NO309935B1 - Nye bis-pyrido[4,3-b]karbazolforbindelser, en fremgangsmÕte ved deres fremstilling og farmasøytiske sammensetninger som inneholder disse - Google Patents

Nye bis-pyrido[4,3-b]karbazolforbindelser, en fremgangsmÕte ved deres fremstilling og farmasøytiske sammensetninger som inneholder disse Download PDF

Info

Publication number: NO309935B1
Authority: NO; Norway
Prior art keywords: pyrido; carbon atoms; compounds; compound; formula
Prior art date: 1997-08-06

Application number

NO983602A

Other languages

English (en)

Norwegian (no)

Other versions

NO983602D0 (no

NO983602L (no

Inventor

Claude Guillonneau

Yves Charton

Ghonem 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.)

1997-08-06

Filing date

1998-08-05

Publication date

2001-04-23

1998-08-05 Application filed by Adir filed Critical Adir

1998-08-05 Publication of NO983602D0 publication Critical patent/NO983602D0/no

1999-02-08 Publication of NO983602L publication Critical patent/NO983602L/no

2001-04-23 Publication of NO309935B1 publication Critical patent/NO309935B1/no

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
238000000034 method Methods 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims abstract description 9
239000002253 acid Substances 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
150000001204 N-oxides Chemical class 0.000 claims abstract description 3
230000003287 optical effect Effects 0.000 claims abstract description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 25
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
230000000259 anti-tumor effect Effects 0.000 claims description 7
229960000250 adipic acid Drugs 0.000 claims description 5
235000011037 adipic acid Nutrition 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 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
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
239000004215 Carbon black (E152) Substances 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
206010028980 Neoplasm Diseases 0.000 description 8
ZIXGXMMUKPLXBB-UHFFFAOYSA-N Olivacine Chemical compound N1C2=CC=CC=C2C2=C1C(C)=C1C=CN=C(C)C1=C2 ZIXGXMMUKPLXBB-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical group 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 4
241001529936 Murinae Species 0.000 description 4
231100000135 cytotoxicity Toxicity 0.000 description 4
230000003013 cytotoxicity Effects 0.000 description 4
CTSPAMFJBXKSOY-UHFFFAOYSA-N ellipticine Chemical compound N1=CC=C2C(C)=C(NC=3C4=CC=CC=3)C4=C(C)C2=C1 CTSPAMFJBXKSOY-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
-1 hexafluorophosphate Chemical compound 0.000 description 3
201000001441 melanoma Diseases 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940009456 adriamycin Drugs 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
231100000433 cytotoxic Toxicity 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
230000007774 longterm Effects 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
210000003200 peritoneal cavity Anatomy 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000007858 starting material 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
125000003831 tetrazolyl group Chemical group 0.000 description 2
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
ZNMDSQBHOLGTPA-UHFFFAOYSA-N 2,2,5,5-tetramethylhexanedioic acid Chemical compound OC(=O)C(C)(C)CCC(C)(C)C(O)=O ZNMDSQBHOLGTPA-UHFFFAOYSA-N 0.000 description 1
HUOXNKQMXIKHRJ-UHFFFAOYSA-N 2-[1-[2-[1-[2-(dimethylamino)ethylcarbamoyl]-5,6-dimethylpyrido[4,3-b]carbazol-9-yl]oxy-2-oxoethyl]cyclohexyl]acetic acid Chemical compound C1=C2C=3C=C4C(C(=O)NCCN(C)C)=NC=CC4=C(C)C=3N(C)C2=CC=C1OC(=O)CC1(CC(O)=O)CCCCC1 HUOXNKQMXIKHRJ-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
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
208000008342 Leukemia P388 Diseases 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 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
239000012980 RPMI-1640 medium Substances 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000032823 cell division Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000035572 chemosensitivity Effects 0.000 description 1
238000007398 colorimetric assay Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000002254 cytotoxic agent Substances 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
239000012634 fragment Substances 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
239000001963 growth medium Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000005917 in vivo anti-tumor Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229940087646 methanolamine Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 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
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO983602A 1997-08-06 1998-08-05 Nye bis-pyrido[4,3-b]karbazolforbindelser, en fremgangsmÕte ved deres fremstilling og farmasøytiske sammensetninger som inneholder disse NO309935B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9710066A FR2767132B1 (fr)	1997-08-06	1997-08-06	Nouveaux composes de bis pyrido [4,3-b] carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (3)

Publication Number	Publication Date
NO983602D0 NO983602D0 (no)	1998-08-05
NO983602L NO983602L (no)	1999-02-08
NO309935B1 true NO309935B1 (no)	2001-04-23

Family

ID=9510082

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO983602A NO309935B1 (no)	1997-08-06	1998-08-05	Nye bis-pyrido[4,3-b]karbazolforbindelser, en fremgangsmÕte ved deres fremstilling og farmasøytiske sammensetninger som inneholder disse

Country Status (19)

Country	Link
US (1)	US5958938A (xx)
EP (1)	EP0895995B1 (xx)
JP (1)	JPH11100379A (xx)
CN (1)	CN1087018C (xx)
AT (1)	ATE218574T1 (xx)
AU (1)	AU737770B2 (xx)
BR (1)	BR9802850A (xx)
CA (1)	CA2244508C (xx)
DE (1)	DE69805709T2 (xx)
DK (1)	DK0895995T3 (xx)
ES (1)	ES2178128T3 (xx)
FR (1)	FR2767132B1 (xx)
HK (1)	HK1017686A1 (xx)
HU (1)	HUP9801822A3 (xx)
NO (1)	NO309935B1 (xx)
NZ (1)	NZ331267A (xx)
PL (1)	PL327873A1 (xx)
PT (1)	PT895995E (xx)
ZA (1)	ZA987076B (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102584679B (zh) *	2011-01-13	2015-06-17	中国科学院上海药物研究所	一类苯并咔唑酰胺类化合物、其制备方法和用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2696465B1 (fr) *	1992-10-02	1994-12-23	Adir	Nouveaux dérivés d'ellipticine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.

1997
- 1997-08-06 FR FR9710066A patent/FR2767132B1/fr not_active Expired - Fee Related
1998
- 1998-07-22 US US09/120,899 patent/US5958938A/en not_active Expired - Fee Related
- 1998-08-03 JP JP10218957A patent/JPH11100379A/ja active Pending
- 1998-08-04 EP EP98401979A patent/EP0895995B1/fr not_active Expired - Lifetime
- 1998-08-04 PT PT98401979T patent/PT895995E/pt unknown
- 1998-08-04 ES ES98401979T patent/ES2178128T3/es not_active Expired - Lifetime
- 1998-08-04 DK DK98401979T patent/DK0895995T3/da active
- 1998-08-04 AT AT98401979T patent/ATE218574T1/de not_active IP Right Cessation
- 1998-08-04 DE DE69805709T patent/DE69805709T2/de not_active Expired - Fee Related
- 1998-08-05 CN CN98118007A patent/CN1087018C/zh not_active Expired - Fee Related
- 1998-08-05 NO NO983602A patent/NO309935B1/no unknown
- 1998-08-05 BR BR9802850-2A patent/BR9802850A/pt not_active IP Right Cessation
- 1998-08-05 NZ NZ331267A patent/NZ331267A/xx unknown
- 1998-08-05 CA CA002244508A patent/CA2244508C/fr not_active Expired - Fee Related
- 1998-08-06 HU HU9801822A patent/HUP9801822A3/hu unknown
- 1998-08-06 AU AU78836/98A patent/AU737770B2/en not_active Ceased
- 1998-08-06 PL PL98327873A patent/PL327873A1/xx not_active IP Right Cessation
- 1998-08-06 ZA ZA987076A patent/ZA987076B/xx unknown
1999
- 1999-07-05 HK HK99102827A patent/HK1017686A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU7883698A (en)	1999-02-18
PT895995E (pt)	2002-09-30
US5958938A (en)	1999-09-28
HUP9801822A2 (hu)	1999-04-28
HUP9801822A3 (en)	2000-01-28
CN1087018C (zh)	2002-07-03
FR2767132B1 (fr)	1999-09-10
CN1207393A (zh)	1999-02-10
DE69805709T2 (de)	2003-01-30
AU737770B2 (en)	2001-08-30
FR2767132A1 (fr)	1999-02-12
JPH11100379A (ja)	1999-04-13
ES2178128T3 (es)	2002-12-16
EP0895995B1 (fr)	2002-06-05
PL327873A1 (en)	1999-02-15
EP0895995A1 (fr)	1999-02-10
CA2244508C (fr)	2003-04-01
ZA987076B (en)	1999-02-08
CA2244508A1 (fr)	1999-02-06
NZ331267A (en)	1999-07-29
HU9801822D0 (en)	1998-10-28
HK1017686A1 (en)	1999-11-26
DE69805709D1 (de)	2002-07-11
NO983602D0 (no)	1998-08-05
BR9802850A (pt)	2000-02-08
NO983602L (no)	1999-02-08
ATE218574T1 (de)	2002-06-15
DK0895995T3 (da)	2002-09-09

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