Urea-based ice recrystallization inhibitor compounds and compositions, and uses thereof for cryopreservation

A compound of formula (I):

• its enantiomer, diastereomer, or its physiologically acceptable salt thereof, wherein
• A) R1 is selected from the group consisting essentially of:
• a) an unmodified C1-8 alkyl;
• b) a heteroatom-modified C1-8 alkyl;
• and
• c)
• wherein R11 and R12 are selected from the group consisting essentially of:
• a. H;
• b. an unmodified C1-4-alkyl;
• c. a heteroatom-modified C1-4-alkyl;
• d. an unmodified C1-4-alkoxy;
• e. a heteroatom-modified C1-4-alkoxy;
• f. —N(Ra)2, wherein Ra is selected from the group consisting essentially of:
• i. H;
• ii. an unmodified C1-4-alkyl;
• iii. a heteroatom-modified C1-4-alkyl;
• iv. an unmodified aryl;
• and
• v. a heteroatom-modified aryl;
• g. —C(═O)Rb, wherein Rb is selected from the group consisting essentially of:
• i. H;
• ii. an unmodified C1-4-alkyl;
• iii. a heteroatom-modified C1-4-alkyl;
• iv. an unmodified aryl;
• and
• v. a heteroatom-modified aryl;
• and
• h. —CO2Rc, wherein Rc is selected from the group consisting essentially of:
• i. H;
• ii. an unmodified C1-4-alkyl;
• iii. a heteroatom-modified C1-4-alkyl;
• iv. an unmodified aryl;
• v. a heteroatom-modified aryl;
• i. an aldehyde;
• j. a halogen;
• k. —CH3;
• l. isopropyl;
• m. trifluoromethyl;
• n. tert-butyl;
• o. —C(═O)OCH3;
• p. —OCH3;
• q. —CH2—OH;
• r. —F, —Cl;
• and
• s. —Br,
• B) R2 and R3 are selected from the group consisting essentially of:
• a) a connected three to eight membered unmodified carbon ring that includes the nitrogen atom to which R2 and R3 are bonded;
• b) a connected three to eight membered heteroatom-modified carbon ring that includes the nitrogen atom to which R2 and R3 are bonded;
• and
• c) R3 being H, and R2 being
• wherein
• a. n is from 1 to 7,
• b. R21 is selected from the group consistently essentially of:
• i. H;
• ii. —OH;
• and
• iii. —CH2OH,
• c. R22 is selected from the group consistently essentially of:
• i. H;
• ii. —OH;
• iii. —CH2OH;
• iv. an unmodified C1-3-alkyl;
• and
• v. a heteroatom-modified C1-3-alkyl, and
• d. X is selected from the group consisting essentially of:
• i. —ORd, wherein R22 on the carbon atom attached to X is hydrogen and Rd is selected from the group consisting essentially of:
• 1. —H;
• 2. a C1-3-alkyl;
• and
• 3. —CH2—CH2OH;
• ii. —N(Re)2, wherein R22 on the carbon atom attached to X is hydrogen and Re is selected from the group consisting essentially of:
• 1. —H;
• 2. a C1-3-alkyl;
• and
• 3. —CH2—CH2OH;
• iii. —CO2H;
• and
• iv. an aryl, wherein R22 on the carbon atom attached to X is hydrogen.