CA1097343A - Intermediaries de quinonoides polycycliques antibiotiques - Google Patents

Intermediaries de quinonoides polycycliques antibiotiques

Info

Publication number: CA1097343A
Authority: CA; Canada
Prior art keywords: acid; compound; suitably; reaction; hydrogen
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

CA265,539A

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

1976-11-12

Publication date

1981-03-10

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

1976-11-12 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 CA1097343A publication Critical patent/CA1097343A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 4
239000003242 anti bacterial agent Substances 0.000 title abstract description 3
229940088710 antibiotic agent Drugs 0.000 title abstract description 3
125000003367 polycyclic group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 47
238000000034 method Methods 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
238000005698 Diels-Alder reaction Methods 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
239000000126 substance Substances 0.000 claims 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000001475 halogen functional group Chemical group 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 2
150000004053 quinones Chemical class 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
230000002194 synthesizing effect Effects 0.000 abstract description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
230000000118 anti-neoplastic effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
239000002253 acid Substances 0.000 description 32
239000002904 solvent Substances 0.000 description 31
239000000203 mixture Substances 0.000 description 29
230000000875 corresponding effect Effects 0.000 description 23
229960001701 chloroform Drugs 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
229940022663 acetate Drugs 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 17
125000003118 aryl group Chemical group 0.000 description 15
239000003960 organic solvent Substances 0.000 description 15
-1 polycyclic quinones Chemical class 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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000007787 solid Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 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
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 9
125000001743 benzylic group Chemical group 0.000 description 9
239000000284 extract Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000002534 ethynyl group Chemical group [H]C#C* 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
239000000047 product Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000007800 oxidant agent Substances 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
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
239000007818 Grignard reagent Substances 0.000 description 6
125000001033 ether group Chemical group 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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
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 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
238000001914 filtration Methods 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
239000000463 material Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
239000002026 chloroform extract Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
BJLPSIPGXQUFGQ-UHFFFAOYSA-N 2-(2,5-dimethoxybenzoyl)benzoic acid Chemical compound COC1=CC=C(OC)C(C(=O)C=2C(=CC=CC=2)C(O)=O)=C1 BJLPSIPGXQUFGQ-UHFFFAOYSA-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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
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
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
239000011261 inert gas Substances 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
150000007524 organic acids Chemical class 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
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 2
150000005208 1,4-dihydroxybenzenes Chemical class 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
MORCGAGNSSORNZ-UHFFFAOYSA-N 5,12-dihydroxy-3,4-dihydro-1h-tetracene-2,6,11-trione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CC(=O)CCC1=C2O MORCGAGNSSORNZ-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
MGHGIFGQJWUVCO-UHFFFAOYSA-N 6,8,11-trihydroxy-1,4-dimethoxy-7,10-dihydrotetracene-5,12-dione Chemical compound COC1=CC=C(C=2C(C3=C(C=4CC=C(CC4C(=C3C(C12)=O)O)O)O)=O)OC MGHGIFGQJWUVCO-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
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-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
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 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
238000007872 degassing Methods 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
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 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
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-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
238000002360 preparation method Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
229910000108 silver(I,III) oxide Inorganic materials 0.000 description 2
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 2
239000002002 slurry Substances 0.000 description 2
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
229940070710 valerate Drugs 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
238000010792 warming Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
MWTPEJWHUMJPPU-UHFFFAOYSA-N 1,2,3-trihydroxytetracene-5,12-dione Chemical compound C1=CC=C2C=C(C(=O)C3=C(C=C(C(=C3O)O)O)C3=O)C3=CC2=C1 MWTPEJWHUMJPPU-UHFFFAOYSA-N 0.000 description 1
DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WCXKKSLEUONKJB-UHFFFAOYSA-N 1,4-dihydroxy-5,8-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(OC)=CC=C2OC WCXKKSLEUONKJB-UHFFFAOYSA-N 0.000 description 1
PQJOFSMSWLHFQE-UHFFFAOYSA-N 1,4-dimethoxy-5,8-dimethylanthracene-9,10-dione Chemical compound O=C1C2=C(C)C=CC(C)=C2C(=O)C2=C1C(OC)=CC=C2OC PQJOFSMSWLHFQE-UHFFFAOYSA-N 0.000 description 1
ZRFDDEAGCRNVNI-UHFFFAOYSA-N 1,4-dimethoxy-6,7-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC(C)=C(C)C=C2C(=O)C2=C1C(OC)=CC=C2OC ZRFDDEAGCRNVNI-UHFFFAOYSA-N 0.000 description 1
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VNMCKLVHDJADEB-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)oxyacetyl chloride Chemical compound CC(C)C1CCC(C)CC1OCC(Cl)=O VNMCKLVHDJADEB-UHFFFAOYSA-N 0.000 description 1
QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 1
BLFCXYJTVFTNRX-UHFFFAOYSA-N 2-chloro-4-(furan-2-yl)pyrimidine Chemical compound ClC1=NC=CC(C=2OC=CC=2)=N1 BLFCXYJTVFTNRX-UHFFFAOYSA-N 0.000 description 1
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WEPCDISQBQXOBE-UHFFFAOYSA-N 4,7-dimethyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C(C)C2=C1C(=O)OC2=O WEPCDISQBQXOBE-UHFFFAOYSA-N 0.000 description 1
CMNFGMRKUMTLDW-UHFFFAOYSA-N 5,8-dimethoxyanthracene-1,4,9,10-tetrone Chemical compound COC1=CC=C(OC)C(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O CMNFGMRKUMTLDW-UHFFFAOYSA-N 0.000 description 1
SZKHVFQMYPOBPL-UHFFFAOYSA-N 5,8-dimethylanthracene-1,4,9,10-tetrone Chemical compound CC1=CC=C(C)C(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O SZKHVFQMYPOBPL-UHFFFAOYSA-N 0.000 description 1
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
NNQPXACEWVDHMS-UHFFFAOYSA-N 6,8,11-trihydroxy-7,10-dihydrotetracene-5,12-dione Chemical compound OC1=C2C(C=3C=CC=CC3C(C2=C(C=2CC(=CCC12)O)O)=O)=O NNQPXACEWVDHMS-UHFFFAOYSA-N 0.000 description 1
OMNNKPLIHHLIJE-UHFFFAOYSA-N 9-acetyl-6,9,11-trihydroxy-1,4-dimethoxy-8,10-dihydro-7H-tetracene-5,12-dione Chemical compound C(C)(=O)C1(CCC=2C(=C3C(C=4C(=CC=C(C=4C(C3=C(C=2C1)O)=O)OC)OC)=O)O)O OMNNKPLIHHLIJE-UHFFFAOYSA-N 0.000 description 1
OTZLYCODBUGHTI-UHFFFAOYSA-N 9-ethynyl-6,9,11-trihydroxy-1,4-dimethoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1C(O)(C#C)CCC2=C1C(O)=C1C(=O)C(C(OC)=CC=C3OC)=C3C(=O)C1=C2O OTZLYCODBUGHTI-UHFFFAOYSA-N 0.000 description 1
YHBWDDDQUUPGJJ-UHFFFAOYSA-N 9-ethynyl-6,9,11-trihydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CC(O)(C#C)CCC1=C2O YHBWDDDQUUPGJJ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
241000575946 Ione Species 0.000 description 1
LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
GUNGPIRGWSBULW-UHFFFAOYSA-N buta-1,3-dien-2-yl benzoate Chemical compound C=CC(=C)OC(=O)C1=CC=CC=C1 GUNGPIRGWSBULW-UHFFFAOYSA-N 0.000 description 1
NMQQBXHZBNUXGJ-UHFFFAOYSA-N buta-1,3-dienyl acetate Chemical compound CC(=O)OC=CC=C NMQQBXHZBNUXGJ-UHFFFAOYSA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
229940076286 cupric acetate Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
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
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000005858 glycosidation reaction Methods 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
229940101209 mercuric oxide Drugs 0.000 description 1
229960001156 mitoxantrone Drugs 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical class CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 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
239000002798 polar solvent Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
125000004151 quinonyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
238000003797 solvolysis reaction Methods 0.000 description 1
238000000527 sonication Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA265,539A 1976-04-05 1976-11-12 Intermediaries de quinonoides polycycliques antibiotiques Expired CA1097343A (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 (2)

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

Publications (1)

Publication Number	Publication Date
CA1097343A true CA1097343A (fr)	1981-03-10

Family

ID=24702969

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA265,539A Expired CA1097343A (fr)	1976-04-05	1976-11-12	Intermediaries de quinonoides polycycliques antibiotiques

Country Status (9)

Country	Link
JP (2)	JPS5910648B2 (fr)
AU (1)	AU510598B2 (fr)
CA (1)	CA1097343A (fr)
CH (2)	CH637620A5 (fr)
ES (1)	ES453426A1 (fr)
IL (1)	IL50903A0 (fr)
NL (1)	NL7612742A (fr)
SE (1)	SE7612802L (fr)
ZA (1)	ZA766872B (fr)

1976
- 1976-11-11 CH CH1418776A patent/CH637620A5/de not_active IP Right Cessation
- 1976-11-12 CA CA265,539A patent/CA1097343A/fr not_active Expired
- 1976-11-12 IL IL50903A patent/IL50903A0/xx unknown
- 1976-11-16 JP JP51136957A patent/JPS5910648B2/ja not_active Expired
- 1976-11-16 SE SE7612802A patent/SE7612802L/xx unknown
- 1976-11-17 ES ES453426A patent/ES453426A1/es not_active Expired
- 1976-11-17 NL NL7612742A patent/NL7612742A/xx not_active Application Discontinuation
- 1976-11-17 ZA ZA766872A patent/ZA766872B/xx unknown
- 1976-11-18 AU AU19773/76A patent/AU510598B2/en not_active Expired
1979
- 1979-01-04 CH CH3379A patent/CH637101A5/de not_active IP Right Cessation
1981
- 1981-04-16 JP JP5640881A patent/JPS574937A/ja active Pending

Also Published As

Publication number	Publication date
CH637101A5 (en)	1983-07-15
AU1977376A (en)	1978-05-25
JPS5910648B2 (ja)	1984-03-10
ES453426A1 (es)	1978-02-16
ZA766872B (en)	1977-11-30
CH637620A5 (en)	1983-08-15
NL7612742A (nl)	1977-10-07
AU510598B2 (en)	1980-07-03
SE7612802L (sv)	1977-10-06
JPS52122354A (en)	1977-10-14
JPS574937A (en)	1982-01-11
IL50903A0 (en)	1977-01-31

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Date	Code	Title	Description
1998-03-10	MKEX	Expiry

Publication	Publication Date	Title
McKillop et al.	1970	Thallium in organic synthesis—XVI: Preparation of p-quinones by oxidation of phenols and hydroquinones with thallium (III) trifluoroacetate
Tashiro et al.	1982	Metacyclophanes and related compounds. 7. Preparation and reduction of [2.2] metacyclophanequinone
US4147706A (en)	1979-04-03	Intermediates for polycyclic quinonoid antibiotics
Bloomer et al.	1993	Preparation of functionalized juglone acetates and juglones via 1, 4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin
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
US4154745A (en)	1979-05-15	Isobenzofuran route to anthracycloquinones
CA1097343A (fr)	1981-03-10	Intermediaries de quinonoides polycycliques antibiotiques
Ruiz et al.	1981	Studies on quinones. VII. Synthesis of some benzo [b] thiophene‐4, 7‐diones
CA1097344A (fr)	1981-03-10	Intermediaries pour la production de quinonoides polycycliques antibiotiques
Kurtán et al.	2000	Synthesis and circular dichroism of steroids with 2, 3-dihydro-1-benzofuran and 4H-benzopyran chromophores; revision of the absolute configuration of some norneolignans from Krameria cystisoides
Pelter et al.	1998	A facile synthesis of 2-substituted isoflavones for immunoassay: Assembly of the isoflavonoid skeleton by means of a novel cyclisation reaction
Grove et al.	1952	760. Griseofulvin. Part II. Oxidative degradation
McKillop et al.	1977	Oxidation of phenols and hydroquinones by mercury (II) trifluoroacetate and mercury (II) oxide
CA1097345A (fr)	1981-03-10	Intermediaires pour la production de quinonoides polycycliques antibiotiques
Carpenter et al.	1979	Synthesis of structural analogues of 6, 7, 8, 9-tetrahydro-3-hydroxy-2-methoxybenzocyclohepten-5-one
US4164503A (en)	1979-08-14	Quinonoid intermediates from chloroprene
Pelter et al.	1979	The phenolic oxidation of a β-methylchalcone
Takahashi et al.	1959	Biochemical Studies on “Bakanae” Fungus. Part 51–53: Chemical Structure of Gibberellins. Part XVII. Chemical Structure of Gibberellins. Part XVIII. Chemical Structure of Gibberellins. Part XIX.
Cameron et al.	1978	Nucleophilic alkenes. VI. Addition of 1, 1-dimethoxyethene to 1, 2-naphthoquinones and 9, 10-phenanthraquinones
CN116120759A (zh)	2023-05-16	一种合成蒽类荧光染料的方法
Ooya et al.	1978	Syntheses and reactions of 10-(2, 2'-biphenylylene)-9-phenanthrone derivatives and some consideration of ethyl isomers in their analogous series.
Sasaki et al.	1968	Further Studies on Acetoxylation of Isodihydro-O-acetylisophotosantonic Lactone
Yates et al.	1970	Cyclooctatetraenoquinones. II. The synthesis and transformations of compounds related to dibenzo [a, e] cyclooctene-5, 6, 11 (12 H)-trione
Pouzar et al.	1987	Preparation of 21-methoxycarbonyl-21-methylene-5-pregnen-3β-ol derivatives