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 |
|---|---|---|---|
| EP20020292513 EP1407769A1 (en) | 2002-10-11 | 2002-10-11 | Indole derivatives as beta-2 agonists |
| EP02292513.5 | 2002-10-11 | ||
| EP03290069.8 | 2003-01-10 | ||
| EP03290069A EP1440966A1 (en) | 2003-01-10 | 2003-01-10 | Indole derivatives useful for the treatment of diseases |
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 |
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| JP (1) | JP4490911B2 (enExample) |
| KR (1) | KR20050047552A (enExample) |
| AP (1) | AP2005003283A0 (enExample) |
| AR (1) | AR041566A1 (enExample) |
| AT (1) | ATE392206T1 (enExample) |
| AU (1) | AU2003269316A1 (enExample) |
| BR (1) | BR0315234A (enExample) |
| CA (1) | CA2499314C (enExample) |
| CO (1) | CO5550421A2 (enExample) |
| DE (1) | DE60320439T2 (enExample) |
| EA (1) | EA200500618A1 (enExample) |
| EC (1) | ECSP055780A (enExample) |
| ES (1) | ES2302938T3 (enExample) |
| IS (1) | IS7751A (enExample) |
| MA (1) | MA27452A1 (enExample) |
| MX (1) | MXPA05003866A (enExample) |
| NO (1) | NO20051406L (enExample) |
| OA (1) | OA12938A (enExample) |
| PA (1) | PA8586001A1 (enExample) |
| PE (1) | PE20040775A1 (enExample) |
| PL (1) | PL376396A1 (enExample) |
| TW (1) | TW200424171A (enExample) |
| UY (1) | UY28013A1 (enExample) |
| WO (1) | WO2004032921A1 (enExample) |
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 |
| AR049384A1 (es) | 2004-05-24 | 2006-07-26 | Glaxo Group Ltd | Derivados de purina |
| 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 |
| EP1924553A1 (en) | 2005-08-08 | 2008-05-28 | Argenta Discovery Limited | Bicyclo[2.2.]hept-7-ylamine derivatives and their uses |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| EP1957530A2 (en) | 2005-10-21 | 2008-08-20 | Novartis AG | Human antibodies against il13 and therapeutic uses |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| EA016203B1 (ru) | 2006-03-20 | 2012-03-30 | Пфайзер Лимитед | Производные амина |
| SI2013211T1 (sl) | 2006-04-21 | 2012-07-31 | Novartis Ag | Purinski derivati za uporabo kot agonisti receptorja adenozina A A |
| AU2007275931B2 (en) | 2006-07-19 | 2011-06-16 | 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 |
| BRPI0721039A2 (pt) | 2006-12-19 | 2014-07-29 | Astrazeneca Ab | " derivados de quinuclidinol como antagonistas de receptores muscarínicos ". |
| PL2104535T3 (pl) | 2007-01-10 | 2011-05-31 | Irm Llc | Związki i kompozycje jako inhibitory proteazy aktywujące kanały |
| JP2010518097A (ja) | 2007-02-09 | 2010-05-27 | アイアールエム・リミテッド・ライアビリティ・カンパニー | チャネル活性化プロテアーゼ阻害剤としての化合物および組成物 |
| AU2008248598B2 (en) | 2007-05-07 | 2011-11-17 | Novartis Ag | Organic compounds |
| PL2444120T3 (pl) | 2007-12-10 | 2018-02-28 | Novartis Ag | Spirocyklicze analogi amiloridu jako blokery ENac |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| EP2300464A1 (en) | 2008-05-13 | 2011-03-30 | AstraZeneca AB | Quinuclidine derivatives as muscarinic m3 receptor antagonists |
| KR101605576B1 (ko) | 2008-05-27 | 2016-03-22 | 아스트라제네카 아베 | 페녹시피리디닐아미드 유도체 및 ｐｄｅ４ 매개 질환 상태의 치료에서의 그의 용도 |
| KR20110040818A (ko) | 2008-06-10 | 2011-04-20 | 노파르티스 아게 | 상피 나트륨 채널 차단제로서의 피라진 유도체 |
| 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 |
| JP5555255B2 (ja) | 2008-12-30 | 2014-07-23 | プルマゲン セラピューティクス（インフラメーション）リミテッド | 呼吸器疾患の治療のためのスルホンアミド化合物 |
| 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 |
| EP2490687A1 (en) | 2009-10-22 | 2012-08-29 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine 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 |
| GEP20156285B (en) | 2011-02-25 | 2015-05-11 | Aierem Elelsi | Compounds and compositions as trk inhibitors |
| AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
| HRP20151317T1 (hr) | 2011-06-10 | 2016-01-01 | Chiesi Farmaceutici S.P.A. | Spojevi koji pokazuju aktivnost prema antagonistima muskarinskog receptora i beta2 adrenergiäśnog receptora |
| UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| ES2558457T3 (es) | 2011-09-16 | 2016-02-04 | Novartis Ag | Compuestos heterocíclicos para el tratamiento de fibrosis quística |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| MX369311B (es) | 2012-12-06 | 2019-11-05 | Chiesi Farm Spa | Compuestos con actividad antagonista de los receptores muscarinicos y actividad agonista del receptor beta2 adrenergico. |
| RU2661877C2 (ru) | 2012-12-06 | 2018-07-20 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Соединения, обладающие активностью антагонистов мускариновых рецепторов и агонистов бета-2-адренергических рецепторов |
| 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 |
| US10112926B2 (en) | 2014-04-24 | 2018-10-30 | Novartis Ag | Amino pyridine derivatives as phosphatidylinositol 3-kinase inhibitors |
| EA033571B1 (ru) | 2014-04-24 | 2019-11-06 | Novartis Ag | Производные пиразина в качестве ингибиторов фосфатидилинозитол 3-киназы |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| MX2021015133A (es) | 2019-06-10 | 2022-01-24 | Novartis Ag | Derivado de piridina y pirazina para el tratamiento de la fibrosis quistica, enfermedad pulmonar obstructiva cronica y bronquiectasia. |
| PE20220346A1 (es) | 2019-08-28 | 2022-03-14 | Novartis Ag | Derivados de 1,3-fenil heteroarilo sustituidos y su uso en el tratamiento de enfermedades |
| US20230293430A1 (en) | 2020-06-26 | 2023-09-21 | 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 |
|---|---|---|---|---|
| CN1129443A (zh) * | 1993-06-14 | 1996-08-21 | 美国辉瑞有限公司 | 仲胺用作治糖尿病和治肥胖病药物 |
| EP0801060A1 (en) * | 1996-04-09 | 1997-10-15 | Pfizer Inc. | Heterocyclic Beta-3 Adrenergenic Agonists |
| US5859044A (en) * | 1996-07-31 | 1999-01-12 | Pfizer Inc. | β-adrenergic agonists |
-
2003
- 2003-10-06 BR BR0315234-0A patent/BR0315234A/pt not_active IP Right Cessation
- 2003-10-06 CA CA2499314A patent/CA2499314C/en not_active Expired - Fee Related
- 2003-10-06 PL PL03376396A patent/PL376396A1/xx unknown
- 2003-10-06 KR KR1020057006090A patent/KR20050047552A/ko not_active Ceased
- 2003-10-06 AT AT03751095T patent/ATE392206T1/de not_active IP Right Cessation
- 2003-10-06 ES ES03751095T patent/ES2302938T3/es not_active Expired - Lifetime
- 2003-10-06 DE DE60320439T patent/DE60320439T2/de not_active Expired - Lifetime
- 2003-10-06 AP AP2005003283A patent/AP2005003283A0/xx unknown
- 2003-10-06 MX MXPA05003866A patent/MXPA05003866A/es not_active Application Discontinuation
- 2003-10-06 AU AU2003269316A patent/AU2003269316A1/en not_active Abandoned
- 2003-10-06 WO PCT/IB2003/004441 patent/WO2004032921A1/en not_active Ceased
- 2003-10-06 JP JP2005501006A patent/JP4490911B2/ja not_active Expired - Fee Related
- 2003-10-06 EA EA200500618A patent/EA200500618A1/ru unknown
- 2003-10-06 OA OA1200500099A patent/OA12938A/en unknown
- 2003-10-06 EP EP03751095A patent/EP1556034B1/en not_active Expired - Lifetime
- 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 PA PA20038586001A patent/PA8586001A1/es unknown
- 2003-10-10 UY UY28013A patent/UY28013A1/es not_active Application Discontinuation
-
2005
- 2005-03-17 IS IS7751A patent/IS7751A/is unknown
- 2005-03-17 NO NO20051406A patent/NO20051406L/no 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 |
|---|---|
| AR041566A1 (es) | 2005-05-18 |
| PE20040775A1 (es) | 2004-12-10 |
| UY28013A1 (es) | 2004-04-30 |
| CA2499314C (en) | 2010-08-24 |
| EP1556034B1 (en) | 2008-04-16 |
| WO2004032921A1 (en) | 2004-04-22 |
| NO20051406L (no) | 2005-04-22 |
| ECSP055780A (es) | 2005-08-11 |
| CA2499314A1 (en) | 2004-04-22 |
| EA200500618A1 (ru) | 2005-12-29 |
| DE60320439D1 (de) | 2008-05-29 |
| OA12938A (en) | 2006-10-13 |
| AU2003269316A1 (en) | 2004-05-04 |
| AP2005003283A0 (en) | 2005-06-30 |
| PA8586001A1 (es) | 2005-02-04 |
| MXPA05003866A (es) | 2005-06-22 |
| JP2006511596A (ja) | 2006-04-06 |
| IS7751A (is) | 2005-03-17 |
| DE60320439T2 (de) | 2009-05-20 |
| ES2302938T3 (es) | 2008-08-01 |
| BR0315234A (pt) | 2005-08-23 |
| JP4490911B2 (ja) | 2010-06-30 |
| EP1556034A1 (en) | 2005-07-27 |
| CO5550421A2 (es) | 2005-08-31 |
| PL376396A1 (en) | 2005-12-27 |
| MA27452A1 (fr) | 2005-07-01 |
| TW200424171A (en) | 2004-11-16 |
| ATE392206T1 (de) | 2008-05-15 |
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