FI113046B - Menetelmä substituoitujen isoseriiniesterien valmistamiseksi käyttäen metallialkoksideja ja beta-laktaameja - Google Patents

Menetelmä substituoitujen isoseriiniesterien valmistamiseksi käyttäen metallialkoksideja ja beta-laktaameja Download PDF

Info

Publication number: FI113046B
Authority: FI; Finland
Prior art keywords: solution; thf; protecting group; give; process according
Prior art date: 1991-09-23

Application number

FI941325A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI941325A0 (fi

FI941325L (fi

Inventor

Robert A Holton

Original Assignee

Univ Florida State

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.)

1991-09-23

Filing date

1994-03-22

Publication date

2004-02-27

1994-03-22 Application filed by Univ Florida State filed Critical Univ Florida State

1994-03-22 Publication of FI941325A0 publication Critical patent/FI941325A0/fi

1994-05-04 Publication of FI941325L publication Critical patent/FI941325L/fi

2004-02-27 Application granted granted Critical

2004-02-27 Publication of FI113046B publication Critical patent/FI113046B/fi

Links

229910052751 metal Inorganic materials 0.000 title claims abstract description 50
239000002184 metal Substances 0.000 title claims abstract description 50
150000004703 alkoxides Chemical class 0.000 title claims abstract description 36
150000003952 β-lactams Chemical class 0.000 title claims abstract description 28
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 37
-1 isoserine ester Chemical class 0.000 claims abstract description 94
125000003118 aryl group Chemical group 0.000 claims abstract description 79
238000000034 method Methods 0.000 claims abstract description 56
125000000217 alkyl group Chemical group 0.000 claims abstract description 33
230000008569 process Effects 0.000 claims abstract description 32
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 abstract description 27
125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
125000000304 alkynyl group Chemical group 0.000 claims abstract description 22
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
229940123237 Taxane Drugs 0.000 claims abstract description 13
125000002252 acyl group Chemical group 0.000 claims abstract description 10
125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 6
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 99
229910052739 hydrogen Inorganic materials 0.000 claims description 42
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 40
239000001257 hydrogen Substances 0.000 claims description 40
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 12
229910052744 lithium Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
229910052700 potassium Inorganic materials 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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125000002837 carbocyclic group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 2
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229910052719 titanium Inorganic materials 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 5
101100215147 Caenorhabditis elegans aco-1 gene Proteins 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
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125000004122 cyclic group Chemical group 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 249
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 228
239000000243 solution Substances 0.000 description 210
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 114
229930012538 Paclitaxel Natural products 0.000 description 85
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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 81
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 65
229920006395 saturated elastomer Polymers 0.000 description 58
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 30
239000012044 organic layer Substances 0.000 description 30
238000003818 flash chromatography Methods 0.000 description 28
239000000463 material Substances 0.000 description 26
229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
235000017557 sodium bicarbonate Nutrition 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 23
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
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125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
238000001914 filtration Methods 0.000 description 16
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 15
101100108327 Escherichia coli (strain K12) melA gene Proteins 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 15
125000004423 acyloxy group Chemical group 0.000 description 14
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 11
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 9
125000004104 aryloxy group Chemical group 0.000 description 9
239000002243 precursor Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
229940063683 taxotere Drugs 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
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229910052760 oxygen Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
SVGIEMHCAPRHEZ-SJORKVTESA-N (3s,4r)-1-benzoyl-3-(2-methoxypropan-2-yloxy)-4-phenylazetidin-2-one Chemical compound N1([C@@H]([C@@H](C1=O)OC(C)(C)OC)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 SVGIEMHCAPRHEZ-SJORKVTESA-N 0.000 description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
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239000001301 oxygen Substances 0.000 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 description 4
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 3
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239000007864 aqueous solution Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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230000000694 effects Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
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125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
239000011591 potassium Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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230000000259 anti-tumor effect Effects 0.000 description 2
230000008901 benefit Effects 0.000 description 2
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150000004649 carbonic acid derivatives Chemical class 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
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239000011777 magnesium Substances 0.000 description 2
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238000012986 modification Methods 0.000 description 2
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VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
SKJSIVQEPKBFTJ-HUWILPJBSA-N taxusin Chemical compound C1[C@@H](C2(C)C)C[C@H](OC(C)=O)C(C)=C2[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@]2(C)CC[C@H](OC(=O)C)C(=C)[C@@H]12 SKJSIVQEPKBFTJ-HUWILPJBSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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239000010936 titanium Substances 0.000 description 2
150000003624 transition metals Chemical group 0.000 description 2
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239000011701 zinc Substances 0.000 description 2
DTGKSKDOIYIVQL-QXFUBDJGSA-N (-)-borneol Chemical compound C1C[C@]2(C)[C@H](O)C[C@H]1C2(C)C DTGKSKDOIYIVQL-QXFUBDJGSA-N 0.000 description 1
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230000009471 action Effects 0.000 description 1
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230000004071 biological effect Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
ASLILGPXYVHSJM-UHFFFAOYSA-N butyl n-chlorocarbamate Chemical compound CCCCOC(=O)NCl ASLILGPXYVHSJM-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
229960004873 levomenthol Drugs 0.000 description 1
PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical class [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
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125000001979 organolithium group Chemical group 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
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239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
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125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
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229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen 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
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen 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 one oxygen atom directly attached in position 2, e.g. beta-lactams
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/22—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from lactams, cyclic ketones or cyclic oximes, e.g. by reactions involving Beckmann rearrangement
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
- 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

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Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Cephalosporin Compounds (AREA)
Glass Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Cosmetics (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

FI941325A 1991-09-23 1994-03-22 Menetelmä substituoitujen isoseriiniesterien valmistamiseksi käyttäen metallialkoksideja ja beta-laktaameja FI113046B (fi)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
US76380591A	1991-09-23	1991-09-23
US76380591		1991-09-23
US86295592A	1992-04-03	1992-04-03
US86295592		1992-04-03
US86384992A	1992-04-06	1992-04-06
US86384992		1992-04-06
PCT/US1992/007990 WO1993006079A1 (en)	1991-09-23	1992-09-22	PREPARATION OF SUBSTITUTED ISOSERINE ESTERS USING METAL ALKOXIDES AND β-LACTAMS
US9207990		1992-09-22

Publications (3)

Publication Number	Publication Date
FI941325A0 FI941325A0 (fi)	1994-03-22
FI941325L FI941325L (fi)	1994-05-04
FI113046B true FI113046B (fi)	2004-02-27

Family

ID=29716161

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI941325A FI113046B (fi)	1991-09-23	1994-03-22	Menetelmä substituoitujen isoseriiniesterien valmistamiseksi käyttäen metallialkoksideja ja beta-laktaameja

Country Status (16)

Country	Link
EP (3)	EP1193252B1 (ja)
JP (2)	JP3469237B2 (ja)
KR (1)	KR100252493B1 (ja)
AT (3)	ATE258171T1 (ja)
CA (3)	CA2254273C (ja)
CZ (2)	CZ290590B6 (ja)
DE (3)	DE69233672T2 (ja)
DK (3)	DK1193252T3 (ja)
ES (3)	ES2277964T3 (ja)
FI (1)	FI113046B (ja)
GR (1)	GR3030329T3 (ja)
HU (1)	HU226369B1 (ja)
NO (1)	NO306209B1 (ja)
RU (1)	RU2128654C1 (ja)
SG (2)	SG97130A1 (ja)
WO (1)	WO1993006079A1 (ja)

Families Citing this family (32)

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US6005138A (en)	1991-09-23	1999-12-21	Florida State University	Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US6521660B2 (en)	1991-09-23	2003-02-18	Florida State University	3′-alkyl substituted taxanes and pharmaceutical compositions containing them
US7074945B2 (en)	1991-09-23	2006-07-11	Florida State University	Metal alkoxide taxane derivatives
US5284864A (en)	1991-09-23	1994-02-08	Florida State University	Butenyl substituted taxanes 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
US5430160A (en)	1991-09-23	1995-07-04	Florida State University	Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides
US5294637A (en) *	1992-07-01	1994-03-15	Bristol-Myers Squibb Company	Fluoro taxols
US5380751A (en) *	1992-12-04	1995-01-10	Bristol-Myers Squibb Company	6,7-modified paclitaxels
PL186176B1 (pl) *	1992-12-23	2003-11-28	Bristol Myers Squibb Co	Sposób wytwarzania zawierającego oksazolinowy łańcuch boczny taksanu, zwierający łańcuch boczny taksan, oksazolinowy związek, sposób wytwarzania związku oksazolinowego, sposób wytwarzania zawierającego łańcuch boczny taksanu, pochodna taksanu, prekursor paklitakselu, sposób wytwarzania bakatyny, sposób wytwarzania paklitakselu i pochodna bakatyny
US5646176A (en)	1992-12-24	1997-07-08	Bristol-Myers Squibb Company	Phosphonooxymethyl ethers of taxane derivatives
ZA94128B (en) *	1993-02-01	1994-08-19	Univ New York State Res Found	Process for the preparation of taxane derivatives and betalactam intermediates therefor
TW467896B (en)	1993-03-19	2001-12-11	Bristol Myers Squibb Co	Novel β-lactams, methods for the preparation of taxanes and sidechain-bearing taxanes
CA2158862C (en) *	1993-03-22	2006-10-10	Robert A. Holton	Taxanes having alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing same
US5677470A (en) *	1994-06-28	1997-10-14	Tanabe Seiyaku Co., Ltd.	Baccatin derivatives and processes for preparing the same
US6201140B1 (en)	1994-07-28	2001-03-13	Bristol-Myers Squibb Company	7-0-ethers of taxane derivatives
CA2162759A1 (en) *	1994-11-17	1996-05-18	Kenji Tsujihara	Baccatin derivatives and processes for preparing the same
DE19509697A1 (de) *	1995-03-08	1996-09-12	Schering Ag	Neue Borneole, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung
US6107332A (en)	1995-09-12	2000-08-22	The Liposome Company, Inc.	Hydrolysis-promoting hydrophobic taxane derivatives
US6051600A (en) *	1995-09-12	2000-04-18	Mayhew; Eric	Liposomal hydrolysis-promoting hydrophobic taxane derivatives
NZ332475A (en) *	1996-05-08	2000-05-26	Upjohn Co	silylated baccatin derivatives, 3-(substituted amino)-3-phenyl-(2R,3S)-isoserinate derivatives, the oxazolidine ester thereof and other immediates used to prepare baccatin derivatives
WO2000073293A1 (en)	1999-05-28	2000-12-07	Bristol-Myers Squibb Co.	Semi-synthesis of paclitaxel using dialkyldichlorosilanes
US6649632B2 (en)	2000-02-02	2003-11-18	Fsu Research Foundation, Inc.	C10 ester substituted taxanes
EP1347981B1 (en)	2000-12-01	2008-05-07	Biogen Idec MA Inc.	Condensed purine derivatives as a 1 adenosine receptor antagonists
MXPA04005038A (es)	2001-11-30	2004-08-11	Bristol Myers Squibb Co	Solvatos de paclitaxel.
PL194032B1 (pl) *	2002-12-19	2007-04-30	Agropharm Sa	Sposób wytwarzania półproduktów użytecznych w syntezie paklitakselu
US6956123B2 (en) *	2003-03-17	2005-10-18	Natural Pharmaccuticals, Inc.	Purification of taxanes and taxane mixtures using polyethyleneimine-bonded resins
US8703982B2 (en)	2003-03-17	2014-04-22	Phyton Holdings Llc	Purification of taxanes
HN2005000054A (es)	2004-02-13	2009-02-18	Florida State University Foundation Inc	Taxanos sustituidos con esteres de ciclopentilo en c10
WO2006116532A2 (en)	2005-04-28	2006-11-02	University Of Massachusetts Lowell	Synthesis of oligo/poly(catechins) and methods of use
JP2011517455A (ja)	2008-03-31	2011-06-09	フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド	Ｃ（１０）エチルエステルおよびｃ（１０）シクロプロピルエステル置換タキサン
PL388144A1 (pl)	2009-05-29	2010-12-06	Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością	Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie
AU2015241198A1 (en)	2014-04-03	2016-11-17	Invictus Oncology Pvt. Ltd.	Supramolecular combinatorial therapeutics

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5175315A (en) *	1989-05-31	1992-12-29	Florida State University	Method for preparation of taxol using β-lactam
US5136060A (en) *	1989-11-14	1992-08-04	Florida State University	Method for preparation of taxol using an oxazinone
MX9102128A (es) *	1990-11-23	1992-07-08	Rhone Poulenc Rorer Sa	Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene

1992
- 1992-09-22 EP EP02000688A patent/EP1193252B1/en not_active Expired - Lifetime
- 1992-09-22 ES ES02000688T patent/ES2277964T3/es not_active Expired - Lifetime
- 1992-09-22 EP EP98114788A patent/EP0884314B1/en not_active Expired - Lifetime
- 1992-09-22 DK DK02000688T patent/DK1193252T3/da active
- 1992-09-22 SG SG9904181A patent/SG97130A1/en unknown
- 1992-09-22 DK DK98114788T patent/DK0884314T3/da active
- 1992-09-22 HU HU9400830A patent/HU226369B1/hu not_active IP Right Cessation
- 1992-09-22 DE DE69233672T patent/DE69233672T2/de not_active Expired - Lifetime
- 1992-09-22 JP JP50629993A patent/JP3469237B2/ja not_active Expired - Fee Related
- 1992-09-22 CA CA002254273A patent/CA2254273C/en not_active Expired - Fee Related
- 1992-09-22 EP EP92921316A patent/EP0605637B1/en not_active Expired - Lifetime
- 1992-09-22 CA CA002418125A patent/CA2418125C/en not_active Expired - Fee Related
- 1992-09-22 WO PCT/US1992/007990 patent/WO1993006079A1/en active IP Right Grant
- 1992-09-22 AT AT98114788T patent/ATE258171T1/de not_active IP Right Cessation
- 1992-09-22 CA CA002098478A patent/CA2098478C/en not_active Expired - Fee Related
- 1992-09-22 DE DE69228756T patent/DE69228756T2/de not_active Expired - Lifetime
- 1992-09-22 SG SG1996005203A patent/SG52496A1/en unknown
- 1992-09-22 CZ CZ327096A patent/CZ290590B6/cs not_active IP Right Cessation
- 1992-09-22 AT AT02000688T patent/ATE349424T1/de not_active IP Right Cessation
- 1992-09-22 ES ES92921316T patent/ES2132129T3/es not_active Expired - Lifetime
- 1992-09-22 AT AT92921316T patent/ATE178060T1/de not_active IP Right Cessation
- 1992-09-22 DK DK92921316T patent/DK0605637T3/da active
- 1992-09-22 KR KR1019940700949A patent/KR100252493B1/ko not_active Expired - Fee Related
- 1992-09-22 DE DE69233292T patent/DE69233292T2/de not_active Expired - Lifetime
- 1992-09-22 ES ES98114788T patent/ES2214665T3/es not_active Expired - Lifetime
- 1992-09-22 RU RU94044324A patent/RU2128654C1/ru not_active IP Right Cessation
- 1992-09-22 CZ CZ1994660A patent/CZ287417B6/cs not_active IP Right Cessation
1994
- 1994-03-22 NO NO941022A patent/NO306209B1/no not_active IP Right Cessation
- 1994-03-22 FI FI941325A patent/FI113046B/fi active
1999
- 1999-05-27 GR GR990401416T patent/GR3030329T3/el unknown
2003
- 2003-05-06 JP JP2003128200A patent/JP2004043439A/ja active Pending

Also Published As

Publication number	Publication date
EP0605637A1 (en)	1994-07-13
ES2277964T3 (es)	2007-08-01
EP1193252A3 (en)	2003-11-05
DE69233672D1 (de)	2007-02-08
NO941022D0 (no)	1994-03-22
JP3469237B2 (ja)	2003-11-25
CA2418125C (en)	2007-12-04
EP0605637B1 (en)	1999-03-24
EP0605637A4 (en)	1994-08-24
AU2689092A (en)	1993-04-27
DE69233292D1 (de)	2004-02-26
CA2098478A1 (en)	1993-03-24
RU2128654C1 (ru)	1999-04-10
NO941022L (no)	1994-05-20
SG97130A1 (en)	2003-07-18
DE69233292T2 (de)	2004-06-09
ES2132129T3 (es)	1999-08-16
CA2418125A1 (en)	1993-03-24
AU647971B2 (en)	1994-03-31
DE69228756D1 (de)	1999-04-29
JPH07502983A (ja)	1995-03-30
KR100252493B1 (ko)	2000-05-01
DE69228756T2 (de)	1999-10-07
ES2214665T3 (es)	2004-09-16
DE69233672T2 (de)	2007-10-18
WO1993006079A1 (en)	1993-04-01
GR3030329T3 (en)	1999-09-30
CA2254273C (en)	2003-03-25
ATE258171T1 (de)	2004-02-15
CZ287417B6 (cs)	2000-11-15
HU226369B1 (en)	2008-09-29
CZ290590B6 (en)	2002-08-14
EP1193252A2 (en)	2002-04-03
EP0884314A3 (en)	2002-05-02
HU9400830D0 (en)	1994-06-28
SG52496A1 (en)	1998-09-28
DK1193252T3 (da)	2007-04-30
EP0884314A2 (en)	1998-12-16
EP0884314B1 (en)	2004-01-21
DK0605637T3 (da)	1999-10-11
ATE349424T1 (de)	2007-01-15
CA2254273A1 (en)	1993-03-24
DK0884314T3 (da)	2004-05-24
JP2004043439A (ja)	2004-02-12
FI941325A0 (fi)	1994-03-22
HUT71795A (en)	1996-02-28
EP1193252B1 (en)	2006-12-27
CZ66094A3 (en)	1994-12-15
CA2098478C (en)	1999-09-14
NO306209B1 (no)	1999-10-04
ATE178060T1 (de)	1999-04-15
FI941325L (fi)	1994-05-04

Publication	Publication Date	Title
FI113046B (fi)	2004-02-27	Menetelmä substituoitujen isoseriiniesterien valmistamiseksi käyttäen metallialkoksideja ja beta-laktaameja
US6683196B2 (en)	2004-01-27	Process for the preparation of metal alkoxides
FI109796B (fi)	2002-10-15	Metallialkoksidit
US6653490B2 (en)	2003-11-25	Process for the preparation of ammonium alkoxides
AU647971C (en)	1995-01-12	Preparation of isoserine ester and taxane
US7074945B2 (en)	2006-07-11	Metal alkoxide taxane derivatives
IL103191A (en)	2001-07-24	Semisynthesis of the history of Texan using metallic and beta alkoxides, and their intermediates