公开(公告)号：US11613514B2

公开(公告)日：2023-03-28

申请号：US17155162

申请日：2021-01-22

申请人： THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES ,  University of Maryland, Baltimore

发明人： Craig Thomas ,  Carlos Zarate ,  Ruin Moaddel ,  Todd Gould ,  Panos Zanos ,  Patrick Morris

IPC分类号： C07C225/20 ,  C07C221/00 ,  C07C269/06

摘要： The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketamine (HNK) includes preparation of (R)-norketamine via chiral resolution from racemic norketamine via a chiral resolution with L-pyroglutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine hydrochloride salts.

公开(公告)号：US10919842B2

公开(公告)日：2021-02-16

申请号：US16088371

申请日：2017-03-27

申请人： The United States of America, As Represented by the Secretary, Department of Health and Human Services ,  University of Maryland

发明人： Craig Thomas ,  Carlos Zarate ,  Ruin Moaddel ,  Todd Gould ,  Panos Zanos ,  Patrick Morris

IPC分类号： C07C225/20 ,  C07C221/00 ,  C07C269/06

摘要： The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketamine (HNK) includes preparation of (R)-norketamine via chiral resolution from racemic norketamine via a chiral resolution with L-pyroglutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine hydrochloride salts.

公开(公告)号：US20230192594A1

公开(公告)日：2023-06-22

申请号：US18170048

申请日：2023-02-16

申请人： The United States of America, as Represented by the Secretary, Department of Health ,  University of Maryland, Baltimore

发明人： Craig Thomas ,  Carlos Zarate ,  Ruin Moaddel ,  Todd Gould ,  Panos Zanos ,  Patrick Morris

IPC分类号： C07C225/20 ,  C07C221/00 ,  C07C269/06

CPC分类号： C07C225/20 ,  C07C221/00 ,  C07C269/06 ,  C07B2200/13 ,  C07C2601/14 ,  C07C2601/16

摘要： The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketam-ine (HNK) includes preparation of (R)-norket-amine via chiral resolution from racemic norketamine via a chiral resolution with L-pyro-glutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hy-droxynorketamine hydrochloride salts.

公开(公告)号：US20230022767A1

公开(公告)日：2023-01-26

申请号：US17777654

申请日：2020-11-17

申请人： THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVIC ,  THE UNIVERSITY OF MARYLAND, BALTIMORE

发明人： Patrick Joseph Morris ,  Craig Joseph Thomas ,  Stephen J. Byard ,  Martin P. Wilmshurst ,  Todd Gould ,  Carlos Zarate ,  Ruin Moaddel

IPC分类号： C07C225/20

摘要： The disclosure provides salts of (2R,6R)-hydroxynorketamine (HNK), wherein the salt is with an organic acid chosen from malonic acid, salicylic acid, ethane sulfonic acid, glycolic acid, stearic acid, or capric acid, and their crystal forms.