WO1991019725A3 - Heterocyclic anthracyclione and anthracycline analogs - Google Patents

Heterocyclic anthracyclione and anthracycline analogs Download PDF

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Publication number
WO1991019725A3
WO1991019725A3 PCT/CA1991/000208 CA9100208W WO9119725A3 WO 1991019725 A3 WO1991019725 A3 WO 1991019725A3 CA 9100208 W CA9100208 W CA 9100208W WO 9119725 A3 WO9119725 A3 WO 9119725A3
Authority
WO
WIPO (PCT)
Prior art keywords
cancer
heterocyclic
anthracyclione
anthracycline analogs
anthracycline
Prior art date
Application number
PCT/CA1991/000208
Other languages
French (fr)
Other versions
WO1991019725A2 (en
Inventor
Giorgio Attardo
Yao Chang Xu
Jean-Francois Lavallee
Rabindra N Rej
Bernard Di Belleau
Original Assignee
Iaf Biochem Int
Belleau Pierrette & Hm
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.)
Filing date
Publication date
Application filed by Iaf Biochem Int, Belleau Pierrette & Hm filed Critical Iaf Biochem Int
Priority to AU80973/91A priority Critical patent/AU653348B2/en
Priority to JP3510688A priority patent/JPH06504034A/en
Publication of WO1991019725A2 publication Critical patent/WO1991019725A2/en
Publication of WO1991019725A3 publication Critical patent/WO1991019725A3/en
Priority to NO92924781A priority patent/NO924781L/en
Priority to FI925611A priority patent/FI925611A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/244—Anthraquinone radicals, e.g. sennosides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Forms Removed On Construction Sites Or Auxiliary Members Thereof (AREA)

Abstract

Heterocyclic anthracyclinone and anthracycline derivatives are described, which are useful in the treatment of cancer and tumors, such as breast cancer, leukemia, lung cancer, colon cancer, ovarian cancer, renal cancer, CNS cancer and melanoma. Pharmaceutical compositions and methods of preparing the compounds are also described.
PCT/CA1991/000208 1990-06-11 1991-06-10 Heterocyclic anthracyclione and anthracycline analogs WO1991019725A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU80973/91A AU653348B2 (en) 1990-06-11 1991-06-10 Heterocyclic anthracyclinone and anthracycline analogs
JP3510688A JPH06504034A (en) 1990-06-11 1991-06-10 Heterocyclic anthracyclions and anthracycline analogues
NO92924781A NO924781L (en) 1990-06-11 1992-12-10 Heterocyclic Anthracycline And Anthracycline Analogs
FI925611A FI925611A (en) 1990-06-11 1992-12-10 HETEROCYCLISKA ANTRACYKLIDON- OCH ANTRACYKLINANALOGER

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53610790A 1990-06-11 1990-06-11
US536,107 1990-06-11

Publications (2)

Publication Number Publication Date
WO1991019725A2 WO1991019725A2 (en) 1991-12-26
WO1991019725A3 true WO1991019725A3 (en) 1992-04-30

Family

ID=24137175

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1991/000208 WO1991019725A2 (en) 1990-06-11 1991-06-10 Heterocyclic anthracyclione and anthracycline analogs

Country Status (18)

Country Link
EP (1) EP0533744A1 (en)
JP (1) JPH06504034A (en)
CN (1) CN1058781A (en)
AP (1) AP340A (en)
AU (1) AU653348B2 (en)
CA (1) CA2085120A1 (en)
CS (1) CS178691A3 (en)
FI (1) FI925611A (en)
HU (1) HU9203720D0 (en)
IE (1) IE911965A1 (en)
IL (1) IL98460A0 (en)
MA (1) MA22178A1 (en)
NZ (1) NZ238490A (en)
PL (1) PL297164A1 (en)
PT (1) PT97931A (en)
WO (1) WO1991019725A2 (en)
YU (1) YU103391A (en)
ZA (1) ZA914452B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5606037A (en) * 1992-11-09 1997-02-25 Biochem Pharma Inc. Processes antineoplastic heteronaphthoquinones
AU5414094A (en) * 1992-11-09 1994-06-08 Biochem Pharma Inc. Antineoplastic heteronaphthoquinones
US5736523A (en) * 1992-11-09 1998-04-07 Biochem Pharma Inc. Antineoplastic heteronapthoquinones
AU6672794A (en) * 1993-11-05 1995-05-23 Biochem Pharma Inc. Antineoplastic heteronaphthoquinones
IT1271689B (en) * 1994-08-04 1997-06-04 Menarini Farma Ind 8-FLUORO-ANTRACICLINE, THEIR PREPARATION PROCESSES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
KR20210057053A (en) 2018-08-23 2021-05-20 씨젠 인크. Anti-TIGIT antibody
CN111087377B (en) * 2020-03-19 2020-06-26 广东省微生物研究所（广东省微生物分析检测中心） Benzo isochroman quinone compound and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2067552A (en) * 1980-01-16 1981-07-30 Erba Farmitalia Anthracycline derivatives
EP0251361A1 (en) * 1986-05-21 1988-01-07 Duphar International Research B.V New di- and tetrahydroisoquinoline derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52148088A (en) * 1976-06-01 1977-12-08 Richardson Merrell Inc 111aminoalkylmorphansridinee 111ols
JPS6030315B2 (en) * 1976-06-01 1985-07-16 三井東圧化学株式会社 Method for producing 4-halogenomethylisocoumarin derivative
JPS60142976A (en) * 1983-12-28 1985-07-29 Yoshinori Asakawa Isocoumarin derivative
JPH01238579A (en) * 1988-03-18 1989-09-22 Yamanouchi Pharmaceut Co Ltd Substance y-05460m-a and production thereof
JPH08112310A (en) * 1994-10-18 1996-05-07 New Oji Paper Co Ltd Disposable diaper

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2067552A (en) * 1980-01-16 1981-07-30 Erba Farmitalia Anthracycline derivatives
EP0251361A1 (en) * 1986-05-21 1988-01-07 Duphar International Research B.V New di- and tetrahydroisoquinoline derivatives

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
B.W. BYCROFT: "Dictionary of Antibiotics and Related Substances", 1988, Chapman & Hall (London, GB) see page 76, A-00427, Antibiotic DC44A *
Chemical Abstracts, vol. 104, no. 11, 17 March 1986 (Columbus, Ohio, US), see page 647, abstract no. 88435v, & JP,A,60142976 (OTSUKA PHARMACEUTICAL CO., LTD) 29 July 1985 *
Chemical Abstracts, vol. 108, no. 21, 23 May 1988 (Columbus, Ohio, US), A. KUBO et al.: "A facile synthesis of 1,2,3,4-terahydroisoquinolines through cyclization of O,N-acetals", see page 685, abstract no. 186527d, & SYNTHESIS 1987, (9), 824-7 *
Chemical Abstracts, vol. 112, no. 19, 7 May 1990 (Columbus, Ohio, US), see pages 592,593, abstract no. 177028x, & JP,A,01238579 (YAMANOUCHI PHARMACEUTICAL CO., LTD) 22 September 1989 *
Chemical Abstracts, vol. 94, no. 22, 1 June 1981 (Columbus, Ohio, US), see pages 380,381, abstract no. 180684y, & JP,A,8112310 (INSTITUTE OF PHYSICAL AND CHEMICAL RESEARCH HIGASHIKAZE, MUTSUYUKI et al.) 6 February 1981 *
Chemical Abstracts, vol. 94, no. 5, 2 February 1981, (Columbus, Ohio, US), M. GOLDSTEIN et al.: "The blockade of alpha2-adrenoceptors by the PNMT inhibitor SK&F 64139", see page 29, abstract no. 24828t, & EUR. J. PHARMACOL. 1980, 67(2-3),305-8 *
Chemical Abstracts, vol. 97, no. 5, 2 August 1982 (Columbus, Ohio, US), J.I. RETAMAL et al.: "Studies on quinones. IX. Synthesis of isochroman-5,8-diones", see page 561, abstract no. 38804f, & SYNTH. COMMUN. 1982, 12(4), 279-85 *
Heterocycles, vol. 26, no. 4, 1987, H. DUFAT-TRINH VAN: "Total synthesis of 7-hydroxy-"9-oxa"-anthracyclinone and glycoside derivatives", pages 879-882, see pages 880-881, compounds 11,4a,4b (cited in the application) *
J. Chem. Soc. Perkin Trans. I. 1984, R.G.F. GILES et al.: "An investigation into the formation of benzo- and naphtho-pyrans by cyclisation of ortho-alkenyl(hydroxyalkyl)benzenes using either cerium(IV)ammonium nitrate or potassium t-butoxide in dimethylformamide", pages 2389-2395, see page 2390, compounds 26,39,41-43 *
J. Med. Chem., vol. 29, 1986, American Chemical Society (US), L.A. MITSCHER et al.: "Total chemical synthesis and antitumor evaluation of the 9-aza analogue of N-(trifluoroacetyl)-4-demethoxydaunomycin", pages 1277-1281, see page 1277, compounds 8,9,14,15,16,17 (cited in the application) *

Also Published As

Publication number Publication date
CN1058781A (en) 1992-02-19
WO1991019725A2 (en) 1991-12-26
IE911965A1 (en) 1991-12-18
ZA914452B (en) 1992-06-24
AU653348B2 (en) 1994-09-29
PT97931A (en) 1992-03-31
MA22178A1 (en) 1991-12-31
AU8097391A (en) 1992-01-07
AP9100278A0 (en) 1991-07-31
FI925611A0 (en) 1992-12-10
FI925611A (en) 1992-12-10
YU103391A (en) 1994-04-05
CS178691A3 (en) 1992-01-15
IL98460A0 (en) 1992-07-15
HU9203720D0 (en) 1993-03-29
JPH06504034A (en) 1994-05-12
EP0533744A1 (en) 1993-03-31
CA2085120A1 (en) 1991-12-12
AP340A (en) 1994-05-13
NZ238490A (en) 1994-03-25
PL297164A1 (en) 1992-10-05

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