IP Library Granted Patent US 7,355,064
Granted Patent B2
US 7,355,064 · App. 11/703,098 · Granted Apr 8, 2008

Method for preparing 15-keto-prostaglandin E derivative

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Quick Facts
Patent No.
US 7,355,064
App. No.
11/703,098
Granted
Apr 8, 2008
Kind
B2
Abstract

Disclosed is an improved method for preparing 15-keto-prostaglandin E derivative. According to the invention, the deprotection of protected hydroxy group required in manufacturing a 15-keto-prostaglandin derivative is conducted under the presence of a phosphoric acid compound.

Claims (16)

1. A method for preparing a 15-keto-prostaglandin E derivative represented by formula (I):

wherein,

R 1 is a saturated or unsaturated bivalent lower or medium aliphatic hydrocarbon residue, which unsubstituted or substituted with halogen, lower alkyl, hydroxy, oxo, aryl or heterocyclic, and at least one of carbon atom in the aliphatic hydrocarbon is optionally substituted by oxygen, nitrogen or sulfur;

R 2 is a saturated or unsaturated lower or medium aliphatic hydrocarbon, which is unsubstituted or substituted with lower alkyl, lower alkoxy, lower alkanoyloxy, cyclo(lower)alkyl, cyclo(lower)alkyloxy, aryl, aryloxy, heterocyclic or heterocyclicoxy group; cyclo(lower)alkyl; cyclo(lower)alkyloxy; aryl; aryloxy; heterocyclic; or heterocyclicoxy group;

B is —CH 2 —CH 2 —, —CH=CH— or —C═C—;

Q is —CH 3 , —COCH 3 , —OH, —COOH or a salt, ether, ester or amide thereof;

X 1 and X 2 are hydrogen, lower alkyl, or halogen;

which comprises the step of hydrolyzing the compound represented by formula (II):

wherein,

A 1 is a protecting group for hydroxy group, R 1 , R 2 , B, Q, X 1 and X 2 are the same as above in the presence of phosphoric acid compound.

2. The method of claim 1 , wherein at least one of X 1 and X 2 is halogen.

3. The method of claim 1 , wherein both of X 1 and X 2 are halogen.

4. The method of claim 1 , wherein X 1 and X 2 are fluorine.

5. The method of claim 1 , wherein the phosphoric acid compound is phosphoric acid.

6. The method of claim 1 , wherein said step is conducted at a temperature from about 0° C. to 35° C.

7. The method of claim 1 , wherein the reaction time of said step is about 1 to 6 hours.

Assignments (11)
SECURITY INTEREST Recorded Oct 28, 2025
From: STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 072700/0001 →
RELEASE OF SECURITY INTEREST Recorded Aug 14, 2025
From: ACQUIOM AGENCY SERVICES LLC
To: SPECGX LLC; MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; OCERA THERAPEUTICS LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
Reel/Frame 072324/0740 →
SECURITY INTEREST Recorded Aug 1, 2025
From: STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
To: COMPUTERSHARE TRUST COMPANY, NATIONAL ASSOCIATION
Reel/Frame 071913/0691 →
RELEASE OF PATENT SECURITY INTERESTS RECORDED AT REEL 060434, FRAME 0536 Recorded Nov 16, 2023
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; VTESSE LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; SUCAMPO PHARMA AMERICAS LLC
Reel/Frame 065601/0347 →
RELEASE OF SECURITY INTERESTS IN PATENTS AT REEL 060389/FRAME 0913 Recorded Nov 15, 2023
From: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
To: OCERA THERAPEUTICS LLC (F/K/A OCERA THERAPEUTICS, INC.); MALLINCKRODT LLC; MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 065583/0465 →
SECURITY INTEREST Recorded Nov 15, 2023
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; OCERA THERAPEUTICS LLC; SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
To: ACQUIOM AGENCY SERVICES LLC
Reel/Frame 065595/0376 →
NOTICE OF GRANT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 22, 2022
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 060434/0536 →
SECURITY INTEREST Recorded Jun 17, 2022
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 060389/0913 →
PARTIAL ASSIGNMENT Recorded Dec 9, 2009
From: R-TECH UENO, LTD.
To: SUCAMPO AG
Reel/Frame 023620/0741 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2009
From: UENO, RYUJI
To: R-TECH UENO, LTD.
Reel/Frame 022813/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2007
From: HIRATA, RYU; MATSUKAWA, TATSUYA
To: R-TECH UENO, LTD.
Reel/Frame 018966/0210 →