NO309655B1 - Nye elliptikinforbindelser, fremgangsmåte for deres fremstilling og farmasöytiske sammensetninger inneholdende dem - Google Patents

Nye elliptikinforbindelser, fremgangsmåte for deres fremstilling og farmasöytiske sammensetninger inneholdende dem Download PDF

Info

Publication number: NO309655B1
Authority: NO; Norway
Prior art keywords: alkyl; radicals; substituted; formula; benzyloxycarbonyl
Prior art date: 1996-12-30

Application number

NO976106A

Other languages

English (en)

Norwegian (no)

Other versions

NO976106D0 (no

NO976106L (no

Inventor

Claude Guillonneau

Yves Charton

Emile Bisagni

Ghanem Atassi

Alain Pierre

Nicolas Guilbaud

Original Assignee

Adir

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.)

1996-12-30

Filing date

1997-12-29

Publication date

2001-03-05

1997-12-29 Application filed by Adir filed Critical Adir

1997-12-29 Publication of NO976106D0 publication Critical patent/NO976106D0/no

1998-07-01 Publication of NO976106L publication Critical patent/NO976106L/no

2001-03-05 Publication of NO309655B1 publication Critical patent/NO309655B1/no

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
CTSPAMFJBXKSOY-UHFFFAOYSA-N ellipticine Chemical class N1=CC=C2C(C)=C(NC=3C4=CC=CC=3)C4=C(C)C2=C1 CTSPAMFJBXKSOY-UHFFFAOYSA-N 0.000 title abstract description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 30
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 7
150000001204 N-oxides Chemical class 0.000 claims abstract description 5
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 5
229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 5
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 70
-1 alkyl radical Chemical class 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 17
125000003277 amino group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
125000004193 piperazinyl group Chemical group 0.000 claims description 7
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 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
239000000852 hydrogen donor Substances 0.000 claims description 5
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000004181 carboxyalkyl group Chemical group 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
238000011275 oncology therapy Methods 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 7
150000002430 hydrocarbons Chemical group 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000003118 aryl group Chemical group 0.000 abstract 2
125000001072 heteroaryl group Chemical group 0.000 abstract 2
125000005842 heteroatom Chemical group 0.000 abstract 2
125000000623 heterocyclic group Chemical group 0.000 abstract 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
239000005977 Ethylene Substances 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000002950 monocyclic group Chemical group 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
230000003287 optical effect Effects 0.000 abstract 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
229920006395 saturated elastomer Polymers 0.000 abstract 1
125000004434 sulfur atom Chemical group 0.000 abstract 1
229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229940009456 adriamycin Drugs 0.000 description 8
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
ZIXGXMMUKPLXBB-UHFFFAOYSA-N Guatambuinine Natural products N1C2=CC=CC=C2C2=C1C(C)=C1C=CN=C(C)C1=C2 ZIXGXMMUKPLXBB-UHFFFAOYSA-N 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
230000000259 anti-tumor effect Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
206010058467 Lung neoplasm malignant Diseases 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
201000005296 lung carcinoma Diseases 0.000 description 3
AEYWPRODWLOEFK-UHFFFAOYSA-N n-methylmethanamine;pyridine Chemical compound CNC.C1=CC=NC=C1 AEYWPRODWLOEFK-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
WBGUTGOSUBJTJZ-UHFFFAOYSA-N 1,5-dimethyl-2H-pyrido[4,3-b]carbazole Chemical compound Cc1[nH]ccc2c(C)c3nc4ccccc4c3cc12 WBGUTGOSUBJTJZ-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
208000008342 Leukemia P388 Diseases 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007398 colorimetric assay Methods 0.000 description 2
231100000433 cytotoxic Toxicity 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100001274 therapeutic index Toxicity 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
SUYXJDLXGFPMCQ-INIZCTEOSA-N SJ000287331 Natural products CC1=c2cnccc2=C(C)C2=Nc3ccccc3[C@H]12 SUYXJDLXGFPMCQ-INIZCTEOSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
230000035572 chemosensitivity Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
239000006196 drop Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000005917 in vivo anti-tumor Effects 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
230000007774 longterm Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
230000036457 multidrug resistance Effects 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
210000003281 pleural cavity Anatomy 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
RCRYHUPTBJZEQS-UHFFFAOYSA-N tetradecanoyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCC RCRYHUPTBJZEQS-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)

NO976106A 1996-12-30 1997-12-29 Nye elliptikinforbindelser, fremgangsmåte for deres fremstilling og farmasöytiske sammensetninger inneholdende dem NO309655B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9616165A FR2757859B1 (fr)	1996-12-30	1996-12-30	Nouveaux derives d'ellipticine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (3)

Publication Number	Publication Date
NO976106D0 NO976106D0 (no)	1997-12-29
NO976106L NO976106L (no)	1998-07-01
NO309655B1 true NO309655B1 (no)	2001-03-05

Family

ID=9499261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO976106A NO309655B1 (no)	1996-12-30	1997-12-29	Nye elliptikinforbindelser, fremgangsmåte for deres fremstilling og farmasöytiske sammensetninger inneholdende dem

Country Status (18)

Country	Link
US (1)	US6162811A (de)
EP (1)	EP0850940B1 (de)
JP (1)	JPH10195074A (de)
AT (1)	ATE201208T1 (de)
AU (1)	AU736292B2 (de)
BR (1)	BR9706497A (de)
CA (1)	CA2227506A1 (de)
DE (1)	DE69704840T2 (de)
DK (1)	DK0850940T3 (de)
ES (1)	ES2159098T3 (de)
FR (1)	FR2757859B1 (de)
GR (1)	GR3036245T3 (de)
HU (1)	HUP9702542A3 (de)
NO (1)	NO309655B1 (de)
NZ (1)	NZ329510A (de)
PL (1)	PL324069A1 (de)
PT (1)	PT850940E (de)
ZA (1)	ZA9711709B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6562995B1 (en) *	2000-12-21	2003-05-13	Beacon Laboratories, Inc.	Delta dicarbonyl compounds and methods for using the same
FR2859474B1 (fr) *	2003-09-04	2006-01-13	Centre Nat Rech Scient	Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3933827A (en) *	1974-10-29	1976-01-20	Hoffmann-La Roche Inc.	9-Acyloxy-5,11-dimethyl-6H-pyrido[4,3-B]carbazoles
FR2696465B1 (fr) *	1992-10-02	1994-12-23	Adir	Nouveaux dérivés d'ellipticine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
AU666416B2 (en) *	1993-01-29	1996-02-08	Tanabe Seiyaku Co., Ltd.	Ellipticine derivative and process for preparing the same

1996
- 1996-12-30 FR FR9616165A patent/FR2757859B1/fr not_active Expired - Fee Related
1997
- 1997-12-22 EP EP97403121A patent/EP0850940B1/de not_active Expired - Lifetime
- 1997-12-22 PT PT97403121T patent/PT850940E/pt unknown
- 1997-12-22 DE DE69704840T patent/DE69704840T2/de not_active Expired - Fee Related
- 1997-12-22 AT AT97403121T patent/ATE201208T1/de not_active IP Right Cessation
- 1997-12-22 DK DK97403121T patent/DK0850940T3/da active
- 1997-12-22 ES ES97403121T patent/ES2159098T3/es not_active Expired - Lifetime
- 1997-12-24 NZ NZ329510A patent/NZ329510A/xx unknown
- 1997-12-29 NO NO976106A patent/NO309655B1/no not_active IP Right Cessation
- 1997-12-29 HU HU9702542A patent/HUP9702542A3/hu unknown
- 1997-12-29 US US08/999,364 patent/US6162811A/en not_active Expired - Fee Related
- 1997-12-29 CA CA002227506A patent/CA2227506A1/fr not_active Abandoned
- 1997-12-29 PL PL97324069A patent/PL324069A1/xx unknown
- 1997-12-30 BR BR9706497A patent/BR9706497A/pt not_active IP Right Cessation
- 1997-12-30 AU AU49305/97A patent/AU736292B2/en not_active Ceased
- 1997-12-30 ZA ZA9711709A patent/ZA9711709B/xx unknown
1998
- 1998-01-05 JP JP10000065A patent/JPH10195074A/ja active Pending
2001
- 2001-07-19 GR GR20010401094T patent/GR3036245T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ329510A (en)	1998-10-28
NO976106D0 (no)	1997-12-29
BR9706497A (pt)	1999-05-18
AU736292B2 (en)	2001-07-26
ZA9711709B (en)	1998-06-25
EP0850940B1 (de)	2001-05-16
PT850940E (pt)	2001-09-28
CA2227506A1 (fr)	1998-06-30
DK0850940T3 (da)	2001-08-20
HU9702542D0 (en)	1998-03-02
NO976106L (no)	1998-07-01
HUP9702542A3 (en)	1998-11-30
JPH10195074A (ja)	1998-07-28
ATE201208T1 (de)	2001-06-15
GR3036245T3 (en)	2001-10-31
ES2159098T3 (es)	2001-09-16
US6162811A (en)	2000-12-19
EP0850940A1 (de)	1998-07-01
AU4930597A (en)	1998-07-02
DE69704840T2 (de)	2001-12-20
DE69704840D1 (de)	2001-06-21
FR2757859B1 (fr)	1999-01-29
HUP9702542A2 (hu)	1998-08-28
PL324069A1 (en)	1998-07-06
FR2757859A1 (fr)	1998-07-03

Legal Events

Date	Code	Title	Description
2005-09-12	MM1K	Lapsed by not paying the annual fees

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