Aryloyl(oxy or amino)pentafluorosulfanylbenzene compound, pharmaceutically acceptable salt thereof, and prodrugs thereof
AssigneeUbe Industries, Ltd.
InventorsShigeyoshi NISHINO, Hidetaka SHIMA, Hiroyuki ODA, Tetsuro SHIMANO
Life of this patent
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Abstract
An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound having pharmacological action. The aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is represented by general formula (A-I), a pharmaceutically acceptable salt thereof, and a prodrug thereof, wherein all of parameters represent the same meanings as defined in the specification.
Claims7
An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound represented by general formula (A-I), a pharmaceutically acceptable salt thereof, or a prodrug thereof;
- wherein,
- p is an integer of 0 or 1;
- q is an integer of 0 or 1;
- m is an integer of 0 to 5;
- n is an integer of 1 to 3;
- Z represents —O— or —NH—;
- Ar represents an aromatic ring group or heteroaromatic ring group;
- Y represents —OR, —SR, nitro, amino or halogen atom;
- R represents hydrogen atom, alkyl, alkenyl, alkynyl, cycloalkyl, piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, morpholyl, aralkyl, aryl, heteroaryl, acyl, —C(═O)N(R2)(R3), —Si(R4)(R5)(R6), —B(R7)(R8), —S(═O)2(R9), Or —P(═O)(R10)(R11);
- wherein R2 to R11, independently of one another, represent hydrogen atom, hydroxy, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, alkoxy, aryloxy or amino;
- and among R2 to R11, two adjacent groups may be bonded together to form a ring;
- if m and/or n is 2 or more, plural Y groups may be identical to or different from each other, and adjacent Y groups may be bonded together to form a ring;
- in addition, any of hydrogen atoms on carbons of a benzene ring may be optionally substituted with at least one substituent selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, halogen atom, hydroxyl, nitro and amino.
A process for producing an aryloyl(oxy or amino)pentafluorosulfanylbenzene compound represented by the general formula (A-I), the process comprising a step of:
- reacting, in the presence of a base, a pentafluorosulfanylbenzene compound represented by general formula (A-II):
- wherein,
- Z represents —O— or —NH—;
- n is an integer of 1 to 3;
- in addition, any of hydrogen atoms on carbons of a benzene ring may be optionally substituted with at least one substituent selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, halogen atom, hydroxyl, nitro and amino;
- with a compound represented by general formula (A-III):
- wherein,
- m, p, q, Ar and Y each represent the meanings as defined for formula (A-I);
- X represents a group selected from halogen atom, hydroxy, optionally substituted nitrophenoxy, optionally substituted nitro benzoyloxy, azide group (—N3), pivaloyloxy, 1-imidazolyl, 1-triazolyl, and 1-tetrazolyl, and if R is alkyl, alkenyl, alkynyl or aralkyl, X may also represents alkyloxy, alkenyloxy, alkynyloxy or aralkyloxy.
A process for producing an aryloyl(oxy or amino)pentafluorosulfanylbenzene compound represented by the general formula (I), the process comprising a step of:
- reacting, in the presence of a base, a pentafluorosulfanylbenzene compound represented by general formula (II):
- wherein,
- Z represents —O— or —NH—;
- n is an integer of 1 to 3;
- in addition, any of hydrogen atoms on carbons of a benzene ring may be optionally substituted with at least one substituent selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, halogen atom, hydroxyl, nitro and amino;
- with a compound represented by general formula (III):
- wherein,
- m, p, and R each represent the meanings as defined for formula (I);
- X represents a group selected from halogen atom, hydroxy, optionally substituted nitrophenoxy, optionally substituted nitro benzoyloxy, azide group (—N3), pivaloyloxy, 1-imidazolyl, 1-triazolyl, and 1-tetrazolyl, and if R is alkyl, alkenyl, alkynyl or aralkyl, X may also represents alkyloxy, alkenyloxy, alkynyloxy or aralkyloxy.
Dependencies are inferred from the claim text.