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US 8,198,290 B2Granted
Methoxatin derivatives
AssigneeBerry and Associates, Inc.
InventorJohn C. Hodges
Life of this patent
Estimating the term…
Abstract
The present invention provides for compounds of Formula I and II: wherein y, X, Y, Z, R1, and R2 have any of the values defined there for in the specification. The compounds of formula I are useful as reagents in the isolation and the assay of PQQ dependent enzymes. Also provided are compositions comprising compounds of Formula I and II.
Claims20
A compound of Formula I, or a salt thereof:
- wherein
- R1 and R2 are independently selected from the group consisting of H, —CH3, —C2H5, —CH2Ph, Ph, t-Bu, —CH2CH2Si(CH3)3, —CH2CCl3, —CH2═CHCH2, and —CH2CH2CN;
- X and Y are the same and are selected from the group consisting of:
- —OH, —OCH3, —OC2H5, or —OCH2Ph, or
- X and Y are taken together to form a cyclic group of —OCH2CH2O— or —OCH2CH2CH2O—, or
- X and Y are taken together to form an oxo group (═O);
- Z is H, R3-T- or R4—S—S-T-:
- T is selected from the group consisting of:
- —(CH2)n—, —(CH2)n—(OCH2CH2)m—, —(CH2)n—(OCH2CH2CH2)m—, —CH2C(═O)NHO—(CH2)n—, —CH2C(═O)NHO—(CH2)n—(OCH2CH2)m—, —CH2C(═O)NHO—(CH2)n—(OCH2CH2CH2)m—, —(CH2C(═O)NH)m—(CH2)n—, —(CH2CH2C(═O)NH)m—(CH2)n—, —(CH2)n—(NHC(═O)CH2)m—, —(CH2)n—(OCH2CH2)m—CH2NHC(O)—, and
- —(NHC(═O)CH2CH2)m—, wherein n is an integer from 2 to 12, m is an integer from 1 to 6;
- R3 is selected from the group consisting of:
- H2C═CH—,
- H2C═CHCH2O—
- HOCH2CH(OH)—, HOCH2CH(OH)CH2O—, HC≡C—, HC≡CCH2O—, (Ph)3CS—, HS—, Tr-S—, (HO)2B—, (PhO)2B—, (CH3O)2B—, CF3(CF2)f(CH2)g—, and —N3, wherein f is an integer from 1 to 11, g is 0 or an is an integer from 1 to 3;
- and
- R4 is selected from the group consisting of:
- pyridine-2-yl, 5-nitropyridin-2-yl, N3-T-, HC≡C-T-, HC≡CCH2O-T-, CF3(CF2)f(CH2)g-T-, (HO)2B-T- and
14 more elements
A compound of formula II, or a base addition salt thereof:
- wherein y is 0 or 1.
A method of synthesizing a compound of formula II, or a pyridine salt thereof:
- comprising contacting a compound of formula V
- wherein y is 0 or 1, with a mixture of about 1 to about 5 parts pyridine to one part water for at least about 2 days at 20 to 30° C.
Dependencies are inferred from the claim text.