The present invention relates to novel mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yppyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, a novel crystalline form thereof, and a process for preparing the same. More specifically, the present invention relates to mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, which is excellent in stability, solubility, and bioavailability when it is administered not only alone but also in combination with other drugs and which has a high purity, a crystalline form thereof, and a process for preparing the same.

The present invention is directed to substituted aza-bicyclic imidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by TRP M8, including for example, inflammatory pain, inflammatory hyperalgesia, inflammatory hypersensitivity condition, neuropathic pain, neuropathic cold allodynia, inflammatory somatic hyperalgesia, inflammatory visceral hyperalgesia, cardiovascular disease aggravated by cold and pulmonary disease aggravated by cold.

The present invention is directed to substituted aza-bicyclic imidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by TRP M8, including for example, inflammatory pain, inflammatory hyperalgesia, inflammatory hypersensitivity condition, neuropathic pain, neuropathic cold allodynia, inflammatory somatic hyperalgesia, inflammatory visceral hyperalgesia, cardiovascular disease aggravated by cold and pulmonary disease aggravated by cold.

A process for manufacturing of an alkanesulfonic acid, and an alkanesulfonic acid manufactured by the process. Aspects of the process may involve manufacturing an alkanesulfonic acid by reaction of an initiator composition with an alkane and sulfur trioxide by preparing an initiator composition by reacting aqueous hydrogen peroxide with alkanesulfonic acid and/or H.sub.2SO.sub.4; and reacting the initiator composition with sulfur trioxide and alkane to form an alkanesulfonic acid, wherein an alkane with a purity of at least 98.0 mol-% is used.

A process for manufacturing of an alkanesulfonic acid, and an alkanesulfonic acid manufactured by the process. Aspects of the process may involve manufacturing an alkanesulfonic acid by reaction of an initiator composition with an alkane and sulfur trioxide by preparing an initiator composition by reacting aqueous hydrogen peroxide with alkanesulfonic acid and/or H.sub.2SO.sub.4; and reacting the initiator composition with sulfur trioxide and alkane to form an alkanesulfonic acid, wherein an alkane with a purity of at least 98.0 mol-% is used.

Provided herein are improved processes for the preparation of a compound of Formula IX (AG-10). Also provided herein are pharmaceutically acceptable salts of Formula I and Formula Ib

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as well as crystalline types of Formula IX (AG-10). The processes described herein provide improved yields and efficiency, while the pharmaceutically acceptable salts and crystalline forms provide unexpected pharmacokinetic properties. Other features and aspects of the present disclosure will be apparent to a person of skill in the art upon reading the remainder of the specification.

Provided herein are improved processes for the preparation of a compound of Formula IX (AG-10). Also provided herein are pharmaceutically acceptable salts of Formula I and Formula Ib

##STR00001##

as well as crystalline types of Formula IX (AG-10). The processes described herein provide improved yields and efficiency, while the pharmaceutically acceptable salts and crystalline forms provide unexpected pharmacokinetic properties. Other features and aspects of the present disclosure will be apparent to a person of skill in the art upon reading the remainder of the specification.

A salt having a group represented by formula (a): ##STR00001## wherein X.sup.a and X.sup.b each independently represent an oxygen atom or a sulfur atom, X.sup.1 represents a divalent group having an alicyclic hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and where a hydrogen atom may be replaced by a hydroxy group or a fluorine atom, and * represents a binding site.

A salt having a group represented by formula (a): ##STR00001## wherein X.sup.a and X.sup.b each independently represent an oxygen atom or a sulfur atom, X.sup.1 represents a divalent group having an alicyclic hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and where a hydrogen atom may be replaced by a hydroxy group or a fluorine atom, and * represents a binding site.

7-(3-Aminomethyl-4-methoxyiminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid methanesulfonate and hydrates thereof, processes for their preparation, pharmaceutical compositions comprising them, and their use in antibacterial therapy.