IL97487A - Process for making castanospermine - Google Patents

Process for making castanospermine

Info

Publication number: IL97487A
Authority: IL; Israel
Prior art keywords: give; isopropylidene; glucuronolactone; ethyl acetate; amino
Prior art date: 1990-03-12

Application number

IL9748791A

Other languages

English (en)

Hebrew (he)

Other versions

IL97487A0 (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.)

1990-03-12

Filing date

1991-03-08

Publication date

1995-05-26

1991-03-08 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1992-06-21 Publication of IL97487A0 publication Critical patent/IL97487A0/xx

1995-05-26 Publication of IL97487A publication Critical patent/IL97487A/en

Links

238000000034 method Methods 0.000 title claims abstract description 22
JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 title claims abstract description 21
JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical compound C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 title claims abstract description 21
238000002360 preparation method Methods 0.000 title description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 69
229950002441 glucurolactone Drugs 0.000 claims abstract description 26
125000006239 protecting group Chemical group 0.000 claims abstract description 6
125000004122 cyclic group Chemical group 0.000 claims abstract description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
-1 amine salt Chemical class 0.000 claims description 21
239000003054 catalyst Substances 0.000 claims description 13
150000003951 lactams Chemical class 0.000 claims description 12
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
238000001816 cooling Methods 0.000 claims description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
239000003456 ion exchange resin Substances 0.000 claims description 4
229920003303 ion-exchange polymer Polymers 0.000 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
150000002596 lactones Chemical class 0.000 claims description 3
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
229910003446 platinum oxide Inorganic materials 0.000 claims description 2
239000007858 starting material Substances 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 3
230000009467 reduction Effects 0.000 abstract description 3
JQBCKRZQAMELAD-UHFFFAOYSA-N 1-hydroxypyrrolidin-2-one Chemical class ON1CCCC1=O JQBCKRZQAMELAD-UHFFFAOYSA-N 0.000 abstract description 2
CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical class ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
229910001868 water Inorganic materials 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000001819 mass spectrum Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
102220305863 rs1015663503 Human genes 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JDVVGAQPNNXQDW-SLBCVNJHSA-N 6-epicastanospermine Natural products C1[C@@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-SLBCVNJHSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N Di-tert-butyl dicarbonate Substances CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 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
239000002253 acid Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
102000038379 digestive enzymes Human genes 0.000 description 1
108091007734 digestive enzymes Proteins 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
125000003147 glycosyl group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
HAJKHJOABGFIGP-UHFFFAOYSA-N indolizidine Chemical class C1CCCN2CCCC21 HAJKHJOABGFIGP-UHFFFAOYSA-N 0.000 description 1
229930005307 indolizidine alkaloid Natural products 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 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
238000012587 nuclear overhauser effect experiment Methods 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
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 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
239000007787 solid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000003643 water by type Substances 0.000 description 1
150000003953 γ-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
- 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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrrole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL9748791A 1990-03-12 1991-03-08 Process for making castanospermine IL97487A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/492,507 US5066807A (en)	1990-03-12	1990-03-12	Process for the preparation of castanospermine

Publications (2)

Publication Number	Publication Date
IL97487A0 IL97487A0 (en)	1992-06-21
IL97487A true IL97487A (en)	1995-05-26

Family

ID=23956525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9748791A IL97487A (en)	1990-03-12	1991-03-08	Process for making castanospermine

Country Status (15)

Country	Link
US (1)	US5066807A (fr)
EP (1)	EP0446832B1 (fr)
JP (1)	JP3019269B2 (fr)
KR (1)	KR0160136B1 (fr)
AT (1)	ATE139231T1 (fr)
AU (1)	AU630543B2 (fr)
CA (1)	CA2037608C (fr)
DE (1)	DE69120108T2 (fr)
DK (1)	DK0446832T3 (fr)
ES (1)	ES2090156T3 (fr)
GR (1)	GR3020707T3 (fr)
HU (1)	HU210048B (fr)
IE (1)	IE910803A1 (fr)
IL (1)	IL97487A (fr)
ZA (1)	ZA911742B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5288875A (en) *	1991-08-14	1994-02-22	Cha Jin K	Synthesis of (-)-swainsonine and intermediate compounds employed in such synthesis
ES2114566T3 (es) *	1991-08-09	1998-06-01	Nycomed Innovation Ab	Uso de radicales libres persistentes en formacion de imagenes por resonancia magnetica nuclear.
GB0110832D0 (en) *	2001-05-03	2001-06-27	Virogen Ltd	Antiviral compounds
JP2008515816A (ja) *	2004-10-06	2008-05-15	ミジェニックスインコーポレイテッド	カスタノスペルミンを含有する、併用抗ウイルス組成物およびその使用方法
US10377818B2 (en)	2015-01-30	2019-08-13	The Board Of Trustees Of The Leland Stanford Junior University	Method of treating glioma
KR101966101B1 (ko)	2017-11-27	2019-04-05	주식회사 인트켐	결정성장 촉진형 하이브리드 자기치유 혼화재의 제조방법과 그 자기치유 혼화재를 이용한 시멘트 결합재 조성물

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1315276C (fr) *	1987-07-02	1993-03-30	Paul S. Liu	Esters et glucosides de castanospermine
US4970317A (en) *	1989-08-08	1990-11-13	Merrell Dow Pharmaceuticals Inc.	Process for the preparation of castanospermine esters
US5227479A (en) *	1989-12-20	1993-07-13	Merrell Dow Pharmaceuticals Inc.	Process for the preparation of nojirimycin and related compounds

1990
- 1990-03-12 US US07/492,507 patent/US5066807A/en not_active Expired - Lifetime
1991
- 1991-03-06 CA CA002037608A patent/CA2037608C/fr not_active Expired - Lifetime
- 1991-03-06 AU AU72640/91A patent/AU630543B2/en not_active Expired
- 1991-03-08 ZA ZA911742A patent/ZA911742B/xx unknown
- 1991-03-08 IL IL9748791A patent/IL97487A/en not_active IP Right Cessation
- 1991-03-11 JP JP3069414A patent/JP3019269B2/ja not_active Expired - Lifetime
- 1991-03-11 IE IE080391A patent/IE910803A1/en not_active IP Right Cessation
- 1991-03-11 HU HU91790A patent/HU210048B/hu unknown
- 1991-03-11 DK DK91103682.0T patent/DK0446832T3/da active
- 1991-03-11 DE DE69120108T patent/DE69120108T2/de not_active Expired - Lifetime
- 1991-03-11 ES ES91103682T patent/ES2090156T3/es not_active Expired - Lifetime
- 1991-03-11 KR KR1019910003856A patent/KR0160136B1/ko not_active Expired - Lifetime
- 1991-03-11 EP EP91103682A patent/EP0446832B1/fr not_active Expired - Lifetime
- 1991-03-11 AT AT91103682T patent/ATE139231T1/de not_active IP Right Cessation
1996
- 1996-08-02 GR GR960402071T patent/GR3020707T3/el unknown

Also Published As

Publication number	Publication date
EP0446832A2 (fr)	1991-09-18
DE69120108D1 (de)	1996-07-18
DE69120108T2 (de)	1997-02-06
JPH04217978A (ja)	1992-08-07
AU630543B2 (en)	1992-10-29
DK0446832T3 (da)	1996-07-01
US5066807A (en)	1991-11-19
EP0446832A3 (en)	1992-03-25
ZA911742B (en)	1991-12-24
ATE139231T1 (de)	1996-06-15
EP0446832B1 (fr)	1996-06-12
ES2090156T3 (es)	1996-10-16
AU7264091A (en)	1991-09-12
IL97487A0 (en)	1992-06-21
JP3019269B2 (ja)	2000-03-13
IE910803A1 (en)	1991-09-25
GR3020707T3 (en)	1996-11-30
KR0160136B1 (ko)	1998-12-01
CA2037608A1 (fr)	1991-09-13
HU210048B (en)	1995-01-30
HU910790D0 (en)	1991-09-30
CA2037608C (fr)	2000-11-21
KR910016749A (ko)	1991-11-05
HUT57208A (en)	1991-11-28

Legal Events

Date	Code	Title
1997-07-13	KB	Patent renewed
2001-06-14	KB	Patent renewed
2005-05-17	KB	Patent renewed
2009-08-31	KB	Patent renewed
2011-12-29	EXP	Patent expired

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