NO973442L - Nye bismidforbindelser, fremgangsmåte ved fremstilling derav og farmasöytiske sammensetninger inneholdende slike - Google Patents

Nye bismidforbindelser, fremgangsmåte ved fremstilling derav og farmasöytiske sammensetninger inneholdende slike Download PDF

Info

Publication number: NO973442L
Authority: NO; Norway
Prior art keywords: formula; compound; substituted; branched; unsubstituted
Prior art date: 1996-07-26

Application number

NO973442A

Other languages

English (en)

Norwegian (no)

Other versions

NO973442D0 (no

Inventor

Gilbert Lavielle

Patrick Hautefaye

Ghanem Atassi

Alain Pierre

Laurence Kraus-Berthier

Stephane Leonce

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.)

1996-07-26

Filing date

1997-07-25

Publication date

1998-01-27

1997-07-25 Application filed by Adir filed Critical Adir

1997-07-25 Publication of NO973442D0 publication Critical patent/NO973442D0/no

1998-01-27 Publication of NO973442L publication Critical patent/NO973442L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 106
238000000034 method Methods 0.000 title claims description 73
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
-1 1,4-dioxo-1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 9
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 9
125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 68
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 30
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 7
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
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238000000926 separation method Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000006524 alkoxy alkyl amino group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
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238000006243 chemical reaction Methods 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
150000002475 indoles Chemical class 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
239000002246 antineoplastic agent Substances 0.000 claims 1
229940041181 antineoplastic drug Drugs 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract description 5
229910052717 sulfur Inorganic materials 0.000 abstract description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
239000000047 product Substances 0.000 description 99
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238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
238000004452 microanalysis Methods 0.000 description 20
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
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206010028980 Neoplasm Diseases 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
125000004554 carbazol-2-yl group Chemical group C1=C(C=CC=2C3=CC=CC=C3NC12)* 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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239000002244 precipitate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
KKBNYCNHSBKGPP-UHFFFAOYSA-N fluorene-1,3-dione Chemical compound C1=CC=C2C3=CC(=O)CC(=O)C3=CC2=C1 KKBNYCNHSBKGPP-UHFFFAOYSA-N 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 2
UIWPGAOMPJRTRR-UHFFFAOYSA-N 10-nitronaphtho[1,2-e][2]benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=C2C3=CC([N+](=O)[O-])=CC=C3C=CC2=C1 UIWPGAOMPJRTRR-UHFFFAOYSA-N 0.000 description 2
LCPBYTRLYBMSAN-UHFFFAOYSA-N 2-ethenyl-1-methylindole Chemical compound C1=CC=C2N(C)C(C=C)=CC2=C1 LCPBYTRLYBMSAN-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
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125000003277 amino group Chemical group 0.000 description 2
230000001028 anti-proliverative effect Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
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239000013078 crystal Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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NYJBOURKACHGSL-UHFFFAOYSA-N (5-methoxy-1-methylindol-2-yl)methanol Chemical compound COC1=CC=C2N(C)C(CO)=CC2=C1 NYJBOURKACHGSL-UHFFFAOYSA-N 0.000 description 1
IBNGPIOSWCMJGG-UHFFFAOYSA-N 1-methylindole-2-carbaldehyde Chemical compound C1=CC=C2N(C)C(C=O)=CC2=C1 IBNGPIOSWCMJGG-UHFFFAOYSA-N 0.000 description 1
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KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
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VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
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GJEKNELSXNSYAQ-UHFFFAOYSA-N 6,7-dihydro-5h-1-benzothiophen-4-one Chemical compound O=C1CCCC2=C1C=CS2 GJEKNELSXNSYAQ-UHFFFAOYSA-N 0.000 description 1
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QVYKMYOGNITWKJ-UHFFFAOYSA-N 6-methoxy-2-methoxycarbonyl-1,9-dimethylcarbazole-3-carboxylic acid Chemical compound CN1C2=CC=C(OC)C=C2C2=C1C(C)=C(C(=O)OC)C(C(O)=O)=C2 QVYKMYOGNITWKJ-UHFFFAOYSA-N 0.000 description 1
IRMRMSGAOFPVII-UHFFFAOYSA-N 6-methoxy-3-methoxycarbonyl-1,9-dimethylcarbazole-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N(C)C2=C1C=C(C(=O)OC)C(C(O)=O)=C2C IRMRMSGAOFPVII-UHFFFAOYSA-N 0.000 description 1
DYFUZRHAIDQJRD-UHFFFAOYSA-N 6-methoxy-9,10-dimethylfuro[3,4-b]carbazole-1,3-dione Chemical compound C1=C2C3=CC(OC)=CC=C3N(C)C2=C(C)C2=C1C(=O)OC2=O DYFUZRHAIDQJRD-UHFFFAOYSA-N 0.000 description 1
GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 1
NOSSETIZTQQORJ-UHFFFAOYSA-N 9-methoxy-5,6-dihydrobenzo[h]chromen-2-one Chemical compound C1=CC(=O)OC2=C1CCC1=CC=C(OC)C=C12 NOSSETIZTQQORJ-UHFFFAOYSA-N 0.000 description 1
DCJNFMOXPPATOO-UHFFFAOYSA-N 9-methyl-6-nitrocarbazole-3,4-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2N(C)C3=CC=C([N+]([O-])=O)C=C3C2=C1C(O)=O DCJNFMOXPPATOO-UHFFFAOYSA-N 0.000 description 1
STWPQCFNHWTVMW-UHFFFAOYSA-N C1=CC2=CC=C3SC=CC3=C2C2=C1C(=O)OC2=O Chemical compound C1=CC2=CC=C3SC=CC3=C2C2=C1C(=O)OC2=O STWPQCFNHWTVMW-UHFFFAOYSA-N 0.000 description 1
IYNWKSMOVZOALD-UHFFFAOYSA-N C1=CC=C2N(C)C3=C(C(=O)OC)C(C(=O)OC)CC=C3C2=C1 Chemical compound C1=CC=C2N(C)C3=C(C(=O)OC)C(C(=O)OC)CC=C3C2=C1 IYNWKSMOVZOALD-UHFFFAOYSA-N 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
208000012766 Growth delay Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
241001529936 Murinae Species 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
229910017912 NH2OH Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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FDHVXGNWIDUBGD-UHFFFAOYSA-N [O].CCO Chemical compound [O].CCO FDHVXGNWIDUBGD-UHFFFAOYSA-N 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
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239000011668 ascorbic acid Substances 0.000 description 1
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230000009286 beneficial effect Effects 0.000 description 1
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KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
JUGGGTWXNOOGNX-UHFFFAOYSA-N dichloromethane;methanesulfonic acid Chemical compound ClCCl.CS(O)(=O)=O JUGGGTWXNOOGNX-UHFFFAOYSA-N 0.000 description 1
MNHPXYHNTBFBMA-UHFFFAOYSA-N dimethyl 3,4-dihydrodibenzothiophene-1,2-dicarboxylate Chemical compound S1C2=CC=CC=C2C2=C1CCC(C(=O)OC)=C2C(=O)OC MNHPXYHNTBFBMA-UHFFFAOYSA-N 0.000 description 1
UOASXNYYUFEJQA-UHFFFAOYSA-N dimethyl 6-methoxy-1,9-dimethylcarbazole-2,3-dicarboxylate Chemical compound C12=CC(OC)=CC=C2N(C)C2=C1C=C(C(=O)OC)C(C(=O)OC)=C2C UOASXNYYUFEJQA-UHFFFAOYSA-N 0.000 description 1
BMJFPPCQCZDBOO-UHFFFAOYSA-N dimethyl 6-nitrophenanthrene-3,4-dicarboxylate Chemical compound C1=C([N+]([O-])=O)C=C2C3=C(C(=O)OC)C(C(=O)OC)=CC=C3C=CC2=C1 BMJFPPCQCZDBOO-UHFFFAOYSA-N 0.000 description 1
JXHJZUCQQBSNTH-UHFFFAOYSA-N dimethyl 9-methyl-3,4-dihydrocarbazole-1,2-dicarboxylate Chemical compound C12=CC=CC=C2N(C)C2=C1CCC(C(=O)OC)=C2C(=O)OC JXHJZUCQQBSNTH-UHFFFAOYSA-N 0.000 description 1
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
IULVZBJVBQFSFM-UHFFFAOYSA-N dimethyl dibenzofuran-1,2-dicarboxylate Chemical compound C1=CC=C2C3=C(C(=O)OC)C(C(=O)OC)=CC=C3OC2=C1 IULVZBJVBQFSFM-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
BCQZYUOYVLJOPE-UHFFFAOYSA-N ethane-1,2-diamine;dihydrobromide Chemical compound Br.Br.NCCN BCQZYUOYVLJOPE-UHFFFAOYSA-N 0.000 description 1
LQSDRYMXLWVXEL-UHFFFAOYSA-M ethoxycarbonyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(=O)OCC)C1=CC=CC=C1 LQSDRYMXLWVXEL-UHFFFAOYSA-M 0.000 description 1
QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005917 in vivo anti-tumor Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
ISWNAMNOYHCTSB-UHFFFAOYSA-N methanamine;hydrobromide Chemical compound [Br-].[NH3+]C ISWNAMNOYHCTSB-UHFFFAOYSA-N 0.000 description 1
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
OXXJVMUTSUYQBR-UHFFFAOYSA-N methyl 5-methoxy-1h-indole-2-carboxylate Chemical compound COC1=CC=C2NC(C(=O)OC)=CC2=C1 OXXJVMUTSUYQBR-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
230000002438 mitochondrial effect Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
VZOSZWLVPBRSKT-UHFFFAOYSA-N naphtho[1,2-e][2]benzofuran-1,3-dione Chemical compound C1=CC2=CC=C3C=CC=CC3=C2C2=C1C(=O)OC2=O VZOSZWLVPBRSKT-UHFFFAOYSA-N 0.000 description 1
DOUQHYUWLTYTIV-UHFFFAOYSA-N naphtho[1,2-f][2]benzofuran-8,10-dione Chemical compound C1=CC=C2C(C=C3C(=O)OC(C3=C3)=O)=C3C=CC2=C1 DOUQHYUWLTYTIV-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
238000011580 nude mouse model Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000011593 sulfur Chemical group 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
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
HVZIHIRYAVCVRQ-UHFFFAOYSA-N tert-butyl 3-(7-methoxy-1-oxo-3,4-dihydronaphthalen-2-ylidene)propanoate Chemical compound C1CC(=CCC(=O)OC(C)(C)C)C(=O)C2=CC(OC)=CC=C21 HVZIHIRYAVCVRQ-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

NO973442A 1996-07-26 1997-07-25 Nye bismidforbindelser, fremgangsmåte ved fremstilling derav og farmasöytiske sammensetninger inneholdende slike NO973442L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9609417A FR2751655B1 (fr)	1996-07-26	1996-07-26	Nouveaux derives de bis-imides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number	Publication Date
NO973442D0 NO973442D0 (no)	1997-07-25
NO973442L true NO973442L (no)	1998-01-27

Family

ID=9494507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO973442A NO973442L (no)	1996-07-26	1997-07-25	Nye bismidforbindelser, fremgangsmåte ved fremstilling derav og farmasöytiske sammensetninger inneholdende slike

Country Status (19)

Country	Link
US (3)	US5854273A (de)
EP (1)	EP0820985B1 (de)
JP (1)	JPH1067750A (de)
CN (1)	CN1182086A (de)
AT (1)	ATE195936T1 (de)
AU (1)	AU714805B2 (de)
BR (1)	BR9704113A (de)
CA (1)	CA2213054C (de)
DE (1)	DE69702955T2 (de)
DK (1)	DK0820985T3 (de)
ES (1)	ES2150746T3 (de)
FR (1)	FR2751655B1 (de)
GR (1)	GR3034748T3 (de)
HU (1)	HU222730B1 (de)
NO (1)	NO973442L (de)
NZ (1)	NZ328432A (de)
PL (1)	PL321309A1 (de)
PT (1)	PT820985E (de)
ZA (1)	ZA976659B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003063561A1 (en) *	2002-01-24	2003-07-31	Mitsubishi Materials Corporation	Printed-circuit board, electronic part having shield structure, and radio communication apparatus
WO2013024363A1 (en) *	2011-08-17	2013-02-21	Dow Global Technologies Llc	Biorenewable biodegradable surfactants
CN106432190B (zh) *	2015-08-04	2019-04-30	大连理工大学	一类含2-氨基嘧啶的萘酰亚胺化合物，其制备方法及应用
CN106279106B (zh) *	2016-08-10	2018-11-09	大连理工大学	一类侧链含异喹啉的1,8-萘酐类衍生物及其合成和应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3873567A (en) *	1968-09-05	1975-03-25	Universal Oil Prod Co	N-substituted polybromoaromatic ortho-dicarboximides
DE3738457A1 (de) *	1987-11-12	1989-05-24	Lentia Gmbh	Neue loesliche und/oder schmelzbare polyimide und polyamidimide
US5166204A (en) *	1989-11-01	1992-11-24	Toyama Chemical Co., Ltd.	Isoindole derivatives and salts thereof and antitumor agent comprising the same
EP0523240B1 (de) *	1991-01-21	1996-03-20	MITSUI TOATSU CHEMICALS, Inc.	Bisimidderivate, daraus hergestellte polyimidharze sowie carbonfaser-verstärkte polyimidharze
US5206249A (en) *	1991-03-27	1993-04-27	Du Pont Merck Pharmaceutical Company	Bis-naphthalimides containing amino-acid derived linkers as anticancer agents
US5416089A (en) *	1993-06-24	1995-05-16	The Du Pont Merck Pharmaceutical Company	Polycyclic and heterocyclic chromophores for bis-imide tumoricidals

1996
- 1996-07-26 FR FR9609417A patent/FR2751655B1/fr not_active Expired - Fee Related
1997
- 1997-07-23 US US08/899,289 patent/US5854273A/en not_active Expired - Fee Related
- 1997-07-24 PL PL97321309A patent/PL321309A1/xx unknown
- 1997-07-24 PT PT97401790T patent/PT820985E/pt unknown
- 1997-07-24 DK DK97401790T patent/DK0820985T3/da active
- 1997-07-24 DE DE69702955T patent/DE69702955T2/de not_active Expired - Fee Related
- 1997-07-24 EP EP97401790A patent/EP0820985B1/de not_active Expired - Lifetime
- 1997-07-24 AU AU30173/97A patent/AU714805B2/en not_active Ceased
- 1997-07-24 AT AT97401790T patent/ATE195936T1/de not_active IP Right Cessation
- 1997-07-24 ES ES97401790T patent/ES2150746T3/es not_active Expired - Lifetime
- 1997-07-25 ZA ZA9706659A patent/ZA976659B/xx unknown
- 1997-07-25 NO NO973442A patent/NO973442L/no unknown
- 1997-07-25 CN CN97104673A patent/CN1182086A/zh active Pending
- 1997-07-25 CA CA002213054A patent/CA2213054C/fr not_active Expired - Fee Related
- 1997-07-25 NZ NZ328432A patent/NZ328432A/en unknown
- 1997-07-25 HU HU9701300A patent/HU222730B1/hu not_active IP Right Cessation
- 1997-07-25 JP JP9199529A patent/JPH1067750A/ja active Pending
- 1997-07-28 BR BR9704113A patent/BR9704113A/pt not_active IP Right Cessation
1998
- 1998-12-28 US US09/221,904 patent/US6162822A/en not_active Expired - Fee Related
2000
- 2000-07-14 US US09/616,857 patent/US6300340B1/en not_active Expired - Fee Related
- 2000-11-02 GR GR20000402436T patent/GR3034748T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
GR3034748T3 (en)	2001-02-28
EP0820985B1 (de)	2000-08-30
JPH1067750A (ja)	1998-03-10
PT820985E (pt)	2000-12-29
PL321309A1 (en)	1998-02-02
ATE195936T1 (de)	2000-09-15
NO973442D0 (no)	1997-07-25
NZ328432A (en)	1997-12-19
ES2150746T3 (es)	2000-12-01
FR2751655B1 (fr)	1998-08-28
HUP9701300A1 (hu)	1999-09-28
HU9701300D0 (en)	1997-09-29
EP0820985A1 (de)	1998-01-28
ZA976659B (en)	1998-02-23
CA2213054C (fr)	2003-05-27
DK0820985T3 (da)	2000-12-18
BR9704113A (pt)	1999-05-18
DE69702955D1 (de)	2000-10-05
CA2213054A1 (fr)	1998-01-26
AU714805B2 (en)	2000-01-13
CN1182086A (zh)	1998-05-20
DE69702955T2 (de)	2001-03-29
US6300340B1 (en)	2001-10-09
FR2751655A1 (fr)	1998-01-30
AU3017397A (en)	1998-02-05
US6162822A (en)	2000-12-19
US5854273A (en)	1998-12-29
HU222730B1 (hu)	2003-09-29

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US5977100A (en)	1999-11-02	Substituted guanidine derivatives, process for production thereof, and pharmaceutical uses thereof
CZ291626B6 (cs)	2003-04-16	Tricyklické sloučeniny, způsob výroby a použití
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