RU2734248C2 - Спироиндолиновые соединения для лечения и профилактики респираторно-синцитиального вируса (rsv) - Google Patents
Спироиндолиновые соединения для лечения и профилактики респираторно-синцитиального вируса (rsv) Download PDFInfo
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- RU2734248C2 RU2734248C2 RU2017113026A RU2017113026A RU2734248C2 RU 2734248 C2 RU2734248 C2 RU 2734248C2 RU 2017113026 A RU2017113026 A RU 2017113026A RU 2017113026 A RU2017113026 A RU 2017113026A RU 2734248 C2 RU2734248 C2 RU 2734248C2
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- Russia
- Prior art keywords
- substituted
- alkyl
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- mmol
- unsubstituted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 117
- 241000725643 Respiratory syncytial virus Species 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 208000015181 infectious disease Diseases 0.000 claims abstract description 10
- JOPCJJSYRPUEDS-UHFFFAOYSA-N 1'-[[5-(aminomethyl)-1-(4,4,4-trifluorobutyl)benzimidazol-2-yl]methyl]-6'-fluorospiro[cyclopropane-1,3'-indole]-2'-one Chemical compound NCC1=CC2=C(N(C(=N2)CN2C(C3(C4=CC=C(C=C24)F)CC3)=O)CCCC(F)(F)F)C=C1 JOPCJJSYRPUEDS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 4
- MPUMNDYDSTYPFD-UHFFFAOYSA-N [2-[(6-fluorospiro[2H-indole-3,1'-cyclopropane]-1-yl)methyl]-1-(oxan-4-yl)benzimidazol-5-yl]methanamine Chemical compound NCC1=CC2=C(N(C(=N2)CN2CC3(C4=CC=C(C=C24)F)CC3)C2CCOCC2)C=C1 MPUMNDYDSTYPFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 abstract 2
- UGTWLLBIEDUTMG-UHFFFAOYSA-N 1'-[[5-(aminomethyl)-1-(oxan-4-yl)benzimidazol-2-yl]methyl]-6'-fluorospiro[cyclopropane-1,3'-indole]-2'-one Chemical compound NCC1=CC2=C(N(C(=N2)CN2C(C3(C4=CC=C(C=C24)F)CC3)=O)C2CCOCC2)C=C1 UGTWLLBIEDUTMG-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
- 125000000217 alkyl group Chemical group 0.000 description 92
- 239000000243 solution Substances 0.000 description 71
- 125000001072 heteroaryl group Chemical group 0.000 description 70
- 125000000623 heterocyclic group Chemical group 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 229910052736 halogen Inorganic materials 0.000 description 56
- 150000002367 halogens Chemical class 0.000 description 56
- -1 2-methylbut-2-yl Chemical group 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 125000003118 aryl group Chemical group 0.000 description 43
- 235000019439 ethyl acetate Nutrition 0.000 description 42
- 239000000047 product Substances 0.000 description 41
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- 239000011541 reaction mixture Substances 0.000 description 39
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- 229910052799 carbon Inorganic materials 0.000 description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 125000000753 cycloalkyl group Chemical group 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- 125000004093 cyano group Chemical group *C#N 0.000 description 35
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
- 125000003545 alkoxy group Chemical group 0.000 description 29
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 29
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 27
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 22
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 22
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- 239000000725 suspension Substances 0.000 description 22
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- 125000000304 alkynyl group Chemical group 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 239000002609 medium Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 125000001153 fluoro group Chemical group F* 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
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- 206010061603 Respiratory syncytial virus infection Diseases 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- 102000004169 proteins and genes Human genes 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
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- 230000035699 permeability Effects 0.000 description 9
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- 241000700605 Viruses Species 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 description 8
- 239000013058 crude material Substances 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 7
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
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- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
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- BEHOIWZRCXJBLL-UHFFFAOYSA-N tert-butyl n-[[2-(chloromethyl)-1-(4,4,4-trifluorobutyl)benzimidazol-5-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C2N(CCCC(F)(F)F)C(CCl)=NC2=C1 BEHOIWZRCXJBLL-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000007485 viral shedding Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D471/02—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 two hetero rings
- C07D471/04—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
- A61K31/33—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
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D471/02—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 two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1417707.5 | 2014-10-07 | ||
| GBGB1417707.5A GB201417707D0 (en) | 2014-10-07 | 2014-10-07 | Pharmaceutical compounds |
| PCT/GB2015/052920 WO2016055780A1 (en) | 2014-10-07 | 2015-10-06 | Spiro-indolines for the treatment and prophylaxis of respiratory syncytial virus infection (rsv) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017113026A RU2017113026A (ru) | 2018-11-13 |
| RU2017113026A3 RU2017113026A3 (https=) | 2019-03-22 |
| RU2734248C2 true RU2734248C2 (ru) | 2020-10-13 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017113026A RU2734248C2 (ru) | 2014-10-07 | 2015-10-06 | Спироиндолиновые соединения для лечения и профилактики респираторно-синцитиального вируса (rsv) |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US10106539B2 (https=) |
| EP (1) | EP3204375B1 (https=) |
| JP (1) | JP6695334B2 (https=) |
| KR (2) | KR20230116097A (https=) |
| CN (1) | CN107108557B (https=) |
| AR (1) | AR102181A1 (https=) |
| AU (1) | AU2015329778B2 (https=) |
| BR (1) | BR112017007311B1 (https=) |
| CA (1) | CA2963740C (https=) |
| CL (1) | CL2017000839A1 (https=) |
| CO (1) | CO2017004603A2 (https=) |
| CY (1) | CY1121564T1 (https=) |
| DK (1) | DK3204375T3 (https=) |
| ES (1) | ES2718976T3 (https=) |
| GB (1) | GB201417707D0 (https=) |
| HR (1) | HRP20190808T1 (https=) |
| HU (1) | HUE043553T2 (https=) |
| LT (1) | LT3204375T (https=) |
| MX (1) | MX373233B (https=) |
| NZ (1) | NZ731323A (https=) |
| PE (1) | PE20170949A1 (https=) |
| PL (1) | PL3204375T3 (https=) |
| PT (1) | PT3204375T (https=) |
| RS (1) | RS58706B1 (https=) |
| RU (1) | RU2734248C2 (https=) |
| SG (1) | SG11201702766YA (https=) |
| SI (1) | SI3204375T1 (https=) |
| SM (1) | SMT201900249T1 (https=) |
| TR (1) | TR201903362T4 (https=) |
| TW (1) | TWI718107B (https=) |
| WO (1) | WO2016055780A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2853104C1 (ru) * | 2020-12-30 | 2025-12-18 | Цзянсу Хэнжуй Фармасьютикалз Ко., Лтд. | Азотсодержащее мостиковое гетероциклическое соединение, способ его получения и его применение в медицине |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2821649T3 (es) | 2015-06-08 | 2021-04-27 | Shangdong Danhong Pharmaceutical Co Ltd | Método para preparar derivados de imidazol e intermedios de los mismos y formas cristalinas |
| ES2878058T3 (es) * | 2016-08-04 | 2021-11-18 | Reviral Ltd | Derivados de pirimidina y su uso en el tratamiento y la prevención de una infección por virus respiratorio sincitial |
| GB201711704D0 (en) * | 2017-07-20 | 2017-09-06 | Reviral Ltd | Pharmaceutical compounds |
| GB201721812D0 (en) | 2017-12-22 | 2018-02-07 | Reviral Ltd | Pharmaceutical compounds |
| CN116077494A (zh) * | 2023-01-11 | 2023-05-09 | 黑龙江中医药大学 | 一种治疗呼吸道合胞病毒的药物组合物及其制备方法 |
| WO2024174953A1 (zh) * | 2023-02-21 | 2024-08-29 | 苏州隆博泰药业有限公司 | 苯并咪唑类衍生物及其医药用途 |
| WO2024252355A1 (en) | 2023-06-08 | 2024-12-12 | Pfizer Inc. | Pediatric dosing regimens comprising a fusion inhibitor for the treatment of rsv |
| WO2025120500A1 (en) | 2023-12-06 | 2025-06-12 | Pfizer Inc. | Benzodiazepine compounds as n-protein inhibitors |
| WO2025153942A1 (en) | 2024-01-16 | 2025-07-24 | Pfizer Inc. | Benzodiazepine pyrazolo carboxamides as n-protein inhibitors |
| WO2025248535A1 (en) * | 2024-05-29 | 2025-12-04 | Zydus Lifesciences Limited | Novel spirocyclic compounds to treat viral infections |
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| RU2184735C2 (ru) * | 1998-01-23 | 2002-07-10 | Санкио Компани, Лимитед | Производные спиропиперидина, лекарственное средство, способ профилактики или лечения |
| EA200200087A1 (ru) * | 1999-06-28 | 2002-08-29 | Янссен Фармацевтика Н.В. | Ингибиторы репликации респираторно-синцитиального вируса |
| WO2013068769A1 (en) * | 2011-11-10 | 2013-05-16 | Re:Viral Ltd | Pharmaceutical compounds |
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| JPS57102863A (en) * | 1980-12-16 | 1982-06-26 | Takeda Chem Ind Ltd | Spiroindolinone and its preparation |
| US6774134B2 (en) | 2000-12-20 | 2004-08-10 | Bristol-Myers Squibb Company | Heterocyclic substituted 2-methyl-benzimidazole antiviral agents |
| US6919331B2 (en) | 2001-12-10 | 2005-07-19 | Bristol-Myers Squibb Company | Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents |
| US7205328B2 (en) * | 2002-10-21 | 2007-04-17 | Irm Llc | Oxindoles with anti-HIV activity |
| JO2355B1 (en) | 2003-04-15 | 2006-12-12 | ميرك شارب اند دوم كوربوريشن | Hereditary calcitonin polypeptide receptor antagonists |
| US7390798B2 (en) | 2004-09-13 | 2008-06-24 | Merck & Co., Inc. | Carboxamide spirolactam CGRP receptor antagonists |
| BRPI0517418A (pt) | 2004-10-13 | 2008-10-07 | Merck & Co Inc | composto, composição farmacêutica, e, métodos para antagonismo de atividade do receptor de cgrp em um mamìfero, para tratar, controlar, melhorar ou reduzir o risco de dor de cabeça, enxaqueca ou cefalgia, e de tratamento ou prevenção de dores de cabeça de enxaqueca, cefalgias, e dores de cabeça |
| US20100278835A1 (en) | 2009-03-10 | 2010-11-04 | Astrazeneca Uk Limited | Novel compounds 660 |
| MY172021A (en) | 2012-10-16 | 2019-11-12 | Janssen Sciences Ireland Uc | Rsv antiviral compounds |
| EP2997028A1 (en) | 2013-05-14 | 2016-03-23 | F.Hoffmann-La Roche Ag | Aza-oxo-indoles for the treatment and prophylaxis of respiratory syncytial virus infection |
| KR20160007629A (ko) * | 2013-05-14 | 2016-01-20 | 에프. 호프만-라 로슈 아게 | 호흡기 세포융합 바이러스 감염의 치료 및 예방을 위한 아자-옥소-인돌 |
| CN105392787B (zh) * | 2013-05-14 | 2017-11-24 | 豪夫迈·罗氏有限公司 | 用于治疗和预防呼吸道合胞病毒感染的氮杂‑氧代‑吲哚 |
| KR20160030271A (ko) * | 2013-08-12 | 2016-03-16 | 에프. 호프만-라 로슈 아게 | 호흡기 세포융합 바이러스 감염의 치료 및 예방을 위한 아자-옥소-인돌 |
| CN105408330A (zh) * | 2013-08-12 | 2016-03-16 | 豪夫迈·罗氏有限公司 | 新的用于治疗和预防呼吸道合胞病毒感染的氮杂-氧代-吲哚 |
| JP6211195B2 (ja) * | 2013-08-12 | 2017-10-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 呼吸器合胞体ウイルス感染症の処置および予防のための新規アザ−オキソ−インドール |
| CN105431419A (zh) * | 2013-08-15 | 2016-03-23 | 豪夫迈·罗氏有限公司 | 新的用于治疗和预防呼吸道合胞病毒感染的氮杂-氧代-吲哚 |
| HK1222855A1 (zh) * | 2013-08-15 | 2017-07-14 | F. Hoffmann-La Roche Ag | 新的用於治疗和预防呼吸道合胞病毒感染的氮杂-氧代-吲哚 |
| KR20160030569A (ko) * | 2013-08-15 | 2016-03-18 | 에프. 호프만-라 로슈 아게 | 호흡기 세포융합 바이러스 감염의 치료 및 예방을 위한 신규한 아자-옥소-인돌 |
-
2014
- 2014-10-07 GB GBGB1417707.5A patent/GB201417707D0/en not_active Ceased
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2015
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- 2015-10-06 CN CN201580066385.4A patent/CN107108557B/zh active Active
- 2015-10-06 KR KR1020237025697A patent/KR20230116097A/ko active Pending
- 2015-10-06 BR BR112017007311-0A patent/BR112017007311B1/pt active IP Right Grant
- 2015-10-06 PE PE2017000576A patent/PE20170949A1/es unknown
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- 2015-10-06 RU RU2017113026A patent/RU2734248C2/ru active
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- 2015-10-06 DK DK15782033.3T patent/DK3204375T3/en active
- 2015-10-06 PT PT15782033T patent/PT3204375T/pt unknown
- 2015-10-06 AR ARP150103215A patent/AR102181A1/es not_active Application Discontinuation
- 2015-10-06 SI SI201530634T patent/SI3204375T1/sl unknown
- 2015-10-06 WO PCT/GB2015/052920 patent/WO2016055780A1/en not_active Ceased
- 2015-10-06 SM SM20190249T patent/SMT201900249T1/it unknown
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- 2015-10-06 HU HUE15782033A patent/HUE043553T2/hu unknown
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2017
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- 2017-05-05 CO CONC2017/0004603A patent/CO2017004603A2/es unknown
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2184735C2 (ru) * | 1998-01-23 | 2002-07-10 | Санкио Компани, Лимитед | Производные спиропиперидина, лекарственное средство, способ профилактики или лечения |
| EA200200087A1 (ru) * | 1999-06-28 | 2002-08-29 | Янссен Фармацевтика Н.В. | Ингибиторы репликации респираторно-синцитиального вируса |
| WO2013068769A1 (en) * | 2011-11-10 | 2013-05-16 | Re:Viral Ltd | Pharmaceutical compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2853104C1 (ru) * | 2020-12-30 | 2025-12-18 | Цзянсу Хэнжуй Фармасьютикалз Ко., Лтд. | Азотсодержащее мостиковое гетероциклическое соединение, способ его получения и его применение в медицине |
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