NO325664B1 - Fremgangsmate for fremstilling av derivater av taxoidklassen - Google Patents
Fremgangsmate for fremstilling av derivater av taxoidklassen Download PDFInfo
- Publication number
- NO325664B1 NO325664B1 NO20002443A NO20002443A NO325664B1 NO 325664 B1 NO325664 B1 NO 325664B1 NO 20002443 A NO20002443 A NO 20002443A NO 20002443 A NO20002443 A NO 20002443A NO 325664 B1 NO325664 B1 NO 325664B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- residues
- phenyl
- optionally substituted
- alkali metal
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 56
- -1 C3.6-cycloalkyl Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 19
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910001923 silver oxide Inorganic materials 0.000 claims description 12
- 239000002168 alkylating agent Substances 0.000 claims description 11
- 229940100198 alkylating agent Drugs 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229930190007 Baccatin Natural products 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000005239 aroylamino group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001351 alkyl iodides Chemical class 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 125000005527 methyl sulfate group Chemical group 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 27
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 22
- YWLXLRUDGLRYDR-SKXCCXORSA-N 10-dab iii Chemical compound O([C@H]1C2[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-SKXCCXORSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000010606 normalization Methods 0.000 description 12
- YWLXLRUDGLRYDR-UHFFFAOYSA-N 10-deacetylbaccatin Chemical compound CC(=O)OC12COC1CC(O)C(C(C(O)C1=C(C)C(O)CC3(O)C1(C)C)=O)(C)C2C3OC(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 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
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 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 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- MSVWUXLRSKRKFZ-IPMKNSEASA-N (2r,4s,5r)-2-(4-methoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1[C@@H]1N(C(=O)OC(C)(C)C)[C@@H](C=2C=CC=CC=2)[C@H](C(O)=O)O1 MSVWUXLRSKRKFZ-IPMKNSEASA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- UUAKOKFSMXRGJP-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methoxymethoxymethoxymethyl]benzene Chemical compound C1=CC(OC)=CC=C1COCOCOCC1=CC=C(OC)C=C1 UUAKOKFSMXRGJP-UHFFFAOYSA-N 0.000 description 1
- CRAJLXHBNCCDPK-UHFFFAOYSA-N 2,2,2-trichloroethyl hydrogen carbonate Chemical class OC(=O)OCC(Cl)(Cl)Cl CRAJLXHBNCCDPK-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical group O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- LZAYVHYCWHGWSQ-UHFFFAOYSA-N 2-methoxy-2-(2-methoxy-1-nitropropan-2-yl)oxy-1-nitropropane Chemical group [O-][N+](=O)CC(C)(OC)OC(C)(C[N+]([O-])=O)OC LZAYVHYCWHGWSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- ANPYLYUCGAFKNQ-UHFFFAOYSA-N ethoxymethoxymethoxyethane Chemical compound CCOCOCOCC ANPYLYUCGAFKNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HYHLXSWZHRFFJZ-UHFFFAOYSA-N iodomethane;oxolane Chemical compound IC.C1CCOC1 HYHLXSWZHRFFJZ-UHFFFAOYSA-N 0.000 description 1
- DCMYPPXQMFLRHI-UHFFFAOYSA-N iodomethane;toluene Chemical compound IC.CC1=CC=CC=C1 DCMYPPXQMFLRHI-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- TYZYRCHEVXXLSJ-UHFFFAOYSA-N phenylmethoxymethoxymethoxymethylbenzene Chemical compound C=1C=CC=CC=1COCOCOCC1=CC=CC=C1 TYZYRCHEVXXLSJ-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- QWEJGTIVESCYNM-UHFFFAOYSA-N trimethyl-[2-(2-trimethylsilylethoxymethoxymethoxy)ethyl]silane Chemical group C[Si](C)(C)CCOCOCOCC[Si](C)(C)C QWEJGTIVESCYNM-UHFFFAOYSA-N 0.000 description 1
- QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9714442A FR2771092B1 (fr) | 1997-11-18 | 1997-11-18 | Procede de preparation de derives de la classe des taxoides |
| PCT/FR1998/002432 WO1999025704A1 (fr) | 1997-11-18 | 1998-11-16 | Procede de preparation de derives de la classe des taxoides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20002443L NO20002443L (no) | 2000-05-11 |
| NO20002443D0 NO20002443D0 (no) | 2000-05-11 |
| NO325664B1 true NO325664B1 (no) | 2008-07-07 |
Family
ID=9513490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20002443A NO325664B1 (no) | 1997-11-18 | 2000-05-11 | Fremgangsmate for fremstilling av derivater av taxoidklassen |
Country Status (44)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6372780B2 (en) | 1995-03-27 | 2002-04-16 | Aventis Pharma S.A. | Methods of treating cell lines expressing multidrug resistance P-glycoprotein |
| MA23823A1 (fr) | 1995-03-27 | 1996-10-01 | Aventis Pharma Sa | Nouveaux taxoides, leur preparation et les compositions qui les contiennent |
| US6346543B1 (en) * | 1998-08-17 | 2002-02-12 | Aventis Pharma S.A. | Use of a taxoid to treat abnormal cell proliferation in the brain |
| US6403634B1 (en) | 1999-01-13 | 2002-06-11 | Aventis Pharma S.A. | Use of taxoid derivatives |
| FR2859996B1 (fr) | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| FR2926551A1 (fr) * | 2008-01-17 | 2009-07-24 | Aventis Pharma Sa | Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation |
| EP2331140B1 (en) | 2008-08-11 | 2018-07-04 | Nektar Therapeutics | Multi-arm polymeric alkanoate conjugates |
| PE20121429A1 (es) | 2009-10-29 | 2012-11-06 | Aventis Pharma Sa | Nuevo uso antitumoral de cabazitaxel |
| US8791279B2 (en) | 2010-12-13 | 2014-07-29 | Yung Shin Pharm. Ind. Co., Ltd. | Process for preparing taxoids from baccatin derivatives using lewis acid catalyst |
| US20130331443A1 (en) | 2010-12-22 | 2013-12-12 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
| WO2012088433A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Deuterated and/or fluorinated taxane derivatives |
| WO2012088445A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
| EA023950B1 (ru) | 2011-04-12 | 2016-07-29 | Тева Фармасьютикалз Интернэшнл Гмбх | Твердофазные формы кабазитаксела и способы их получения |
| TWI526437B (zh) * | 2011-09-09 | 2016-03-21 | 台灣神隆股份有限公司 | 卡巴他賽之結晶型 |
| CN103012329A (zh) * | 2011-09-23 | 2013-04-03 | 复旦大学 | 一种制备紫杉醇类抗癌药Cabazitaxel XRP6258的方法 |
| CN103012330A (zh) * | 2011-09-23 | 2013-04-03 | 复旦大学 | 一种紫杉醇类抗癌药xrp6258的制备方法 |
| EP2760848B1 (en) | 2011-09-26 | 2018-11-28 | Fresenius Kabi Oncology Limited | Processes for the preparation of cabazitaxel involving c(7)-oh and c(13)-oh silylation or just c(7)-oh silylation |
| CN102408397B (zh) * | 2011-10-19 | 2014-08-20 | 上海贝美医药科技有限公司 | 紫杉烷类衍生物及其制备方法 |
| CN102516281B (zh) * | 2011-10-20 | 2015-02-04 | 江苏红豆杉生物科技股份有限公司 | 一种10-脱乙酰基巴卡丁iii及其衍生物甲氧基化的方法 |
| CN103906747A (zh) | 2011-10-31 | 2014-07-02 | 台湾神隆股份有限公司 | 卡巴他赛及其中间体的制备方法 |
| CN103159704B (zh) * | 2011-12-12 | 2015-06-10 | 上海佰霖国际贸易有限公司 | 卡巴他赛中间体及卡巴他赛中间体的制备方法 |
| CN103159705B (zh) * | 2011-12-12 | 2015-05-27 | 福建南方制药股份有限公司 | 卡巴他赛中间体的制备方法 |
| US9403785B2 (en) | 2012-01-03 | 2016-08-02 | Shilpa Medicare Limited | Process for preparing amorphous cabazitaxel |
| CN102786502B (zh) * | 2012-08-21 | 2014-05-14 | 江苏红豆杉生物科技有限公司 | 一种紫杉烷药物7,10-甲氧基多西他赛的合成方法 |
| EP2917192B1 (en) | 2012-11-09 | 2019-03-20 | Intas Pharmaceuticals Limited | Process for the preparation of cabazitaxel and its intermediates |
| KR101407353B1 (ko) * | 2012-12-04 | 2014-06-17 | 주식회사 삼양바이오팜 | 10-디아세틸바카틴 iii으로부터 카바지탁셀을 고수율로 제조하는 새로운 방법 및 이를 위한 신규 중간체 |
| EP2743264A1 (en) | 2012-12-13 | 2014-06-18 | INDENA S.p.A. | New crystalline form of cabazitaxel, process for the preparation and pharmaceutical compositions thereof |
| CN103012331A (zh) * | 2012-12-28 | 2013-04-03 | 北京科莱博医药开发有限责任公司 | 卡巴他赛及其中间体的制备方法 |
| EP3008047B1 (en) * | 2013-06-14 | 2019-01-09 | Hetero Research Foundation | Process for cabazitaxel |
| CN104418826B (zh) * | 2013-08-28 | 2017-06-30 | 江苏恒瑞医药股份有限公司 | 7β,10β‑二甲氧基‑10‑去乙酰基浆果赤霉素III的制备方法 |
| CN103450117A (zh) * | 2013-09-18 | 2013-12-18 | 江苏红豆杉药业有限公司 | 一种7,10-二甲氧基紫杉烷化合物的制备方法 |
| KR101490738B1 (ko) | 2013-10-15 | 2015-02-11 | (주)한국해양기상기술 | 플랑크톤 검사장치 |
| EP2865674A1 (en) | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | Crystalline solvate forms of Cabazitaxel |
| EP2865675A1 (en) | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | A crystalline anhydrous form of Cabazitaxel, process for the preparation and pharmaceutical compositions thereof |
| CN105121419B (zh) * | 2013-12-24 | 2016-08-03 | 于跃 | Cabazitaxel类抗多药耐药紫杉烷类抗肿瘤化合物及其制备方法 |
| CN104817522A (zh) * | 2015-04-01 | 2015-08-05 | 江苏红豆杉药业有限公司 | 一种7,10-二甲氧基-10DabⅢ的合成方法 |
| WO2020249507A1 (en) | 2019-06-11 | 2020-12-17 | Indena S.P.A. | Anhydrous crystalline form of cabazitaxel, a process for its preparation and pharmaceutical compositions containing it |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927118A (en) * | 1973-12-21 | 1975-12-16 | Crown Zellerbach Corp | Process for monoetherification of polyhydric benzenes |
| EP0304244A3 (en) * | 1987-08-18 | 1990-01-10 | Takeda Chemical Industries, Ltd. | Propanediol derivatives, their production and use |
| US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| FR2696459B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
| 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 |
| GB9405400D0 (en) * | 1994-03-18 | 1994-05-04 | Erba Carlo Spa | Taxane derivatives |
| CA2188452C (en) * | 1994-04-28 | 2000-12-05 | Sumanas Rakhit | Guanidino-substituted compounds |
| IT1274250B (it) * | 1995-02-21 | 1997-07-15 | Himont Inc | Dieteri utilizzabili nella preparazione di catalizzatori ziegler-natta |
| MA23823A1 (fr) * | 1995-03-27 | 1996-10-01 | Aventis Pharma Sa | Nouveaux taxoides, leur preparation et les compositions qui les contiennent |
| US5688977A (en) * | 1996-02-29 | 1997-11-18 | Napro Biotherapeutics, Inc. | Method for docetaxel synthesis |
-
1997
- 1997-11-18 FR FR9714442A patent/FR2771092B1/fr not_active Expired - Lifetime
-
1998
- 1998-11-16 PT PT98955658T patent/PT1032565E/pt unknown
- 1998-11-16 CZ CZ20001789A patent/CZ292642B6/cs not_active IP Right Cessation
- 1998-11-16 TR TR2000/01415T patent/TR200001415T2/xx unknown
- 1998-11-16 AP APAP/P/2000/001816A patent/AP1198A/en active
- 1998-11-16 EE EEP200000155A patent/EE04277B1/xx unknown
- 1998-11-16 GE GEAP19985346A patent/GEP20022822B/en unknown
- 1998-11-16 SK SK710-2000A patent/SK283932B6/sk not_active IP Right Cessation
- 1998-11-16 SI SI9830359T patent/SI1032565T1/xx unknown
- 1998-11-16 PL PL340579A patent/PL191240B1/pl unknown
- 1998-11-16 NZ NZ504125A patent/NZ504125A/xx not_active IP Right Cessation
- 1998-11-16 EP EP98955658A patent/EP1032565B1/fr not_active Expired - Lifetime
- 1998-11-16 DE DE69811530T patent/DE69811530T2/de not_active Expired - Lifetime
- 1998-11-16 WO PCT/FR1998/002432 patent/WO1999025704A1/fr not_active Application Discontinuation
- 1998-11-16 EA EA200000539A patent/EA002622B1/ru not_active IP Right Cessation
- 1998-11-16 JP JP2000521087A patent/JP4359386B2/ja not_active Expired - Fee Related
- 1998-11-16 HU HU0100519A patent/HU228188B1/hu unknown
- 1998-11-16 UA UA2000052800A patent/UA56275C2/uk unknown
- 1998-11-16 ES ES98955658T patent/ES2192795T3/es not_active Expired - Lifetime
- 1998-11-16 BR BRPI9814658A patent/BRPI9814658B8/pt not_active IP Right Cessation
- 1998-11-16 ID IDW20000902A patent/ID24620A/id unknown
- 1998-11-16 CN CNB98809181XA patent/CN100375744C/zh not_active Expired - Lifetime
- 1998-11-16 DZ DZ980263A patent/DZ2653A1/xx active
- 1998-11-16 TN TNTNSN98207A patent/TNSN98207A1/fr unknown
- 1998-11-16 IL IL13551298A patent/IL135512A/en not_active IP Right Cessation
- 1998-11-16 MA MA25349A patent/MA24817A1/fr unknown
- 1998-11-16 MX MXPA00002244A patent/MXPA00002244A/es unknown
- 1998-11-16 KR KR1020007005325A patent/KR100581656B1/ko not_active IP Right Cessation
- 1998-11-16 CA CA002304833A patent/CA2304833C/fr not_active Expired - Lifetime
- 1998-11-16 AU AU12422/99A patent/AU755376B2/en not_active Expired
- 1998-11-16 DK DK98955658T patent/DK1032565T3/da active
- 1998-11-16 AT AT98955658T patent/ATE232855T1/de active
- 1998-11-17 IN IN3441DE1998 patent/IN191018B/en unknown
- 1998-11-17 MY MYPI98005210A patent/MY121031A/en unknown
- 1998-11-17 CO CO98067508A patent/CO4771105A1/es unknown
- 1998-11-17 ZA ZA9810511A patent/ZA9810511B/xx unknown
- 1998-11-17 US US09/192,502 patent/US5962705A/en not_active Expired - Lifetime
- 1998-11-18 AR ARP980105859A patent/AR017639A1/es active IP Right Grant
- 1998-11-18 TW TW087119100A patent/TW518329B/zh not_active IP Right Cessation
- 1998-11-18 UY UY25256A patent/UY25256A1/es not_active IP Right Cessation
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2000
- 2000-04-26 IS IS5471A patent/IS2272B/is unknown
- 2000-05-11 NO NO20002443A patent/NO325664B1/no not_active IP Right Cessation
- 2000-05-18 OA OA1200000148A patent/OA11384A/fr unknown
- 2000-05-18 BG BG104455A patent/BG64281B1/bg unknown
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