ES2905550T3 - Compuestos de pirazolo- y triazolo-pirimidina antivirales contra VSR - Google Patents
Compuestos de pirazolo- y triazolo-pirimidina antivirales contra VSR Download PDFInfo
- Publication number
- ES2905550T3 ES2905550T3 ES16719387T ES16719387T ES2905550T3 ES 2905550 T3 ES2905550 T3 ES 2905550T3 ES 16719387 T ES16719387 T ES 16719387T ES 16719387 T ES16719387 T ES 16719387T ES 2905550 T3 ES2905550 T3 ES 2905550T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- mmol
- substituted
- hydroxycarbonyl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims abstract 73
- 125000001424 substituent group Chemical group 0.000 claims abstract 31
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 27
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract 25
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- -1 cyano, hydroxycarbonyl Chemical group 0.000 claims abstract 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 239000001257 hydrogen Substances 0.000 claims abstract 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 3
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 3
- 125000006684 polyhaloalkyl group Polymers 0.000 claims abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 2
- 125000002541 furyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 241000820057 Ithone Species 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 claims 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 1
- 229940126187 RSV fusion inhibitor Drugs 0.000 claims 1
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims 1
- IMIDOCRTMDIQIJ-UHFFFAOYSA-N aminocarb Chemical compound CNC(=O)OC1=CC=C(N(C)C)C(C)=C1 IMIDOCRTMDIQIJ-UHFFFAOYSA-N 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 210000001217 buttock Anatomy 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000030925 respiratory syncytial virus infectious disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- YAVKJDAFUSDEAL-UHFFFAOYSA-N (7-ethyl-2-pyridin-2-ylpyrazolo[1,5-a]pyrimidin-5-yl)-(2-methylpiperidin-1-yl)methanone Chemical compound N=1N2C(CC)=CC(C(=O)N3C(CCCC3)C)=NC2=CC=1C1=CC=CC=N1 YAVKJDAFUSDEAL-UHFFFAOYSA-N 0.000 abstract 1
- WWWLNMMOFNHKQA-UHFFFAOYSA-N (7-ethyl-2-thiophen-3-ylpyrazolo[1,5-a]pyrimidin-5-yl)-(2-methylpiperidin-1-yl)methanone Chemical compound CCC1=CC(=NC2=CC(=NN12)C1=CSC=C1)C(=O)N1CCCCC1C WWWLNMMOFNHKQA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 abstract 1
- 125000000850 2H-chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 abstract 1
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562153753P | 2015-04-28 | 2015-04-28 | |
| US201562204390P | 2015-08-12 | 2015-08-12 | |
| PCT/EP2016/059392 WO2016174079A1 (en) | 2015-04-28 | 2016-04-27 | Rsv antiviral pyrazolo- and triazolo-pyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2905550T3 true ES2905550T3 (es) | 2022-04-11 |
Family
ID=55860847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16719387T Active ES2905550T3 (es) | 2015-04-28 | 2016-04-27 | Compuestos de pirazolo- y triazolo-pirimidina antivirales contra VSR |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US10208048B2 (https=) |
| EP (1) | EP3288942B1 (https=) |
| JP (1) | JP6698693B2 (https=) |
| KR (1) | KR102538565B1 (https=) |
| CN (1) | CN107531715B (https=) |
| AU (1) | AU2016254700B2 (https=) |
| BR (1) | BR112017023263B1 (https=) |
| CA (1) | CA2981404C (https=) |
| CL (1) | CL2017002709A1 (https=) |
| CY (1) | CY1125329T1 (https=) |
| DK (1) | DK3288942T3 (https=) |
| EA (1) | EA035689B1 (https=) |
| ES (1) | ES2905550T3 (https=) |
| HR (1) | HRP20211728T1 (https=) |
| HU (1) | HUE057626T2 (https=) |
| IL (1) | IL254750B (https=) |
| JO (1) | JO3637B1 (https=) |
| LT (1) | LT3288942T (https=) |
| MA (1) | MA41974A (https=) |
| MX (1) | MX369040B (https=) |
| PH (1) | PH12017501958B1 (https=) |
| PL (1) | PL3288942T3 (https=) |
| PT (1) | PT3288942T (https=) |
| SG (1) | SG11201708786SA (https=) |
| SI (1) | SI3288942T1 (https=) |
| TW (1) | TWI703146B (https=) |
| UA (1) | UA120448C2 (https=) |
| WO (1) | WO2016174079A1 (https=) |
| ZA (1) | ZA201707320B (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3637B1 (ar) * | 2015-04-28 | 2020-08-27 | Janssen Sciences Ireland Uc | مركبات بيرازولو- وترايازولو- بيريميدين مضادة للفيروسات rsv |
| TW201932470A (zh) | 2017-11-29 | 2019-08-16 | 愛爾蘭商健生科學愛爾蘭無限公司 | 具有抗ｒｓｖ活性之吡唑并嘧啶 |
| TW201936193A (zh) * | 2017-12-05 | 2019-09-16 | 愛爾蘭商健生科學愛爾蘭無限公司 | 使用組合產品治療ｒｓｖ |
| SG11202006141RA (en) | 2018-01-31 | 2020-07-29 | Janssen Sciences Ireland Unlimited Co | Cycloalkyl substituted pyrazolopyrimidines having activity against rsv |
| US11708369B2 (en) | 2018-04-23 | 2023-07-25 | Janssen Sciences Ireland Unlimited Company | Heteroaromatic compounds having activity against RSV |
| CA3099311A1 (en) * | 2018-05-03 | 2019-11-07 | Georgia State University Research Foundation, Inc. | Inhibitors of rsv replication and applications thereof |
| EA202191482A1 (ru) * | 2018-11-26 | 2021-12-14 | Янссен Сайенсиз Айрлэнд Анлимитед Компани | Другие гетероароматические соединения, обладающие активностью против rsv |
| JPWO2020138015A1 (ja) | 2018-12-27 | 2021-11-18 | 大正製薬株式会社 | ピラゾロ［１，５−ａ］ピリミジン大環状化合物 |
| EA202193223A1 (ru) | 2019-05-23 | 2022-03-10 | Янссен Сайенсиз Айрлэнд Анлимитед Компани | Другие гетероароматические соединения, действующие против рсв |
| CN111440173B (zh) * | 2020-03-27 | 2021-05-14 | 山东大学 | 一种pi3k抑制剂的制备方法 |
| WO2022020891A1 (en) * | 2020-07-27 | 2022-02-03 | Esfam Biotech Pty Ltd | Methods of prophylaxis and treatment of corona virus |
| WO2022020889A1 (en) * | 2020-07-27 | 2022-02-03 | Esfam Biotech Pty Ltd | Method of treatment of cytomegalovirus |
| CA3200111C (en) | 2020-10-28 | 2025-02-18 | Shionogi & Co., Ltd. | AMIDE DERIVATIVE WITH ANTIVIRAL ACTIVITY |
| CN117120050A (zh) | 2021-02-08 | 2023-11-24 | 纽约哥伦比亚大学董事会 | 用于治疗神经和精神疾病的受氧杂-伊博格碱启发的类似物 |
| CN116425754A (zh) * | 2021-12-30 | 2023-07-14 | 苏州爱科百发生物医药技术有限公司 | 芳杂双环化合物及其抗病毒用途 |
| CA3259556A1 (en) * | 2022-06-17 | 2023-12-21 | Trawsfynydd Therapeutics, Inc. | COMPOUNDS FOR THE TREATMENT OF CORONAVIRUS INFECTION |
| WO2024121264A1 (en) | 2022-12-09 | 2024-06-13 | Syngenta Crop Protection Ag | Insecticidal compound based on pyrazole derivatives |
| WO2024121261A1 (en) | 2022-12-09 | 2024-06-13 | Syngenta Crop Protection Ag | Insecticidal compound based on pyrazole derivatives |
| WO2024121263A1 (en) | 2022-12-09 | 2024-06-13 | Syngenta Crop Protection Ag | Insecticidal compound based on pyrazole derivatives |
| WO2024121262A1 (en) | 2022-12-09 | 2024-06-13 | Syngenta Crop Protection Ag | Insecticidal compound based on pyrazole derivatives |
| WO2026003043A1 (en) * | 2024-06-26 | 2026-01-02 | Janssen Pharmaceutica Nv | Malt1 inhibitors |
| WO2026003049A1 (en) * | 2024-06-26 | 2026-01-02 | Janssen Pharmaceutica Nv | Malt1 inhibitors |
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