AU2010319927B2 - Alkynyl derivatives useful as DPP-1 inhibitors - Google Patents
Alkynyl derivatives useful as DPP-1 inhibitors Download PDFInfo
- Publication number
- AU2010319927B2 AU2010319927B2 AU2010319927A AU2010319927A AU2010319927B2 AU 2010319927 B2 AU2010319927 B2 AU 2010319927B2 AU 2010319927 A AU2010319927 A AU 2010319927A AU 2010319927 A AU2010319927 A AU 2010319927A AU 2010319927 B2 AU2010319927 B2 AU 2010319927B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- group
- methyl
- oxy
- alkyl
- 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
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- 125000000304 alkynyl group Chemical group 0.000 title claims abstract description 9
- 239000003112 inhibitor Substances 0.000 title description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
- 208000035475 disorder Diseases 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- -1 piperidinyl-oxy- Chemical class 0.000 claims description 205
- 150000001875 compounds Chemical class 0.000 claims description 171
- 239000000203 mixture Substances 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 22
- 208000006673 asthma Diseases 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000003937 drug carrier Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
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- 201000010099 disease Diseases 0.000 claims description 18
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- 230000008569 process Effects 0.000 claims description 18
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- 125000001624 naphthyl group Chemical group 0.000 claims description 9
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- 230000001684 chronic effect Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
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- 238000002156 mixing Methods 0.000 claims description 8
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
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- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
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- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- 208000019693 Lung disease Diseases 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
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- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
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Citations (2)
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| US4847241A (en) * | 1985-08-14 | 1989-07-11 | G. D. Searle & Co. | Fluorenyl substituted tyrosyl dipeptide amides which are useful in treating pain |
| US20070155803A1 (en) * | 2003-05-30 | 2007-07-05 | Prozymex A/S | Protease inhibitors |
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| US5424334A (en) | 1991-12-19 | 1995-06-13 | G. D. Searle & Co. | Peptide mimetic compounds useful as platelet aggregation inhibitors |
| DE4321502A1 (de) | 1993-06-29 | 1995-01-12 | Bayer Ag | Alkinol-substituierte Peptide, Verfahren zu ihrer Herstellung und ihre Verwendung als antiretrovirale Mittel |
| AU6490396A (en) | 1995-07-14 | 1997-02-18 | Smithkline Beecham Corporation | Substituted-pent-4-ynoic acids |
| NZ318926A (en) | 1995-08-30 | 1999-04-29 | Searle & Co | Alpha v beta 3 integrin (vitronectin) inhibitors or anatagonists derived from benzoic acid for treating diseases of cell adhesion |
| JP2002145897A (ja) | 2000-11-10 | 2002-05-22 | Kyorin Pharmaceut Co Ltd | アミノ酸誘導体及びその製造法 |
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| DE60226906D1 (de) * | 2002-07-31 | 2008-07-10 | Ranbaxy Lab Ltd | 3,6-disubstituierte azabicyclo ä3.1.0ühexanderivate, die sich als muscarinrezeptorantagonisten eignen |
| US20040186151A1 (en) * | 2003-02-12 | 2004-09-23 | Mjalli Adnan M.M. | Substituted azole derivatives as therapeutic agents |
| AU2004210711B2 (en) * | 2003-02-12 | 2010-07-08 | Transtech Pharma, Inc. | Substituted azole derivatives as therapeutic agents |
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| DE102005009784B4 (de) * | 2005-03-03 | 2009-06-18 | Technische Universität Darmstadt | Peptid-Mimetika, Verfahren zur deren Herstellung, diese enthaltende pharmazeutische Zusammensetzung und deren Verwendung als Inhibitoren von Proteasomen und zur Induktion von Apoptose |
| KR20080004550A (ko) * | 2005-03-30 | 2008-01-09 | 콘포마 세러퓨틱스 코포레이션 | Hsp90-억제제로서 알키닐 피롤로피리미딘 및 관련유사체 |
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| BRPI0820665A2 (pt) | 2007-12-12 | 2018-05-29 | Astrazeneca Ab | compostos de peptidil nitrilas, processos para fabricação dos mesmos, composição farmacêutica, combinação e uso de ditos compostos |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4847241A (en) * | 1985-08-14 | 1989-07-11 | G. D. Searle & Co. | Fluorenyl substituted tyrosyl dipeptide amides which are useful in treating pain |
| US20070155803A1 (en) * | 2003-05-30 | 2007-07-05 | Prozymex A/S | Protease inhibitors |
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| WO2011059731A1 (en) | 2011-05-19 |
| CN102596321B (zh) | 2014-11-19 |
| ES2513291T3 (es) | 2014-10-24 |
| AU2010319927A1 (en) | 2012-05-17 |
| JP2013509423A (ja) | 2013-03-14 |
| EP2493571A1 (en) | 2012-09-05 |
| EP2493571B1 (en) | 2014-07-23 |
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