Provided herein are solid forms comprising {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions comprising the solid forms, methods of making the solid forms and methods of their use for the treatment of various diseases and/or disorders.

An apparatus and method of coupling and decoupling a valve stem to an actuator are disclosed. In one embodiment, the actuator includes a moveable member that is coupled to the valve stem. One of the valve stem and the moveable member is a male coupling portion and the other of the valve stem and moveable member is the female coupling portion. The male coupling portion is nested within the female coupling portion. A retaining pin retains the male coupling portion with respect to the female coupling portion.

A 3-(alkylsulfonyl)pyridine-2-carboxylic acid or a salt thereof can be manufactured by comprising: a step of allowing a compound represented by formula (1-N):

##STR00001## (wherein X represents a halogen atom) to react with a compound represented by formula (2):

R.sup.2SM.sup.2(2) (wherein R.sup.2 represents a C.sub.1-8 straight-chain alkyl group, and M.sup.2 represents a hydrogen atom or an alkali metal) to give a compound represented by formula (3-N):

##STR00002## (wherein R.sup.2 and X are as defined above); a step of allowing the compound represented by formula (3-N) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-N):

##STR00003## (wherein R.sup.2 and X are as defined above); a step of reducing the compound represented by formula (6-N) in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (8-N):

##STR00004## (wherein R.sup.2 is as defined above); and a step of hydrolyzing the compound represented by formula (8-N) in the presence of a base to give a compound represented by formula (7) or a salt thereof:

##STR00005## (wherein R.sup.2 is as defined above).

A compound represented by formula (4) is produced by a step A of reacting a compound represented by formula (2):

##STR00001##

wherein R.sup.1 represents an ethyl group or the like, R represents a halogen atom or the like, n represents 0, 1, 2, or 3, and M represents potassium or the like, with thionyl chloride to obtain a compound represented by formula (1):

##STR00002##

a step B of reacting the compound represented by formula (1) with a compound represented by formula (5):

##STR00003##

wherein A.sup.1 represents a nitrogen atom or CH, R.sup.5 represents a trifluoromethyl group or the like, and m represents 1 or 2, to produce a compound represented by formula (3):

##STR00004##

or an acid salt thereof; and a step C of reacting the compound represented by formula (3) or an acid salt thereof in the presence of acid at 100 C. to 180 C. to obtain the compound represented by formula (4):

##STR00005##

A compound represented by formula (4) is produced by a step A of reacting a compound represented by formula (2):

##STR00001##

wherein R.sup.1 represents an ethyl group or the like, R represents a halogen atom or the like, n represents 0, 1, 2, or 3, and M represents potassium or the like, with thionyl chloride to obtain a compound represented by formula (1):

##STR00002##

a step B of reacting the compound represented by formula (1) with a compound represented by formula (5):

##STR00003##

wherein A.sup.1 represents a nitrogen atom or CH, R.sup.5 represents a trifluoromethyl group or the like, and m represents 1 or 2, to produce a compound represented by formula (3):

##STR00004##

or an acid salt thereof; and a step C of reacting the compound represented by formula (3) or an acid salt thereof in the presence of acid at 100 C. to 180 C. to obtain the compound represented by formula (4):

##STR00005##

Novel sulfonylhydrazide derivatives, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The sulfonylhydrazide derivative compounds, identified as FAAH inhibitors, are useful as anticancer and/or antitumor agents.

Novel sulfonylhydrazide derivatives, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The sulfonylhydrazide derivative compounds, identified as FAAH inhibitors, are useful as anticancer and/or antitumor agents.

A compound represented by formula (7) or a salt thereof can be manufactured by the following steps: a step of allowing a compound represented by formula (1-S):

##STR00001## (wherein R.sup.1 represents a C.sub.1-8 straight-chain alkyl group, and X represents a halogen atom) to react with a compound represented by formula (2):

R.sup.2SM.sup.2(2) (wherein R.sup.2 represents a C.sub.1-8 straight-chain alkyl group, and M.sup.2 represents a hydrogen atom or an alkali metal) to give a compound represented by formula (3-S):

##STR00002## (wherein R.sup.1, R.sup.2, and X are as defined above); a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S) or a salt thereof:

##STR00003## (wherein X and R.sup.2 are as defined above); and a step of reducing the compound represented by formula (6-S) or salt thereof in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (7) or a salt thereof:

##STR00004## (wherein R.sup.2 is as defined above).

The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) ##STR00001## in which X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.1, R.sup.2, R.sup.3, n have the meanings given in the descriptionto their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation.

The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) ##STR00001## in which X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.1, R.sup.2, R.sup.3, n have the meanings given in the descriptionto their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation.