SK277925B6 - Method of stereoselective preparation of phenylisoserine derivatives - Google Patents

Method of stereoselective preparation of phenylisoserine derivatives Download PDF

Info

Publication number: SK277925B6
Authority: SK; Slovakia
Prior art keywords: formula; tert; alcohol; group; configuration
Prior art date: 1990-05-22

Application number

SK1451-91A

Other languages

English (en)

Slovak (sk)

Inventor

Arlene Correa

Jean-Noel Denis

Andrew-Elliot Greene

Original Assignee

Arlene Correa

Jean-Noel Denis

Andrew-Elliot Greene

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.)

1990-05-22

Filing date

1991-05-16

Publication date

1995-08-09

1991-05-16 Application filed by Arlene Correa, Jean-Noel Denis, Andrew-Elliot Greene filed Critical Arlene Correa

1995-08-09 Publication of SK277925B6 publication Critical patent/SK277925B6/sk

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 5
230000000707 stereoselective effect Effects 0.000 title claims description 3
HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical class OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 title claims 2
239000000203 mixture Substances 0.000 claims abstract description 21
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 14
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims abstract description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical group CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 claims description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
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 4
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 3
235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
FWOBBEOKTITUHK-UHFFFAOYSA-N tert-butyl n-benzylcarbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC=C1 FWOBBEOKTITUHK-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
235000010755 mineral Nutrition 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000001979 organolithium group Chemical group 0.000 claims description 2
239000012286 potassium permanganate Substances 0.000 claims description 2
150000003303 ruthenium Chemical class 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims 1
239000007800 oxidant agent Substances 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 6
125000006239 protecting group Chemical group 0.000 abstract description 2
QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical compound CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 abstract 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
-1 1-ethoxyethyl radical Chemical class 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000000126 substance Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
TYLVGQKNNUHXIP-MHHARFCSSA-N 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)C=4C=CC=CC=4)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 TYLVGQKNNUHXIP-MHHARFCSSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000001282 iso-butane Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
AJPQGDKKFMFVDR-UHFFFAOYSA-N tert-butyl n-(2-hydroxy-1-phenylbut-3-enyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C(O)C=C)C1=CC=CC=C1 AJPQGDKKFMFVDR-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229930182986 10-Deacetyltaxol Natural products 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
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 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
229930190007 Baccatin Natural products 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000719 anti-leukaemic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000007787 solid Substances 0.000 description 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 description 1
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 1
DETFWVOVMJAGMA-UHFFFAOYSA-N tert-butyl n-[2-(1-ethoxyethoxy)-1-phenylbut-3-enyl]carbamate Chemical compound CCOC(C)OC(C=C)C(NC(=O)OC(C)(C)C)C1=CC=CC=C1 DETFWVOVMJAGMA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate 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
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Semiconductor Integrated Circuits (AREA)
Indole Compounds (AREA)

SK1451-91A 1990-05-22 1991-05-16 Method of stereoselective preparation of phenylisoserine derivatives SK277925B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9006368A FR2662440B1 (fr)	1990-05-22	1990-05-22	Procede de preparation stereoselective de derives de la phenylisoserine.

Publications (1)

Publication Number	Publication Date
SK277925B6 true SK277925B6 (en)	1995-08-09

Family

ID=9396838

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1451-91A SK277925B6 (en)	1990-05-22	1991-05-16	Method of stereoselective preparation of phenylisoserine derivatives

Country Status (23)

Country	Link
US (1)	US5290957A (sh)
EP (1)	EP0530286B1 (sh)
JP (1)	JPH05506864A (sh)
AT (1)	ATE109456T1 (sh)
AU (1)	AU648319B2 (sh)
CA (1)	CA2079313A1 (sh)
CZ (1)	CZ279927B6 (sh)
DE (1)	DE69103265T2 (sh)
DK (1)	DK0530286T3 (sh)
ES (1)	ES2057899T3 (sh)
FI (1)	FI924568A0 (sh)
FR (1)	FR2662440B1 (sh)
HU (1)	HU212728B (sh)
IE (1)	IE64276B1 (sh)
IL (1)	IL98190A (sh)
NO (1)	NO179942C (sh)
NZ (1)	NZ238206A (sh)
PT (1)	PT97745B (sh)
RU (1)	RU2091368C1 (sh)
SK (1)	SK277925B6 (sh)
WO (1)	WO1991017977A1 (sh)
YU (1)	YU89691A (sh)
ZA (1)	ZA913828B (sh)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2658510B1 (fr) *	1990-02-21	1992-04-30	Rhone Poulenc Sante	Nouveau derive de la beta-phenylisoserine, sa preparation et son emploi.
CA2092705C (en) *	1991-07-17	1995-11-07	Koji Saito	Compound having antitumor activity, nsc-lsc1, and process for producing the same
FR2680506B1 (fr) *	1991-08-19	1994-09-02	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la beta-phenylisoserine et leur utilisation.
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
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
US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
KR960006762B1 (ko) *	1992-02-29	1996-05-23	삼성전자주식회사	화상부호화를 위한 효율적인 2차원 데이타의 주사선택회로
FR2696454B1 (fr) *	1992-10-05	1994-11-25	Rhone Poulenc Rorer Sa	Procédé de préparation stéréosélective d'un dérivé de la beta-phénylisosérine et son utilisation pour la préparation de dérivés du Taxane.
MX9307777A (es)	1992-12-15	1994-07-29	Upjohn Co	7-HALO-Y 7ß, 8ß-METANO-TAXOLES, USO ANTINEOPLASTICO Y COMPOSICIONES FARMACEUTICAS QUE LOS CONTIENEN.
EP0982302B1 (en) *	1993-06-11	2004-04-14	PHARMACIA & UPJOHN COMPANY	Delta 6,7-taxols antineoplastic use and pharmaceutical compositions containing them
US5405972A (en) *	1993-07-20	1995-04-11	Florida State University	Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes
US6005120A (en)	1993-07-20	1999-12-21	Florida State University	Tricyclic and tetracyclic taxanes
IL112412A (en) *	1994-01-28	2000-02-29	Upjohn Co	Delta 12,13-iso-taxol analogs and antineoplastic pharmaceutical compositions containing them
US6638502B1 (en) *	1997-04-28	2003-10-28	Gencell Sas	Adenovirus-mediated intratumoral delivery of an angiogenesis antagonist for the treatment of tumors
FR2794771B1 (fr)	1999-06-11	2001-08-10	Aventis Pharma Sa	Adenovirus recombinants codant pour le transporteur specifique de l'iode (nis)
EP1229934B1 (en)	1999-10-01	2014-03-05	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
CA2772681C (en) *	2009-09-23	2017-01-03	Zhejiang Jiuzhou Pharmaceutical Co., Ltd.	Process for manufacture of n-acylbphenyl alanine
CA2846372C (en)	2011-09-08	2021-01-12	New York University	Oncolytic herpes simplex virus and therapeutic uses thereof
WO2013096455A1 (en)	2011-12-20	2013-06-27	Dana-Farber Cancer Institute, Inc.	Methods for diagnosing and treating oncogenic kras-associated cancer
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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
IL95436A (en) *	1989-08-23	1996-07-23	Centre Nat Rech Scient	Process for preparing the history of phenylisosarine

1990
- 1990-05-22 FR FR9006368A patent/FR2662440B1/fr not_active Expired - Lifetime
1991
- 1991-05-16 SK SK1451-91A patent/SK277925B6/sk unknown
- 1991-05-16 CZ CS911451A patent/CZ279927B6/cs unknown
- 1991-05-20 IL IL9819091A patent/IL98190A/en not_active IP Right Cessation
- 1991-05-21 ES ES91910270T patent/ES2057899T3/es not_active Expired - Lifetime
- 1991-05-21 IE IE173791A patent/IE64276B1/en not_active IP Right Cessation
- 1991-05-21 EP EP91910270A patent/EP0530286B1/fr not_active Expired - Lifetime
- 1991-05-21 DK DK91910270.7T patent/DK0530286T3/da active
- 1991-05-21 ZA ZA913828A patent/ZA913828B/xx unknown
- 1991-05-21 JP JP91509580A patent/JPH05506864A/ja active Pending
- 1991-05-21 CA CA002079313A patent/CA2079313A1/fr not_active Abandoned
- 1991-05-21 US US07/949,548 patent/US5290957A/en not_active Expired - Fee Related
- 1991-05-21 AT AT91910270T patent/ATE109456T1/de not_active IP Right Cessation
- 1991-05-21 WO PCT/FR1991/000406 patent/WO1991017977A1/fr active IP Right Grant
- 1991-05-21 NZ NZ238206A patent/NZ238206A/xx unknown
- 1991-05-21 YU YU89691A patent/YU89691A/sh unknown
- 1991-05-21 DE DE69103265T patent/DE69103265T2/de not_active Expired - Fee Related
- 1991-05-21 AU AU79693/91A patent/AU648319B2/en not_active Ceased
- 1991-05-21 RU RU9192016318A patent/RU2091368C1/ru active
- 1991-05-21 HU HU9203651A patent/HU212728B/hu not_active IP Right Cessation
- 1991-05-22 PT PT97745A patent/PT97745B/pt not_active IP Right Cessation
1992
- 1992-10-09 FI FI924568A patent/FI924568A0/fi not_active Application Discontinuation
- 1992-11-20 NO NO924488A patent/NO179942C/no unknown

Also Published As

Publication number	Publication date
HU9203651D0 (en)	1993-03-29
CA2079313A1 (fr)	1991-11-23
ZA913828B (en)	1992-02-26
EP0530286A1 (fr)	1993-03-10
WO1991017977A1 (fr)	1991-11-28
PT97745A (pt)	1992-02-28
AU648319B2 (en)	1994-04-21
DE69103265T2 (de)	1994-12-22
HU212728B (en)	1996-10-28
NO924488D0 (no)	1992-11-20
DK0530286T3 (da)	1994-09-12
FR2662440B1 (fr)	1992-07-31
RU2091368C1 (ru)	1997-09-27
IL98190A0 (en)	1992-06-21
JPH05506864A (ja)	1993-10-07
US5290957A (en)	1994-03-01
IL98190A (en)	1995-12-31
EP0530286B1 (fr)	1994-08-03
NO179942C (no)	1997-01-15
AU7969391A (en)	1991-12-10
FI924568L (fi)	1992-10-09
NO179942B (no)	1996-10-07
IE911737A1 (en)	1991-12-04
ES2057899T3 (es)	1994-10-16
FI924568A0 (fi)	1992-10-09
IE64276B1 (en)	1995-07-26
CZ279927B6 (cs)	1995-08-16
CS9101451A2 (en)	1991-12-17
NO924488L (no)	1992-11-20
DE69103265D1 (de)	1994-09-08
HUT62260A (en)	1993-04-28
PT97745B (pt)	1998-10-30
FR2662440A1 (fr)	1991-11-29
ATE109456T1 (de)	1994-08-15
NZ238206A (en)	1993-05-26
YU89691A (sh)	1994-01-20

Publication	Publication Date	Title
SK277925B6 (en)	1995-08-09	Method of stereoselective preparation of phenylisoserine derivatives
US5292921A (en)	1994-03-08	Process for the enantioselective preparation of phenylisoserine derivatives
DE69001732T2 (de)	1993-10-07	Verfahren zur enantioselektiven Herstellung von Phenylisoserin-Derivaten.
DE69404991T2 (de)	1998-01-22	Verfahren zur herstellung einer oxazolidincarbon säure nützlich für die herstellung von therapeutischen taxoiden
US5304670A (en)	1994-04-19	Process for the enantioselective preparation of phenylisoserine derivatives
RU2109010C1 (ru)	1998-04-20	ПРОИЗВОДНОЕ β -ФЕНИЛИЗОСЕРИНА, СПОСОБ ЕГО СТЕРЕОСЕЛЕКТИВНОГО ПОЛУЧЕНИЯ, ИСХОДНОЕ СОЕДИНЕНИЕ ДЛЯ ЕГО ПОЛУЧЕНИЯ, СПОСОБ ПОЛУЧЕНИЯ ТАКСАНА И ПРОМЕЖУТОЧНЫЕ ПРОДУКТЫ
EP2125765A1 (en)	2009-12-02	Method of preparing taxane derivatives and intermediates used therein
AU2003267049B2 (en)	2010-02-11	Taxane derivatives functionalized at the 14- position and a process for the preparation thereof
JPWO2003004515A1 (ja)	2004-10-28	エストラジオール誘導体の製造方法、当該方法で用いる中間体及びその製造方法