AU2004246983B2 - New azetidine compounds - Google Patents
New azetidine compounds Download PDFInfo
- Publication number
- AU2004246983B2 AU2004246983B2 AU2004246983A AU2004246983A AU2004246983B2 AU 2004246983 B2 AU2004246983 B2 AU 2004246983B2 AU 2004246983 A AU2004246983 A AU 2004246983A AU 2004246983 A AU2004246983 A AU 2004246983A AU 2004246983 B2 AU2004246983 B2 AU 2004246983B2
- Authority
- AU
- Australia
- Prior art keywords
- fluorophenyl
- butyl
- mixture
- compound
- mmol
- 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
- 150000001539 azetidines Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 154
- 150000001875 compounds Chemical class 0.000 claims description 150
- 238000000034 method Methods 0.000 claims description 86
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 16
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- AYHRZURSFYCWMW-LJQANCHMSA-N 3,5-dibromo-n-[(2s)-2-(4-fluorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl]-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(Br)C=C(Br)C=1)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCC(O)CC1 AYHRZURSFYCWMW-LJQANCHMSA-N 0.000 claims 1
- YJRDBGBGTCUUIM-LJQANCHMSA-N 3,5-dichloro-n-[(2s)-2-(4-fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl]-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(Cl)C=C(Cl)C=1)C=1C=CC(F)=CC=1)CN(C1)CC1N1CCOCC1 YJRDBGBGTCUUIM-LJQANCHMSA-N 0.000 claims 1
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- RLGBPDWDLDPHML-UHFFFAOYSA-N n-[2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-n-methyl-3,5-bis(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(=O)N(C)CC(C=1C=CC(F)=CC=1)CCN(C1)CC1N1CCSCC1 RLGBPDWDLDPHML-UHFFFAOYSA-N 0.000 claims 1
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- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- YUPIMTGWBOXLJT-GOSISDBHSA-N tert-butyl n-[(2s)-2-(3,4-dichlorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-n-methylcarbamate Chemical compound C([C@H](CN(C)C(=O)OC(C)(C)C)C=1C=C(Cl)C(Cl)=CC=1)CN(C1)CC1N1CCSCC1 YUPIMTGWBOXLJT-GOSISDBHSA-N 0.000 description 1
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- IKIZSWQLRLZGQO-UHFFFAOYSA-N tert-butyl n-[2-(4-fluorophenyl)pent-4-enyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC(CC=C)C1=CC=C(F)C=C1 IKIZSWQLRLZGQO-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0301744A SE0301744D0 (sv) | 2003-06-13 | 2003-06-13 | New compounds |
| SE0301744-9 | 2003-06-13 | ||
| SE0303493-1 | 2003-12-19 | ||
| SE0303493A SE0303493D0 (sv) | 2003-12-19 | 2003-12-19 | New compounds |
| PCT/SE2004/000901 WO2004110344A2 (en) | 2003-06-13 | 2004-06-09 | New azetidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004246983A1 AU2004246983A1 (en) | 2004-12-23 |
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| SE0403005D0 (sv) * | 2004-12-09 | 2004-12-09 | Astrazeneca Ab | New use |
| KR20080036957A (ko) * | 2005-06-23 | 2008-04-29 | 아스트라제네카 아베 | 위장 질환 치료용 뉴로키닌 수용체 길항제로서의 신규한아제티딘 유도체 |
| CN101208327A (zh) * | 2005-06-23 | 2008-06-25 | 阿斯利康(瑞典)有限公司 | 作为神经激肽受体拮抗剂用于治疗胃肠疾病的新氮杂环丁烷衍生物 |
| AR057828A1 (es) | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
| AR056087A1 (es) * | 2005-09-29 | 2007-09-19 | Astrazeneca Ab | Derivados de azetidina como antagonistas de receptores de neuroquina nk |
| WO2007043938A1 (en) * | 2005-10-07 | 2007-04-19 | Astrazeneca Ab | NOVEL CRYSTALLINE FORM OF 3,5-DIBROMO-N- [ (2S) -2- (-4- FLUOROPHENYL) -4- (3-MORPHOLIN-4-YLAZTIDIN-l-YL) BUTYL] -N METHYLBENZAMIDE, MODIFICATION B |
| WO2007043939A1 (en) * | 2005-10-07 | 2007-04-19 | Astrazeneca Ab | Novel crystalline form of 3,5-dibromo-n- [(2s)-2-(-4-fluorophenyl)-4-(3-morpholin-4-ylazetidin-1-yl)butyl] -n-methylbenzamide, modification a |
| WO2007136326A2 (en) * | 2006-05-18 | 2007-11-29 | Astrazeneca Ab | ) t e text as een esta s e y t s ut o ty to rea as o ows: 1- [ (4- [benzoyl (methyl) amino] -3- (phenyl) butyl] azetidine derivatives for the treatment of gastrointestinal disorders 3 |
| WO2007136325A1 (en) * | 2006-05-18 | 2007-11-29 | Astrazeneca Ab | 1- [ (4- [benzoyl (methyl) amino] -3- (phenyl) butyl] azetidine derivatives for the treatment of gastrointestinal disorders 2 |
| US8106208B2 (en) * | 2006-05-18 | 2012-01-31 | Albireo Ab | Benzamide compounds that act as NK receptor antagonists |
| CL2007002097A1 (es) * | 2006-07-20 | 2008-01-18 | Smithkline Beecham Corp | Compuestos derivados de pirrolidina o morfolina antagonistas de urotensina ii; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar insuficiencia cardiaca congestiva, insuficiencia cardiaca isquemica, angina, isquemia del miocardio, vejiga hiperactiva, asma y/o copd, entre otras. |
| JP2010500401A (ja) * | 2006-08-15 | 2010-01-07 | アクテリオン ファーマシューティカルズ リミテッド | アゼチジン化合物 |
| WO2008076041A1 (en) * | 2006-12-19 | 2008-06-26 | Albireo Ab | Azetidinazabicyclo [3.2.1] octan derivatives that are neurokinin (nk) receptor antagonists and their use. |
| WO2008076042A1 (en) * | 2006-12-19 | 2008-06-26 | Astrazeneca Ab | Azetidinpiperazine derivatives that are neurokinin (nk) receptor antagonists and their use. |
| PL2125711T3 (pl) * | 2007-03-08 | 2014-05-30 | Albireo Ab | Pochodne kwasy 3-fenylopropionowego oraz ich zastosowanie w leczeniu nieswoistego zapalenia jelit |
| WO2008118091A1 (en) * | 2007-03-28 | 2008-10-02 | Albireo Ab | A fumarate salt of 3-bromo-n-{ (2s) -2- (4 -fluorophenyl) -4- [3- (4-acetylpiperazin-l-yl) azetidin-1-yl] butyl} -n-methyl-5- (trifluoromethyl)benzamide for the treatment of gastrointestinal disorders |
| WO2008118092A1 (en) * | 2007-03-28 | 2008-10-02 | Albireo Ab | Maleate salt of 3-bromo-n-{ (2s) -2- (4-f luorophenyl) -4- [3- (4-acetylpiperazin-1-yl) azetidin-1-yl] butyl} -methyl-5- (trifluoromethyl)benzamide for the treatment of gastrointestinal disorders |
| DK2310401T3 (da) | 2008-07-22 | 2016-02-29 | Univ Columbia | Universale methyleringsprofileringsfremgangsmåder |
| US10337049B2 (en) | 2013-06-17 | 2019-07-02 | The Trustees Of Columbia University In The City Of New York | Universal methylation profiling methods |
| CN113603670B (zh) * | 2021-07-23 | 2022-07-29 | 阜阳欣奕华制药科技有限公司 | 一种制备1-(7-溴苯并并[d][1,3]二氧杂环戊烯-4-基)乙-1-酮的方法 |
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| IE903957A1 (en) * | 1989-11-06 | 1991-05-08 | Sanofi Sa | Aromatic amine compounds, their method of preparation and¹pharmaceutical compositions in which they are present |
| GB9310066D0 (en) | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Alkyl substituted heterocycles |
| GB9310713D0 (en) | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Aryl substituted heterocycles |
| GB9317104D0 (en) | 1993-08-17 | 1993-09-29 | Zeneca Ltd | Therapeutic heterocycles |
| GB9322643D0 (en) | 1993-11-03 | 1993-12-22 | Zeneca Ltd | Lactam derivatives |
| GB9325284D0 (en) | 1993-12-10 | 1994-02-16 | Rhone Poulenc Agriculture | Herbicidal compositions |
| TW432061B (en) | 1994-08-09 | 2001-05-01 | Pfizer Res & Dev | Lactams |
| US5607936A (en) | 1994-09-30 | 1997-03-04 | Merck & Co., Inc. | Substituted aryl piperazines as neurokinin antagonists |
| GB9502644D0 (en) | 1995-02-10 | 1995-03-29 | Zeneca Ltd | Heterocyclic derivatives |
| GB9600235D0 (en) | 1996-01-05 | 1996-03-06 | Pfizer Ltd | Therapeutic agents |
| GB9601202D0 (en) * | 1996-01-22 | 1996-03-20 | Pfizer Ltd | Piperidones |
| GB9601680D0 (en) | 1996-01-27 | 1996-03-27 | Pfizer Ltd | Therapeutic agents |
| GB9601697D0 (en) | 1996-01-27 | 1996-03-27 | Pfizer Ltd | Therapeutic agents |
| GB9714129D0 (en) | 1997-07-04 | 1997-09-10 | Pfizer Ltd | Azetidines |
| US6013652A (en) * | 1997-12-04 | 2000-01-11 | Merck & Co., Inc. | Spiro-substituted azacycles as neurokinin antagonists |
| GB9812037D0 (en) | 1998-06-04 | 1998-07-29 | Pfizer Ltd | Piperidones |
| BR9912013A (pt) | 1998-07-10 | 2001-04-10 | Astrazeneca Ab | Composto, composição farmacêutica, método de tratar uma condição de doença, e, processo para preparar um composto |
| GB9922519D0 (en) * | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
| GB9922521D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
| GB9924141D0 (en) | 1998-10-30 | 1999-12-15 | Zeneca Ltd | Treatment of gastric asthma |
| GB9826941D0 (en) * | 1998-12-09 | 1999-02-03 | Zeneca Pharmaceuticals | Compounds |
| SE0004827D0 (sv) | 2000-12-22 | 2000-12-22 | Astrazeneca Ab | Therapeutic compounds |
| SE0103795D0 (sv) | 2001-11-02 | 2001-11-02 | Astrazeneca Ab | Compounds and method for the treatment of överactive bladder |
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- 2004-06-09 AU AU2004246983A patent/AU2004246983B2/en not_active Ceased
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- 2004-06-09 JP JP2006517025A patent/JP4982886B2/ja not_active Expired - Fee Related
- 2004-06-09 WO PCT/SE2004/000901 patent/WO2004110344A2/en not_active Ceased
- 2004-06-09 KR KR1020057023907A patent/KR20060021373A/ko not_active Withdrawn
- 2004-06-09 DE DE602004022546T patent/DE602004022546D1/de not_active Expired - Lifetime
- 2004-06-09 DK DK04736475T patent/DK1636221T3/da active
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- 2004-06-09 PT PT04736475T patent/PT1636221E/pt unknown
- 2004-06-09 US US10/560,319 patent/US7402581B2/en not_active Expired - Fee Related
- 2004-06-09 EP EP04736475A patent/EP1636221B1/en not_active Expired - Lifetime
- 2004-06-09 RU RU2005136535/04A patent/RU2356888C2/ru not_active IP Right Cessation
- 2004-06-09 BR BRPI0411285-7A patent/BRPI0411285A/pt active Search and Examination
- 2004-06-09 AT AT04736475T patent/ATE439358T1/de not_active IP Right Cessation
- 2004-06-09 PL PL04736475T patent/PL1636221T3/pl unknown
- 2004-06-10 AR ARP040102012A patent/AR044662A1/es unknown
- 2004-06-11 MY MYPI20042250A patent/MY146599A/en unknown
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- 2005-12-07 CO CO05124364A patent/CO5640122A2/es not_active Application Discontinuation
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2006
- 2006-01-11 IS IS8228A patent/IS8228A/is unknown
- 2006-01-13 NO NO20060206A patent/NO332109B1/no not_active IP Right Cessation
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| Citations listed in International Search Report * |
Also Published As
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| EP1636221A2 (en) | 2006-03-22 |
| PT1636221E (pt) | 2009-11-05 |
| MY146599A (en) | 2012-08-30 |
| TW200508221A (en) | 2005-03-01 |
| ES2330522T3 (es) | 2009-12-11 |
| HK1088004A1 (en) | 2006-10-27 |
| CO5640122A2 (es) | 2006-05-31 |
| MXPA05013276A (es) | 2006-03-09 |
| NO20060206L (no) | 2006-03-13 |
| AR044662A1 (es) | 2005-09-21 |
| RU2356888C2 (ru) | 2009-05-27 |
| JP2006527267A (ja) | 2006-11-30 |
| DK1636221T3 (da) | 2009-10-12 |
| RU2005136535A (ru) | 2006-07-27 |
| ATE439358T1 (de) | 2009-08-15 |
| DE602004022546D1 (de) | 2009-09-24 |
| IL171894A (en) | 2012-05-31 |
| JP4982886B2 (ja) | 2012-07-25 |
| WO2004110344A3 (en) | 2005-02-17 |
| KR20060021373A (ko) | 2006-03-07 |
| US7402581B2 (en) | 2008-07-22 |
| BRPI0411285A (pt) | 2006-08-01 |
| AU2004246983A1 (en) | 2004-12-23 |
| CA2529126A1 (en) | 2004-12-23 |
| EP1636221B1 (en) | 2009-08-12 |
| CA2529126C (en) | 2011-11-08 |
| IL171894A0 (en) | 2006-04-10 |
| PL1636221T3 (pl) | 2010-01-29 |
| IS8228A (is) | 2006-01-11 |
| WO2004110344A2 (en) | 2004-12-23 |
| US20060172988A1 (en) | 2006-08-03 |
| NO332109B1 (no) | 2012-06-25 |
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