JPS58124748A - 新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤 - Google Patents

新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤

Info

Publication number: JPS58124748A
Authority: JP; Japan
Prior art keywords: formula; reaction; culture; alpha; acid
Prior art date: 1982-01-14
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

Application number

JP57004751A

Other languages

English (en)

Japanese (ja)

Other versions

JPH022592B2 (da

Inventor

Yukihiko Kameda

亀田　幸彦

Satoshi Horii

堀井　聰

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

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.)

1982-01-14

Filing date

1982-01-14

Publication date

1983-07-25

1982-01-14 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1982-01-14 Priority to JP57004751A priority Critical patent/JPS58124748A/ja

1982-04-08 Priority to EP82301869A priority patent/EP0063456B1/en

1982-04-08 Priority to DE8282301869T priority patent/DE3260491D1/de

1982-04-08 Priority to CA000400783A priority patent/CA1171374A/en

1982-04-09 Priority to US06/367,105 priority patent/US4827036A/en

1983-07-25 Publication of JPS58124748A publication Critical patent/JPS58124748A/ja

1989-04-27 Priority to US07/343,586 priority patent/US4946779A/en

1990-01-18 Publication of JPH022592B2 publication Critical patent/JPH022592B2/ja

Status Granted legal-status Critical Current

Links

229940077274 Alpha glucosidase inhibitor Drugs 0.000 title abstract description 3
239000003888 alpha glucosidase inhibitor Substances 0.000 title abstract description 3
238000002360 preparation method Methods 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 13
239000003112 inhibitor Substances 0.000 claims description 9
244000005700 microbiome Species 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
150000002736 metal compounds Chemical class 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 13
238000000034 method Methods 0.000 abstract description 12
238000006243 chemical reaction Methods 0.000 abstract description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
239000000126 substance Substances 0.000 abstract description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
239000000843 powder Substances 0.000 abstract description 6
241000187747 Streptomyces Species 0.000 abstract description 4
150000001720 carbohydrates Chemical class 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
239000003153 chemical reaction reagent Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract description 3
235000013373 food additive Nutrition 0.000 abstract description 3
239000002778 food additive Substances 0.000 abstract description 3
241000187391 Streptomyces hygroscopicus Species 0.000 abstract description 2
201000001421 hyperglycemia Diseases 0.000 abstract description 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 abstract description 2
239000000654 additive Substances 0.000 abstract 1
230000000996 additive effect Effects 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
230000004060 metabolic process Effects 0.000 abstract 1
XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
239000002609 medium Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
-1 polyproform Chemical compound 0.000 description 9
230000002829 reductive effect Effects 0.000 description 7
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 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
235000013305 food Nutrition 0.000 description 6
239000008103 glucose Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
239000000047 product Substances 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000007788 liquid Substances 0.000 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 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
102000016679 alpha-Glucosidases Human genes 0.000 description 4
108010028144 alpha-Glucosidases Proteins 0.000 description 4
239000003456 ion exchange resin Substances 0.000 description 4
229920003303 ion-exchange polymer Polymers 0.000 description 4
239000000203 mixture Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
108010056771 Glucosidases Proteins 0.000 description 3
102000004366 Glucosidases Human genes 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
238000013019 agitation Methods 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
239000007853 buffer solution Substances 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000012258 culturing Methods 0.000 description 3
238000010828 elution Methods 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
235000015203 fruit juice Nutrition 0.000 description 3
229940093915 gynecological organic acid Drugs 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
235000015094 jam Nutrition 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
108010016626 Dipeptides Proteins 0.000 description 2
235000016623 Fragaria vesca Nutrition 0.000 description 2
240000009088 Fragaria x ananassa Species 0.000 description 2
235000011363 Fragaria x ananassa Nutrition 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 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 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000005273 aeration Methods 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000003674 animal food additive Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
108010051210 beta-Fructofuranosidase Proteins 0.000 description 2
235000013361 beverage Nutrition 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
208000002925 dental caries Diseases 0.000 description 2
238000010586 diagram Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
235000011073 invertase Nutrition 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
244000144972 livestock Species 0.000 description 2
235000004213 low-fat Nutrition 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
208000030159 metabolic disease Diseases 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
235000014593 oils and fats Nutrition 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000012545 processing Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000143060 Americamysis bahia Species 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000238557 Decapoda Species 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004278 EU approved seasoning Substances 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
238000008458 Glucose Oxidase Reagent Methods 0.000 description 1
206010018429 Glucose tolerance impaired Diseases 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
229920002527 Glycogen Polymers 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
235000004347 Perilla Nutrition 0.000 description 1
244000124853 Perilla frutescens Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000001280 Prediabetic State Diseases 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSQYAWMREAXBHF-UHFFFAOYSA-N Validamine Natural products NC1CC(CO)C(O)C(O)C1O GSQYAWMREAXBHF-UHFFFAOYSA-N 0.000 description 1
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
241000908656 Vestiaria coccinea Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
235000019730 animal feed additive Nutrition 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012539 chromatography resin Substances 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000012937 correction Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000012136 culture method Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000003795 desorption Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
230000004153 glucose metabolism Effects 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
235000021056 liquid food Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000011785 micronutrient Substances 0.000 description 1
235000013369 micronutrients Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
239000003471 mutagenic agent Substances 0.000 description 1
231100000707 mutagenic chemical Toxicity 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
201000009104 prediabetes syndrome Diseases 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012925 reference material Substances 0.000 description 1
235000012046 side dish Nutrition 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
235000014214 soft drink Nutrition 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000002336 sorption--desorption measurement Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000013076 target substance Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
GSQYAWMREAXBHF-UOYQFSTFSA-N validamine Chemical compound N[C@H]1C[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GSQYAWMREAXBHF-UOYQFSTFSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000002699 waste material Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Enzymes And Modification Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP57004751A 1981-04-13 1982-01-14 新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤 Granted JPS58124748A (ja)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
JP57004751A JPS58124748A (ja)	1982-01-14	1982-01-14	新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤
EP82301869A EP0063456B1 (en)	1981-04-13	1982-04-08	Pseudo-aminosugars, their production and use
DE8282301869T DE3260491D1 (en)	1981-04-13	1982-04-08	Pseudo-aminosugars, their production and use
CA000400783A CA1171374A (en)	1981-04-13	1982-04-08	Pseudo-aminosugars, their production and use
US06/367,105 US4827036A (en)	1981-04-13	1982-04-09	Pseudo-aminosugars, their production and use
US07/343,586 US4946779A (en)	1981-04-13	1989-04-27	Pseudo-aminosugars, their production and use

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57004751A JPS58124748A (ja)	1982-01-14	1982-01-14	新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤

Publications (2)

Publication Number	Publication Date
JPS58124748A true JPS58124748A (ja)	1983-07-25
JPH022592B2 JPH022592B2 (da)	1990-01-18

Family

ID=11592608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57004751A Granted JPS58124748A (ja)	1981-04-13	1982-01-14	新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤

Country Status (1)

Country	Link
JP (1)	JPS58124748A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005053899A (ja) *	2003-07-23	2005-03-03	Hokko Chem Ind Co Ltd	新規カルバ糖誘導体および該新規カルバ糖誘導体を原料とする擬似アミノ糖誘導体の製造法

1982
- 1982-01-14 JP JP57004751A patent/JPS58124748A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005053899A (ja) *	2003-07-23	2005-03-03	Hokko Chem Ind Co Ltd	新規カルバ糖誘導体および該新規カルバ糖誘導体を原料とする擬似アミノ糖誘導体の製造法

Also Published As

Publication number	Publication date
JPH022592B2 (da)	1990-01-18

Publication	Publication Date	Title
US4827036A (en)	1989-05-02	Pseudo-aminosugars, their production and use
DE2905649A1 (de)	1979-08-16	Neue aminozucker-derivate, ihre herstellung und verwendung als amylasehemmende mittel
JPH02196780A (ja)	1990-08-03	グリコシダーゼ阻害剤サルボスタチンおよびその製法
JPH035398B2 (da)	1991-01-25
JPS60115599A (ja)	1985-06-22	Ｂｂｍ―２４７８ａ抗生物質
JPS6041491A (ja)	1985-03-05	新規抗生物質
US4316894A (en)	1982-02-23	Antibiotic SF-1130-x3 3 substance and production and use thereof
JPS6276A (ja)	1987-01-06	酵素阻害性新規物質
JPS61216692A (ja)	1986-09-26	Ｃｌ‐１５７７‐ｂ↓４化合物およびその製法
JPS58124748A (ja)	1983-07-25	新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤
KR900008247B1 (ko)	1990-11-06	새로운 생리활성물질 아르파메닌(Arphamenine)의 제조방법
JPS60246396A (ja)	1985-12-06	酵素阻害物質ジヒドロデスオキシグリゼオ−ル酸及びその塩類
JPS58152496A (ja)	1983-09-10	バリエナミンおよびバリダミンの製造法
AU597340B2 (en)	1990-05-31	Efomycin G, its preparation and its use as a yield promoter in animals
JPH01272586A (ja)	1989-10-31	抗コクシジウム活性および成長促進活性を有する酸性の多環式エーテル抗生物質
Wheat et al.	1964	Isolation of D-fucosamine from Bacillus cereus
JPH022590B2 (da)	1990-01-18
JPS62155290A (ja)	1987-07-10	炭水化物代謝制御剤
JPS6248692A (ja)	1987-03-03	バリオ−ルアミン誘導体およびその製造法
JPS6055065B2 (ja)	1985-12-03	５−アミノ−２−カルボキシ−４−オキソ−１，４，５，６−テトラヒドロピリジン−３−酢酸誘導体
JPS6034190A (ja)	1985-02-21	アルフアメニンの高収率製造法
JPH0429356B2 (da)	1992-05-18
JPH01216927A (ja)	1989-08-30	抗腫瘍剤
JPS584039B2 (ja)	1983-01-24	抗生物質ｄｍｂおよびその製法
JPS61280472A (ja)	1986-12-11	β−ガラクトシダ−ゼ阻害物質ガラクトスタチン類およびその製造方法

JPS58124748A - 新規アミノシクリト−ル、その製造法およびα−グルコシダ−ゼ阻害剤 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (6)

Applications Claiming Priority (1)

Publications (2)

Family

ID=11592608

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

Similar Documents