KR20060017616A - 결정형 β2 아드레날린 수용체 작용제 - Google Patents
결정형 β2 아드레날린 수용체 작용제 Download PDFInfo
- Publication number
- KR20060017616A KR20060017616A KR1020057022542A KR20057022542A KR20060017616A KR 20060017616 A KR20060017616 A KR 20060017616A KR 1020057022542 A KR1020057022542 A KR 1020057022542A KR 20057022542 A KR20057022542 A KR 20057022542A KR 20060017616 A KR20060017616 A KR 20060017616A
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- South Korea
- Prior art keywords
- compound
- hydroxy
- solution
- phenyl
- formamido
- 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.)
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- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 title 2
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 230000000694 effects Effects 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 86
- 239000000243 solution Substances 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000003814 drug Substances 0.000 claims description 35
- -1 anticholinergic Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 229940124597 therapeutic agent Drugs 0.000 claims description 21
- 239000002002 slurry Substances 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 18
- 239000002798 polar solvent Substances 0.000 claims description 18
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 16
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 14
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 13
- 239000012458 free base Substances 0.000 claims description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 9
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 9
- 208000019693 Lung disease Diseases 0.000 claims description 9
- 239000003246 corticosteroid Substances 0.000 claims description 9
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 239000007864 aqueous solution Substances 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
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- 238000002835 absorbance Methods 0.000 claims description 4
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- 229910001504 inorganic chloride Inorganic materials 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- MBMJDELICBDLEE-UHFFFAOYSA-N ethanamine;dihydrochloride Chemical compound Cl.Cl.CCN MBMJDELICBDLEE-UHFFFAOYSA-N 0.000 claims 1
- FPYUZAPSZIWCQR-UHFFFAOYSA-N n-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]formamide Chemical compound NCC(O)C1=CC=C(O)C(NC=O)=C1 FPYUZAPSZIWCQR-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 34
- 238000002360 preparation method Methods 0.000 abstract description 20
- 239000000048 adrenergic agonist Substances 0.000 abstract description 11
- 229940126157 adrenergic receptor agonist Drugs 0.000 abstract description 11
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 abstract 3
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 89
- 239000000203 mixture Substances 0.000 description 68
- 229940125904 compound 1 Drugs 0.000 description 58
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 238000009472 formulation Methods 0.000 description 32
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 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 11
- JFBRPCNADZNVNO-UHFFFAOYSA-N N-[5-[2-(hydroxyamino)ethyl]-2-phenylmethoxyphenyl]formamide Chemical compound ONCCC1=CC(=C(C=C1)OCC1=CC=CC=C1)NC=O JFBRPCNADZNVNO-UHFFFAOYSA-N 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 8
- QQPHRRSYJMOQOC-DKIIUIKKSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[[(2r)-2-hydroxy-2-phenylethyl]amino]phenyl]ethylamino]ethyl]phenyl]formamide;hydrochloride Chemical compound Cl.C1([C@@H](O)CNC2=CC=C(C=C2)CCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=CC=CC=C1 QQPHRRSYJMOQOC-DKIIUIKKSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 229940011051 isopropyl acetate Drugs 0.000 description 7
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 238000001816 cooling Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003380 propellant Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- BMKINZUHKYLSKI-DQEYMECFSA-N n-[2-hydroxy-5-[(1r)-1-hydroxy-2-[2-[4-[[(2r)-2-hydroxy-2-phenylethyl]amino]phenyl]ethylamino]ethyl]phenyl]formamide Chemical compound C1([C@@H](O)CNC2=CC=C(C=C2)CCNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)=CC=CC=C1 BMKINZUHKYLSKI-DQEYMECFSA-N 0.000 description 5
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 5
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 5
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US47342303P | 2003-05-27 | 2003-05-27 | |
| US60/473,423 | 2003-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060017616A true KR20060017616A (ko) | 2006-02-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057022542A Ceased KR20060017616A (ko) | 2003-05-27 | 2004-05-26 | 결정형 β2 아드레날린 수용체 작용제 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7557247B2 (enExample) |
| EP (1) | EP1641744A2 (enExample) |
| JP (1) | JP2007500233A (enExample) |
| KR (1) | KR20060017616A (enExample) |
| CN (1) | CN100528835C (enExample) |
| AR (1) | AR045317A1 (enExample) |
| AU (1) | AU2004243304A1 (enExample) |
| BR (1) | BRPI0410705A (enExample) |
| CA (1) | CA2525839A1 (enExample) |
| CO (1) | CO5650226A2 (enExample) |
| IS (1) | IS8111A (enExample) |
| MA (1) | MA27779A1 (enExample) |
| MX (1) | MXPA05012678A (enExample) |
| NO (1) | NO20056132L (enExample) |
| NZ (1) | NZ543355A (enExample) |
| RU (1) | RU2005140652A (enExample) |
| TW (1) | TW200510277A (enExample) |
| WO (1) | WO2004106279A2 (enExample) |
| ZA (1) | ZA200510104B (enExample) |
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| UA73965C2 (en) * | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| 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 |
| TW200510277A (en) * | 2003-05-27 | 2005-03-16 | Theravance Inc | Crystalline form of β2-adrenergic receptor agonist |
| TW200526547A (en) * | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| TW200531692A (en) * | 2004-01-12 | 2005-10-01 | Theravance Inc | Aryl aniline derivatives as β2 adrenergic receptor agonists |
| 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 |
| US7846973B2 (en) * | 2004-04-02 | 2010-12-07 | Theravance, Inc. | Chemical process and new crystalline form |
| EP1786762A2 (en) * | 2004-09-10 | 2007-05-23 | Theravance, Inc. | Amidine substituted aryl aniline compounds |
| 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 |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| 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 |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| EA030606B1 (ru) | 2006-05-04 | 2018-08-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Способы приготовления лекарственного средства, содержащего полиморфы |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| US8420286B2 (en) * | 2008-03-27 | 2013-04-16 | Xerox Corporation | Toner process |
| US8367294B2 (en) * | 2008-03-27 | 2013-02-05 | Xerox Corporation | Toner process |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| KR20200118243A (ko) | 2008-08-06 | 2020-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| MX2011002558A (es) | 2008-09-10 | 2011-04-26 | Boehringer Ingelheim Int | Terapia de combinacion para el tratamiento de diabetes y estados relacionados. |
| 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 |
| CN102256976A (zh) | 2008-12-23 | 2011-11-23 | 贝林格尔.英格海姆国际有限公司 | 有机化合物的盐形式 |
| TW201036975A (en) | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| EA034869B1 (ru) | 2009-11-27 | 2020-03-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин |
| KR101819609B1 (ko) | 2010-05-05 | 2018-01-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 체중 감소 치료에 후속하는 dpp-4 억제제에 의한 순차적 병용 요법 |
| KR20230051307A (ko) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| MX366629B (es) | 2011-07-15 | 2019-07-17 | Boehringer Ingelheim Int | Quinazolinas sustituidas, su preparación y su uso en composiciones farmacéuticas. |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| EP2849755A1 (en) | 2012-05-14 | 2015-03-25 | Boehringer Ingelheim International GmbH | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| JP6218811B2 (ja) | 2012-05-14 | 2017-10-25 | 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 | Sirs及び/又は敗血症の治療に用いるdpp−4阻害薬としてのキサンチン誘導体 |
| 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 |
| WO2015128453A1 (en) | 2014-02-28 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Medical use of a dpp-4 inhibitor |
| US10155000B2 (en) | 2016-06-10 | 2018-12-18 | Boehringer Ingelheim International Gmbh | Medical use of pharmaceutical combination or composition |
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| US676793A (en) * | 1899-09-12 | 1901-06-18 | A D Fenwick Machine Co | Pasting-machine for collars, &c. |
| US654117A (en) * | 1899-11-29 | 1900-07-17 | Henry B Maddocks | Coal-bucket. |
| US4064125A (en) * | 1976-10-29 | 1977-12-20 | E. R. Squibb And Sons, Inc. | Substituted amides having antiinflammatory activity |
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| HU196775B (en) * | 1986-08-05 | 1989-01-30 | Richter Gedeon Vegyeszet | Process for production of morfologically unique new modifications of famotidin and medical compositions containing such substances |
| US5290815A (en) | 1989-09-07 | 1994-03-01 | Glaxo Group Limited | Treatment of inflammation and allergy |
| US5872126A (en) | 1996-09-06 | 1999-02-16 | Merck & Co., Inc. | Methods and compositions for treating preterm labor |
| GB9713819D0 (en) | 1997-06-30 | 1997-09-03 | Glaxo Group Ltd | Method of reducing the systemic effects of compounds |
| SE9704644D0 (sv) | 1997-12-12 | 1997-12-12 | Astra Ab | New use |
| US6350738B1 (en) * | 1998-03-06 | 2002-02-26 | Brigham Young University | Steroid derived antibiotics |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6683115B2 (en) | 1999-06-02 | 2004-01-27 | Theravance, Inc. | β2-adrenergic receptor agonists |
| UA73965C2 (en) | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| OA11558A (en) * | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| WO2002070490A1 (en) | 2001-03-08 | 2002-09-12 | Glaxo Group Limited | Agonists of beta-adrenoceptors |
| EP1370521B1 (en) | 2001-03-22 | 2007-12-19 | Glaxo Group Limited | Formanilide derivatives as beta2-adrenoreceptor agonists |
| UA77656C2 (en) * | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| PL211953B1 (pl) | 2001-09-14 | 2012-07-31 | Glaxo Group Ltd | Pochodna fenetanoloaminy, zawierający ją środek farmaceutyczny i zastosowanie pochodnej fenetanoloaminy |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| GB0204719D0 (en) | 2002-02-28 | 2002-04-17 | Glaxo Group Ltd | Medicinal compounds |
| US7271197B2 (en) | 2002-04-25 | 2007-09-18 | Glaxo Group Limited | Phenethanolamine derivatives |
| AR040661A1 (es) * | 2002-07-26 | 2005-04-13 | Theravance Inc | Diclorhidrato cristalino de n-{2-[-((r)-2-hidroxi-2-feniletilamino)fenil]etil}-(r)-2hidroxi-2-(3-formamido-4-hidroxifenil)etilamina, agonista del receptor adrenergico beta 2 |
| TW200510277A (en) | 2003-05-27 | 2005-03-16 | Theravance Inc | Crystalline form of β2-adrenergic receptor agonist |
| US8501994B2 (en) * | 2007-08-28 | 2013-08-06 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
-
2004
- 2004-05-17 TW TW093113868A patent/TW200510277A/zh unknown
- 2004-05-24 AR ARP040101794A patent/AR045317A1/es unknown
- 2004-05-26 CA CA002525839A patent/CA2525839A1/en not_active Abandoned
- 2004-05-26 JP JP2006533430A patent/JP2007500233A/ja active Pending
- 2004-05-26 KR KR1020057022542A patent/KR20060017616A/ko not_active Ceased
- 2004-05-26 US US10/854,405 patent/US7557247B2/en not_active Expired - Lifetime
- 2004-05-26 AU AU2004243304A patent/AU2004243304A1/en not_active Abandoned
- 2004-05-26 NZ NZ543355A patent/NZ543355A/en unknown
- 2004-05-26 MX MXPA05012678A patent/MXPA05012678A/es unknown
- 2004-05-26 RU RU2005140652/04A patent/RU2005140652A/ru not_active Application Discontinuation
- 2004-05-26 BR BRPI0410705-5A patent/BRPI0410705A/pt not_active IP Right Cessation
- 2004-05-26 EP EP04753431A patent/EP1641744A2/en not_active Ceased
- 2004-05-26 WO PCT/US2004/016602 patent/WO2004106279A2/en not_active Ceased
- 2004-05-26 CN CNB200480014438XA patent/CN100528835C/zh not_active Expired - Fee Related
-
2005
- 2005-10-31 IS IS8111A patent/IS8111A/is unknown
- 2005-11-21 MA MA28612A patent/MA27779A1/fr unknown
- 2005-12-12 ZA ZA200510104A patent/ZA200510104B/xx unknown
- 2005-12-22 CO CO05129154A patent/CO5650226A2/es not_active Application Discontinuation
- 2005-12-22 NO NO20056132A patent/NO20056132L/no not_active Application Discontinuation
-
2007
- 2007-01-16 US US11/654,117 patent/US20070155990A1/en not_active Abandoned
-
2009
- 2009-05-13 US US12/465,350 patent/US7772434B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20100125150A1 (en) | 2010-05-20 |
| TW200510277A (en) | 2005-03-16 |
| RU2005140652A (ru) | 2006-04-20 |
| AU2004243304A1 (en) | 2004-12-09 |
| CO5650226A2 (es) | 2006-06-30 |
| IS8111A (is) | 2005-10-31 |
| MA27779A1 (fr) | 2006-02-01 |
| MXPA05012678A (es) | 2006-02-22 |
| WO2004106279A2 (en) | 2004-12-09 |
| US7557247B2 (en) | 2009-07-07 |
| EP1641744A2 (en) | 2006-04-05 |
| NO20056132L (no) | 2006-01-26 |
| BRPI0410705A (pt) | 2006-06-13 |
| CN100528835C (zh) | 2009-08-19 |
| CA2525839A1 (en) | 2004-12-09 |
| AR045317A1 (es) | 2005-10-26 |
| ZA200510104B (en) | 2006-11-29 |
| US7772434B2 (en) | 2010-08-10 |
| CN1795169A (zh) | 2006-06-28 |
| NZ543355A (en) | 2009-06-26 |
| JP2007500233A (ja) | 2007-01-11 |
| US20040248985A1 (en) | 2004-12-09 |
| WO2004106279A3 (en) | 2005-02-03 |
| US20070155990A1 (en) | 2007-07-05 |
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