HU212496B - Process for producing nojirimycin derivatives and pharmaceutical compositions containing the same - Google Patents
Process for producing nojirimycin derivatives and pharmaceutical compositions containing the same Download PDFInfo
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- HU212496B HU212496B HU911430A HU143091A HU212496B HU 212496 B HU212496 B HU 212496B HU 911430 A HU911430 A HU 911430A HU 143091 A HU143091 A HU 143091A HU 212496 B HU212496 B HU 212496B
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- Hungary
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- april
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- 238000000034 method Methods 0.000 title claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- BGMYHTUCJVZIRP-GASJEMHNSA-N nojirimycin Chemical class OC[C@H]1NC(O)[C@H](O)[C@@H](O)[C@@H]1O BGMYHTUCJVZIRP-GASJEMHNSA-N 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 102100024295 Maltase-glucoamylase Human genes 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 108010028144 alpha-Glucosidases Proteins 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 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 1
- LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical class OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 abstract description 10
- 208000030507 AIDS Diseases 0.000 abstract description 8
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 6
- 241001430294 unidentified retrovirus Species 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
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- -1 η-propyl Chemical group 0.000 description 39
- 229960002920 sorbitol Drugs 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 125000001841 imino group Chemical group [H]N=* 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 29
- 229910002027 silica gel Inorganic materials 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 238000003818 flash chromatography Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- 235000011152 sodium sulphate Nutrition 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 102000051759 human factor J Human genes 0.000 description 12
- 108700008420 human factor J Proteins 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 235000010356 sorbitol Nutrition 0.000 description 8
- MOXLNVPNJIVLKN-HVWQDESWSA-N (2r,3r,4s,5s)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)piperidin-3-ol Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](OCC=2C=CC=CC=2)CN1)OCC=1C=CC=CC=1)O)OCC1=CC=CC=C1 MOXLNVPNJIVLKN-HVWQDESWSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 description 6
- 208000008589 Obesity Diseases 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 235000020824 obesity Nutrition 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- NVEYOAXSXPSFHL-UHFFFAOYSA-N 3-bromopropyl(trimethyl)silane Chemical compound C[Si](C)(C)CCCBr NVEYOAXSXPSFHL-UHFFFAOYSA-N 0.000 description 4
- SZCGFQALLUBALV-UHFFFAOYSA-N 4-trimethylsilylbutanoic acid Chemical compound C[Si](C)(C)CCCC(O)=O SZCGFQALLUBALV-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
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- 229920001429 chelating resin Polymers 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- RVLGUXNVMKOVQM-UHFFFAOYSA-N 3-iodopropyl(trimethyl)silane Chemical compound C[Si](C)(C)CCCI RVLGUXNVMKOVQM-UHFFFAOYSA-N 0.000 description 3
- MDJXWYVEZHDNPO-UHFFFAOYSA-N 4-trimethylsilylbutan-1-ol Chemical compound C[Si](C)(C)CCCCO MDJXWYVEZHDNPO-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
- OYIHPTRFAXUETJ-UHFFFAOYSA-N benzyl-(iodomethyl)-dimethylsilane Chemical compound IC[Si](C)(C)CC1=CC=CC=C1 OYIHPTRFAXUETJ-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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- LEKDMXXQOPURTF-UHFFFAOYSA-N tert-butyl-(iodomethyl)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)CI LEKDMXXQOPURTF-UHFFFAOYSA-N 0.000 description 3
- MNMAOUWAPYRASC-GJMNKMQNSA-N (2r,3s,4r)-2-[(1r)-1-azido-2-phenylmethoxyethyl]-5-methoxy-3,4-bis(phenylmethoxy)oxolane Chemical compound C([C@H]([C@H]1OC([C@@H]([C@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)OC)N=[N+]=[N-])OCC1=CC=CC=C1 MNMAOUWAPYRASC-GJMNKMQNSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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Classifications
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- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Claims (16)
- SZABADALMI IGÉNYPONTOK1. Eljárás (I) általános képletű vegyületek, ahol Q jelentése 1-6 szénatomos alkilén-, 3-7 szénatomos alkenilén- vagy fenilén-(l-4 szénatomos alkilén)-csoport, ahol a feniléncsoport a Si atomhoz kapcsolódik,R2 és R3 jelentése 1-6 szénatomos alkil- vagy fenilcsoport,Rj jelentése 1-6 szénatomos alkilcsoport, és geometriai izomeijeik, valamint gyógyászatilag elfogadható sóik előállítására, azzal jellemezve, hogy egy adott esetben védett hidroxicsoportokat tartalmazó (II) általános képletű vegyületet - ahol R jelentése hidrogénatom vagy adott esetben védőcsoport - egy X'-Q-SiR1R2R3 általános képletű vegyülettel - ahol X' jelentése halogénatom, mezilát- vagy tozilátcsoport - reagáltatunk, azután adott esetben a hidroxivédő csoportokat eltávolítjuk, majd szükség esetén a védőcsoportok lehasítása során keletkezett aniont semlegesítjük, és kívánt esetben a keletkezett (I) általános képletű vegyületeket sóvá alakítjuk.(Elsőbbsége: 1991. 04. 26.)HU 212 496 Β
- 2. Eljárás (I) általános képletű vegyületek, aholQ jelentése 1-6 szénatomos alkilén- vagy 3-6 szénatomos alkenilén-csoport,Rp R2 és Rj jelentése 1-6 szénatomos alkilcsoport, valamint gyógyászatilag elfogadható sóik előállítására, azzal jellemezve, hogy egy, adott esetben védett hidroxicsoportokat tartalmazó (Π) általános képletű vegyületet - ahol R jelentése hidrogénatom vagy adott esetben védőcsoport - egy X'-QSiR!R2R3 általános képletű vegyülettel - ahol X' jelentése halogénatom, mezilát- vagy tozilátcsoport - reagáltatunk, azután adott esetben a hidroxivédő csoportokat eltávolítjuk, majd szükség esetén a védőcsoportok lehasítása során keletkezett aniont semlegesítjük, és kívánt esetben a keletkezett (I) általános képletű vegyületeket sóvá alakítjuk. (Elsőbbsége: 1990. 04. 27.)
- 3. A 2. igénypont szerinti eljárás olyan (I) általános képletű vegyületek előállítására, melyekben Q jelentése 1-6 szénatomos alkiléncsoport, R,, R2 és R3 jelentése pedig a 2. igénypont szerinti, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1990. 04. 27.)
- 4. A 3. igénypont szerinti eljárás olyan (I) általános képletű vegyületek előállítására, melyekben Q jelentése metiléncsoport, Rb R2 és R3 jelentése a 3. igénypont szerinti, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1990. 04. 27.)
- 5. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyületek előállítására, melyekben Q jelentése -CH2-fenilén-csoport és R,, R2 ésR3 mindegyike Ιό szénatomos alkilcsoportot jelent, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991.04.26.)
- 6. A 2. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiR]R2R3 szubsztituens jelentése -CH2-Si-(CH3)3 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1990. 04. 27.)
- 7. A 2. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiRiR2R3 szubsztituens jelentése -(CH2)3-Si-(CH3)3 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1990. 04. 27.)
- 8. A 2. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiRjR2R3 szubsztituens jelentése -(CH2)4-Si-(CH3)3 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1990. 04. 27.)
- 9. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiRjR2R3 szubsztituens jelentése -CH2-Si-(CH3)2C6H5 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991.04. 26.)
- 10. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiR,R2R3 szubsztituens jelentése -CH2-Si-(CH3)2C2Hj csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991. 04. 26.)
- 11. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiR|R2R3 szubsztituens jelentése -CH2-Si-(CH3)2C3H7 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991.04. 26.)
- 12. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiRjR2R3 szubsztituens jelentése transz-CH2-CH=CHSi-(CH3)3 csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991. 04. 26.)
- 13. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiR,R2R3 szubsztituens jelentése (m) képletű csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991. 04. 26.)
- 14. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyület előállítására, melyben a -Q-SiR]R2R3 szubsztituens jelentése (h) képletű csoport, azzal jellemezve, hogy a megfelelő kiindulási anyagokat alkalmazzuk.(Elsőbbsége: 1991. 04. 26.)
- 15. Eljárás (I) általános képletű vegyületek, aholQ jelentése 1-6 szénatomos alkilén-, 2-8 szénatomos alkenilén- vagy fenilén-(l-4 szénatomos alkilén)csoport,R|, R2ésR3 jelentése 1-6 szénatomos alkil- vagy fenil-csoport, és geometriai izomeijeik, valamint gyógyászatilag elfogadható sóik előállítására, azzal jellemezve, hogy egy, adott esetben védett hidroxicsoportokat tartalmazó (H) általános képletű vegyületet - ahol R jelentése hidrogénatom vagy adott esetben védőcsoportot - egy X'-QSiRiR2R3 általános képletű vegyülettel - ahol X' jelentése halogénatom, mezilát- vagy tozilát csoport - reagáltatunk, azután adott esetben a hidroxivédő csoportokat eltávolítjuk, vagy ha R]-R3 valamelyikének jelentése2-6 szénatomos alkenil-csoport, a védőcsoportok eltávolításával egyidejűleg ezt alkilcsoporttá redukáljuk, majd szükség esetén a védőcsoportok lehasítása során keletkezett aniont semlegesítjük és kívánt esetben a keletkezett (I) általános képletű vegyületeket sóvá alakítjuk. (Elsőbbsége: 1993.06.21.)
- 16. Eljárás hatóanyagként az ot-glükozidáz enzimet inhibeáló hatású (I) általános képletű vegyületet - ahol Q, R,, R2 és R3 jelentése az 1. igénypontban megadott vagy geometriai izomerjeit, vagy gyógyászatilag elfogadható sóit tartalmazó gyógyszerkészítmény előállítására, azzal jellemezve, hogy egy, az 1. igénypont szerinti módon előállított (I) általános képletű vegyületet gyógyászati hordozó és/vagy egyéb segédanyagokkal összekeverve gyógyszerkészítménnyé dolgozzuk fel.(Elsőbbsége: 1991.04. 26.)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP90401169A EP0453692A1 (en) | 1990-04-27 | 1990-04-27 | Novel nojirimycin derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU911430D0 HU911430D0 (en) | 1991-11-28 |
| HUT57782A HUT57782A (en) | 1991-12-30 |
| HU212496B true HU212496B (en) | 1996-07-29 |
Family
ID=8205706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU911430A HU212496B (en) | 1990-04-27 | 1991-04-26 | Process for producing nojirimycin derivatives and pharmaceutical compositions containing the same |
Country Status (20)
| Country | Link |
|---|---|
| EP (2) | EP0453692A1 (hu) |
| JP (1) | JP2968088B2 (hu) |
| KR (1) | KR100191051B1 (hu) |
| CN (1) | CN1028368C (hu) |
| AR (1) | AR248026A1 (hu) |
| AT (1) | ATE132153T1 (hu) |
| AU (1) | AU632926B2 (hu) |
| CA (1) | CA2041331C (hu) |
| DE (1) | DE69115750T2 (hu) |
| DK (1) | DK0454580T3 (hu) |
| ES (1) | ES2084126T3 (hu) |
| FI (1) | FI97885C (hu) |
| GR (1) | GR3018797T3 (hu) |
| HU (1) | HU212496B (hu) |
| IE (1) | IE72477B1 (hu) |
| IL (1) | IL97975A (hu) |
| NO (1) | NO179913C (hu) |
| PT (1) | PT97485B (hu) |
| TW (1) | TW201302B (hu) |
| ZA (1) | ZA912994B (hu) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5986230A (en) * | 1996-09-13 | 1999-11-16 | Uncle Ben's, Inc. | Method and apparatus for sorting product |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) * | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| GB8705654D0 (en) * | 1987-03-10 | 1987-04-15 | Safe Haul Ltd | Pneumatic valve |
| EP0282618A1 (en) * | 1987-03-18 | 1988-09-21 | Vereniging Het Nederlands Kanker Instituut | 1-Deoxynojirimycin as an anti-HIV therapeutic |
| EP0350012A3 (en) * | 1988-07-08 | 1990-09-05 | Meiji Seika Kaisha Ltd. | Antiviral composition |
| US5043273A (en) * | 1989-08-17 | 1991-08-27 | Monsanto Company | Phosphorylated glycosidase inhibitor prodrugs |
-
1990
- 1990-04-27 EP EP90401169A patent/EP0453692A1/en not_active Withdrawn
-
1991
- 1991-04-22 ZA ZA912994A patent/ZA912994B/xx unknown
- 1991-04-23 TW TW080103185A patent/TW201302B/zh active
- 1991-04-24 AR AR91319515A patent/AR248026A1/es active
- 1991-04-24 AU AU75351/91A patent/AU632926B2/en not_active Ceased
- 1991-04-25 ES ES91401096T patent/ES2084126T3/es not_active Expired - Lifetime
- 1991-04-25 EP EP91401096A patent/EP0454580B1/en not_active Expired - Lifetime
- 1991-04-25 DK DK91401096.2T patent/DK0454580T3/da active
- 1991-04-25 DE DE69115750T patent/DE69115750T2/de not_active Expired - Fee Related
- 1991-04-25 AT AT91401096T patent/ATE132153T1/de not_active IP Right Cessation
- 1991-04-26 JP JP3122818A patent/JP2968088B2/ja not_active Expired - Fee Related
- 1991-04-26 IL IL9797591A patent/IL97975A/en not_active IP Right Cessation
- 1991-04-26 HU HU911430A patent/HU212496B/hu not_active IP Right Cessation
- 1991-04-26 CA CA002041331A patent/CA2041331C/en not_active Expired - Fee Related
- 1991-04-26 IE IE141791A patent/IE72477B1/en not_active IP Right Cessation
- 1991-04-26 KR KR1019910006722A patent/KR100191051B1/ko not_active IP Right Cessation
- 1991-04-26 CN CN91102641A patent/CN1028368C/zh not_active Expired - Fee Related
- 1991-04-26 NO NO911665A patent/NO179913C/no unknown
- 1991-04-26 PT PT97485A patent/PT97485B/pt not_active IP Right Cessation
- 1991-04-26 FI FI912033A patent/FI97885C/fi not_active IP Right Cessation
-
1996
- 1996-01-25 GR GR960400185T patent/GR3018797T3/el unknown
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