WO1989010929A3 - New l-fucose analogs, method of preparation, application of such analogs to the preparation of new glycals, anthracyclines obtained with said glycals and utilization of said anthracyclines as drugs - Google Patents

New l-fucose analogs, method of preparation, application of such analogs to the preparation of new glycals, anthracyclines obtained with said glycals and utilization of said anthracyclines as drugs Download PDF

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Publication number
WO1989010929A3
WO1989010929A3 PCT/FR1989/000217 FR8900217W WO8910929A3 WO 1989010929 A3 WO1989010929 A3 WO 1989010929A3 FR 8900217 W FR8900217 W FR 8900217W WO 8910929 A3 WO8910929 A3 WO 8910929A3
Authority
WO
WIPO (PCT)
Prior art keywords
glycals
anthracyclines
preparation
new
analogs
Prior art date
Application number
PCT/FR1989/000217
Other languages
French (fr)
Other versions
WO1989010929A2 (en
Inventor
Jean-Pierre Gesson
Patricia Petit
Martine Mondon
Jean-Claude Jacquesy
Hans Peter Kraemer
Original Assignee
Hoechst Lab
Behringwerke Ag
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 Hoechst Lab, Behringwerke Ag filed Critical Hoechst Lab
Priority to KR1019900700006A priority Critical patent/KR900701805A/en
Publication of WO1989010929A2 publication Critical patent/WO1989010929A2/en
Priority to DK000990A priority patent/DK990A/en
Priority to FI900051A priority patent/FI900051A/en
Publication of WO1989010929A3 publication Critical patent/WO1989010929A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
    • 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
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • 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
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/02—Acyclic radicals

Abstract

The present invention relates to new L-Fucose analogs, their method of preparation, the application of such analogs to the preparation of new glycals, anthracyclines obtained by using such glycals and utilization of such anthracyclines as drugs. The glycals are obtained from L-Fucose and/or its analogs having the formula (1') and have the formula (2), wherein R is an optionally substituted linear or branched alkyl group or an optionally substituted aryl group, whith the exception of a CH2OR group or a CH2OR3 group, R3 having the same meaning as R.
PCT/FR1989/000217 1988-05-04 1989-05-03 New l-fucose analogs, method of preparation, application of such analogs to the preparation of new glycals, anthracyclines obtained with said glycals and utilization of said anthracyclines as drugs WO1989010929A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1019900700006A KR900701805A (en) 1988-05-04 1989-05-03 Novel L-fucos homologues, methods for their preparation, application of this analogue to the manufacture of novel glycols, anthracycline obtained using these glycols and the use of anthracycline as a medicament
DK000990A DK990A (en) 1988-05-04 1990-01-03 L-FUCOSE ANALOGS, PROCEDURES FOR PREPARING THEREOF, USING THE ANALOGS FOR PREPARING UNKNOWN GLYCALS, ANTHRACYCLINES OBTAINED BY USING THE GLYCALS AND USING THE USE OF ANY USE
FI900051A FI900051A (en) 1988-05-04 1990-01-04 NYA L-FUKOS ANALOGER, FOERFARANDE FOER FRAMSTAELLNING DAERAV, ANVAENDNINGEN AV DESSA ANALOGER FOER FRAMSTAELLNING AV NYA GLYKALER, ANTRACYKLINER SOM ERHAOLLITS MEDELST DESSA GLYKALER SAMT ANVAENDNINGEN AV SAG

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8805969A FR2630914A1 (en) 1988-05-04 1988-05-04 NOVEL ANALOGUES OF L-FUCOSE, PROCESS FOR THE PREPARATION THEREOF, APPLICATION OF THESE ANALOGUES TO THE PREPARATION OF NOVEL GLYCALS, ANTHRACYCLINES OBTAINED BY SAID GLYCALS AND USE OF SAID ANTHRACYCLINS AS MEDICAMENTS
FR88/05969 1988-05-04

Publications (2)

Publication Number Publication Date
WO1989010929A2 WO1989010929A2 (en) 1989-11-16
WO1989010929A3 true WO1989010929A3 (en) 1990-02-22

Family

ID=9365971

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1989/000217 WO1989010929A2 (en) 1988-05-04 1989-05-03 New l-fucose analogs, method of preparation, application of such analogs to the preparation of new glycals, anthracyclines obtained with said glycals and utilization of said anthracyclines as drugs

Country Status (9)

Country Link
EP (1) EP0341154A3 (en)
JP (1) JPH02504153A (en)
KR (1) KR900701805A (en)
AU (1) AU3563089A (en)
DK (1) DK990A (en)
FI (1) FI900051A (en)
FR (1) FR2630914A1 (en)
PT (1) PT90446A (en)
WO (1) WO1989010929A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5300683A (en) * 1988-09-28 1994-04-05 Exfluor Research Corporation Fluorination of acetals, ketals and orthoesters
ES2458541T3 (en) 2008-05-02 2014-05-06 Seattle Genetics, Inc. Methods and compositions for making antibodies and antibody derivatives with reduced core fucosylation
MX356671B (en) 2010-08-05 2018-06-08 Seattle Genetics Inc Methods of inhibition of protein fucosylation in vivo using fucose analogs.
US10350228B2 (en) 2012-08-23 2019-07-16 Seattle Genetics, Inc. Treatment of sickle cell disease and inflammatory conditions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1980000305A1 (en) * 1978-07-26 1980-03-06 Us Commerce 7-0-(2,6-dideoxy-a-l-lyxo-hexopyranosyl)-desmethoxydaunomycinone,adriamycinone,and carminomycinone

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4301276A (en) * 1980-03-07 1981-11-17 Purdue University Synthesis of daunosamine hydrochloride and intermediates used in its preparation
US4302449A (en) * 1980-09-02 1981-11-24 Board Of Control Of Michigan Technological University Carminomycin analogue
JPS61236792A (en) * 1985-04-12 1986-10-22 Sanraku Inc Novel anthracycline antibiotic
DE3712350A1 (en) * 1987-04-11 1988-10-20 Behringwerke Ag SEMISYNTHETIC RHODOMYCINES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS CYTOSTATICS

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1980000305A1 (en) * 1978-07-26 1980-03-06 Us Commerce 7-0-(2,6-dideoxy-a-l-lyxo-hexopyranosyl)-desmethoxydaunomycinone,adriamycinone,and carminomycinone

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CARBOHYDRATE RESEARCH, vol. 95, 1981, pages 131-141, Elsevier Scientific Publishing Co., Amsterdam, NL, J. DEFAYE et al.: 'Synthèse des L-fucose et L(3-2H)fucose à partir du D-mannose' *
JOURNAL OF MEDICINAL CHEMISTRY, vol. 22, no. 8, août 1979, pages 971-976, American Chemical Society, US, J.A. MAY, Jr. et al.: 'Synthesis and biological activity of potential anti-metabolites of L-fucose' *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 104, no. 24, 1 décembre 1982, pages 6816 - 6818, American Chemical Society^, US, E.J. COREY et al.: 'Total synthesis of aplasmomycin. Stereocontrolled contruction of the C(3)-C(17) fragment' *
P.M. Collins: 'Carbohydrates' 187, Chapman & Hall (Londres, GB), voir page 225, F-00045, pages 226-7, F-00050 *
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 36, no. 21, 22 octobre 1971, pages 3242-3243, R.B. ROY et al.: 'Multicarbon chain extension of sugars through acetylenic intermediates. A hexadecitol' *
W. Pigman, D. Horton: 'The Carbohydrates, Chemistry and Biochemistry', vol. 1B, 1980, Academic Press (New York, US), voir page 844, lignes 16-23, page 849, lignes 16-18 *

Also Published As

Publication number Publication date
FI900051A0 (en) 1990-01-04
FR2630914A1 (en) 1989-11-10
DK990A (en) 1990-03-05
KR900701805A (en) 1990-12-04
EP0341154A2 (en) 1989-11-08
DK990D0 (en) 1990-01-03
WO1989010929A2 (en) 1989-11-16
FI900051A (en) 1990-01-04
JPH02504153A (en) 1990-11-29
PT90446A (en) 1989-11-30
EP0341154A3 (en) 1991-10-02
AU3563089A (en) 1989-11-29

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