Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-02-14
2002-02-19
Dentz, Bernard (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S299000, C514S300000, C546S112000, C546S113000, C546S118000, C546S119000
Reexamination Certificate
active
06348474
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel sulfonamide compounds. More particularly, the present invention relates to novel sulfonamide compounds and salts thereof having hypoglycemic activity or PDE-V inhibitory activity. Moreover, the present invention relates to a method for producing the above-mentioned sulfonamide compound and salts thereof. The present invention also relates to pharmaceutical compositions comprising the above-mentioned sulfonamide compound or a salt thereof as an active ingredient.
BACKGROUND OF THE INVENTION
The present invention aims at providing novel sulfonamide compounds, pharmaceutically acceptable salts thereof and pharmaceutical preparations comprising the above-mentioned sulfonamide compound or a pharmaceutically acceptable salt thereof as an active ingredient, which can be used for the prophylaxis and treatment of impaired glucose tolerance disorder, diabetes (e.g., type II diabetes), diabetic complications (e.g, diabetic gangrene, diabetic arthropathy, diabetic bone resorption, diabetic glomerulosclerosis, diabetic nephropathy, diabetic dermatopathy, diabetic neuropathy, diabetic cataract, diabetic retinopathy and the like), insulin resistant syndrome (e.g., insulin receptor disorders, Rabson-Mendenhall syndrome, leprechaunism, Kobberling-Dunnign syndrome, Seip syndrome, Lawrence syndrome, Cushing syndrome, acromegaly and the like), polycystic ovary syndrome, hyperlipideria, atherosclerosis, cardiovascular disorders (e.g., stenocadia, cardiac fildure and the like), hyperglycemia (e.g., those characterrred by abnormal saccharometabolism such as feeding disorders), hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy (e.g., diabetic glomerulosclerosis), tubulointerstitial disorders (e.g, kidney diseases induced by FK506, cyclosporine and the like), renal failure, angiostenosis (e.g, after percutaneous arterioplasty), distal angiopathy, cerebral apoplexy, chronic reversible obstructions (e.g, bronchitiss, asthma inclusive of chronic asthma and allergic asthma), autoimmune diseases, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility (e.g., hypersensitive enteropathy), impotence (e.g., organic impotence, psychic impotence and the like), nephritis, cancer cachexia or restenosis after PTCA, pancreatitis, cachexia (e.g., progressive weight loss due to lipolysis, myolsis, anemia, edema, anorexia and the like in chronic diseases such as cancer, tuberculosis, endocrine diseases and AIDS), and the like.
SUMMARY OF THE INVENTION
The novel sulfonamide compound of the present invention has the following formula (I):
R
1
—SO
2
NHCO—A—X—R
2
(I)
wherein
R
1
is an optionally substituted allyl, an optionally substituted alkenyl, an optionaly substituted alkynyl, an optionally substituted cyclo(lower)alkyl, an optionally substituted aryl or an optionally substituted hetercyic group;
A is an optionally substituted heterxpolycyclic group except benzimidazolyl, indolyl, 4,7-dihydrobenzimidazolyl and 2,3-dihydrobenzoxazinyl;
X is an alkylene, an oxa, an oxa(lower)alkylene, a lower alkyleneoxa, a carbonyl, a lower alkenylene, an optionally substituted imino, an optionally N-substituted imino(lower)alkylene, an optionally N-substituted lower alkyleneimino, a thioxa(lower)alyklene or a lower alkylenethioxa; and
R
2
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl;
provided that when A is 3H-imidazo[4,5-b]pyridyl substituted by lower alkyl, R
2
is an optionally substituted aryl an optionally substituted heterocylic group, or a biphenylyl substituted by a group other than tetrazolyl, and when A is quinolyl substituted by lower allyl, R
2
is an optionaly substituted aryl, an optionally substituted heterocyclic group, or a biphenylyl substituted by at least one group selected from the group consisting of alkyl, cyclo(lower)alkyl, alkenyl, alkynyl, lower alkanoyl, lower alkoxy, phenyl, heterocycle(lower)alkyl other than substituted tetrazolylmethyl, halogen, amino, substituted amino, lower alkylsulfonyl, lower alkylsulfinyl, lower alkylthio, cyano, carbamoyl, mono(lower)alkylcarbamoyl, di(lower)alkylcarbamoyl, nitro, halo(lower)alkyl, aryl(lower)alkyl, aryl(lower)alkenyl, ary(lower)alkoxy, lower alkoxy substituted by substituted amino, cyclo(lower)alkyl(lower)alkyxoy, cyclo(lower)alkyl(lower)alkyl, aryloxy(lower)alkyl, acyloxy(lower)alkyl, hydroxy(lower)alkyl, mono- or di(lower)alkylamino(lower)alkyl, aryl(lower)alkoxy(lower)alkyl, arylthio(lower)alkyl, heterocycle(lower)alkoxy, heterocycle-oxy(lower)alkyl, aryl(lower)alkythio, arylureido, lower alkoxy(lower)alkoxy, aryl(lower)alkynyl, lower alkyl substituted by optionally substituted divalent heterocyclic group and optionaly substituted heterocylic group, (hereinafter also referred to as objective compound (I)).
Preferred salts of the objective compound (I) are conventional salts that are non-toxic and acceptable for use as phamraceuticals. Examples thereof include salts of alkali metal such as sodium and potassium, salts of alkaline earth metal such as calcium and magnesium, salts with inorganic base such as ammonium salt, salts with organic amine such as triethylamine, pyridine, picoline, ethanolamine and triethanolamine, salts with inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid, salts with organic carboxylic acid such as formic acid, acetic acid, trifluoroacetic acid, maleic acid and tartaric acid, addition salts with sulfonic acid such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid, addition salts with basic amino acid such as arginine, and addition salts with acidic amino acid such as aspartic acid and glutamic acid.
The objective compound (I) and a salt thereof can be produced by the method shown by the following reaction formula.
wherein each symbol in the formula is as defined above.
The objective compound (I) and a salt thereof can be also produced by the methods shown by the following reaction formulas.
wherein R
201
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least alkynyl, aryl(lower)alkenyl, terminal nitro or terminal formyl, R
202
is an optionaly substituted aryl, an optionally substituted heterocyclic group or a substituted biphenyl, all of which having at least alkyl, aryl(lower)alkyl, terminal amino or hydroxymethyl, and other symbols are as defined above.
wherein R
203
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least terminal formyl, R
204
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least carboxy, and other symbols are as defined above.
wherein R
205
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least hydroxy(lower)alkyl, R
206
is an optionaly substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least acyloxy(lower)alkyl, and other symbols are as defined above.
wherein R
207
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least aryloxy(lower)alkyl, and other symbols are as defined above.
wherein R
208
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least protected carboxy, and other symbols are as defined above.
wherein R
209
is an optionally substituted aryl, an optionally substituted heterocyclic group or a substituted biphenylyl, all of which having at least optionally substituted amide, and other symbols are as defined above.
wherein R
210
is an optionally substituted aryl having at least a halogen atom,
is a heterocyclic group having nitrogen, R
211
is an aryl substituted b
Abe Yoshito
Hamashima Hitoshi
Hiramura Takahiro
Imoto Takafumi
Kayakiri Hiroshi
Dentz Bernard
Fujisawa Pharmaceutical Co. Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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