NO328365B1 - Fremgangsmate til fremstilling av diskodermolid og analoger derav - Google Patents

Fremgangsmate til fremstilling av diskodermolid og analoger derav Download PDF

Info

Publication number: NO328365B1
Authority: NO; Norway
Prior art keywords: alkyl; formula; compound; hydroxyl protecting; protecting group
Prior art date: 2000-08-07

Application number

NO20030587A

Other languages

English (en)

Norwegian (no)

Other versions

NO20030587L (no

NO20030587D0 (no

Inventor

Jr Frederick Ray Kinder

Original Assignee

Novartis Ag

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.)

2000-08-07

Filing date

2003-02-06

Publication date

2010-02-01

2003-02-06 Application filed by Novartis Ag filed Critical Novartis Ag

2003-02-06 Publication of NO20030587L publication Critical patent/NO20030587L/no

2003-02-06 Publication of NO20030587D0 publication Critical patent/NO20030587D0/no

2010-02-01 Publication of NO328365B1 publication Critical patent/NO328365B1/no

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 3
230000008569 process Effects 0.000 title claims description 3
AADVCYNFEREWOS-UHFFFAOYSA-N (+)-DDM Natural products C=CC=CC(C)C(OC(N)=O)C(C)C(O)C(C)CC(C)=CC(C)C(O)C(C)C=CC(O)CC1OC(=O)C(C)C(O)C1C AADVCYNFEREWOS-UHFFFAOYSA-N 0.000 title description 16
AADVCYNFEREWOS-OBRABYBLSA-N Discodermolide Chemical compound C=C\C=C/[C@H](C)[C@H](OC(N)=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C/[C@H](C)[C@@H](O)[C@@H](C)\C=C/[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C AADVCYNFEREWOS-OBRABYBLSA-N 0.000 title description 16
125000000217 alkyl group Chemical group 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
-1 ketone compound Chemical class 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000003495 polar organic solvent Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
239000007983 Tris buffer Substances 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
150000000185 1,3-diols Chemical class 0.000 claims 2
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
QPBAAINZSOWFCC-SCRDCRAPSA-N (2r,3s,4r)-3-[tert-butyl(dimethyl)silyl]oxy-n-methoxy-n,2,4-trimethyl-5-oxohexanamide Chemical compound CON(C)C(=O)[C@H](C)[C@H]([C@@H](C)C(C)=O)O[Si](C)(C)C(C)(C)C QPBAAINZSOWFCC-SCRDCRAPSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229930012538 Paclitaxel Natural products 0.000 description 7
102000004243 Tubulin Human genes 0.000 description 7
108090000704 Tubulin Proteins 0.000 description 7
229960001592 paclitaxel Drugs 0.000 description 7
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 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
102000029749 Microtubule Human genes 0.000 description 6
108091022875 Microtubule Proteins 0.000 description 6
210000004688 microtubule Anatomy 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
229960005499 (+)-discodermolide Drugs 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000012267 brine Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000007273 lactonization reaction Methods 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
229910000342 sodium bisulfate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WIXDINQBKDGXJY-XQQFMLRXSA-N (2r,3s,4r)-3-[tert-butyl(dimethyl)silyl]oxy-n-methoxy-n,2,4-trimethyl-5-oxopentanamide Chemical compound CON(C)C(=O)[C@H](C)[C@H]([C@@H](C)C=O)O[Si](C)(C)C(C)(C)C WIXDINQBKDGXJY-XQQFMLRXSA-N 0.000 description 1
LMPPEHJTMYUSFC-PIGZVRMJSA-N (2r,3s,4s)-3-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-n-methoxy-n,2,4-trimethylhexanamide Chemical compound CON(C)C(=O)[C@H](C)[C@H]([C@@H](C)C(C)O)O[Si](C)(C)C(C)(C)C LMPPEHJTMYUSFC-PIGZVRMJSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
101100512786 Caenorhabditis elegans mei-2 gene Proteins 0.000 description 1
241001290275 Discodermia dissoluta Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
101100113585 Mus musculus Ccnb1ip1 gene Proteins 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
102220530780 Nicotinamide/nicotinic acid mononucleotide adenylyltransferase 2_H24A_mutation Human genes 0.000 description 1
241000243142 Porifera Species 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000005575 aldol reaction Methods 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000000712 assembly Effects 0.000 description 1
238000000429 assembly Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000036815 beta tubulin Diseases 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000000349 chromosome Anatomy 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003436 cytoskeletal effect Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000003463 hyperproliferative effect Effects 0.000 description 1
230000016507 interphase Effects 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
230000008880 microtubule cytoskeleton organization Effects 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
230000000394 mitotic effect Effects 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229930001119 polyketide Natural products 0.000 description 1
150000003881 polyketide derivatives Chemical class 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000004904 shortening Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
230000001629 suppression Effects 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1

Classifications

- 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
- C07C271/12—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 hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- 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
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- 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
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen 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
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
- 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
- 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)
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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Steroid Compounds (AREA)
Pyrane Compounds (AREA)

NO20030587A 2000-08-07 2003-02-06 Fremgangsmate til fremstilling av diskodermolid og analoger derav NO328365B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US63375300A	2000-08-07	2000-08-07
PCT/EP2001/009068 WO2002012220A2 (en)	2000-08-07	2001-08-06	Process for preparing discodermolide and analogues thereof

Publications (3)

Publication Number	Publication Date
NO20030587L NO20030587L (no)	2003-02-06
NO20030587D0 NO20030587D0 (no)	2003-02-06
NO328365B1 true NO328365B1 (no)	2010-02-01

Family

ID=24540984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20030587A NO328365B1 (no)	2000-08-07	2003-02-06	Fremgangsmate til fremstilling av diskodermolid og analoger derav

Country Status (29)

Country	Link
EP (1)	EP1309583B1 (de)
JP (1)	JP2004505963A (de)
KR (1)	KR100796396B1 (de)
CN (1)	CN1293067C (de)
AR (1)	AR032761A1 (de)
AT (1)	ATE330948T1 (de)
AU (2)	AU2001293726B2 (de)
BR (1)	BR0112876A (de)
CA (1)	CA2416769C (de)
CY (1)	CY1105338T1 (de)
CZ (1)	CZ300855B6 (de)
DE (1)	DE60120991T2 (de)
DK (1)	DK1309583T3 (de)
EC (1)	ECSP034459A (de)
ES (1)	ES2266266T3 (de)
HU (1)	HUP0300742A3 (de)
IL (2)	IL154109A0 (de)
MX (1)	MXPA03001192A (de)
MY (1)	MY127609A (de)
NO (1)	NO328365B1 (de)
NZ (1)	NZ523999A (de)
PE (1)	PE20020263A1 (de)
PL (1)	PL358839A1 (de)
PT (1)	PT1309583E (de)
RU (1)	RU2283309C2 (de)
SK (1)	SK1562003A3 (de)
TW (1)	TWI251591B (de)
WO (1)	WO2002012220A2 (de)
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WO2004009574A1 (en) *	2002-07-22	2004-01-29	Novartis Ag	Synthesis of discodermolide
AU2003263090A1 (en)	2002-09-06	2004-03-29	University Of Pittsburgh	Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof
US7321046B2 (en)	2002-09-06	2008-01-22	University Of Pittsburgh	Analogs of dictyostatin, intermediates therefor and methods of synthesis thereof
US7214708B2 (en)	2004-11-18	2007-05-08	Kosan Biosciences Incorporated	Synthetic discodermolide analogs

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US4939168A (en) *	1989-08-11	1990-07-03	Harbor Branch Oceanographics Institution, Inc.	Discodermolide compounds, compositions containing same and methods of preparation and use
IL108432A (en) *	1993-01-29	1997-09-30	Sankyo Co	DERIVATIVES OF 3, 5-DIHYDROXY-7- £1, 2, 6, 7, 8, 8a-HEXAHYDRO-2- METHYL-8- (SUBSTITUTED ALKANOYLOXY)-1-NAPHTHYL\| HEPTANOIC ACID AND THEIR LACTONES, THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
GB9315802D0 (en) *	1993-07-30	1993-09-15	Roussel Lab Ltd	Chemical compounds
US6096904A (en) *	1996-12-03	2000-08-01	The Trustees Of The University Of Pennsylvania	Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives
US5789605A (en) *	1996-12-03	1998-08-04	Trustees Of The University Of Pennsylvania	Synthetic techniques and intermediates for polyhydroxy, dienyl lactones and mimics thereof
AU7267298A (en) *	1997-04-30	1998-11-24	Regents Of The University Of California, The	Synthesis of discodermolide and analogs
GB0101599D0 (en) *	2001-01-22	2001-03-07	Novartis Ag	Organic compounds

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Also Published As

Publication number	Publication date
CY1105338T1 (el)	2010-03-03
PT1309583E (pt)	2006-10-31
PL358839A1 (en)	2004-08-23
IL154109A0 (en)	2003-07-31
DK1309583T3 (da)	2006-10-16
ATE330948T1 (de)	2006-07-15
WO2002012220A2 (en)	2002-02-14
ECSP034459A (es)	2003-03-10
NO20030587L (no)	2003-02-06
ES2266266T3 (es)	2007-03-01
ZA200300590B (en)	2004-04-01
NO20030587D0 (no)	2003-02-06
CA2416769A1 (en)	2002-02-14
KR20030040385A (ko)	2003-05-22
CZ300855B6 (cs)	2009-08-26
KR100796396B1 (ko)	2008-01-21
HK1055962A1 (en)	2004-01-30
JP2004505963A (ja)	2004-02-26
CZ2003330A3 (cs)	2003-05-14
IL154109A (en)	2008-11-03
MY127609A (en)	2006-12-29
CN1293067C (zh)	2007-01-03
DE60120991D1 (de)	2006-08-03
HUP0300742A3 (en)	2005-11-28
AU2001293726B2 (en)	2005-04-14
WO2002012220A3 (en)	2002-06-13
DE60120991T2 (de)	2007-06-21
HUP0300742A2 (hu)	2003-09-29
RU2283309C2 (ru)	2006-09-10
AR032761A1 (es)	2003-11-26
SK1562003A3 (en)	2003-08-05
MXPA03001192A (es)	2003-06-30
NZ523999A (en)	2004-08-27
TWI251591B (en)	2006-03-21
PE20020263A1 (es)	2002-05-14
CN1446208A (zh)	2003-10-01
AU9372601A (en)	2002-02-18
CA2416769C (en)	2009-02-17
BR0112876A (pt)	2003-07-01
EP1309583B1 (de)	2006-06-21
EP1309583A2 (de)	2003-05-14

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Publication	Publication Date	Title
HU207288B (en)	1993-03-29	Process for enenthioselective producing phenyl-isoserine derivatives
GB2280677A (en)	1995-02-08	Total synthesis of discodermolide
EP0167154B1 (de)	1990-01-03	Verfahren zur Herstellung von 4-Acetoxy-3-hydroxyethylazetizin-2-on Derivaten
EP1309583B1 (de)	2006-06-21	Verfahren zu herstellung von discodermoliden und ähnlichen verbindungen
US6506910B1 (en)	2003-01-14	Process for preparing discodermolide and analogues thereof
AU2001293726A1 (en)	2002-05-16	Process for preparing discodermolide and analogues thereof
US4940797A (en)	1990-07-10	Process for synthesis of FK-506 C10-C18 intermediates
KR101076680B1 (ko)	2011-10-26	(6ｒ)-3-헥실-4-히드록시-6-운데실-5,6-다이히드로피란-2-온의 제조방법 및 이에 사용되는 중간체
HK1055962B (en)	2007-01-19	Process for preparing discodermolide and analogues thereof
Wang et al.	2008	A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones
KR100503022B1 (ko)	2005-07-25	심바스타틴의 신규 제조방법 및 그에 사용되는 합성 중간체
JPS6244A (ja)	1987-01-06	２−ハロ−２−シクロペンテノン誘導体及びその製法
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US9683010B2 (en)	2017-06-20	Process for the production of 21-methoxy-11-beta-phenyl-19-nor-pregna-4,9-diene-3,20-dione derivatives
JP2718546B2 (ja)	1998-02-25	シクロペンテノン誘導体の立体選択的製造法
JPH06793B2 (ja)	1994-01-05	Ｅ―２―メチル―α，β―不飽和アルデヒドの合成方法
KR20030040858A (ko)	2003-05-23	심바스타틴의 신규 제조방법
FR2745809A1 (fr)	1997-09-12	Procede de preparation d'isoserines utiles dans la synthese de taxoides therapeutiquement actifs
JPS60197662A (ja)	1985-10-07	カ−バメ−ト及びその製法