[go: up one dir, main page]

AR059292A1 - Inhibidores de la polimerasa viral - Google Patents

Inhibidores de la polimerasa viral

Info

Publication number
AR059292A1
AR059292A1 ARP070100441A ARP070100441A AR059292A1 AR 059292 A1 AR059292 A1 AR 059292A1 AR P070100441 A ARP070100441 A AR P070100441A AR P070100441 A ARP070100441 A AR P070100441A AR 059292 A1 AR059292 A1 AR 059292A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
het
optionally substituted
independently selected
Prior art date
Application number
ARP070100441A
Other languages
English (en)
Inventor
Timothy Stammers
Rene Coulombe
Gulrez Fazal
Jean Rancourt
Bounkham Thavonekham
Original Assignee
Boehringer Ingelheim Vetmed
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 Boehringer Ingelheim Vetmed filed Critical Boehringer Ingelheim Vetmed
Publication of AR059292A1 publication Critical patent/AR059292A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • C07D207/06—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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon 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
    • C07D211/36—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 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • C07D211/36—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 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D211/36—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 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—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
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • 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
    • C07D277/32—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 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen 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 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Los compuestos de la presente son utiles como inhibidores de la polimerasa NS5B del virus de la hepatitis C. Reivindicacion 1: Un compuesto de formula (1): e la que X se selecciona de Q y S; R2 es arilo, opcionalmente sustituido con R20, en donde R20 es 1 a 5 sustituyentes, cada uno independientemente seleccionado de: a) halo, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-7 o cicloalquil C 3-7-alquilo C1-6; b) -N(R7)R8 o -Y-N(R7)R8, en donde Y se selecciona de -C(=O)-, -SO2 y -alquileno C1- 6; R7 se selecciona, en cada caso independientemente, de H y alquilo C1-6; y R8 se selecciona, en cada caso independientemente, de H, alquilo C1-6, haloalquilo C1-6, cicloaIquilo C3-7, cicloalquil C3-7-alquilo C1-6, arilo, Het, -C(=O)-R9, -C(=O)OR9 y-C(=O)NHR9; en donde el alquilo C1-6 está opcionalmente sustituido con -OH, -O-alquilo C1-6, ciano, -NH2-, -Nhalquilo C1-4 o -N(alquilo C1-4)2; y en donde cada uno del arilo y Het está opcionalmente sustituido con 1 a 3 sustituyentes, cada uno independientemente seleccionado de i) halo, -OH, haloalquilo C1-6, -C(=O)-alquilo C1-6, -SO2alquilo C1-6, -C(=O)-NH2, -C(=O)-Nhalquilo C1-4, -C(=O)-N(aIquilo C-4)2, -NH2, -Nhalquilo C1-4, -N(alquilo C1-4)2 o -NH-C(=O)alquilo C1-4; ii) alquilo C1-6, opcionalmente sustituido con -OH o -O-alquilo C1-6; y iii) arilo o Het, en donde cada uno del arilo y Het está opcionalmente sustituido con halo o alquilo C1-6; y en donde R9 se selecciona de: i) alquilo C1-6, opcionalmente sustituido con -COOH, - NH2, -NHalquilo C1-4 o -N(alquilo C1-4)2 y ii) Het, opcionalmente sustituido con alquilo C1-6; o R7 y R8 están enlazados, junto con el N al que están unidos, para formar un heterociclo de 4 a 7 miembros, que opcionalmente contiene 1 a 3 heteroátomos adicionales, cada uno independientemente seleccionado de N, O y S, o un heteropoliciclo de 7 a 14 miembros, que opcionalmente contiene 1 a 3 heteroátomos adicionales, cada uno independientemente seleccionado de N, O y S; estando el heterociclo y el heteropoliciclo cada uno opcionalmente sustituido con 1 a 3 sustituyentes, cada uno independientemente seleccionado de: i) halo, -OH, haloalquilo C1-6, -C(=O)-alquilo C1-6, -SO2alquilo C1-6, -C(=O)-NH2, -C(=O)-NHalquilo C1-4, -C(=O)-N(alquilo C1- 4)2, -NH2, -NHalquilo C1-4, -N(alquilo C1-4)2 o -NH-C(=O)alquilo C1-4); ii) alquilo C1-6, opcionalmente sustituido con -OH o -O-alquilo C1-6; y iii) arilo o Het, en donde cada uno del arilo y Het está opcionalmente sustituido con halo o alquilo C1- 6; c) arilo, aril-alquilo C1-6, Het o Het-alquilo C1-6, en donde cada uno del arilo, aril-alquilo C1-6, Het y Het-alquilo C1-6 está opcionalmente sustituido con 1 a 3 sustituyentes, cada uno independientemente seleccionado de i) halo, -OH, haloalquilo C1-6, -C(=O)-alquilo C1-6, -SO2alquilo C1-6; -C(=O)-NH2, -C(=O)-Nhalquilo C1-4, -C(=O)-N(alquilo C1-4)2, -NH2, -NHalquilo C1-4, -N(alquilo C1-4)2 o -NH-C(=O)alquilo C1-4; ii) alquilo C1-6, opcionalmente sustituido con -OH o -O-alquilo C1-6; y iii) arilo o Het, en donde cada uno del arilo y Het está opcionalmente sustituido con halo o alquilo C1-6; y d) -C(=O)-R10, -O-R10, -C(=O)-OR10, -alquiIeno C1-6-O-R10, -S-R10, -SO-R10, SO2-R10, -alquiIeno C1-6-S-R10, -alquileno C1-6-SO-R10 o -alquileno C1-6-SO2R10, en donde R10 se selecciona, en cada caso independientemente, de H, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, arilo y Het en donde el alquilo C1-6 está opcionalmente sustituido con -OH, - O-alquilo C1-6, ciano, -NH2, -NHalquilo C1-4 o -N(alquiloC1-4)2; y en donde cada uno del arilo y Het está opcionalmente sustituido con 1 a 3 sustituyentes, cada uno independientemente seleccionado de i) halo, -OH, haloalquilo C1-6, -C(=O)-alquiloC1- 6, -SO2alquilo C1-6, -C(=O)-NH2, -C(=O)-NHalquilo C1-4, -C(=O)-N(alquilo C1-4)2, -NH2, -NHalquilo C1-4, -N(alquilo C1-4)2 o -NH-C(=O)alquilo C1-4; ii) alquilo C1-6, opcionalmente sustituido con -OH o -O-alquilo C1-6; y iii) arilo o Het, en donde cada uno del arilo y Het está opcionalmente sustituido con halo o alquilo C1-6; con la condicion de que cuando X es O, R2 no es un grupo de la formula (2); R3 se selecciona de H, halo, alquilo C1-4, -O-alquilo C1-4, -S-alquilo C1-4, -NH2, -NHalquilo C1-4 y -N(alquilo C1-4)2; R5se selecciona de H, alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-3 y Het; estando el alquilo C1-6 y 1Het cada uno opcionalmente sustituido con 1 a 4 sustituyentes cada uno independientemente seleccionado de alquilo C1-6, -OH, -COOH, -C(=O)-alquilo C1-6, -C(=O)-O-alquilo C1-6), -C(=O)-NH-alquilo C1-6, -C(=O)-N(alquiIo C1-6)2 y -SO2aIquilo C1-6; y R6se selecciona de cicloalquilo C5-7, cicloalquil C5-7-alquilo C1-3, arilo y aril-alquilo C1-3; estando cada uno del cicloalquilo C5-7, cicloalquil C5-7-alquilo C1-3, arilo y aril-alquilo C1-3 opcionalmente sustituido con 1 a 5 sustituyentes, cada uno independientemente seleccionado de halo, alquilo C1-6, haloalquilo C1-6, -OH, -SH, -O-alquilo C1-4 y - S-alquilo C1-4; en donde Het es un heterociclo de 4 a 7 miembros saturado, insaturado o aromático que tiene 1 a 4 heteroátomos, cada uno independientemente seleccionado de O, N y S, o un heteropoliciclo de 7 a 14 miembros, saturado, insaturado o aromático que tiene, siempre que sea posible, 1 a 5 heteroátomos, cada uno independientemente seleccionado de O, N y S; o una dé sus sales o ésteres.
ARP070100441A 2006-02-03 2007-02-02 Inhibidores de la polimerasa viral AR059292A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76497806P 2006-02-03 2006-02-03

Publications (1)

Publication Number Publication Date
AR059292A1 true AR059292A1 (es) 2008-03-26

Family

ID=38327109

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070100441A AR059292A1 (es) 2006-02-03 2007-02-02 Inhibidores de la polimerasa viral

Country Status (16)

Country Link
US (1) US7816348B2 (es)
EP (1) EP1984323A4 (es)
JP (1) JP2009525287A (es)
KR (1) KR20080091294A (es)
CN (1) CN101410368A (es)
AR (1) AR059292A1 (es)
AU (1) AU2007211789A1 (es)
BR (1) BRPI0707689A2 (es)
CA (1) CA2638784A1 (es)
IL (1) IL193151A0 (es)
PE (1) PE20071326A1 (es)
RU (1) RU2008135239A (es)
TW (1) TW200804240A (es)
UY (1) UY30127A1 (es)
WO (1) WO2007087717A1 (es)
ZA (1) ZA200805855B (es)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7816348B2 (en) 2006-02-03 2010-10-19 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
KR20090042973A (ko) * 2006-08-17 2009-05-04 베링거 인겔하임 인터내셔날 게엠베하 바이러스 폴리머라제 억제제
EP2185539A4 (en) * 2007-08-03 2011-07-20 Boehringer Ingelheim Int VIRAL POLYMERASE INHIBITORS
JP2010535156A (ja) * 2007-08-03 2010-11-18 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ウイルスポリメラーゼ阻害剤
CN101827826A (zh) 2007-10-16 2010-09-08 诺瓦提斯公司 4-苯基-5-氧代-咪唑衍生物、其药物组合物及其应用
US8476257B2 (en) * 2007-12-19 2013-07-02 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
WO2010009166A1 (en) 2008-07-14 2010-01-21 Gilead Colorado, Inc. Oxindolyl inhibitor compounds
KR101591123B1 (ko) * 2008-07-15 2016-02-02 니폰 카야쿠 코., 엘티디. 6-아릴옥시퀴놀린 유도체의 제조방법 및 그 중간체
CN102271699A (zh) 2009-01-07 2011-12-07 西尼克斯公司 用于治疗hcv和hiv感染的环孢菌素衍生物
TW201035088A (en) 2009-02-27 2010-10-01 Supergen Inc Cyclopentathiophene/cyclohexathiophene DNA methyltransferase inhibitors
WO2010144371A1 (en) 2009-06-08 2010-12-16 Gilead Colorado, Inc. Alkanoylamino benzamide aniline hdac inihibitor compounds
AU2010259042A1 (en) 2009-06-08 2011-12-15 Gilead Sciences, Inc. Cycloalkylcarbamate benzamide aniline HDAC inhibitor compounds
US8410091B1 (en) * 2009-09-11 2013-04-02 Boehringer Ingelheim International Gmbh Process for preparation of substituted 2-amino-5-(5-(heterocyclemethyl)pyridin-2-yloxy)benzoic acid
WO2011032277A1 (en) * 2009-09-18 2011-03-24 Boehringer Ingelheim International Gmbh Quinazolinone derivatives as viral polymerase inhibitors
JP5983418B2 (ja) * 2013-01-18 2016-08-31 コニカミノルタ株式会社 光学フィルム、円偏光板および画像表示装置
CN106478548A (zh) * 2016-07-19 2017-03-08 贵州大学 一种6‑羟基灭草松的制备工艺
CN119684179B (zh) * 2024-12-17 2025-12-19 沈阳农业大学 一种二芳基醚类化合物及其制备方法和应用

Family Cites Families (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1507457A (en) * 1974-11-12 1978-04-12 Agfa Gevaert Fixer compositions used in planographic printing
LU85544A1 (fr) * 1984-09-19 1986-04-03 Cird Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique
US5633388A (en) * 1996-03-29 1997-05-27 Viropharma Incorporated Compounds, compositions and methods for treatment of hepatitis C
JP4452401B2 (ja) 1997-08-11 2010-04-21 ベーリンガー インゲルハイム （カナダ） リミテッド Ｃ型肝炎ウイルス阻害ペプチドアナログ
EP1003775B1 (en) 1997-08-11 2005-03-16 Boehringer Ingelheim (Canada) Ltd. Hepatitis c inhibitor peptides
AR022061A1 (es) 1998-08-10 2002-09-04 Boehringer Ingelheim Ca Ltd Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos.
US6323180B1 (en) 1998-08-10 2001-11-27 Boehringer Ingelheim (Canada) Ltd Hepatitis C inhibitor tri-peptides
UA74546C2 (en) 1999-04-06 2006-01-16 Boehringer Ingelheim Ca Ltd Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition
WO2001047883A1 (fr) * 1999-12-27 2001-07-05 Japan Tobacco Inc. Composes a cycles accoles et leur utilisation comme medicaments
US6434489B1 (en) * 2000-04-03 2002-08-13 Schering Corporation Compositions of hepatitis C virus NS5B polymerase and methods for crystallizing same
CA2405521C (en) 2000-04-05 2010-06-29 Schering Corporation Macrocyclic ns3-serine protease inhibitors of hepatitis c virus comprising n-cyclic p2 moieties
NZ521456A (en) 2000-04-19 2004-07-30 Schering Corp Macrocyclic NS3-Serine protease inhibitors of hepatitis C virus comprising alkyl and aryl alanine P2 moieties
US6448281B1 (en) 2000-07-06 2002-09-10 Boehringer Ingelheim (Canada) Ltd. Viral polymerase inhibitors
US7244721B2 (en) 2000-07-21 2007-07-17 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
AR034127A1 (es) 2000-07-21 2004-02-04 Schering Corp Imidazolidinonas como inhibidores de ns3-serina proteasa del virus de hepatitis c, composicion farmaceutica, un metodo para su preparacion, y el uso de las mismas para la manufactura de un medicamento
AR029851A1 (es) 2000-07-21 2003-07-16 Dendreon Corp Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c
ATE461207T1 (de) 2000-07-21 2010-04-15 Schering Corp Peptide als inhibitoren der ns3-serinprotease des hepatitis c virus
US7169760B2 (en) 2000-07-21 2007-01-30 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
PE20020707A1 (es) 2000-11-20 2002-08-11 Bristol Myers Squibb Co Compuestos tripeptidicos como inhibidores de la proteasa ns3 del virus de hepatitis c
HUP0303436A2 (hu) 2000-12-12 2004-01-28 Schering Corp. Diaril-peptidek mint a hepatitis C vírus NS3-szerin proteáz inhibitorai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk
JP4083422B2 (ja) * 2000-12-22 2008-04-30 石原産業株式会社 アニリン誘導体またはその塩ならびにそれらを含有するサイトカイン産生抑制剤
EP1256628A3 (en) 2001-05-10 2003-03-19 Agouron Pharmaceuticals, Inc. Hepatitis c virus (hcv) ns5b rna polymerase and mutants thereof
AR035543A1 (es) 2001-06-26 2004-06-16 Japan Tobacco Inc Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con
WO2003004458A1 (en) 2001-07-03 2003-01-16 Biovitrum Ab New compounds
CA2448737C (en) * 2001-07-20 2010-06-01 Boehringer Ingelheim (Canada) Ltd. Viral polymerase inhibitors
EP2335700A1 (en) 2001-07-25 2011-06-22 Boehringer Ingelheim (Canada) Ltd. Hepatitis C virus polymerase inhibitors with a heterobicylic structure
US20030134853A1 (en) 2001-09-26 2003-07-17 Priestley Eldon Scott Compounds useful for treating hepatitis C virus
US6867185B2 (en) 2001-12-20 2005-03-15 Bristol-Myers Squibb Company Inhibitors of hepatitis C virus
DE60329367D1 (de) 2002-01-23 2009-11-05 Schering Corp Verwendung bei der bekämpfung von hepatitis c virusinfektion
CA2369711A1 (en) 2002-01-30 2003-07-30 Boehringer Ingelheim (Canada) Ltd. Macrocyclic peptides active against the hepatitis c virus
CA2369970A1 (en) 2002-02-01 2003-08-01 Boehringer Ingelheim (Canada) Ltd. Hepatitis c inhibitor tri-peptides
CA2370396A1 (en) 2002-02-01 2003-08-01 Boehringer Ingelheim (Canada) Ltd. Hepatitis c inhibitor tri-peptides
WO2003082848A1 (en) * 2002-04-01 2003-10-09 Pfizer Inc. Pyranon and pyrandion inhibitors of hepatitis c virus rna-dependent rna polymerase
PL215228B1 (pl) 2002-05-20 2013-11-29 Bristol Myers Squibb Co Zwiazki tripeptydowe, ich zastosowanie i kompozycja farmaceutyczna je zawierajaca oraz jej zastosowanie
DE60324552D1 (en) 2002-05-20 2008-12-18 Bristol Myers Squibb Co Substituierte cycloalkyl p1' hepatitis c virus inhibitoren
MY140680A (en) 2002-05-20 2010-01-15 Bristol Myers Squibb Co Hepatitis c virus inhibitors
DE60334205D1 (en) 2002-05-20 2010-10-28 Bristol Myers Squibb Co Heterocyclische sulfonamid-hepatitis-c-virus-hemmer
EP1511751B1 (en) 2002-06-04 2008-03-19 Neogenesis Pharmaceuticals, Inc. Pyrazolo[1,5-a]pyrimidine compounds as antiviral agents
AU2003256334A1 (en) * 2002-07-01 2004-01-19 Pharmacia And Upjohn Company Inhibitors of hcv ns5b polymerase
US20040138109A1 (en) 2002-09-30 2004-07-15 Boehringer Ingelheim Pharmaceuticals, Inc. Potent inhibitor of HCV serine protease
US20050075279A1 (en) 2002-10-25 2005-04-07 Boehringer Ingelheim International Gmbh Macrocyclic peptides active against the hepatitis C virus
US20050159345A1 (en) 2002-10-29 2005-07-21 Boehringer Ingelheim International Gmbh Composition for the treatment of infection by Flaviviridae viruses
US7223785B2 (en) 2003-01-22 2007-05-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US7098231B2 (en) 2003-01-22 2006-08-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
CN1771050A (zh) 2003-02-07 2006-05-10 益安药业 丙型肝炎丝氨酸蛋白酶的大环抑制剂
EP1599496B1 (en) 2003-03-05 2010-11-03 Boehringer Ingelheim International GmbH Hepatitis c inhibitor peptide analogs
WO2004101605A1 (en) 2003-03-05 2004-11-25 Boehringer Ingelheim International Gmbh Hepatitis c inhibiting compounds
GB0307891D0 (en) 2003-04-04 2003-05-14 Angeletti P Ist Richerche Bio Chemical compounds,compositions and uses
ATE422895T1 (de) 2003-04-16 2009-03-15 Bristol Myers Squibb Co Makrocyclische isochinolinpeptidinhibitoren des hepatitis-c-virus
EP2143727B1 (en) 2003-04-18 2015-01-21 Enanta Pharmaceuticals, Inc. Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors
ES2456702T3 (es) 2003-05-09 2014-04-23 Boehringer Ingelheim International Gmbh Bolsillo de unión del inhibidor de la polimerasa NS5B del virus de la hepatitis C
EA009295B1 (ru) 2003-05-21 2007-12-28 Бёрингер Ингельхайм Интернациональ Гмбх Соединения в качестве ингибиторов вируса гепатита с
WO2004113365A2 (en) 2003-06-05 2004-12-29 Enanta Pharmaceuticals, Inc. Hepatitis c serine protease tri-peptide inhibitors
US7125845B2 (en) 2003-07-03 2006-10-24 Enanta Pharmaceuticals, Inc. Aza-peptide macrocyclic hepatitis C serine protease inhibitors
EP1651631A1 (en) 2003-08-01 2006-05-03 Genelabs Technologies, Inc. Bicyclic imidazol derivatives against flaviviridae
WO2005014543A1 (ja) 2003-08-06 2005-02-17 Japan Tobacco Inc. 縮合環化合物及びそのｈｃｖポリメラーゼ阻害剤としての利用
EP1664090A2 (en) 2003-08-26 2006-06-07 Schering Corporation Novel peptidomimetic ns3-serine protease inhibitors of hepatitis c virus
RS20060197A (sr) 2003-09-22 2008-09-29 Boehringer Ingelheim International Gmbh., Makrociklični peptidi koji su aktivni protiv hepatitisa c virusa
BRPI0414814A (pt) 2003-09-26 2006-11-14 Schering Corp inibidores macrocìclicos de protease de serina ns3 de vìrus de hepatite c
RS20110578A3 (en) 2003-10-14 2016-02-29 F. Hoffmann-La Roche Ltd MACROCYCLIC CARBOXYLIC ACIDS AND ACYLSULPHONAMIDES AS HCV REPLICATION INHIBITORS
US7132504B2 (en) 2003-11-12 2006-11-07 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
JPWO2005049622A1 (ja) 2003-11-19 2007-06-07 日本たばこ産業株式会社 ５−５員縮合複素環化合物及びそのｈｃｖポリメラーゼ阻害剤としての用途
US7135462B2 (en) 2003-11-20 2006-11-14 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
CN1902216A (zh) 2003-11-20 2007-01-24 先灵公司 丙肝病毒ns3蛋白酶的去肽化抑制剂
US7309708B2 (en) 2003-11-20 2007-12-18 Birstol-Myers Squibb Company Hepatitis C virus inhibitors
CA2549167A1 (en) 2003-12-11 2005-06-30 Schering Corporation Inhibitors of hepatitis c virus ns3/ns4a serine protease
JP4682155B2 (ja) 2004-01-21 2011-05-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃ型肝炎ウイルスに対して活性な大環状ペプチド
CN103319464A (zh) 2004-02-20 2013-09-25 贝林格尔.英格海姆国际有限公司 病毒聚合酶抑制剂
CA2557307A1 (en) 2004-02-27 2005-09-22 Schering Corporation 3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis c virus ns3 serine protease
CN1946690A (zh) 2004-02-27 2007-04-11 先灵公司 用作丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的含环丁烯二酮基团化合物
JP4874227B2 (ja) 2004-02-27 2012-02-15 シェーリング コーポレイション Ｃ型肝炎ウイルスのｎｓ３セリンプロテアーゼインヒビターとしての環状ｐ４’ｓを有する新規ケトアミド
WO2005087721A2 (en) 2004-02-27 2005-09-22 Schering Corporation Compounds as inhibitors of hepatitis c virus ns3 serine protease
EP1730165A1 (en) 2004-02-27 2006-12-13 Schering Corporation Inhibitors of hepatitis c virus ns3 protease
CN103102389A (zh) 2004-02-27 2013-05-15 默沙东公司 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的硫化合物
JP2007525511A (ja) 2004-02-27 2007-09-06 シェーリング　コーポレイション Ｃ型肝炎ウイルスｎｓ３セリンプロテアーゼの新規のインヒビターとしての化合物
AR049635A1 (es) 2004-05-06 2006-08-23 Schering Corp (1r,2s,5s)-n-((1s)-3-amino-1-(ciclobutilmetil)-2,3-dioxopropil)-3-((2s)-2-((((1,1-dimetiletil)amino)carbonil)amino)-3,3-dimetil-1-oxobutil)-6,6-dimetil-3-azabiciclo(3.1.0)hexan-2-carboxamida como inhibidor de la ns3/ns4a serina proteasa del virus de la hepatitis c
EP1773868B1 (en) 2004-05-20 2009-07-15 Schering Corporation Substituted prolines as inhibitors of hepatitis c virus ns3 serine protease
WO2005121132A1 (ja) 2004-06-11 2005-12-22 Shionogi & Co., Ltd. 抗ｈｃｖ作用を有する縮合ヘテロ環化合物
EP1763531A4 (en) 2004-06-28 2009-07-01 Boehringer Ingelheim Int ANALOGUE OF HEPATITIS-C INHIBITING PEPTIDES
UY29017A1 (es) 2004-07-16 2006-02-24 Boehringer Ingelheim Int Inhibidores de polimerasa viral
ATE512971T1 (de) 2004-07-20 2011-07-15 Boehringer Ingelheim Int Peptidanaloga als hepatitis c-hemmer
UY29016A1 (es) 2004-07-20 2006-02-24 Boehringer Ingelheim Int Analogos de dipeptidos inhibidores de la hepatitis c
US7816348B2 (en) 2006-02-03 2010-10-19 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
KR20090042973A (ko) 2006-08-17 2009-05-04 베링거 인겔하임 인터내셔날 게엠베하 바이러스 폴리머라제 억제제
EP2185539A4 (en) 2007-08-03 2011-07-20 Boehringer Ingelheim Int VIRAL POLYMERASE INHIBITORS
JP2010535156A (ja) 2007-08-03 2010-11-18 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ウイルスポリメラーゼ阻害剤
US8476257B2 (en) 2007-12-19 2013-07-02 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors

Also Published As

Publication number Publication date
US20070219176A1 (en) 2007-09-20
EP1984323A1 (en) 2008-10-29
UY30127A1 (es) 2007-09-28
EP1984323A4 (en) 2012-02-22
WO2007087717A1 (en) 2007-08-09
CN101410368A (zh) 2009-04-15
ZA200805855B (en) 2009-10-28
US7816348B2 (en) 2010-10-19
PE20071326A1 (es) 2008-02-21
TW200804240A (en) 2008-01-16
RU2008135239A (ru) 2010-03-10
BRPI0707689A2 (pt) 2011-05-10
AU2007211789A1 (en) 2007-08-09
IL193151A0 (en) 2009-02-11
CA2638784A1 (en) 2007-08-09
JP2009525287A (ja) 2009-07-09
KR20080091294A (ko) 2008-10-09

Similar Documents

Publication Publication Date Title
AR059292A1 (es) Inhibidores de la polimerasa viral
AR068050A1 (es) Inhibidores de la polimerasa viral
ES2515194T3 (es) Derivados de pirrolidina
AR047706A1 (es) Inhibidores de polimerasa viral
AR069832A1 (es) Inhibidores de la polimerasa virica
AR050430A1 (es) Analogos de dipeptidos inhibidores de la hepatitis c
AR078396A1 (es) Inhibidores de la polimerasa virica y composiciones farmaceuticas que los contienen
AR072913A1 (es) Naftiridinas sustituidas y su utilizacion como medicamento
AR076775A1 (es) Inhibidores de la replicacion del virus de la inmunodeficiencia humana
CO6251247A2 (es) Imidazoquinolinas con propiedades inmuno-moduladoras
AR072787A1 (es) Compuestos y composiciones como inhibidores de cinasa
AR090760A1 (es) Compuestos de benzotiazol y su uso contra el virus de hiv
AR060949A1 (es) Inhibidores de la replicacion del virus de la inmunodeficiencia humana
AR082619A1 (es) Inhibidores del virus de la hepatitis c
AR069544A1 (es) Inhibidores de la replicacion del virus de la inmunodeficiencia humana y composiciones farmaceuticas que los contienen
CO6180424A2 (es) Inhibodores espiro cetona de acetil-coa carboxilasa
AR075510A1 (es) Inhibidores del virus de la hepatitis c
AR064355A1 (es) Herbicidas derivados de isoxazol
AR050172A1 (es) Inhibidores de polimerasa viral
AR069334A1 (es) Inhibidores de la replicacion del virus de inmunodeficiencia humana
AR082029A1 (es) Derivados de heterociclos nitrogenados, composiciones y metodos para modular la via de señalizacion de wnt
AR072839A1 (es) Derivados adamantil diamida y usos de los mismos
AR073136A1 (es) Compuestos de pirrol
AR066946A1 (es) Compuestos heterociclicos antagonistas del receptor de histamina h3, y sus usos terapeuticos
AR058776A1 (es) Compuesto de piridina condensado

Legal Events

Date Code Title Description
FB Suspension of granting procedure