DK2501693T3 - Aza-heterocykliske akrylamider og anvendelse deraf som baktericider - Google Patents

Aza-heterocykliske akrylamider og anvendelse deraf som baktericider Download PDF

Info

Publication number
DK2501693T3
DK2501693T3 DK10776385.6T DK10776385T DK2501693T3 DK 2501693 T3 DK2501693 T3 DK 2501693T3 DK 10776385 T DK10776385 T DK 10776385T DK 2501693 T3 DK2501693 T3 DK 2501693T3
Authority
DK
Denmark
Prior art keywords
naphthyridin
dihydro
mmol
azetidin
oxo
Prior art date
Application number
DK10776385.6T
Other languages
English (en)
Inventor
Vincent Gerusz
Sonia Escaich
Mayalen Oxoby
Alexis Denis
Original Assignee
Fab Pharma Sas
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fab Pharma Sas filed Critical Fab Pharma Sas
Application granted granted Critical
Publication of DK2501693T3 publication Critical patent/DK2501693T3/da

Links

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
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
    • 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
    • A61K31/4375—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 six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • 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
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 no 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D471/20—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Pulmonology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (17)

1. Forbindelse, som er en forbindelse med formlen (I):
(I) hvor: - W og X uafhængigt står for en binding eller en -(CH2)i-4-gruppe, således at W og X tilsammen indeholder 1-5 carbonatomer; - RI står for en H, F, CN, (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, C02Rd, CORd, CONRaRb, OCORd, ORd, NRaRb, ON=CRdRe, NRcCORd, NRcCOORd, OCONRaRb, NRcCONRaRb, NRcS02Ra, S(0)nRa, S02NRaRb, -C(Ra) = N-0-Rf, Y-Ar eller en Z-Het-gruppe, hvor Ar står for phenyl eller naphthyl, Het står for en 4-10-leddet monocyklisk eller bicyklisk mættet eller umættet heterocyklisk gruppe indeholdende 1-5 heteroatomer udvalgt blandt N, O og S, og Y og Z uafhængigt står for en binding eller en forbindelsesgruppe udvalgt blandt O, S, CO, (Ci-C6)-alkylen, -0-(Ci-C6)-alkylen, -CO-(Ci-C6)-alkylen eller -ON=CRd-(Ci-C6)-alkylen, hvor nævnte Rl-gruppe eventuelt kan være substitueret med en eller flere R4-grupper; - R2 står for en H, F, CN, (Ci-C5)-alkyl, (C2-C6)-alkenyl, (C2-C5)-alkynyl, C02Rd, CORd, CONRaRb, OCORd, ORd, NRaRb, ON=CRdRe, NRcCORd, NRcCOORd, OCONRaRb, NRcCONRaRb, NRcS02Ra, S(0)nRa eller S02NRaRb-gruppe; - Ra, Rb og Rc uafhængigt står for H, (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C5)-alkynyl, eller en NRaRb-gruppe kan eventuelt danne en 3- til 7-leddet nitrogenholdig mættet heterocyklisk gruppe eventuelt indeholdende 1 til 3 yderligere heteroatomer udvalgt blandt N, O eller S, hvor nævnte heterocykliske gruppe eventuelt kan være substitueret med en eller flere (Ci-C5)-alkyl-grupper; - Rd og Re uafhængigt står for H, (Ci-C5)-alkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl, halo(Ci-C6)-alkyl, halo(Ci-C5)-alkyl-0-(Ci-C6)-alkyl- eller (Ci-C5)-alkyl-0-(Ci-C5)-alkyl-; - Rf står for (Ci-C6)-alkyl, (C2-C6)-alkenyl, (C2-C5)-alkynyl, halo(Ci-C5)-alkyl eller -(Ci-C5)-alkyl-Ar, hvor Ar står for phenyl eller naphthyl; - R4 står for halogen, CN, (Ci-C5)-alkyl, (C2-C6)-alkenyl, (C2-Cg)-alkynyl, C02Rd, CORd, CONRaRb, OCORd, ORd, NRaRb, ON=CRdRe, NRcCORd, NRcCOORd, OCONRaRb, NRcCONRaRb, NRcS02Ra S(0)nRa, eller S02NRaRb; - n står for et heltal udvalgt blandt 0 til 2; - R3 er en pyridylring, der eventuelt er kondenseret med en 5, 6 eller 7-leddet heterocyklisk gruppe indeholdende 1-3 heteroatomer udvalgt blandt N, O og S, hvor nævnte heterocyklisk gruppe er aromatisk, delvis aromatisk eller mættet, og hvor nævnte R3-qruppe eventuelt kan være substitueret med en eller flere R5-grupper; - R5 er udvalgt fra gruppen bestående af F, C02Rd, CORd, CONRaRb, 0Rd, =0, NRaRb, NRcC0Rd eller (Ci-C6)-alkyl eventuelt substitueret med F, C02Rd, C0NRaRb, 0Rd, NRaRb, NRaC0Rd eller Flet eventuelt substitueret med en eller flere (Ci-C6)-alkyl-grupper, eller to R5-grupper kan sammen med atomet, hvortil de er forbundne, danne en Flet-gruppe, som eventuelt kan være substitueret med en eller flere (Ci-C6)-alkyl-grupper; eller et farmaceutisk acceptabelt salt eller solvat deraf, med det forbehold, at forbindelsen ikke er 3-[6-(benzoe[b]thiophen-2-yl)-pyridin-2-yl]-l-(piperidin-l-yl)-propenontrifluoreddikesyresalt eller 3-(6-benzoe[b]thiophen-2-yl)-pyridin-3-yl)-l-(piperidin-l-yl)propenon.
2. Forbindelse som defineret i krav 1, hvor W og X begge står for CFI2.
3. Forbindelse som defineret i krav 1 eller krav 2, hvor RI står for en FI, F, (Ci-C6)-alkyl, (C2-C6)-alkenyl, 0Rd, S(0)nRa, -C(Ra)=N-0-Rf, Y-Ar eller Z-Flet-gruppe, som hver især eventuelt kan være substitueret med en eller flere R4-grupper.
4. Forbindelse som defineret i krav 3, hvor RI står for 0Rd, Z-Flet eller -C(Ra)=N-0-Rf.
5. Forbindelse som defineret i et hvilket som helst af de foregående krav, hvor R2 står for en Fl eller ORd-gruppe.
6. Forbindelse som defineret i et hvilket som helst af de foregående krav, hvor R4 står for halogen, (Ci-C6)-alkyl, (C2-C6)-alkenyl eller (C2-C6)-alkynyl.
7. Forbindelse som defineret i et hvilket som helst af de foregående krav, hvor R3 står for en heterocyklisk gruppe med formlen (a), (b), (c), (d), (f), (i), (j) eller (k):
(j) (k) som hver især eventuelt kan være substitueret med en eller flere R5-grupper.
8. Forbindelse som defineret i krav 7, hvor R3 står for en heterocyklisk gruppe med
(a) (j) som hver især eventuelt kan være substitueret, eller i påkommende tilfælde yderligere substitueret, med en eller flere R5-grupper.
9. Forbindelse med formlen (I) som defineret i krav 1, som er: 6-[((lE)-3-azetidin-l-yl-3-oxoprop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (El); 6-[((lE)-3-oxo-3-pyrrolidin-l-ylprop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E2); 6-[((lE)-3-oxo-3-piperidin-l-ylprop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E3); 6-{((lE)-3-[4-(2-hydroxyethyl)piperidin-l-yl]-3-oxoprop-l-en-l-yl}-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E4); 6-[((lE)-3-{[4-(4-fluorphenoxy)methyl]piperidin-l-yl}-3-oxoprop-l-en-l-yl]-3,4-dihydro- 1.8- naphthyridin-2(lH)-on (E5); 6-[((lE)-3-oxo-3-(3-phenoxyazetidin-l-yl)prop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E6); 6-[((lE)-3-oxo-3-(2-phenylpyrrolidin-l-yl)prop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E7); 6-[((lE)-3-oxo-3-(4-propylpiperidin-l-yl)prop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E8); 6-[((lE)-3-{[3-(4-fluorphenoxy)methyl]piperidin-l-yl}-3-oxoprop-l-en-l-yl]-3,4-dihydro- 1.8- naphthyridin-2(lH)-on (E9); 6-[((lE)-3-oxo-3-(3-phenoxypyrrolidin-l-yl)prop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E10); 6-{((lE)-3-[3-(5-methyl-l,2,4-oxadiazol-3-yl)azetidin-l-yl]-3-oxoprop-l-en-l-yl}-3,4-dihydro-l,8-naphthyridin-2(lH)-on (Eli); 6-{((lE)-3-oxo-3-[3-(2-thienylmethoxy)azetidin-l-yl]prop-l-en-l-yl}-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E12); 6-{((lE)-3-[2-(5-methyl-l,2,4-oxadiazol-3-yl)piperidin-l-yl]-3-oxoprop-l-en-l-yl>-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E13); 6-{((lE)-3-[4-hydroxy-4-phenylpiperidin-l-yl]-3-oxoprop-l-en-l-yl}-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E14); 6-{((lE)-3-oxo-3-[3-(pentyloxy)azetidin-l-yl]prop-l-en-l-yl}-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E15); A_/( (1 Π- ^ rw/rirlin-'^-x/lrivv/'^nv/rmliHin-l -\/l Ί nrnn-1 .en.1 _\/l\_"3 A-A i h\/Hrn_ 1 Q_ naphthyridin-2(lH)-on (E16); 6-{((lE)-3-[3-(benzyloxy)azetidin-l-yl]-3-oxoprop-l-en-l-yl>-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E17); 6-{((lE)-3-[2-(l,3-benzoxazol-2-yl)piperidin-l-yl]-3-oxoprop-l-en-l-yl>-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E18); 6-[((lE)-3-{3-[(2-methylprop-2-en-l-yl)oxy]azetidin-l-yl}-3-oxoprop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E19); 6-{((lE)-3-oxo-3-[3-(l,3-thiazol-2-ylmethoxy)azetidin-l-yl]prop-l-en-l-yl>-3,4-dihydro- l,8-naphthyridin-2(lH)-on (E20); 6-{((lE)-3-[3-({[(lE)-l-methyl-2-pyrimidin-2-ylethyliden]amino}oxy)azetidin-l-yl]-3-oxoprop-l-en-l-yl>-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E21); 6-{((lE)-3-[3-(pentylsulfonyl)azetidin-l-yl]-3-oxoprop-l-en-l-yl>-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E22); 5- {((lE)-3-oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-l-yl]prop-l-en-l-yl>pyridin-2-amin (E23); N-(5-{(lE)-3-oxo-3-[3-(pyridin-4-ylmethoxy)azetidin-l-yl]prop-l-en-l-yl>pyridin-2-yl)acetamid (E24); methyl-6-[(lE)-3-{4-[(4-fluorphenoxy)methyl]piperidin-l-yl>-3-oxoprop-l-en-l-yl]-2-oxo-l,2,3,4-tetrahydro-l,8-naphthyridin-3-carboxylat (E25); 6- [((lE)-3-{4-[(4-fluorphenoxy)methyl]piperidin-l-yl}-3-oxoprop-l-en-l-yl]-2-oxo-l,2,3,4-tetrahydro-l,8-naphthyridin-3-carboxamid (E26); 6-[((lE)-3-{4-[(4-fluorphenoxy)methyl]pipendin-l-yl}-3-oxoprop-l-en-l-yl]-2-oxo-l,2-dihydro-l,8-naphthyridiri-3-carboxamid (E27); 3-((hydroxymethyl)-6-[(lE)-3-{4-[(4-fluorphenoxy)methyl]pipendin-l-yl>-3-oxoprop-l-en-l-yl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E28); (E)-6-(3-oxo-3-(3-(2-(thiophen-2-yl)ethoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E29); (E)-6-(3-oxo-3-(3-(3-(thiophen-2-yl)propoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E30); (E)-6-(3-(3-((3-methylthiophen-2-yl)methoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E31); 6-[3-(3-(4-methyl-thiophen-2ylmethoxy)-azetidin-l-yl)-3-oxo-propenyl]-3,4-dihydro-l/-/-[l,8]naphthyridin-2-on (E32); (f)-6-(3-(3-((5-methylthiophen-2-yl)methoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E33); (f)-6-[3-(2-methoxyethoxy)azetidin-l-yl)-3-oxoprop-l-enyl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E34); (E)-6-[3-(3-methoxypropoxy)azetidin-l-yl)-3-oxoprop-l-enyl]-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E35); (E)-6-[3-(3-butoxyazetidin-l-yl)-3-oxoprop-l-enyll-3,4-dihydro-l,8-naphthyridin-2(lH)- on (E36); (f)-6-[3-(3-isobutoxyazetidin-l-yl)-3-oxoprop-l-enyl]-3,4-dihydro-l,8-naphthyridin-2(lW)-on (E37); (£)-6-(3-(3-(( l-methyl-lH-pyrazol-3-yl)methoxy)azet:idin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lW)-on (E38); (E)-6-(3-oxo-3-(3-(thiazol-5-ylmethoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E39); (£)-6-(3-(3-(furan-2-ylmethoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E40); (E)-l'-methyl-6-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-l-enyl)-l/V-spiro[[l,8]naphthyridin-3,4'-piperidin]-2(41-1)-on (E41); (£)-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-l-enyl)-4,5-dihydro-lH-pyrido[2,3-e][l,4]diazepin-2(3W)-on (E42); (£)-ethyl-2-(2-oxo-6-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-l-enyl)-l,2-dihydropyndo[2,3-d]pynmidin-3(4W)-yl)acetat (E43); (E)-3-(2-(4-methylpiperazin-l-yl)ethyl)-6-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(l/-/)-on (E44); (E)-3-(3-((dimethylamino)methyl)-lH-pyrrolo[2,3-b]pyndin-5-yl)-l-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-2-en-l-on (E45); (£)-6-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-l-yl)prop-l-enyl)-lf/-imidazo[4,5-b]pyridin-2(3/-/)-on (E46); (£)-6-(3-oxo-3-(3-(3,3,3-trifluorpropoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lAY)-on (E47); (E)-6-(3-oxo-3-(3-(4,4,4-trifluorbutoxy)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lW)-on (E48); 6-(((E)-3-(3-((£)-but-2-enyloxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E49); 6-(((E)-3-(3-((Z)-but-2-enyloxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E50); 6-(((£)-3-(3-((£)-2-methylbut-2-enyloxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro- 1.8- naphthyridin-2(l/-/)-on (E51); (£)-6-(3-(3-(benzoe[b]thiophen-2-ylmethoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E52); (£)-6-(3-(3-((4-bromothiophen-2-yl)methoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E53); (E)-6-(3-(3-((4-chlorothiophen-2-yl)methoxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E54); 6-(((£)-3-oxo-3-(3-((Z)-l-(propoxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-3,4-dihydro- 1.8- naphthyridin-2(l/Y)-on (E55); 6-(((£)-3-oxo-3-(3-((Z)-l-(2,2,2-trifluorethoxyimino) ethyl)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E56); 6-(((£)-3-(3-((Z)-l-(ethoxyimino)ethyl)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E57); (£)-6-(3-(3-(benzoefuran-3-yl)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E58); (E)-6-(3-(3-(benzoefuran-2-yl)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E59); (E)-6-(3-(3-(benzoefuran-7-yloxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E60); (f)-6-(3-(3-(benzoe[b]thiophen-3-yloxy)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E61); (£)-6-(3-oxo-3-(3-(thiophen-2-ylthio)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(l/-/)-on (E62); (E)-6-(3-(3-butoxyazetidin-l-yl)-3-oxoprop-l-enyl)-l'-methyl-lW-spiro[[l,8]naphthyndin-3,4'-pipendin]-2(4/7)-on (E63); l'-methyl-6-((E)-3-oxo-3-(3-((E)-l-(benzyloxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-l/-/-spiro[[l,8]naphthyridin-3,4'-piperidin]-2(4/-/)-on (E64); l'-methyl-6-((E)-3-oxo-3-(3-((E)-l-(propoxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-lH-spiro[[l,8]naphthyridin-3,4'-piperidin]-2(4/-/)-on (E65); (E)-l'-methyl-6-(3-oxo-3-(3-(2-(thiophen-2-yl)ethoxy)azetidin-l-yl)prop-l-en-l-yl)-lH-spiro[[l,8]naphthyridin-3,4'-piperidin]-2(4H)-on (E66); (E)-6-(3-(3-(3-methylbenzofuran-2-yl)azetidin-l-yl)-3-oxoprop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E67); (E)-l'-methyl-6-(3-(3-(3-methylbenzofuran-2-yl)azetidin-l-yl)-3-oxoprop-l-enyl)-lH-spiro[[l,8]naphthyndin-3,4'-piperidin]-2(4H)-on (E68); (E)-6-(3-(3-(benzoefuran-2-yl)azetidin-l-yl)-3-oxoprop-l-en-l-yl)-l'-methyl-lH-spiro[[l,8]naphthyridin-3,4’-piperidin]-2(4H)-on (E69); 6-(((E)-3-oxo-3-(3-((E)-l-(propoxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E70); eller 6-(((E)-3-oxo-3-(3-((Z)-l-(propoxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-3,4-dihydro- I, 8-naphthyridin-2(lH)-on (E71); eller et farmaceutisk acceptabelt salt eller solvat deraf.
10. Forbindelse med formlen (I) som defineret i krav 9, som er 6-((E)-3-oxo-3-(3-((E)-l- (propoxyimino)ethyl)azetidin-l-yl)prop-l-enyl)-3,4-dihydro-l,8-naphthyridin-2(lH)-on (E70). II. Farmaceutisk sammensætning omfattende en forbindelse med formlen (I) som defineret i et hvilket som helst af kravene 1 til 10, i forbindelse med et farmaceutisk acceptabelt hjælpe- eller bærestof.
12. Forbindelse med formlen (I) som defineret i et hvilket som helst af kravene 1 til 10 til brug i behandling.
13. Forbindelse med formlen (I) som defineret i et hvilket som helst af kravene 1 til 10 uden forbehold til anvendelse i behandling af mikroorganismeforvoldte infektioner.
14. Forbindelse med formlen (I) til anvendelse ifølge krav 13 i kombination med et eller flere andre lægemidler.
15. Forbindelse med formlen (I) til anvendelse ifølge krav 14, hvor de andre lægemidler er antibiotika.
16. Farmaceutisk sammensætning omfattende en forbindelse med formlen (I) som defineret i et hvilket som helst af kravene 1 til 10 uden forbehold til anvendelse i behandling af mikroorganismeforvoldte infektioner.
17. Forbindelse eller sammensætning til anvendelse som defineret i et hvilket som helst af kravene 13 til 16, hvor den mikroorganismeforvoldte infektion er en human eller animalsk infektion med mikroorganismepatogener udvalgt fra gruppen bestående af Staphylococcus aureus, Bacillus anthracis, Chlamydophila pneumoniae, Haemophilus influenzae, Helicobacter pylori, Klebsiella pneumoniae, Neisseria meningitidis, S. intermedius, P. multocida, B. bronchiseptica, M. haemolytica, A. pleuropneumoniae., Mycobacterium tuberculosis og Plasmodium falciparum.
18. Fremgangsmåde til fremstilling af forbindelsen med formlen (I) som defineret i et hvilket som helst af kravene 1 til 10, hvilken fremgangsmåde omfatter: (a) at omsætte en forbindelse med formlen (II):
(Π) hvor R3 er som defineret ovenfor med hensyn til forbindelser med formlen (I), med en forbindelse med formlen (III):
(III) hvor W, X, RI og R2 er som defineret ovenfor med hensyn til forbindelser med formlen (I); eller (b) eller at omsætte en forbindelse med formlen (IV):
(IV) hvor R3 er som defineret ovenfor med hensyn til forbindelser med formlen (I), og L1 står
(Ill) hvor W, X, RI og R2 er som defineret ovenfor med hensyn til forbindelser med formlen (I); eller (c) at omsætte en forbindelse med formlen (V):
(V) hvor W, X, RI og R2 er som defineret ovenfor med hensyn til forbindelser med formlen (I), med en forbindelse med formlen L2-R3, hvor L2 står for en egnet afgangsgruppe; eventuelt derefter fulgt af: (d) at afbeskytte et beskyttet derivat af forbindelse (I); og eventuelt derefter fulgt af: (e) omsætning af en forbindelse med formlen (I) til en yderligere forbindelse med formlen (I)·
DK10776385.6T 2009-11-18 2010-11-17 Aza-heterocykliske akrylamider og anvendelse deraf som baktericider DK2501693T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26230909P 2009-11-18 2009-11-18
PCT/EP2010/067647 WO2011061214A1 (en) 2009-11-18 2010-11-17 Novel heterocyclic acrylamides and their use as pharmaceuticals

Publications (1)

Publication Number Publication Date
DK2501693T3 true DK2501693T3 (da) 2014-12-08

Family

ID=44059228

Family Applications (1)

Application Number Title Priority Date Filing Date
DK10776385.6T DK2501693T3 (da) 2009-11-18 2010-11-17 Aza-heterocykliske akrylamider og anvendelse deraf som baktericider

Country Status (17)

Country Link
US (3) US8846711B2 (da)
EP (1) EP2501693B1 (da)
JP (1) JP5816629B2 (da)
KR (1) KR20130010456A (da)
CN (1) CN102656158B (da)
AU (1) AU2010320963B2 (da)
BR (1) BR112012011793A2 (da)
CA (1) CA2776849A1 (da)
DK (1) DK2501693T3 (da)
ES (1) ES2526567T3 (da)
HK (1) HK1176358A1 (da)
IL (1) IL218934A0 (da)
MX (1) MX2012005759A (da)
NZ (1) NZ599444A (da)
PL (1) PL2501693T3 (da)
WO (1) WO2011061214A1 (da)
ZA (1) ZA201202489B (da)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2054422B1 (en) 2006-07-20 2017-06-14 Debiopharm International SA Acrylamide derivatives as fab i inhibitors
AU2010320963B2 (en) 2009-11-18 2015-07-09 Fab Pharma Sas Novel heterocyclic acrylamides and their use as pharmaceuticals
CN105503869A (zh) * 2011-08-10 2016-04-20 爱尔兰詹森科学公司 抗细菌的哌啶基取代的3,4-二氢-1h-[1,8]萘啶酮
JP6521631B2 (ja) 2011-08-10 2019-05-29 ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー 抗菌性ホモピペリジニル置換３，４−ジヒドロ−１ｈ−［１，８］−ナフチリジノン類
JO3611B1 (ar) * 2011-08-10 2020-08-27 Janssen Sciences Ireland Uc سايكلو بنتا (سي (بيرول 4,3 ثاني هيدرو 1 hمستبدله [8,1] نافثيريدينونات مضادة للجراثيم
CA2849057C (en) 2011-09-19 2021-05-11 Vitas Pharma Research Pvt Ltd Heterocyclic compounds as inhibitors of fatty acid biosynthesis for bacterial infections
US9062075B2 (en) 2011-12-02 2015-06-23 Aurigene Discovery Technologies Limited Tetrahydropyridine derivatives as FabI inhibitors
WO2013080222A1 (en) * 2011-12-02 2013-06-06 Aurigene Discovery Technologies Limited Substituted pyridine derivatives as fabi inhibitors
AR090880A1 (es) 2012-04-30 2014-12-10 Janssen R & D Ireland Derivados de pirimidina
MX356695B (es) 2012-06-19 2018-06-11 Debiopharm Int Sa Profarmacos derivados de (e)-n-metil-n-((3-metilbenzofuran-2-il)me til)-3-(7-oxo-5,6,7,8-tetrahidro-1,8-naftiridin-3-il) acrilamida.
BR112015002931B1 (pt) * 2012-08-10 2019-10-29 Janssen Sciences Ireland Uc compostos antibacterianos, seu uso, composição farmacêutica que os compreende e processo de preparação destes
EA201590339A1 (ru) * 2012-08-10 2015-06-30 Янссен Сайенсиз Айрлэнд Юси Новые антибактериальные соединения
WO2014072930A2 (en) * 2012-11-09 2014-05-15 Aurigene Discovery Technologies Limited Fused pyridine derivatives as antibacterial agents
WO2014195844A1 (en) * 2013-06-04 2014-12-11 Aurigene Discovery Technologies Limited TETRAHYDROPYRIDINE DERIVATIVES AS FabI INHIBITORS
CN104292142B (zh) * 2013-07-17 2019-05-14 天津大地康和医药技术有限公司 一种n-芳基杂环丁烷脱芳基方法
WO2015071780A1 (en) * 2013-11-12 2015-05-21 Aurigene Discovery Technologies Limited Alkylidine substituted heterocyclyl derivatives as anti-bacterial agents
CN104529854B (zh) * 2015-01-14 2016-10-05 武汉金联药业有限公司 一种取代氮杂环丁烷类医药中间体化合物的合成方法
RU2766579C2 (ru) 2015-07-02 2022-03-15 ХОРАЙЗОН ОРФАН ЭлЭлСи Цистеаминдиоксигеназа-резистентные аналоги цистеамина и их применение
KR20180114177A (ko) 2016-02-26 2018-10-17 데비오팜 인터네셔날 에스 에이 당뇨병성 족부 감염의 치료제
CN108440523A (zh) * 2018-04-23 2018-08-24 爱斯特（成都）生物制药股份有限公司 一种合成6-溴-3,4-二氢-1h-[1,8]萘啶-2-酮的新方法
CN114351128B (zh) * 2021-12-10 2022-12-13 江阴纳力新材料科技有限公司 镀铜液添加剂、镀铜液、镀铜薄膜及其制备方法、负极集流体、锂电池

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1020864C (zh) * 1988-09-14 1993-05-26 中国科学院上海有机化学研究所 醛的烯基化反应的催化剂及其应用
TW224042B (da) 1992-04-04 1994-05-21 Basf Ag
CA2220231A1 (en) 1996-03-15 1997-09-18 Ss Pharmaceutical Co., Ltd. Novel pyridine derivative and medicament containing the same as an effective ingredient
ATE421952T1 (de) 1996-05-01 2009-02-15 Ortho Mcneil Pharm Inc Carboxamidderivate von pyrrolidin, piperidin und hexahydropiperizin für behandlung von thrombosen
CZ302015B6 (cs) 1999-10-08 2010-09-08 Affinium Pharmaceuticals, Inc. Inhibitory Fab I
ATE420640T1 (de) 2001-04-06 2009-01-15 Affinium Pharm Inc Fab-i-inhibitoren
JP2004099499A (ja) * 2002-09-09 2004-04-02 Sanei Gen Ffi Inc 抗微生物剤
DK1575951T3 (da) 2002-12-06 2014-09-15 Debiopharm Int Sa Heterocykliske forbindelser, fremgangsmåder til fremstilling deraf og deres anvendelse i terapi
SI1828167T1 (sl) 2004-06-04 2014-12-31 Debiopharm International Sa Forum "Apres-Demain" Akrilamidni derivati kot anitibiotična sredstva
BRPI0607304A2 (pt) 2005-01-26 2009-08-25 Allergan Inc compostos tendo atividade analgésica e/ou imunoestimulante
WO2007067416A2 (en) 2005-12-05 2007-06-14 Affinium Pharmaceuticals, Inc. Heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents
WO2007086584A1 (ja) * 2006-01-30 2007-08-02 Meiji Seika Kaisha, Ltd. 新規ＦａｂＫおよびＦａｂＩ／Ｋ阻害剤
EP1845087A1 (en) 2006-04-14 2007-10-17 Mutabilis SA Hydroxyphenyl derivatives and biological applications thereof
EP2054422B1 (en) 2006-07-20 2017-06-14 Debiopharm International SA Acrylamide derivatives as fab i inhibitors
EP1939180A1 (en) 2006-12-20 2008-07-02 sanofi-aventis Heteroarylacrylamides and their use as pharmaceuticals for the stimulation of the expression of endothelial NO synthase
EP1942104A1 (en) 2006-12-20 2008-07-09 sanofi-aventis Heteroarylcyclopropanecarboxamides and their use as pharmaceuticals
WO2008098374A1 (en) 2007-02-16 2008-08-21 Affinium Pharmaceuticals, Inc. Salts, prodrugs and polymorphs of fab i inhibitors
WO2009110002A1 (en) * 2008-03-05 2009-09-11 Council Of Scientific & Industrial Research Novel efflux pump inhibitors
JP2012102018A (ja) * 2009-03-03 2012-05-31 Astellas Pharma Inc アミド化合物
AU2010320963B2 (en) 2009-11-18 2015-07-09 Fab Pharma Sas Novel heterocyclic acrylamides and their use as pharmaceuticals

Also Published As

Publication number Publication date
JP5816629B2 (ja) 2015-11-18
WO2011061214A1 (en) 2011-05-26
AU2010320963B2 (en) 2015-07-09
HK1176358A1 (en) 2013-07-26
CN102656158A (zh) 2012-09-05
MX2012005759A (es) 2012-10-03
PL2501693T3 (pl) 2015-03-31
AU2010320963A1 (en) 2012-05-03
KR20130010456A (ko) 2013-01-28
US9321769B2 (en) 2016-04-26
CA2776849A1 (en) 2011-05-26
US20140357617A1 (en) 2014-12-04
ES2526567T3 (es) 2015-01-13
EP2501693A1 (en) 2012-09-26
EP2501693B1 (en) 2014-09-17
CN102656158B (zh) 2015-02-11
JP2013511486A (ja) 2013-04-04
US20150232466A1 (en) 2015-08-20
IL218934A0 (en) 2012-07-31
ZA201202489B (en) 2013-02-27
US9051321B2 (en) 2015-06-09
BR112012011793A2 (pt) 2019-09-24
US8846711B2 (en) 2014-09-30
US20120277207A1 (en) 2012-11-01
NZ599444A (en) 2014-02-28

Similar Documents

Publication Publication Date Title
DK2501693T3 (da) Aza-heterocykliske akrylamider og anvendelse deraf som baktericider
US11912699B2 (en) Tau-protein targeting compounds and associated
US10301305B2 (en) Heteroaromatic derivatives and their use as pharmaceuticals
US9062002B2 (en) Substituted pyridine derivatives as FabI inhibitors
US11524959B1 (en) Indole and azaindole inhibitors of pad enzymes
KR20140097118A (ko) 항균 화합물 및 이의 사용 방법
CA3140257C (en) Next-generation modulators of stimulator of interferon genes (sting)
WO2014072930A2 (en) Fused pyridine derivatives as antibacterial agents
KR20230022829A (ko) Rna 결합 단백질 또는 rna 변형 단백질을 표적으로 하는 화합물
JP7426486B2 (ja) インターフェロン遺伝子刺激因子（ｓｔｉｎｇ）のモジュレーターとしての複素環式化合物
CN117813086A (zh) 作为ccr6抑制剂的芳基磺酰基(羟基)哌啶