ES2645192T3 - Compuestos de carbamoilpiridona policíclica y su uso para el tratamiento de infecciones por VIH - Google Patents
Compuestos de carbamoilpiridona policíclica y su uso para el tratamiento de infecciones por VIH Download PDFInfo
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- ES2645192T3 ES2645192T3 ES14745052.2T ES14745052T ES2645192T3 ES 2645192 T3 ES2645192 T3 ES 2645192T3 ES 14745052 T ES14745052 T ES 14745052T ES 2645192 T3 ES2645192 T3 ES 2645192T3
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- hiv
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- 208000031886 HIV Infections Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 150000003839 salts Chemical class 0.000 abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
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- 229940124597 therapeutic agent Drugs 0.000 description 25
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
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| DK3019503T3 (da) * | 2013-07-12 | 2017-11-20 | Gilead Sciences Inc | Polycykliske-carbamoylpyridon-forbindelser og anvendelse deraf til behandling af hiv-infektioner |
| NO2865735T3 (enExample) | 2013-07-12 | 2018-07-21 | ||
| 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 |
| EP3757105B1 (en) | 2014-08-22 | 2024-07-24 | Shionogi & Co., Ltd. | Polycyclic pyridone derivative having integrase inhibitory activity |
| DK3097102T3 (en) | 2015-03-04 | 2018-01-22 | Gilead Sciences Inc | TOLL-LIKE RECEPTOR MODULATING 4,6-DIAMINO-PYRIDO [3,2-D] PYRIMIDINE COMPOUNDS |
| TR201905009T4 (tr) * | 2015-04-02 | 2019-05-21 | Gilead Sciences Inc | Polisiklik-karbamoilpiridon bileşikleri ve bunların farmasötik kullanımları. |
| JP2018525412A (ja) | 2015-08-26 | 2018-09-06 | ギリアード サイエンシーズ, インコーポレイテッド | 重水素化トール様受容体調節因子 |
| JP2018527366A (ja) | 2015-09-15 | 2018-09-20 | ギリアード サイエンシーズ, インコーポレイテッド | HIVを処置するためのtoll様レセプターのモジュレーター |
| WO2018044838A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| US20190183901A1 (en) * | 2016-08-31 | 2019-06-20 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| WO2018045150A1 (en) | 2016-09-02 | 2018-03-08 | Gilead Sciences, Inc. | 4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators |
| MA46093A (fr) | 2016-09-02 | 2021-05-19 | Gilead Sciences Inc | Composés modulateurs du recepteur de type toll |
| 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) |
| CA3102063A1 (en) | 2018-05-31 | 2019-12-05 | Shionogi & Co., Ltd. | Polycyclic carbamoylpyridone derivative |
| US11453669B2 (en) | 2018-05-31 | 2022-09-27 | Shionogi & Co., Ltd. | Polycyclic pyridone derivative |
| IL286328B1 (en) | 2019-03-22 | 2026-04-01 | Gilead Sciences Inc | Tricyclic bridging compounds of carbamoylpyridone and their pharmaceutical use |
| US20220305115A1 (en) | 2019-06-18 | 2022-09-29 | Janssen Sciences Ireland Unlimited Company | Combination of hepatitis b virus (hbv) vaccines and pyridopyrimidine derivatives |
| US20200398978A1 (en) | 2019-06-20 | 2020-12-24 | Bell Helicopter Textron Inc. | Low-drag rotor blade extension |
| US11248005B2 (en) | 2019-07-08 | 2022-02-15 | Lupin Limited | Process for preparation of intermediates used for the synthesis of HIV integrase inhibitor |
| EP4066839A4 (en) | 2019-11-28 | 2023-12-27 | Shionogi & Co., Ltd | PROPHYLACTIC AND THERAPEUTIC MEDICINAL PRODUCT FOR HIV INFECTIOUS DISEASES, CHARACTERIZED BY CONTAINING THE COMBINATION OF INTEGRAS INHIBITORS AND ANTI-HIV AGENTS |
| US12577241B2 (en) | 2019-11-28 | 2026-03-17 | Shionogi & Co., Ltd. | Polycyclic pyridopyrazine derivative |
| CR20220418A (es) | 2020-02-24 | 2022-10-10 | Gilead Sciences Inc | Compuestos tetracíclicos para el tratamiento de infecciones por vih |
| CA3192145A1 (en) | 2020-09-30 | 2022-04-07 | Gilead Sciences, Inc. | Bridged tricyclic carbamoylpyridone compounds and uses thereof |
| JP7591155B2 (ja) | 2021-01-19 | 2024-11-27 | ギリアード サイエンシーズ, インコーポレイテッド | 置換ピリドトリアジン化合物及びその使用 |
| 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 |
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