JPS58162597A - 擬似アミノ糖のｎ−置換誘導体，その製造法および用途 - Google Patents
擬似アミノ糖のｎ−置換誘導体，その製造法および用途Info
- Publication number
- JPS58162597A JPS58162597A JP57045345A JP4534582A JPS58162597A JP S58162597 A JPS58162597 A JP S58162597A JP 57045345 A JP57045345 A JP 57045345A JP 4534582 A JP4534582 A JP 4534582A JP S58162597 A JPS58162597 A JP S58162597A
- Authority
- JP
- Japan
- Prior art keywords
- reduced pressure
- under reduced
- water
- eluted
- concentrated under
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 150000002337 glycosamines Chemical class 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000003277 amino group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 7
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims 3
- 108010028144 alpha-Glucosidases Proteins 0.000 abstract description 26
- 125000006239 protecting group Chemical group 0.000 abstract description 13
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 7
- 150000001720 carbohydrates Chemical class 0.000 abstract description 4
- 235000014633 carbohydrates Nutrition 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 235000013373 food additive Nutrition 0.000 abstract description 3
- 239000002778 food additive Substances 0.000 abstract description 3
- 150000003997 cyclic ketones Chemical class 0.000 abstract description 2
- 230000004060 metabolic process Effects 0.000 abstract description 2
- 102100024295 Maltase-glucoamylase Human genes 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910001868 water Inorganic materials 0.000 description 226
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 207
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- 239000000243 solution Substances 0.000 description 124
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- 238000000921 elemental analysis Methods 0.000 description 62
- 238000005406 washing Methods 0.000 description 58
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
- 238000003756 stirring Methods 0.000 description 48
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 46
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- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 40
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 37
- 235000011114 ammonium hydroxide Nutrition 0.000 description 37
- 239000000843 powder Substances 0.000 description 37
- 150000001412 amines Chemical class 0.000 description 30
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- -1 amino sugar compound Chemical class 0.000 description 26
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- 102000016679 alpha-Glucosidases Human genes 0.000 description 25
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- 239000007788 liquid Substances 0.000 description 20
- 229940035423 ethyl ether Drugs 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 16
- 235000011073 invertase Nutrition 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 15
- 235000011054 acetic acid Nutrition 0.000 description 15
- 238000010828 elution Methods 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- GSQYAWMREAXBHF-UOYQFSTFSA-N validamine Chemical class N[C@H]1C[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSQYAWMREAXBHF-UOYQFSTFSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- GSQYAWMREAXBHF-UHFFFAOYSA-N Validamine Natural products NC1CC(CO)C(O)C(O)C1O GSQYAWMREAXBHF-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XPHOBMULWMGEBA-UHFFFAOYSA-N Valienamine Natural products NC1C=C(CO)C(O)C(O)C1O XPHOBMULWMGEBA-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 9
- 229910001863 barium hydroxide Inorganic materials 0.000 description 9
- 238000004364 calculation method Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- XPHOBMULWMGEBA-VZFHVOOUSA-N valienamine Chemical compound N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O XPHOBMULWMGEBA-VZFHVOOUSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 8
- 244000250129 Trigonella foenum graecum Species 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
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- 235000013305 food Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 101000584314 Homo sapiens Myc target protein 1 Proteins 0.000 description 5
- 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 5
- 102100030625 Myc target protein 1 Human genes 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000004108 freeze drying Methods 0.000 description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical class OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 3
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- 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
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Enzymes And Modification Thereof (AREA)
- Saccharide Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57045345A JPS58162597A (ja) | 1982-03-19 | 1982-03-19 | 擬似アミノ糖のｎ−置換誘導体，その製造法および用途 |
| US06/475,615 US4595678A (en) | 1982-03-19 | 1983-03-15 | N-substituted pseudo-aminosugars and pharmaceutical compositions containing same |
| EP83301482A EP0089812B1 (en) | 1982-03-19 | 1983-03-17 | N-substituted pseudo-aminosugars, their production and use |
| DE8383301482T DE3366520D1 (en) | 1982-03-19 | 1983-03-17 | N-substituted pseudo-aminosugars, their production and use |
| CA000424008A CA1208211A (en) | 1982-03-19 | 1983-03-18 | N-substituted pseudo-aminosugars, their production and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57045345A JPS58162597A (ja) | 1982-03-19 | 1982-03-19 | 擬似アミノ糖のｎ−置換誘導体，その製造法および用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58162597A true JPS58162597A (ja) | 1983-09-27 |
| JPH0323536B2 JPH0323536B2 (enrdf_load_stackoverflow) | 1991-03-29 |
Family
ID=12716692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57045345A Granted JPS58162597A (ja) | 1982-03-19 | 1982-03-19 | 擬似アミノ糖のｎ−置換誘導体，その製造法および用途 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58162597A (enrdf_load_stackoverflow) |
-
1982
- 1982-03-19 JP JP57045345A patent/JPS58162597A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0323536B2 (enrdf_load_stackoverflow) | 1991-03-29 |
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