JP2015523404A5 - - Google Patents
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- Publication number
- JP2015523404A5 JP2015523404A5 JP2015524747A JP2015524747A JP2015523404A5 JP 2015523404 A5 JP2015523404 A5 JP 2015523404A5 JP 2015524747 A JP2015524747 A JP 2015524747A JP 2015524747 A JP2015524747 A JP 2015524747A JP 2015523404 A5 JP2015523404 A5 JP 2015523404A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- substituted
- cycloalkyl
- independently selected
- 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.)
- Pending
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- -1 pyridinonyl Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 claims description 6
- 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 2
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 0 C*(C)c1ncc(*)cc1 Chemical compound C*(C)c1ncc(*)cc1 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- AWEJUVKHFBPNIS-UHFFFAOYSA-N 5-(1,3-oxazol-5-yl)pyrazine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN=C1C1=CN=CO1 AWEJUVKHFBPNIS-UHFFFAOYSA-N 0.000 description 1
- OBSLLHNATPQFMJ-UHFFFAOYSA-N Cc1c[s]c(C)n1 Chemical compound Cc1c[s]c(C)n1 OBSLLHNATPQFMJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12179028 | 2012-08-02 | ||
| EP12179028.1 | 2012-08-02 | ||
| PCT/EP2013/065862 WO2014019967A1 (en) | 2012-08-02 | 2013-07-29 | N-cyclopropyl-n-piperidinyl-amides, pharmaceutical compositions containing them and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015523404A JP2015523404A (ja) | 2015-08-13 |
| JP2015523404A5 true JP2015523404A5 (enExample) | 2017-08-31 |
Family
ID=48875067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015524747A Pending JP2015523404A (ja) | 2012-08-02 | 2013-07-29 | Ｎ−シクロプロピル−ｎ−ピペリジニル−アミド、これらを含有する医薬組成物およびその使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US20140045823A1 (enExample) |
| EP (1) | EP2880027B1 (enExample) |
| JP (1) | JP2015523404A (enExample) |
| WO (1) | WO2014019967A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA113777C2 (xx) * | 2012-09-25 | 2017-03-10 | Гербіцидно й фунгіцидно діючі 5-оксизаміщені 3-фенілізоксазолін-5-карбоксаміди і 5-оксизаміщені 3-фенілізоксазолін-5-тіоаміди |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8039458B2 (en) | 2005-11-17 | 2011-10-18 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| NZ571869A (en) * | 2006-04-06 | 2011-11-25 | Prosidion Ltd | Heterocyclic GPCR agonists |
| ATE476418T1 (de) * | 2006-06-08 | 2010-08-15 | Amgen Inc | Benzamidderivate und assoziierte verwendungen |
| WO2009106561A1 (en) * | 2008-02-27 | 2009-09-03 | Biovitrum Ab (Publ) | Pyrazine compounds for treating gpr119 related disorders |
| WO2009117421A2 (en) * | 2008-03-17 | 2009-09-24 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| CN102686579A (zh) * | 2009-10-09 | 2012-09-19 | Irm责任有限公司 | 作为gpr119活性调节剂的化合物和组合物 |
| JP5935154B2 (ja) * | 2011-03-14 | 2016-06-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｇｐｒ１１９モジュレーターとしてのｎ−シクロプロピル−ｎ−ピペリジニルベンズアミド |
| EP2718288B1 (en) * | 2011-06-09 | 2015-03-11 | Boehringer Ingelheim International GmbH | Substituted piperidines as gpr119 modulators for the treatment of metabolic disorders |
| FR2992637B1 (fr) * | 2012-06-29 | 2014-07-04 | IFP Energies Nouvelles | Photocatalyseur composite a base de sulfures metalliques pour la production d'hydrogene |
-
2013
- 2013-07-29 WO PCT/EP2013/065862 patent/WO2014019967A1/en not_active Ceased
- 2013-07-29 JP JP2015524747A patent/JP2015523404A/ja active Pending
- 2013-07-29 EP EP13741779.6A patent/EP2880027B1/en active Active
- 2013-07-31 US US13/955,170 patent/US20140045823A1/en not_active Abandoned
-
2016
- 2016-02-16 US US15/044,719 patent/US9926308B2/en active Active
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