JP2012530713A5 - - Google Patents
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- JP2012530713A5 JP2012530713A5 JP2012516299A JP2012516299A JP2012530713A5 JP 2012530713 A5 JP2012530713 A5 JP 2012530713A5 JP 2012516299 A JP2012516299 A JP 2012516299A JP 2012516299 A JP2012516299 A JP 2012516299A JP 2012530713 A5 JP2012530713 A5 JP 2012530713A5
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- JP
- Japan
- Prior art keywords
- alkyl
- independently
- group
- optionally
- halogen
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 1266
- 229910052736 halogen Inorganic materials 0.000 claims description 408
- 150000002367 halogens Chemical class 0.000 claims description 398
- -1 cyano, hydroxy Chemical group 0.000 claims description 346
- 125000001424 substituent group Chemical group 0.000 claims description 314
- 125000004043 oxo group Chemical group O=* 0.000 claims description 255
- 125000003545 alkoxy group Chemical group 0.000 claims description 166
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000003118 aryl group Chemical group 0.000 claims description 138
- 125000000623 heterocyclic group Chemical group 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 100
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
- 229910052799 carbon Inorganic materials 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 68
- 125000002837 carbocyclic group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 51
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 50
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 46
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 41
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
- 125000001931 aliphatic group Chemical group 0.000 claims description 32
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 23
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- QYSYONJOCHVMLX-UHFFFAOYSA-N N#COOC(NN=O)=O Chemical compound N#COOC(NN=O)=O QYSYONJOCHVMLX-UHFFFAOYSA-N 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 241000712461 unidentified influenza virus Species 0.000 claims description 7
- 230000010076 replication Effects 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 206010022000 influenza Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229940126062 Compound A Drugs 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 27
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 24
- 150000001721 carbon Chemical group 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229960005222 phenazone Drugs 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims 1
- ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 0 CC(C*)(C1)NC1c(cccc1)c1NC(*)=O Chemical compound CC(C*)(C1)NC1c(cccc1)c1NC(*)=O 0.000 description 48
- 125000004966 cyanoalkyl group Chemical group 0.000 description 13
- 125000004103 aminoalkyl group Chemical group 0.000 description 12
- 125000004181 carboxyalkyl group Chemical group 0.000 description 7
- 239000003814 drug Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MOCREHIQYHKRSW-UHFFFAOYSA-N CC(C)C(C)(C1)C1(C)C(C1)=CC=C1C(C)C Chemical compound CC(C)C(C)(C1)C1(C)C(C1)=CC=C1C(C)C MOCREHIQYHKRSW-UHFFFAOYSA-N 0.000 description 1
- SDOFCRMKKDREOD-PICGMCJFSA-M CCC(CC1)C[C@]1(N)NC(O[Re])=O Chemical compound CCC(CC1)C[C@]1(N)NC(O[Re])=O SDOFCRMKKDREOD-PICGMCJFSA-M 0.000 description 1
- NQFAQVJTYNEPAG-UHFFFAOYSA-N CCN(C)C(C)(C)C(C1)=CC=C1NS([Re])(=O)=O Chemical compound CCN(C)C(C)(C)C(C1)=CC=C1NS([Re])(=O)=O NQFAQVJTYNEPAG-UHFFFAOYSA-N 0.000 description 1
- CEZSVYMWEDJIIK-UHFFFAOYSA-N CCS(C)C(C)C#CC(CC1)CC1NC(C)=O Chemical compound CCS(C)C(C)C#CC(CC1)CC1NC(C)=O CEZSVYMWEDJIIK-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229960003971 influenza vaccine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18771309P | 2009-06-17 | 2009-06-17 | |
| US61/187,713 | 2009-06-17 | ||
| US28778109P | 2009-12-18 | 2009-12-18 | |
| US61/287,781 | 2009-12-18 | ||
| PCT/US2010/038988 WO2010148197A1 (en) | 2009-06-17 | 2010-06-17 | Inhibitors of influenza viruses replication |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014230557A Division JP2015034177A (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
| JP2014230556A Division JP6030619B2 (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012530713A JP2012530713A (ja) | 2012-12-06 |
| JP2012530713A5 true JP2012530713A5 (OSRAM) | 2013-07-25 |
| JP5721706B2 JP5721706B2 (ja) | 2015-05-20 |
Family
ID=42537408
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012516299A Expired - Fee Related JP5721706B2 (ja) | 2009-06-17 | 2010-06-17 | インフルエンザウイルス複製の阻害剤 |
| JP2014230557A Withdrawn JP2015034177A (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
| JP2014230556A Expired - Fee Related JP6030619B2 (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
| JP2016173354A Expired - Fee Related JP6348939B2 (ja) | 2009-06-17 | 2016-09-06 | インフルエンザウイルス複製の阻害剤 |
| JP2017200914A Expired - Fee Related JP6620135B2 (ja) | 2009-06-17 | 2017-10-17 | インフルエンザウイルス複製の阻害剤 |
| JP2019181224A Withdrawn JP2020011990A (ja) | 2009-06-17 | 2019-10-01 | インフルエンザウイルス複製の阻害剤 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014230557A Withdrawn JP2015034177A (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
| JP2014230556A Expired - Fee Related JP6030619B2 (ja) | 2009-06-17 | 2014-11-13 | インフルエンザウイルス複製の阻害剤 |
| JP2016173354A Expired - Fee Related JP6348939B2 (ja) | 2009-06-17 | 2016-09-06 | インフルエンザウイルス複製の阻害剤 |
| JP2017200914A Expired - Fee Related JP6620135B2 (ja) | 2009-06-17 | 2017-10-17 | インフルエンザウイルス複製の阻害剤 |
| JP2019181224A Withdrawn JP2020011990A (ja) | 2009-06-17 | 2019-10-01 | インフルエンザウイルス複製の阻害剤 |
Country Status (37)
Families Citing this family (63)
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| US8921376B2 (en) * | 2005-05-20 | 2014-12-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| SG10201405826RA (en) | 2009-06-17 | 2014-12-30 | Vertex Pharma | Inhibitors of influenza viruses replication |
| CA2822062A1 (en) * | 2010-12-16 | 2012-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| KR20130128436A (ko) * | 2010-12-16 | 2013-11-26 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| RU2013132681A (ru) * | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| CN103702980B (zh) | 2011-07-04 | 2016-10-05 | 罗达制药生物技术有限责任公司 | 环胺衍生物作为ep4受体拮抗剂 |
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| UA118010C2 (uk) * | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| US10323012B2 (en) * | 2012-06-05 | 2019-06-18 | Hong Kong Baptist University | Miliusanes as antiviral agents |
| EP2858984A1 (en) * | 2012-06-08 | 2015-04-15 | Vertex Pharmaceuticals Inc. | Inhibitors of influenza viruses replication |
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| JP6989509B2 (ja) * | 2016-01-20 | 2022-01-05 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | インフルエンザウイルス感染における使用のためのアリール置換ピリミジン |
| WO2017133667A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Pyrimidine and pyridine derivatives and use in treatment, amelioration or prevention of influenza thereof |
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