AU2003269316A1 - Indole derivatives as beta-2 agonists - Google Patents
Indole derivatives as beta-2 agonists Download PDFInfo
- Publication number
- AU2003269316A1 AU2003269316A1 AU2003269316A AU2003269316A AU2003269316A1 AU 2003269316 A1 AU2003269316 A1 AU 2003269316A1 AU 2003269316 A AU2003269316 A AU 2003269316A AU 2003269316 A AU2003269316 A AU 2003269316A AU 2003269316 A1 AU2003269316 A1 AU 2003269316A1
- Authority
- AU
- Australia
- Prior art keywords
- hydroxy
- indole
- ethyl
- carboxamide
- amino
- 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
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- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 49
- 229940124748 beta 2 agonist Drugs 0.000 title description 11
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- 238000000034 method Methods 0.000 claims description 102
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- 239000001257 hydrogen Substances 0.000 claims description 51
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- -1 hydroxy, methyl Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 239000000556 agonist Substances 0.000 claims description 28
- 206010006451 bronchitis Diseases 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
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- WTBGOYCHEVMMHF-CLYVBNDRSA-N n-[(2,6-dimethoxyphenyl)methyl]-5-[(2r)-2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl]amino]propyl]-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(OC)=C1CNC(=O)C1=CC2=CC(C[C@@H](C)NC[C@H](O)C=3C=C(CO)C(O)=CC=3)=CC=C2N1 WTBGOYCHEVMMHF-CLYVBNDRSA-N 0.000 claims 2
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- MZWKEVABVGDUFJ-UHFFFAOYSA-N propyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCCC)=CC2=C1 MZWKEVABVGDUFJ-UHFFFAOYSA-N 0.000 description 1
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- 229950010131 puromycin Drugs 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
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- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 125000005490 tosylate group Chemical class 0.000 description 1
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- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 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
Landscapes
- 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 (5)
| 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 |
| PCT/IB2003/004441 WO2004032921A1 (en) | 2002-10-11 | 2003-10-06 | Indole derivatives as beta-2 agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003269316A1 true AU2003269316A1 (en) | 2004-05-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003269316A Abandoned AU2003269316A1 (en) | 2002-10-11 | 2003-10-06 | Indole derivatives as beta-2 agonists |
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|---|---|
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| JP (1) | JP4490911B2 (enExample) |
| KR (1) | KR20050047552A (enExample) |
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| 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) |
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| 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 |
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| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| RU2442771C2 (ru) | 2005-08-08 | 2012-02-20 | Арджента Дискавери Лтд | Производные бицикло[2,2,1]гепт-7-иламина и их применения |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
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| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| KR20090030347A (ko) | 2006-07-19 | 2009-03-24 | 아스트라제네카 아베 | 신규 트리시클릭 스피로피페리딘 화합물, 이들의 합성 및 이들의 케모킨 수용체 활성의 조절제로서의 용도 |
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| EA200901082A1 (ru) | 2007-02-09 | 2010-02-26 | Айрм Ллк | Соединения и композиции в качестве ингибиторов протеазы, активирующей каналы |
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| ES2654395T3 (es) | 2007-12-10 | 2018-02-13 | Novartis Ag | Análogos de amilorida espirocíclicos como bloqueantes de 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 |
| JP4837800B2 (ja) | 2008-05-13 | 2011-12-14 | アストラゼネカ・アクチエボラーグ | ムスカリンｍ３受容体アンタゴニストとしてのキヌクリジン誘導体 |
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| 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 |
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| EA201692140A1 (ru) | 2014-04-24 | 2017-04-28 | Новартис Аг | Производные аминопиридина в качестве ингибиторов фосфатидилинозитол 3-киназы |
| WO2015162461A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE154935T1 (de) * | 1993-06-14 | 1997-07-15 | Pfizer | Zweite amine als antidiabetische mittel und für die behandlung von fettleibigkeit |
| 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 DE DE60320439T patent/DE60320439T2/de not_active Expired - Lifetime
- 2003-10-06 AP AP2005003283A patent/AP2005003283A0/xx unknown
- 2003-10-06 EA EA200500618A patent/EA200500618A1/ru unknown
- 2003-10-06 ES ES03751095T patent/ES2302938T3/es not_active Expired - Lifetime
- 2003-10-06 PL PL03376396A patent/PL376396A1/xx unknown
- 2003-10-06 EP EP03751095A patent/EP1556034B1/en not_active Expired - Lifetime
- 2003-10-06 JP JP2005501006A patent/JP4490911B2/ja not_active Expired - Fee Related
- 2003-10-06 MX MXPA05003866A patent/MXPA05003866A/es not_active Application Discontinuation
- 2003-10-06 CA CA2499314A patent/CA2499314C/en not_active Expired - Fee Related
- 2003-10-06 AU AU2003269316A patent/AU2003269316A1/en not_active Abandoned
- 2003-10-06 AT AT03751095T patent/ATE392206T1/de not_active IP Right Cessation
- 2003-10-06 BR BR0315234-0A patent/BR0315234A/pt not_active IP Right Cessation
- 2003-10-06 OA OA1200500099A patent/OA12938A/en unknown
- 2003-10-06 WO PCT/IB2003/004441 patent/WO2004032921A1/en not_active Ceased
- 2003-10-06 KR KR1020057006090A patent/KR20050047552A/ko not_active Ceased
- 2003-10-09 AR ARP030103677A patent/AR041566A1/es unknown
- 2003-10-09 TW TW092128121A patent/TW200424171A/zh unknown
- 2003-10-09 PE PE2003001024A patent/PE20040775A1/es not_active Application Discontinuation
- 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 |
|---|---|
| CA2499314A1 (en) | 2004-04-22 |
| AP2005003283A0 (en) | 2005-06-30 |
| ES2302938T3 (es) | 2008-08-01 |
| PL376396A1 (en) | 2005-12-27 |
| UY28013A1 (es) | 2004-04-30 |
| DE60320439D1 (de) | 2008-05-29 |
| KR20050047552A (ko) | 2005-05-20 |
| BR0315234A (pt) | 2005-08-23 |
| EA200500618A1 (ru) | 2005-12-29 |
| TW200424171A (en) | 2004-11-16 |
| JP4490911B2 (ja) | 2010-06-30 |
| EP1556034B1 (en) | 2008-04-16 |
| IS7751A (is) | 2005-03-17 |
| ATE392206T1 (de) | 2008-05-15 |
| AR041566A1 (es) | 2005-05-18 |
| NO20051406L (no) | 2005-04-22 |
| MXPA05003866A (es) | 2005-06-22 |
| PE20040775A1 (es) | 2004-12-10 |
| ECSP055780A (es) | 2005-08-11 |
| EP1556034A1 (en) | 2005-07-27 |
| WO2004032921A1 (en) | 2004-04-22 |
| DE60320439T2 (de) | 2009-05-20 |
| OA12938A (en) | 2006-10-13 |
| PA8586001A1 (es) | 2005-02-04 |
| JP2006511596A (ja) | 2006-04-06 |
| CO5550421A2 (es) | 2005-08-31 |
| MA27452A1 (fr) | 2005-07-01 |
| CA2499314C (en) | 2010-08-24 |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |