# US 2022/0033368 A1 · Method for making propenamide compound

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- Number: US 2022/0033368 A1
- Document ID: US20220033368A1
- Status: Published application
- Kind: A1
- Application number: 17/484,170
- Filed: 2021-09-24
- Published: 2022-02-03
- Earliest claimed: 2019-10-25
- Assignees: King Abdulaziz University
- Applicants: King Abdulaziz University
- Inventors: Moustafa E. EL-ARABY; Abdelsattar M. OMAR; Martin K. SAFO; Radwan S. ELHAGGAR; Tamer M. ABDELGHANY; Mostafa H. AHMED
- Web page: https://patentgrep.com/patent/US20220033368A1

## CPC

- C07D 295/108: to an acyclic saturated chain
- A61K 31/405: Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- C07C 233/40: having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
- C07D 207/06: with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 209/14: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 241/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 295/13: to an acyclic saturated chain
- C07D 307/52: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 333/24: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A61K 9/00: Medicinal preparations characterised by special physical form {(nuclear magnetic resonance contrast preparations or magnetic resonance imaging contrast preparations A61K49/18; preparations containing radioactive substances A61K51/12)}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A compound of formula (I), wherein R1 is an optionally substituted aryl or an optionally substituted heteroaryl, R2 is an optionally substituted aryl or an optionally substituted heteroaryl, and R3 is an optionally substituted alkylamino, an optionally substituted cycloalkylamino, an optionally substituted arylamino, an optionally substituted heterocyclylamino, an optionally substituted heterocyclyl, and an optionally substituted dialkylamino. A pharmaceutical composition which includes the compound of formula (I) and a pharmaceutically acceptable carrier and/or excipient. A method of treating colorectal cancer in a subject, whereby a therapeutically effective amount of the compound of formula (I) is administered to the subject.

## Claims

### Claim at position 1

1-12. (canceled)

### Claim 13

A method for making a compound of formula (I),
or a pharmaceutically acceptable salt, solvate, tautomer, or stereoisomer thereof,
wherein:
R1 is an optionally substituted aryl or an optionally substituted heteroaryl;
R2 is an optionally substituted aryl or an optionally substituted heteroaryl; and
wherein R3 is n-propylamino,
said method comprising:
subjecting an aldehyde of formula R1CHO to a condensation reaction to form a cinnamic acid compound of formula (II)
amidating the cinnamic acid compound of formula (II) with glycine, or a salt or an ester of glycine, to form a cinnamoylglycine compound of formula (III)
wherein Ra is hydrogen or an alkyl group,
cyclocondensing the cinnamoylglycine compound of formula (III) in the presence of an aldehyde of formula R2CHO to form an azlactone compound of formula IV
reacting the azlactone compound of formula (IV) with an aliphatic or aromatic amine having an R3-group to form the compound of formula (I).

### Claim 14

(canceled)

### Claim 15 (depends on 13)

The method of claim 13, wherein the compound of formula (I) is selected from the group consisting of

### Claim at position 5

16-20. (canceled)