Provided herein are methods of making a thiazoline anti-hyperalgesic, Compound 1, and polymorphs thereof. The methods described herein use inexpensive reagents and are capable of providing Compound 1 in commercial-scale quantities. Also provided are pharmaceutical compositions of Compound 1 suitable for human administration.

Provided herein are methods of making a thiazoline anti-hyperalgesic, Compound 1, and polymorphs thereof. The methods described herein use inexpensive reagents and are capable of providing Compound 1 in commercial-scale quantities. Also provided are pharmaceutical compositions of Compound 1 suitable for human administration.

Compounds of general formula I

##STR00001##

X.sup.1 is a CD.sub.2 group or a CT.sub.2 group; X.sup.2 is oxygen or a group (CZ.sup.1Z.sup.2).sub.n, wherein Z.sup.1 and Z.sup.2 on each occurrence independently each are hydrogen, deuterium, or tritium and n is an integer from 1 to 12; X.sup.3 is a CD.sub.2 group or a CT.sub.2 group; and R is selected from the group consisting of hydroxy, -NO.sub.2, halogen, a diazonium ion, a diazonium salt, a trialkylammonium ion, a trialkylammonium salt, a dialkoxyarene, a sulphoxide, a boronic acid, a boronic acid ester, an organotin compound, an iodonium ion, an iodonium salt, an iodonium ylide, and a sulphonate.

Compounds of general formula I

##STR00001##

X.sup.1 is a CD.sub.2 group or a CT.sub.2 group; X.sup.2 is oxygen or a group (CZ.sup.1Z.sup.2).sub.n, wherein Z.sup.1 and Z.sup.2 on each occurrence independently each are hydrogen, deuterium, or tritium and n is an integer from 1 to 12; X.sup.3 is a CD.sub.2 group or a CT.sub.2 group; and R is selected from the group consisting of hydroxy, -NO.sub.2, halogen, a diazonium ion, a diazonium salt, a trialkylammonium ion, a trialkylammonium salt, a dialkoxyarene, a sulphoxide, a boronic acid, a boronic acid ester, an organotin compound, an iodonium ion, an iodonium salt, an iodonium ylide, and a sulphonate.

The invention relates to compounds of formula (I):

##STR00001##

or a salt thereof, wherein R.sup.1, A, L, and R.sup.2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are αvβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.

The invention relates to compounds of formula (I):

##STR00001##

or a salt thereof, wherein R.sup.1, A, L, and R.sup.2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are αvβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.

The disclosure provides for methods for preparing 2-cyanoimino-1,3-thiazolidine, which is an important building block for the preparation of crop protection active ingredients and pharmaceuticals. To this end, the disclosure provides for more efficient and improved methods of preparing 2-cyanoimino-1,3-thiazolidine.

The disclosure provides for methods for preparing 2-cyanoimino-1,3-thiazolidine, which is an important building block for the preparation of crop protection active ingredients and pharmaceuticals. To this end, the disclosure provides for more efficient and improved methods of preparing 2-cyanoimino-1,3-thiazolidine.

The invention relates to compounds of formula (I):

##STR00001##

or a salt thereof, wherein R.sup.1, A, L, and R.sup.2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are v1 integrin inhibitors that are useful for treating tissue specific fibrosis.

The invention relates to compounds of formula (I):

##STR00001##

or a salt thereof, wherein R.sup.1, A, L, and R.sup.2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are v1 integrin inhibitors that are useful for treating tissue specific fibrosis.