NO324882B1 - Optisk rene camptotecin analoger, optisk rent mellomprodukt, fremgangsmate for fremstilling av disse, anvendelse og farmasoytisk preparat - Google Patents

Optisk rene camptotecin analoger, optisk rent mellomprodukt, fremgangsmate for fremstilling av disse, anvendelse og farmasoytisk preparat Download PDF

Info

Publication number: NO324882B1
Authority: NO; Norway
Prior art keywords: compound; general formula; represented below; formula; product
Prior art date: 1997-08-29

Application number

NO20000995A

Other languages

English (en)

Norwegian (no)

Other versions

NO20000995D0 (no

NO20000995L (no

Inventor

Jean-Bernard Cazaux

Christine Le Breton

Eric Manginot

Dennis C H Bigg

Olivier Lavergne

Original Assignee

Sod Conseils Rech Applic

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.)

1997-08-29

Filing date

2000-02-28

Publication date

2007-12-27

2000-02-28 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

2000-02-28 Publication of NO20000995D0 publication Critical patent/NO20000995D0/no

2000-02-28 Publication of NO20000995L publication Critical patent/NO20000995L/no

2007-12-27 Publication of NO324882B1 publication Critical patent/NO324882B1/no

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 63
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
239000000203 mixture Substances 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 10
239000012429 reaction media Substances 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 3
235000009518 sodium iodide Nutrition 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
230000000259 anti-tumor effect Effects 0.000 claims description 2
239000003096 antiparasitic agent Substances 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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 claims 1
239000003443 antiviral agent Substances 0.000 claims 1
239000000047 product Substances 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
210000004027 cell Anatomy 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 9
BEIVRAYQIXQZKG-UHFFFAOYSA-N 3-hydroxy-3-[2-methoxy-3-(phenylmethoxymethyl)pyridin-4-yl]pentanoic acid Chemical compound OC(=O)CC(O)(CC)C1=CC=NC(OC)=C1COCC1=CC=CC=C1 BEIVRAYQIXQZKG-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 7
229940127093 camptothecin Drugs 0.000 description 7
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000013019 agitation Methods 0.000 description 6
239000000010 aprotic solvent Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000002609 medium Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
101710183280 Topoisomerase Proteins 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
201000010099 disease Diseases 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000001464 adherent effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000003111 delayed effect Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000011835 investigation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 2
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 2
RVBWWMADTISCJE-UHFFFAOYSA-N 5-ethyl-5-hydroxy-4,8-dihydro-1h-oxepino[3,4-c]pyridine-3,9-dione Chemical compound CCC1(O)CC(=O)OCC2=C1C=CNC2=O RVBWWMADTISCJE-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
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 2
208000030852 Parasitic disease Diseases 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
208000036142 Viral infection Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001028 anti-proliverative effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000003556 assay Methods 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
210000000481 breast Anatomy 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010908 decantation Methods 0.000 description 2
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
SRFDFLPBCXPCOJ-UHFFFAOYSA-N ethyl 2,7-dichloro-4-(chloromethyl)-6-methylquinoline-3-carboxylate Chemical compound C1=C(Cl)C(C)=CC2=C(CCl)C(C(=O)OCC)=C(Cl)N=C21 SRFDFLPBCXPCOJ-UHFFFAOYSA-N 0.000 description 2
INWICFYGQUCDBN-UHFFFAOYSA-N ethyl 7-chloro-4-(chloromethyl)-6-methyl-2-oxo-1h-quinoline-3-carboxylate Chemical compound CC1=C(Cl)C=C2NC(=O)C(C(=O)OCC)=C(CCl)C2=C1 INWICFYGQUCDBN-UHFFFAOYSA-N 0.000 description 2
239000012894 fetal calf serum Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000002502 liposome Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
-1 pamoate Chemical compound 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000002798 spectrophotometry method Methods 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SVGNVSSAOZJYGO-UHFFFAOYSA-N 1-(2-amino-4-chloro-5-methylphenyl)-2-chloroethanone Chemical compound CC1=CC(C(=O)CCl)=C(N)C=C1Cl SVGNVSSAOZJYGO-UHFFFAOYSA-N 0.000 description 1
RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
CFBVWCHTNQHZLT-UHFFFAOYSA-N 4-methoxy-5-[3-(2-methoxy-4-nitro-5-sulfophenyl)-5-(phenylcarbamoyl)tetrazol-3-ium-2-yl]-2-nitrobenzenesulfonate Chemical compound COC1=CC([N+]([O-])=O)=C(S([O-])(=O)=O)C=C1N1[N+](C=2C(=CC(=C(C=2)S(O)(=O)=O)[N+]([O-])=O)OC)=NC(C(=O)NC=2C=CC=CC=2)=N1 CFBVWCHTNQHZLT-UHFFFAOYSA-N 0.000 description 1
RXGJTUSBYWCRBK-UHFFFAOYSA-M 5-methylphenazinium methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=NC2=C1 RXGJTUSBYWCRBK-UHFFFAOYSA-M 0.000 description 1
ZMLJXSCAYVZFFT-UHFFFAOYSA-N 8-[[2,7-dichloro-6-methyl-4-[(4-methylpiperidin-1-yl)methyl]quinolin-3-yl]methyl]-5-ethyl-5-hydroxy-1,4-dihydrooxepino[3,4-c]pyridine-3,9-dione Chemical compound CCC1(O)CC(=O)OCC(C2=O)=C1C=CN2CC1=C(Cl)N=C2C=C(Cl)C(C)=CC2=C1CN1CCC(C)CC1 ZMLJXSCAYVZFFT-UHFFFAOYSA-N 0.000 description 1
208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
208000036832 Adenocarcinoma of ovary Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000759905 Camptotheca acuminata Species 0.000 description 1
208000017897 Carcinoma of esophagus Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
102000003915 DNA Topoisomerases Human genes 0.000 description 1
108090000323 DNA Topoisomerases Proteins 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
208000000461 Esophageal Neoplasms Diseases 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000004554 Leishmaniasis Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
208000034578 Multiple myelomas Diseases 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
206010061328 Ovarian epithelial cancer Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010035226 Plasma cell myeloma Diseases 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000024770 Thyroid neoplasm Diseases 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
NBEXZBYYVRZPOS-UHFFFAOYSA-N [2,7-dichloro-6-methyl-4-[(4-methylpiperidin-1-yl)methyl]quinolin-3-yl]methanol Chemical compound C1CC(C)CCN1CC1=C(CO)C(Cl)=NC2=CC(Cl)=C(C)C=C12 NBEXZBYYVRZPOS-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000002141 anti-parasite Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
125000005604 azodicarboxylate group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
201000010897 colon adenocarcinoma Diseases 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
GDTRAYDPXKZJGD-UHFFFAOYSA-N dichlorophosphoryl hypochlorite Chemical compound ClOP(Cl)(Cl)=O GDTRAYDPXKZJGD-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000007877 drug screening Methods 0.000 description 1
210000004696 endometrium Anatomy 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
150000003278 haem Chemical class 0.000 description 1
QDUXDCXILAPLAG-UHFFFAOYSA-N hydron;1-methylpiperidine;chloride Chemical compound Cl.CN1CCCCC1 QDUXDCXILAPLAG-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
UWVXWJCYPPLTLR-UHFFFAOYSA-N indolizino[1,2-b]quinoline Chemical group C1=CC=CN2C=C(C=C3C(C=CC=C3)=N3)C3=C21 UWVXWJCYPPLTLR-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000001802 infusion Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000000867 larynx Anatomy 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
201000005249 lung adenocarcinoma Diseases 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000004792 malaria Diseases 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
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000000693 micelle Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
201000006588 ovary adenocarcinoma Diseases 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
210000003800 pharynx Anatomy 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
239000013641 positive control Substances 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
239000001472 potassium tartrate Substances 0.000 description 1
229940111695 potassium tartrate Drugs 0.000 description 1
235000011005 potassium tartrates Nutrition 0.000 description 1
XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
210000005267 prostate cell Anatomy 0.000 description 1
238000002731 protein assay Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000011160 research Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 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
229940095064 tartrate Drugs 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
201000002510 thyroid cancer Diseases 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)
Compounds Of Unknown Constitution (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO20000995A 1997-08-29 2000-02-28 Optisk rene camptotecin analoger, optisk rent mellomprodukt, fremgangsmate for fremstilling av disse, anvendelse og farmasoytisk preparat NO324882B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9710785A FR2768431B1 (fr)	1997-08-29	1997-08-29	Nouveaux analogues optiquement purs de la camptothecine, nouvel intermediaire de synthese optiquement pur et son procede de preparation
PCT/FR1998/001768 WO1999011646A1 (fr)	1997-08-29	1998-08-07	Analogues optiquement purs de la camptothecine, intermediaire de synthese optiquement pur et son procede de preparation

Publications (3)

Publication Number	Publication Date
NO20000995D0 NO20000995D0 (no)	2000-02-28
NO20000995L NO20000995L (no)	2000-02-28
NO324882B1 true NO324882B1 (no)	2007-12-27

Family

ID=9510590

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20000995A NO324882B1 (no)	1997-08-29	2000-02-28	Optisk rene camptotecin analoger, optisk rent mellomprodukt, fremgangsmate for fremstilling av disse, anvendelse og farmasoytisk preparat

Country Status (25)

Country	Link
EP (2)	EP1007527B1 (de)
JP (1)	JP2001514261A (de)
KR (1)	KR100570254B1 (de)
CN (3)	CN1104434C (de)
AR (1)	AR016856A1 (de)
AT (1)	ATE253069T1 (de)
AU (1)	AU760863B2 (de)
BR (1)	BR9811405A (de)
CA (1)	CA2301739C (de)
CZ (1)	CZ297896B6 (de)
DE (1)	DE69819340T2 (de)
DK (1)	DK1007527T3 (de)
ES (1)	ES2209196T3 (de)
FR (1)	FR2768431B1 (de)
HR (1)	HRP20000110A2 (de)
HU (1)	HUP0003429A3 (de)
IL (2)	IL134437A0 (de)
NO (1)	NO324882B1 (de)
NZ (1)	NZ502862A (de)
PL (1)	PL195289B1 (de)
PT (1)	PT1007527E (de)
RU (1)	RU2233283C2 (de)
TW (1)	TW419479B (de)
WO (1)	WO1999011646A1 (de)
ZA (1)	ZA987445B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2790261B1 (fr)	1999-02-26	2004-09-10	Sod Conseils Rech Applic	Nouveaux analogues optiquement purs de la camptothecine et leurs procedes de preparation
US6207832B1 (en)	1999-04-09	2001-03-27	University Of Pittsburgh	Camptothecin analogs and methods of preparation thereof
US6372906B1 (en)	2001-04-12	2002-04-16	University Of Pittsburgh	Synthesis of silyl camptothecins and silyl homocamptothecins
US6723853B2 (en)	2001-08-27	2004-04-20	University Of Pittsburgh	Intermediates and methods of preparation of intermediates in the enantiomeric synthesis of (20R)homocamptothecins and the enantiomeric synthesis of (20R)homocamptothecins
CN100408582C (zh) *	2004-02-12	2008-08-06	中国人民解放军第二军医大学	高喜树碱类化合物及其制备方法和用途
JP2008513437A (ja) *	2004-09-21	2008-05-01	ソシエテドコンセイユドルシェルシェエダアップリカーションシャンティフィック（エス．セー．エール．アー．エス．）	有用な中間体の新規製造方法
CN100465175C (zh) *	2005-11-29	2009-03-04	中国人民解放军第二军医大学	7-位取代高喜树碱类化合物及作为药物的用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3008226B2 (ja) *	1991-01-16	2000-02-14	第一製薬株式会社	六環性化合物
US5459269A (en) *	1992-06-18	1995-10-17	North Carolina State University	14-halo-camptothecins
FR2757514B1 (fr) *	1996-12-20	1999-02-12	Sod Conseils Rech Applic	Nouveaux analogues de la camptothecine, des procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant
DE69635560T2 (de) *	1995-06-21	2006-08-17	Société de Conseils de Recherches et D'Applications Scientifiques (S.C.R.A.S.)	Camptothecinanaloge, Verfahren zur ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammensetzungen

1997
- 1997-08-29 FR FR9710785A patent/FR2768431B1/fr not_active Expired - Fee Related
1998
- 1998-08-07 AU AU89896/98A patent/AU760863B2/en not_active Ceased
- 1998-08-07 EP EP98941567A patent/EP1007527B1/de not_active Expired - Lifetime
- 1998-08-07 DE DE69819340T patent/DE69819340T2/de not_active Expired - Lifetime
- 1998-08-07 KR KR1020007002034A patent/KR100570254B1/ko not_active Expired - Fee Related
- 1998-08-07 WO PCT/FR1998/001768 patent/WO1999011646A1/fr not_active Ceased
- 1998-08-07 RU RU2000107822/04A patent/RU2233283C2/ru not_active IP Right Cessation
- 1998-08-07 EP EP03077049A patent/EP1378512A1/de not_active Withdrawn
- 1998-08-07 ES ES98941567T patent/ES2209196T3/es not_active Expired - Lifetime
- 1998-08-07 CZ CZ20000711A patent/CZ297896B6/cs not_active IP Right Cessation
- 1998-08-07 HU HU0003429A patent/HUP0003429A3/hu unknown
- 1998-08-07 AT AT98941567T patent/ATE253069T1/de active
- 1998-08-07 CA CA002301739A patent/CA2301739C/fr not_active Expired - Fee Related
- 1998-08-07 JP JP2000508685A patent/JP2001514261A/ja active Pending
- 1998-08-07 BR BR9811405-0A patent/BR9811405A/pt not_active Application Discontinuation
- 1998-08-07 DK DK98941567T patent/DK1007527T3/da active
- 1998-08-07 NZ NZ502862A patent/NZ502862A/xx unknown
- 1998-08-07 PT PT98941567T patent/PT1007527E/pt unknown
- 1998-08-07 CN CN98808720A patent/CN1104434C/zh not_active Expired - Lifetime
- 1998-08-07 CN CNB031021662A patent/CN1195758C/zh not_active Expired - Fee Related
- 1998-08-07 HR HR20000110A patent/HRP20000110A2/hr not_active Application Discontinuation
- 1998-08-07 PL PL98338835A patent/PL195289B1/pl not_active IP Right Cessation
- 1998-08-07 IL IL13443798A patent/IL134437A0/xx active IP Right Grant
- 1998-08-18 ZA ZA987445A patent/ZA987445B/xx unknown
- 1998-08-19 TW TW087113646A patent/TW419479B/zh not_active IP Right Cessation
- 1998-08-21 AR ARP980104157A patent/AR016856A1/es active IP Right Grant
2000
- 2000-02-08 IL IL134437A patent/IL134437A/en not_active IP Right Cessation
- 2000-02-28 NO NO20000995A patent/NO324882B1/no not_active IP Right Cessation
2003
- 2003-02-08 CN CN03102165A patent/CN1440972A/zh active Pending

Also Published As

Publication number	Publication date
KR100570254B1 (ko)	2006-04-12
AU760863B2 (en)	2003-05-22
ES2209196T3 (es)	2004-06-16
AU8989698A (en)	1999-03-22
DE69819340T2 (de)	2004-08-19
HRP20000110A2 (en)	2001-02-28
IL134437A0 (en)	2001-04-30
BR9811405A (pt)	2000-08-29
CZ297896B6 (cs)	2007-04-25
DE69819340D1 (de)	2003-12-04
NO20000995D0 (no)	2000-02-28
IL134437A (en)	2006-08-01
HUP0003429A3 (en)	2002-11-28
AR016856A1 (es)	2001-08-01
HK1031732A1 (en)	2001-06-22
EP1007527B1 (de)	2003-10-29
CN1440973A (zh)	2003-09-10
CZ2000711A3 (cs)	2000-08-16
TW419479B (en)	2001-01-21
ATE253069T1 (de)	2003-11-15
NZ502862A (en)	2002-10-25
CN1195758C (zh)	2005-04-06
EP1378512A1 (de)	2004-01-07
HUP0003429A1 (hu)	2001-07-30
RU2233283C2 (ru)	2004-07-27
FR2768431A1 (fr)	1999-03-19
PL195289B1 (pl)	2007-08-31
DK1007527T3 (da)	2004-03-08
WO1999011646A1 (fr)	1999-03-11
CN1268948A (zh)	2000-10-04
CA2301739A1 (fr)	1999-03-11
PT1007527E (pt)	2004-03-31
PL338835A1 (en)	2000-11-20
JP2001514261A (ja)	2001-09-11
CA2301739C (fr)	2009-11-17
EP1007527A1 (de)	2000-06-14
NO20000995L (no)	2000-02-28
FR2768431B1 (fr)	2000-03-24
CN1440972A (zh)	2003-09-10
KR20010023394A (ko)	2001-03-26
CN1104434C (zh)	2003-04-02
HK1058665A1 (en)	2004-05-28
ZA987445B (en)	1999-02-17

Legal Events

Date	Code	Title	Description
2012-03-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP0835258B1 (de)	2002-09-25	Camptothecinanaloge, verfahren zur ihrer herstellung, ihre verwendungals arzneimittel und diese enthaltende pharmazeutische zusammenfassungen
AU6192099A (en)	2000-04-10	Tetrahydropyridoethers
DE69726007T2 (de)	2004-06-03	Prodrogs und analoga von camptothecin und deren verwendung als arzneimittel
CA2275351C (fr)	2008-10-14	Nouveaux analogues de la camptothecine, leur application comme medicaments et les compositions pharmaceutiques les contenant
RU2233283C2 (ru)	2004-07-27	Оптически чистые аналоги камптотецина, оптически чистый промежуточный продукт синтеза и способ его получения
US6339091B1 (en)	2002-01-15	Comptothecin analogues, preparation methods therefor, use thereof as drugs, and pharmaceutical compositions containing said analogues
RU2190613C2 (ru)	2002-10-10	Аналоги камптотецина, способы их получения и фармацевтическая композиция на их основе
MXPA00001944A (en)	2001-12-04	Optically pure camptothecin analogues, optically pure synthesis intermediate and method for preparing same
US6797715B1 (en)	2004-09-28	Analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
HK1058666A (en)	2004-05-28	Optically pure camptothecin analogues, optically pure synthesis intermediate and method for preparing same
HK1031732B (en)	2004-02-06	Optically pure camptothecin analogues, optically pure synthesis intermediate and method for preparing same
CN116969939A (zh)	2023-10-31	溶酶体靶向的Eudistomin Y类化合物及其制备方法和应用
HK1058665B (zh)	2005-09-02	喜树碱的光学纯类似物