JP2013509425A5 - - Google Patents
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- Publication number
- JP2013509425A5 JP2013509425A5 JP2012537060A JP2012537060A JP2013509425A5 JP 2013509425 A5 JP2013509425 A5 JP 2013509425A5 JP 2012537060 A JP2012537060 A JP 2012537060A JP 2012537060 A JP2012537060 A JP 2012537060A JP 2013509425 A5 JP2013509425 A5 JP 2013509425A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- aryl
- halo
- 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
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- -1 R 2a is Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000003106 haloaryl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Chemical group 0.000 claims 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 201000004792 malaria Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 239000012425 OXONE® Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 claims 1
- ULZCOWMSBOJCLT-UHFFFAOYSA-N CN(CC1)CCS1(=O)=O Chemical compound CN(CC1)CCS1(=O)=O ULZCOWMSBOJCLT-UHFFFAOYSA-N 0.000 description 1
- DYRLRFXNPWUDTO-UHFFFAOYSA-N NC1=Nc2ccccc2C1(c1ccccc1)O Chemical compound NC1=Nc2ccccc2C1(c1ccccc1)O DYRLRFXNPWUDTO-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Nc1ccccc1 Chemical compound Nc1ccccc1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25687909P | 2009-10-30 | 2009-10-30 | |
| US61/256,879 | 2009-10-30 | ||
| PCT/US2010/054473 WO2011053697A1 (en) | 2009-10-30 | 2010-10-28 | 2-aminoindole compounds and methods for the treatment of malaria |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013509425A JP2013509425A (ja) | 2013-03-14 |
| JP2013509425A5 true JP2013509425A5 (https=) | 2013-12-12 |
| JP5907876B2 JP5907876B2 (ja) | 2016-04-26 |
Family
ID=43922536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537060A Active JP5907876B2 (ja) | 2009-10-30 | 2010-10-28 | マラリアの治療のための２−アミノインドール化合物および方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8980926B2 (https=) |
| EP (1) | EP2493305B1 (https=) |
| JP (1) | JP5907876B2 (https=) |
| CA (1) | CA2779452C (https=) |
| ES (1) | ES2539365T3 (https=) |
| MX (1) | MX2012004914A (https=) |
| PL (1) | PL2493305T3 (https=) |
| WO (1) | WO2011053697A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2514007C1 (ru) * | 2012-10-04 | 2014-04-27 | Государственное научное учреждение Северо-Кавказский зональный научно-исследовательский ветеринарный институт (ГНУ СКЗНИВИ) Российской академии сельскохозяйственных наук | Протистоцидная активность 2-(4,5-дихлоримидазолил-1)-5 нитропиридина |
| WO2016201025A1 (en) * | 2015-06-09 | 2016-12-15 | Northwestern University | Photocrosslinking reagents and methods of use thereof |
| CN108314613B (zh) * | 2018-04-16 | 2021-06-18 | 深圳市祥根生物医药有限公司 | 一种达格列净异构体杂质ⅰ的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576001A (en) * | 1967-12-28 | 1971-04-20 | American Home Prod | 2-amino-3-aryl-3h-indol-3-ols and their method of preparation |
| US3577435A (en) | 1968-08-14 | 1971-05-04 | American Home Prod | Process for the preparation of 3-aryl-2-imino-3-indolinols and related compounds |
| US3586693A (en) | 1969-07-07 | 1971-06-22 | American Home Prod | Imidazo(1,2-a)indolin-9-ols |
| US3801593A (en) | 1970-01-13 | 1974-04-02 | American Home Prod | 1-acetyl-2-acetylimino-5-chloro-3-phenyl-3-indolinol,acetate |
| US3686210A (en) | 1970-01-13 | 1972-08-22 | American Home Prod | 2-acylamido-3-aryl-3h-indol-3-ol esters and related compounds |
| US3714188A (en) * | 1970-12-09 | 1973-01-30 | American Home Prod | Process for the preparation of 3-aryl-2-imino-3-indolinols and 2-amino-3-aryl-3h-indol-3-ols and related compounds |
| GB1427066A (en) * | 1973-04-12 | 1976-03-03 | Wyeth John & Brother Ltd | Fused ring indole derivatives |
| JPS5579366A (en) | 1978-12-08 | 1980-06-14 | Asahi Chem Ind Co Ltd | Preparation of 2-aminoindolenine |
| JPS55133346A (en) | 1979-04-04 | 1980-10-17 | Asahi Chem Ind Co Ltd | Preparation of labeled peptide |
| JPS572271A (en) * | 1980-06-04 | 1982-01-07 | Asahi Chem Ind Co Ltd | Preparation of 2-aminoindolenine derivative |
| JPS5815990A (ja) | 1981-07-23 | 1983-01-29 | Asahi Chem Ind Co Ltd | インド−ル標識蛋白質の製法 |
| DE69728688T2 (de) | 1996-11-19 | 2004-08-19 | Amgen Inc., Thousand Oaks | Aryl und heteroaryl substituierte kondensierte pyrrole als entzündunghemmende mittel |
| AR046041A1 (es) * | 2003-10-03 | 2005-11-23 | Aventis Pharma Inc | Procedimiento para la preparacion de compuestos heterociclicos n-amino sustituidos |
| FR2921061B1 (fr) * | 2007-09-13 | 2009-12-18 | Idealp Pharma | Derives d'indolone pour le traitement de la malaria |
| US8431538B2 (en) | 2009-07-22 | 2013-04-30 | The Board Of Trustees Of The University Of Illinois | HDAC inhibitors and therapeutic methods of using same |
-
2010
- 2010-10-28 CA CA2779452A patent/CA2779452C/en not_active Expired - Fee Related
- 2010-10-28 PL PL10827467T patent/PL2493305T3/pl unknown
- 2010-10-28 WO PCT/US2010/054473 patent/WO2011053697A1/en not_active Ceased
- 2010-10-28 US US13/504,635 patent/US8980926B2/en active Active
- 2010-10-28 MX MX2012004914A patent/MX2012004914A/es active IP Right Grant
- 2010-10-28 EP EP10827467.1A patent/EP2493305B1/en not_active Not-in-force
- 2010-10-28 ES ES10827467.1T patent/ES2539365T3/es active Active
- 2010-10-28 JP JP2012537060A patent/JP5907876B2/ja active Active
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