CA1140923A - Agents antitumeurs - Google Patents

Agents antitumeurs

Info

Publication number: CA1140923A
Authority: CA; Canada
Prior art keywords: leuco; bis; carbon atoms; dihydroxyanthraquinone; product
Prior art date: 1977-08-15
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

CA000309197A

Other languages

English (en)

Inventor

Keith C. Murdock

Frederick E. Durr

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

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.)

1977-08-15

Filing date

1978-08-11

Publication date

1983-02-08

1978-08-11 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1983-02-08 Application granted granted Critical

1983-02-08 Publication of CA1140923A publication Critical patent/CA1140923A/fr

Status Expired legal-status Critical Current

Links

239000002246 antineoplastic agent Substances 0.000 title 1
-1 1,4-bis-(substituted-amino)-5,8-dihydroxyanthraquinones Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 59
229960001156 mitoxantrone Drugs 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 46
229910052757 nitrogen Inorganic materials 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 31
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 16
230000008569 process Effects 0.000 claims description 16
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
230000003647 oxidation Effects 0.000 claims description 12
238000007254 oxidation reaction Methods 0.000 claims description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
QJQPINQAQJTYMH-UHFFFAOYSA-N 5,8,9,10-tetrahydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound O=C1CCC(=O)C2=C1C(O)=C1C(O)=CC=C(O)C1=C2O QJQPINQAQJTYMH-UHFFFAOYSA-N 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims 1
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000005406 washing Methods 0.000 description 6
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229910000041 hydrogen chloride Inorganic materials 0.000 description 5
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239000003921 oil Substances 0.000 description 5
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XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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208000028018 Lymphocytic leukaemia Diseases 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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 4
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QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 4
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GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 3
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125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
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229910052727 yttrium Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000309197A 1977-08-15 1978-08-11 Agents antitumeurs Expired CA1140923A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US82487277A	1977-08-15	1977-08-15
US824,872		1977-08-15
US87304078A	1978-01-30	1978-01-30
US873,040		1978-01-30

Publications (1)

Publication Number	Publication Date
CA1140923A true CA1140923A (fr)	1983-02-08

Family

ID=27124852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000309197A Expired CA1140923A (fr)	1977-08-15	1978-08-11	Agents antitumeurs

Country Status (2)

Country	Link
CA (1)	CA1140923A (fr)
PH (1)	PH19232A (fr)

1978
- 1978-08-11 PH PH21484A patent/PH19232A/en unknown
- 1978-08-11 CA CA000309197A patent/CA1140923A/fr not_active Expired

Also Published As

Publication number	Publication date
PH19232A (en)	1986-02-12

Legal Events

Date	Code	Title	Description
2000-02-08	MKEX	Expiry

Publication	Publication Date	Title
US4197249A (en)	1980-04-08	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
JP2604783B2 (ja)	1997-04-30	ビスーナフタルイミド及びこれを含有する腫瘍抑制及び抗白血病作用を有する医薬
US4296030A (en)	1981-10-20	Metal chelates of 1,4-bis(substituted-amino-5,8-dihydroxy-anthraquinones
EP0929516A1 (fr)	1999-07-21	Derives de benzamidine et leur utilisation comme medicaments ayant un effet antagoniste vis-a-vis de ltb4
IE47253B1 (en)	1984-02-08	Anthraquinone derivatives
KR840001965B1 (ko)	1984-10-26	안트라센-9,10-비스-카르보닐-히드라존 유도체 제조방법
US4526989A (en)	1985-07-02	1,4-Bis (substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
US4278689A (en)	1981-07-14	1,4-Bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
CA1140923A (fr)	1983-02-08	Agents antitumeurs
US5488110A (en)	1996-01-30	Highly water soluble bis-naphthalimides useful as anticancer agents
US4820738A (en)	1989-04-11	1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
US4456552A (en)	1984-06-26	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4540519A (en)	1985-09-10	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4389399A (en)	1983-06-21	Thiocarbamoyl heterocycle-anthraquinone derivatives
CA1148541A (fr)	1983-06-21	1-(aminoalkylamino)-5,8-dihydroxy anthraquinones substituees en 4
US4430501A (en)	1984-02-07	1,4-Bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
CA1152506A (fr)	1983-08-23	5,8-dihydroxy-1,4-bis(guanidinyl-amino) anthraquinones
US4428882A (en)	1984-01-31	1-(Aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones
US4614618A (en)	1986-09-30	1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof
US4410524A (en)	1983-10-18	Novel 1,4-bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
AU609605B2 (en)	1991-05-02	Intermediates for the preparation of novel substituted benzoselenino {4,3,2-cd} indazoles
US4888137A (en)	1989-12-19	Novel 1,4-bis(substituted-amino(-5,8-dihydroxyanthraquinones and leuco bases thereof
US4540583A (en)	1985-09-10	Method of treating tumors in warm-blooded animals
CA1178203A (fr)	1984-11-20	Methode de traitement des tumeurs chez les animaux a sang chaud
EP0087951B1 (fr)	1989-09-13	Dérivés de la phenanthroline