JP2011529071A5 - - Google Patents
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- Publication number
- JP2011529071A5 JP2011529071A5 JP2011520188A JP2011520188A JP2011529071A5 JP 2011529071 A5 JP2011529071 A5 JP 2011529071A5 JP 2011520188 A JP2011520188 A JP 2011520188A JP 2011520188 A JP2011520188 A JP 2011520188A JP 2011529071 A5 JP2011529071 A5 JP 2011529071A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- formula
- oxy
- carbonyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims 26
- 238000000034 method Methods 0.000 claims 6
- 208000036142 Viral infection Diseases 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 208000037357 HIV infectious disease Diseases 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- QDZZDVQGBKTLHV-UHFFFAOYSA-N (2,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1F QDZZDVQGBKTLHV-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 241000282412 Homo Species 0.000 claims 1
- 241000872931 Myoporum sandwicense Species 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NRPFTENKNHJRIA-APWZRJJASA-N methyl ({[({[(4as,13ar)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1h-pyrido[1,2-a]pyrrolo[1',2':3,4]imidazo[1,2-d]pyrazin-10-yl]oxy}methyl)oxy]carbonyl}oxy)acetate Chemical compound C([C@H]1N2CCC[C@@H]2CN1C(=O)C1=C(C2=O)OCOC(=O)OCC(=O)OC)N1C=C2C(=O)NCC1=CC=C(F)C=C1F NRPFTENKNHJRIA-APWZRJJASA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- YSPZJEZKZYYLCX-WMCAAGNKSA-N O=C1C(OCc2ccccc2)=C(C(N2[C@@H](C3)N(CCC4)C4C2)=O)N3C=C1Br Chemical compound O=C1C(OCc2ccccc2)=C(C(N2[C@@H](C3)N(CCC4)C4C2)=O)N3C=C1Br YSPZJEZKZYYLCX-WMCAAGNKSA-N 0.000 description 2
- 0 CCCC[C@](C1)N[C@@](CN(C=C(C(NCc(ccc(F)c2)c2F)=O)C2=O)C3=C2OCOC(O*)=O)N1C3=O Chemical compound CCCC[C@](C1)N[C@@](CN(C=C(C(NCc(ccc(F)c2)c2F)=O)C2=O)C3=C2OCOC(O*)=O)N1C3=O 0.000 description 1
- BQCJQVPKXUQHNJ-UHFFFAOYSA-N COC(C(N(CC(CO)O)C=C(C1=O)Br)=C1OCc1ccccc1)=O Chemical compound COC(C(N(CC(CO)O)C=C(C1=O)Br)=C1OCc1ccccc1)=O BQCJQVPKXUQHNJ-UHFFFAOYSA-N 0.000 description 1
- JUVSRACZYLMJQD-UHFFFAOYSA-N COC(C(N(CC(CO)O)C=CC1=O)=C1OCc1ccccc1)=O Chemical compound COC(C(N(CC(CO)O)C=CC1=O)=C1OCc1ccccc1)=O JUVSRACZYLMJQD-UHFFFAOYSA-N 0.000 description 1
- GTDMSZVBNIIIPJ-UHFFFAOYSA-N COC(C(N(CC(O)O)C=C(C1=O)Br)=C1OCc1ccccc1)=O Chemical compound COC(C(N(CC(O)O)C=C(C1=O)Br)=C1OCc1ccccc1)=O GTDMSZVBNIIIPJ-UHFFFAOYSA-N 0.000 description 1
- AUKXFNABVHIUAC-RXMQYKEDSA-N NC[C@@H]1NCCC1 Chemical compound NC[C@@H]1NCCC1 AUKXFNABVHIUAC-RXMQYKEDSA-N 0.000 description 1
- ZJACLLIMBJZRLT-CJNGLKHVSA-N NOC1=C(C(N2[C@@H](C3)N(CCC4)[C@H]4C2)=O)N3C=C(C(NCc(ccc(F)c2)c2F)=O)C1=O Chemical compound NOC1=C(C(N2[C@@H](C3)N(CCC4)[C@H]4C2)=O)N3C=C(C(NCc(ccc(F)c2)c2F)=O)C1=O ZJACLLIMBJZRLT-CJNGLKHVSA-N 0.000 description 1
- WIKNSQGGNPAYTD-AKRCKQFNSA-N O=C(C(C1=O)=CN(C[C@@H](N(CCC2)C2C2)N2C2=O)C2=C1OCc1ccccc1)NCc(ccc(F)c1)c1F Chemical compound O=C(C(C1=O)=CN(C[C@@H](N(CCC2)C2C2)N2C2=O)C2=C1OCc1ccccc1)NCc(ccc(F)c1)c1F WIKNSQGGNPAYTD-AKRCKQFNSA-N 0.000 description 1
- TUBHMQLHDDHKCJ-CJNGLKHVSA-N OC1=C(C(N2[C@@H](C3)N(CCC4)[C@H]4C2)=O)N3C=C(C(NCc(ccc(F)c2)c2F)=O)C1=O Chemical compound OC1=C(C(N2[C@@H](C3)N(CCC4)[C@H]4C2)=O)N3C=C(C(NCc(ccc(F)c2)c2F)=O)C1=O TUBHMQLHDDHKCJ-CJNGLKHVSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8360308P | 2008-07-25 | 2008-07-25 | |
| US61/083,603 | 2008-07-25 | ||
| PCT/US2009/051501 WO2010011816A1 (en) | 2008-07-25 | 2009-07-23 | Chemical compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014084833A Division JP5758024B2 (ja) | 2008-07-25 | 2014-04-16 | 化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011529071A JP2011529071A (ja) | 2011-12-01 |
| JP2011529071A5 true JP2011529071A5 (https=) | 2012-09-06 |
| JP5551697B2 JP5551697B2 (ja) | 2014-07-16 |
Family
ID=41570597
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011520188A Active JP5551697B2 (ja) | 2008-07-25 | 2009-07-23 | 化合物 |
| JP2014084833A Active JP5758024B2 (ja) | 2008-07-25 | 2014-04-16 | 化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014084833A Active JP5758024B2 (ja) | 2008-07-25 | 2014-04-16 | 化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US8183372B2 (https=) |
| EP (2) | EP2330902B1 (https=) |
| JP (2) | JP5551697B2 (https=) |
| ES (2) | ES2449752T3 (https=) |
| WO (1) | WO2010011816A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2320909B8 (en) * | 2008-07-25 | 2016-03-30 | VIIV Healthcare Company | Chemical compounds |
| CA2744019C (en) | 2008-12-11 | 2017-03-14 | Shionogi & Co., Ltd. | Synthesis of carbamoylpyridone hiv integrase inhibitors and intermediates |
| KR101682058B1 (ko) * | 2008-12-11 | 2016-12-02 | 비이브 헬쓰케어 컴퍼니 | 카르바모일피리돈 ｈｉｖ 인테그라제 억제제를 위한 제조방법 및 중간체 |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| MX2013003139A (es) | 2010-09-24 | 2013-06-18 | Shionogi & Co | Profarmaco de derivado de carbamoilpiridona policiclica substituida. |
| EA030003B1 (ru) | 2012-12-21 | 2018-06-29 | Джилид Сайэнс, Инк. | Полициклическое карбамоилпиридоновое соединение и его фармацевтическое применение для лечения вич-инфекции |
| NO2865735T3 (https=) | 2013-07-12 | 2018-07-21 | ||
| SI3019503T1 (sl) | 2013-07-12 | 2017-11-30 | Gilead Sciences, Inc. | Policiklične karbamoilpiridonske spojine in njihova uporaba za zdravljenje HIV infekcij |
| NO2717902T3 (https=) | 2014-06-20 | 2018-06-23 | ||
| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| TW201613936A (en) | 2014-06-20 | 2016-04-16 | Gilead Sciences Inc | Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide |
| TWI695003B (zh) | 2014-12-23 | 2020-06-01 | 美商基利科學股份有限公司 | 多環胺甲醯基吡啶酮化合物及其醫藥用途 |
| JP6402259B2 (ja) | 2015-04-02 | 2018-10-10 | ギリアード サイエンシーズ， インコーポレイテッド | 多環式カルバモイルピリドン化合物およびそれらの薬学的使用 |
| JOP20190130A1 (ar) | 2016-12-02 | 2019-06-02 | Merck Sharp & Dohme | مركبات حلقية غير متجانسة رباعية الحلقات مفيدة كمثبطات إنزيم مدمج لفيروس نقص المناعة البشرية (hiv) |
| JP6924839B2 (ja) | 2017-10-06 | 2021-08-25 | 塩野義製薬株式会社 | 置換された多環性ピリドン誘導体の立体選択的な製造方法 |
| CN109879843B (zh) * | 2019-02-11 | 2020-08-28 | 常州制药厂有限公司 | 一种巴洛沙韦的中间体及其制备方法与应用 |
| WO2020197991A1 (en) | 2019-03-22 | 2020-10-01 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and their pharmaceutical use |
| US20200398978A1 (en) | 2019-06-20 | 2020-12-24 | Bell Helicopter Textron Inc. | Low-drag rotor blade extension |
| IL295677B1 (en) | 2020-02-24 | 2026-04-01 | Gilead Sciences Inc | Tetracyclic compounds for the treatment of HIV infection |
| CA3192145A1 (en) | 2020-09-30 | 2022-04-07 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| FI4196479T3 (fi) | 2021-01-19 | 2024-01-17 | Gilead Sciences Inc | Substituoituja pyridotriatsiiniyhdisteitä ja niiden käyttöjä |
| EP4294813B1 (en) * | 2021-02-16 | 2025-09-10 | Merck Sharp & Dohme LLC | Tetracyclic heterocycle compounds useful as hiv integrase inhibitors |
| TWI856796B (zh) | 2022-04-06 | 2024-09-21 | 美商基利科學股份有限公司 | 橋聯三環胺甲醯基吡啶酮化合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB427857A (en) | 1934-08-02 | 1935-05-01 | Newsum Sons & Company Ltd H | A new or improved system of construction for skeleton structures, particularly vehicle body frames and door frames |
| JP2005516916A (ja) * | 2001-12-11 | 2005-06-09 | スミスクライン ビーチャム コーポレーション | 抗ヘルペス薬としてのピラゾロ−ピリジン誘導体 |
| US20060246196A1 (en) | 2005-04-27 | 2006-11-02 | Lawson John A | Low-alcohol, low-calorie wine |
| US8129385B2 (en) | 2005-04-28 | 2012-03-06 | Shionogi & Co., Ltd. | Substituted 5-hydroxy-3,4,6,9,9a, 10-hexanhydro-2h-1-oxa04a,8a-diaza-anthracene-6,10-dioness |
| TW200716632A (en) * | 2005-05-16 | 2007-05-01 | Gilead Sciences Inc | Integrase inhibitor compounds |
| EP2102158A1 (en) * | 2006-12-11 | 2009-09-23 | Topo Target A/S | Prodrugs of diphenyl ox- indol- 2 -one compounds for the treatment of cancers |
-
2009
- 2009-07-23 EP EP09800993A patent/EP2330902B1/en active Active
- 2009-07-23 EP EP12159281.0A patent/EP2465858B1/en active Active
- 2009-07-23 WO PCT/US2009/051501 patent/WO2010011816A1/en not_active Ceased
- 2009-07-23 ES ES12159281.0T patent/ES2449752T3/es active Active
- 2009-07-23 ES ES09800993T patent/ES2395705T3/es active Active
- 2009-07-23 US US13/055,046 patent/US8183372B2/en active Active
- 2009-07-23 JP JP2011520188A patent/JP5551697B2/ja active Active
-
2012
- 2012-04-19 US US13/450,784 patent/US20120209000A1/en not_active Abandoned
-
2013
- 2013-02-19 US US13/770,336 patent/US8691823B2/en active Active
-
2014
- 2014-04-16 JP JP2014084833A patent/JP5758024B2/ja active Active
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