NO326965B1 - a-form eller β-form-krystall av acetanilid-derivat og farmasoytisk preparat - Google Patents
a-form eller β-form-krystall av acetanilid-derivat og farmasoytisk preparat Download PDFInfo
- Publication number
- NO326965B1 NO326965B1 NO20042227A NO20042227A NO326965B1 NO 326965 B1 NO326965 B1 NO 326965B1 NO 20042227 A NO20042227 A NO 20042227A NO 20042227 A NO20042227 A NO 20042227A NO 326965 B1 NO326965 B1 NO 326965B1
- Authority
- NO
- Norway
- Prior art keywords
- crystal
- form crystal
- ethyl
- amino
- hydroxy
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims description 130
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 3
- 150000008061 acetanilides Chemical class 0.000 title 1
- PBAPPPCECJKMCM-IBGZPJMESA-N mirabegron Chemical compound S1C(N)=NC(CC(=O)NC=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 PBAPPPCECJKMCM-IBGZPJMESA-N 0.000 claims description 27
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 16
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000010586 diagram Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- WSYDYHKUJOXZMK-TXEPZDRESA-N 2-(2-amino-1,3-thiazol-4-yl)-n-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide;dihydrochloride Chemical compound Cl.Cl.S1C(N)=NC(CC(=O)NC=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 WSYDYHKUJOXZMK-TXEPZDRESA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QILVTBCJVNFIDP-NTISSMGPSA-N (1r)-2-[2-(4-aminophenyl)ethylamino]-1-phenylethanol;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 QILVTBCJVNFIDP-NTISSMGPSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 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
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 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
- 239000002904 solvent Substances 0.000 description 4
- 238000002076 thermal analysis method Methods 0.000 description 4
- LUAUJCGKCGBAKA-NTISSMGPSA-N (1r)-2-[2-(4-nitrophenyl)ethylamino]-1-phenylethanol;hydrochloride Chemical compound Cl.C([C@H](O)C=1C=CC=CC=1)NCCC1=CC=C([N+]([O-])=O)C=C1 LUAUJCGKCGBAKA-NTISSMGPSA-N 0.000 description 3
- YWGDTDSOHPHFAQ-OAHLLOKOSA-N (2r)-2-hydroxy-n-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide Chemical compound O=C([C@H](O)C=1C=CC=CC=1)NCCC1=CC=C([N+]([O-])=O)C=C1 YWGDTDSOHPHFAQ-OAHLLOKOSA-N 0.000 description 3
- DYCLHZPOADTVKK-UHFFFAOYSA-N 2-(2-azaniumyl-1,3-thiazol-4-yl)acetate Chemical compound NC1=NC(CC(O)=O)=CS1 DYCLHZPOADTVKK-UHFFFAOYSA-N 0.000 description 3
- -1 2-hydroxy-2-phenylethyl Chemical group 0.000 description 3
- 206010022489 Insulin Resistance Diseases 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 230000003579 anti-obesity Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 201000005577 familial hyperlipidemia Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVMHULJEYUQYSH-UHFFFAOYSA-N 2-(4-nitrophenyl)ethylazanium;chloride Chemical compound Cl.NCCC1=CC=C([N+]([O-])=O)C=C1 JVMHULJEYUQYSH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001332914 | 2001-10-30 | ||
PCT/JP2002/011217 WO2003037881A1 (fr) | 2001-10-30 | 2002-10-29 | Cristal a forme $g(a) ou $g(b) d'un derive acetanilinide |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20042227L NO20042227L (no) | 2004-05-28 |
NO326965B1 true NO326965B1 (no) | 2009-03-23 |
Family
ID=19148268
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20042227A NO326965B1 (no) | 2001-10-30 | 2004-05-28 | a-form eller β-form-krystall av acetanilid-derivat og farmasoytisk preparat |
Country Status (17)
Country | Link |
---|---|
US (2) | US7342117B2 (de) |
EP (3) | EP1440969A4 (de) |
JP (1) | JP3800220B2 (de) |
KR (1) | KR100908796B1 (de) |
CN (1) | CN1243740C (de) |
AU (1) | AU2002344419C1 (de) |
BR (1) | BRPI0213570B8 (de) |
CA (1) | CA2464068C (de) |
ES (1) | ES2404071T3 (de) |
HU (1) | HU230481B1 (de) |
MX (1) | MXPA04003936A (de) |
NO (1) | NO326965B1 (de) |
PL (1) | PL218982B1 (de) |
RU (1) | RU2303033C2 (de) |
TW (1) | TW200300020A (de) |
WO (1) | WO2003037881A1 (de) |
ZA (1) | ZA200403044B (de) |
Families Citing this family (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7342117B2 (en) * | 2001-10-30 | 2008-03-11 | Astellas Pharma Inc. | α-form or β-form crystal of acetanilide derivative |
ZA200503510B (en) | 2002-11-07 | 2006-12-27 | Yamanouchi Pharma Co Ltd | Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
WO2005097127A2 (en) | 2004-04-02 | 2005-10-20 | Merck & Co., Inc. | Method of treating men with metabolic and anthropometric disorders |
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 |
AU2008261102B2 (en) | 2007-06-04 | 2013-11-28 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
EP2216021B1 (de) | 2007-11-02 | 2012-10-17 | Astellas Pharma Inc. | Pharmazeutische zusammensetzung zur behandlung von blasenhyperaktivität |
EP2328910B1 (de) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Für die behandlung von gastrointestinalen erkrankungen, entzündungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase |
EP3241839B1 (de) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Zur behandlung von erkrankungen des magen-darm-trakts, entzündlichen erkrankungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase |
TWI478712B (zh) | 2008-09-30 | 2015-04-01 | Astellas Pharma Inc | 釋控性醫藥組成物 |
MX2011004258A (es) | 2008-10-22 | 2011-06-01 | Merck Sharp & Dohme | Derivados de bencimidazol ciclicos novedosos utiles como agentes anti-diabeticos. |
EP2362731B1 (de) | 2008-10-31 | 2016-04-06 | Merck Sharp & Dohme Corp. | Neue nützlich anti-diabetische mittel mit zyklische benzimidazol-derivate |
US8586760B2 (en) | 2009-06-15 | 2013-11-19 | Auspex Pharmaceuticals, Inc. | Aminothiazole modulators of beta-3-adrenoreceptor |
WO2011106273A1 (en) | 2010-02-25 | 2011-09-01 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2011122524A1 (ja) * | 2010-03-29 | 2011-10-06 | アステラス製薬株式会社 | 放出制御医薬組成物 |
PE20130283A1 (es) * | 2010-06-16 | 2013-03-25 | Takeda Pharmaceutical | Cristal de compuesto de amida |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
WO2012116145A1 (en) | 2011-02-25 | 2012-08-30 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
US9283210B2 (en) * | 2011-05-18 | 2016-03-15 | Dr. Reddy's Laboratories Ltd. | Amorphous mirabegron and processes for crystal forms of mirabegron |
US9655885B2 (en) | 2011-05-18 | 2017-05-23 | Dr. Reddy's Laboratories Ltd. | Amorphous mirabegron and processes for crystal forms of mirabegron |
JPWO2013147134A1 (ja) | 2012-03-30 | 2015-12-14 | アステラス製薬株式会社 | ミラベグロン含有医薬組成物 |
CN103387500A (zh) * | 2012-05-11 | 2013-11-13 | 上海医药工业研究院 | 一种米拉贝隆及其中间体的制备方法 |
JP2015525782A (ja) | 2012-08-02 | 2015-09-07 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | 抗糖尿病性三環式化合物 |
KR20150045500A (ko) | 2012-08-31 | 2015-04-28 | 아스텔라스세이야쿠 가부시키가이샤 | 경구 투여용 의약 조성물 |
CN104994848A (zh) | 2013-02-22 | 2015-10-21 | 默沙东公司 | 抗糖尿病二环化合物 |
WO2014132270A2 (en) * | 2013-02-27 | 2014-09-04 | Msn Laboratories Limited | Process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-{[(2r)-2-hydroxy-2-phenyl ethyl]amino}ethyl)phenyl]acetamide monohydrochloride, its intermediates and polymorph thereof |
US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
CN103193730A (zh) * | 2013-04-17 | 2013-07-10 | 苏州永健生物医药有限公司 | 一种米拉贝隆的合成方法 |
CN103232368B (zh) * | 2013-04-18 | 2015-08-12 | 苏州永健生物医药有限公司 | 一种(r)-4-硝基苯乙基-(2-羟基-2-苯乙基)-氨基甲酸叔丁酯的合成方法 |
CN103232352B (zh) * | 2013-05-11 | 2015-12-23 | 苏州永健生物医药有限公司 | (r)-4-(2-(2-羟基-2-苯乙胺基)乙基)苯胺基甲酸叔丁基酯 |
BR112015030326A2 (pt) | 2013-06-05 | 2017-08-29 | Synergy Pharmaceuticals Inc | Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos |
WO2015040605A1 (en) | 2013-09-23 | 2015-03-26 | Ranbaxy Laboratories Limited | Crystalline form of mirabegron |
WO2015040573A1 (en) | 2013-09-23 | 2015-03-26 | Ranbaxy Laboratories Limited | Mirabegron dimethyl sulphoxide solvate and its use for the treatment of overactive bladder |
WO2015044965A1 (en) | 2013-09-30 | 2015-04-02 | Megafine Pharma (P) Ltd. | A process for preparation of mirabegron and alpha crystalline form thereof |
ITMI20131653A1 (it) | 2013-10-07 | 2015-04-08 | Dipharma Francis Srl | Forme cristalline di un agonista adrenergico |
WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
CN103641792B (zh) * | 2013-12-27 | 2015-07-22 | 国药集团国瑞药业有限公司 | 一种米拉贝隆有关物质或其盐、其制备方法和用途 |
CN104876889B (zh) * | 2014-02-27 | 2017-02-22 | 人福医药集团股份公司 | 化合物的合成方法 |
WO2015155664A1 (en) * | 2014-04-08 | 2015-10-15 | Suven Life Sciences Limited | An improved process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-[[(2r)-2-hydroxy-2- phenylethyl]amino]-ethyl)phenyl]acetamide |
CN103896872A (zh) * | 2014-04-29 | 2014-07-02 | 黑龙江大学 | 米拉贝隆的合成方法 |
CN104016943A (zh) * | 2014-05-23 | 2014-09-03 | 苏州凯瑞医药科技有限公司 | 一种米拉贝隆的合成方法 |
CN104016877B (zh) * | 2014-06-13 | 2017-02-15 | 南京海融制药有限公司 | 一种苯基乙酰胺类化合物及在制备米拉贝隆中的应用 |
JP6759185B2 (ja) * | 2014-08-06 | 2020-09-23 | インテルキム、ソシエダッド アノニマ | ミラベグロンおよびその誘導体の合成方法 |
WO2016024284A2 (en) | 2014-08-07 | 2016-02-18 | Wanbury Ltd. | A process for the preparation of mirabegron and its intermediates |
CN105481705A (zh) * | 2014-08-23 | 2016-04-13 | 南京海纳医药科技有限公司 | (r)-2-[[2-(4-氨基苯基)乙基]氨基]-1-苯乙醇的制备及应用 |
CN104230840A (zh) * | 2014-09-05 | 2014-12-24 | 安徽联创药物化学有限公司 | 米拉贝隆的合成方法 |
WO2016046763A1 (en) * | 2014-09-26 | 2016-03-31 | Universita' Degli Studi Di Bari | Selective agonists of beta-adrenergic type 3 receptors (bar3) and use thereof |
US20170291882A1 (en) * | 2014-10-01 | 2017-10-12 | Apotex Inc. | Solid Forms of Mirabegron |
US9981927B2 (en) | 2015-02-02 | 2018-05-29 | Lupin Limited | Process for preparation of polymorphic form of Mirabegron |
JP2018090490A (ja) | 2015-03-31 | 2018-06-14 | アステラス製薬株式会社 | ミラベグロン含有医薬組成物 |
FR3043555B1 (fr) * | 2015-11-17 | 2019-10-25 | Centre National De La Recherche Scientifique (Cnrs) | Mirabegron pour le traitement de maladies retiniennes |
EP3184516A1 (de) | 2015-12-23 | 2017-06-28 | Enantia, S.L. | Kristalliner inclusionskomplex von mirabegron mit beta-cyclodextrin |
CN105801438A (zh) * | 2016-04-12 | 2016-07-27 | 济南大学 | 一种米拉贝隆中间体的合成方法 |
CN107963976A (zh) * | 2016-10-20 | 2018-04-27 | 中国动物疫病预防控制中心 | 一种苯乙醇胺类化合物中间体的制备方法 |
US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
US10968232B2 (en) | 2016-12-20 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
EP3360866B1 (de) | 2017-02-14 | 2019-01-02 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Mirabegron-prodrugs |
KR101868438B1 (ko) | 2017-04-13 | 2018-06-20 | (주) 성운파마코피아 | 아미드 유도체의 제조방법 |
KR102398639B1 (ko) | 2017-06-20 | 2022-05-17 | (주) 성운파마코피아 | 아미드 유도체의 염 및 그 제조방법 |
CN108658797A (zh) * | 2018-06-19 | 2018-10-16 | 安徽德信佳生物医药有限公司 | 一种米拉贝隆中间体(r)-2-(4-硝基苯乙基氨基)-1-苯基乙醇盐酸盐的合成 |
CN108947853A (zh) * | 2018-06-29 | 2018-12-07 | 黑龙江鑫创生物科技开发有限公司 | 一种微通道反应器合成米拉贝隆中间体的方法 |
KR101928987B1 (ko) * | 2018-08-28 | 2018-12-13 | (주) 성운파마코피아 | 신규한 고순도 미라베그론의 결정질 일수화물, 이의 제조방법 또는 용도 |
KR20200117091A (ko) | 2019-04-02 | 2020-10-14 | 제이투에이치바이오텍 (주) | 미라베그론 전구체 약물 화합물 및 이의 과민성 방광 질환의 치료 또는 개선을 위한 의약 용도 |
CN110590699B (zh) * | 2019-09-29 | 2022-11-15 | 广东先强药业有限公司 | 一种米拉贝隆的精制方法 |
EP3722285B1 (de) | 2020-04-08 | 2022-03-30 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Verfahren zur herstellung von mirabegron-enacarbil |
CN113816864B (zh) * | 2020-06-18 | 2024-03-29 | 南京正大天晴制药有限公司 | 一种(r)-2-羟基-n-[2-(4-氨基苯基)乙基]-2-苯乙胺的制备方法 |
CN114539182B (zh) * | 2020-11-24 | 2024-08-09 | 威智医药股份有限公司 | 转晶溶剂及其应用和米拉贝隆α晶型的制备方法 |
CN114539084B (zh) * | 2020-11-24 | 2024-04-02 | 威智医药股份有限公司 | 米拉贝隆及其中间体的制备方法 |
KR20220081033A (ko) | 2020-12-08 | 2022-06-15 | 주식회사 한서켐 | 미라베그론 α형 결정의 제조방법 |
CN112574137A (zh) * | 2021-01-19 | 2021-03-30 | 南京美瑞制药有限公司 | 一种α晶型米拉贝隆的制备方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1921577B2 (de) * | 1969-04-28 | 1972-04-06 | Nixdorf Computer Ag, 4790 Paderborn | Trommelartige vorrichtung zn buchungs- und schreibautomaten mit greifeinrichtung zum erfassen und einziehen von kontokarten o dgl |
JPH02279685A (ja) | 1989-04-18 | 1990-11-15 | Yoshitomi Pharmaceut Ind Ltd | 新規な結晶構造を有するチアジアジン化合物およびその製造法 |
ID23989A (id) * | 1997-10-17 | 2000-06-14 | Yamanouchi Pharma Co Ltd | Turunan-turunan amida atau garam-garamnya |
JP3901832B2 (ja) | 1998-03-13 | 2007-04-04 | 大日本インキ化学工業株式会社 | キノリノン誘導体製剤、及びその製造法 |
JP2000212168A (ja) | 1999-01-22 | 2000-08-02 | Yamanouchi Pharmaceut Co Ltd | ヘキサヒドロ―1,4―ジアゼピン誘導体塩水和物の新規結晶 |
CN1176654C (zh) * | 1999-09-10 | 2004-11-24 | 大日本油墨化学工业株式会社 | 喹啉酮衍生物制剂及其制法 |
US6706733B2 (en) * | 2001-05-08 | 2004-03-16 | Dainippon Ink And Chemicals, Inc. | Quinolinone derivative formulation and its production method |
US7342117B2 (en) * | 2001-10-30 | 2008-03-11 | Astellas Pharma Inc. | α-form or β-form crystal of acetanilide derivative |
-
2002
- 2002-10-20 US US10/494,018 patent/US7342117B2/en not_active Expired - Lifetime
- 2002-10-28 TW TW091132011A patent/TW200300020A/zh not_active IP Right Cessation
- 2002-10-29 BR BRPI0213570A patent/BRPI0213570B8/pt active IP Right Grant
- 2002-10-29 ES ES10075435T patent/ES2404071T3/es not_active Expired - Lifetime
- 2002-10-29 EP EP02779929A patent/EP1440969A4/de not_active Withdrawn
- 2002-10-29 KR KR1020047006428A patent/KR100908796B1/ko active IP Right Review Request
- 2002-10-29 HU HU0401665A patent/HU230481B1/hu unknown
- 2002-10-29 PL PL369874A patent/PL218982B1/pl unknown
- 2002-10-29 JP JP2003540162A patent/JP3800220B2/ja not_active Expired - Lifetime
- 2002-10-29 MX MXPA04003936A patent/MXPA04003936A/es active IP Right Grant
- 2002-10-29 CA CA002464068A patent/CA2464068C/en not_active Expired - Lifetime
- 2002-10-29 WO PCT/JP2002/011217 patent/WO2003037881A1/ja active Application Filing
- 2002-10-29 AU AU2002344419A patent/AU2002344419C1/en active Active
- 2002-10-29 EP EP10075435A patent/EP2298752B1/de not_active Expired - Lifetime
- 2002-10-29 RU RU2004116313/04A patent/RU2303033C2/ru active
- 2002-10-29 CN CNB02821370XA patent/CN1243740C/zh not_active Expired - Lifetime
- 2002-10-29 EP EP08004921A patent/EP1932838A3/de not_active Withdrawn
-
2004
- 2004-04-21 ZA ZA2004/03044A patent/ZA200403044B/en unknown
- 2004-05-28 NO NO20042227A patent/NO326965B1/no not_active IP Right Cessation
-
2008
- 2008-01-14 US US12/007,653 patent/US7982049B2/en active Active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO326965B1 (no) | a-form eller β-form-krystall av acetanilid-derivat og farmasoytisk preparat | |
RU2414470C2 (ru) | Кристаллические формы соединения тиазолидиндиона и способ его получения | |
HU224212B1 (hu) | 5-[4-[2-(N-metil-N-(2-piridil)amino)etoxi]benzil]tiazolidin-2,4-dion-maleát és ezt tartalmazó gyógyszerkészítmények | |
CZ283181B6 (cs) | Farmaceutická činidla | |
PL208061B1 (pl) | Postać krystaliczna heptahydratu soli disodowej kwasu N-[4-[2-(2-amino-4,7-dihydro-4-okso-3H-pirolo [2,3-d]-pirymidyn-5-ylo) etylo] benzoilo]-L-glutaminowego i jej zastosowanie | |
US20100010098A1 (en) | Polymorphs of rasagiline hydrochloride | |
US20080234323A1 (en) | Amorphous and Three Crystalline Forms of Rimonabant Hydrochloride | |
CA2599637A1 (fr) | Sel besylate de la 7-(2-(4-(3-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyrid-1-yl)ethyl) isoquinoleine, sa preparation et son utilisation en therapeutique | |
US20030191347A1 (en) | Venlafaxine base | |
JP6965274B2 (ja) | ナトリウム−グルコース結合輸送体阻害剤のアミン溶媒和物、その調製方法およびその適用 | |
KR20010013127A (ko) | 신규 염 | |
WO2010111951A1 (zh) | 普拉格雷氢溴酸盐的晶体 | |
CN112521380A (zh) | 一种利伐沙班中间体a的合成方法及其在制备利伐沙班中的应用 | |
JP2018518515A (ja) | フェニルアミノピリミジン化合物またはその塩の多形物 | |
WO2024098856A1 (zh) | 一种抗流感病毒衍生物及其用途 | |
CA3213234A1 (en) | Preparation method of quinoline derivative compounds | |
TW202333739A (zh) | 二肽基肽酶1抑制劑多晶型物及其製備方法和用途 | |
CN106188016A (zh) | 盐酸达卡他韦的二水合物及其制备方法 | |
SK288226B6 (sk) | Kryštalická alfa-forma Imatinib mezylátu s novým habitom a spôsob jeho prípravy a použitie | |
KR20110038781A (ko) | 무정형 아데포비아 디피복실을 포함하는 약학 조성물 및 이의 제조 방법 | |
FR2793790A1 (fr) | Hydrate de pyrrolidone carboxylate de n-dimethyl amino ethanol sous forme cristallisee |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK1K | Patent expired |