CN1245974C - 卡维地洛 - Google Patents
卡维地洛 Download PDFInfo
- Publication number
- CN1245974C CN1245974C CNB018146163A CN01814616A CN1245974C CN 1245974 C CN1245974 C CN 1245974C CN B018146163 A CNB018146163 A CN B018146163A CN 01814616 A CN01814616 A CN 01814616A CN 1245974 C CN1245974 C CN 1245974C
- Authority
- CN
- China
- Prior art keywords
- carvedilol
- solvent
- chemical compound
- type
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229960004195 carvedilol Drugs 0.000 title claims abstract description 236
- NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 title claims abstract 8
- 238000000034 method Methods 0.000 claims abstract description 71
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 12
- 239000011877 solvent mixture Substances 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- SVWKIGRDISDRLO-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-9h-carbazole Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OCC1CO1 SVWKIGRDISDRLO-UHFFFAOYSA-N 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 description 234
- 239000000243 solution Substances 0.000 description 85
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- VLNNJWRDIPGHBE-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)-9h-carbazole Chemical compound C=1C=CC(C2=CC=CC=C2N2)=C2C=1OCC1CO1 VLNNJWRDIPGHBE-UHFFFAOYSA-N 0.000 description 26
- 238000010438 heat treatment Methods 0.000 description 21
- -1 III chemical compound Chemical class 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000002425 crystallisation Methods 0.000 description 19
- 230000008025 crystallization Effects 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000000605 extraction Methods 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000013019 agitation Methods 0.000 description 12
- 239000012296 anti-solvent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000002441 X-ray diffraction Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 229940032147 starch Drugs 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960000913 crospovidone Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating 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
- 230000000968 intestinal effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 2
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- GYVJGLPVHBCECZ-RZLHGTIFSA-N (e)-2-octadecylbut-2-enedioic acid;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCCC\C(C(O)=O)=C/C(O)=O GYVJGLPVHBCECZ-RZLHGTIFSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- CKJRKLKVCHMWLV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethanamine Chemical compound COC1=CC=CC=C1OCCN CKJRKLKVCHMWLV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010019280 Heart failures Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002876 beta blocker Substances 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
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229940069210 coreg Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000000314 lubricant Substances 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21435600P | 2000-06-28 | 2000-06-28 | |
US60/214,356 | 2000-06-28 | ||
US24635800P | 2000-11-07 | 2000-11-07 | |
US60/246,358 | 2000-11-07 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200510086095 Division CN1733727A (zh) | 2000-06-28 | 2001-06-28 | 结晶卡维地洛、其制备方法、药物组合物和制药用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1449286A CN1449286A (zh) | 2003-10-15 |
CN1245974C true CN1245974C (zh) | 2006-03-22 |
Family
ID=26908910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB018146163A Expired - Fee Related CN1245974C (zh) | 2000-06-28 | 2001-06-28 | 卡维地洛 |
Country Status (15)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104592096A (zh) * | 2014-12-24 | 2015-05-06 | 江苏苏南药业实业有限公司 | 一种s-卡维地洛的制备方法 |
Families Citing this family (188)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002000216A1 (en) | 2000-06-28 | 2002-01-03 | Teva Pharmaceutical Industries Ltd. | Carvedilol |
EP1416931B1 (en) * | 2001-08-13 | 2007-06-13 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Inhibitors of polyq-aggregation |
GB0119865D0 (en) * | 2001-08-14 | 2001-10-10 | Cancer Res Campaign Tech | DNA-PK inhibitors |
DE60221683T2 (de) * | 2001-09-28 | 2008-04-30 | F. Hoffmann-La Roche Ag | Pseudopolymorphe formen von carvedilol |
US8101209B2 (en) | 2001-10-09 | 2012-01-24 | Flamel Technologies | Microparticulate oral galenical form for the delayed and controlled release of pharmaceutical active principles |
DE10156894A1 (de) * | 2001-11-20 | 2003-05-28 | Bayer Ag | Harnstoffe |
BR0215212A (pt) * | 2001-12-21 | 2004-12-07 | Novo Nordisk As | Ativador de carboxamida ou sulfonamida de glicoquinase, composto, composição farmacêutica, e, uso de um composto |
JP2005515226A (ja) * | 2002-01-15 | 2005-05-26 | テバ ファーマシューティカル インダストリーズ リミティド | カルベジロールの結晶質固体及びそれらを調製するための方法 |
EP1499310A4 (en) * | 2002-04-30 | 2005-12-07 | Sb Pharmco Inc | MONOCITRATE MONOHYDRATE OF CARVEDILOL |
AU2003231307A1 (en) * | 2002-05-03 | 2003-11-17 | Smithkline Beecham Pharmco Puerto Rico, Inc. | Carvedilol pharmasolve solvate |
TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
JP2005533822A (ja) | 2002-06-27 | 2005-11-10 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | 臭化水素酸カルベジロール |
CN103254114A (zh) * | 2002-06-27 | 2013-08-21 | 史密斯克莱.比奇曼(科克)有限公司 | 卡维地洛磷酸盐和/或其溶剂合物相应的组合物和/或治疗方法 |
KR101116627B1 (ko) | 2002-06-27 | 2012-10-09 | 노보 노르디스크 에이/에스 | 치료제로서 아릴 카르보닐 유도체 |
US7915301B2 (en) * | 2002-07-08 | 2011-03-29 | Piramal Life Science Limited | Inhibitors of cyclin dependent kinases and their use |
DE60326348D1 (de) * | 2002-07-15 | 2009-04-09 | Biotechnolog Forschung Gmbh | Makrozyclen zur behandlung von krebserkrankungen |
US20040152756A1 (en) * | 2002-07-15 | 2004-08-05 | Wei Chen | Carvedilol polymorph |
SE0202241D0 (sv) * | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
TW200407127A (en) * | 2002-08-21 | 2004-05-16 | Astrazeneca Ab | Chemical compounds |
SK285547B6 (sk) | 2002-11-08 | 2007-03-01 | Zentiva, A. S. | Spôsob prípravy Carvedilolu |
WO2004048372A1 (en) * | 2002-11-28 | 2004-06-10 | Morphochem Ag Komb Chemie | Thia-epothilone derivatives for the treatment of cancer |
US7759336B2 (en) * | 2002-12-10 | 2010-07-20 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
US20060166983A1 (en) * | 2003-01-06 | 2006-07-27 | Eli Lilly And Company | Indole derivatives as ppar modulators |
DK1599468T3 (da) * | 2003-01-14 | 2008-02-04 | Arena Pharm Inc | 1,2,3-trisubstituerede aryl- og heteroarylderivater som modulatorer af metabolisme og forebyggelse og behandling af forstyrrelser forbundet dermed såsom diabetes og hyperglykæmi |
SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
SE0301009D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
GB0308186D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
WO2004094378A1 (en) | 2003-04-21 | 2004-11-04 | Matrix Laboratories Ltd | Process for the preparation of carvedilol form-ii |
CN1826310B (zh) * | 2003-07-24 | 2010-07-21 | 利奥制药有限公司 | 新的氨基二苯酮化合物 |
CN1867566B (zh) * | 2003-08-13 | 2010-06-16 | 库多斯药物有限公司 | 氨基吡喃酮和它们作为atm抑制剂的用途 |
SA04250253B1 (ar) * | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
SI21616A (sl) * | 2003-09-02 | 2005-04-30 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove kristalne oblike karvedilola |
WO2005035495A2 (en) * | 2003-10-08 | 2005-04-21 | Nicholas Piramal India Limited | Fibrinogen receptor antagonists and their use |
TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
US8734850B2 (en) * | 2003-11-25 | 2014-05-27 | Flamel Technologies | Oral medicinal product with modified release of at least one active principle in multimicrocapsular form |
JP2007512350A (ja) * | 2003-11-25 | 2007-05-17 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | カルベジロール組成物の治療および送達方法 |
JP2007512372A (ja) * | 2003-11-25 | 2007-05-17 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | カルベジロール塩、対応する組成物、送達および/または治療方法 |
DK1723128T3 (da) | 2004-01-06 | 2013-02-18 | Novo Nordisk As | Heteroarylurinstoffer og deres anvendelse som glucokinaseaktivatorer |
US20070105770A1 (en) * | 2004-01-21 | 2007-05-10 | Novo Nordisk A/S | Transglutaminase mediated conjugation of peptides |
CA2560353A1 (en) * | 2004-02-23 | 2005-09-01 | Cadila Healthcare Limited | Process for manufacture of racemic carvedilol |
DE602005025222D1 (de) * | 2004-03-31 | 2011-01-20 | Janssen Pharmaceutica Nv | Heterocyclische nichtimidazolverbindungen als modulatoren des histamin-h3-rezeptors |
US7705036B2 (en) * | 2004-04-01 | 2010-04-27 | Cardiome Pharma Corp. | Deuterated aminocyclohexyl ether compounds and processes for preparing same |
EP1753735A1 (en) * | 2004-04-20 | 2007-02-21 | Transtech Pharma, Inc. | Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators |
CA2649054A1 (en) * | 2004-05-05 | 2005-11-10 | Pfizer Products Inc. | Salt forms of [r-(r*,r*)]-2-(4-fluorophenyl)-.beta., .delta.-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid |
GB0411273D0 (en) * | 2004-05-20 | 2004-06-23 | Cipla Ltd | Process and product |
US7638513B2 (en) * | 2004-06-02 | 2009-12-29 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
PE20060426A1 (es) * | 2004-06-02 | 2006-06-28 | Schering Corp | DERIVADOS DE ACIDO TARTARICO COMO INHIBIDORES DE MMPs, ADAMs, TACE Y TNF-alfa |
US20070167426A1 (en) * | 2004-06-02 | 2007-07-19 | Schering Corporation | Compounds for the treatment of inflammatory disorders and microbial diseases |
GB0413605D0 (en) | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
GB0418613D0 (en) * | 2004-08-20 | 2004-09-22 | Pugh Rhoderick | Internet security system |
GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
US7402607B2 (en) * | 2004-09-20 | 2008-07-22 | Kudos Pharmaceuticals Limited | DNA-PK inhibitors |
EP1806141B1 (en) * | 2004-09-30 | 2010-12-01 | Kowa Company, Ltd. | Par-2 antagonists |
GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
US20080051416A1 (en) * | 2004-10-05 | 2008-02-28 | Smithkline Beecham Corporation | Novel Compounds |
GB0422263D0 (en) * | 2004-10-07 | 2004-11-10 | Glaxo Group Ltd | Novel compounds |
KR20070084172A (ko) * | 2004-10-12 | 2007-08-24 | 아스트라제네카 아베 | 퀴나졸린 유도체 |
TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
DE102004051024A1 (de) * | 2004-10-20 | 2006-04-27 | Bayer Healthcare Ag | Heterocyclyl-substituierte Nonadepsipeptide |
DE102004051023A1 (de) * | 2004-10-20 | 2006-05-04 | Bayer Healthcare Ag | Desoxo-Nonadepsipeptide |
DE102004051025A1 (de) * | 2004-10-20 | 2006-04-27 | Bayer Healthcare Ag | Substituierte Nonadepsipeptide |
DE102004053410A1 (de) * | 2004-11-05 | 2006-05-11 | Bayer Healthcare Ag | Cyclische Nonadepsipeptidamide |
EP1828099B1 (en) | 2004-11-18 | 2020-01-22 | Correvio International Sàrl | Synthetic process for aminocyclohexyl ether compounds |
UY29223A1 (es) * | 2004-11-23 | 2006-06-30 | Astrazeneca Ab | Ácidos fenoxiacéticos sustituidos, composiciones farmacéuticas que los contienen y procesos para su preparación |
NZ555320A (en) * | 2004-12-03 | 2010-11-26 | Schering Corp | Substituted piperazines as CB1 antagonists |
JP2008523025A (ja) * | 2004-12-09 | 2008-07-03 | ザック システム エス.ピー.エー. | カルベジロール及びそのエナンチオマーの調製プロセス |
MX2007007590A (es) | 2004-12-22 | 2007-12-10 | Ambrx Inc | Composiciones que contienen, metodos que involucran y usos de aminoacidos no naturales y polipeptidos. |
EP1845104A4 (en) * | 2004-12-28 | 2009-08-05 | Kowa Co | AGONIST OF THE RECEIVER PAR-2 |
TW200638938A (en) * | 2005-02-09 | 2006-11-16 | Kudos Pharm Ltd | ATM inhibitors |
US20070142437A1 (en) * | 2005-04-08 | 2007-06-21 | Brown Matthew L | Chemical compounds |
AR053358A1 (es) * | 2005-04-15 | 2007-05-02 | Cancer Rec Tech Ltd | Inhibidores de adn - pk |
US7816405B2 (en) * | 2005-04-19 | 2010-10-19 | Eisai R&D Management Co., Ltd. | Calcium bis [(2S)-3-[3-[(2S)-3-(4-chloro-2-cyanophenoxy)-2-fluoropropoxy]phenyl ]-2-isopropoxypropionate] and intermediate thereof |
CA2605481A1 (en) * | 2005-04-21 | 2007-02-15 | Targanta Therapeutics Inc. | Phosphonated fluoroquinolones, antibacterial analogs thereof, and methods for the prevention and treatment of bone and joint infections |
DE602006019710D1 (de) * | 2005-05-03 | 2011-03-03 | Ranbaxy Lab Ltd | Magnesiumsalze von hmg-coa-reduktase-hemmern |
WO2006135757A1 (en) * | 2005-06-09 | 2006-12-21 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of carvedilol and processes for their preparation |
JP5159616B2 (ja) * | 2005-06-15 | 2013-03-06 | カーディオム ファーマ コーポレイション | アミノシクロヘキシルエーテル化合物の調製のための合成プロセス |
EP1741444A1 (en) * | 2005-07-05 | 2007-01-10 | Jerini AG | Kinin antagonists for treating bladder dysfunction |
WO2007008848A2 (en) | 2005-07-07 | 2007-01-18 | Seattle Genetics, Inc. | Monomethylvaline compounds having phenylalanine carboxy modifications at the c-terminus |
EP2722051B1 (en) * | 2005-07-07 | 2018-11-07 | Seattle Genetics, Inc. | Monomethylvaline compounds having phenylalanine side-chain modifications at the C-terminus |
JP2009500378A (ja) * | 2005-07-08 | 2009-01-08 | ノボ・ノルデイスク・エー/エス | グルコキナーゼ活性化剤としてのジシクロアルキルカルバモイル尿素 |
JP4960355B2 (ja) * | 2005-07-14 | 2012-06-27 | ノボ・ノルデイスク・エー/エス | ウレア型グルコキナーゼ活性化剤 |
EP1909797A4 (en) * | 2005-08-02 | 2013-02-27 | Neurogen Corp | DIPIPERAZINYL KETONE AND RELATED ANALOG |
EP1928848A2 (en) * | 2005-08-04 | 2008-06-11 | Apogee Biothechnology Corporation | Sphingosine kinase inhibitors and methods of their use |
US8158590B2 (en) * | 2005-08-05 | 2012-04-17 | Syntarga B.V. | Triazole-containing releasable linkers, conjugates thereof, and methods of preparation |
RU2008105545A (ru) * | 2005-08-30 | 2009-10-10 | Ново Нордиск Хелс Кеа Аг (Ch) | Жидкие препараты пэгилированного гормона роста |
MY151003A (en) | 2005-09-12 | 2014-03-31 | Actelion Pharmaceuticals Ltd | Stable pharmaceutical composition comprising a pyrimidine-sulfamide |
TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
JP5155171B2 (ja) | 2005-10-06 | 2013-02-27 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
TWI396541B (zh) * | 2005-10-10 | 2013-05-21 | Boehringer Ingelheim Int | 用於治療呼吸疾病之新穎藥物組合 |
JP2009514935A (ja) * | 2005-11-05 | 2009-04-09 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
CN101400646A (zh) * | 2005-11-08 | 2009-04-01 | Ambrx公司 | 用于修饰非天然氨基酸和非天然氨基酸多肽的促进剂 |
PT103385B (pt) * | 2005-11-15 | 2011-06-27 | Jorge Ruas Da Silva | Ácido 2,3,4,5-tetrahidróxi-6-sulfooxi-hexanoico, seus sais farmaceuticamente aceitáveis e suas formas de equilíbrio, processo para a sua preparação, composições farmacêuticas contendo estes compostos e seu uso em medicina |
US7714014B2 (en) * | 2005-12-09 | 2010-05-11 | The Regents Of The University Of California | Targeting GLI proteins in human cancer by small molecules |
CN101365469A (zh) * | 2005-12-13 | 2009-02-11 | 哈克尼斯药品公司 | 使用肠抑素治疗肥胖的方法 |
WO2007070562A2 (en) * | 2005-12-13 | 2007-06-21 | Harkness Pharmaceuticals, Inc. | Non-hygroscopic compositions of enterostatin |
WO2007070563A2 (en) * | 2005-12-13 | 2007-06-21 | Harkness Pharmaceuticals, Inc. | Stable solid forms of enterostatin |
CN105384807A (zh) * | 2005-12-14 | 2016-03-09 | Ambrx公司 | 含有非天然氨基酸和多肽的组合物、涉及非天然氨基酸和多肽的方法以及非天然氨基酸和多肽的用途 |
US20080293775A1 (en) * | 2005-12-15 | 2008-11-27 | Astrazeneca Ab | Substituted Diphenylethers, -Amines, -Sulfides and -Methanes for the Treatment of Respiratory Disease |
WO2007077111A1 (en) * | 2005-12-30 | 2007-07-12 | F. Hoffmann-La Roche Ag | Compounds and methods for carbazole synthesis |
US8975404B2 (en) * | 2006-01-24 | 2015-03-10 | Dh Technologies Development Pte. Ltd. | Labeling reagents for analyte determination and methods and compounds used in making the same |
DE102006003443A1 (de) * | 2006-01-25 | 2007-07-26 | Aicuris Gmbh & Co. Kg | Asparagin-10-substituierte Nonadepsipeptide |
KR100746455B1 (ko) * | 2006-02-23 | 2007-08-03 | 안국약품 주식회사 | 고광학순도의 키랄 카베딜롤의 제조방법 |
US8653238B2 (en) * | 2006-02-27 | 2014-02-18 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for transport of molecules with enhanced release properties across biological barriers |
US8367112B2 (en) | 2006-02-28 | 2013-02-05 | Alkermes Pharma Ireland Limited | Nanoparticulate carverdilol formulations |
CA2647158C (en) * | 2006-03-23 | 2012-07-31 | Schering Corporation | Combinations of hcv protease inhibitor(s) and cyp3a4 inhibitor(s), and methods of treatment related thereto |
WO2007110449A1 (en) * | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
CN103497173A (zh) | 2006-03-31 | 2014-01-08 | 财团法人乙卯研究所 | 具有杂环的新化合物 |
US8937181B2 (en) * | 2006-04-13 | 2015-01-20 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
TW200815353A (en) * | 2006-04-13 | 2008-04-01 | Euro Celtique Sa | Benzenesulfonamide compounds and their use |
DE102006018080A1 (de) * | 2006-04-13 | 2007-10-18 | Aicuris Gmbh & Co. Kg | Lysobactinamide |
DE102006018250A1 (de) * | 2006-04-13 | 2007-10-18 | Aicuris Gmbh & Co. Kg | Verfahren zum Herstellen von cyclischen Depsipeptiden |
UA93548C2 (uk) * | 2006-05-05 | 2011-02-25 | Айерем Елелсі | Сполуки та композиції як модулятори хеджхогівського сигнального шляху |
US20070281910A1 (en) * | 2006-06-06 | 2007-12-06 | Xenoport, Inc. | Salicyl alcohol creatine phosphate prodrugs, compositions and uses thereof |
US20070281996A1 (en) * | 2006-06-06 | 2007-12-06 | Xenoport, Inc. | Creatine prodrugs, compositions and uses thereof |
US20070281983A1 (en) * | 2006-06-06 | 2007-12-06 | Xenoport, Inc. | Creatine analog prodrugs, compositions and uses thereof |
US7683043B2 (en) * | 2006-06-06 | 2010-03-23 | Xenoport, Inc. | Creatine phosphate analog prodrugs, compositions and uses thereof |
US20070281909A1 (en) * | 2006-06-06 | 2007-12-06 | Xenoport, Inc. | Creatine phosphate prodrugs, compositions and uses thereof |
EP1991527A2 (en) * | 2006-06-28 | 2008-11-19 | Teva Pharmaceutical Industries Ltd | Polymorphous forms of carvedilol phosphate |
US8088733B2 (en) * | 2006-07-06 | 2012-01-03 | Tranzyme Pharma Inc. | Methods of using macrocyclic agonists of the ghrelin receptor for treatment of gastrointestinal motility disorders |
CN101495155A (zh) * | 2006-07-07 | 2009-07-29 | 诺沃-诺迪斯克保健股份有限公司 | 新的蛋白结合物及其制备方法 |
KR20090040352A (ko) * | 2006-07-31 | 2009-04-23 | 얀센 파마슈티카 엔.브이. | 유로텐신 ⅱ 수용체 길항제 |
US8088789B2 (en) | 2006-09-13 | 2012-01-03 | Elixir Medical Corporation | Macrocyclic lactone compounds and methods for their use |
US10695327B2 (en) | 2006-09-13 | 2020-06-30 | Elixir Medical Corporation | Macrocyclic lactone compounds and methods for their use |
US7867988B2 (en) | 2006-09-13 | 2011-01-11 | Elixir Medical Corporation | Macrocyclic lactone compounds and methods for their use |
GB2442238B (en) * | 2006-09-29 | 2008-10-01 | Rolls Royce Plc | Sheet metal blank |
JP2010508344A (ja) * | 2006-10-30 | 2010-03-18 | ビオヴィトルム・アクチボラゲット(プブリクト) | 8−スルホニル−1,3,4,8−テトラヒドロ−2h−[1,4]オキサゼピノ[6,7−e]インドール誘導体、および5−ht6受容体リガンドとしてのその使用 |
US20080292695A1 (en) * | 2006-12-01 | 2008-11-27 | Kristin Arnold | Carvedilol forms, compositions, and methods of preparation thereof |
US20090028935A1 (en) * | 2006-12-01 | 2009-01-29 | Kristin Arnold | Carvedilol forms, compositions, and methods of preparation thereof |
US8138185B2 (en) * | 2007-01-09 | 2012-03-20 | Novo Nordisk A/S | Urea glucokinase activators |
AU2008204530B2 (en) * | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
CZ302357B6 (cs) * | 2007-01-26 | 2011-03-30 | Zentiva, A. S. | Zpusob cištení Carvedilolu |
US20080249317A1 (en) * | 2007-04-04 | 2008-10-09 | Apotex Inc. | Novel amorphous form of carvedilol phosphate and processes for the preparation thereof |
US8399486B2 (en) * | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
DE102007026550A1 (de) * | 2007-06-08 | 2008-12-11 | Bayer Healthcare Ag | Extrudate mit verbesserter Geschmacksmaskierung |
UA100983C2 (ru) * | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
GB0714030D0 (en) * | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | The use of type-B lantibiotic-based compounds having antimicrobial activity |
UY31232A1 (es) * | 2007-07-19 | 2009-03-02 | Compuestos derivados de dibenzotifenilamino-cromen-4-onas activas sustituidas y sus isomeros y aplicaciones | |
MX2010001837A (es) | 2007-08-17 | 2010-03-10 | Actelion Pharmaceuticals Ltd | Derivados de 4-pirimidinasulfamida. |
US8278461B2 (en) * | 2007-08-21 | 2012-10-02 | Lupin Limited | Stable amorphous form of carvedilol dihydrogen phosphate with stabilizer |
US20090076116A1 (en) * | 2007-09-13 | 2009-03-19 | Protia, Llc | Deuterium-enriched carvediolo |
US8765736B2 (en) * | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
FR2927809B1 (fr) * | 2008-02-26 | 2011-01-14 | Tri Inov | Nouvelle utilisation de n-acetyl-taurinate de zinc. |
US20110003892A1 (en) * | 2008-03-06 | 2011-01-06 | Margaret Clagett-Dame | All-trans retinoid esters as active pharmaceutical ingredients, oral and topical dosage form compositions thereof, and methods of treating skin conditions thereof |
JP5557832B2 (ja) * | 2008-03-18 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換4−ヒドロキシピリジン−5−カルボキサミド |
WO2009115902A1 (en) * | 2008-03-19 | 2009-09-24 | Cadila Pharmaceuticals Ltd. | Process for the preparation of carvedilol via silyl protection of substituted amine |
US9023809B2 (en) * | 2008-03-27 | 2015-05-05 | The Key Laboratory Of Chemistry For Natural Products Of Guizhou Province And Chinese Academy Of Sciences | Phenylalanine dipeptide derivatives, compositions and use thereof |
MX2020005326A (es) | 2008-08-15 | 2022-03-03 | Ironwood Pharmaceuticals Inc | Formulaciones que contienen linaclotida para administracion oral. |
EP2157432A1 (en) * | 2008-08-15 | 2010-02-24 | Qiagen GmbH | Method for analysing a complex sample by mass spectrometry |
WO2010042834A1 (en) * | 2008-10-09 | 2010-04-15 | Anadys Pharmaceuticals, Inc. | A method of inhibiting hepatitis c virus by combination of a 5,6-dihydro-1h-pyridin-2-one and one or more additional antiviral compounds |
US20100197567A1 (en) * | 2008-10-17 | 2010-08-05 | University Of Utah Research Foundation | Conus polypeptides |
MX2011005256A (es) * | 2008-11-20 | 2011-05-31 | Merck Patent Gmbh | Nueva terapia y medicamento que usa liganodos de integrina para tratamiento de cancer. |
EP2370104A1 (en) * | 2008-11-25 | 2011-10-05 | Novo Nordisk A/S | Peptides for treatment of obesity |
EP2396327A1 (en) | 2009-02-11 | 2011-12-21 | Sunovion Pharmaceuticals Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
MX2012001660A (es) * | 2009-08-06 | 2012-03-26 | Ironwood Pharmaceuticals Inc | Formulaciones que contienen linaclotida para adminstracion oral. |
US20130203861A1 (en) * | 2009-09-09 | 2013-08-08 | Golden Biotechnology Corporation | Methods and compositions for treating ovarian cancer |
EP2475662A2 (en) * | 2009-09-11 | 2012-07-18 | Sunovion Pharmaceuticals Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
ES2937386T3 (es) | 2010-01-27 | 2023-03-28 | Arena Pharm Inc | Procesos para la preparación de ácido (R)-2-(7-(4-ciclopentil-3-(trifluorometil)benciloxi)-1,2,3,4-tetrahidrociclopenta[b]indol-3-il)acético y sales del mismo |
GB201001688D0 (en) | 2010-02-02 | 2010-03-17 | Novacta Biosystems Ltd | Compounds |
WO2011103311A2 (en) | 2010-02-17 | 2011-08-25 | Ironwood Pharmaceuticals, Inc | Treatments for gastrointestinal disorders |
CN102190613B (zh) * | 2010-03-14 | 2014-06-25 | 浙江华海药业股份有限公司 | 一种卡维地洛的制备方法 |
GB201013513D0 (en) | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Formulations |
US20140005128A1 (en) | 2010-08-11 | 2014-01-02 | Forest Laboratories Holdings Limited | Treatments of gastrointestinal disorders |
US9102712B2 (en) * | 2010-08-27 | 2015-08-11 | New York University | Dendrimeric peptides, pharmaceutical compositions and methods of using the same |
SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
US9220672B2 (en) * | 2011-02-09 | 2015-12-29 | Organobalance Gmbh | Peptide for use in the treatment of skin conditions |
TW201300105A (zh) | 2011-05-31 | 2013-01-01 | Piramal Life Sciences Ltd | 治療頭頸鱗狀細胞癌之相乘藥物組合物 |
EP2776055B1 (en) | 2011-08-17 | 2016-12-14 | Ironwood Pharmaceuticals, Inc. | Treatments for gastrointestinal disorders |
EP2825534A1 (en) * | 2012-03-16 | 2015-01-21 | Sandoz AG | Process for the synthesis of telaprevir, or pharmaceutically acceptable salts or solvates as well as intermediate products thereof |
US9816066B2 (en) | 2012-04-24 | 2017-11-14 | The Regents Of The University Of California | Method for delivery of small molecules and proteins across the cell wall of algae using molecular transporters |
US8492426B1 (en) | 2012-07-12 | 2013-07-23 | Anis Ahmad | Use of carvedilol for treatment of diabetes mellitus |
US20150299250A1 (en) * | 2012-11-16 | 2015-10-22 | Adelaide Research & Innovation Pty Ltd | Macrocyclic compounds and uses thereof |
EP2950803A1 (en) * | 2013-01-30 | 2015-12-09 | Sandoz AG | Crystalline form of linaclotide |
WO2014191575A1 (en) * | 2013-05-31 | 2014-12-04 | Centre National De La Recherche Scientique (Cnrs) | Protein involved in dna replication, and modulation of its activity |
US20160145304A1 (en) * | 2013-07-12 | 2016-05-26 | Helmholtz-Zentrum für Infektionsforschung GmbH | Cystobactamides |
US11007174B2 (en) | 2013-07-12 | 2021-05-18 | Piramal Enterprises Limited | Pharmaceutical combination for the treatment of melanoma |
US20160214973A1 (en) * | 2013-08-30 | 2016-07-28 | Uti Limited Partnership | Store overload-induced calcium release inhibitors and methods for producing and using the same |
US10053490B2 (en) * | 2014-01-22 | 2018-08-21 | Agency For Science, Technology And Research | Antimicrobial peptidomimetics |
WO2015113760A1 (en) * | 2014-01-28 | 2015-08-06 | Tube Pharmaceuticals Gmbh | Cytotoxic tubulysin compounds for conjugation |
AU2015353077B2 (en) | 2014-11-26 | 2020-03-05 | Helmholtz-Zentrum Fur Infektionsforschung Gmbh | Novel cystobactamides |
EP3242666A1 (en) | 2015-01-06 | 2017-11-15 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | アリーナ ファーマシューティカルズ, インコーポレイテッド | S1P1レセプター関連障害における使用のための(R)−2−(7−(4−シクロペンチル−3−(トリフルオロメチル)ベンジルオキシ)−1,2,3,4−テトラヒドロシクロペンタ[b]インドール−3−イル)酢酸(化合物1)の結晶性L−アルギニン塩 |
KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
CA3084073C (en) | 2017-11-30 | 2023-04-25 | Hanmi Pharm. Co., Ltd. | Salts of 4-amino-n-(1-((3-chloro-2-fluorophenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide, and crystalline forms thereof |
MX2020008905A (es) | 2018-06-12 | 2020-12-03 | Vtv Therapeutics Llc | Usos terapeuticos de activadores de glucoquinasa en combinacion con insulina o analogos de insulinas. |
US10357476B1 (en) | 2018-10-30 | 2019-07-23 | Anis Ahmad | Method for treating coronary artery disease |
US10772869B1 (en) | 2019-07-24 | 2020-09-15 | ECI Pharmaceuticals, LLC | Pharmaceutical compositions including carvedilol and methods of using the same |
CN110790817A (zh) * | 2019-11-12 | 2020-02-14 | 成都诺和晟泰生物科技有限公司 | 一种多肽类化合物、制剂、药物组合物及制备方法、应用 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2815926A1 (de) | 1978-04-13 | 1979-10-18 | Boehringer Mannheim Gmbh | Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE3319027A1 (de) * | 1983-05-26 | 1984-11-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur herstellung von optisch aktiven carbazol-derivaten, neue r- und s-carbazol-derivate, sowie arzneimittel, die diese verbindungen enthalten |
FR2725623A1 (fr) | 1994-10-18 | 1996-04-19 | Flamel Tech Sa | Microcapsules medicamenteuses et/ou nutritionnelles pour administration per os |
US5760069A (en) | 1995-02-08 | 1998-06-02 | Boehringer Mannheim Pharmaceuticals Corporation-Smithkline Beecham Corporation Limited Partnership #1 | Method of treatment for decreasing mortality resulting from congestive heart failure |
US6730326B2 (en) | 1997-07-22 | 2004-05-04 | Roche Diagnostics Gmbh | Thermodynamically stable modification of 1-(4-carbazolyl-oxy-3[2-(2-methoxyphenoxy)-ethylamino]-2-propanol process for its preparation and pharmaceutical compositions containing it |
EP0893440A1 (en) | 1997-07-22 | 1999-01-27 | Roche Diagnostics GmbH | Thermodynamically stable modification of 1-(4-carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it |
HU227441B1 (en) | 1997-11-24 | 2011-06-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Process for producing carvedilol, enantiomers and salts thereof |
DE19954569A1 (de) | 1999-11-12 | 2001-05-17 | Schwabe Willmar Gmbh & Co | Pharmakologisch aktive Tetrahydrothiopyran-4-ol-Derivate, Verfahren zu ihrer Herstellung und Verwendung |
IT1318379B1 (it) | 2000-03-08 | 2003-08-25 | Ira Srl | Composizione cosmetica o farmaceutica utile per inibire o ritardarel'alopecia umana mediante applicazione topica della composizione. |
WO2002000216A1 (en) | 2000-06-28 | 2002-01-03 | Teva Pharmaceutical Industries Ltd. | Carvedilol |
US6365618B1 (en) | 2000-12-13 | 2002-04-02 | Conrad M. Swartz | Administration of carvedilol to mitigate tardive movement disorders, psychosis, mania, and depression |
CA2434408C (en) | 2001-01-25 | 2009-10-20 | F. Hoffmann-La Roche Ag | Process for the preparation of heterocyclic indene analogs |
JP2004534840A (ja) | 2001-07-13 | 2004-11-18 | スミスクライン・ビーチャム・コーポレイション | カルベジロール多型体 |
DE60221683T2 (de) | 2001-09-28 | 2008-04-30 | F. Hoffmann-La Roche Ag | Pseudopolymorphe formen von carvedilol |
JP2005515226A (ja) | 2002-01-15 | 2005-05-26 | テバ ファーマシューティカル インダストリーズ リミティド | カルベジロールの結晶質固体及びそれらを調製するための方法 |
CN103254114A (zh) | 2002-06-27 | 2013-08-21 | 史密斯克莱.比奇曼(科克)有限公司 | 卡维地洛磷酸盐和/或其溶剂合物相应的组合物和/或治疗方法 |
US20040152756A1 (en) | 2002-07-15 | 2004-08-05 | Wei Chen | Carvedilol polymorph |
SK285547B6 (sk) | 2002-11-08 | 2007-03-01 | Zentiva, A. S. | Spôsob prípravy Carvedilolu |
WO2004094378A1 (en) | 2003-04-21 | 2004-11-04 | Matrix Laboratories Ltd | Process for the preparation of carvedilol form-ii |
US7482471B2 (en) | 2003-06-20 | 2009-01-27 | Sun Pharmaceutical Industries Limited | Process for preparation of 1-[9H-carbazol-4-yloxy]-3-[{2-(2-(-methoxy)phenoxy)-ethyl}-amino]-propan-2-ol |
SI21616A (sl) | 2003-09-02 | 2005-04-30 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove kristalne oblike karvedilola |
JP2007512372A (ja) | 2003-11-25 | 2007-05-17 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | カルベジロール塩、対応する組成物、送達および/または治療方法 |
CA2560353A1 (en) | 2004-02-23 | 2005-09-01 | Cadila Healthcare Limited | Process for manufacture of racemic carvedilol |
WO2005115981A2 (en) | 2004-04-22 | 2005-12-08 | Usv Limited | A process for the preparation of 1-(9h-carbazol-4-yloxy)-3-2-(-methoxyphenoxy)-ethyl amino-propan-2-ol |
GB0411273D0 (en) | 2004-05-20 | 2004-06-23 | Cipla Ltd | Process and product |
JP2008523025A (ja) | 2004-12-09 | 2008-07-03 | ザック システム エス.ピー.エー. | カルベジロール及びそのエナンチオマーの調製プロセス |
US20070027202A1 (en) | 2005-06-07 | 2007-02-01 | Ashok Kumar | Process for the preparation of carvedilol and its salts |
CA2629077C (en) | 2005-11-16 | 2014-03-18 | F. Hoffmann-La Roche Ag | Novel process for the preparation of thoc |
WO2007077111A1 (en) | 2005-12-30 | 2007-07-12 | F. Hoffmann-La Roche Ag | Compounds and methods for carbazole synthesis |
KR100746455B1 (ko) | 2006-02-23 | 2007-08-03 | 안국약품 주식회사 | 고광학순도의 키랄 카베딜롤의 제조방법 |
-
2001
- 2001-06-28 WO PCT/US2001/020760 patent/WO2002000216A1/en active Application Filing
- 2001-06-28 CA CA002413702A patent/CA2413702A1/en not_active Abandoned
- 2001-06-28 US US09/894,798 patent/US6699997B2/en not_active Expired - Fee Related
- 2001-06-28 KR KR1020027017817A patent/KR20030017569A/ko active Search and Examination
- 2001-06-28 HU HU0301802A patent/HUP0301802A3/hu unknown
- 2001-06-28 CN CNB018146163A patent/CN1245974C/zh not_active Expired - Fee Related
- 2001-06-28 SK SK86-2003A patent/SK862003A3/sk unknown
- 2001-06-28 MX MXPA02012795A patent/MXPA02012795A/es unknown
- 2001-06-28 EP EP01950671A patent/EP1299101A4/en not_active Withdrawn
- 2001-06-28 JP JP2002504998A patent/JP2004501191A/ja active Pending
- 2001-06-28 IL IL15368801A patent/IL153688A0/xx unknown
- 2001-06-28 KR KR1020077030634A patent/KR20080015888A/ko not_active Application Discontinuation
- 2001-06-28 AU AU2001271639A patent/AU2001271639A1/en not_active Abandoned
- 2001-06-28 PL PL01365694A patent/PL365694A1/xx not_active Application Discontinuation
- 2001-06-28 KR KR1020087014587A patent/KR20080064908A/ko not_active Application Discontinuation
-
2002
- 2002-12-19 IS IS6659A patent/IS6659A/is unknown
-
2003
- 2003-01-17 HR HR20030027A patent/HRP20030027A2/xx not_active Application Discontinuation
-
2004
- 2004-01-16 US US10/758,025 patent/US7056942B2/en not_active Expired - Fee Related
- 2004-01-16 US US10/758,026 patent/US7126008B2/en not_active Expired - Fee Related
-
2005
- 2005-08-31 US US11/217,643 patent/US7485663B2/en not_active Expired - Fee Related
-
2008
- 2008-04-15 US US12/148,070 patent/US7605274B2/en not_active Expired - Fee Related
-
2009
- 2009-09-01 US US12/584,205 patent/US20090326033A1/en not_active Abandoned
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104592096A (zh) * | 2014-12-24 | 2015-05-06 | 江苏苏南药业实业有限公司 | 一种s-卡维地洛的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
WO2002000216A1 (en) | 2002-01-03 |
US7126008B2 (en) | 2006-10-24 |
KR20030017569A (ko) | 2003-03-03 |
EP1299101A1 (en) | 2003-04-09 |
AU2001271639A1 (en) | 2002-01-08 |
CN1449286A (zh) | 2003-10-15 |
MXPA02012795A (es) | 2004-07-30 |
US20020143045A1 (en) | 2002-10-03 |
IS6659A (is) | 2002-12-19 |
US20040152757A1 (en) | 2004-08-05 |
HUP0301802A2 (hu) | 2003-09-29 |
US20060030614A1 (en) | 2006-02-09 |
US20040225132A1 (en) | 2004-11-11 |
SK862003A3 (en) | 2003-06-03 |
US7605274B2 (en) | 2009-10-20 |
EP1299101A4 (en) | 2004-06-16 |
HUP0301802A3 (en) | 2009-04-28 |
IL153688A0 (en) | 2003-07-06 |
KR20080064908A (ko) | 2008-07-09 |
US20080194838A1 (en) | 2008-08-14 |
US6699997B2 (en) | 2004-03-02 |
US7485663B2 (en) | 2009-02-03 |
PL365694A1 (en) | 2005-01-10 |
US20090326033A1 (en) | 2009-12-31 |
CA2413702A1 (en) | 2002-01-03 |
HRP20030027A2 (en) | 2004-02-29 |
KR20080015888A (ko) | 2008-02-20 |
US7056942B2 (en) | 2006-06-06 |
JP2004501191A (ja) | 2004-01-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1245974C (zh) | 卡维地洛 | |
CN1065536C (zh) | 2-甲基-噻吩并苯并二氮杂䓬的结晶形式及制备方法 | |
CN1028104C (zh) | 制备喹诺酮衍生物的方法 | |
JP2007518826A (ja) | モンテルカスト遊離酸多形体 | |
CN1620293A (zh) | 氯吡格雷硫酸氢盐的多晶型 | |
CN1015057B (zh) | 哌嗪基-杂环化合物的制备方法 | |
CN1434708A (zh) | 新的盐酸舍曲林多晶型物、其制备方法、含有它们的组合物和应用它们的方法 | |
CN100347164C (zh) | 苯并呋喃基衍生物及其应用 | |
CN1219131A (zh) | 作为tnf抑制剂和pdc-iv抑制剂的喹啉甲酰胺类化合物 | |
CN1589256A (zh) | 盐酸舍曲林的新多晶型物和含有它们的组合物,制备盐酸舍曲林多晶型物和无定形物的新方法 | |
CN1234023A (zh) | 作为多巴胺d2激动剂和5ht1a的配位体的4-氨基乙氧基吲哚 | |
US7417165B2 (en) | Crystalline forms of pregabalin | |
CN1276783A (zh) | 2-苯氧基苯胺衍生物 | |
CN1753886A (zh) | 多元碱化合物的酸加成盐的制造方法 | |
CN1359389A (zh) | 美拉加川的实质性结晶形式 | |
CN1422244A (zh) | 制备胺衍生物的方法 | |
CN1886371A (zh) | 氟伐他汀钠多晶型物的制备方法 | |
JP2005532356A (ja) | 塩酸フェキソフェナジンの多型体xvi | |
CN1244582C (zh) | 喹诺酮羧酸类化合物及其制备方法和医药用途 | |
CN1733727A (zh) | 结晶卡维地洛、其制备方法、药物组合物和制药用途 | |
CN1183115C (zh) | 5-氨基-8-甲氧基喹诺酮羧酸类衍生物及其制法 | |
CN1788004A (zh) | 缬沙坦的多晶型 | |
CN1265652A (zh) | 用作速激肽受体拮抗剂的2-酰基氨基丙胺化合物 | |
CN1612874A (zh) | 罗格列酮乙二磺酸盐和它们作为抗糖尿病药物的用途 | |
KR20070088507A (ko) | 카베딜올의 결정질 형태 및 이것의 제조 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |