NO162387B - Analogifremgangsmaate ved fremstilling av terapeutisk aktive homodisaccharider. - Google Patents

Analogifremgangsmaate ved fremstilling av terapeutisk aktive homodisaccharider. Download PDF

Info

Publication number: NO162387B
Authority: NO; Norway
Prior art keywords: dideoxy; heptitol; glycero; gulo; imino
Prior art date: 1984-12-18

Application number

NO855087A

Other languages

English (en)

Norwegian (no)

Other versions

NO855087L (no

Inventor

Paul S Liu

Original Assignee

Merrell Dow Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-12-18

Filing date

1985-12-17

Publication date

1989-09-11

1985-12-17 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1986-06-19 Publication of NO855087L publication Critical patent/NO855087L/no

1989-09-11 Publication of NO162387B publication Critical patent/NO162387B/no

Links

238000000034 method Methods 0.000 title claims description 20
230000001225 therapeutic effect Effects 0.000 title 1
-1 Homonojirimycin glycosides Chemical class 0.000 claims abstract description 27
150000001875 compounds Chemical class 0.000 claims abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
150000002148 esters Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 3
WXYNLXPSTFTJJC-RUOAZZEASA-N (2r,3r,4s,5r,6r)-2-bromo-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane Chemical compound C([C@H]1O[C@@H]([C@@H]([C@@H](OCC=2C=CC=CC=2)[C@@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)Br)OCC1=CC=CC=C1 WXYNLXPSTFTJJC-RUOAZZEASA-N 0.000 claims description 2
VPQUKCWUGUDXRY-AKIKKLFKSA-N 1-hydroxy-1-[(2r,3r,4s,5s,6r)-3,4,5-triacetyl-6-bromo-3,4,5-trihydroxyoxan-2-yl]propan-2-one Chemical compound CC(=O)C(O)[C@H]1O[C@H](Br)[C@@](O)(C(C)=O)[C@](O)(C(C)=O)[C@@]1(O)C(C)=O VPQUKCWUGUDXRY-AKIKKLFKSA-N 0.000 claims description 2
125000000824 D-ribofuranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 2
125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 2
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims description 2
KEPRGMVNSZCFER-DGORSVRFSA-N C[C@@H]1[C@]([C@]([C@@]([C@H](O1)Cl)(C(=O)C)O)(C(=O)C)O)(C(=O)C)O Chemical compound C[C@@H]1[C@]([C@]([C@@]([C@H](O1)Cl)(C(=O)C)O)(C(=O)C)O)(C(=O)C)O KEPRGMVNSZCFER-DGORSVRFSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
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 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
150000001720 carbohydrates Chemical class 0.000 abstract description 5
239000003112 inhibitor Substances 0.000 abstract description 3
125000006239 protecting group Chemical group 0.000 abstract description 3
CLVUFWXGNIFGNC-QTSLKERKSA-N (2r,3s,5r,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol Chemical compound OC[C@H]1N[C@H](CO)[C@H](O)C(O)[C@@H]1O CLVUFWXGNIFGNC-QTSLKERKSA-N 0.000 abstract description 2
229930182470 glycoside Natural products 0.000 abstract description 2
102000038379 digestive enzymes Human genes 0.000 abstract 1
108091007734 digestive enzymes Proteins 0.000 abstract 1
239000000243 solution Substances 0.000 description 37
239000000203 mixture Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
239000002904 solvent Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 14
239000008103 glucose Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000008280 blood Substances 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
239000012267 brine Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
239000006188 syrup Substances 0.000 description 8
235000020357 syrup Nutrition 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
239000008107 starch Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 4
235000014633 carbohydrates Nutrition 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000012156 elution solvent Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
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 3
229960000583 acetic acid Drugs 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 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
238000006264 debenzylation reaction Methods 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
125000003147 glycosyl group Chemical group 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
150000002730 mercury Chemical class 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
230000006377 glucose transport Effects 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
229940075610 mercuric cyanide Drugs 0.000 description 2
NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
239000011343 solid material Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
OGOMAWHSXRDAKZ-BKJHVTENSA-N (3r,4s,5r,6r)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol Chemical compound C([C@H]1OC([C@@H]([C@@H](OCC=2C=CC=CC=2)[C@@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)O)OCC1=CC=CC=C1 OGOMAWHSXRDAKZ-BKJHVTENSA-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
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
102000005744 Glycoside Hydrolases Human genes 0.000 description 1
108010031186 Glycoside Hydrolases Proteins 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920003091 Methocel™ Polymers 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical class OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 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
229960004909 aminosalicylic acid Drugs 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
238000011068 loading method Methods 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
235000012054 meals Nutrition 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229940100892 mercury compound Drugs 0.000 description 1
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(II) oxide Inorganic materials [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 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
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000009738 saturating Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
- 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
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Medicines Containing Plant Substances (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Luminescent Compositions (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO855087A 1984-12-18 1985-12-17 Analogifremgangsmaate ved fremstilling av terapeutisk aktive homodisaccharider. NO162387B (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/683,127 US4634765A (en)	1984-12-18	1984-12-18	Homodisaccharide hypoglycemic agents

Publications (2)

Publication Number	Publication Date
NO855087L NO855087L (no)	1986-06-19
NO162387B true NO162387B (no)	1989-09-11

Family

ID=24742682

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO855087A NO162387B (no)	1984-12-18	1985-12-17	Analogifremgangsmaate ved fremstilling av terapeutisk aktive homodisaccharider.

Country Status (20)

Country	Link
US (1)	US4634765A (fr)
EP (1)	EP0186103B1 (fr)
JP (1)	JPS61158994A (fr)
KR (1)	KR900005607B1 (fr)
CN (1)	CN1016784B (fr)
AT (1)	ATE62249T1 (fr)
AU (1)	AU574246B2 (fr)
CA (1)	CA1240989A (fr)
DE (1)	DE3582420D1 (fr)
DK (1)	DK587085A (fr)
ES (1)	ES8706164A1 (fr)
FI (1)	FI80707C (fr)
GR (1)	GR853032B (fr)
HU (1)	HU194263B (fr)
IE (1)	IE58186B1 (fr)
NO (1)	NO162387B (fr)
NZ (1)	NZ214570A (fr)
PH (1)	PH23660A (fr)
PT (1)	PT81689B (fr)
ZA (1)	ZA859573B (fr)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2181729B (en) *	1985-10-12	1990-04-04	Nippon Shinyaku Co Ltd	Glucosylmoranoline derivatives and production thereof
JPS62242692A (ja) *	1986-04-15	1987-10-23	Nippon Shinyaku Co Ltd	モラノリン誘導体の製造法
EP0344383A1 (fr) *	1988-06-02	1989-12-06	Merrell Dow Pharmaceuticals Inc.	Inhibiteurs d'alpha-glucosidase
EP0345104B1 (fr) *	1988-06-02	1995-11-02	Merrell Dow Pharmaceuticals Inc.	Inhibiteurs d'alpha-glucosidase
US4880917A (en) *	1988-07-01	1989-11-14	Merrell Dow Pharmaceuticals Inc.	Process for hydrolyzing 2,6-dideoxy-2,6-iminoheptononitrile derivatives using trifluoroacetic acid and dinitrogen tetroxide
US4908439A (en) *	1988-09-16	1990-03-13	Merrell Dow Pharmaceuticals Inc.	Synthesis of intermediate useful in the preparation of nojirimycin and related compounds
US5227479A (en) *	1989-12-20	1993-07-13	Merrell Dow Pharmaceuticals Inc.	Process for the preparation of nojirimycin and related compounds
US5504078A (en) *	1990-06-08	1996-04-02	Merrell Dow Pharmaceuticals Inc.	α-glucosidase inhibitors
ATE422359T1 (de) *	1997-04-15	2009-02-15	Csir	Verbindungen und pharmazeutische zusammensetzungen mit appetitunterdrückender aktivität
GB2396815B (en) *	1999-10-27	2004-09-08	Phytopharm Plc	A composition comprising a pregnenone derivative and an NSAID
EP1181277A4 (fr)	2000-03-31	2005-08-10	Univ Michigan State	Procede de preparation de 1,5-didesoxy-1,5-imino hexitols a partir d'oximes ou d'imines
GB2363985B (en)	2000-06-30	2004-09-29	Phytopharm Plc	Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use
US7262318B2 (en) *	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
AU2005308575A1 (en) *	2004-11-23	2006-06-01	Warner-Lambert Company Llc	7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as HMG Co-A reductase inhibitors for the treatment of lipidemia
WO2006133447A1 (fr) *	2005-06-08	2006-12-14	Amicus Therapeutics, Inc.	Compositions de sucre cristallin et procede de production associe
US20060293508A1 (en) *	2005-06-08	2006-12-28	Michael Major	Stabilization of triflated compounds
US7973157B2 (en) *	2005-06-08	2011-07-05	Amicus Therapeutics, Inc.	Imino and amino sugar purification
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
JP5498168B2 (ja)	2006-12-01	2014-05-21	ブリストル−マイヤーズスクイブカンパニー	アテローム性動脈硬化および循環器疾患の治療のためのｃｅｔｐ阻害剤としてのｎ−（（３−ベンジル）−２，２−（ビス−フェニル）−プロパン−１−アミン誘導体
ATE518544T1 (de)	2007-03-12	2011-08-15	Zadec Aps	Rotbusch-extrakt gegen diabetes
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
MX2009013293A (es)	2007-06-04	2010-02-15	Synergy Pharmaceuticals Inc	Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos.
EP2810951B1 (fr)	2008-06-04	2017-03-15	Synergy Pharmaceuticals Inc.	Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles
CA2730603C (fr)	2008-07-16	2019-09-24	Synergy Pharmaceuticals Inc.	Agonistes de la guanylate cyclase utiles dans le traitement des affections gastro-intestinales, de l'inflammation gastro-intestinale, du cancer gastro-intestinal et d'autres affections
CA2799708A1 (fr)	2010-05-21	2011-11-24	Pfizer Inc.	2-phenylbenzoylamides
US20130156720A1 (en)	2010-08-27	2013-06-20	Ironwood Pharmaceuticals, Inc.	Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
CN102462726B (zh) *	2010-11-04	2016-03-09	中国医学科学院药物研究所	白树总生物碱及多羟基生物碱化合物的提取、分离及用途
CA2828343A1 (fr)	2011-03-04	2012-09-13	The Scripps Research Institute	Peptides de type edn3 et utilisations associees
US20140323705A1 (en) *	2011-05-13	2014-10-30	Markus Hederos	Manufacture of lacto-n-tetraose
MY188344A (en)	2012-03-09	2021-12-01	Biotropics Malaysia Berhad	Extract formulations of rhodamnia cinerea and uses thereof
JP2016514671A (ja)	2013-03-15	2016-05-23	シナジーファーマシューティカルズインコーポレイテッド	グアニル酸シクラーゼのアゴニストおよびその使用
JP2016514670A (ja)	2013-03-15	2016-05-23	シナジーファーマシューティカルズインコーポレイテッド	他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト
SG11201507496UA (en)	2013-04-17	2015-11-27	Pfizer	N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases
EA201592263A1 (ru)	2013-06-05	2016-05-31	Синерджи Фармасьютикалз, Инк.	Ультрачистые агонисты гуанилатциклазы c, способ их получения и использования
EP3186242B1 (fr)	2014-08-29	2021-10-06	Tes Pharma S.r.l.	Inhibiteurs de la semialdéhyde décarboxylase de l'acide alpha-amino-bêta-carboxymuconique
WO2016055901A1 (fr)	2014-10-08	2016-04-14	Pfizer Inc.	Composés d'amide substitué
CN104530150A (zh) *	2015-01-14	2015-04-22	佛山市赛维斯医药科技有限公司	含胺基苯和双葡萄糖苷结构化合物、其制备方法和用途
AU2017342083A1 (en)	2016-10-14	2019-04-11	Tes Pharma S.R.L.	Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase
IT201700078102A1 (it)	2017-07-11	2019-01-11	Dipharma Francis Srl	Sintesi di un azazucchero e suoi intermedi
CN108828121B (zh) *	2018-06-14	2020-06-05	华润三九医药股份有限公司	一种白树药材中α-高野尻霉素的含量检测方法
AR117122A1 (es)	2018-11-20	2021-07-14	Tes Pharma S R L	INHIBIDORES DE LA ÁCIDO a-AMINO-b-CARBOXIMUCÓNICO SEMIALDEHÍDO DESCARBOXILASA
US11248001B2 (en)	2019-01-18	2022-02-15	Astrazeneca Ab	PCSK9 inhibitors and methods of use thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4065562A (en) *	1975-12-29	1977-12-27	Nippon Shinyaku Co., Ltd.	Method and composition for reducing blood glucose levels
NO154918C (no) *	1977-08-27	1987-01-14	Bayer Ag	Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
DE2848117A1 (de) *	1978-11-06	1980-05-14	Bayer Ag	Derivate des 2-hydroxymethyl-3,4,5- trihydroxy-piperidins, ihre herstellung und verwendung zur beeinflussung des kohlenhydrat- und fettstoffwechsels
DE2942365A1 (de) *	1979-10-19	1981-05-14	Bayer Ag, 5090 Leverkusen	2-hydroxyalkyl-3,4,5-trihydroxy-(pi)-peridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
GB2064527B (en) *	1979-12-08	1984-05-02	Nippon Shinyaku Co Ltd	Moranoline derivatives and process for preparation thereof
IT1210476B (it) *	1981-05-28	1989-09-14	Erba Farmitalia	Antracicline.

1984
- 1984-12-18 US US06/683,127 patent/US4634765A/en not_active Expired - Lifetime
1985
- 1985-12-05 AU AU50810/85A patent/AU574246B2/en not_active Ceased
- 1985-12-13 CA CA000497607A patent/CA1240989A/fr not_active Expired
- 1985-12-13 ZA ZA859573A patent/ZA859573B/xx unknown
- 1985-12-13 FI FI854944A patent/FI80707C/fi not_active IP Right Cessation
- 1985-12-16 PT PT81689A patent/PT81689B/pt not_active IP Right Cessation
- 1985-12-16 NZ NZ214570A patent/NZ214570A/en unknown
- 1985-12-16 IE IE317985A patent/IE58186B1/en not_active IP Right Cessation
- 1985-12-16 HU HU854804A patent/HU194263B/hu not_active IP Right Cessation
- 1985-12-17 ES ES550060A patent/ES8706164A1/es not_active Expired
- 1985-12-17 CN CN85109548A patent/CN1016784B/zh not_active Expired
- 1985-12-17 AT AT85116117T patent/ATE62249T1/de not_active IP Right Cessation
- 1985-12-17 EP EP85116117A patent/EP0186103B1/fr not_active Expired - Lifetime
- 1985-12-17 JP JP60282167A patent/JPS61158994A/ja active Granted
- 1985-12-17 DK DK587085A patent/DK587085A/da not_active Application Discontinuation
- 1985-12-17 NO NO855087A patent/NO162387B/no unknown
- 1985-12-17 DE DE8585116117T patent/DE3582420D1/de not_active Expired - Fee Related
- 1985-12-17 GR GR853032A patent/GR853032B/el unknown
- 1985-12-18 PH PH33204A patent/PH23660A/en unknown
- 1985-12-18 KR KR1019850009529A patent/KR900005607B1/ko not_active Expired

Also Published As

Publication number	Publication date
CA1240989A (fr)	1988-08-23
PT81689A (en)	1986-01-01
FI854944A0 (fi)	1985-12-13
DK587085A (da)	1986-06-19
KR860004921A (ko)	1986-07-16
FI854944L (fi)	1986-06-19
FI80707B (fi)	1990-03-30
CN85109548A (zh)	1986-07-09
EP0186103A2 (fr)	1986-07-02
NZ214570A (en)	1988-03-30
PT81689B (pt)	1987-11-30
FI80707C (fi)	1990-07-10
JPH0565519B2 (fr)	1993-09-17
ES8706164A1 (es)	1987-06-01
DE3582420D1 (de)	1991-05-08
US4634765A (en)	1987-01-06
PH23660A (en)	1989-09-27
JPS61158994A (ja)	1986-07-18
EP0186103A3 (en)	1988-02-03
CN1016784B (zh)	1992-05-27
AU5081085A (en)	1986-06-26
IE853179L (en)	1986-06-18
NO855087L (no)	1986-06-19
HU194263B (en)	1988-01-28
DK587085D0 (da)	1985-12-17
GR853032B (fr)	1986-04-18
ZA859573B (en)	1986-08-27
ES550060A0 (es)	1987-06-01
KR900005607B1 (ko)	1990-07-31
AU574246B2 (en)	1988-06-30
IE58186B1 (en)	1993-07-28
EP0186103B1 (fr)	1991-04-03
ATE62249T1 (de)	1991-04-15
HUT40137A (en)	1986-11-28

Publication	Publication Date	Title
EP0186103B1 (fr)	1991-04-03	Agents hypoglycémiques du type homodisaccharide
US3699103A (en)	1972-10-17	Process for the manufacture of 5-desoxy-l-arabinose and novel intermediates
Blériot et al.	2002	Synthesis of seven-and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases
Brown et al.	2000	A Simple Synthesis of Morphine-3, 6-di-β-d-glucuronide
Hendry et al.	1988	Enantiospecific synthesis of polyhydroxylated indolizidines related to castanospermine: 1 1-deoxy-castanospermine.
SATO et al.	1987	Synthesis of 2-(5-cholesten-3β-yloxy) glycosides of N-acetyl-D-neuraminic acid derivatives
NO170687B (no)	1992-08-10	Analogifremgangsmaate til fremstilling av fluorsubstituerte 4'-demetylepipodofyllotoksin-glukosider
US4839346A (en)	1989-06-13	Antitumor anthracycline glycosides, intermediates thereof, and composition and use thereof
Knapp et al.	1986	Synthesis of (-)-methyl ravidosaminide
US5286877A (en)	1994-02-15	Synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol
JPH0660191B2 (ja)	1994-08-10	新規アントラサイクリングリコシド類，それらの製造方法及びそれらを含む抗腫瘍剤
US4001402A (en)	1977-01-04	Cardenolide glycosides and method of making the same, and therapeutic composition
Hendry et al.	1988	Enantiospecific synthesis of polhydroxylated indolizidines related to castanospermine: 1 (6R, 7S, 8aR)-6, 7-dihydroxyindolizidine and (6R, 7R, 8S, 8aR)-6, 7, 8-trihydroxyindolizidine.
EP1829884B1 (fr)	2010-11-10	Sucre-donneur
Ogawa et al.	1999	Synthesis of Ether‐and Imino‐Linked Octyl N‐Acetyl‐5a′‐carba‐β‐lactosaminides and‐isolactosaminides: Acceptor Substrates for α‐(1→ 3/4)‐Fucosyltransferase, and Enzymatic Synthesis of 5a′‐Carbatrisaccharides
US5028614A (en)	1991-07-02	Hydroxymethyl-indolizidines and quinolizidines and their use as α-glucosidase I inhibitors
EP0457215B1 (fr)	1996-01-17	3'-Déamino-4'-déoxy-4'-amino-8-fluoroanthracyclines et leurs procédés de préparation
Popsavin et al.	1999	Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1, 2-anhydride
NESS et al.	1961	2-Deoxy-D-ribose. VII. 1 Crystalline 2-Deoxy-3, 5-di-Op-nitrobenzoyl-D-ribosyl Chloride and Related Derivatives
NO115023B (fr)	1968-07-08
Sakakibara et al.	1987	Preparation and structural determination of methyl 4, 6-O-benzylidene-2, 3-dideoxy-β-d-erythro-hexopyranosid [2, 3-d] triazole and of its adducts with 3-nitrohex-2-enopyranosides
JPH04316593A (ja)	1992-11-06	Ｄ−アロサンの製造方法
JPH02121999A (ja)	1990-05-09	ノジリマイシン及び関連化合物の製造に於けるのに有用な中間体の合成
Takahashi et al.	1994	Facile Preparation of a Phenyl l-Thioglycoside of Allopyranosylallopyranose from Allyl N, N'-Diacetylchitobioside.
JPS62155291A (ja)	1987-07-10	３−アミノ−４，５−ジヒドロキシピペリジン類、それらの製造方法及びそれらの使用