This fluorine-containing ether compound is represented by formula (1) shown below.

R.sup.1—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

In formula (1), R.sup.2 is a perfluoropolyether chain represented by a formula (2) shown below. R.sup.1 is a terminal group that is bonded to R.sup.2 via a CH.sub.2 group, and is represented by a formula (3) shown below. R.sup.3 is bonded to R.sup.2 via a CH.sub.2 group, is a terminal group having at least one hydroxyl group, and may be the same as, or different from, R.sup.1.

—(CF.sub.2).sub.p-1—O—((CF.sub.2).sub.pO).sub.q—(CF.sub.2).sub.p-1—  (2)

In formula (2), p represents an integer of 2 to 3, and q indicates the average polymerization degree and is a number within a range from 1 to 20.

—O(CH.sub.2—CH(OH)—CH.sub.2—O).sub.2—CH.sub.2—(CH.sub.2).sub.n,—OH  (3)

In formula (3), n represents an integer of 1 to 8.

This fluorine-containing ether compound is represented by formula (1) shown below.

R.sup.1—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

In formula (1), R.sup.2 is a perfluoropolyether chain represented by a formula (2) shown below. R.sup.1 is a terminal group that is bonded to R.sup.2 via a CH.sub.2 group, and is represented by a formula (3) shown below. R.sup.3 is bonded to R.sup.2 via a CH.sub.2 group, is a terminal group having at least one hydroxyl group, and may be the same as, or different from, R.sup.1.

—(CF.sub.2).sub.p-1—O—((CF.sub.2).sub.pO).sub.q—(CF.sub.2).sub.p-1—  (2)

In formula (2), p represents an integer of 2 to 3, and q indicates the average polymerization degree and is a number within a range from 1 to 20.

—O(CH.sub.2—CH(OH)—CH.sub.2—O).sub.2—CH.sub.2—(CH.sub.2).sub.n,—OH  (3)

In formula (3), n represents an integer of 1 to 8.

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V): ##STR00001##
and/or a salt thereof, wherein R.sub.1 is —OH or —OP(O)(OH).sub.2, and X.sub.1, X.sub.2, X.sub.3, R.sub.2, R.sub.2a, R.sub.a, R.sub.b, and R.sub.c are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P.sub.1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V): ##STR00001##
and/or a salt thereof, wherein R.sub.1 is —OH or —OP(O)(OH).sub.2, and X.sub.1, X.sub.2, X.sub.3, R.sub.2, R.sub.2a, R.sub.a, R.sub.b, and R.sub.c are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P.sub.1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitis, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

The present disclosure provides a process for the preparation of compounds of formula (III),

##STR00001##

compounds of formula (V),

##STR00002##

and corresponding salts of formula (IV).

##STR00003##

The compounds made by the methods and processes of the invention are particularly useful for administration in humans and animals.

The present disclosure provides a process for the preparation of compounds of formula (III),

##STR00001##

compounds of formula (V),

##STR00002##

and corresponding salts of formula (IV).

##STR00003##

The compounds made by the methods and processes of the invention are particularly useful for administration in humans and animals.

A salt represented by formula (I): ##STR00001##
wherein R.sup.1 and R.sup.2 each independently represent a hydroxy group, —O—R.sup.10, —O—CO—O—R.sup.10 or —O-L.sup.1-CO—O—R.sup.10; L.sup.1 represents an alkanediyl group having 1 to 6 carbon atoms; R.sup.4, R.sup.5, R.sup.7 and R.sup.8 each independently represent a halogen atom, an alkyl fluoride group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH.sub.2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO.sub.2—; R.sup.10 represents an acid-labile group; X.sup.1 and X.sup.2 each independently represent an oxygen atom or a sulfur atom; m1 represents an integer of 1 to 5, m2 and m8 represent an integer of 0 to 5, m4, m5 and m7 represent an integer of 0 to 4; and AI.sup.− represents an organic anion.

Disclosed are a salt represented by formula (I), an acid generator, and a resist composition including the same:

##STR00001## wherein R.sup.1, R.sup.2 and R.sup.3 each represent a hydroxy group, *—O—R.sup.10, *—O—CO—O—R.sup.10, etc.; L.sup.10 represents an alkanediyl group; R.sup.10 represents an acid-labile group; R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each represent a halogen atom, a haloalkyl group or a hydrocarbon group; A.sup.1, A.sup.2 and A.sup.3 each represent a hydrocarbon group which may have a substituent, and —CH.sub.2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO.sub.2—; m1 represents an integer of 1 to 5, m2, m3, m8 and m9 represent an integer of 0 to 5, m4 to m7 represent an integer of 0 to 4, 1≤m1+m7≤5, 0≤m2+m8≤5, 0≤m3+m9≤5; and AI.sup.− represents an organic anion.

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V):

##STR00001##

and/or a salt thereof, wherein R.sub.1 is —OH or —OP(O)(OH).sub.2, and X.sub.1, X.sub.2, X.sub.3, R.sub.2, R.sub.2a, R.sub.a, R.sub.b, and R.sub.c are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P.sub.1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.