JP2008510754A - レルカニジピンの塩 - Google Patents
レルカニジピンの塩 Download PDFInfo
- Publication number
- JP2008510754A JP2008510754A JP2007528715A JP2007528715A JP2008510754A JP 2008510754 A JP2008510754 A JP 2008510754A JP 2007528715 A JP2007528715 A JP 2007528715A JP 2007528715 A JP2007528715 A JP 2007528715A JP 2008510754 A JP2008510754 A JP 2008510754A
- Authority
- JP
- Japan
- Prior art keywords
- lercanidipine
- acid
- salt
- crystalline
- amorphous
- 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.)
- Abandoned
Links
- ZDXUKAKRHYTAKV-UHFFFAOYSA-N lercanidipine Chemical class COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZDXUKAKRHYTAKV-UHFFFAOYSA-N 0.000 title claims abstract description 162
- 229960004294 lercanidipine Drugs 0.000 claims abstract description 127
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 150000002500 ions Chemical class 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 claims description 15
- 229960002162 lercanidipine hydrochloride Drugs 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229940114081 cinnamate Drugs 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229960001860 salicylate Drugs 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 claims description 3
- 229940116871 l-lactate Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 claims 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract description 2
- 150000003460 sulfonic acids Chemical class 0.000 abstract description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- 235000002639 sodium chloride Nutrition 0.000 description 51
- 239000002904 solvent Substances 0.000 description 40
- 239000013078 crystal Substances 0.000 description 32
- 239000012458 free base Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000011550 stock solution Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000002178 crystalline material Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- -1 Methyl 1,1, N-trimethyl-N- (3,3-diphenylpropyl) -2-aminoethyl 1,4-dihydro-2,6-dimethyl-4- (3-nitrophenyl) -pyridine Chemical compound 0.000 description 8
- 238000001069 Raman spectroscopy Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 7
- 229940092714 benzenesulfonic acid Drugs 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 238000012216 screening Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000005079 FT-Raman Methods 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 238000001237 Raman spectrum Methods 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection 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
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007614 solvation Methods 0.000 description 3
- 235000010487 tragacanth Nutrition 0.000 description 3
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- 239000006211 transdermal dosage form Substances 0.000 description 3
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 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 2
- 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 2
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- 108010010803 Gelatin Proteins 0.000 description 2
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60414904P | 2004-08-24 | 2004-08-24 | |
| PCT/EP2005/009043 WO2006021397A1 (en) | 2004-08-24 | 2005-08-22 | Lercanidipine salts |
Publications (2)
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| JP2008510754A true JP2008510754A (ja) | 2008-04-10 |
| JP2008510754A5 JP2008510754A5 (enExample) | 2008-10-09 |
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| JP2007528715A Abandoned JP2008510754A (ja) | 2004-08-24 | 2005-08-22 | レルカニジピンの塩 |
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| EP (1) | EP1799644B1 (enExample) |
| JP (1) | JP2008510754A (enExample) |
| KR (1) | KR20070045351A (enExample) |
| CN (1) | CN101048379A (enExample) |
| AR (1) | AR050467A1 (enExample) |
| AU (1) | AU2005276619B2 (enExample) |
| BR (1) | BRPI0514606A (enExample) |
| CA (1) | CA2575078A1 (enExample) |
| EA (1) | EA011773B1 (enExample) |
| ES (1) | ES2462921T3 (enExample) |
| IL (1) | IL180905A0 (enExample) |
| MX (1) | MX2007002141A (enExample) |
| NO (1) | NO20071515L (enExample) |
| NZ (1) | NZ553127A (enExample) |
| PE (1) | PE20060629A1 (enExample) |
| TW (1) | TW200613275A (enExample) |
| WO (1) | WO2006021397A1 (enExample) |
| ZA (1) | ZA200702364B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023219106A1 (ja) * | 2022-05-10 | 2023-11-16 | Ｍｙｒｏｄｉａ Ｔｈｅｒａｐｅｕｔｉｃｓ株式会社 | ２－メチル－２－チアゾリンの塩 |
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| SI1953162T1 (sl) * | 2001-02-24 | 2012-09-28 | Boehringer Ingelheim Pharma | Ksantinski derivati, njihova priprava in njihova uporaba kot zdravila |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| AR053023A1 (es) * | 2005-02-25 | 2007-04-18 | Recordati Ireland Ltd | Base libre de lercanidipina, metodos para su preparacion y composiciones farmaceuticas que las contienen |
| AR052918A1 (es) * | 2005-02-25 | 2007-04-11 | Recordati Ireland Ltd | Clorhidrato de lercanidipina amorfo |
| DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| BRPI0711558A2 (pt) | 2006-05-04 | 2011-11-08 | Boeringer Ingelheim Internat Gmbh | polimorfos |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| AU2007257882B2 (en) | 2006-06-12 | 2011-09-08 | Secura Bio Inc. | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
| WO2008040367A1 (en) * | 2006-08-01 | 2008-04-10 | Union Quimico-Farmaceutica S.A. | Lercanidipine hydrobromide, a process for its preparation, crystalline forms and compositions thereof |
| US20080175872A1 (en) * | 2006-09-28 | 2008-07-24 | Osmotica Corp. | Controlled Release Dosage Form Containing Lercanidipine and a Performance-enhancing Acid |
| ES2306595B1 (es) * | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| WO2008112313A2 (en) * | 2007-03-14 | 2008-09-18 | Teva Pharmaceutical Industries Ltd. | Processes for preparing solid states of o-desmethylvenlafaxine succinate |
| WO2009017813A1 (en) * | 2007-08-02 | 2009-02-05 | Teva Pharmaceutical Industries Ltd. | O-desmethyl venlafaxine saccharinate |
| KR101343027B1 (ko) | 2007-11-26 | 2013-12-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | Ｏ-데스메틸벤라팍신 푸마레이트의 결정형 |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| CA3108961C (en) * | 2008-08-01 | 2024-07-02 | Hospira, Inc. | Pharmaceutical compositions comprising clevidipine and methods for producing low concentrations of impurities thereof |
| CN102186351A (zh) * | 2008-08-01 | 2011-09-14 | 医药公司 | 药物组合物和用于稳定药物组合物的方法 |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| AU2009290911A1 (en) | 2008-09-10 | 2010-03-18 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| EP2382216A1 (en) | 2008-12-23 | 2011-11-02 | Boehringer Ingelheim International GmbH | Salt forms of organic compound |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| EA034869B1 (ru) | 2009-11-27 | 2020-03-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин |
| CA2795023A1 (en) * | 2010-03-29 | 2011-10-06 | Pliva Hrvatska D.O.O. | Crystal forms of o-desmethylvenlafaxine fumarate |
| MX341025B (es) | 2010-05-05 | 2016-08-04 | Boehringer Ingelheim Int Gmbh * | Terapia de combinacion. |
| PH12012502524A1 (en) | 2010-06-24 | 2014-02-10 | Boehringer Ingelheim Int | Diabetes therapy |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| EP3517539B1 (en) | 2011-07-15 | 2022-12-14 | Boehringer Ingelheim International GmbH | Substituted dimeric quinazoline derivative, its preparation and its use in pharmaceutical compositions for the treatment of type i and ii diabetes |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| JP6224084B2 (ja) | 2012-05-14 | 2017-11-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| US20130303554A1 (en) | 2012-05-14 | 2013-11-14 | Boehringer Ingelheim International Gmbh | Use of a dpp-4 inhibitor in sirs and/or sepsis |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB8403866D0 (en) * | 1984-02-14 | 1984-03-21 | Recordati Chem Pharm | Diphenylalkylaminoalkyl esters |
| US5767136A (en) | 1995-05-12 | 1998-06-16 | Recordati, S.A. Chemical And Pharmaceutical Company | 1,4-Dihydropyridines useful for prevention or reduction of atherosclerotic lesions on arterial walls |
| IT1275532B (it) * | 1995-07-14 | 1997-08-07 | Recordati Chem Pharm | Uso di derivati 1,4-diidropiridinici per la prevenzione e la terapia della degenerazione aterosclerotica della parete arteriosa |
| US5696139A (en) | 1995-05-12 | 1997-12-09 | Recordati S.A., Chemical And Pharmaceutical Company | Use of S-enantiomers of 1,4-dihydropyridine derivatives for treating heart failure |
| IT1301759B1 (it) * | 1998-06-19 | 2000-07-07 | Nicox Sa | Sali nitrati di farmaci antiipertensivi |
| US20030069285A1 (en) | 2001-08-06 | 2003-04-10 | Recordati Ireland Limited | Novel solvate and crystalline forms of lercanidipine hydrochloride |
| US6852737B2 (en) | 2001-08-06 | 2005-02-08 | Recordati Ireland Limited | Crude and crystalline forms of lercanidipine hydrochloride |
| US6699892B2 (en) * | 2002-06-04 | 2004-03-02 | Yung Shin Pharmaceutical Industrial Co., Ltd. | Pharmaceutically acceptable salt of amlodipine and method of preparing the same |
| WO2004035051A1 (en) * | 2002-10-16 | 2004-04-29 | Recordati Ireland Limited | Lisinopril/lercanidipine combination therapy |
| US20040198789A1 (en) * | 2003-02-28 | 2004-10-07 | Recordati Ireland Limited | Lercanidipine/ARB/diuretic therapeutic combinations |
-
2005
- 2005-08-19 TW TW094128384A patent/TW200613275A/zh unknown
- 2005-08-22 WO PCT/EP2005/009043 patent/WO2006021397A1/en not_active Ceased
- 2005-08-22 BR BRPI0514606-2A patent/BRPI0514606A/pt not_active IP Right Cessation
- 2005-08-22 AU AU2005276619A patent/AU2005276619B2/en not_active Ceased
- 2005-08-22 PE PE2005000963A patent/PE20060629A1/es not_active Application Discontinuation
- 2005-08-22 EA EA200700492A patent/EA011773B1/ru not_active IP Right Cessation
- 2005-08-22 CA CA002575078A patent/CA2575078A1/en not_active Abandoned
- 2005-08-22 EP EP05776228.8A patent/EP1799644B1/en not_active Expired - Lifetime
- 2005-08-22 NZ NZ553127A patent/NZ553127A/xx not_active IP Right Cessation
- 2005-08-22 MX MX2007002141A patent/MX2007002141A/es not_active Application Discontinuation
- 2005-08-22 AR ARP050103516A patent/AR050467A1/es not_active Application Discontinuation
- 2005-08-22 JP JP2007528715A patent/JP2008510754A/ja not_active Abandoned
- 2005-08-22 KR KR1020077006715A patent/KR20070045351A/ko not_active Withdrawn
- 2005-08-22 CN CNA2005800284676A patent/CN101048379A/zh active Pending
- 2005-08-22 ES ES05776228.8T patent/ES2462921T3/es not_active Expired - Lifetime
- 2005-08-24 US US11/211,769 patent/US7683179B2/en not_active Expired - Fee Related
-
2007
- 2007-01-23 IL IL180905A patent/IL180905A0/en unknown
- 2007-03-22 ZA ZA200702364A patent/ZA200702364B/xx unknown
- 2007-03-23 NO NO20071515A patent/NO20071515L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023219106A1 (ja) * | 2022-05-10 | 2023-11-16 | Ｍｙｒｏｄｉａ Ｔｈｅｒａｐｅｕｔｉｃｓ株式会社 | ２－メチル－２－チアゾリンの塩 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200613275A (en) | 2006-05-01 |
| EP1799644B1 (en) | 2014-02-12 |
| PE20060629A1 (es) | 2006-08-11 |
| ES2462921T3 (es) | 2014-05-26 |
| KR20070045351A (ko) | 2007-05-02 |
| EA011773B1 (ru) | 2009-06-30 |
| AR050467A1 (es) | 2006-10-25 |
| ZA200702364B (en) | 2008-09-25 |
| EA200700492A1 (ru) | 2007-08-31 |
| CA2575078A1 (en) | 2006-03-02 |
| IL180905A0 (en) | 2007-07-04 |
| US7683179B2 (en) | 2010-03-23 |
| NO20071515L (no) | 2007-05-22 |
| US20060047125A1 (en) | 2006-03-02 |
| WO2006021397A1 (en) | 2006-03-02 |
| AU2005276619B2 (en) | 2009-04-30 |
| EP1799644A1 (en) | 2007-06-27 |
| BRPI0514606A (pt) | 2008-06-17 |
| NZ553127A (en) | 2009-07-31 |
| MX2007002141A (es) | 2007-04-27 |
| CN101048379A (zh) | 2007-10-03 |
| AU2005276619A1 (en) | 2006-03-02 |
| WO2006021397A8 (en) | 2006-04-27 |
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