# US 10,479,813 B2 · Utility of nematode small molecules

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- Number: US 10,479,813 B2
- Document ID: US10479813B2
- Status: Granted
- Kind: B2
- Application number: 16/251,750
- Filed: 2019-01-18
- Published: 2019-05-23
- Granted: 2019-11-19
- Earliest claimed: 2011-08-08
- Assignees: California Institute of Technology; Boyce Thompson Institute for Plant Research, Inc.
- Applicants: California Institute of Technology; Boyce Thompson Institute for Plant Research
- Inventors: Andrea Choe; Paul W. Sternberg; Frank C. Schroeder; Stephan H. Von Reuss
- Web page: https://patentgrep.com/patent/US10479813B2

## CPC

- C07H 15/04: attached to an oxygen atom of the saccharide radical
- A01N 37/36: containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/38: condensed with carbocyclic rings
- A61K 31/454: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A61K 31/7028: Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/12: Antidiarrhoeals
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/06: Antianaemics
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- A61P 11/06: Antiasthmatics
- A61P 13/08: of the prostate
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/10: Anti-acne agents
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- C07H 15/08: Polyoxyalkylene derivatives
- C07H 15/10: containing unsaturated carbon-to-carbon bonds
- C07H 15/18: Acyclic radicals, substituted by carbocyclic rings
- C07H 15/26: Acyclic or carbocyclic radicals, substituted by hetero rings
- C07D 309/10: Oxygen atoms
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to methods of treating immune disorders and/or inflammation using certain modulator compounds. In one embodiment, the present invention provides a method of treating an immune and inflammatory disorders disorder by administering a composition comprising a therapeutically effective dosage of an ascaroside compound, or a mixture of ascaroside compounds, or a mixture containing at least one ascaroside.

## Claims

### Claim 1

A method of reducing eosinophils (eos) or lymphocytes (lym), or both, in a subject, comprising:
administering a therapeutically effective dosage of a composition to the subject, thereby reducing eos or lym, or both, in the subject,
wherein the composition comprises a pharmaceutically acceptable carrier and a compound of Formula (I)
wherein
R1 is, independently for each occurrence, hydrogen or alkyl;
R1′ is, independently for each occurrence, hydrogen or alkyl;
X is C(R1)2;
X1 is cis- or trans-C(R1)═C(R1);
n1, n2, and n3 are each independently an integer of 0 to 30, inclusive;
n4 is an integer of 1 to 30, inclusive;
the sum of n1, each n2, and each n3 is 1 to 30, inclusive;
R3 is hydrogen or alkyl;
R4 is hydrogen or alkyl;
R5′ is hydrogen, alkyl, halogen, —OR6, or —N(R6)2;
R5 is —OR6 or —N(R6)2; and
R6 is independently alkyl, alkenyl, aryl, or heteroaryl, wherein the alkyl, alkenyl, aryl, or heteroaryl is optionally substituted,
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein R3 is hydrogen.

### Claim 3 (depends on 1)

The method of claim 1, wherein R4 is hydrogen.

### Claim 4 (depends on 1)

The method of claim 1, wherein R5′ is alkyl.

### Claim 5 (depends on 1)

The method of claim 1, wherein R5 is OR6.

### Claim 6 (depends on 1)

The method of claim 1, wherein the compound of Formula (I) is a compound of Formula (Ia):
wherein
R1a is hydrogen or methyl;
n is an integer from 0 to 6, inclusive;
represents a single bond or a double bond; and
R5a is —OR6,
or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 6)

The method of claim 6, wherein R1a is methyl.

### Claim 8 (depends on 6)

The method of claim 6, wherein n is an integer from 0 to 4, inclusive.

### Claim 9 (depends on 1)

The method of claim 1, thereby reducing mucus production in the subject.

### Claim 10 (depends on 1)

The method of claim 1, wherein the subject is a human.

### Claim 11 (depends on 1)

The method of claim 1, wherein the subject is selected from primates, humans, equines, horses, cattle, cows, swine, sheep, rodents, rats, pets, dogs, and guinea pigs.

### Claim 12 (depends on 1)

The method of claim 1, wherein the method is a method of treating acne vulgaris, asthma, an autoimmune disease, celiac disease, chronic prostatitis, glomerulonephritis, hypersensitivity, inflammatory bowel disease, pelvic inflammatory disease, reperfusion injury, rheumatoid arthritis, sarcoidosis, transplant rejection, vasculitis, interstitial cystitis, lupus, scleroderma, hemolytic anemia, type one diabetes, Graves' disease, multiple sclerosis, Goodpasture's syndrome, pernicious anemia, myopathy, seasonal allergy, mastocytosis, perennial allergy, anaphylaxis, food allergy, allergic rhinitis, atopic dermatitis, or autism.

### Claim 13 (depends on 1)

The method of claim 1, wherein the method is a method of reducing eos in the subject.

### Claim 14 (depends on 1)

The method of claim 1, wherein the method is a method of reducing lym in the subject.

### Claim 15 (depends on 1)

The method of claim 1, wherein the method is a method of reducing eos and lym in the subject.

### Claim 16 (depends on 1)

The method of claim 1, wherein the method is a method of treating an inflammatory disorder, an autoimmune disorder, or both.

### Claim 17 (depends on 1)

The method of claim 1, wherein method is a method of treating asthma, inflammatory bowel disease, rheumatoid arthritis, or multiple sclerosis.