLQPAVYBU-UHFFFAOYSA-N 0.000 description 1
NMILWYUYIFMKTE-UHFFFAOYSA-N methyl 1-methylindole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CN(C)C2=C1 NMILWYUYIFMKTE-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids 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
RGUOJYYIMVSCNC-UHFFFAOYSA-N n,n-dimethylformamide;2-methylpropanoic acid Chemical compound CN(C)C=O.CC(C)C(O)=O RGUOJYYIMVSCNC-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000000771 oncological effect Effects 0.000 description 1
210000000056 organ Anatomy 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
230000003204 osmotic effect Effects 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
238000007747 plating Methods 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
235000021395 porridge Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000005987 sulfurization reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 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
- 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
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)

HR60/022,079A 1996-07-29 1997-07-25 Substituted pyrroles HRP970414A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2207996P	1996-07-29	1996-07-29

Publications (1)

Publication Number	Publication Date
HRP970414A2 true HRP970414A2 (en)	1998-06-30

Family

ID=21807711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR60/022,079A HRP970414A2 (en)	1996-07-29	1997-07-25	Substituted pyrroles

Country Status (23)

Country	Link
US (2)	US5856517A (de)
EP (1)	EP0915872B1 (de)
JP (1)	JP2000516589A (de)
KR (1)	KR20000029637A (de)
CN (2)	CN1151149C (de)
AR (1)	AR008267A1 (de)
AT (1)	ATE240318T1 (de)
AU (1)	AU739742B2 (de)
BR (1)	BR9711605A (de)
CA (1)	CA2262092A1 (de)
CO (1)	CO4900055A1 (de)
CY (1)	CY2483B1 (de)
DE (1)	DE69722003T2 (de)
DK (1)	DK0915872T3 (de)
ES (1)	ES2198001T3 (de)
HR (1)	HRP970414A2 (de)
MA (1)	MA24287A1 (de)
PE (1)	PE91698A1 (de)
PT (1)	PT915872E (de)
SA (1)	SA97180473A (de)
TR (1)	TR199900157T2 (de)
WO (1)	WO1998004552A1 (de)
ZA (1)	ZA976492B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT1064279E (pt) *	1998-03-17	2003-10-31	Hoffmann La Roche	Bisindolilmaleimidas substituidas para a inibicao da proliferacao celular
US6743785B2 (en) *	1999-12-16	2004-06-01	Eli Lilly And Company	Agents and methods for the treatment of proliferative diseases
US6313143B1 (en)	1999-12-16	2001-11-06	Hoffmann-La Roche Inc.	Substituted pyrroles
AU2576901A (en) *	1999-12-16	2001-06-25	Eli Lilly And Company	Agents and methods for the treatment of proliferative diseases
EP1242420A2 (de)	1999-12-16	2002-09-25	Eli Lilly And Company	Mittel und verfahren zur behandlung von proliferativen erkrankungen
US6281356B1 (en) *	1999-12-22	2001-08-28	Hoffmann-La Roche Inc.	Substituted pyrroles
TW201041580A (en)	2001-09-27	2010-12-01	Alcon Inc	Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma
US20030139373A1 (en) *	2001-11-20	2003-07-24	Breimer Lars Holger	Method for cancer therapy
MY142390A (en) *	2002-05-22	2010-11-30	Glaxosmithkline Llc	3' - [(2z)-[1-(3,4-dimethylphenyl)-1,5- dihydro-3- methyl-5-0xo-4h-pyrazol-4- ylidene]hydrazino]-2' -hydroxy -[1,1' -biphenyl]-3-carboxylic acid bis-(monoethanolamine)
US7012100B1 (en)	2002-06-04	2006-03-14	Avolix Pharmaceuticals, Inc.	Cell migration inhibiting compositions and methods and compositions for treating cancer
KR100941205B1 (ko)	2005-02-09	2010-02-10	아르퀼 인코포레이티드	말레이미드 유도체, 약제학적 조성물 및 암을 치료하는방법
ES2410955T3 (es) *	2006-12-19	2013-07-04	Novartis Ag	Derivados de indolilmaleimida como inhibidores de la quinasa
CA2912546A1 (en)	2007-06-22	2008-12-31	Arqule, Inc.	Compositions and methods for treatment of cancer
EP2170870B1 (de)	2007-06-22	2014-03-05	ArQule, Inc.	Pyrrolidinon-, pyrrolidin-2,5-dion-, pyrrolidin- und thiosuccinimidderivate, zusammensetzungen und verfahren zur behandlung von krebs
KR20100024494A (ko)	2007-06-22	2010-03-05	아르퀼 인코포레이티드	퀴나졸리논 화합물 및 이의 사용 방법
JP2009035537A (ja) *	2007-07-10	2009-02-19	Nippon Synthetic Chem Ind Co Ltd:The	Ｎ−置換アニリン誘導体及び１−置換インドール誘導体の製造方法
FR2927075A1 (fr) *	2008-02-04	2009-08-07	Centre Nat Rech Scient	Molecules comprenant un squelette bis-(heteroaryl)maleimide, et leur utilisation dans l'inhibition d'enzymes
GB201111427D0 (en) *	2011-07-05	2011-08-17	Amakem Nv	Novel bisindolylmaleimides, pan-pkc inhibitors
ES2919024T3 (es)	2014-02-11	2022-07-21	Mitokinin Inc	Composiciones y procedimientos que utilizan las mismas para el tratamiento de enfermedades neurodegenerativas y mitocondriales
EP3741375A1 (de)	2014-07-17	2020-11-25	INSERM (Institut National de la Santé et de la Recherche Médicale)	Verfahren zur behandlung von erkrankungen in zusammenhang mit neuromuskulären verbindungen
WO2016207366A1 (en)	2015-06-26	2016-12-29	INSERM (Institut National de la Santé et de la Recherche Médicale)	Methods and pharmaceutical compositions for the treatment of viral infections
AU2018290225A1 (en)	2017-06-21	2020-01-23	Mitokinin, Inc.	Compositions and methods using the same for treatment of neurodegenerative and mitochondrial disease

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ227850A (en) *	1988-02-10	1991-11-26	Hoffmann La Roche	Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders
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
CA2015996C (en) *	1989-05-05	2001-08-28	Hartmut Osswald	Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals
DE4005969A1 (de) *	1990-02-26	1991-08-29	Boehringer Mannheim Gmbh	Neue trisubstituierte pyrrole, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten
JPH0539289A (ja) *	1991-02-15	1993-02-19	Masahiro Irie	無水マレイン酸誘導体およびその製造方法
AU3761393A (en) *	1992-03-20	1993-10-21	Wellcome Foundation Limited, The	Indole derivatives with antiviral activity
DE4217964A1 (de) *	1992-05-30	1993-12-02	Goedecke Ag	Indolocarbazol-Imide und deren Verwendung

1997
- 1997-07-15 PE PE1997000630A patent/PE91698A1/es not_active Application Discontinuation
- 1997-07-19 CN CNB971967768A patent/CN1151149C/zh not_active Expired - Fee Related
- 1997-07-19 CA CA002262092A patent/CA2262092A1/en not_active Abandoned
- 1997-07-19 PT PT97934498T patent/PT915872E/pt unknown
- 1997-07-19 BR BR9711605A patent/BR9711605A/pt not_active Application Discontinuation
- 1997-07-19 KR KR1019997000706A patent/KR20000029637A/ko not_active Abandoned
- 1997-07-19 AU AU37690/97A patent/AU739742B2/en not_active Ceased
- 1997-07-19 JP JP10508453A patent/JP2000516589A/ja not_active Ceased
- 1997-07-19 DE DE69722003T patent/DE69722003T2/de not_active Expired - Fee Related
- 1997-07-19 ES ES97934498T patent/ES2198001T3/es not_active Expired - Lifetime
- 1997-07-19 EP EP97934498A patent/EP0915872B1/de not_active Expired - Lifetime
- 1997-07-19 CN CNA031275400A patent/CN1495182A/zh active Pending
- 1997-07-19 AT AT97934498T patent/ATE240318T1/de not_active IP Right Cessation
- 1997-07-19 TR TR1999/00157T patent/TR199900157T2/xx unknown
- 1997-07-19 WO PCT/EP1997/003889 patent/WO1998004552A1/en not_active Ceased
- 1997-07-19 DK DK97934498T patent/DK0915872T3/da active
- 1997-07-22 ZA ZA9706492A patent/ZA976492B/xx unknown
- 1997-07-22 AR ARP970103309A patent/AR008267A1/es not_active Application Discontinuation
- 1997-07-24 US US08/899,852 patent/US5856517A/en not_active Expired - Fee Related
- 1997-07-25 CO CO97042581A patent/CO4900055A1/es unknown
- 1997-07-25 HR HR60/022,079A patent/HRP970414A2/hr not_active Application Discontinuation
- 1997-07-29 MA MA24744A patent/MA24287A1/fr unknown
- 1997-10-06 SA SA97180473A patent/SA97180473A/ar unknown
1998
- 1998-10-05 US US09/166,766 patent/US6030994A/en not_active Expired - Fee Related
2004
- 2004-11-15 CY CY0400081A patent/CY2483B1/xx unknown

Also Published As

Publication number	Publication date
PT915872E (pt)	2003-09-30
US5856517A (en)	1999-01-05
PE91698A1 (es)	1998-12-24
WO1998004552A1 (en)	1998-02-05
EP0915872A1 (de)	1999-05-19
DK0915872T3 (da)	2003-09-08
BR9711605A (pt)	1999-08-24
AR008267A1 (es)	1999-12-29
JP2000516589A (ja)	2000-12-12
AU3769097A (en)	1998-02-20
ES2198001T3 (es)	2004-01-16
CY2483B1 (en)	2005-06-03
TR199900157T2 (xx)	1999-04-21
EP0915872B1 (de)	2003-05-14
CN1495182A (zh)	2004-05-12
DE69722003T2 (de)	2004-04-01
AU739742B2 (en)	2001-10-18
SA97180473A (ar)	2005-12-03
ZA976492B (en)	1998-01-29
DE69722003D1 (de)	2003-06-18
CO4900055A1 (es)	2000-03-27
KR20000029637A (ko)	2000-05-25
MA24287A1 (fr)	1998-04-01
CN1151149C (zh)	2004-05-26
US6030994A (en)	2000-02-29
CA2262092A1 (en)	1998-02-05
ATE240318T1 (de)	2003-05-15
CN1226247A (zh)	1999-08-18

Legal Events

Date	Code	Title	Description
1998-06-30	A1OB	Publication of a patent application
1999-06-23	ODBC	Application rejected

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