Nothing Special   »   [go: up one dir, main page]

HRP20230162T1 - Heteroarilni inhibitori enzima pde4 - Google Patents

Heteroarilni inhibitori enzima pde4 Download PDF

Info

Publication number
HRP20230162T1
HRP20230162T1 HRP20230162TT HRP20230162T HRP20230162T1 HR P20230162 T1 HRP20230162 T1 HR P20230162T1 HR P20230162T T HRP20230162T T HR P20230162TT HR P20230162 T HRP20230162 T HR P20230162T HR P20230162 T1 HRP20230162 T1 HR P20230162T1
Authority
HR
Croatia
Prior art keywords
compound according
alkyl
cyano
halogen
compounds
Prior art date
Application number
HRP20230162TT
Other languages
English (en)
Inventor
Mark E. Gurney
Timothy J. Hagen
Xuesheng MO
A. Vellekoop
Donna L. Romero
Robert F. Campbell
Joel R. Walker
Lei Zhu
Original Assignee
Tetra Discovery Partners Llc
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 Tetra Discovery Partners Llc filed Critical Tetra Discovery Partners Llc
Publication of HRP20230162T1 publication Critical patent/HRP20230162T1/hr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/69—Boron compounds
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • 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
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/12—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 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

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)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (10)

1. Spoj koji sadrži bilo koju od strukturnih formula XIII, XIV, XV i XVI: [image] ili sol takvoj spoja, pri čemu: Y označava CH2; X se odabire između spojeva CH i N; R5 je benzoksaborol ili se odabire između fenila i piridinila, od kojih je svaki para-supstituiran sa supstituentom oblika R8-R9-(R10)a(R10)b, a opcionalno se može supstituirati supstituentom R13; R8 odabire se između veze i C1-6 alkila; R9 odabire se između halogena, C1-6 alkila, C1-6 haloalkila, C1-6 hidroksialkila, C1-6 alkoksija, C1-6 haloalkoksija, cijano, -C(O)N-, S(O)2-, B(OH)2, monocikličkog heterocikloalkila od 5 ili 6 članova te monocikličkog heteroarila od 5 ili 6 članova; Svaki od spojeva (R10)a i (R10)b neovisno se odabire između vodika, halogena, trifluorometila, trifluorometoksija, hidroksila, C1-6 hidroksialkila, cijano, okso, C1-6 alkila, C(O)OH i C(O)O C1-6 alkila ili se može izostaviti; R13 odabire se između halogena, hidroksija, C1-6 alkila, trifluorometila, C1-6 alkoksija, trifluorometoksija, NH2 i cijano; R6 odabire se između 3-klorofenila, 5-kloro-2-tienila i ciklopentila koji se opcionalno supstituira jednim ili dvama spojevima R14 i ciklopentoksija koji se opcionalno supstituira jednim ili dvama spojevima R14; i svaki R14 neovisno se odabire između halogena, hidroksija, C1-6 alkila, trifluorometila, C1-6 alkoksija, trifluoromet-oksija, NH2 i cijano.
2. Spoj prema zahtjevu 1, pri čemu je R5 fenil koji se para-supstituira sa supstituentom oblika R8-R9-(R10)a(R10)b.
3. Spoj prema zahtjevu 2, pri čemu je R8 veza.
4. Spoj prema zahtjevu 2, pri čemu je R8 C1-6 alkil.
5. Spoj prema zahtjevu 3, pri čemu X predstavlja N.
6. Spoj prema zahtjevu 3, pri čemu X predstavlja CH.
7. Spoj prema zahtjevu 5, pri čemu se R6 odabire između 3-klorofenila i 5-kloro-2-tienila.
8. Spoj prema zahtjevu 7, pri čemu je R6 3-klorofenil.
9. Spoj prema bilo kojem zahtjevu od 1 do 8 koji se upotrebljava za poboljšanje kognitivnih sposobnosti.
10. Farmaceutska mješavina koja se sastoji od spoja prema bilo kojem zahtjevu od 1 do 8 zajedno s farmaceutski prihvatljivim nosačem.
HRP20230162TT 2012-10-25 2013-10-24 Heteroarilni inhibitori enzima pde4 HRP20230162T1 (hr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261718285P 2012-10-25 2012-10-25
US201261733675P 2012-12-05 2012-12-05
US201361776937P 2013-03-12 2013-03-12
EP21156065.1A EP3842420B1 (en) 2012-10-25 2013-10-24 Heteroaryl inhibitors of pde4

Publications (1)

Publication Number Publication Date
HRP20230162T1 true HRP20230162T1 (hr) 2023-04-14

Family

ID=50545269

Family Applications (1)

Application Number Title Priority Date Filing Date
HRP20230162TT HRP20230162T1 (hr) 2012-10-25 2013-10-24 Heteroarilni inhibitori enzima pde4

Country Status (23)

Country Link
US (8) US9221843B2 (hr)
EP (2) EP3842420B1 (hr)
JP (1) JP6289485B2 (hr)
KR (1) KR102189560B1 (hr)
CN (1) CN104768932B (hr)
AU (1) AU2013334236B2 (hr)
BR (1) BR112015009168B1 (hr)
CA (1) CA2886263C (hr)
CL (1) CL2015001068A1 (hr)
DK (1) DK2912019T3 (hr)
ES (1) ES2871821T3 (hr)
HK (1) HK1208026A1 (hr)
HR (1) HRP20230162T1 (hr)
HU (1) HUE056251T2 (hr)
IL (1) IL238409A (hr)
LT (1) LT3842420T (hr)
MX (1) MX368959B (hr)
NZ (1) NZ705881A (hr)
PL (1) PL2912019T3 (hr)
PT (1) PT2912019T (hr)
SG (1) SG11201502050XA (hr)
SI (1) SI3842420T1 (hr)
WO (1) WO2014066659A1 (hr)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013186159A1 (en) 2012-06-13 2013-12-19 F. Hoffmann-La Roche Ag New diazaspirocycloalkane and azaspirocycloalkane
IN2015DN00960A (hr) 2012-09-25 2015-06-12 Hoffmann La Roche
WO2014066659A1 (en) 2012-10-25 2014-05-01 Tetra Discovery Partners, Llc. Heteroaryl inhibitors of pde4
AU2014211755B2 (en) 2013-02-04 2017-07-06 Grunenthal Gmbh 4-amino substituted condensed pyrimidine compounds as PDE4 inhibitors
MX2015009677A (es) * 2013-02-04 2015-11-25 Gruenenthal Gmbh Compuestos de pirimidina condensada sustituida novedosos.
AR095079A1 (es) 2013-03-12 2015-09-16 Hoffmann La Roche Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo
UA118201C2 (uk) 2013-11-26 2018-12-10 Ф. Хоффманн-Ля Рош Аг НОВИЙ ОКТАГІДРОЦИКЛОБУТА[1,2-c;3,4-c']ДИПІРОЛ-2-ІЛ
EA032357B1 (ru) 2014-03-26 2019-05-31 Ф. Хоффманн-Ля Рош Аг Конденсированные [1,4]диазепиновые соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa)
RS59477B1 (sr) 2014-03-26 2019-12-31 Hoffmann La Roche Biciklička jedinjenja kao inhibitori proizvodnje autotaksina (atx) i lizofosfatidne kiseline (lpa)
US10442788B2 (en) 2015-04-01 2019-10-15 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
MA41898A (fr) 2015-04-10 2018-02-13 Hoffmann La Roche Dérivés de quinazolinone bicyclique
US10738035B2 (en) 2015-05-13 2020-08-11 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
US10179131B2 (en) 2015-07-13 2019-01-15 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
US10301255B2 (en) 2015-07-22 2019-05-28 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
CR20180058A (es) 2015-09-04 2018-02-26 Hoffmann La Roche Nuevos derivados de fenoximetilo
PE20180233A1 (es) 2015-09-24 2018-01-31 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores duales de atx / ca
PE20180451A1 (es) 2015-09-24 2018-03-05 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores de atx
WO2017050791A1 (en) 2015-09-24 2017-03-30 F. Hoffmann-La Roche Ag New bicyclic compounds as dual atx/ca inhibitors
PE20180461A1 (es) 2015-09-24 2018-03-06 Hoffmann La Roche Nuevos compuestos biciclicos como inhibidores de la atx
US10280175B2 (en) 2016-02-02 2019-05-07 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
MY198617A (en) 2016-03-07 2023-09-11 Enanta Pharm Inc Hepatitis b antiviral agents
US10189846B2 (en) 2016-06-10 2019-01-29 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
CN110382484B (zh) 2017-03-16 2022-12-06 豪夫迈·罗氏有限公司 新的作为atx抑制剂的二环化合物
BR112019019017A2 (pt) 2017-03-16 2020-04-14 Hoffmann La Roche compostos heterocíclicos de utilidade como inibidores duplos de atx/ca
IL272941B2 (en) 2017-08-28 2023-03-01 Enanta Pharm Inc Antiviral agents for viral hepatitis b
EP3684775A1 (en) 2017-09-20 2020-07-29 Leo Pharma A/S Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors
TW201936192A (zh) 2017-12-06 2019-09-16 美商因那塔製藥公司 B 型肝炎抗病毒試劑
US10428070B2 (en) 2017-12-06 2019-10-01 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
FI3724196T3 (fi) * 2017-12-15 2023-01-31 Substituoituja atsetidiinidihydrotienopyridiinejä ja niiden käyttö fosfodiesteraasin estäjinä
JP7198820B2 (ja) 2017-12-15 2023-01-04 ユニオン・セラピューティクス・アクティエセルスカブ 置換アゼチジンジヒドロチエノピリミジンおよびホスホジエステラーゼ阻害剤としてのそれらの使用
WO2019143902A2 (en) 2018-01-22 2019-07-25 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
US10729688B2 (en) 2018-03-29 2020-08-04 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
WO2019193091A1 (en) 2018-04-05 2019-10-10 Universiteit Hasselt Selective pde4d inhibitors against demyelinating diseases
CN108997394A (zh) * 2018-06-12 2018-12-14 广州百霆医药科技有限公司 苯并氧杂硼杂环戊烷类化合物及其制备方法
CN112955142A (zh) 2018-09-21 2021-06-11 英安塔制药有限公司 官能化杂环化合物作为抗病毒剂
ES2974208T3 (es) * 2018-10-05 2024-06-26 Pfizer Inhibidores de PDE4 que contienen boro
SG11202105007TA (en) 2018-11-21 2021-06-29 Enanta Pharm Inc Functionalized heterocycles as antiviral agents
CN111635400A (zh) 2019-03-02 2020-09-08 察略盛医药科技(上海)有限公司 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途
EP3956311A1 (en) * 2019-04-18 2022-02-23 Tetra Discovery Partners, Inc. Salts and polymorphs of a pde4 inhibitor
EP3969458A4 (en) 2019-05-13 2023-05-17 Borah, Inc. CHEMICAL COMPOUNDS
WO2020247444A1 (en) 2019-06-03 2020-12-10 Enanta Pharmaceuticals, Inc, Hepatitis b antiviral agents
WO2020247561A1 (en) 2019-06-04 2020-12-10 Enanta Pharmaceuticals, Inc, Hepatitis b antiviral agents
WO2020247575A1 (en) 2019-06-04 2020-12-10 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
WO2021003501A1 (en) * 2019-07-03 2021-01-07 Boragen, Inc. Chemical compounds
WO2021007488A1 (en) 2019-07-11 2021-01-14 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
WO2021055425A2 (en) 2019-09-17 2021-03-25 Enanta Pharmaceuticals, Inc. Functionalized heterocycles as antiviral agents
WO2021188414A1 (en) 2020-03-16 2021-09-23 Enanta Pharmaceuticals, Inc. Functionalized heterocyclic compounds as antiviral agents
CN114149410A (zh) * 2020-09-07 2022-03-08 四川科伦博泰生物医药股份有限公司 吡啶并环类化合物及其制备方法和用途
WO2022099284A1 (en) * 2020-11-05 2022-05-12 Young Biopharma, Llc Novel capsaicin analogs and uses thereof
CN115521946B (zh) * 2022-10-14 2024-06-21 浙江玖世生物科技有限公司 一种TiOx基光酶催化剂合成(R)-1-[3,5-二(三氟甲基)]苯乙醇的方法
WO2024135840A1 (ja) * 2022-12-23 2024-06-27 塩野義製薬株式会社 Ｐｄｅ４阻害剤を含有するカプセル剤または顆粒
CN118871444A (zh) * 2023-02-28 2024-10-29 上海翊石医药科技有限公司 二氢噻吩并嘧啶衍生物的制备方法和用途

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK23392D0 (da) 1992-02-24 1992-02-24 Novo Nordisk As Heterocykliske forbindelser, deres anvendelse og fremstilling
FR2754260B1 (fr) 1996-10-04 1998-10-30 Adir Nouveaux derives substitues de biphenyle ou de phenylpyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
AU5648599A (en) * 1998-09-11 2000-04-03 Kyorin Pharmaceutical Co. Ltd. Phosphonic ester derivatives and process for producing the same
JP2005530707A (ja) 2002-03-08 2005-10-13 イーライ・リリー・アンド・カンパニー キナーゼ阻害物質
WO2004066952A2 (en) 2003-01-29 2004-08-12 Incyte Corporation Benzoxazole, benzothiazole, and benzimidazole derivatives for the treatment of cancer and other diseases
JP2006123639A (ja) 2004-10-27 2006-05-18 Mitsubishi Electric Corp ホームドア状態認識システム
WO2006123639A1 (ja) * 2005-05-18 2006-11-23 Asahi Kasei Pharma Corporation ピリミジン誘導体
US20060293343A1 (en) * 2005-05-18 2006-12-28 Asahi Kasei Pharma Corporation Pyrimidine derivatives
US7919519B2 (en) 2005-11-23 2011-04-05 Epix Pharmaceuticals Inc. S1P receptor modulating compounds and use thereof
WO2009146388A1 (en) 2008-05-28 2009-12-03 The Trustees Of Columbia University In The City Of New York Voxel-based methods for assessing subjects using positron emission tomography
EP2348863A4 (en) * 2008-09-04 2012-03-07 Anacor Pharmaceuticals Inc BORN SMALL MOLECULES
RU2380890C1 (ru) 2008-10-17 2010-02-10 Государственное образовательное учреждение высшего профессионального образования Марийский государственный технический университет Способ испытания травяного покрова на прирусловой пойме реки
WO2010059838A2 (en) 2008-11-20 2010-05-27 Decode Genetics Ehf Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects
CA2753604A1 (en) * 2009-02-27 2010-09-02 Boehringer Ingelheim International Gmbh Drug combinations containing pde4-inhibitors and nsaids
EP2380890A1 (en) * 2010-04-23 2011-10-26 Almirall, S.A. New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors
US8889123B2 (en) * 2010-08-19 2014-11-18 Allergan, Inc. Compositions and soft tissue replacement methods
WO2014066659A1 (en) 2012-10-25 2014-05-01 Tetra Discovery Partners, Llc. Heteroaryl inhibitors of pde4
MX2015009677A (es) * 2013-02-04 2015-11-25 Gruenenthal Gmbh Compuestos de pirimidina condensada sustituida novedosos.
US20150086480A1 (en) 2013-09-26 2015-03-26 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
WO2016049595A1 (en) 2014-09-26 2016-03-31 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
EP3956311A1 (en) * 2019-04-18 2022-02-23 Tetra Discovery Partners, Inc. Salts and polymorphs of a pde4 inhibitor

Also Published As

Publication number Publication date
US9777024B2 (en) 2017-10-03
US11401286B2 (en) 2022-08-02
WO2014066659A9 (en) 2015-02-12
US20170342094A1 (en) 2017-11-30
EP3842420B1 (en) 2022-12-07
WO2014066659A1 (en) 2014-05-01
SG11201502050XA (en) 2015-04-29
US20200354384A1 (en) 2020-11-12
US9221843B2 (en) 2015-12-29
MX368959B (es) 2019-10-23
AU2013334236B2 (en) 2018-04-05
KR102189560B1 (ko) 2020-12-11
CN104768932A (zh) 2015-07-08
KR20150074004A (ko) 2015-07-01
EP2912019A1 (en) 2015-09-02
EP3842420A1 (en) 2021-06-30
IL238409A (en) 2017-08-31
US10626129B2 (en) 2020-04-21
HUE056251T2 (hu) 2022-02-28
MX2015005015A (es) 2015-11-23
US11767334B2 (en) 2023-09-26
US20230024240A1 (en) 2023-01-26
NZ705881A (en) 2018-04-27
HK1208026A1 (en) 2016-02-19
EP2912019B1 (en) 2021-03-24
JP2016505512A (ja) 2016-02-25
BR112015009168A2 (pt) 2017-07-04
IL238409A0 (en) 2015-06-30
PT2912019T (pt) 2021-05-25
US20190055269A1 (en) 2019-02-21
CL2015001068A1 (es) 2016-01-04
US20150119362A1 (en) 2015-04-30
CA2886263A1 (en) 2014-05-01
CA2886263C (en) 2021-04-13
US20230348501A1 (en) 2023-11-02
US10093686B2 (en) 2018-10-09
US20190270759A1 (en) 2019-09-05
US10364258B2 (en) 2019-07-30
PL2912019T3 (pl) 2021-11-02
CN104768932B (zh) 2018-08-07
BR112015009168B1 (pt) 2022-09-27
DK2912019T3 (da) 2021-05-25
US20160137672A1 (en) 2016-05-19
SI3842420T1 (sl) 2023-04-28
LT3842420T (lt) 2023-02-27
JP6289485B2 (ja) 2018-03-07
ES2871821T3 (es) 2021-11-02
AU2013334236A1 (en) 2015-04-02
EP2912019A4 (en) 2016-04-20

Similar Documents

Publication Publication Date Title
HRP20230162T1 (hr) Heteroarilni inhibitori enzima pde4
HRP20211922T1 (hr) Postupci i intermedijeri za pripravu jak inhibitora
HRP20180483T1 (hr) Spoj kinolona
HRP20201934T1 (hr) Anti-fibrotički piridinoni
EA201591429A1 (ru) 2,3-дизамещенные производные 1-ацил-4-амино-1,2,3,4-тетрагидрохинолинов и их применение в качестве ингибиторов бромодомена
HRP20201657T1 (hr) Mikrobiocidni derivati kinolin (tio)karboksamida
HRP20171961T1 (hr) Kemijski spojevi
MX2013005008A (es) Derivados de carboxamida y urea heteroaromaticos sustituidos como ligandos del receptor vanilloide.
RS54708B1 (en) ARYLETINYL DERIVATIVES
MA37519B1 (fr) Composés et compositions pour inhiber l'activité d'abl1, abl2 et bcr-abl1
HRP20211605T1 (hr) Spojeni pentaciklični derivati imidazola
BR112015021983A8 (pt) compostos heterocíclicos, composições e usos dos mesmos
CO6321289A2 (es) Compuestos de ester boronato y composiciones farmaceuticas de los mismos
EA201001683A1 (ru) Производные фенил- или пиридинилзамещенных индазолов
EP4272824A3 (en) Substituted 2-azabicycles and their use as orexin receptor modulators
AR080056A1 (es) Derivados de ciclohexil-amida como antagonistas de los receptores de crf
MD4490C1 (ro) Noi compuşi de indolizină, procedeu de obţinere a lor şi compoziţii farmaceutice care îi conţin
HRP20240422T1 (hr) Novi azoli za moduliranje vezanja i djelovanja fxr (nr1h4)
RS54183B1 (en) PIRAZOLE DERIVATIVES
HRP20191431T1 (hr) Postupak za pripravu (4s)-4-(4-cijano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1-6- naftiridin-3-karboksamida i njegovo pročišćavanje za uporabu kao aktivni farmaceutski pripravak
MY169986A (en) Benzimidazole-proline derivatives
BR112015022058A2 (pt) 7-azabiciclos substituídos e o uso destes como moduladores do receptor de orexina
MD20150019A2 (ro) Alcoxipirazoli în calitate de activatori ai guanilat ciclazei solubile
MY192641A (en) Novel pyrimidine and pyridine compounds and their usage
CO6801736A2 (es) Derivados heterocíclicos de amina