0000950123-11-025641 Sample Contracts

THE MEDICINES COMPANY Restricted Stock Agreement Granted Under Amended and Restated 2004 Stock Incentive Plan

Restricted Stock Agreement • March 15th, 2011 • Medicines Co /De • Pharmaceutical preparations • Delaware

• Contract Type
  Restricted Stock Agreement
• Filed
  March 15th, 2011
• Company
  Medicines Co /De
• Industry
  Pharmaceutical preparations
• Jurisdiction
  Delaware

THIS AGREEMENT made as of this 7th day of December, 2010, between The Medicines Company, a Delaware corporation (the “Company”) and Clive A. Meanwell, the “Participant”).

Confidential Materials omitted and filed separately with the Securities and Exchange Commission. Asterisks denote omissions. SECOND AMENDED AND RESTATED DISTRIBUTION AGREEMENT

Distribution Agreement • March 15th, 2011 • Medicines Co /De • Pharmaceutical preparations • New York

• Contract Type
  Distribution Agreement
• Filed
  March 15th, 2011
• Company
  Medicines Co /De
• Industry
  Pharmaceutical preparations
• Jurisdiction
  New York

This Second Amended and Restated Distribution Agreement (together with its schedules and exhibits, the “Agreement”) is entered into by The Medicines Company, a Delaware corporation with offices at 8 Sylvan Way, Parsippany, NJ 07054 (“MDCO”), and Integrated Commercialization Solutions, Inc., a California corporation with offices at 3101 Gaylord Parkway, Frisco, TX 75034 (the “Distributor”), effective as of October 1, 2010 (the “Effective Date”).

Confidential Materials omitted and filed separately with the Securities and Exchange Commission. Asterisks denote omissions.

Option Agreement • March 15th, 2011 • Medicines Co /De • Pharmaceutical preparations • England

• Contract Type
  Option Agreement
• Filed
  March 15th, 2011
• Company
  Medicines Co /De
• Industry
  Pharmaceutical preparations
• Jurisdiction
  England

Confidential Materials omitted and filed separately with the Securities and Exchange Commission. Asterisks denote omissions. AMENDMENT NO. 1 TO LICENSE AGREEMENT

License Agreement • March 15th, 2011 • Medicines Co /De • Pharmaceutical preparations

• Contract Type
  License Agreement
• Filed
  March 15th, 2011
• Company
  Medicines Co /De
• Industry
  Pharmaceutical preparations

THIS AMENDMENT NO. 1 (“Amendment No. 1”) TO THE AGREEMENT (as defined below) is entered into as of April 25, 2006 by and between ASTRAZENECA AB, a company incorporated under the laws of Sweden with its registered office at SE-151 85 Södertälje, Sweden (“ASTRAZENECA”) and THE MEDICINES COMPANY, a company incorporated under the laws of Delaware with its registered office at 8 Campus Drive, Parsippany, New Jersey 07054, United States (“TMC”).