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DK2997011T3 - Sulfamoylpyrrolamidderivater og anvendelse deraf som medikamenter til behandling af hepatitis b - Google Patents

Sulfamoylpyrrolamidderivater og anvendelse deraf som medikamenter til behandling af hepatitis b Download PDF

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Publication number
DK2997011T3
DK2997011T3 DK14727752.9T DK14727752T DK2997011T3 DK 2997011 T3 DK2997011 T3 DK 2997011T3 DK 14727752 T DK14727752 T DK 14727752T DK 2997011 T3 DK2997011 T3 DK 2997011T3
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compound
methyl
mmol
fluoro
pyrrole
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DK14727752.9T
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Inventor
Koen Vandyck
Geerwin Yvonne Paul Haché
Stefaan Julien Last
Gowan David Craig Mc
Wim Gaston Verschueren
Pierre Jean-Marie Bernard Raboisson
Geert Rombouts
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Janssen Sciences Ireland Uc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
    • 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
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicinal Preparation (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (35)

1. Forbindelse med formel (ID)
eller en stereoisomer eller en tautomer form deraf, hvor: hver X uafhængigt er CR7; Ra, Rb og Rc er valgt uafhængigt fra gruppen, der består af hydrogen, fluor, brom, chlor, -CHF2, -CF2-methyl, -CH2F, -CF3, -OCF3, -CN, Ci-C3alkyl og C3-C4cycloalkyl; Rd er hydrogen eller fluor; R4 er hydrogen, Ci-C3alkyl eller C3-C4cycloalkyl; R5 er hydrogen; R6 er valgt fra gruppen, der består af C2~C6alkyl, Ci-C4alkyl-R8, der eventuelt er substitueret med et eller flere fluor, Ci-C4alkyl-R9, der eventuelt er substitueret med et eller flere fluor, og en 3-7-leddet mono- eller polycyklisk, mættet ring, der eventuelt indeholder er eller flere heteroatomer, der hver er valgt uafhængigt fra gruppen, der består af 0, S og N, hvor den 3-7-leddede, mættede ring eller C2-C6alkyl eventuelt er substitueret med en eller flere substituenter, der hver er valgt uafhængigt fra gruppen, der består af hydrogen, -OH, fluor, oxo, R9, R10 og Ci-C4alkyl, der eventuelt er substitueret med R10; R7 er hydrogen, -CN, fluor, chlor, brom, -CHF2, -CF2-methyl, -CH2F, -CF3, Ci-C3alkyl, der eventuelt er substitueret med methoxy, C2-C3alkenyl eller C3-C4cycloalkyl; R8 er en 3-7-leddet, mættet ring, der eventuelt indeholder et eller flere heteroatomer, der hver er valgt uafhængigt fra gruppen, der består af 0, S og N, hvor den 3-7-leddede, mættede ring eventuelt er substitueret med en eller flere Ci-C4alkyl, der eventuelt er substitueret med R10; R9 er, Ci-C4alkyloxy, -S02-methyl, -C (=0)-OR11 eller -C (=0)-N (R11)2; R10 er -CN, -OH, fluor, -CHF2, -CH2F eller -CF3; R11 er hydrogen eller Ci-C3alkyl;
eller et farmaceutisk acceptabelt salt eller et solvat deraf, hvor forbindelsen ikke er
2. Forbindelse ifølge krav 1 med formel (IB)
3. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor R4 er methyl.
4. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor R6 indeholder en 3-7-leddet, mættet ring, der eventuelt indeholder ét oxygen.
5. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor R6 er en 4 eller 5-leddet, mættet ring, der indeholder ét oxygen, hvor den 4 eller 5-leddede, mættede ring eventuelt er substitueret med Ci-C4alkyl, der eventuelt er substitueret med R10.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, hvor R6 omfatter en forgrenet C3-C6alkyl, der eventuelt er substitueret med et eller flere fluor, eller hvor R6 omfatter en C3-C6cycloalkyl, hvor C3-C6cycloalkyl er substitueret med et eller flere fluor eller substitueret med Ci-C4alkyl, der er substitueret med et eller flere fluor, eller hvor R6 omfatter en C3-C6cycloalkyl, der eventuelt er substitueret med et eller flere fluor og/eller substitueret med Ci-C4alkyl, der eventuelt er substitueret med et eller flere fluor.
7. Forbindelse ifølge krav 6, hvor R6 er en forgrenet C3-Csalkyl, der er substitueret med et eller flere fluor.
8. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor Rb er hydrogen eller fluor.
9. Forbindelse ifølge et hvilket som helst af ovennævnte krav, hvor Ra og Rc er valgt uafhængigt fra gruppen, der består af hydrogen, fluor, chlor, CN og methyl.
10. Forbindelse ifølge krav 1 med formel (IC)
eller en stereoisomer eller en tautomer form deraf, hvor: X er CR7; Ra, Rb og Rc er valgt uafhængigt fra gruppen, der består af hydrogen, fluor, brom, chlor, -CHF2, -CF2-methyl, -CH2F, -CF3, -OCF3, -CN, Ci-C3alkyl og C3-C4cycloalkyl; R4 er hydrogen, Ci-C3alkyl eller C3-C4cycloalkyl; R5 er hydrogen; R6 er valgt fra gruppen, der består af C2-C6alkyl, Ci-C4alkyl-R8, der eventuelt er substitueret med et eller flere fluor, Ci-C4alkyl-R9, der eventuelt er substitueret med et eller flere fluor, og en 3-7-leddet mono- eller polycyklisk, mættet ring, der eventuelt indeholder et eller flere heteroatomer, der hver er valgt uafhængigt fra gruppen, der består af O, S og N, hvor den 3-7-leddede, mættede ring eller C2-C6alkyl eventuelt er substitueret med en eller flere substituenter, der hver er valgt uafhængigt fra gruppen, der består af hydrogen, -OH, fluor, oxo, R9, R10 og Ci-C4alkyl, der eventuelt er substitueret med R10; R7 er hydrogen, -CN, fluor, chlor, brom, -CHF2, -CF2-methyl, -CH2F, -CF3, Ci-C3alkyl eller C3-C4cycloalkyl; R8 er en 3-7-leddet, mættet ring, der eventuelt indeholder et eller flere heteroatomer, der hver er valgt uafhængigt fra gruppen, der består af O, S og N, hvor den 3-7-leddede, mættede ring eventuelt er substitueret med en eller flere Ci-C4alkyl, der eventuelt er substitueret med R10;
R9 er, Ci-C4alkyloxy, -SO2-methyl, -C (=0) -OR11 eller -C (=0)-N(R)2; R10 er -CN, -OH, fluor, -CHF2, -CH2F eller -CF3; R11 er hydrogen eller Ci-C3alkyl; eller et farmaceutisk acceptabelt salt eller et solvat deraf, hvor forbindelsen ikke er
11. Forbindelse ifølge krav 10, hvor R4 er Ci-C3alkyl; R6 er valgt fra gruppen, der består af C2-C6alkyl, der eventuelt er substitueret med et eller flere fluor; og R7 er hydrogen, fluor, chlor eller Ci-C3alkyl.
12. Forbindelse ifølge krav 10 eller 11, hvor R4 er methyl, R6 er C2-C6alkyl, der er substitueret med et eller flere fluor, R7 er hydrogen, og Ra, Rb og Rc er valgt uafhængigt fra gruppen, der består af hydrogen, fluor, chlor, methyl og -CN.
13. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
14. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
15. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
16. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
17. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
18. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
19. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
20. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
21. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
22. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
23. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
24. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
25. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
26. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
27. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
28. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
29. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
30. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
31. Forbindelse ifølge krav 1, hvor forbindelsen er
eller et farmaceutisk acceptabelt salt eller et solvat deraf.
32. Forbindelse ifølge et hvilket som helst af kravene 1 til 31 til anvendelse som et medikament.
33. Forbindelse ifølge et hvilket som helst af kravene 1 til 31 til anvendelse til forebyggelse eller behandling af en HBV-infektion hos et pattedyr.
34. Farmaceutisk sammensætning, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1 til 31 og et farmaceutisk acceptabelt bæremateriale.
35. Produkt, der indeholder (a) en forbindelse med formel (ID) ifølge et hvilket som helst af kravene 1 til 31 og (b) en anden HBV-inhibitor som et kombineret præparat til samtidig, separat eller sekventiel anvendelse til behandling af HBV-infektioner.
DK14727752.9T 2013-05-17 2014-05-16 Sulfamoylpyrrolamidderivater og anvendelse deraf som medikamenter til behandling af hepatitis b DK2997011T3 (da)

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EP13168291 2013-05-17
EP13175181 2013-07-04
EP13182281 2013-08-29
EP13191209 2013-10-31
EP13198160 2013-12-18
EP14157900 2014-03-05
PCT/EP2014/060102 WO2014184350A1 (en) 2013-05-17 2014-05-16 Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b

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US (3) US9884818B2 (da)
EP (3) EP2997011B1 (da)
JP (3) JP6318238B2 (da)
KR (4) KR20210025712A (da)
CN (2) CN110003076A (da)
AU (4) AU2014267220B2 (da)
BR (1) BR112015028461A2 (da)
CA (1) CA2909348C (da)
CL (1) CL2015003370A1 (da)
CY (2) CY1121391T1 (da)
DK (2) DK2997011T3 (da)
EA (1) EA037378B1 (da)
EC (1) ECSP15048122A (da)
ES (2) ES2787704T3 (da)
GT (1) GT201500312A (da)
HR (2) HRP20181544T1 (da)
HU (2) HUE050236T2 (da)
IL (2) IL260597B (da)
JO (2) JO3603B1 (da)
LT (2) LT2997011T (da)
ME (1) ME03787B (da)
MX (3) MX387255B (da)
NI (1) NI201500161A (da)
PH (2) PH12015502579B1 (da)
PL (2) PL2997011T3 (da)
PT (2) PT3121164T (da)
RS (2) RS58140B1 (da)
SG (4) SG11201509428PA (da)
SI (2) SI2997011T1 (da)
SM (2) SMT201800610T1 (da)
TW (4) TW202126620A (da)
UA (1) UA117246C2 (da)
UY (1) UY35573A (da)
WO (1) WO2014184350A1 (da)
ZA (1) ZA201508443B (da)

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