SK280329B6 - Anhydridy kyselín, spôsob ich prípravy a ich použi - Google Patents

Anhydridy kyselín, spôsob ich prípravy a ich použi Download PDF

Info

Publication number: SK280329B6
Authority: SK; Slovakia
Prior art keywords: group; butoxycarbonyl; hydroxy; general formula; protecting
Prior art date: 1992-02-07

Application number

SK929-94A

Other languages

English (en)

Slovak (sk)

Other versions

SK92994A3 (en

Inventor

Jean-Manuel Mas

Original Assignee

Rhone-Poulenc Rorer S.A.

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.)

1992-02-07

Filing date

1993-02-04

Publication date

1999-11-08

1993-02-04 Application filed by Rhone-Poulenc Rorer S.A. filed Critical Rhone-Poulenc Rorer S.A.

1995-04-12 Publication of SK92994A3 publication Critical patent/SK92994A3/sk

1999-11-08 Publication of SK280329B6 publication Critical patent/SK280329B6/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
150000008065 acid anhydrides Chemical class 0.000 title description 2
150000008064 anhydrides Chemical class 0.000 claims abstract description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
-1 t-butoxycarbonyl Chemical group 0.000 claims description 33
125000006239 protecting group Chemical group 0.000 claims description 15
238000000034 method Methods 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)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)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 claims description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
239000012024 dehydrating agents‎ Substances 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229930014667 baccatin III Natural products 0.000 claims description 2
150000004200 baccatin III derivatives Chemical class 0.000 claims description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims 2
125000000160 oxazolidinyl group Chemical group 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
150000005840 aryl radicals Chemical group 0.000 abstract 1
230000001681 protective effect Effects 0.000 abstract 1
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 abstract 1
239000000047 product Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229930012538 Paclitaxel Natural products 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
230000003213 activating effect Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229960001592 paclitaxel Drugs 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound 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 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000032050 esterification Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
150000004579 taxol derivatives Chemical class 0.000 description 3
239000008096 xylene Substances 0.000 description 3
150000003738 xylenes Chemical class 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000003927 aminopyridines Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
150000003952 β-lactams Chemical class 0.000 description 2
RBANVFAOLCONSH-JQXSQYPDSA-N (2r,3s)-2-(1-ethoxyethoxy)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CCOC(C)O[C@@H](C(O)=O)[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1 RBANVFAOLCONSH-JQXSQYPDSA-N 0.000 description 1
VAHXMEZCPGHDBJ-QWHCGFSZSA-N (4s,5r)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)[C@@H]1OC(C)(C)N(C(=O)OC(C)(C)C)[C@H]1C1=CC=CC=C1 VAHXMEZCPGHDBJ-QWHCGFSZSA-N 0.000 description 1
RBANVFAOLCONSH-UHFFFAOYSA-N 2-(1-ethoxyethoxy)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CCOC(C)OC(C(O)=O)C(NC(=O)OC(C)(C)C)C1=CC=CC=C1 RBANVFAOLCONSH-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
DMJVNYSMZWQJHF-QEGGNFSNSA-N 3-O-tert-butyl 5-O-[(4S,5R)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carbonyl] (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate Chemical compound C1([C@@H]2N(C(C)(C)O[C@H]2C(=O)OC(=O)[C@H]2[C@@H](N(C(O2)(C)C)C(=O)OC(C)(C)C)C=2C=CC=CC=2)C(=O)OC(C)(C)C)=CC=CC=C1 DMJVNYSMZWQJHF-QEGGNFSNSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001412 amines Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000005239 aroylamino group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940063683 taxotere Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- 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
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- 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
- 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
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Polyesters Or Polycarbonates (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK929-94A 1992-02-07 1993-02-04 Anhydridy kyselín, spôsob ich prípravy a ich použi SK280329B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9201380A FR2687145B1 (fr)	1992-02-07	1992-02-07	Nouveaux anhydrides d'acides, leur preparation et leur emplot et
PCT/FR1993/000111 WO1993016058A1 (fr)	1992-02-07	1993-02-04	Nouveaux anhydrides d'acides, leur preparation et leur emploi

Publications (2)

Publication Number	Publication Date
SK92994A3 SK92994A3 (en)	1995-04-12
SK280329B6 true SK280329B6 (sk)	1999-11-08

Family

ID=9426425

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK929-94A SK280329B6 (sk)	1992-02-07	1993-02-04	Anhydridy kyselín, spôsob ich prípravy a ich použi

Country Status (24)

Country	Link
US (1)	US5606068A (de)
EP (1)	EP0625146B1 (de)
JP (1)	JP2894636B2 (de)
KR (1)	KR950700266A (de)
AT (1)	ATE146463T1 (de)
AU (1)	AU686096B2 (de)
CA (1)	CA2126461C (de)
CZ (1)	CZ283542B6 (de)
DE (1)	DE69306760T2 (de)
DK (1)	DK0625146T3 (de)
ES (1)	ES2095041T3 (de)
FI (1)	FI109790B (de)
FR (1)	FR2687145B1 (de)
GR (1)	GR3022102T3 (de)
HU (1)	HU212418B (de)
MX (1)	MX9300585A (de)
NO (1)	NO304310B1 (de)
NZ (1)	NZ249163A (de)
PL (2)	PL171713B1 (de)
RU (1)	RU2104274C1 (de)
SK (1)	SK280329B6 (de)
TW (1)	TW254933B (de)
WO (1)	WO1993016058A1 (de)
ZA (1)	ZA93822B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7288665B1 (en)	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
JP4776843B2 (ja)	1999-10-01	2011-09-21	イムノゲンインコーポレーティッド	免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法
AU2003273671A1 (en) *	2002-10-09	2004-05-04	Phytogen Life Sciences, Inc.	Novel taxanes and methods related to use and preparation thereof
US7202370B2 (en) *	2003-10-27	2007-04-10	Conor Medsystems, Inc.	Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III

Family Cites Families (4)

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FR2601675B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du taxol
FR2629819B1 (fr) *	1988-04-06	1990-11-16	Rhone Poulenc Sante	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
US5175315A (en) *	1989-05-31	1992-12-29	Florida State University	Method for preparation of taxol using β-lactam

1992
- 1992-02-07 FR FR9201380A patent/FR2687145B1/fr not_active Expired - Lifetime
1993
- 1993-02-03 MX MX9300585A patent/MX9300585A/es unknown
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- 1993-02-04 PL PL93304720A patent/PL171713B1/pl unknown
- 1993-02-04 DE DE69306760T patent/DE69306760T2/de not_active Expired - Lifetime
- 1993-02-04 TW TW082100752A patent/TW254933B/zh not_active IP Right Cessation
- 1993-02-04 CA CA002126461A patent/CA2126461C/fr not_active Expired - Lifetime
- 1993-02-04 AT AT93904151T patent/ATE146463T1/de active
- 1993-02-04 AU AU35049/93A patent/AU686096B2/en not_active Expired
- 1993-02-04 WO PCT/FR1993/000111 patent/WO1993016058A1/fr not_active Ceased
- 1993-02-04 JP JP5513822A patent/JP2894636B2/ja not_active Expired - Lifetime
- 1993-02-04 EP EP93904151A patent/EP0625146B1/de not_active Expired - Lifetime
- 1993-02-04 DK DK93904151.3T patent/DK0625146T3/da active
- 1993-02-04 SK SK929-94A patent/SK280329B6/sk not_active IP Right Cessation
- 1993-02-04 NZ NZ249163A patent/NZ249163A/en not_active IP Right Cessation
- 1993-02-04 KR KR1019940702714A patent/KR950700266A/ko not_active Expired - Lifetime
- 1993-02-04 CZ CZ941871A patent/CZ283542B6/cs not_active IP Right Cessation
- 1993-02-04 RU RU94040727/04A patent/RU2104274C1/ru active
- 1993-02-04 US US08/599,102 patent/US5606068A/en not_active Expired - Lifetime
- 1993-02-04 ES ES93904151T patent/ES2095041T3/es not_active Expired - Lifetime
- 1993-02-04 PL PL93314333A patent/PL171667B1/pl unknown
- 1993-02-05 ZA ZA93822A patent/ZA93822B/xx unknown
1994
- 1994-08-04 NO NO942896A patent/NO304310B1/no not_active IP Right Cessation
- 1994-08-05 FI FI943644A patent/FI109790B/fi not_active IP Right Cessation
1996
- 1996-12-19 GR GR960402006T patent/GR3022102T3/el unknown

Also Published As

Publication number	Publication date
CZ283542B6 (cs)	1998-04-15
AU686096B2 (en)	1998-02-05
JP2894636B2 (ja)	1999-05-24
PL171667B1 (en)	1997-06-30
TW254933B (de)	1995-08-21
KR950700266A (ko)	1995-01-16
US5606068A (en)	1997-02-25
NO942896D0 (de)	1994-08-04
JPH07503721A (ja)	1995-04-20
CA2126461C (fr)	2003-05-13
HUT71618A (en)	1996-01-29
EP0625146B1 (de)	1996-12-18
SK92994A3 (en)	1995-04-12
NO304310B1 (no)	1998-11-30
RU2104274C1 (ru)	1998-02-10
RU94040727A (ru)	1996-06-20
MX9300585A (es)	1993-08-01
FI109790B (fi)	2002-10-15
ES2095041T3 (es)	1997-02-01
AU3504993A (en)	1993-09-03
DE69306760T2 (de)	1997-06-05
GR3022102T3 (en)	1997-03-31
FI943644L (fi)	1994-08-05
CA2126461A1 (fr)	1993-08-19
FI943644A0 (fi)	1994-08-05
NZ249163A (en)	1997-01-29
ZA93822B (en)	1993-09-09
CZ187194A3 (en)	1994-12-15
NO942896L (no)	1994-08-04
FR2687145B1 (fr)	1994-03-25
ATE146463T1 (de)	1997-01-15
HU9402002D0 (en)	1994-09-28
DE69306760D1 (de)	1997-01-30
EP0625146A1 (de)	1994-11-23
PL171713B1 (pl)	1997-06-30
HU212418B (en)	1996-06-28
WO1993016058A1 (fr)	1993-08-19
DK0625146T3 (da)	1997-01-06
FR2687145A1 (fr)	1993-08-13

Legal Events

Date	Code	Title	Description
2013-04-03	MK4A	Patent expired	Expiry date: 20130204

Publication	Publication Date	Title
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KR100311198B1 (ko)	2002-04-24	탁산유도체의제조방법
JP3014762B2 (ja)	2000-02-28	タキサン誘導体の製造法
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