JPH0684364B2 - 転位型タキソール化合物及びそのタキソール化合物を使用するインビボ活性の試験方法 - Google Patents

転位型タキソール化合物及びそのタキソール化合物を使用するインビボ活性の試験方法

Info

Publication number: JPH0684364B2
Authority: JP; Japan
Prior art keywords: taxol; compound; ring; compounds; producing
Prior art date: 1991-03-18
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP4054677A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0578342A (ja

Inventor

ジーアイキングストンディヴィッド

サマラニャーケガミニ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BAAJINIA TETSUKU INTEREKUCHUARU PUROPATEIISU Inc

Original Assignee

BAAJINIA TETSUKU INTEREKUCHUARU PUROPATEIISU Inc

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.)

1991-03-18

Filing date

1992-03-13

Publication date

1994-10-26

1992-03-13 Application filed by BAAJINIA TETSUKU INTEREKUCHUARU PUROPATEIISU Inc filed Critical BAAJINIA TETSUKU INTEREKUCHUARU PUROPATEIISU Inc

1993-03-30 Publication of JPH0578342A publication Critical patent/JPH0578342A/ja

1994-10-26 Publication of JPH0684364B2 publication Critical patent/JPH0684364B2/ja

2009-10-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

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 claims abstract description 132
238000012360 testing method Methods 0.000 title claims abstract description 20
238000000034 method Methods 0.000 title claims description 25
230000000694 effects Effects 0.000 title abstract description 29
238000001727 in vivo Methods 0.000 title abstract description 20
229960001592 paclitaxel Drugs 0.000 claims abstract description 157
229930012538 Paclitaxel Natural products 0.000 claims abstract description 124
150000001875 compounds Chemical class 0.000 claims abstract description 45
-1 triethyloxonium tetrafluoroborate Chemical compound 0.000 claims abstract description 39
125000003566 oxetanyl group Chemical group 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 14
239000012359 Methanesulfonyl chloride Substances 0.000 claims abstract description 7
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims abstract description 7
230000004071 biological effect Effects 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 10
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical group CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims description 6
239000002254 cytotoxic agent Substances 0.000 claims description 5
229940127089 cytotoxic agent Drugs 0.000 claims description 5
231100000599 cytotoxic agent Toxicity 0.000 claims description 5
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 3
230000008569 process Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
150000004579 taxol derivatives Chemical class 0.000 abstract description 26
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract description 17
239000012346 acetyl chloride Substances 0.000 abstract description 17
238000003556 assay Methods 0.000 abstract description 15
102000004243 Tubulin Human genes 0.000 abstract description 9
108090000704 Tubulin Proteins 0.000 abstract description 9
238000004113 cell culture Methods 0.000 abstract description 8
239000003153 chemical reaction reagent Substances 0.000 abstract description 6
230000003013 cytotoxicity Effects 0.000 abstract 1
231100000135 cytotoxicity Toxicity 0.000 abstract 1
239000000047 product Substances 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 12
238000005259 measurement Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 9
239000000126 substance Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 8
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000012512 characterization method Methods 0.000 description 6
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000004949 mass spectrometry Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000010561 standard procedure Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002246 antineoplastic agent Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
125000002456 taxol group Chemical group 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000012039 electrophile Substances 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
229940102001 zinc bromide Drugs 0.000 description 4
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 3
229930014626 natural product Natural products 0.000 description 3
TYLVGQKNNUHXIP-IDZUEFMLSA-N 10-Deacetyl-7-epi-taxol Natural products O=C(O[C@@H]1C(C)=C2[C@@H](O)C(=O)[C@@]3(C)[C@H](O)C[C@@H]4[C@@](OC(=O)C)([C@H]3[C@H](OC(=O)c3ccccc3)[C@](O)(C2(C)C)C1)CO4)[C@H](O)[C@@H](NC(=O)c1ccccc1)c1ccccc1 TYLVGQKNNUHXIP-IDZUEFMLSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
AZYTZQYCOBXDGY-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=CC=N1 AZYTZQYCOBXDGY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000000063 antileukemic agent Substances 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000013058 crude material Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
231100000433 cytotoxic Toxicity 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
150000004141 diterpene derivatives Chemical class 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
230000007017 scission Effects 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
238000005406 washing Methods 0.000 description 2
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N CHCl3 Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000012925 reference material Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

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
- 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
- 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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP4054677A 1991-03-18 1992-03-13 転位型タキソール化合物及びそのタキソール化合物を使用するインビボ活性の試験方法 Expired - Lifetime JPH0684364B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US67043291A	1991-03-18	1991-03-18
US07/670432		1991-03-18

Publications (2)

Publication Number	Publication Date
JPH0578342A JPH0578342A (ja)	1993-03-30
JPH0684364B2 true JPH0684364B2 (ja)	1994-10-26

Family

ID=24690379

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4054677A Expired - Lifetime JPH0684364B2 (ja)	1991-03-18	1992-03-13	転位型タキソール化合物及びそのタキソール化合物を使用するインビボ活性の試験方法

Country Status (5)

Country	Link
EP (1)	EP0505047B1 (2)
JP (1)	JPH0684364B2 (2)
AT (1)	ATE137229T1 (2)
DE (1)	DE69210078D1 (2)
TW (1)	TW223634B (2)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100371062B1 (ko) *	1992-11-27	2003-04-21	에프.에이치.포울딩 앤드 컴퍼니 리미티드	안정성이향상된주사가능한택솔조성물및이를제형화하는방법
CA2149150C (en)	1992-11-27	2000-08-01	David R. Carver	Injectable taxol composition with improved stability
US5973160A (en)	1992-12-23	1999-10-26	Poss; Michael A.	Methods for the preparation of novel sidechain-bearing taxanes
GB9705903D0 (en)	1997-03-21	1997-05-07	Elliott Gillian D	VP22 Proteins and uses thereof
JP2004525860A (ja)	2000-09-22	2004-08-26	ブリストル−マイヤーズスクイブカンパニー	併用化学療法剤の毒性を低下させる方法
JP2004536026A (ja)	2000-11-28	2004-12-02	トランスフォームファーマシューティカルズ，インコーポレーティッド．	パクリタキセル、その誘導体、および薬剤として許容される塩を含む医薬品製剤
AU2017324947A1 (en) *	2016-09-06	2019-03-28	Mayo Foundation For Medical Education And Research	Paclitaxel-albumin-binding agent compositions and methods for using and making the same

1991
- 1991-08-16 TW TW080106545A patent/TW223634B/zh active
1992
- 1992-02-27 DE DE69210078T patent/DE69210078D1/de not_active Expired - Lifetime
- 1992-02-27 AT AT92301652T patent/ATE137229T1/de not_active IP Right Cessation
- 1992-02-27 EP EP92301652A patent/EP0505047B1/en not_active Expired - Lifetime
- 1992-03-13 JP JP4054677A patent/JPH0684364B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0505047A1 (en)	1992-09-23
JPH0578342A (ja)	1993-03-30
EP0505047B1 (en)	1996-04-24
ATE137229T1 (de)	1996-05-15
DE69210078D1 (de)	1996-05-30
TW223634B (2)	1994-05-11

Publication	Publication Date	Title
US5194635A (en)	1993-03-16	Rearranged taxol compounds and method of using in testing of in vivo activity
Samaranayake et al.	1991	Modified taxols. 5. Reaction of taxol with electrophilic reagents and preparation of a rearranged taxol derivative with tubulin assembly activity
DE69325454T2 (de)	2000-01-20	Taxol-derivate
Magri et al.	1988	Modified taxols, 4. Synthesis and biological activity of taxols modified in the side chain
Huang et al.	1986	New taxanes from Taxus brevifolia, 2.
Magri et al.	1986	Modified taxols. 3. Preparation and acylation of baccatin III
DE69507702T2 (de)	1999-08-26	Semisynthetisch taxal derivate mit antitumor wirkung
JPH03501383A (ja)	1991-03-28	オリゴヌクレオチド官能化試薬及び方法
JPH0578342A (ja)	1993-03-30	転位型タキソール化合物及びそのタキソール化合物を使用するインビボ活性の試験方法
JPS6345293A (ja)	1988-02-26	シアロシルセラミド類及びその製造方法
Acena et al.	1994	A Stereodivergent Access to Naturally Occurring Aminocarba Sugars from (Phenylsulfonyl)-7-oxabicyclo [2.2. 1] heptane Derivatives. Total Synthesis of Penta-N, O-Acetyl-(.+-.)-Validamine and Its C1 and C2 Stereoisomers
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