Aryloyl(oxy or amino)pentafluorosulfanylbenzene compound, pharmaceutically acceptable salt thereof, and prodrugs thereof

Patent metadata

Field	Value
Publication number	US-9682931-B2
Application number	US-201415032015-A
Country	US
Kind code	B2
Filing date	Nov 4, 2014
Priority date	Nov 1, 2013
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

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.

First claim

The invention claimed is:

1. A pharmaceutical composition comprising an aryloyl(oxy or amino)pentafluorosulfanylbenzene compound represented by general formula (I), a pharmaceutically acceptable salt thereof or a prodrug thereof:

wherein,
p 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—;
R represents hydrogen atom, alkyl, alkenyl, alkenyl, cycloalkyl, piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, morpholyl, aralkyl, aryl, heteroaryl, acyl, —C(═O)N(R 2 )(R 3 ), —Si(R 4 )(R 5 )(R 6 ), —B(R 7 )(R 8 ), —S(═O) 2 (R 9 ), or —P(═O)(R 10 )(R 11 );
wherein R 2 to R 11 independently of one another, represent hydrogen atom, hydroxy, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, alkoxy, aryloxy or amino; and among R 2 to R 11 , two adjacent groups may be bonded together to form a ring;
if m and/or n is 2 or more, plural R groups may be identical to or different from each other, and adjacent R 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.

2. The pharmaceutical composition according to claim 1 , wherein the aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is at least one selected from the group consisting of:
Compound 1: 4-benzoylaminopentafluorosulfanylbenzene
Compound 2: 4-(3,4,5-tribenzyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 3: 4-(3,4,5-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 4: 4-(3,4-diacetoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 5: 4-(3,4-dihydroxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 6: 4-(3,4,5-tribenzyloxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 7: 4-(3,4,5-trihydroxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 8: 3-(3,4,5-trihydroxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 9: 4-(3,4,5-triacetoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 10: 3-(3,4,5-tribenzyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 11: 3-(3,4,5-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 12: 3-(3,4,5-trihydroxybenzoylamino)-4-hydroxypentafluorosulfanylbenzene,
Compound 13: 3,4-bis(3,4,5-tribenzyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 14: 3,4-bis(3,4,5-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 15: 4-hydroxy-3,5-bis(3,4,5-tribenzyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 16: 4-hydroxy-3,5-bis(3,4,5-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 17: 4-(3,4,5-tribenzyloxybenzoylamino)-3-(3,4,5-tribenzyloxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 18: 4-(3,4,5-trihydroxybenzoylamino)-3-(3,4,5-trihydroxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 19: 4-(3,4-methylenedioxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 20: 4-(4-acetoxy-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 21: 4-(4-hydroxy-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 22: 4-(3,4-diacetoxycinnamoyloxy)pentafluorosulfanylbenzene,
Compound 23: 4-(2,4,6-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 24: 4-(3,4,5-trihydroxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 25: 4-(3,4,5-triacetoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 26: 4-(3,5-bis(3-methyl-2-butenyloxy)benzoylamino)pentafluorosulfanylbenzene,
Compound 27: 4-(4-(3-methyl-2-butenyloxy)-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 28: 4-(4-(2-propenyloxy)-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 29: 4-(2,3,4-tris(3-methyl-2-butenyloxy)benzoylamino)pentafluorosulfanylbenzene,
Compound 30: 4-(4-hydroxy-5-(2-propenyl)-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 34: 4-(4-(3-methyl-2-butenyloxy)-3-methoxybenzoyloxy)pentafluorosulfanylbenzene,
Compound 35: 4-(cinnamoylamino)pentafluorosulfanylbenzene,
Compound 36: 4-(cinnamoyloxy)pentafluorosulfanylbenzene,
Compound 37: 4-(4-(3-methyl-2-butenyloxy)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 38: 4-(4-(2-propenyloxy)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 39: 4-(3,4-bis(3-methyl-2-butenyloxy)cinnamoylamino)pentafluorosulfanylbenzene,
Compound 40: 4-(2,4-bis(3-methyl-2-butenyloxy)cinnamoylamino)pentafluorosulfanylbenzene,
Compound 41: 4-(3-(3-methyl-2-butenyloxy)-4-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 42: 4-(4-(2-butenyloxy)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 43: 4-(4-(3-methyl-2-butenyloxy)-3,5-dimethoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 44: 4-(4-(1-methyl-2-propenyloxy)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 45: 4-(4-hydroxy-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 46: 4-(4-hydroxy-5-(2-propenyl)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 47: 4-(4-hydroxy-5-(2-butenyl)-3-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 48: 4-(3-(1,1-dimethyl-2-propenyloxy)benzoylamino)pentafluorosulfanylbenzene,
Compound 49: 4-(2,3,4-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 50: 4-(3,5-dihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 51: 4-(2,4-dihydroxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 52: 4-(3-hydroxy-4-methoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 53: 4-(4-hydroxy-3,5-dimethoxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 54: 4-(2,3,4-tripropenyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 55: 4-(2,4,6-trihydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 56: 4-(3,4-dihydroxycinnamoylamino)pentafluorosulfanylbenzene,
Compound 57: 4-(4-hydroxy-3-fluorobenzoylamino)pentafluorosulfanylbenzene,
Compound 58: 4-(3-hydroxy-4-fluorobenzoylamino)pentafluorosulfanylbenzene,
Compound 59: 4-(4-nitro-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 60: 4-(4-amino-3-methoxybenzoylamino)pentafluorosulfanylbenzene,
Compound 61: 4-(4-aminobenzoylamino)pentafluorosulfanylbenzene,
Compound 62: 4-(4-nitrobenzoylamino)pentafluorosulfanylbenzene,
Compound 63: 4-(4-aminobenzoylamino)pentafluorosulfanylbenzene hydrochloride salt,
Compound 64: 4-(3-allyloxybenzoylamino)pentafluorosulfanylbenzene,
Compound 65: 4-(3-hydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 93: 4-(2-allyl-3-hydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 94: 4-(4-allyl-3-hydroxybenzoylamino)pentafluorosulfanylbenzene,
Compound 95: 4-(2,4,6-tris(3-methyl-2-butenyloxy)benzoylamino)pentafluorosulfanylbenzene,
Compound 96: 4-(4-(1,1-dimethyl-2-propenyloxy)-3-fluorobenzoylamino)pentafluorosulfanylbenzene,
Compound 97: 4-(4-hydroxy-3-fluoro-5-(3-methyl-2-butenyl)benzoylamino)pentafluorosulfanylbenzene,
Compound 98: 4-(4-(1,1-dimethyl-2-propenyloxy)-3-fluoro-cinnamoylamino)pentafluorosulfanylbenzene, and
Compound 99: 4-(4-hydroxy-3-fluoro-5-(3-methyl-2-butenyl)cinnamoylamino)pentafluorosulfanylbenzene.

Assignees

• Ube Industries

Inventors

• Nishino Shigeyoshi
• Shima Hidetaka
• Oda Hiroyuki
• Shimano Tetsuro

Classifications

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P9/12

  Antihypertensives · CPC title

• A61P3/06

  Antihyperlipidemics · CPC title