Disclosed herein is a novel process for preparing Compound A free base, 5-((2,4-diaminopyrimidin-5-yl)oxy)-4-iso-propyl-2-methoxybenzenesulfonamide, and a citrate salt of Compound A with simplified chemistry and a high overall yield: Compound A. In one embodiment, the overall yield from the starting material 2-isopropylphenol to Compound A citrate salt is greater than 50%. In another embodiment, the overall yield is greater than 60%. Also disclosed herein are novel salts and solvates of Compound A.

Disclosed herein is a novel process for preparing Compound A free base, 5-((2,4-diaminopyrimidin-5-yl)oxy)-4-iso-propyl-2-methoxybenzenesulfonamide, and a citrate salt of Compound A with simplified chemistry and a high overall yield: Compound A. In one embodiment, the overall yield from the starting material 2-isopropylphenol to Compound A citrate salt is greater than 50%. In another embodiment, the overall yield is greater than 60%. Also disclosed herein are novel salts and solvates of Compound A.

There is provided a fluorine-containing ether compound represented by the following formula. R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—OCH.sub.2CH(OH)CH.sub.2O—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5 (in the formula, R.sup.3 represents a perfluoropolyether chain; R.sup.2 and R.sup.4 represent a divalent linking group having a polar group and may be the same or different from each other; R.sup.1 and R.sup.5 represent a terminal group bonded to an oxygen atom of R.sup.2 or R.sup.4 and may be the same or different from each other; and at least one of R.sup.1 and R.sup.5 is an organic group having 1 to 8 carbon atoms and at least one of hydrogens included in the organic group is substituted by a cyano group).

A fluorine-containing ether compound represented by a formula (1) shown below.

R.sup.1—(O(CH.sub.2).sub.a).sub.b-[A]-[B]—O—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

(In the formula (1), R.sup.1 is an alkyl group which may have a substituent, or an organic group having at least one double bond or triple bond. Further, a represents an integer of 2 to 4, and b is 0 or 1. [A] is represented by a formula (2): —(OCH.sub.2CH(OH)CH.sub.2).sub.c— (wherein c is 1 or 2). [B] is represented by a formula (3): —(O(CH.sub.2).sub.eCH(OH)CH.sub.2).sub.d— (wherein d is 0 or 1, and e represents an integer of 2 to 4). However, the sum of c in the formula (2) and d in the formula (3) is 2. R.sup.2 is a perfluoropolyether chain. R.sup.3 is represented by a formula (4): —(OCH.sub.2CH(OH)CH.sub.2).sub.2—O—CH.sub.2(CH.sub.2).sub.fOH (wherein f represents an integer of 2 to 5).

Provided is a calixarene compound represented by structural formula (1). In structural formula (1), R.sup.1 and R.sup.2 each independently represent a structural moiety (A) having a functional group (I), a structural moiety (B) having a functional group (II) having a carbon-carbon unsaturated bond (excluding maleate groups), a structural moiety (C) having both the functional group (I) and the functional group (II), a monovalent organic group (D) that has 1 to 20 carbon atoms and is other than the structural moieties (A), (B) and (C), or a hydrogen atom (E). At least one of a plurality of R.sup.2s is the structural moiety (A), the structural moiety (B), the structural moiety (C), or the organic group (D).

##STR00001##

Provided is a calixarene compound represented by structural formula (1). In structural formula (1), R.sup.1 and R.sup.2 each independently represent a structural moiety (A) having a functional group (I), a structural moiety (B) having a functional group (II) having a carbon-carbon unsaturated bond (excluding maleate groups), a structural moiety (C) having both the functional group (I) and the functional group (II), a monovalent organic group (D) that has 1 to 20 carbon atoms and is other than the structural moieties (A), (B) and (C), or a hydrogen atom (E). At least one of a plurality of R.sup.2s is the structural moiety (A), the structural moiety (B), the structural moiety (C), or the organic group (D).

##STR00001##

The present invention relates to new classes of odorous 3-(2- methylenealkoxy)alkanenitrile derivatives of formula (I) which are useful as fragrance or flavor materials in particular in providing dry, woody, dusty, earthy, and/or patchouli notes together with optional coriander, aldehydic, citrus, mandarin, pear, cinnamon, and/ or petal floral-like notes to perfume, aroma or deodorizing/masking compositions.

Provided is a fluorine-containing ether compound that can be suitably used as a material for a lubricant for a magnetic recording medium, capable of forming a lubricant layer having excellent chemical substance resistance and wear resistance even when the thickness is small. A fluorine-containing ether compound represented by the following formula (1):
R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) In the formula (1), R.sup.3 is a perfluoropolyether chain. R.sup.2 and R.sup.4 are divalent linkage groups having a polar group, and may be the same or different. R.sup.1 and R.sup.5 are terminal groups bonded to R.sup.2 or R.sup.4, which may be the same or different, and at least one of R.sup.1 and R.sup.5 is an organic group having 1 to 8 carbon atoms wherein one or more hydrogen atoms of the organic group is substituted with a cyano group.

Provided is a fluorine-containing ether compound that can be suitably used as a material for a lubricant for a magnetic recording medium, capable of forming a lubricant layer having excellent chemical substance resistance and wear resistance even when the thickness is small. A fluorine-containing ether compound represented by the following formula (1):
R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) In the formula (1), R.sup.3 is a perfluoropolyether chain. R.sup.2 and R.sup.4 are divalent linkage groups having a polar group, and may be the same or different. R.sup.1 and R.sup.5 are terminal groups bonded to R.sup.2 or R.sup.4, which may be the same or different, and at least one of R.sup.1 and R.sup.5 is an organic group having 1 to 8 carbon atoms wherein one or more hydrogen atoms of the organic group is substituted with a cyano group.

The present disclosure generally relates to compounds useful as immunomodulators. Provided herein are compounds, compositions comprising such compounds, and methods of their use. The disclosure further pertains to pharmaceutical compositions comprising at least one compound according to the disclosure that are useful for the treatment of various diseases, including cancer and infectious diseases.