SK1672002A3 - Ascididemin derivative, method for the preparation thereof and pharmaceutical composition containing the same - Google Patents

Ascididemin derivative, method for the preparation thereof and pharmaceutical composition containing the same Download PDF

Info

Publication number: SK1672002A3
Authority: SK; Slovakia
Prior art keywords: pyrido; alkyl; phenanthrolin; formula; compounds
Prior art date: 1999-08-13

Application number

SK167-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Evelyne Delfourne

Francis Darro

Jean Bastide

Robert Kiss

Armand Frydman

Original Assignee

Lafon Labor

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

1999-08-13

Filing date

2000-08-11

Publication date

2002-10-08

2000-08-11 Application filed by Lafon Labor filed Critical Lafon Labor

2002-10-08 Publication of SK1672002A3 publication Critical patent/SK1672002A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 31
BTAIBIXHXSXUFN-UHFFFAOYSA-N ascididemine Chemical class C1=CC=CC2=NC(C(=O)C=3C4=NC=CC=3)=C3C4=NC=CC3=C21 BTAIBIXHXSXUFN-UHFFFAOYSA-N 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 116
206010028980 Neoplasm Diseases 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 34
238000011282 treatment Methods 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
-1 hydroxy, methoxy Chemical group 0.000 claims description 14
ULSFNUQXUHMWNZ-UHFFFAOYSA-N crl-8401 Chemical compound O=C1C2=NC=CC=C2C2=NC=CC3=C2C1=NC=C3OC ULSFNUQXUHMWNZ-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
201000011510 cancer Diseases 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
239000002246 antineoplastic agent Substances 0.000 claims description 6
229940041181 antineoplastic drug Drugs 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
PSBOMJUFAJVWQH-UHFFFAOYSA-N 3h-1,10-phenanthrolin-4-one Chemical compound C1=CC2=CC=CN=C2C2=C1C(=O)CC=N2 PSBOMJUFAJVWQH-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
150000002081 enamines Chemical class 0.000 claims description 4
206010027476 Metastases Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
PRRCPGPQYCZMFC-UHFFFAOYSA-N chembl117616 Chemical compound C1=NC(C(=O)C=2C(Cl)=CC=NC=22)=C3C2=NC=CC3=C1 PRRCPGPQYCZMFC-UHFFFAOYSA-N 0.000 claims description 3
WCRIHVQLNYDYHQ-UHFFFAOYSA-N chembl117784 Chemical compound C1=NC(C=2C(OC)=CC=NC=2C2=O)=C3C2=NC=CC3=C1 WCRIHVQLNYDYHQ-UHFFFAOYSA-N 0.000 claims description 3
JOBZJDOSNDFONB-UHFFFAOYSA-N chembl118655 Chemical compound O=C1C2=CC=CN=C2C2=NC=CC3=C2C1=NC=C3OC JOBZJDOSNDFONB-UHFFFAOYSA-N 0.000 claims description 3
NXHFYTNPRXAFAC-UHFFFAOYSA-N chembl119037 Chemical compound C1=NC(C2=CC=C(N=C2C2=O)OC)=C3C2=NC=CC3=C1 NXHFYTNPRXAFAC-UHFFFAOYSA-N 0.000 claims description 3
MAOQMONYODZXHW-UHFFFAOYSA-N chembl119700 Chemical compound C1=NC(C=2C(OC)=CC=NC=2C2=O)=C3C2=NC=C(OC)C3=C1 MAOQMONYODZXHW-UHFFFAOYSA-N 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
MNXMECIIHHPDEQ-UHFFFAOYSA-N C12=NC=CC=C2C(=O)C2=NC=CC3=C2C1=NC=C3COC(=O)C Chemical compound C12=NC=CC=C2C(=O)C2=NC=CC3=C2C1=NC=C3COC(=O)C MNXMECIIHHPDEQ-UHFFFAOYSA-N 0.000 claims description 2
PDOBVGYECFRRLB-UHFFFAOYSA-N C1=NC(C2=CC=C(N=C2C2=O)OC)=C3C2=NC=CC3=C1COC(C)=O Chemical compound C1=NC(C2=CC=C(N=C2C2=O)OC)=C3C2=NC=CC3=C1COC(C)=O PDOBVGYECFRRLB-UHFFFAOYSA-N 0.000 claims description 2
GCEVQZHJMWWOCK-UHFFFAOYSA-N O=C1C2=CC=CN=C2C2=NC(CCCl)=CC3=CC=NC1=C32 Chemical compound O=C1C2=CC=CN=C2C2=NC(CCCl)=CC3=CC=NC1=C32 GCEVQZHJMWWOCK-UHFFFAOYSA-N 0.000 claims description 2
229910006069 SO3H Inorganic materials 0.000 claims description 2
WZUNGQKHNMOASU-UHFFFAOYSA-N chembl118709 Chemical compound C1=NC(C=2N=CC=C(C=2C2=O)OC)=C3C2=NC=C(OC)C3=C1 WZUNGQKHNMOASU-UHFFFAOYSA-N 0.000 claims description 2
LPXZPIDBMLWYEL-UHFFFAOYSA-N chembl331562 Chemical compound C1=NC(C2=C(OC)C=C(N=C2C2=O)OC)=C3C2=NC=CC3=C1 LPXZPIDBMLWYEL-UHFFFAOYSA-N 0.000 claims description 2
CGMJZZIYLGQIJU-UHFFFAOYSA-N chembl333433 Chemical compound C1=NC(C=2N=CC=C(C=2C2=O)OC)=C3C2=NC=CC3=C1 CGMJZZIYLGQIJU-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
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 2
150000002431 hydrogen Chemical class 0.000 claims 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
PONNDSQDLDAFPN-UHFFFAOYSA-N C12=CC=CN=C2C(=O)C2=NC=CC3=C2C1=NC=C3COC(=O)C Chemical compound C12=CC=CN=C2C(=O)C2=NC=CC3=C2C1=NC=C3COC(=O)C PONNDSQDLDAFPN-UHFFFAOYSA-N 0.000 claims 1
VCOCBRFBXVKSNT-UHFFFAOYSA-N C1=NC(C2=NC=C(C=C2C2=O)OC)=C3C2=NC=CC3=C1COC(C)=O Chemical compound C1=NC(C2=NC=C(C=C2C2=O)OC)=C3C2=NC=CC3=C1COC(C)=O VCOCBRFBXVKSNT-UHFFFAOYSA-N 0.000 claims 1
JVQJKRCLEYXCCM-UHFFFAOYSA-N COC1=CN=C2C(C=3C=4C(=CC=NC4C2=C1)C=CN3)=O Chemical compound COC1=CN=C2C(C=3C=4C(=CC=NC4C2=C1)C=CN3)=O JVQJKRCLEYXCCM-UHFFFAOYSA-N 0.000 claims 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
TXCBSNDMDYCWTP-UHFFFAOYSA-N O=C1C2=NC=CC=C2C2=NC(CCCl)=CC3=CC=NC1=C32 Chemical compound O=C1C2=NC=CC=C2C2=NC(CCCl)=CC3=CC=NC1=C32 TXCBSNDMDYCWTP-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
239000000824 cytostatic agent Substances 0.000 claims 1
230000001085 cytostatic effect Effects 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
230000001472 cytotoxic effect Effects 0.000 abstract description 12
230000000259 anti-tumor effect Effects 0.000 abstract description 8
229940079593 drug Drugs 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 6
230000001225 therapeutic effect Effects 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 144
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
239000011541 reaction mixture Substances 0.000 description 49
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
239000000843 powder Substances 0.000 description 46
239000000243 solution Substances 0.000 description 46
239000000047 product Substances 0.000 description 44
239000000377 silicon dioxide Substances 0.000 description 36
238000001704 evaporation Methods 0.000 description 32
239000002904 solvent Substances 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
230000008020 evaporation Effects 0.000 description 29
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
241000699670 Mus sp. Species 0.000 description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
238000003818 flash chromatography Methods 0.000 description 26
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 24
229910052943 magnesium sulfate Inorganic materials 0.000 description 23
235000019341 magnesium sulphate Nutrition 0.000 description 23
210000004027 cell Anatomy 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000001914 filtration Methods 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
230000004083 survival effect Effects 0.000 description 15
235000019270 ammonium chloride Nutrition 0.000 description 14
241000699666 Mus <mouse, genus> Species 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 10
241001465754 Metazoa Species 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
239000007924 injection Substances 0.000 description 10
238000002347 injection Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 10
206010006187 Breast cancer Diseases 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000001035 drying Methods 0.000 description 9
238000001727 in vivo Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
238000011081 inoculation Methods 0.000 description 8
208000026310 Breast neoplasm Diseases 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
150000007857 hydrazones Chemical class 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
208000032839 leukemia Diseases 0.000 description 6
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 6
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 6
238000002390 rotary evaporation Methods 0.000 description 6
238000005406 washing Methods 0.000 description 6
CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 5
229920000858 Cyclodextrin Polymers 0.000 description 5
206010025323 Lymphomas Diseases 0.000 description 5
229930013930 alkaloid Natural products 0.000 description 5
208000029742 colonic neoplasm Diseases 0.000 description 5
208000020816 lung neoplasm Diseases 0.000 description 5
231100000682 maximum tolerated dose Toxicity 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 5
206010009944 Colon cancer Diseases 0.000 description 4
208000001333 Colorectal Neoplasms Diseases 0.000 description 4
241000195493 Cryptophyta Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
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206010058467 Lung neoplasm malignant Diseases 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229940126214 compound 3 Drugs 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
201000005202 lung cancer Diseases 0.000 description 4
UMPXJANEVODDAQ-UHFFFAOYSA-N pyrido[3,2-g]quinoline-5,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CN=C3C(=O)C2=N1 UMPXJANEVODDAQ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
210000004881 tumor cell Anatomy 0.000 description 4
JXTKZMFPFKZRHP-UHFFFAOYSA-N 1h-quinoline-2,5,8-trione Chemical compound N1C(=O)C=CC2=C1C(=O)C=CC2=O JXTKZMFPFKZRHP-UHFFFAOYSA-N 0.000 description 3
UDHVVNSXRJFTNQ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyrido[3,2-g]quinoline-5,10-dione Chemical compound O=C1C2=NC(Cl)=CC(Cl)=C2C(=O)C2=C1N=CC=C2C UDHVVNSXRJFTNQ-UHFFFAOYSA-N 0.000 description 3
SSAYWQXYCRZAGM-UHFFFAOYSA-N 2,7-dimethoxy-6-methylpyrido[3,2-g]quinoline-5,10-dione Chemical compound COC1=CN=C2C(=O)C3=NC(OC)=CC=C3C(=O)C2=C1C SSAYWQXYCRZAGM-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 3
206010061535 Ovarian neoplasm Diseases 0.000 description 3
206010060862 Prostate cancer Diseases 0.000 description 3
208000000236 Prostatic Neoplasms Diseases 0.000 description 3
208000015634 Rectal Neoplasms Diseases 0.000 description 3
150000003797 alkaloid derivatives Chemical class 0.000 description 3
210000001072 colon Anatomy 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
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230000012010 growth Effects 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000010502 orange oil Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
MCTCVKDGNCPADW-UHFFFAOYSA-N 11-hydroxyascididemin Chemical compound N1C=CC(=O)C(C2=O)=C1C1=C3C2=NC2=CC=CC=C2C3=CC=N1 MCTCVKDGNCPADW-UHFFFAOYSA-N 0.000 description 2
NTQVHSNITSRSEE-UHFFFAOYSA-N 12-(dimethylamino)-6,10,16-triazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17),14-octaen-8-one Chemical compound O=C1C2=NC=CC=C2C2=NC=CC3=C2C1=NC=C3N(C)C NTQVHSNITSRSEE-UHFFFAOYSA-N 0.000 description 2
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OGUUWCWFXRABIF-UHFFFAOYSA-N 2,4-dimethoxy-6-methylpyrido[3,2-g]quinoline-5,10-dione Chemical compound C1=CN=C2C(=O)C3=NC(OC)=CC(OC)=C3C(=O)C2=C1C OGUUWCWFXRABIF-UHFFFAOYSA-N 0.000 description 2
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RSGRJKHFJKNNCB-UHFFFAOYSA-N 3,6-dimethoxy-4-methylpyrido[3,2-g]quinoline-5,10-dione Chemical compound C1=CC(OC)=C2C(=O)C3=C(C)C(OC)=CN=C3C(=O)C2=N1 RSGRJKHFJKNNCB-UHFFFAOYSA-N 0.000 description 2
AIJPXSNOGNUPPD-UHFFFAOYSA-N 3,7-dimethoxy-4-methylpyrido[2,3-g]quinoline-5,10-dione Chemical compound C1=C(OC)C(C)=C2C(=O)C3=NC(OC)=CC=C3C(=O)C2=N1 AIJPXSNOGNUPPD-UHFFFAOYSA-N 0.000 description 2
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NVJSPQCVDHGYRE-UHFFFAOYSA-N quinoline-5,8-dione Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=N1 NVJSPQCVDHGYRE-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
229910001958 silver carbonate Inorganic materials 0.000 description 1
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
YNJCFDAODGKHAV-UHFFFAOYSA-N tert-butyl n-(2-hydroxypropyl)carbamate Chemical compound CC(O)CNC(=O)OC(C)(C)C YNJCFDAODGKHAV-UHFFFAOYSA-N 0.000 description 1
MLDSDVASYUUDLT-UHFFFAOYSA-N tert-butyl n-(3-oxopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC=O MLDSDVASYUUDLT-UHFFFAOYSA-N 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000004448 titration Methods 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
PKVRCIRHQMSYJX-AIFWHQITSA-N trabectedin Chemical compound C([C@@]1(C(OC2)=O)NCCC3=C1C=C(C(=C3)O)OC)S[C@@H]1C3=C(OC(C)=O)C(C)=C4OCOC4=C3[C@H]2N2[C@@H](O)[C@H](CC=3C4=C(O)C(OC)=C(C)C=3)N(C)[C@H]4[C@@H]21 PKVRCIRHQMSYJX-AIFWHQITSA-N 0.000 description 1
229960000977 trabectedin Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

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

SK167-2002A 1999-08-13 2000-08-11 Ascididemin derivative, method for the preparation thereof and pharmaceutical composition containing the same SK1672002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9910493A FR2797446B1 (fr)	1999-08-13	1999-08-13	Derives de phenanthroline-7-ones et leurs applications en therapeutique
PCT/FR2000/002313 WO2001012632A2 (fr)	1999-08-13	2000-08-11	Derives de phenanthroline-7-ones et leurs applications en therapeutique

Publications (1)

Publication Number	Publication Date
SK1672002A3 true SK1672002A3 (en)	2002-10-08

Family

ID=9549146

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK167-2002A SK1672002A3 (en)	1999-08-13	2000-08-11	Ascididemin derivative, method for the preparation thereof and pharmaceutical composition containing the same

Country Status (21)

Country	Link
US (1)	US6809096B1 (de)
EP (1)	EP1202993B1 (de)
JP (1)	JP2003526627A (de)
KR (1)	KR20020056883A (de)
CN (1)	CN1187352C (de)
AT (1)	ATE307131T1 (de)
AU (1)	AU777689B2 (de)
BR (1)	BR0013239A (de)
CA (1)	CA2381352A1 (de)
CZ (1)	CZ2002529A3 (de)
DE (1)	DE60023307D1 (de)
FR (1)	FR2797446B1 (de)
HU (1)	HUP0203033A3 (de)
IL (1)	IL147901A0 (de)
MX (1)	MXPA02001493A (de)
NO (1)	NO20020669L (de)
NZ (1)	NZ516944A (de)
PL (1)	PL353454A1 (de)
SK (1)	SK1672002A3 (de)
WO (1)	WO2001012632A2 (de)
ZA (1)	ZA200201003B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102012006903B4 (de) *	2012-04-05	2016-06-30	Christian-Albrechts-Universität Zu Kiel	Neue aromatische Heterocyclen, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend neue aromatische Heterocyclen
CA2909091C (en)	2013-04-09	2021-11-02	The Board Of Trustees Of The University Of Illinois	Tumor-selective combination therapy
CN103254191B (zh) *	2013-05-17	2016-01-27	中国人民解放军第二军医大学	取代芳香四环类抗真菌化合物及其制备方法与应用
CN116082332B (zh) *	2022-12-14	2024-12-24	爱斯特（成都）生物制药股份有限公司	一种制备2-苯甲酰基-1,10-菲罗啉的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5182287A (en) *	1989-11-03	1993-01-26	Harbor Branch Oceanographic	Bioactive heterocycle alkaloids and methods of use

1999
- 1999-08-13 FR FR9910493A patent/FR2797446B1/fr not_active Expired - Fee Related
2000
- 2000-08-11 CZ CZ2002529A patent/CZ2002529A3/cs unknown
- 2000-08-11 WO PCT/FR2000/002313 patent/WO2001012632A2/fr not_active Ceased
- 2000-08-11 IL IL14790100A patent/IL147901A0/xx unknown
- 2000-08-11 PL PL00353454A patent/PL353454A1/xx not_active Application Discontinuation
- 2000-08-11 EP EP00958679A patent/EP1202993B1/de not_active Expired - Lifetime
- 2000-08-11 HU HU0203033A patent/HUP0203033A3/hu unknown
- 2000-08-11 NZ NZ516944A patent/NZ516944A/en unknown
- 2000-08-11 BR BR0013239-0A patent/BR0013239A/pt not_active IP Right Cessation
- 2000-08-11 DE DE60023307T patent/DE60023307D1/de not_active Expired - Lifetime
- 2000-08-11 AU AU70125/00A patent/AU777689B2/en not_active Ceased
- 2000-08-11 CA CA002381352A patent/CA2381352A1/fr not_active Abandoned
- 2000-08-11 SK SK167-2002A patent/SK1672002A3/sk unknown
- 2000-08-11 CN CNB008126542A patent/CN1187352C/zh not_active Expired - Fee Related
- 2000-08-11 US US10/049,511 patent/US6809096B1/en not_active Expired - Fee Related
- 2000-08-11 MX MXPA02001493A patent/MXPA02001493A/es unknown
- 2000-08-11 JP JP2001517530A patent/JP2003526627A/ja active Pending
- 2000-08-11 KR KR1020027001753A patent/KR20020056883A/ko not_active Abandoned
- 2000-08-11 AT AT00958679T patent/ATE307131T1/de not_active IP Right Cessation
2002
- 2002-02-05 ZA ZA200201003A patent/ZA200201003B/en unknown
- 2002-02-11 NO NO20020669A patent/NO20020669L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2797446A1 (fr)	2001-02-16
IL147901A0 (en)	2002-08-14
US6809096B1 (en)	2004-10-26
MXPA02001493A (es)	2002-07-02
PL353454A1 (en)	2003-11-17
WO2001012632A3 (fr)	2001-07-19
CN1373761A (zh)	2002-10-09
DE60023307D1 (de)	2006-03-02
ATE307131T1 (de)	2005-11-15
CA2381352A1 (fr)	2001-02-22
FR2797446B1 (fr)	2001-11-02
KR20020056883A (ko)	2002-07-10
NO20020669L (no)	2002-04-15
JP2003526627A (ja)	2003-09-09
HUP0203033A2 (hu)	2003-01-28
HUP0203033A3 (en)	2003-12-29
AU777689B2 (en)	2004-10-28
AU7012500A (en)	2001-03-13
WO2001012632A2 (fr)	2001-02-22
ZA200201003B (en)	2003-10-29
BR0013239A (pt)	2002-04-23
EP1202993B1 (de)	2005-10-19
CN1187352C (zh)	2005-02-02
EP1202993A2 (de)	2002-05-08
CZ2002529A3 (cs)	2002-05-15
NZ516944A (en)	2004-07-30
NO20020669D0 (no)	2002-02-11

Publication	Publication Date	Title
Wall et al.	1993	Plant antitumor agents. 30. Synthesis and structure activity of novel camptothecin analogs
FI91872C (fi)	1994-08-25	Menetelmä terapeuttisesti aktiivisten pyranoindolitsinokinoliinijohdannaisten valmistamiseksi
US5658920A (en)	1997-08-19	Substituted 1H,12H-benz-[DE]pyrano[3',4':6,7] indolizino[1,2-B]quinoline-10,13(9H,15H)-dione compound
KR930009357B1 (ko)	1993-09-28	수용성 캠프토테신 유도체 및 이의 제조방법
IE913790A1 (en)	1992-05-22	SUBSTITUTED INDOLIZINO [1,2-b]QUINOLINONES
SK1672002A3 (en)	2002-10-08	Ascididemin derivative, method for the preparation thereof and pharmaceutical composition containing the same
US6583150B1 (en)	2003-06-24	Pharmaceutical composition based on polyaromatic compounds
DE60013849T2 (de)	2005-02-03	Ascidideminderivate und ihre therapeutische verwendung
DE60309605T2 (de)	2007-09-27	SUBSTITUIERTE i1,4öBENZODIOXINi2,3-EöISOINDOL-DERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND SIE ENTHALTENDE PHARMAZEUTISCHE ZUSAMMENSETZUNGEN
MXPA01009322A (en)	2002-03-26	Pharmaceutical composition based on polyaromatic compounds
WO1995003803A1 (en)	1995-02-09	SUBSTITUTED FURO[3',4':6,7]INDOLIZINO[1,2-b]QUINOLINONES
ZA200200840B (en)	2003-01-30	Ascididemin derivatives and their therapeutic applications.
RS51061B (sr)	2010-10-31	Nova jedinjenja analozi kamptotecina, postupak za njihovu proizvodnju i farmaceutske smeše koje ih sadrže