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：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.

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：US20190135732A1

公开(公告)日：2019-05-09

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 Serv ,  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

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.