DK3204375T3 - Spiro-indoliner til behandling og profylakse af respiratorisk syncytialvirusinfektion (RSV) - Google Patents

Spiro-indoliner til behandling og profylakse af respiratorisk syncytialvirusinfektion (RSV) Download PDF

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DK3204375T3
DK3204375T3 DK15782033.3T DK15782033T DK3204375T3 DK 3204375 T3 DK3204375 T3 DK 3204375T3 DK 15782033 T DK15782033 T DK 15782033T DK 3204375 T3 DK3204375 T3 DK 3204375T3
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substituted
compound
alkyl
unsubstituted
methyl
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DK15782033.3T
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Graham Lunn
Michael Paradowski
Simorte Jose Miguel Gascon
Stuart Cockerill
Neil Mathews
Simon Ward
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Reviral Ltd
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    • 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
    • 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
    • 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
    • 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

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  • 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)

Claims (15)

1. Forbindelse, der er en benzimidazol med formlen (I):
hvor: - én af X og Y er et N-atom eller et substitueret C-atom, og den anden er CH; - L er en enkeltbinding eller Ci-3-alkylen; - R1 er Ci-e-alkyl, C2-e-alkenyl, C2-e-alkynyl, 3- til 10-leddet cycloalkyl, 5- til 10-leddet heterocyclyl eller 5- til 12-leddet heteroaryl, der hver er usubstitueret eller substitueret; -Zer-N(R2)2; - hver R2 uafhængigt er hydrogen, Ci-e-alkyl, C2-e-alkenyl eller C2-e-alkynyl, hvor alkyl-, alkenyl- og alkynylgrupperne er usubstituerede eller substitueretde og - m er 1; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor én af X og Y er et N-atom eller et C-atom substitueret med et halogenatom, og den anden er CH.
3. Forbindelse ifølge krav 1, hvor L er en enkeltbinding eller Ci-alkylen.
4. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor R1 er C3-e-alkyl, C3-e-alkenyl, 5- eller 6-leddet cycloalkyl, 5- eller 6-leddet heterocyclyl eller 5- eller 6-leddet heteroaryl, der hver er usubstitueret eller substitueret.
5. Forbindelse ifølge krav 4, hvor R1 er Cs-e-alkyl, der er usubstitueret eller substitueret med et, to, tre eller fire halogenatomer, R1 er 6-leddet cycloalkyl
substitueret med en, to, tre eller fire -OH grupper, eller R1 er usubstitueret 6-leddet heterocyclyl.
6. Forbindelse ifølge krav 1, hvor Z er NH2.
7. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor hver R2 uafhængigt er hydrogen eller Ci-4-alkyl.
8. Forbindelse ifølge krav 1, hvor, i formlen (I): - én af X og Y er et N-atom eller C substitueret med et fluoratom, og den anden er CH; - R1 er C5-6-alkyl, der er usubstitueret eller substitueret med ét, to, tre eller fire fluoratomer, R1 er cyclohexyl, der er usubstitueret eller substitueret med én eller to -OH-grupper, eller R1 er usubstitueret tetrahydropyan; - m er 1 - L er en enkeltbinding eller Ci-alkylen og -ZerNH2.
9. Forbindelse ifølge krav 1, der er udvalgt fra: - 1 ’-{[5-(aminomethyl)-1 -(4,4,4-trif I uo rbutyl)-1H-1,3-benzodiazol-2-yl]methyl}-6’-fluoro-1 ’,2’-dihydrospiro[cyclopropan-1,3’-i ndol]-2’-on; - 1 ’-((5-(aminomethyl)-1 -(4,4,4-trif I uo rbutyl)-1 H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropan-1,3’-pyrrolo[2,3-b]pyridin]-2’(TH)-on; - 1 ’-((5-(aminomethyl)-1 -isopentyl-1 H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropan-1,3’-pyrrolo[2,3-b]pyridin]-2’(TH)-on; - 1 ’-((5-(aminomethyl)-1 -isopentyl-1 H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropan-1,3’-pyrrolo[2,3-c]pyridin]-2’(1 Ή)-οη og - 1 ’-((5-(aminomethyl)-1 -(tetrahydro-2H-pyran-4-yl)-1 H-benzo[d]imidazol-2-yl)methyl)-6’-fluorspiro[cyclopropan-1,3’-indolin]-2’-on; - 1 ’-((5-(aminomethyl)-1 -((1 R,4R)-4-hydroxycyclohexyl)-1 H-benzo[d]imidazol-2-yl)methyl)-6’-fluorspiro[cyclopropan-1,3’-indolin]-2’-on og de farmaceutisk acceptable salte deraf.
10. Farmaceutisk sammensætning, der omfatter en forbindelse som defineret i et hvilket som helst af krav 1 til 9 og en farmaceutisk acceptabel bærer eller fortynder.
11. Forbindelse som defineret i et hvilket som helst af krav 1 til 9 til anvendelse i behandling af menneske- eller dyrekroppen ved terapi.
12. Forbindelse som defineret i et hvilket som helst af krav 1 til 9 til anvendelse i behandling eller forebyggelse af en RSV-infektion.
13. Produkt, der indeholder: (a) en forbindelse som defineret i et hvilket som helst af krav 1 til 9; og (b) et eller flere yderligere terapeutiske midler; til samtidig, separat eller sekventiel anvendelse i behandling af et individ, der lider af eller er modtagelig for en RSV-infektion.
14. Produkt til anvendelse ifølge krav 13, hvor det yderligere terapeutiske middel er: (i) en RSV nucleokapsid(N)-proteinhæmmer; (ii) en anden proteinhæmmer, såsom én der hæmmer phosphoprotein- (P) proteinet og/eller det store (L) protein; (iii) et anti-RSV-monoklonalt antistof, såsom et F-proteinantistof; (iv) en immunmodulerende toll-lignende receptorforbindelse; (v) et andet antiviralt respiratorisk virus, såsom en anti-influenza- og/eller anti-rhinovirus-forbindelse og/eller (vi) en antiinflammatorisk forbindelse.
15. Farmaceutisk sammensætning, der omfatter (a) en forbindelse som defineret i et hvilket som helst af krav 1 til 9, og (b) et eller flere yderligere terapeutiske midler, som defineret i krav 14, sammen med en farmaceutisk acceptabel bærer eller fortynder.
DK15782033.3T 2014-10-07 2015-10-06 Spiro-indoliner til behandling og profylakse af respiratorisk syncytialvirusinfektion (RSV) DK3204375T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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)

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US (1) US10106539B2 (da)
EP (1) EP3204375B1 (da)
JP (1) JP6695334B2 (da)
KR (2) KR20230116097A (da)
CN (1) CN107108557B (da)
AR (1) AR102181A1 (da)
AU (1) AU2015329778B2 (da)
BR (1) BR112017007311B1 (da)
CA (1) CA2963740C (da)
CL (1) CL2017000839A1 (da)
CO (1) CO2017004603A2 (da)
CY (1) CY1121564T1 (da)
DK (1) DK3204375T3 (da)
ES (1) ES2718976T3 (da)
GB (1) GB201417707D0 (da)
HR (1) HRP20190808T1 (da)
HU (1) HUE043553T2 (da)
LT (1) LT3204375T (da)
MX (1) MX373233B (da)
NZ (1) NZ731323A (da)
PE (1) PE20170949A1 (da)
PL (1) PL3204375T3 (da)
PT (1) PT3204375T (da)
RS (1) RS58706B1 (da)
RU (1) RU2734248C2 (da)
SG (1) SG11201702766YA (da)
SI (1) SI3204375T1 (da)
SM (1) SMT201900249T1 (da)
TR (1) TR201903362T4 (da)
TW (1) TWI718107B (da)
WO (1) WO2016055780A1 (da)

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HRP20190808T1 (hr) 2019-08-23
RS58706B1 (sr) 2019-06-28
HUE043553T2 (hu) 2019-09-30
SG11201702766YA (en) 2017-05-30
TW201625583A (zh) 2016-07-16
MX373233B (es) 2020-05-08
BR112017007311B1 (pt) 2022-11-22
TWI718107B (zh) 2021-02-11
NZ731323A (en) 2022-09-30
GB201417707D0 (en) 2014-11-19
AU2015329778A1 (en) 2017-05-04
AU2015329778A8 (en) 2017-05-18
CA2963740A1 (en) 2016-04-14
RU2017113026A3 (da) 2019-03-22
PL3204375T3 (pl) 2019-06-28
AR102181A1 (es) 2017-02-08
ES2718976T3 (es) 2019-07-05
PE20170949A1 (es) 2017-07-13
CN107108557A (zh) 2017-08-29
KR102561796B1 (ko) 2023-07-31
PT3204375T (pt) 2019-04-01
AU2015329778B2 (en) 2020-04-23
SMT201900249T1 (it) 2019-07-11
CN107108557B (zh) 2020-11-10
KR20230116097A (ko) 2023-08-03
JP2017530992A (ja) 2017-10-19
CL2017000839A1 (es) 2017-10-13
WO2016055780A1 (en) 2016-04-14
RU2017113026A (ru) 2018-11-13
JP6695334B2 (ja) 2020-05-20
CA2963740C (en) 2022-11-29
US20170305908A1 (en) 2017-10-26
EP3204375A1 (en) 2017-08-16
CO2017004603A2 (es) 2017-10-31
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US10106539B2 (en) 2018-10-23
EP3204375B1 (en) 2019-02-13
RU2734248C2 (ru) 2020-10-13
LT3204375T (lt) 2019-05-10
BR112017007311A2 (pt) 2017-12-19
KR20170066577A (ko) 2017-06-14
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SI3204375T1 (sl) 2019-05-31
MX2017004425A (es) 2017-10-11

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