JP2015514761A5 - - Google Patents
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- Publication number
- JP2015514761A5 JP2015514761A5 JP2015507030A JP2015507030A JP2015514761A5 JP 2015514761 A5 JP2015514761 A5 JP 2015514761A5 JP 2015507030 A JP2015507030 A JP 2015507030A JP 2015507030 A JP2015507030 A JP 2015507030A JP 2015514761 A5 JP2015514761 A5 JP 2015514761A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- aryl
- halo
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 230000011987 methylation Effects 0.000 claims 2
- 238000007069 methylation reaction Methods 0.000 claims 2
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims 1
- 208000009889 Herpes Simplex Diseases 0.000 claims 1
- 208000007514 Herpes zoster Diseases 0.000 claims 1
- SMLPFNLYOFQEGY-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)CC1(N)C(=O)OCC(CO)OCN1C(N=C(N)NC2=O)=C2N=C1 SMLPFNLYOFQEGY-UHFFFAOYSA-N 0.000 claims 1
- DTHSOQSPFIAEJV-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-(4-bromophenyl)cyclopropane-1-carboxylate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC(=O)C1(N)CC1C1=CC=C(Br)C=C1 DTHSOQSPFIAEJV-UHFFFAOYSA-N 0.000 claims 1
- CQSGIFZPQZDTIZ-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-(furan-2-yl)cyclopropane-1-carboxylate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC(=O)C1(N)CC1C1=CC=CO1 CQSGIFZPQZDTIZ-UHFFFAOYSA-N 0.000 claims 1
- MRWPBZBQWRSNRB-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC(=O)C1(N)CC1C(F)(F)F MRWPBZBQWRSNRB-UHFFFAOYSA-N 0.000 claims 1
- MVNARZKXRUBFFA-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-methylcyclopropane-1-carboxylate Chemical compound CC1CC1(N)C(=O)OCC(CO)OCN1C(N=C(N)NC2=O)=C2N=C1 MVNARZKXRUBFFA-UHFFFAOYSA-N 0.000 claims 1
- BFZPBCAOEOHGJC-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-phenylcyclopropane-1-carboxylate Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC(=O)C1(N)CC1C1=CC=CC=C1 BFZPBCAOEOHGJC-UHFFFAOYSA-N 0.000 claims 1
- OXUFLDGSKJDLPU-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-hydroxypropyl] 1-amino-2-pyridin-2-ylcyclopropane-1-carboxylate Chemical group C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC(=O)C1(N)CC1C1=CC=CC=N1 OXUFLDGSKJDLPU-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- -1 2H-pyrrolyl Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004937 4H-carbazolyl group Chemical group C=1(C=CCC2=C3C=CC=CC3=NC12)* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261635931P | 2012-04-20 | 2012-04-20 | |
| US61/635,931 | 2012-04-20 | ||
| PCT/US2013/035042 WO2013158367A1 (en) | 2012-04-20 | 2013-04-02 | Cyclopropanecarboxylate esters of purine analogues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015514761A JP2015514761A (ja) | 2015-05-21 |
| JP2015514761A5 true JP2015514761A5 (https=) | 2016-06-02 |
| JP6177879B2 JP6177879B2 (ja) | 2017-08-09 |
Family
ID=49380678
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015507030A Expired - Fee Related JP6177879B2 (ja) | 2012-04-20 | 2013-04-02 | プリンアナログのシクロプロパンカルボキシレートエステル |
| JP2015507031A Expired - Fee Related JP6174119B2 (ja) | 2012-04-20 | 2013-04-03 | プロテインキナーゼ阻害薬としてのインドリン−２−オン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015507031A Expired - Fee Related JP6174119B2 (ja) | 2012-04-20 | 2013-04-03 | プロテインキナーゼ阻害薬としてのインドリン−２−オン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8969361B2 (https=) |
| EP (2) | EP2838538B1 (https=) |
| JP (2) | JP6177879B2 (https=) |
| KR (2) | KR101774861B1 (https=) |
| CN (2) | CN104394868A (https=) |
| AU (2) | AU2013249708B2 (https=) |
| BR (1) | BR112014026182A2 (https=) |
| ES (2) | ES2621257T3 (https=) |
| IL (2) | IL235098A0 (https=) |
| IN (2) | IN2014MN02105A (https=) |
| RU (2) | RU2642463C2 (https=) |
| TW (2) | TWI496784B (https=) |
| WO (2) | WO2013158367A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014155301A1 (en) * | 2013-03-26 | 2014-10-02 | Piramal Enterprises Limited | Substituted bicyclic compounds as inhibitors of ezh2 |
| ES2808920T3 (es) | 2015-11-06 | 2021-03-02 | Hoffmann La Roche | Derivados de indolin-2-ona |
| CN106831707B (zh) * | 2016-12-28 | 2019-09-20 | 杭州市西溪医院 | 作为c-Met激酶抑制剂的苯并杂环类衍生物及其医疗用途 |
| GB201709456D0 (en) * | 2017-06-14 | 2017-07-26 | Ucb Biopharma Sprl | Therapeutic agents |
| EP4267642A1 (de) | 2020-12-23 | 2023-11-01 | Basf Se | Neuer katalysator zur herstellung von polyurethanen |
| CN113307799B (zh) * | 2021-05-21 | 2022-07-19 | 大连医科大学 | 一种检测葡萄糖醛酸转移酶1a1荧光探针及其应用 |
| CN113999221B (zh) * | 2021-11-04 | 2024-04-05 | 南京中医药大学 | 6-位取代的吲哚酮衍生物及其医药用途 |
| CN114380802B (zh) * | 2022-01-07 | 2023-11-17 | 贵州大学 | 一类含咔唑基咪唑盐类化合物及其制备方法和应用 |
| WO2024110395A1 (de) | 2022-11-24 | 2024-05-30 | Basf Se | Verbesserung der lagerstabilität von hydrofluorolefinen in aminhaltigen polyolkomponenten für die herstellung von polyurethanen |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT351865B (de) | 1977-04-01 | 1979-08-27 | Hoffmann La Roche | Akarizide mittel |
| US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
| EA005032B1 (ru) * | 1998-05-29 | 2004-10-28 | Сьюджен, Инк. | Пирролзамещенные 2-индолиноны (варианты), фармацевтическая композиция (варианты), способ модулирования каталитической активности протеинкиназы, способ лечения или профилактики нарушения в организме, связанного с протеинкиназой |
| SI1255752T1 (sl) | 2000-02-15 | 2007-12-31 | Pharmacia & Upjohn Co Llc | S pirolom substituirani zaviralci 2-indolinon protein kinaza |
| US20090264494A1 (en) * | 2002-10-18 | 2009-10-22 | Board Of Regents, The University Of Texas System | Use of neuroprotective 3-substituted indolone compositions |
| JP2007509173A (ja) | 2003-10-24 | 2007-04-12 | シエーリング アクチエンゲゼルシャフト | インドリノン誘導体類及び疾病状態、例えば癌の処理へのそれらの使用 |
| GT200500321A (es) | 2004-11-09 | 2006-09-04 | Compuestos y composiciones como inhibidores de proteina kinase. | |
| WO2006127217A2 (en) * | 2005-05-25 | 2006-11-30 | Eli Lilly And Company | Cyclopropanecarboxylate esters of acyclovir |
| BRPI0616378A2 (pt) | 2005-09-22 | 2011-06-21 | Scripps Research Inst | inibidores de proteìna cinase baseados em alcóxi indolinona e métodos para modulação da atividade catalìtica |
| CN1850794A (zh) * | 2006-05-30 | 2006-10-25 | 中国医学科学院医药生物技术研究所 | 3－酰胺基取代苯甲酰脲类化合物及其抗肿瘤作用 |
| CN101541788A (zh) | 2006-12-11 | 2009-09-23 | Irm责任有限公司 | 作为激酶抑制剂的化合物和组合物 |
| MX2009005921A (es) * | 2006-12-13 | 2009-06-17 | Hoffmann La Roche | Formulacion en polvo del valganciclovir. |
| EP2167465A1 (en) | 2007-06-12 | 2010-03-31 | Boehringer Ingelheim International GmbH | Indolinone derivatives and their use in treating disease-states such as cancer |
| US7846793B2 (en) | 2007-10-03 | 2010-12-07 | Applied Materials, Inc. | Plasma surface treatment for SI and metal nanocrystal nucleation |
| WO2009111739A2 (en) * | 2008-03-07 | 2009-09-11 | Exley Ray W | Treatment of herpes virus related diseases |
| WO2009142827A2 (en) * | 2008-03-28 | 2009-11-26 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Compounds and methods for the treatment of viral infection |
| UY31929A (es) * | 2008-06-25 | 2010-01-05 | Irm Llc | Compuestos y composiciones como inhibidores de cinasa |
| RU2011103189A (ru) * | 2008-06-30 | 2012-08-10 | Силин Фармасьютикалз, Инк. (Us) | Производные оксиндола |
| US20100298376A1 (en) * | 2009-05-13 | 2010-11-25 | Board Of Regents, The University Of Texas System | Use of novel neuroprotective 3-substituted indolone compositions |
| GB201014374D0 (en) * | 2010-08-27 | 2010-10-13 | Univ Greenwich | Novel hybrid compounds |
| EA201390532A1 (ru) * | 2010-10-08 | 2013-09-30 | Новартис Аг | Композиции сульфамидых ингибиторов ns3, содержащие витамин е |
-
2013
- 2013-04-02 US US13/855,692 patent/US8969361B2/en not_active Expired - Fee Related
- 2013-04-02 JP JP2015507030A patent/JP6177879B2/ja not_active Expired - Fee Related
- 2013-04-02 KR KR1020147032458A patent/KR101774861B1/ko not_active Expired - Fee Related
- 2013-04-02 WO PCT/US2013/035042 patent/WO2013158367A1/en not_active Ceased
- 2013-04-02 CN CN201380032742.6A patent/CN104394868A/zh active Pending
- 2013-04-02 EP EP13778039.1A patent/EP2838538B1/en not_active Not-in-force
- 2013-04-02 ES ES13778039.1T patent/ES2621257T3/es active Active
- 2013-04-02 RU RU2014145481A patent/RU2642463C2/ru not_active IP Right Cessation
- 2013-04-02 IN IN2105MUN2014 patent/IN2014MN02105A/en unknown
- 2013-04-02 AU AU2013249708A patent/AU2013249708B2/en not_active Ceased
- 2013-04-03 IN IN2107MUN2014 patent/IN2014MN02107A/en unknown
- 2013-04-03 AU AU2013249714A patent/AU2013249714B2/en not_active Ceased
- 2013-04-03 BR BR112014026182A patent/BR112014026182A2/pt not_active Application Discontinuation
- 2013-04-03 ES ES13777764.5T patent/ES2600467T3/es active Active
- 2013-04-03 CN CN201380020494.3A patent/CN104302287B/zh not_active Expired - Fee Related
- 2013-04-03 RU RU2014145480A patent/RU2627706C2/ru not_active IP Right Cessation
- 2013-04-03 WO PCT/US2013/035177 patent/WO2013158373A1/en not_active Ceased
- 2013-04-03 JP JP2015507031A patent/JP6174119B2/ja not_active Expired - Fee Related
- 2013-04-03 EP EP13777764.5A patent/EP2838531B1/en not_active Not-in-force
- 2013-04-03 KR KR1020147031413A patent/KR101778095B1/ko not_active Expired - Fee Related
- 2013-04-03 US US13/855,916 patent/US8946282B2/en not_active Expired - Fee Related
- 2013-04-19 TW TW102113981A patent/TWI496784B/zh not_active IP Right Cessation
- 2013-04-19 TW TW102113856A patent/TWI458709B/zh not_active IP Right Cessation
-
2014
- 2014-10-19 IL IL235098A patent/IL235098A0/en unknown
- 2014-10-19 IL IL235097A patent/IL235097A/en not_active IP Right Cessation
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