IP Library Granted Patent US 9,567,363
Granted Patent B2
US 9,567,363 · App. 14/584,437 · Granted Feb 14, 2017

Certain compounds, compositions and methods

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Quick Facts
Patent No.
US 9,567,363
App. No.
14/584,437
Granted
Feb 14, 2017
Kind
B2
Abstract

The present invention provides certain tetrahydrouridine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of making and using such compounds.

Claims (23)

1. A method of producing compound 1a:

or a pharmaceutically salt thereof;

comprising reducing compound 25:

to produce compound 1a:

or a pharmaceutically salt thereof.

2. The method of claim 1 , further comprising a step of purifying the final product by preparative HPLC.

3. The method of claim 1 , wherein the reduction is carried out in the presence of sodium borohydride.

4. A method of producing compound 1a:

or a pharmaceutically salt thereof;

comprising the steps of:

(a) hydrogenating compound 24:

to produce compound 25:

and

(b) reducing compound 25 to produce compound 1a:

or a pharmaceutically salt thereof.

5. The method of claim 4 , further comprising a step of purifying the final product by preparative HPLC.

6. The method of claim 4 , wherein step (a) is carried out in the presence of rhodium on alumina.

7. The method of claim 4 , wherein step (b) is carried out in the presence of sodium borohydride.

8. A crystalline form of compound 1a:

9. The crystalline form of compound 1a of claim 8 , having a primitive trigonal cell with dimensions:

a=9.78961(18) Å

c=20.4588(7) Å

V=1698.02(7) Å.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2024
From: OTSUKA PHARMACEUTICAL CO., LTD.
To: TAIHO PHARMACEUTICAL CO., LTD.
Reel/Frame 067982/0320 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 037550 FRAME: 0224. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 25, 2016
From: OTSUKA PHARMACEUTICAL CO., LTD.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 037582/0111 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2016
From: HAMILTON, GREGORY S.; TSUKAMOTO, TAKASHI; FERRARIS, DANA V.; DUVALL, BRIDGET; LAPIDUS, RENA
To: MGI PHARMA, INC.
Reel/Frame 037543/0639 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2016
From: MGI PHARMA, INC.
To: EISAI CORPORATION OF NORTH AMERICA
Reel/Frame 037544/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2016
From: EISAI CORPORATION OF NORTH AMERICA
To: EISAI INC.
Reel/Frame 037547/0034 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2016
From: EISAI INC.
To: OTSUKA PHARMACEUTICAL CO., LTD.
Reel/Frame 037550/0224 →