SK4894A3 - Derivatives of taxol analogues, preparation thereof and compositions containing them - Google Patents

Derivatives of taxol analogues, preparation thereof and compositions containing them Download PDF

Info

Publication number: SK4894A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; group; groups; formula; alkyl
Prior art date: 1991-07-16

Application number

SK48-94A

Other languages

English (en)

Slovak (sk)

Inventor

Jean-Dominique Bourzat

Alain Commercon

Daniel Guenard

Francoise Gueritte-Voegelein

Pierre Potier

Original Assignee

Rhone Poulenc Rorer Sa

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.)

1991-07-16

Filing date

1992-07-16

Publication date

1994-12-07

1992-07-16 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1994-12-07 Publication of SK4894A3 publication Critical patent/SK4894A3/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 26
238000002360 preparation method Methods 0.000 title claims abstract description 7
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical class O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title abstract description 5
-1 substituted alkyl radical Chemical class 0.000 claims abstract description 62
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 79
125000004432 carbon atom Chemical group C* 0.000 claims description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
239000011541 reaction mixture Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
239000011701 zinc Substances 0.000 claims description 7
229910052725 zinc Inorganic materials 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
150000003254 radicals Chemical group 0.000 abstract 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
125000000623 heterocyclic group Chemical group 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
230000000259 anti-tumor effect Effects 0.000 abstract 1
150000005840 aryl radicals Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
239000000243 solution Substances 0.000 description 28
239000005909 Kieselgur Substances 0.000 description 25
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239000000047 product Substances 0.000 description 15
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 14
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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238000000921 elemental analysis Methods 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
230000001575 pathological effect Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZVAFCKLQJCZGAP-UHFFFAOYSA-N 2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-UHFFFAOYSA-N 0.000 description 3
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229910003849 O-Si Inorganic materials 0.000 description 3
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 2
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CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK48-94A 1991-07-16 1992-07-16 Derivatives of taxol analogues, preparation thereof and compositions containing them SK4894A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9108937A FR2679230B1 (fr)	1991-07-16	1991-07-16	Nouveaux derives d'analogues du taxol, leur preparation et les compositions qui les contiennent.
PCT/FR1992/000687 WO1993002065A1 (fr)	1991-07-16	1992-07-16	Nouveaux derives d'analogues du taxol, leur preparation et les compositions qui les contiennent

Publications (1)

Publication Number	Publication Date
SK4894A3 true SK4894A3 (en)	1994-12-07

Family

ID=9415141

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK48-94A SK4894A3 (en)	1991-07-16	1992-07-16	Derivatives of taxol analogues, preparation thereof and compositions containing them

Country Status (17)

Country	Link
EP (2)	EP0596010A1 (cs)
JP (1)	JPH06509107A (cs)
AU (1)	AU2388092A (cs)
CA (1)	CA2113074A1 (cs)
CZ (1)	CZ9094A3 (cs)
FI (1)	FI940191A7 (cs)
FR (1)	FR2679230B1 (cs)
HU (1)	HUT66600A (cs)
IE (1)	IE922305A1 (cs)
MX (1)	MX9204140A (cs)
NO (1)	NO934723D0 (cs)
NZ (1)	NZ243548A (cs)
SK (1)	SK4894A3 (cs)
TW (1)	TW201740B (cs)
WO (1)	WO1993002065A1 (cs)
YU (1)	YU69892A (cs)
ZA (1)	ZA925245B (cs)

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5728850A (en) *	1991-09-23	1998-03-17	Florida State University	Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US5710287A (en) *	1991-09-23	1998-01-20	Florida State University	Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them
US6028205A (en) *	1991-09-23	2000-02-22	Florida State University	C2 tricyclic taxanes
US5721268A (en)	1991-09-23	1998-02-24	Florida State University	C7 taxane derivatives and pharmaceutical compositions containing them
US6005138A (en) *	1991-09-23	1999-12-21	Florida State University	Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US6018073A (en) *	1991-09-23	2000-01-25	Florida State University	Tricyclic taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US5489601A (en) *	1991-09-23	1996-02-06	Florida State University	Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US6011056A (en) *	1991-09-23	2000-01-04	Florida State University	C9 taxane derivatives and pharmaceutical compositions containing them
US5739362A (en) *	1991-09-23	1998-04-14	Florida State University	Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US6495704B1 (en)	1991-09-23	2002-12-17	Florida State University	9-desoxotaxanes and process for the preparation of 9-desoxotaxanes
US5998656A (en) *	1991-09-23	1999-12-07	Florida State University	C10 tricyclic taxanes
US5714513A (en) *	1991-09-23	1998-02-03	Florida State University	C10 taxane derivatives and pharmaceutical compositions
US6335362B1 (en)	1991-09-23	2002-01-01	Florida State University	Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
US5728725A (en) *	1991-09-23	1998-03-17	Florida State University	C2 taxane derivaties and pharmaceutical compositions containing them
US5654447A (en) *	1991-09-23	1997-08-05	Florida State University	Process for the preparation of 10-desacetoxybaccatin III
US6515009B1 (en)	1991-09-27	2003-02-04	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US5811447A (en)	1993-01-28	1998-09-22	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US5272171A (en) *	1992-02-13	1993-12-21	Bristol-Myers Squibb Company	Phosphonooxy and carbonate derivatives of taxol
US5294637A (en) *	1992-07-01	1994-03-15	Bristol-Myers Squibb Company	Fluoro taxols
US5614549A (en) *	1992-08-21	1997-03-25	Enzon, Inc.	High molecular weight polymer-based prodrugs
US5380751A (en) *	1992-12-04	1995-01-10	Bristol-Myers Squibb Company	6,7-modified paclitaxels
US5646176A (en)	1992-12-24	1997-07-08	Bristol-Myers Squibb Company	Phosphonooxymethyl ethers of taxane derivatives
US6491938B2 (en)	1993-05-13	2002-12-10	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US5981568A (en)	1993-01-28	1999-11-09	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US6066747A (en) *	1993-03-05	2000-05-23	Florida State University	Process for the preparation of 9-desoxotaxanes
US6710191B2 (en)	1993-03-05	2004-03-23	Florida State University	9β-hydroxytetracyclic taxanes
US5547981A (en) *	1993-03-09	1996-08-20	Enzon, Inc.	Taxol-7-carbazates
US5703247A (en) *	1993-03-11	1997-12-30	Virginia Tech Intellectual Properties, Inc.	2-Debenzoyl-2-acyl taxol derivatives and methods for making same
ES2205663T3 (es) *	1993-06-11	2004-05-01	PHARMACIA & UPJOHN COMPANY	Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen.
CA2129288C (en) *	1993-08-17	2000-05-16	Jerzy Golik	Phosphonooxymethyl esters of taxane derivatives
FR2711370B1 (fr) *	1993-10-18	1996-01-05	Rhone Poulenc Rorer Sa	Nouveaux taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
AU8052194A (en) *	1993-10-20	1995-05-08	Enzon, Inc.	2'- and/or 7- substituted taxoids
US5965566A (en) *	1993-10-20	1999-10-12	Enzon, Inc.	High molecular weight polymer-based prodrugs
US5880131A (en) *	1993-10-20	1999-03-09	Enzon, Inc.	High molecular weight polymer-based prodrugs
IL127598A (en) *	1994-01-28	2003-04-10	Upjohn Co	Process for preparing isotaxol analogs
AU724499B2 (en)	1996-05-06	2000-09-21	Florida State University	1-deoxy baccatin III, 1-deoxy taxol and 1-deoxy taxol analogs and method for the preparation thereof
AU710156B2 (en) *	1996-07-15	1999-09-16	Kabushiki Kaisha Yakult Honsha	Taxane derivatives and drugs containing the same
GB9705903D0 (en)	1997-03-21	1997-05-07	Elliott Gillian D	VP22 Proteins and uses thereof
WO1999032473A1 (en) *	1997-12-19	1999-07-01	Kabushiki Kaisha Yakult Honsha	Taxane derivatives
HK1047937A1 (zh) *	2000-02-02	2003-03-14	佛罗里达州立大学研究基金有限公司	C7氨基甲酰氧基取代的紫衫烷抗肿瘤剂
US6596737B2 (en) *	2000-02-02	2003-07-22	Fsu Research Foundation, Inc.	C10 carbamoyloxy substituted taxanes
CO5280224A1 (es)	2000-02-02	2003-05-30	Univ Florida State Res Found	Taxanos sustituidos con ester en c7, utiles como agentes antitumorales y composiciones farmaceuticas que los contienen
US6613083B2 (en)	2001-05-02	2003-09-02	Eckhard Alt	Stent device and method
PL368945A1 (en)	2001-11-30	2005-04-04	Bristol-Myers Squibb Company	Paclitaxel solvates
US20050187147A1 (en) *	2003-09-22	2005-08-25	Newman Michael J.	Compositions and methods for increasing drug efficiency
EP1737444A4 (en)	2004-03-05	2008-05-21	Univ Florida State Res Found	C7-LACTYLOXA-SUBSTITUTED TAXANE
CN104650012A (zh) *	2013-11-22	2015-05-27	天士力控股集团有限公司	一种紫杉烷类化合物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2601675B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent

1991
- 1991-07-16 FR FR9108937A patent/FR2679230B1/fr not_active Expired - Fee Related
1992
- 1992-07-14 TW TW081105531A patent/TW201740B/zh active
- 1992-07-14 NZ NZ24354892A patent/NZ243548A/en unknown
- 1992-07-14 ZA ZA925245A patent/ZA925245B/xx unknown
- 1992-07-15 IE IE230592A patent/IE922305A1/en not_active Application Discontinuation
- 1992-07-15 MX MX9204140A patent/MX9204140A/es unknown
- 1992-07-15 YU YU69892A patent/YU69892A/sh unknown
- 1992-07-16 CA CA002113074A patent/CA2113074A1/fr not_active Abandoned
- 1992-07-16 AU AU23880/92A patent/AU2388092A/en not_active Abandoned
- 1992-07-16 SK SK48-94A patent/SK4894A3/sk unknown
- 1992-07-16 CZ CS9490A patent/CZ9094A3/cs unknown
- 1992-07-16 JP JP5502629A patent/JPH06509107A/ja active Pending
- 1992-07-16 HU HU9400113A patent/HUT66600A/hu unknown
- 1992-07-16 EP EP92916744A patent/EP0596010A1/fr not_active Ceased
- 1992-07-16 EP EP92402046A patent/EP0524093A1/fr active Pending
- 1992-07-16 WO PCT/FR1992/000687 patent/WO1993002065A1/fr not_active Ceased
1993
- 1993-12-20 NO NO934723A patent/NO934723D0/no unknown
1994
- 1994-01-14 FI FI940191A patent/FI940191A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO934723L (no)	1993-12-20
ZA925245B (en)	1993-04-28
FI940191A0 (fi)	1994-01-14
CA2113074A1 (fr)	1993-02-04
HUT66600A (en)	1994-12-28
NZ243548A (en)	1994-07-26
NO934723D0 (no)	1993-12-20
CZ9094A3 (en)	1994-06-15
FR2679230A1 (fr)	1993-01-22
EP0524093A1 (fr)	1993-01-20
AU2388092A (en)	1993-02-23
FR2679230B1 (fr)	1993-11-19
TW201740B (cs)	1993-03-11
HU9400113D0 (en)	1994-05-30
JPH06509107A (ja)	1994-10-13
FI940191A7 (fi)	1994-01-14
IE922305A1 (en)	1993-01-27
MX9204140A (es)	1993-01-01
YU69892A (sh)	1995-10-03
EP0596010A1 (fr)	1994-05-11
WO1993002065A1 (fr)	1993-02-04

Publication	Publication Date	Title
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FI61187B (fi)	1982-02-26	Foerfarande foer framstaellning av antitumoera 1,2-5,6-dianhydro-3,4-di-0-acylgalaktitolderivat
SU803351A1 (ru)	1983-08-07	Ацетиламиноалкил- @ -диазокетоны,обладающие противоопухолевой активностью
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