NO329710B1 - Carvedilolfosfatsalter og/eller solvater derav, samt farmasoytiske preparater omfattende disse - Google Patents
Carvedilolfosfatsalter og/eller solvater derav, samt farmasoytiske preparater omfattende disse Download PDFInfo
- Publication number
- NO329710B1 NO329710B1 NO20050427A NO20050427A NO329710B1 NO 329710 B1 NO329710 B1 NO 329710B1 NO 20050427 A NO20050427 A NO 20050427A NO 20050427 A NO20050427 A NO 20050427A NO 329710 B1 NO329710 B1 NO 329710B1
- Authority
- NO
- Norway
- Prior art keywords
- carvedilol
- dihydrogen phosphate
- theta
- solvates
- degrees
- Prior art date
Links
- 239000012453 solvate Substances 0.000 title claims abstract description 38
- LHNYXTULDSJZRB-UHFFFAOYSA-N 1-(9h-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol;phosphoric acid;hydrate Chemical class O.OP(O)(O)=O.OP(O)(O)=O.COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2.COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 LHNYXTULDSJZRB-UHFFFAOYSA-N 0.000 title abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229960004195 carvedilol Drugs 0.000 claims abstract description 98
- OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 claims abstract description 93
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 45
- CKRORYDHXIRZCH-UHFFFAOYSA-N phosphoric acid;dihydrate Chemical compound O.O.OP(O)(O)=O CKRORYDHXIRZCH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- LBDROUOCQSGOFI-UHFFFAOYSA-N methanol;phosphoric acid Chemical group OC.OP(O)(O)=O LBDROUOCQSGOFI-UHFFFAOYSA-N 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 abstract description 7
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 abstract description 5
- 206010019280 Heart failures Diseases 0.000 abstract description 5
- 206010020772 Hypertension Diseases 0.000 abstract description 5
- 238000001228 spectrum Methods 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000005079 FT-Raman Methods 0.000 description 9
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- -1 carvedilol hydrogen phosphates Chemical class 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 229960000370 carvedilol phosphate Drugs 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 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 4
- 229930006000 Sucrose Natural products 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000012458 free base Substances 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
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 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 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 238000002076 thermal analysis method Methods 0.000 description 3
- 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 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000008791 TOSS pulse sequence Methods 0.000 description 1
- 238000004474 TOSS sequence Methods 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000011161 development Methods 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
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007887 hard shell capsule Substances 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 238000000449 magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007886 soft shell capsule Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004481 total suppression of sideband Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39217502P | 2002-06-27 | 2002-06-27 | |
| PCT/US2003/020408 WO2004002419A2 (en) | 2002-06-27 | 2003-06-27 | Carvedilol phosphate salts and/or solvates thereof, correspondinq compositions, and/or methods of treatment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20050427L NO20050427L (no) | 2005-01-25 |
| NO329710B1 true NO329710B1 (no) | 2010-12-06 |
Family
ID=30000823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20050427A NO329710B1 (no) | 2002-06-27 | 2005-01-25 | Carvedilolfosfatsalter og/eller solvater derav, samt farmasoytiske preparater omfattende disse |
Country Status (15)
| Country | Link |
|---|---|
| US (6) | US7268156B2 (ja) |
| EP (1) | EP1534270A4 (ja) |
| JP (3) | JP2005533823A (ja) |
| KR (3) | KR20140006111A (ja) |
| CN (6) | CN103254114A (ja) |
| AU (1) | AU2003248746B2 (ja) |
| BR (1) | BR0312102A (ja) |
| CA (1) | CA2492060C (ja) |
| EA (1) | EA008384B1 (ja) |
| IL (1) | IL165814A (ja) |
| MX (1) | MXPA04012923A (ja) |
| NO (1) | NO329710B1 (ja) |
| NZ (1) | NZ537161A (ja) |
| WO (1) | WO2004002419A2 (ja) |
| ZA (1) | ZA200410011B (ja) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002000216A1 (en) * | 2000-06-28 | 2002-01-03 | Teva Pharmaceutical Industries Ltd. | 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 |
| 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 |
| 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 |
| 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 |
| CA2498777C (en) | 2002-09-13 | 2015-01-13 | Replicor, Inc. | Non-sequence complementary antiviral oligonucleotides |
| 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 |
| 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 |
| 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 |
| WO2006135757A1 (en) * | 2005-06-09 | 2006-12-21 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of carvedilol and processes for their preparation |
| US8344159B2 (en) | 2006-06-14 | 2013-01-01 | Mylan Laboratories Limited | Carvedilol phosphate sesquihydrate |
| EP1991527A2 (en) * | 2006-06-28 | 2008-11-19 | Teva Pharmaceutical Industries Ltd | Polymorphous forms of carvedilol phosphate |
| US20090028935A1 (en) * | 2006-12-01 | 2009-01-29 | Kristin Arnold | Carvedilol forms, compositions, and methods of preparation thereof |
| US20080292695A1 (en) * | 2006-12-01 | 2008-11-27 | Kristin Arnold | Carvedilol forms, compositions, and methods of preparation thereof |
| WO2008084494A1 (en) * | 2007-01-08 | 2008-07-17 | Matrix Laboratories Limited | Novel polymorphic forms of carvedilol dihydrogen phosphate and process for preparing the same |
| WO2008105794A1 (en) * | 2007-02-26 | 2008-09-04 | Teva Pharmaceutical Industries Ltd. | Process for the purification of carvedilol or its salts thereof |
| WO2008104990A1 (en) * | 2007-02-27 | 2008-09-04 | Lupin Limited | Amorphous carvedilol dihydrogen phosphate |
| US20080249317A1 (en) * | 2007-04-04 | 2008-10-09 | Apotex Inc. | Novel amorphous form of carvedilol phosphate and processes for the preparation thereof |
| WO2008142703A1 (en) * | 2007-05-17 | 2008-11-27 | Wanbury Limited | A novel cost effective process for production of carvedilol phosphate |
| EP2014649A1 (en) * | 2007-06-27 | 2009-01-14 | Inke, S.A. | Novel amorphous carvedilol dihydrogen phosphate |
| WO2009008009A1 (en) * | 2007-07-11 | 2009-01-15 | Lupin Limited | Novel crystalline form b of carvedilol dihydrogen phosphate |
| US20100076047A1 (en) * | 2007-08-20 | 2010-03-25 | Sankar Reddy Budidet | Amorphous 1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol phosphate salt |
| US8278461B2 (en) | 2007-08-21 | 2012-10-02 | Lupin Limited | Stable amorphous form of carvedilol dihydrogen phosphate with stabilizer |
| US20090076283A1 (en) * | 2007-09-07 | 2009-03-19 | Scinopharm Taiwan Ltd. | Method of crystallizing carvedilol phosphate and the product thereof |
| US20090111998A1 (en) * | 2007-10-25 | 2009-04-30 | Srinivas Reddy Gade | Process for the preparation of carvedilol dihydrogen phosphate hemihydrate and pharmaceutical compositions thereof |
| WO2009122425A1 (en) * | 2008-04-04 | 2009-10-08 | Shodhana Laboratories Limited | Novel crystalline form of carvedilol dihydrogen phosphate and related processes |
| US7763645B2 (en) * | 2008-05-23 | 2010-07-27 | Wanbury Limited | Carvedilol dihydrogen phosphate monohydrate |
| CN101891671B (zh) * | 2010-07-26 | 2012-06-27 | 天津大学 | 一种卡维地洛磷酸二氢盐的晶体及其制备方法 |
| US8492426B1 (en) | 2012-07-12 | 2013-07-23 | Anis Ahmad | Use of carvedilol for treatment of diabetes mellitus |
| CN106892858A (zh) * | 2015-12-21 | 2017-06-27 | 上海科胜药物研发有限公司 | 一种卡维地洛磷酸二氢盐新晶型 |
| US10357476B1 (en) | 2018-10-30 | 2019-07-23 | Anis Ahmad | Method for treating coronary artery disease |
| CN110279662A (zh) * | 2019-06-05 | 2019-09-27 | 合肥合源药业有限公司 | 一种难溶性药物卡维地洛的固体分散体及制备方法和应用 |
| US10772869B1 (en) | 2019-07-24 | 2020-09-15 | ECI Pharmaceuticals, LLC | Pharmaceutical compositions including carvedilol and methods of using the same |
Family Cites Families (53)
| 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 |
| US4053067A (en) * | 1973-06-25 | 1977-10-11 | Westinghouse Electric Corporation | Fuel transfer system for a nuclear reactor |
| 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 |
| US4985464A (en) | 1984-05-23 | 1991-01-15 | Rudolf Happle | Drug compositions for local treatment of alopecia areata |
| US5405863A (en) | 1992-12-01 | 1995-04-11 | Smithkline Beecham Corporation | Antioxidant cardioprotective use of, and method of treatment using, hydroxycarbazole compounds |
| US5308862A (en) | 1993-03-05 | 1994-05-03 | Boehringer Mannheim Pharmaceuticals Corporation - Smithkline Beecham Corp., Ltd. Partnership No. 1 | Use of, and method of treatment using, carbazolyl-(4)-oxypropanolamine compounds for inhibition of smooth muscle cell proliferation |
| US5393772A (en) | 1993-11-24 | 1995-02-28 | Boehringer Mannheim Pharmaceuticals Corporation | Use of, and method of treatment using, hydroxycarbazole compounds for inhibition of smooth muscle migration and proliferation |
| 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 |
| US20010011099A1 (en) | 1995-05-30 | 2001-08-02 | Smithkline Beecham Corporation | Antioxidant neuroprotective use of, and method of treatment using, hydroxycarbazole compounds |
| WO1998002157A1 (de) | 1996-07-13 | 1998-01-22 | Roche Diagnostics Gmbh | Topisch einsetzbare pharmazeutische formulierungen enthaltend als wirkstoff ein carbazolyl-(4)-oxy-propanolamin-derivat |
| AU4083097A (en) | 1996-08-23 | 1998-03-06 | Boehringer Mannheim Pharmaceuticals Corporation-Smithkline Beecham Corporation Limited Partnership No. 1 | Method for inhibiting the expression of fas |
| PL332638A1 (en) | 1996-10-09 | 1999-09-27 | Boehringer Mannheim Pharm Corp | Method of inhibiting stress-activated proteinous kinases |
| 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 |
| 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 |
| GT199800126A (es) | 1997-08-29 | 2000-01-29 | Terapia de combinacion. | |
| ZA989365B (en) | 1997-10-15 | 1999-04-15 | Boehringer Mannheim Pharm Corp | Preparation for treating alzheimer's disease |
| US20020054911A1 (en) | 2000-05-11 | 2002-05-09 | Boehringer Mannheim Pharmaceutical Corporation-Sm Ithkline Beckman Corporation, Limited Partnershi | Novel oral dosage form for carvedilol |
| US6541479B1 (en) | 1997-12-02 | 2003-04-01 | Massachusetts College Of Pharmacy | Calcium channel blockers |
| US6852337B2 (en) | 1998-04-09 | 2005-02-08 | Roche Diagnostics Gmbh | Carvedilol-galenics |
| EP1069896B1 (en) | 1998-04-09 | 2003-08-06 | Roche Diagnostics GmbH | Carvedilol-galenics |
| DE19833119A1 (de) | 1998-07-23 | 2000-01-27 | Roche Diagnostics Gmbh | Spritzfertige Injektionslösungen enthaltend Carvedilol |
| US6664284B2 (en) | 1998-07-23 | 2003-12-16 | Roche Diagnostics Gmbh | Stabilized carvedilol injection solution |
| PE20001302A1 (es) | 1998-11-27 | 2000-11-30 | Hoffmann La Roche | Preparaciones de una combinacion farmaceutica que contiene carvedilol e hidroclorotiazida |
| AU1657001A (en) * | 1999-11-15 | 2001-05-30 | Smithkline Beecham Corporation | Carvedilol methanesulfonate |
| EP1106210A3 (en) | 1999-12-07 | 2003-12-03 | Pfizer Products Inc. | Combination of aldose reductase inhibitors and antihypertensive agents for the treatment of diabetic complications |
| US20010036959A1 (en) * | 2000-04-03 | 2001-11-01 | Gabel Rolf Dieter | Carvedilol-hydrophilic solutions |
| DE60105996T2 (de) | 2000-04-03 | 2006-03-09 | F. Hoffmann-La Roche Ag | Konzentrierte lösungen von carvedilol |
| AU5066101A (en) | 2000-04-13 | 2001-10-30 | Synthon B.V. | Modified release formulations containing a hypnotic agent |
| DK174645B1 (da) * | 2000-05-18 | 2003-08-04 | Gea Farmaceutisk Fabrik As | Fremgangsmåde og mellemprodukter til fremstillingen af 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxy-phenoxy)-ethylamino]-propan-2-ol, carvedilol og syreadditionssalte deraf |
| WO2002000216A1 (en) | 2000-06-28 | 2002-01-03 | Teva Pharmaceutical Industries Ltd. | Carvedilol |
| US20020099013A1 (en) | 2000-11-14 | 2002-07-25 | Thomas Piccariello | Active agent delivery systems and methods for protecting and administering active agents |
| EP1385509A4 (en) | 2001-04-02 | 2004-06-30 | Smithkline Beecham Corp | TREATMENT METHOD |
| IN191028B (ja) | 2001-05-17 | 2003-09-13 | Sun Pharmaceutical Ind Ltd | |
| FI20011464A0 (fi) | 2001-07-04 | 2001-07-04 | Orion Corp | Yhdistelmäterapia sydämen vajaatoiminnan hoitoon |
| WO2003024426A1 (en) | 2001-09-21 | 2003-03-27 | Egalet A/S | Controlled release solid dispersions |
| US20040234602A1 (en) | 2001-09-21 | 2004-11-25 | Gina Fischer | Polymer release system |
| DE60221683T2 (de) | 2001-09-28 | 2008-04-30 | F. Hoffmann-La Roche Ag | Pseudopolymorphe formen von carvedilol |
| WO2003028645A2 (en) | 2001-10-01 | 2003-04-10 | Smithkline Beecham Corporation | Novel compositions of carvedilol |
| WO2003028718A1 (en) | 2001-10-01 | 2003-04-10 | Smithkline Beecham Corporation | Novel formulations of carvedilol |
| WO2003028649A2 (en) | 2001-10-02 | 2003-04-10 | Smithkline Beecham Corporation | Novel composition of carvedilol |
| US20040019096A1 (en) | 2001-10-23 | 2004-01-29 | Vlassios Andronis | Novel formulations of 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 |
| EP1499310A4 (en) * | 2002-04-30 | 2005-12-07 | Sb Pharmco Inc | MONOCITRATE MONOHYDRATE OF CARVEDILOL |
| 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 |
| JP2005533846A (ja) | 2002-07-22 | 2005-11-10 | ナノハイブリッド カンパニー リミテッド | イトラコナゾール、シクロスポリン、またはカルベジロールと層状型珪酸塩との混成体及びその製造方法 |
| ES2204303B2 (es) * | 2002-08-07 | 2004-12-16 | Laboratorios Vita, S.A. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo. |
| EP1530458A1 (en) | 2002-08-14 | 2005-05-18 | Ranbaxy Laboratories, Ltd. | Extended release matrix tablets |
| US20040151772A1 (en) | 2002-11-08 | 2004-08-05 | Egalet A/S | Controlled release carvedilol compositions |
| AU2003288608A1 (en) | 2002-12-20 | 2004-07-14 | Ranbaxy Laboratories Limited | Controlled release, multiple unit drug delivery systems |
| 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 |
| 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 |
-
2003
- 2003-06-27 CN CN2013100984294A patent/CN103254114A/zh active Pending
- 2003-06-27 JP JP2004518025A patent/JP2005533823A/ja not_active Withdrawn
- 2003-06-27 BR BRPI0312102-0A patent/BR0312102A/pt not_active Application Discontinuation
- 2003-06-27 CN CN2013100984468A patent/CN103333099A/zh active Pending
- 2003-06-27 KR KR1020137033808A patent/KR20140006111A/ko not_active Application Discontinuation
- 2003-06-27 NZ NZ537161A patent/NZ537161A/en not_active IP Right Cessation
- 2003-06-27 CN CN201010152481XA patent/CN101898995B/zh not_active Expired - Lifetime
- 2003-06-27 CN CN2013100984947A patent/CN103288714A/zh active Pending
- 2003-06-27 EA EA200500091A patent/EA008384B1/ru not_active IP Right Cessation
- 2003-06-27 CA CA2492060A patent/CA2492060C/en not_active Expired - Lifetime
- 2003-06-27 WO PCT/US2003/020408 patent/WO2004002419A2/en active Application Filing
- 2003-06-27 EP EP03762176A patent/EP1534270A4/en not_active Ceased
- 2003-06-27 KR KR1020117028711A patent/KR20110134952A/ko not_active Application Discontinuation
- 2003-06-27 AU AU2003248746A patent/AU2003248746B2/en not_active Expired
- 2003-06-27 US US10/518,654 patent/US7268156B2/en not_active Expired - Lifetime
- 2003-06-27 KR KR1020137008295A patent/KR101468827B1/ko active IP Right Grant
- 2003-06-27 CN CN2013100986020A patent/CN103288715A/zh active Pending
- 2003-06-27 CN CNA038202301A patent/CN1678305A/zh active Pending
- 2003-06-27 MX MXPA04012923A patent/MXPA04012923A/es active IP Right Grant
-
2004
- 2004-12-10 ZA ZA200410011A patent/ZA200410011B/xx unknown
- 2004-12-16 IL IL165814A patent/IL165814A/en not_active IP Right Cessation
-
2005
- 2005-01-25 NO NO20050427A patent/NO329710B1/no not_active IP Right Cessation
-
2007
- 2007-06-25 US US11/767,586 patent/US7902378B2/en not_active Expired - Lifetime
- 2007-06-25 US US11/767,578 patent/US7893100B2/en active Active
- 2007-06-25 US US11/767,581 patent/US7759384B2/en not_active Expired - Lifetime
- 2007-06-25 US US11/767,573 patent/US7626041B2/en not_active Expired - Lifetime
- 2007-06-25 US US11/767,566 patent/US20070259940A1/en not_active Abandoned
-
2010
- 2010-12-17 JP JP2010282048A patent/JP5422545B2/ja not_active Expired - Lifetime
-
2013
- 2013-08-02 JP JP2013161656A patent/JP2013241450A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO329710B1 (no) | Carvedilolfosfatsalter og/eller solvater derav, samt farmasoytiske preparater omfattende disse | |
| CS196290B2 (en) | Process for preparing new compounds | |
| JP2007512372A (ja) | 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 | |
| RU2717564C2 (ru) | Кристаллические формы 1-((2r,4r)-2-(1h-бензо[d]имидазол-2-ил)-1-метилпиперидин 4-ил)-3-(4-цианофенил)мочевины малеата | |
| EP3243824A1 (en) | Solid forms of ibrutinib free base | |
| US6492556B2 (en) | Form A of fluoxetine hydrochloride | |
| US6258853B1 (en) | Form a of fluoxetine hydrochloride | |
| KR20050019792A (ko) | 카베딜롤 인산염 및(또는) 그의 용매화물, 상응하는조성물, 및(또는) 치료 방법 | |
| US6310250B1 (en) | Form A of fluoxetine hydrochloride | |
| NO865179L (no) | Fremgangsmaate for fremstilling av optisk aktive 2-klor-12-(3-dimethylamino-2-methylpropyl)-12h-dibenzo(d,g)(1,3,6)dioxazociner. | |
| US6310251B1 (en) | Form a of fluoxetine hydrochloride | |
| US6313350B1 (en) | Form a of fluoxetine hydrochloride | |
| EP3368506A1 (en) | Process for the preparation of enclomiphene citrate having needle shaped crystal habit. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |