CS251091A3 - Tricyclic heterocyclic derivatives, process of their preparation and pharmaceuticals containing them - Google Patents

Tricyclic heterocyclic derivatives, process of their preparation and pharmaceuticals containing them Download PDF

Info

Publication number: CS251091A3
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; hydroxy; carbon atoms; compound
Prior art date: 1990-08-16

Application number

CS912510A

Other languages

Czech (cs)

English (en)

Inventor

Roger John Butlin

Dickson Glarvey

Original Assignee

Ici Plc

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.)

1990-08-16

Filing date

1991-08-14

Publication date

1992-03-18

1991-08-14 Application filed by Ici Plc filed Critical Ici Plc

1992-03-18 Publication of CS251091A3 publication Critical patent/CS251091A3/cs

Links

125000000623 heterocyclic group Chemical group 0.000 title claims description 52
238000002360 preparation method Methods 0.000 title claims description 20
239000003814 drug Substances 0.000 title claims description 6
238000000034 method Methods 0.000 title description 44
230000008569 process Effects 0.000 title description 7
-1 4-oxo- 1,4-dihydropyrid-1-yl ring Chemical group 0.000 claims description 232
150000001875 compounds Chemical class 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
125000001424 substituent group Chemical group 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
150000002148 esters Chemical class 0.000 claims description 26
238000001727 in vivo Methods 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 16
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 13
239000000460 chlorine Chemical group 0.000 claims description 12
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 10
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000004149 thio group Chemical group *S* 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
ZFZRBAHVXBFSIB-UHFFFAOYSA-N 3-chloro-2-fluoro-10-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]acridin-9-one Chemical compound COC1=C(O)C(OC)=CC(CN2C3=CC(Cl)=C(F)C=C3C(=O)C3=CC=CC=C32)=C1 ZFZRBAHVXBFSIB-UHFFFAOYSA-N 0.000 claims description 2
125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
230000001093 anti-cancer Effects 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
RALUVQUNBYOZAG-UHFFFAOYSA-N 10-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-piperazin-1-ylacridin-9-one Chemical compound COC1=C(O)C(OC)=CC(CN2C3=CC(=CC=C3C(=O)C3=CC=CC=C32)N2CCNCC2)=C1 RALUVQUNBYOZAG-UHFFFAOYSA-N 0.000 claims 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
RQMCIUOLWMNSNW-UHFFFAOYSA-N 3-[2-(dimethylamino)ethylsulfanyl]-10-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]acridin-9-one Chemical compound COC1=C(O)C(OC)=CC(CN2C3=CC(SCCN(C)C)=CC=C3C(=O)C3=CC=CC=C32)=C1 RQMCIUOLWMNSNW-UHFFFAOYSA-N 0.000 claims 1
LTWMIMRNMPUYLR-UHFFFAOYSA-N 3-hydroxy-10-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]acridin-9-one Chemical compound COC1=C(O)C(OC)=CC(CN2C3=CC(O)=CC=C3C(=O)C3=CC=CC=C32)=C1 LTWMIMRNMPUYLR-UHFFFAOYSA-N 0.000 claims 1
KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
MLACQEBQGUBHKX-UHFFFAOYSA-N n,n-dimethylpiperidin-1-amine Chemical compound CN(C)N1CCCCC1 MLACQEBQGUBHKX-UHFFFAOYSA-N 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
125000006168 tricyclic group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 109
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000000203 mixture Substances 0.000 description 88
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 58
239000000243 solution Substances 0.000 description 47
229910052943 magnesium sulfate Inorganic materials 0.000 description 29
235000019341 magnesium sulphate Nutrition 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000047 product Substances 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000012267 brine Substances 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
239000007858 starting material Substances 0.000 description 20
238000012360 testing method Methods 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
210000004027 cell Anatomy 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
238000004440 column chromatography Methods 0.000 description 16
239000003480 eluent Substances 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
206010028980 Neoplasm Diseases 0.000 description 13
238000011282 treatment Methods 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 10
125000002252 acyl group Chemical group 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000007787 solid Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
201000009030 Carcinoma Diseases 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
230000003217 anti-cancerogenic effect Effects 0.000 description 8
238000003556 assay Methods 0.000 description 8
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 8
229960005420 etoposide Drugs 0.000 description 8
239000000284 extract Substances 0.000 description 8
208000032839 leukemia Diseases 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
208000000587 small cell lung carcinoma Diseases 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
238000003756 stirring Methods 0.000 description 8
101710183280 Topoisomerase Proteins 0.000 description 7
102000007537 Type II DNA Topoisomerases Human genes 0.000 description 7
108010046308 Type II DNA Topoisomerases Proteins 0.000 description 7
201000011510 cancer Diseases 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
241000699666 Mus <mouse, genus> Species 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
108020004414 DNA Proteins 0.000 description 5
229910052784 alkaline earth metal Inorganic materials 0.000 description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000002246 antineoplastic agent Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000003993 interaction Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000000463 material Substances 0.000 description 5
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235000010446 mineral oil Nutrition 0.000 description 5
239000003921 oil Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000010992 reflux Methods 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
GIJGXNFNUUFEGH-UHFFFAOYSA-N Isopentyl mercaptan Chemical compound CC(C)CCS GIJGXNFNUUFEGH-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
125000005336 allyloxy group Chemical group 0.000 description 4
239000003005 anticarcinogenic agent Substances 0.000 description 4
125000003435 aroyl group Chemical group 0.000 description 4
125000005002 aryl methyl group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000012010 growth Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
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239000002184 metal Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
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RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 4
239000012265 solid product Substances 0.000 description 4
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 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
KQZQXDXQBZATTC-UHFFFAOYSA-N 3-fluoro-10h-acridin-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(F)C=C3NC2=C1 KQZQXDXQBZATTC-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
231100001074 DNA strand break Toxicity 0.000 description 3
241000282412 Homo Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
206010058467 Lung neoplasm malignant Diseases 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
206010041067 Small cell lung cancer Diseases 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
125000005103 alkyl silyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
238000004113 cell culture Methods 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
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238000003379 elimination reaction Methods 0.000 description 3
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QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
201000000498 stomach carcinoma Diseases 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 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
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000002381 testicular Effects 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000003734 thymidylate synthase inhibitor Substances 0.000 description 1
201000002510 thyroid cancer Diseases 0.000 description 1
208000013077 thyroid gland carcinoma Diseases 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000012549 training Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
230000035899 viability Effects 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- 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

Landscapes

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

CS912510A 1990-08-16 1991-08-14 Tricyclic heterocyclic derivatives, process of their preparation and pharmaceuticals containing them CS251091A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909018044A GB9018044D0 (en)	1990-08-16	1990-08-16	Tricyclic heterocyclic derivatives

Publications (1)

Publication Number	Publication Date
CS251091A3 true CS251091A3 (en)	1992-03-18

Family

ID=10680792

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS912510A CS251091A3 (en)	1990-08-16	1991-08-14	Tricyclic heterocyclic derivatives, process of their preparation and pharmaceuticals containing them

Country Status (14)

Country	Link
EP (1)	EP0471516A1 (ja)
JP (1)	JPH04257563A (ja)
KR (1)	KR920004352A (ja)
AU (1)	AU8142291A (ja)
CA (1)	CA2048298A1 (ja)
CS (1)	CS251091A3 (ja)
FI (1)	FI913893A7 (ja)
GB (2)	GB9018044D0 (ja)
HU (1)	HUT58293A (ja)
IE (1)	IE912616A1 (ja)
IL (1)	IL99075A0 (ja)
NO (1)	NO913187L (ja)
PT (1)	PT98680A (ja)
ZA (1)	ZA915937B (ja)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU7145396A (en) *	1995-10-04	1997-04-28	Eisai Co. Ltd.	Acridone compounds
US6063921A (en)	1997-11-20	2000-05-16	Pharm-Eco Laboratories, Inc.	Synthesis of 11-aryl-5,6-dihydro-11H-dibenz[b,e]azepines
AU2001288432A1 (en)	2000-09-01	2002-03-22	Icos Corporation	Materials and methods to potentiate cancer treatment
JP2006523681A (ja) *	2003-03-24	2006-10-19	ルイトポルド・ファーマシューティカルズ・インコーポレーテッド	Ｄｎａ−ｐｋ阻害剤としてのキサントン、チオキサントンおよびアクリジノン
PL2130817T3 (pl)	2008-06-05	2016-06-30	Agfa Graphics Nv	Polimeryzowalne fotoinicjatory typu ii oraz kompozycje utwardzalne
US11866412B1 (en)	2023-03-03	2024-01-09	King Faisal University	Acridin-9-one compounds as antibacterial agents

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1585099A (ja) *	1967-07-13	1970-01-09
DE2759468A1 (de) *	1977-08-29	1979-06-07	Sterling Drug Inc	Acridinonverbindungen und ihre herstellung

1990
- 1990-08-16 GB GB909018044A patent/GB9018044D0/en active Pending
1991
- 1991-07-24 IE IE261691A patent/IE912616A1/en unknown
- 1991-07-26 HU HU912511A patent/HUT58293A/hu unknown
- 1991-07-29 ZA ZA915937A patent/ZA915937B/xx unknown
- 1991-07-29 AU AU81422/91A patent/AU8142291A/en not_active Abandoned
- 1991-08-01 CA CA002048298A patent/CA2048298A1/en not_active Abandoned
- 1991-08-02 GB GB919116779A patent/GB9116779D0/en active Pending
- 1991-08-04 IL IL99075A patent/IL99075A0/xx unknown
- 1991-08-09 EP EP91307341A patent/EP0471516A1/en not_active Withdrawn
- 1991-08-14 KR KR1019910014211A patent/KR920004352A/ko not_active Withdrawn
- 1991-08-14 PT PT98680A patent/PT98680A/pt not_active Application Discontinuation
- 1991-08-14 CS CS912510A patent/CS251091A3/cs unknown
- 1991-08-15 NO NO91913187A patent/NO913187L/no unknown
- 1991-08-15 JP JP3205027A patent/JPH04257563A/ja active Pending
- 1991-08-16 FI FI913893A patent/FI913893A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
IE912616A1 (en)	1992-02-26
FI913893L (fi)	1992-02-17
CA2048298A1 (en)	1992-02-17
NO913187L (no)	1992-02-17
EP0471516A1 (en)	1992-02-19
ZA915937B (en)	1992-04-29
HUT58293A (en)	1992-02-28
AU8142291A (en)	1992-02-20
PT98680A (pt)	1992-08-31
IL99075A0 (en)	1992-07-15
HU912511D0 (en)	1992-01-28
KR920004352A (ko)	1992-03-27
JPH04257563A (ja)	1992-09-11
GB9018044D0 (en)	1990-10-03
FI913893A0 (fi)	1991-08-16
NO913187D0 (no)	1991-08-15
FI913893A7 (fi)	1992-02-17
GB9116779D0 (en)	1991-09-18

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