IL96694A - Process for the preparation of 1-dehoxinoirimycin from 1,2,2-isopropylidene-5-oxo-A-D-glucuronolactone - Google Patents

Process for the preparation of 1-dehoxinoirimycin from 1,2,2-isopropylidene-5-oxo-A-D-glucuronolactone

Info

Publication number: IL96694A
Authority: IL; Israel
Prior art keywords: isopropylidene; give; oxo; glucuronolactone; process according
Prior art date: 1989-12-20

Application number

IL9669490A

Other languages

English (en)

Hebrew (he)

Other versions

IL96694A0 (en

Original Assignee

Merrell Dow Pharma

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.)

1989-12-20

Filing date

1990-12-17

Publication date

1994-12-29

1990-12-17 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1991-09-16 Publication of IL96694A0 publication Critical patent/IL96694A0/xx

1994-12-29 Publication of IL96694A publication Critical patent/IL96694A/en

Links

229950002441 glucurolactone Drugs 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims description 38
LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 title abstract description 11
238000002360 preparation method Methods 0.000 title abstract description 9
LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 title description 4
150000002923 oximes Chemical class 0.000 claims abstract description 27
-1 lithium aluminum hydride Chemical compound 0.000 claims description 25
150000001412 amines Chemical class 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
150000004678 hydrides Chemical class 0.000 claims description 7
239000012280 lithium aluminium hydride Substances 0.000 claims description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
230000002829 reductive effect Effects 0.000 claims description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N Di-tert-butyl dicarbonate Substances CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 3
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
PLICPKOWHZITQE-DVKNGEFBSA-N 1-deoxynojirimycin-1-sulfonic acid Chemical compound OC[C@H]1N[C@@H](S(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O PLICPKOWHZITQE-DVKNGEFBSA-N 0.000 claims description 2
AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 claims description 2
125000006242 amine protecting group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims 3
229910000564 Raney nickel Inorganic materials 0.000 claims 3
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 claims 1
BGMYHTUCJVZIRP-UHFFFAOYSA-N Nojirimycin Natural products OCC1NC(O)C(O)C(O)C1O BGMYHTUCJVZIRP-UHFFFAOYSA-N 0.000 abstract description 15
238000006268 reductive amination reaction Methods 0.000 abstract description 4
KLXQAXYSOJNJRI-JGWLITMVSA-N (2r,3s,4r,5r)-5-amino-2,3,4,6-tetrahydroxyhexanal Chemical compound OC[C@@H](N)[C@@H](O)[C@H](O)[C@@H](O)C=O KLXQAXYSOJNJRI-JGWLITMVSA-N 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
BGMYHTUCJVZIRP-GASJEMHNSA-N nojirimycin Chemical compound OC[C@H]1NC(O)[C@H](O)[C@@H](O)[C@@H]1O BGMYHTUCJVZIRP-GASJEMHNSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000001819 mass spectrum Methods 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001540 azides Chemical class 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CLVUFWXGNIFGNC-QTSLKERKSA-N (2r,3s,5r,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@H]1N[C@H](CO)[C@H](O)C(O)[C@@H]1O CLVUFWXGNIFGNC-QTSLKERKSA-N 0.000 description 3
BHJYABWRGNWMJO-UHFFFAOYSA-N 1,2,3-trihydroxypiperidine-2-carboxylic acid Chemical compound OC1CCCN(O)C1(O)C(O)=O BHJYABWRGNWMJO-UHFFFAOYSA-N 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 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
239000000523 sample Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 description 2
UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
HPYMWOKOISXVPN-UHFFFAOYSA-N [CH2-]C(=O)CN=[N+]=[N-] Chemical compound [CH2-]C(=O)CN=[N+]=[N-] HPYMWOKOISXVPN-UHFFFAOYSA-N 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
AEKHNNJSMVVESS-UHFFFAOYSA-N o-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)ON AEKHNNJSMVVESS-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
102000004366 Glucosidases Human genes 0.000 description 1
108010056771 Glucosidases Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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 description 1
HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000006859 Swern oxidation reaction Methods 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003178 anti-diabetic effect Effects 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Polymers 0.000 description 1
102000038379 digestive enzymes Human genes 0.000 description 1
108091007734 digestive enzymes Proteins 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000007040 multi-step synthesis reaction Methods 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
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Endocrinology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

IL9669490A 1989-12-20 1990-12-17 Process for the preparation of 1-dehoxinoirimycin from 1,2,2-isopropylidene-5-oxo-A-D-glucuronolactone IL96694A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US45364789A	1989-12-20	1989-12-20

Publications (2)

Publication Number	Publication Date
IL96694A0 IL96694A0 (en)	1991-09-16
IL96694A true IL96694A (en)	1994-12-29

Family

ID=23801471

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9669490A IL96694A (en)	1989-12-20	1990-12-17	Process for the preparation of 1-dehoxinoirimycin from 1,2,2-isopropylidene-5-oxo-A-D-glucuronolactone

Country Status (14)

Country	Link
US (1)	US5227479A (de)
EP (1)	EP0433978B1 (de)
JP (1)	JP2938193B2 (de)
KR (1)	KR0147819B1 (de)
AT (1)	ATE137758T1 (de)
AU (1)	AU632191B2 (de)
DE (1)	DE69026912T2 (de)
DK (1)	DK0433978T3 (de)
ES (1)	ES2088948T3 (de)
GR (1)	GR3020492T3 (de)
HU (1)	HU207866B (de)
IE (1)	IE72513B1 (de)
IL (1)	IL96694A (de)
ZA (1)	ZA9010083B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066807A (en) *	1990-03-12	1991-11-19	Merrell Dow Pharmaceuticals Inc.	Process for the preparation of castanospermine
US6462197B2 (en)	2000-03-31	2002-10-08	Board Of Trustees Of Michigan State University	Process for the preparation of 1,5-dideoxy-1,5-imino hexitols from oximes or imines

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4634765A (en) *	1984-12-18	1987-01-06	Merrell Dow Pharmaceuticals Inc.	Homodisaccharide hypoglycemic agents
DE3628486A1 (de) *	1986-08-22	1988-02-25	Bayer Ag	Piperidinderivate
US4880917A (en) *	1988-07-01	1989-11-14	Merrell Dow Pharmaceuticals Inc.	Process for hydrolyzing 2,6-dideoxy-2,6-iminoheptononitrile derivatives using trifluoroacetic acid and dinitrogen tetroxide
US4908439A (en) *	1988-09-16	1990-03-13	Merrell Dow Pharmaceuticals Inc.	Synthesis of intermediate useful in the preparation of nojirimycin and related compounds

1990
- 1990-11-14 US US07/610,690 patent/US5227479A/en not_active Expired - Fee Related
- 1990-12-14 AU AU68084/90A patent/AU632191B2/en not_active Ceased
- 1990-12-14 ZA ZA9010083A patent/ZA9010083B/xx unknown
- 1990-12-17 HU HU908300A patent/HU207866B/hu not_active IP Right Cessation
- 1990-12-17 IL IL9669490A patent/IL96694A/en not_active IP Right Cessation
- 1990-12-18 DK DK90124580.3T patent/DK0433978T3/da active
- 1990-12-18 AT AT90124580T patent/ATE137758T1/de not_active IP Right Cessation
- 1990-12-18 ES ES90124580T patent/ES2088948T3/es not_active Expired - Lifetime
- 1990-12-18 EP EP90124580A patent/EP0433978B1/de not_active Expired - Lifetime
- 1990-12-18 DE DE69026912T patent/DE69026912T2/de not_active Expired - Fee Related
- 1990-12-19 JP JP2411708A patent/JP2938193B2/ja not_active Expired - Lifetime
- 1990-12-19 KR KR1019900021075A patent/KR0147819B1/ko not_active Expired - Fee Related
- 1990-12-19 IE IE459890A patent/IE72513B1/en not_active IP Right Cessation
1996
- 1996-07-09 GR GR960401860T patent/GR3020492T3/el unknown

Also Published As

Publication number	Publication date
DE69026912T2 (de)	1996-10-02
AU6808490A (en)	1991-06-27
US5227479A (en)	1993-07-13
ATE137758T1 (de)	1996-05-15
IE72513B1 (en)	1997-04-23
IE904598A1 (en)	1991-07-03
HU908300D0 (en)	1991-06-28
DE69026912D1 (de)	1996-06-13
DK0433978T3 (da)	1996-05-28
KR0147819B1 (ko)	1998-08-01
HU207866B (en)	1993-06-28
IL96694A0 (en)	1991-09-16
JPH0418072A (ja)	1992-01-22
ZA9010083B (en)	1991-10-30
AU632191B2 (en)	1992-12-17
EP0433978A2 (de)	1991-06-26
EP0433978A3 (en)	1992-09-09
JP2938193B2 (ja)	1999-08-23
HUT57224A (en)	1991-11-28
KR910011882A (ko)	1991-08-07
ES2088948T3 (es)	1996-10-01
EP0433978B1 (de)	1996-05-08
GR3020492T3 (en)	1996-10-31

Legal Events

Date	Code	Title	Description
1997-03-18	KB	Patent renewed
2001-08-26	MM9K	Patent not in force due to non-payment of renewal fees

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