IP Library Granted Patent US 10,683,257
Granted Patent B2
US 10,683,257 · App. 16/410,102 · Granted Jun 16, 2020

Methods and intermediates for synthesizing SK1-I

Inventors: Zaiguo Li (Little Neck, NY); Natarajan Raju (Germantown, MD); Praveen Pande (Holbrook, NY)
Assignee: Enzo Biochem, Inc.
C07C215/28C07C213/08C07C269/04C07C269/06C07D263/06C07B2200/07
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Quick Facts
Patent No.
US 10,683,257
App. No.
16/410,102
Granted
Jun 16, 2020
Kind
B2
Abstract

The invention provides methods for synthesizing the compound (2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I, and intermediate compounds used in its synthesis.

Claims (21)

1. A method for synthesizing the compound

in which R is an alkyl group, comprising the reaction steps of:

(i)

(ii)

(iii)

(iv)

wherein R is a C 1-20 alkyl group;

(v)

(vi)

and

(vii) reacting

with DIBAL in the presence of Rochelle salt, thereby obtaining

2. The method of claim 1 , wherein R is a linear alkyl group.

3. The method of claim 1 , wherein R is a branched alkyl group.

4. The method of claim 1 , wherein step (vii) comprises the substeps of:

(a) adding

to DIBAL to form a reaction mixture, and

(b) adding the reaction mixture to a solution comprising Rochelle salt.

5. The method of claim 4 , wherein R is a linear alkyl group.

6. The method of claim 5 , wherein R is a C 5 H 11 group.

7. The method of claim 4 , wherein R is a branched alkyl group.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2026
From: ENZO BIOCHEM, INC.; ENZO LIFE SCIENCES, INC.; ENZO THERAPEUTICS, INC.
To: SERAPH BIOTECH CONSULTING, LLC
Reel/Frame 075219/0465 →
RELEASE OF SECURITY INTEREST Recorded Jul 24, 2023
From: GEMINO HEALTHCARE FINANCE, LLC D/B/A SLR HEALTHCARE ABL
To: ENZO BIOCHEM, INC.; ENZO CLINICAL LABS, INC.; ENZO LIFE SCIENCES U.S. HOLDING CORP; ENZO LIFE SCIENCES, INC.
Reel/Frame 064369/0031 →
SECURITY INTEREST Recorded Apr 3, 2023
From: ENZO LIFE SCIENCES, INC.; ENZO CLINICAL LABS, INC.; ENZO BIOCHEM, INC.; ENZO LIFE SCIENCES U.S. HOLDING CORP
To: GEMINO HEALTHCARE FINANCE, LLC D/B/A SLR HEALTHCARE ABL
Reel/Frame 063239/0103 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2019
From: LI, ZAIGUO; RAJU, NATARAJAN; PANDE, PRAVEEN
To: ENZO BIOCHEM, INC.
Reel/Frame 049980/0884 →
Continuity (3)
Continuation 16169056 · Oct 24, 2018
Provisional Application 62576943 · Oct 25, 2017
Related Publication 20200131113A1 · Apr 30, 2020