CA1044164A - Glycoside amylase - Google Patents

Glycoside amylase

Info

Publication number: CA1044164A
Authority: CA; Canada
Prior art keywords: alpha; compound; glucose; formula; amino sugar
Prior art date: 1973-09-22
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.): Expired

Application number

CA209,484A

Other languages

English (en)

Other versions

CA209484S (en

Inventor

Walter Puls

Delf Schmidt

Lutz Muller

Uwe Keup

Bodo Junge

Werner Frommer

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1973-09-22

Filing date

1974-09-18

Publication date

1978-12-12

1974-09-18 Application filed by Bayer AG filed Critical Bayer AG

1978-12-12 Application granted granted Critical

1978-12-12 Publication of CA1044164A publication Critical patent/CA1044164A/fr

Status Expired legal-status Critical Current

Links

150000002336 glycosamine derivatives Chemical class 0.000 title abstract description 9
102000005744 Glycoside Hydrolases Human genes 0.000 title abstract description 4
108010031186 Glycoside Hydrolases Proteins 0.000 title abstract description 4
230000002401 inhibitory effect Effects 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 119
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 63
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 claims abstract description 61
239000008103 glucose Substances 0.000 claims abstract description 59
150000002337 glycosamines Chemical class 0.000 claims abstract description 21
239000000463 material Substances 0.000 claims abstract description 10
150000002482 oligosaccharides Chemical group 0.000 claims abstract description 7
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 claims description 58
238000000034 method Methods 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 23
239000000126 substance Substances 0.000 claims description 20
239000006228 supernatant Substances 0.000 claims description 8
238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
-1 amino sugar compound Chemical class 0.000 claims description 5
238000002955 isolation Methods 0.000 claims description 5
238000001556 precipitation Methods 0.000 claims description 4
241000352333 Amegilla alpha Species 0.000 claims 2
125000002091 cationic group Chemical group 0.000 claims 2
230000000153 supplemental effect Effects 0.000 claims 1
210000001035 gastrointestinal tract Anatomy 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 70
239000000243 solution Substances 0.000 description 58
239000000203 mixture Substances 0.000 description 50
150000002500 ions Chemical class 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
108010051210 beta-Fructofuranosidase Proteins 0.000 description 38
235000011073 invertase Nutrition 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
230000005764 inhibitory process Effects 0.000 description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
239000004382 Amylase Substances 0.000 description 27
239000003610 charcoal Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000003112 inhibitor Substances 0.000 description 21
238000012360 testing method Methods 0.000 description 21
230000000694 effects Effects 0.000 description 18
102000013142 Amylases Human genes 0.000 description 17
108010065511 Amylases Proteins 0.000 description 17
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 17
229920002472 Starch Polymers 0.000 description 17
235000019418 amylase Nutrition 0.000 description 17
150000001720 carbohydrates Chemical group 0.000 description 17
239000000047 product Substances 0.000 description 17
239000008107 starch Substances 0.000 description 17
235000019698 starch Nutrition 0.000 description 17
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 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
229920001467 poly(styrenesulfonates) Polymers 0.000 description 16
238000002360 preparation method Methods 0.000 description 16
229920001429 chelating resin Polymers 0.000 description 15
239000000499 gel Substances 0.000 description 14
235000014633 carbohydrates Nutrition 0.000 description 13
238000000338 in vitro Methods 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
235000015097 nutrients Nutrition 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
102000004190 Enzymes Human genes 0.000 description 11
108090000790 Enzymes Proteins 0.000 description 11
239000000872 buffer Substances 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
229940088598 enzyme Drugs 0.000 description 11
102000016679 alpha-Glucosidases Human genes 0.000 description 10
108010028144 alpha-Glucosidases Proteins 0.000 description 10
238000003795 desorption Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
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
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 9
229930006000 Sucrose Natural products 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000005720 sucrose Substances 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
239000003392 amylase inhibitor Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
229910000019 calcium carbonate Inorganic materials 0.000 description 8
230000015556 catabolic process Effects 0.000 description 8
238000006731 degradation reaction Methods 0.000 description 8
238000000855 fermentation Methods 0.000 description 8
230000004151 fermentation Effects 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000001727 in vivo Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
201000001421 hyperglycemia Diseases 0.000 description 7
150000002772 monosaccharides Chemical class 0.000 description 7
229910000069 nitrogen hydride Inorganic materials 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
235000010633 broth Nutrition 0.000 description 6
229940041514 candida albicans extract Drugs 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000001913 cellulose Substances 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
239000012138 yeast extract Substances 0.000 description 6
RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
235000010980 cellulose Nutrition 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004366 Glucose oxidase Substances 0.000 description 4
108010015776 Glucose oxidase Proteins 0.000 description 4
102000004157 Hydrolases Human genes 0.000 description 4
108090000604 Hydrolases Proteins 0.000 description 4
229920004890 Triton X-100 Polymers 0.000 description 4
239000013504 Triton X-100 Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
235000010216 calcium carbonate Nutrition 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000007423 decrease Effects 0.000 description 4
229910000396 dipotassium phosphate Inorganic materials 0.000 description 4
MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000004108 freeze drying Methods 0.000 description 4
229940116332 glucose oxidase Drugs 0.000 description 4
235000019420 glucose oxidase Nutrition 0.000 description 4
238000011534 incubation Methods 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
230000011987 methylation Effects 0.000 description 4
238000007069 methylation reaction Methods 0.000 description 4
244000005700 microbiome Species 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
229940122816 Amylase inhibitor Drugs 0.000 description 3
108010076119 Caseins Proteins 0.000 description 3
241000237074 Centris Species 0.000 description 3
238000008458 Glucose Oxidase Reagent Methods 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
239000013543 active substance Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000005018 casein Substances 0.000 description 3
108010079058 casein hydrolysate Proteins 0.000 description 3
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
235000021240 caseins Nutrition 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
239000007857 degradation product Substances 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
239000012634 fragment Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
210000000813 small intestine Anatomy 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000006188 syrup Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 2
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000518994 Conta Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
229930091371 Fructose Natural products 0.000 description 2
239000005715 Fructose Substances 0.000 description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
208000013016 Hypoglycemia Diseases 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
102000004877 Insulin Human genes 0.000 description 2
108090001061 Insulin Proteins 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
102000003992 Peroxidases Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
244000299461 Theobroma cacao Species 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000008351 acetate buffer Substances 0.000 description 2
238000005273 aeration Methods 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 2
229940025131 amylases Drugs 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
235000013405 beer Nutrition 0.000 description 2
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
238000011088 calibration curve Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000007073 chemical hydrolysis Effects 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
235000019219 chocolate Nutrition 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000012258 culturing Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229940125396 insulin Drugs 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HTAATVDZOHXHBE-UHFFFAOYSA-N methyl 10-formyl-3,9-dihydroxy-1,4,7-trimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylate Chemical compound O1C2=C(C=O)C(O)=CC(C)=C2C(=O)OC2=C1C(C)=C(C(=O)OC)C(O)=C2C HTAATVDZOHXHBE-UHFFFAOYSA-N 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
230000002906 microbiologic effect Effects 0.000 description 2
210000004400 mucous membrane Anatomy 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000006395 oxidase reaction Methods 0.000 description 2
108040007629 peroxidase activity proteins Proteins 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
238000009491 slugging Methods 0.000 description 2
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
238000010792 warming Methods 0.000 description 2
239000001993 wax Substances 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
WDMUXYQIMRDWRC-UHFFFAOYSA-N 2-hydroxy-3,4-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O WDMUXYQIMRDWRC-UHFFFAOYSA-N 0.000 description 1
DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
QHRTZMDBPOUHPU-UHFFFAOYSA-N 4-(4-amino-3-methoxyphenyl)-2-methoxyaniline;hydrochloride Chemical compound Cl.C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 QHRTZMDBPOUHPU-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
102000006786 Chloride-Bicarbonate Antiporters Human genes 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
RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
241001269524 Dura Species 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
229920002527 Glycogen Polymers 0.000 description 1
101001091385 Homo sapiens Kallikrein-6 Proteins 0.000 description 1
241000243251 Hydra Species 0.000 description 1
229940124036 Hydrolase inhibitor Drugs 0.000 description 1
241000155250 Iole Species 0.000 description 1
244000017020 Ipomoea batatas Species 0.000 description 1
235000002678 Ipomoea batatas Nutrition 0.000 description 1
102100034866 Kallikrein-6 Human genes 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241000408529 Libra Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000353097 Molva molva Species 0.000 description 1
229920000715 Mucilage Polymers 0.000 description 1
101100459301 Mus musculus Myl4 gene Proteins 0.000 description 1
102100026367 Pancreatic alpha-amylase Human genes 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
101150104938 Pigl gene Proteins 0.000 description 1
241001237728 Precis Species 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
208000032827 Ring chromosome 9 syndrome Diseases 0.000 description 1
108091006259 SLC4A3 Proteins 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000024109 Spiris Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
101150057833 THEG gene Proteins 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
LUEWUZLMQUOBSB-UHFFFAOYSA-N UNPD55895 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(O)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O LUEWUZLMQUOBSB-UHFFFAOYSA-N 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
229960000583 acetic acid Drugs 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
108090000637 alpha-Amylases Proteins 0.000 description 1
BNABBHGYYMZMOA-AHIHXIOASA-N alpha-maltoheptaose 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]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O[C@@H]6[C@H](O[C@H](O)[C@H](O)[C@H]6O)CO)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O BNABBHGYYMZMOA-AHIHXIOASA-N 0.000 description 1
OCIBBXPLUVYKCH-QXVNYKTNSA-N alpha-maltohexaose 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]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O OCIBBXPLUVYKCH-QXVNYKTNSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
238000010923 batch production Methods 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000669 biting effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
230000023852 carbohydrate metabolic process Effects 0.000 description 1
235000021256 carbohydrate metabolism Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229940106135 cellulose Drugs 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
210000004913 chyme Anatomy 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000000567 combustion gas Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
208000002925 dental caries Diseases 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
JFUIHGAGFMFNRD-UHFFFAOYSA-N fica Chemical compound FC1=CC=C2NC(C(=O)NCCS)=CC2=C1 JFUIHGAGFMFNRD-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000000727 fraction Substances 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005640 glucopyranosyl group Chemical group 0.000 description 1
229930182478 glucoside Natural products 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
230000005484 gravity Effects 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
150000002402 hexoses Chemical group 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
239000004093 hydrolase inhibitor Substances 0.000 description 1
239000000413 hydrolysate Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003914 insulin secretion Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
DJMVHSOAUQHPSN-UHFFFAOYSA-N malto-hexaose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(OC4C(C(O)C(O)C(CO)O4)O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 DJMVHSOAUQHPSN-UHFFFAOYSA-N 0.000 description 1
UYQJCPNSAVWAFU-UHFFFAOYSA-N malto-tetraose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)O1 UYQJCPNSAVWAFU-UHFFFAOYSA-N 0.000 description 1
RUJILUJOOCOSRO-WJMYNTJYSA-N maltooctaose 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]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O[C@@H]6[C@H](O[C@H](O[C@@H]7[C@H](O[C@H](O)[C@H](O)[C@H]7O)CO)[C@H](O)[C@H]6O)CO)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O RUJILUJOOCOSRO-WJMYNTJYSA-N 0.000 description 1
LUEWUZLMQUOBSB-OUBHKODOSA-N maltotetraose 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]2[C@@H](O[C@@H](O[C@@H]3[C@@H](O[C@@H](O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-OUBHKODOSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000003471 mutagenic agent Substances 0.000 description 1
231100000707 mutagenic chemical Toxicity 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229940080469 phosphocellulose Drugs 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013573 potato product Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
235000002020 sage Nutrition 0.000 description 1
238000007789 sealing Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000011800 void material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside 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]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
General Health & Medical Sciences (AREA)
Zoology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Wood Science & Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Microbiology (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
General Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Enzymes And Modification Thereof (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)

CA209,484A 1973-09-22 1974-09-18 Glycoside amylase Expired CA1044164A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2347782A DE2347782C3 (de)	1973-09-22	1973-09-22	Aminozuckerderivate, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
CA1044164A true CA1044164A (fr)	1978-12-12

Family

ID=5893358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA209,484A Expired CA1044164A (fr)	1973-09-22	1974-09-18	Glycoside amylase

Country Status (28)

Country	Link
JP (2)	JPS5439474B2 (fr)
AR (1)	AR210988A1 (fr)
AT (1)	AT338199B (fr)
BE (1)	BE820147A (fr)
BG (1)	BG24959A3 (fr)
CA (1)	CA1044164A (fr)
CH (1)	CH596312A5 (fr)
CS (1)	CS200173B2 (fr)
DD (1)	DD117249A5 (fr)
DE (1)	DE2347782C3 (fr)
DK (1)	DK139979C (fr)
EG (1)	EG12207A (fr)
ES (1)	ES430283A1 (fr)
FI (1)	FI56698C (fr)
FR (1)	FR2244536B1 (fr)
GB (1)	GB1482543A (fr)
HK (1)	HK29780A (fr)
IE (1)	IE39856B1 (fr)
IL (1)	IL45685A (fr)
LU (2)	LU88274I2 (fr)
NL (2)	NL180941C (fr)
NO (1)	NO142755C (fr)
PH (1)	PH12530A (fr)
RO (1)	RO84246B (fr)
SE (1)	SE432111B (fr)
SU (1)	SU562202A3 (fr)
YU (1)	YU254574A (fr)
ZA (1)	ZA745972B (fr)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2614393C3 (de) *	1976-04-02	1980-04-03	Bayer Ag, 5090 Leverkusen	Aminozucker-Derivate und diese Verbindungen enthaltende Arzneimittel
US4175123A (en) *	1976-12-23	1979-11-20	Bayer Aktiengesellschaft	Amino-sugar derivatives, process for their preparation and pharmaceutical composition thereof
DE2719912C3 (de) *	1977-05-04	1979-12-06	Bayer Ag, 5090 Leverkusen	Verfahren zur Isolierung von 0- \|4,6-Dideoxy-4- [JJl S-O,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2cyclohexen-1-yl] -amino] - a -D-glucopyranosyl} -(I Pfeil nach rechts 4)-0- a D-glucopyranosyl-(l Pfeil nach rechts 4)-D-glucopyranose aus Kulturbrühen
JPS5953920B2 (ja) *	1977-12-28	1984-12-27	東洋醸造株式会社	新規なアミノ糖化合物およびその製法
GB2016497A (en) *	1978-02-10	1979-09-26	Taisho Pharmaceutical Co Ltd	Microbiological production of amylase inhibitor
CA1121290A (fr) *	1978-02-14	1982-04-06	Yasuji Suhara	Derives amines d'un sucre
DE3134591A1 (de) *	1981-09-01	1983-03-10	Bayer Ag, 5090 Leverkusen	Neue arzneimittelpraeparationen fuer glykosidhydrolasen-inhibitoren
DE3543999A1 (de) *	1985-12-13	1987-06-19	Bayer Ag	Hochreine acarbose
DE19507214A1 (de) *	1995-03-02	1996-10-31	Bayer Ag	Acarbose-Biosynthesegene aus Actinoplanes sp., Verfahren zu ihrer Isolierung sowie ihre Verwendung
EP0796915A3 (fr) *	1996-03-22	1999-04-14	Bayer Ag	Procédé de préparation et utilisation d'acarviosyl-transferase dans la conversion d'homologues d'acarbose et dans la préparation d'homologues d'acarbose
DE19637591A1 (de) *	1996-09-13	1998-03-19	Bayer Ag	Osmokontrolliertes Fermentationsverfahren zur Herstellung von Acarbose
IT1293819B1 (it) *	1997-08-05	1999-03-10	Univ Massachusetts Lowell	Procedimento per la preparazione di acarbosio
DE19844924A1 (de) *	1998-09-30	2000-04-06	Bayer Ag	Immobilisierte Zellen von Actinoplanes acarbosefaciens SE 50/110, Immobilisierungsverfahren und Verwendung des Immobilisats zur Herstellung von Acarbose
US7022684B2 (en)	2000-05-24	2006-04-04	Pfizer Inc.	Treatment of rumen acidosis with α-amylase inhibitors
HRP20010792A2 (en)	2001-10-26	2003-04-30	Pliva D D	Acarbose purification process
EP2145538A1 (fr)	2008-07-15	2010-01-20	Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts	Produit de protection des plantes et des matériaux
TR201100148A2 (tr)	2011-01-06	2012-07-23	Bi̇lgi̇ç Mahmut	Stabil akarboz förmülasyonları.
TR201100150A2 (tr)	2011-01-06	2012-07-23	Bi̇lgi̇ç Mahmut	Suda çözünür dozaj formları
WO2013083566A1 (fr)	2011-12-08	2013-06-13	Bayer Intellectual Property Gmbh	Nouvel élément actinomycète d'intégration et de conjugaison provenant d'actinoplanes sp. se50/110 en tant que plasmide pour la transformation génétique d'actinobactéries associées
WO2013115738A1 (fr)	2012-01-31	2013-08-08	Mahmut Bilgic	Acarbose micronisée
EP2774619B1 (fr)	2013-03-04	2016-05-18	BioActive Food GmbH	Composition pour le traitement de pathologies hyperglycémiques
EP2944311A1 (fr)	2014-05-16	2015-11-18	BioActive Food GmbH	Combinaison de substances biologiques actives destinée au traitement de pathologies hypoglycémiques

1973
- 1973-09-22 DE DE2347782A patent/DE2347782C3/de not_active Expired
1974
- 1974-09-06 NO NO74743210A patent/NO142755C/no unknown
- 1974-09-16 PH PH16285A patent/PH12530A/en unknown
- 1974-09-18 CH CH1264974A patent/CH596312A5/xx not_active IP Right Cessation
- 1974-09-18 CA CA209,484A patent/CA1044164A/fr not_active Expired
- 1974-09-18 SE SE7411748A patent/SE432111B/xx active Protection Beyond IP Right Term
- 1974-09-18 BG BG027718A patent/BG24959A3/xx unknown
- 1974-09-19 FI FI2740/74A patent/FI56698C/fi active
- 1974-09-19 AR AR255651A patent/AR210988A1/es active
- 1974-09-19 YU YU02545/74A patent/YU254574A/xx unknown
- 1974-09-19 JP JP10721674A patent/JPS5439474B2/ja not_active Expired
- 1974-09-20 AT AT757974A patent/AT338199B/de active Protection Beyond IP Right Term
- 1974-09-20 LU LU88274C patent/LU88274I2/xx unknown
- 1974-09-20 DD DD181235A patent/DD117249A5/xx unknown
- 1974-09-20 ZA ZA00745972A patent/ZA745972B/xx unknown
- 1974-09-20 NL NLAANVRAGE7412478,A patent/NL180941C/xx not_active IP Right Cessation
- 1974-09-20 GB GB41073/74A patent/GB1482543A/en not_active Expired
- 1974-09-20 LU LU70953A patent/LU70953A1/xx active Protection Beyond IP Right Term
- 1974-09-20 DK DK497374A patent/DK139979C/da active
- 1974-09-20 IE IE1946/74A patent/IE39856B1/xx unknown
- 1974-09-20 BE BE148729A patent/BE820147A/fr not_active IP Right Cessation
- 1974-09-20 SU SU2063266A patent/SU562202A3/ru active
- 1974-09-20 CS CS746498A patent/CS200173B2/cs unknown
- 1974-09-20 FR FR7431906A patent/FR2244536B1/fr not_active Expired
- 1974-09-20 IL IL7445685A patent/IL45685A/xx unknown
- 1974-09-21 EG EG411/74A patent/EG12207A/xx active
- 1974-09-21 ES ES430283A patent/ES430283A1/es not_active Expired
- 1974-09-21 RO RO80038A patent/RO84246B/ro unknown
1979
- 1979-07-20 JP JP9174679A patent/JPS5536479A/ja active Granted
1980
- 1980-05-29 HK HK297/80A patent/HK29780A/xx unknown
1993
- 1993-05-24 NL NL930036C patent/NL930036I2/nl unknown

Also Published As

Publication number	Publication date
SU562202A3 (ru)	1977-06-15
NL930036I2 (nl)	1993-10-01
DD117249A5 (fr)	1976-01-05
JPS5648518B2 (fr)	1981-11-16
IE39856B1 (en)	1979-01-17
FI274074A7 (fr)	1975-03-23
NO743210L (fr)	1975-04-21
CH596312A5 (fr)	1978-03-15
CS200173B2 (en)	1980-08-29
PH12530A (en)	1979-05-17
IL45685A (en)	1979-05-31
IE39856L (en)	1975-03-22
SE432111B (sv)	1984-03-19
FI56698C (fi)	1980-03-10
NO142755B (no)	1980-06-30
AR210988A1 (es)	1977-10-14
RO84246A (fr)	1984-05-23
DK139979C (da)	1979-10-29
NL180941C (nl)	1987-05-18
NL930036I1 (nl)	1993-08-02
DE2347782C3 (de)	1979-10-11
FR2244536A1 (fr)	1975-04-18
DK497374A (fr)	1975-06-02
DE2347782B2 (de)	1979-02-15
YU254574A (en)	1982-02-28
AU7350374A (en)	1976-03-25
NO142755C (no)	1980-10-08
LU88274I2 (fr)	1994-02-03
NL7412478A (nl)	1975-03-25
GB1482543A (en)	1977-08-10
NL180941B (nl)	1986-12-16
ES430283A1 (es)	1976-12-16
ATA757974A (de)	1976-12-15
JPS5536479A (en)	1980-03-14
FI56698B (fi)	1979-11-30
JPS5053593A (fr)	1975-05-12
RO84246B (ro)	1984-07-30
BE820147A (fr)	1975-03-20
ZA745972B (en)	1975-10-29
HK29780A (en)	1980-06-06
LU70953A1 (fr)	1975-05-28
BG24959A3 (bg)	1978-06-15
AT338199B (de)	1977-08-10
EG12207A (en)	1979-03-31
JPS5439474B2 (fr)	1979-11-28
IL45685A0 (en)	1974-11-29
FR2244536B1 (fr)	1978-07-28
DK139979B (da)	1979-05-28
SE7411748L (fr)	1975-03-24
DE2347782A1 (de)	1975-04-10

Publication	Publication Date	Title
US4062950A (en)	1977-12-13	Amino sugar derivatives
CA1121290A (fr)	1982-04-06	Derives amines d'un sucre
SU562202A3 (ru)	1977-06-15	Способ получени производных аминосахаров
US4019960A (en)	1977-04-26	Process for the production of a saccharase inhibitor
US4307194A (en)	1981-12-22	Inhibitors, obtained from bacilli, for glycoside hydrolases
US4316894A (en)	1982-02-23	Antibiotic SF-1130-x3 3 substance and production and use thereof
RU2134694C1 (ru)	1999-08-20	Аминоолигосахарид ск-4416, способ его получения, ингибитор сахаридгидролазы и антибактериальный агент
US3937817A (en)	1976-02-10	Pharmaceutical compositions containing a saccharase inhibitor
US4618602A (en)	1986-10-21	Amine containing pseudooligosaccharide, pharmaceutical composition and method of use
CH633043A5 (en)	1982-11-15	Process for preparing aminosugar derivatives
US4632917A (en)	1986-12-30	Pseudooligosaccharides with an α-glucosidase-inhibiting action, their use and pharmaceutical products
PL91664B1 (fr)	1977-03-31
US3934006A (en)	1976-01-20	Pharmaceutical compositions comprising saccharase inhibitors
EP0560982A1 (fr)	1993-09-22	Procede de production de sucre et transfusion
US4990500A (en)	1991-02-05	Oxirane pseudooligosaccharides, a process for their preparation, their use and pharmaceutical preparations
KR790001709B1 (ko)	1979-12-14	아미노-슈가 화합물의 제조방법
Pfeffer et al.	1986	Prefeeding-dependent anaerobic metabolization of xenobiotics by intestinal bacteria—methods for acarbose metabolites in an artificial colon
US4197292A (en)	1980-04-08	Novel amylase inhibitors
US3995026A (en)	1976-11-30	Amylase inhibitor
EP0808843B1 (fr)	2003-03-26	Composé macrolide 0406
FI63964C (fi)	1983-09-12	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara aminosockerderivat
IE44803B1 (en)	1982-04-07	Amino-sugar derivatives
KR830001068B1 (ko)	1983-06-01	아미노당 유도체의 제조방법
KR800001434B1 (ko)	1980-12-07	아미노-당 유도체의 제조방법
JPS58172400A (ja)	1983-10-11	新規なアミノオリゴ糖誘導体