KR20050047552A - 베타-2 작용제로서의 인돌 유도체 - Google Patents
베타-2 작용제로서의 인돌 유도체 Download PDFInfo
- Publication number
- KR20050047552A KR20050047552A KR1020057006090A KR20057006090A KR20050047552A KR 20050047552 A KR20050047552 A KR 20050047552A KR 1020057006090 A KR1020057006090 A KR 1020057006090A KR 20057006090 A KR20057006090 A KR 20057006090A KR 20050047552 A KR20050047552 A KR 20050047552A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- ethyl
- indole
- amino
- carboxamide
- 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.)
- Ceased
Links
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- 150000002475 indoles Chemical class 0.000 title abstract description 80
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 45
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- 238000000034 method Methods 0.000 claims abstract description 94
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
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- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 101
- 150000003839 salts Chemical class 0.000 claims description 71
- -1 benzyloxy, hydroxy Chemical group 0.000 claims description 62
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- 206010006451 bronchitis Diseases 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
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- 239000012453 solvate Substances 0.000 claims description 23
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
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- JIIXGDGLWIDEHT-CLYVBNDRSA-N 5-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-n-[(2-methoxyphenyl)methyl]-1h-indole-2-carboxamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=CC2=CC(C[C@@H](C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)=CC=C2N1 JIIXGDGLWIDEHT-CLYVBNDRSA-N 0.000 claims description 5
- FDAKLYKEIOPOKK-XBBWARJSSA-N 5-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-n-[2-(3-methoxyphenyl)ethyl]-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(CCNC(=O)C=2NC3=CC=C(C[C@@H](C)NC[C@H](O)C=4C=C(CO)C(O)=CC=4)C=C3C=2)=C1 FDAKLYKEIOPOKK-XBBWARJSSA-N 0.000 claims description 5
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- JHRNSGOBXJUMPH-WRHNGFHOSA-N 5-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-n-[(3-methoxyphenyl)methyl]-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2NC3=CC=C(C[C@@H](C)NC[C@H](O)C=4C=C(CO)C(O)=CC=4)C=C3C=2)=C1 JHRNSGOBXJUMPH-WRHNGFHOSA-N 0.000 claims description 4
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- 208000000059 Dyspnea Diseases 0.000 claims description 2
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- 208000031888 Mycoses Diseases 0.000 claims description 2
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- 208000002200 Respiratory Hypersensitivity Diseases 0.000 claims description 2
- 241000191940 Staphylococcus Species 0.000 claims description 2
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- 201000009323 chronic eosinophilic pneumonia Diseases 0.000 claims description 2
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- 235000015041 whisky Nutrition 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 208000013220 shortness of breath Diseases 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 170
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- 230000000172 allergic effect Effects 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 6
- 208000026935 allergic disease Diseases 0.000 abstract description 2
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- 239000002904 solvent Substances 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
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- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
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- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 1
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- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02292513.5 | 2002-10-11 | ||
| EP20020292513 EP1407769A1 (en) | 2002-10-11 | 2002-10-11 | Indole derivatives as beta-2 agonists |
| EP03290069A EP1440966A1 (en) | 2003-01-10 | 2003-01-10 | Indole derivatives useful for the treatment of diseases |
| EP03290069.8 | 2003-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050047552A true KR20050047552A (ko) | 2005-05-20 |
Family
ID=32095049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057006090A Ceased KR20050047552A (ko) | 2002-10-11 | 2003-10-06 | 베타-2 작용제로서의 인돌 유도체 |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1556034B1 (https=) |
| JP (1) | JP4490911B2 (https=) |
| KR (1) | KR20050047552A (https=) |
| AP (1) | AP2005003283A0 (https=) |
| AR (1) | AR041566A1 (https=) |
| AT (1) | ATE392206T1 (https=) |
| AU (1) | AU2003269316A1 (https=) |
| BR (1) | BR0315234A (https=) |
| CA (1) | CA2499314C (https=) |
| CO (1) | CO5550421A2 (https=) |
| DE (1) | DE60320439T2 (https=) |
| EA (1) | EA200500618A1 (https=) |
| EC (1) | ECSP055780A (https=) |
| ES (1) | ES2302938T3 (https=) |
| IS (1) | IS7751A (https=) |
| MA (1) | MA27452A1 (https=) |
| MX (1) | MXPA05003866A (https=) |
| NO (1) | NO20051406L (https=) |
| OA (1) | OA12938A (https=) |
| PA (1) | PA8586001A1 (https=) |
| PE (1) | PE20040775A1 (https=) |
| PL (1) | PL376396A1 (https=) |
| TW (1) | TW200424171A (https=) |
| UY (1) | UY28013A1 (https=) |
| WO (1) | WO2004032921A1 (https=) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| EP1460064A1 (en) | 2003-03-14 | 2004-09-22 | Pfizer Limited | Indole-2-carboxamide derivatives useful as beta-2 agonists |
| GB0312832D0 (en) * | 2003-06-04 | 2003-07-09 | Pfizer Ltd | 2-amino-pyridine derivatives useful for the treatment of diseases |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| WO2005092841A1 (en) * | 2004-03-23 | 2005-10-06 | Pfizer Limited | Compounds having beta-agonist activity |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| JP2009504624A (ja) | 2005-08-08 | 2009-02-05 | アージェンタ ディスカバリー リミテッド | ビシクロ［２．２．１］ヘプタ−７−イルアミン誘導体およびその使用 |
| WO2007045477A2 (en) | 2005-10-21 | 2007-04-26 | Novartis Ag | Human antibodies against il-13 and therapeutic uses |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| WO2007107828A2 (en) | 2006-03-20 | 2007-09-27 | Pfizer Limited | Amine derivatives |
| PT2322525E (pt) | 2006-04-21 | 2013-12-26 | Novartis Ag | Derivados de purina para utilização como agonistas do recetor de adenosina a2a |
| CA2657639A1 (en) | 2006-07-19 | 2008-01-24 | Astrazeneca Ab | Novel tricyclic spiropiperidine compounds, their synthesis and their uses as modulators of chemokine receptor activity |
| TW200825084A (en) | 2006-11-14 | 2008-06-16 | Astrazeneca Ab | New compounds 521 |
| ATE555111T1 (de) | 2006-12-19 | 2012-05-15 | Astrazeneca Ab | Chinuclidinol-derivate als muscarinrezeptor- antagonisten |
| RS51644B (sr) | 2007-01-10 | 2011-10-31 | Irm Llc. | Jedinjenja i preparati kao inhibitori kanal aktivirajuće proteaze |
| MX2009008493A (es) | 2007-02-09 | 2009-08-20 | Irm Llc | Compuestos y composiciones como inhibidores de la proteasa activadora de canal. |
| CN101687851B (zh) | 2007-05-07 | 2013-02-27 | 诺瓦提斯公司 | 有机化合物 |
| CL2008003651A1 (es) | 2007-12-10 | 2009-06-19 | Novartis Ag | Compuestos derivados de 3,5-diamino-6-cloropirazinamida sustituida; composicion farmaceutica; combinacion farmaceutica; y uso en el tratamiento de una condición inflamatoria o alergica, en particular una enfermedad inflamatoria u obstructiva de las vias respiratorias. |
| AU2009203693B2 (en) | 2008-01-11 | 2012-06-07 | Novartis Ag | Pyrimidines as kinase inhibitors |
| EA017627B1 (ru) | 2008-05-13 | 2013-01-30 | Астразенека Аб | Хинуклидиновые производные в качестве антагонистов мускаринового м3 рецептора |
| MX2010012492A (es) | 2008-05-27 | 2010-12-21 | Astrazeneca Ab | Derivados de fenoxipiridinilamida y su uso en el tratamiento de estados de enfermedad mediados por fosfodiesterasa 4. |
| CA2727196A1 (en) | 2008-06-10 | 2009-12-17 | Novartis Ag | Organic compounds |
| US8236786B2 (en) | 2008-08-07 | 2012-08-07 | Pulmagen Therapeutics (Inflammation) Limited | Respiratory disease treatment |
| WO2010067102A1 (en) | 2008-12-09 | 2010-06-17 | Astrazeneca Ab | Diazaspiro [5.5] undecane derivatives and related compounds as muscarinic-receptor antagonists and beta-adrenoreceptor agonists for the treatment of pulmonary disorders |
| MX2011007036A (es) | 2008-12-30 | 2011-07-20 | Pulmagen Therapeutics Inflammation Ltd | Compuestos de sulfonamida para el tratamiento de trastornos respiratorios. |
| WO2010150014A1 (en) | 2009-06-24 | 2010-12-29 | Pulmagen Therapeutics (Inflammation) Limited | 5r- 5 -deuterated glitazones for respiratory disease treatment |
| JP5801997B2 (ja) | 2009-07-07 | 2015-10-28 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 薬品の組合せを吸入するための投薬ユニット、投薬ユニットのパック、および吸入器 |
| US20110098311A1 (en) | 2009-10-22 | 2011-04-28 | Vertex Pharmaceuticals Incorported | Compositions for treatment of cystic fibrosis and other chronic diseases |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011098746A1 (en) | 2010-02-09 | 2011-08-18 | Pulmagen Therapeutics (Inflammation) Limited | Crystalline acid addition salts of ( 5r) -enanti0mer of pioglitazone |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB201002243D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| GB201016912D0 (en) | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
| MA34969B1 (fr) | 2011-02-25 | 2014-03-01 | Irm Llc | Composes et compositions en tant qu inibiteurs de trk |
| AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
| ME02297B (me) | 2011-06-10 | 2016-02-20 | Chiesi Farm Spa | Jedinjenja koja imaju aktivnost antagonista muskarinskih receptora i agonist beta2 adrenergičnog receptora |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038386A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Heterocyclic compounds for the treatment of cystic fibrosis |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| BR112015012730B1 (pt) | 2012-12-06 | 2022-07-05 | Chiesi Farmaceutici S.P.A. | Composto, composição farmaceutica, dispositivo, uso de um composto e combinação |
| AR093832A1 (es) | 2012-12-06 | 2015-06-24 | Chiesi Farm Spa | COMPUESTOS CON ACTIVIDAD ANTAGONISTA DE LOS RECEPTORES MUSCARINICOS Y ACTIVIDAD AGONISTA DEL RECEPTOR b2 ADRENERGICO |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| AR099336A1 (es) | 2014-02-17 | 2016-07-13 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| BR112016024484A2 (pt) | 2014-04-24 | 2017-08-15 | Novartis Ag | derivados de aminopiridina como inibidores de fosfatidilinositol 3-quinase |
| US9862711B2 (en) | 2014-04-24 | 2018-01-09 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| AU2020290094B2 (en) | 2019-06-10 | 2024-01-18 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF, COPD, and bronchiectasis |
| AU2020338971B2 (en) | 2019-08-28 | 2023-11-23 | Novartis Ag | Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease |
| EP4171525A1 (en) | 2020-06-26 | 2023-05-03 | Mylan Pharma UK Limited | Formulations including 5-[3-(3-hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanamide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9406823A (pt) * | 1993-06-14 | 1996-03-26 | Pfizer | Aminas secundárias e agentes anti-diabéticos e antiobesidade |
| EP0801060A1 (en) * | 1996-04-09 | 1997-10-15 | Pfizer Inc. | Heterocyclic Beta-3 Adrenergenic Agonists |
| EP0822185A1 (en) * | 1996-07-31 | 1998-02-04 | Pfizer Inc. | B-3-adrenergic agonists as antidiabetic and antiobesity agents |
-
2003
- 2003-10-06 ES ES03751095T patent/ES2302938T3/es not_active Expired - Lifetime
- 2003-10-06 EP EP03751095A patent/EP1556034B1/en not_active Expired - Lifetime
- 2003-10-06 CA CA2499314A patent/CA2499314C/en not_active Expired - Fee Related
- 2003-10-06 EA EA200500618A patent/EA200500618A1/ru unknown
- 2003-10-06 AT AT03751095T patent/ATE392206T1/de not_active IP Right Cessation
- 2003-10-06 OA OA1200500099A patent/OA12938A/en unknown
- 2003-10-06 PL PL03376396A patent/PL376396A1/xx unknown
- 2003-10-06 AP AP2005003283A patent/AP2005003283A0/xx unknown
- 2003-10-06 AU AU2003269316A patent/AU2003269316A1/en not_active Abandoned
- 2003-10-06 JP JP2005501006A patent/JP4490911B2/ja not_active Expired - Fee Related
- 2003-10-06 WO PCT/IB2003/004441 patent/WO2004032921A1/en not_active Ceased
- 2003-10-06 DE DE60320439T patent/DE60320439T2/de not_active Expired - Lifetime
- 2003-10-06 BR BR0315234-0A patent/BR0315234A/pt not_active IP Right Cessation
- 2003-10-06 KR KR1020057006090A patent/KR20050047552A/ko not_active Ceased
- 2003-10-06 MX MXPA05003866A patent/MXPA05003866A/es not_active Application Discontinuation
- 2003-10-09 PE PE2003001024A patent/PE20040775A1/es not_active Application Discontinuation
- 2003-10-09 TW TW092128121A patent/TW200424171A/zh unknown
- 2003-10-09 AR ARP030103677A patent/AR041566A1/es unknown
- 2003-10-10 UY UY28013A patent/UY28013A1/es not_active Application Discontinuation
- 2003-10-10 PA PA20038586001A patent/PA8586001A1/es unknown
-
2005
- 2005-03-17 NO NO20051406A patent/NO20051406L/no unknown
- 2005-03-17 IS IS7751A patent/IS7751A/is unknown
- 2005-04-08 CO CO05032119A patent/CO5550421A2/es not_active Application Discontinuation
- 2005-04-11 MA MA28210A patent/MA27452A1/fr unknown
- 2005-05-05 EC EC2005005780A patent/ECSP055780A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PA8586001A1 (es) | 2005-02-04 |
| CA2499314C (en) | 2010-08-24 |
| UY28013A1 (es) | 2004-04-30 |
| EP1556034A1 (en) | 2005-07-27 |
| ATE392206T1 (de) | 2008-05-15 |
| MA27452A1 (fr) | 2005-07-01 |
| AU2003269316A1 (en) | 2004-05-04 |
| PE20040775A1 (es) | 2004-12-10 |
| NO20051406L (no) | 2005-04-22 |
| EA200500618A1 (ru) | 2005-12-29 |
| AR041566A1 (es) | 2005-05-18 |
| DE60320439D1 (de) | 2008-05-29 |
| ECSP055780A (es) | 2005-08-11 |
| WO2004032921A1 (en) | 2004-04-22 |
| JP2006511596A (ja) | 2006-04-06 |
| BR0315234A (pt) | 2005-08-23 |
| EP1556034B1 (en) | 2008-04-16 |
| IS7751A (is) | 2005-03-17 |
| ES2302938T3 (es) | 2008-08-01 |
| JP4490911B2 (ja) | 2010-06-30 |
| DE60320439T2 (de) | 2009-05-20 |
| MXPA05003866A (es) | 2005-06-22 |
| CA2499314A1 (en) | 2004-04-22 |
| PL376396A1 (en) | 2005-12-27 |
| OA12938A (en) | 2006-10-13 |
| AP2005003283A0 (en) | 2005-06-30 |
| TW200424171A (en) | 2004-11-16 |
| CO5550421A2 (es) | 2005-08-31 |
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