CA1097344A - Intermediaries pour la production de quinonoides polycycliques antibiotiques - Google Patents

Intermediaries pour la production de quinonoides polycycliques antibiotiques

Info

Publication number: CA1097344A
Authority: CA; Canada
Prior art keywords: acid; suitably; compound; reaction; dimethyl
Prior art date: 1976-04-05
Legal status (The legal status 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 status listed.): Expired

Application number

CA000300132A

Other languages

English (en)

Inventor

Andrew S. Kende

John E. Mills

Yuh-Geng Tsay

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Research Corp

Original Assignee

Research Corp

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.)

1976-04-05

Filing date

1978-03-31

Publication date

1981-03-10

1976-04-05 Priority claimed from US05/673,513 external-priority patent/US4021457A/en

1976-11-12 Priority claimed from CA265,539A external-priority patent/CA1097343A/fr

1978-03-31 Application filed by Research Corp filed Critical Research Corp

1978-03-31 Priority to CA000300132A priority Critical patent/CA1097344A/fr

1981-03-10 Application granted granted Critical

1981-03-10 Publication of CA1097344A publication Critical patent/CA1097344A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 3
239000003242 anti bacterial agent Substances 0.000 title description 2
229940088710 antibiotic agent Drugs 0.000 title description 2
125000003367 polycyclic group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 43
238000002360 preparation method Methods 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
MORCGAGNSSORNZ-UHFFFAOYSA-N 5,12-dihydroxy-3,4-dihydro-1h-tetracene-2,6,11-trione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CC(=O)CCC1=C2O MORCGAGNSSORNZ-UHFFFAOYSA-N 0.000 abstract description 2
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 36
239000000243 solution Substances 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 31
239000002904 solvent Substances 0.000 description 26
229960001701 chloroform Drugs 0.000 description 23
230000000875 corresponding effect Effects 0.000 description 23
229940022663 acetate Drugs 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
-1 polycyclic quinones Chemical class 0.000 description 16
125000003118 aryl group Chemical group 0.000 description 15
239000003960 organic solvent Substances 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
239000007787 solid Substances 0.000 description 11
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 description 10
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 10
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
125000001743 benzylic group Chemical group 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
239000011707 mineral Substances 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
239000002585 base Substances 0.000 description 7
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 6
YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 description 6
238000005698 Diels-Alder reaction Methods 0.000 description 6
239000007818 Grignard reagent Substances 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000463 material Substances 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000010828 elution Methods 0.000 description 5
125000001033 ether group Chemical group 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000003495 polar organic solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
125000000746 allylic group Chemical group 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZUFQFGSMHXKORU-YUNKPMOVSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-YUNKPMOVSA-N 0.000 description 3
ZUFQFGSMHXKORU-UHFFFAOYSA-N 9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(O)CC(C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
KNCZUXHSQJQWIB-UHFFFAOYSA-N anthracene-1,4,9,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(=O)C=CC2=O KNCZUXHSQJQWIB-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 3
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 3
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
HWHFKYJAAJPFQF-UHFFFAOYSA-N 1,4-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(OC)=CC=C2OC HWHFKYJAAJPFQF-UHFFFAOYSA-N 0.000 description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
KIJPZYXCIHZVGP-UHFFFAOYSA-N 2,3-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(C)=C2 KIJPZYXCIHZVGP-UHFFFAOYSA-N 0.000 description 2
BRHPCPPFSBACMJ-UHFFFAOYSA-N 6,7-dimethylanthracene-1,4,9,10-tetrone Chemical compound C1=C(C)C(C)=CC(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O BRHPCPPFSBACMJ-UHFFFAOYSA-N 0.000 description 2
HIWASLYFYGJESA-UHFFFAOYSA-N 6,9,11-trihydroxy-2,3-dimethyl-7,8-dihydrotetracene-5,12-dione Chemical compound C1CC(O)=CC2=C1C(O)=C1C(=O)C(C=C(C(=C3)C)C)=C3C(=O)C1=C2O HIWASLYFYGJESA-UHFFFAOYSA-N 0.000 description 2
MHDQQUDEAYEFHB-UHFFFAOYSA-N 9-acetyl-6,9,11-trihydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CCC(C(=O)C)(O)CC1=C2O MHDQQUDEAYEFHB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
DYBUYNXFWDRGMW-UHFFFAOYSA-N buta-1,3-dien-2-ol Chemical compound OC(=C)C=C DYBUYNXFWDRGMW-UHFFFAOYSA-N 0.000 description 2
PMOLKBNSJNLKGB-UHFFFAOYSA-N buta-1,3-dien-2-yl acetate Chemical compound CC(=O)OC(=C)C=C PMOLKBNSJNLKGB-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
229960000975 daunorubicin Drugs 0.000 description 2
238000005837 enolization reaction Methods 0.000 description 2
238000006345 epimerization reaction Methods 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
ANQVKHGDALCPFZ-UHFFFAOYSA-N ethyl 2-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]acetate Chemical compound C1=C2NC(CC(=O)OCC)=NC2=CC=C1N1CCN(C)CC1 ANQVKHGDALCPFZ-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
229940101209 mercuric oxide Drugs 0.000 description 2
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000003884 phenylalkyl group Chemical group 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
GUEIZVNYDFNHJU-UHFFFAOYSA-N quiniazarine Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
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229910000029 sodium carbonate Inorganic materials 0.000 description 2
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YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
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229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
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239000003365 glass fiber Substances 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
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229910001385 heavy metal Inorganic materials 0.000 description 1
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150000002500 ions Chemical class 0.000 description 1
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125000004151 quinonyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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230000000717 retained effect Effects 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
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239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000300132A 1976-04-05 1978-03-31 Intermediaries pour la production de quinonoides polycycliques antibiotiques Expired CA1097344A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000300132A CA1097344A (fr)	1976-04-05	1978-03-31	Intermediaries pour la production de quinonoides polycycliques antibiotiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/673,513 US4021457A (en)	1975-11-18	1976-04-05	Intermediates for polycyclic quinonoid antibiotics
US673,513		1976-04-05
CA265,539A CA1097343A (fr)	1976-04-05	1976-11-12	Intermediaries de quinonoides polycycliques antibiotiques
CA000300132A CA1097344A (fr)	1976-04-05	1978-03-31	Intermediaries pour la production de quinonoides polycycliques antibiotiques

Publications (1)

Publication Number	Publication Date
CA1097344A true CA1097344A (fr)	1981-03-10

Family

ID=27164764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000300132A Expired CA1097344A (fr)	1976-04-05	1978-03-31	Intermediaries pour la production de quinonoides polycycliques antibiotiques

Country Status (1)

Country	Link
CA (1)	CA1097344A (fr)

1978
- 1978-03-31 CA CA000300132A patent/CA1097344A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
Guindon et al.	1987	Regiocontrolled opening of cyclic ethers using dimethylboron bromide
Tashiro et al.	1982	Metacyclophanes and related compounds. 7. Preparation and reduction of [2.2] metacyclophanequinone
CA1097342A (fr)	1981-03-10	Intermediaires de quinonoides polycycliques antibiotiques
Kuehne et al.	1991	Total syntheses of tubotaiwine and 19, 20-dihydro-20-epi-akuammicine
US4021457A (en)	1977-05-03	Intermediates for polycyclic quinonoid antibiotics
Lehr et al.	1978	Synthesis of the non-K-region and K-region trans-dihydrodiols of benzo [e] pyrene
CA1097344A (fr)	1981-03-10	Intermediaries pour la production de quinonoides polycycliques antibiotiques
RU2022959C1 (ru)	1994-11-15	Способ получения замещенных 2,3,5,8-тетрагидрокси-1,4-нафтахинонов
CA1097343A (fr)	1981-03-10	Intermediaries de quinonoides polycycliques antibiotiques
Wendling et al.	1978	Synthesis and novel physical properties of a biphenoquinoquinocyclopropane
Singh et al.	1979	Nitrogen photochemistry. Cocaine and its model compounds
Kurosawa et al.	1979	Reactions of 2'-hydroxyisoflavone and 2'-hydroxy-2-methylisoflavones with metal salts.
Ueda et al.	1977	A new synthesis of 9-xanthenones by the reaction of 2-hydroxybenzophenones with metal salts.
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