JP2016535049A5 - - Google Patents
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- Publication number
- JP2016535049A5 JP2016535049A5 JP2016527342A JP2016527342A JP2016535049A5 JP 2016535049 A5 JP2016535049 A5 JP 2016535049A5 JP 2016527342 A JP2016527342 A JP 2016527342A JP 2016527342 A JP2016527342 A JP 2016527342A JP 2016535049 A5 JP2016535049 A5 JP 2016535049A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- groups
- optionally substituted
- cycloalkyl
- 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.)
- Granted
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- -1 or one NR N ′′ Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 102000014156 AMP-Activated Protein Kinases Human genes 0.000 claims 4
- 108010011376 AMP-Activated Protein Kinases Proteins 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 3
- 125000004976 cyclobutylene group Chemical group 0.000 claims 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims 3
- 125000004979 cyclopentylene group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000016097 disease of metabolism Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 2
- 125000005725 cyclohexenylene group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 229940127003 anti-diabetic drug Drugs 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000005551 pyridylene group Chemical group 0.000 claims 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- 0 *C1COCC1 Chemical compound *C1COCC1 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AHVQYHFYQWKUKB-UHFFFAOYSA-N NC1CCOCC1 Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005482 norpinyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000002873 tetrahydrofuranonyl group Chemical group 0.000 description 1
- 125000002673 tetrahydropyranonyl group Chemical group O1C(C(CCC1)*)=O 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13191195.0 | 2013-10-31 | ||
| EP13191195 | 2013-10-31 | ||
| PCT/EP2014/072959 WO2015063011A1 (en) | 2013-10-31 | 2014-10-27 | Azabenzimidazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016535049A JP2016535049A (ja) | 2016-11-10 |
| JP2016535049A5 true JP2016535049A5 (enExample) | 2017-12-14 |
| JP6474804B2 JP6474804B2 (ja) | 2019-02-27 |
Family
ID=49488531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016527342A Active JP6474804B2 (ja) | 2013-10-31 | 2014-10-27 | アザベンゾイミダゾール誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9187477B2 (enExample) |
| EP (1) | EP3063148B1 (enExample) |
| JP (1) | JP6474804B2 (enExample) |
| WO (1) | WO2015063011A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2015309863B2 (en) | 2014-08-27 | 2019-12-05 | Shionogi & Co., Ltd. | Azaindole derivative having AMPK-activating effect |
| KR20170077131A (ko) | 2014-10-28 | 2017-07-05 | 시오노기세야쿠 가부시키가이샤 | Ampk 활성화 작용을 갖는 복소환 유도체 |
| JPWO2017146186A1 (ja) | 2016-02-26 | 2018-12-20 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有する５−フェニルアザインドール誘導体 |
| CN109476661A (zh) * | 2016-05-20 | 2019-03-15 | 盐野义制药株式会社 | 具有ampk活化作用的5-取代苯并咪唑及5-取代氮杂苯并咪唑衍生物 |
| JP2023526625A (ja) | 2020-05-19 | 2023-06-22 | キャリーオペ，インク． | Ａｍｐｋアクチベーター |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12013501686A1 (en) * | 2011-02-25 | 2017-10-25 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| EP2733141B1 (en) * | 2011-07-15 | 2019-01-09 | Shionogi & Co., Ltd. | Azabenzimidazole derivative having ampk-activating activity |
| WO2014031465A1 (en) * | 2012-08-22 | 2014-02-27 | Merck Sharp & Dohme Corp. | Novel azabenzimidazole tetrahydropyran derivatives |
-
2014
- 2014-10-27 WO PCT/EP2014/072959 patent/WO2015063011A1/en not_active Ceased
- 2014-10-27 JP JP2016527342A patent/JP6474804B2/ja active Active
- 2014-10-27 EP EP14789561.9A patent/EP3063148B1/en active Active
- 2014-10-28 US US14/525,950 patent/US9187477B2/en active Active
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