The Other Cyclo In The Bicyclo Ring System Is Five-membered Patents (Class 544/280)
  • Patent number: 10815240
    Abstract: The present invention relates to a manufacturing process and intermediates for preparing a crystalline or non-crystalline form of N-((1S,3S)-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclobutyl)propane-1-sulfonamide. The present invention also relates to salt forms and pharmaceutical compositions comprising the crystalline form, and to methods for use of the compound prepared from a crystalline form in the treatment of various diseases.
    Type: Grant
    Filed: July 3, 2019
    Date of Patent: October 27, 2020
    Assignee: Pfizer Inc.
    Inventors: Kapildev Kashmirilal Arora, Jacob Cole DeForest, Andrew Kevern Hills, Brian Patrick Jones, Kris Nicole Jones, Chad Arthur Lewis, Anil Mahadeo Rane
  • Patent number: 10793572
    Abstract: Disclosed are novel compounds useful in the treatment of multiple sclerosis and other autoimmune diseases. The present invention describes compounds of formula (I) wherein: R1 is selected from H and CH3 R2 is selected from H, C4H9 alkyl, C6H13 alkyl and C3H6-phenyl, said phenyl optionally substituted by OH or OCH3, (1R,2S,5S)-5-methylcyclopent-3-ene-1,2-diol X is O or S Y is C, N or S.
    Type: Grant
    Filed: September 29, 2015
    Date of Patent: October 6, 2020
    Assignee: THE PROVOST FELLOWS FOUNDATION SCHOLARS AND THE OTHER MEMBERS OF BOARD OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH
    Inventors: John Michael Southern, Stephen J. Connon
  • Patent number: 10787457
    Abstract: The present invention provides a novel RET inhibitor comprising, as an active ingredient, a compound or a salt thereof that have not been known for their RET inhibitory activity, and also provides an agent for preventing or treating diseases (e.g., malignant tumors) that can be prevented or treated by RET inhibitory activity. The RET inhibitor comprises, as an active ingredient, a compound represented by Formula (I) below or a salts thereof: wherein A, R1 to R3, X, and n are as defined in the specification.
    Type: Grant
    Filed: November 29, 2018
    Date of Patent: September 29, 2020
    Assignee: Taiho Pharmaceutical Co., Ltd.
    Inventors: Isao Miyazaki, Tadashi Shimamura, Masanori Kato, Hidenori Fujita
  • Patent number: 10772890
    Abstract: The present invention relates to the use of myeloperoxidase inhibitors (MPO) inhibitors for the treatment of multiple system atrophy. The present invention also relates to the use of MPO inhibitors for the treatment of Huntington's disease. The present invention also relates to the use of MPO inhibitors for neuroprotection.
    Type: Grant
    Filed: August 30, 2018
    Date of Patent: September 15, 2020
    Assignee: AstraZeneca AB
    Inventors: Hakan Eriksson, Werner Poewe
  • Patent number: 10766901
    Abstract: Provided are a preparation method for a chiral pyrrolopyrimidine compound and a related intermediate. In the method, a compound of formula A and a compound of formula 6 or a salt thereof are reacted to obtain a compound of formula 7 or a compound of formula 14, and a compound of formula I is prepared from the compound of formula 7 or the compound of formula 14. Also provided are the intermediate used, a preparation method for the intermediate and a use of the intermediate in the preparation of the compound of formula I. The preparation method has characteristics such as brief steps, a high stereoselectivity, a high utilization ratio of atoms, mild reaction conditions and a convenient post-treatment. The method avoids using an expensive asymmetric reaction catalyst, and is suitable for industrial production.
    Type: Grant
    Filed: June 15, 2017
    Date of Patent: September 8, 2020
    Assignees: CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD., CENTAURUS BIOPHARMA CO., LTD.
    Inventors: Xiquan Zhang, Aiming Zhang, Zhou Zhou, Huadong Yao, Jie Xie
  • Patent number: 10759812
    Abstract: The present invention relates to a thienopyrimidine derivative and use thereof in medicine, and also to a pharmaceutical composition containing the compound. The compound or pharmaceutical composition is used for inhibiting acetyl-CoA carboxylase (ACC). The present invention also relates to a method of preparing such compound and pharmaceutical composition, as well as their use in the treatment or prevention of diseases regulated by acetyl-CoA carboxylase in mammals, especially in humans.
    Type: Grant
    Filed: January 22, 2018
    Date of Patent: September 1, 2020
    Assignee: Sunshine Lake Pharma Co., Ltd.
    Inventors: Wanjun Tang, Xinye Yang, Zheng Gu, Chenlu Li, Zongyuan Zhang, Zhifu Wan, Xiaojun Wang, Yingjun Zhang
  • Patent number: 10695337
    Abstract: The present invention provides piperidin-4-yl azetidine derivatives, as well as their compositions and methods of use, that modulate the activity of Janus kinase 1 (JAK1) and are useful in the treatment of diseases related to the activity of JAK1 including, for example, inflammatory disorders, autoimmune disorders, cancer, and other diseases.
    Type: Grant
    Filed: June 1, 2018
    Date of Patent: June 30, 2020
    Assignees: Incyte Holdings Corporation, Incyte Corporation
    Inventors: Taisheng Huang, Chu-Biao Xue
  • Patent number: 10676478
    Abstract: The present invention relates to a 7-(thiazol-5-yl)pyrrolopyrimidine compound as a TLR7 agonist, and particularly relates to a compound shown in formula (I), pharmaceutically acceptable salt and preparation method thereof, a pharmaceutical composition containing such a compound, and usage thereof in preparing an antiviral drug.
    Type: Grant
    Filed: November 4, 2016
    Date of Patent: June 9, 2020
    Assignee: CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.
    Inventors: Zhaozhong Ding, Fei Sun, Lifang Wu, Hao Wu, Shuhui Chen, Ling Yang
  • Patent number: 10640506
    Abstract: The present invention provides cyclobutyl substituted pyrrolopyrimidines and pyrrolopyridines of Formula I: wherein X, Y, Z, L, A, R5, n and m are defined above, as well as their compositions and methods of use, that modulate the activity of Janus kinases (JAKs) and are useful in the treatment of diseases related to the activity of JAKs including, for example, inflammatory disorders, autoimmune disorders, cancer, and other diseases.
    Type: Grant
    Filed: July 27, 2018
    Date of Patent: May 5, 2020
    Assignees: Incyte Holdings Corporation, Incyte Corporation
    Inventors: James D. Rodgers, Stacey Shepard, Lixin Shao, Joseph Glenn
  • Patent number: 10639310
    Abstract: The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: May 5, 2020
    Assignee: Incyte Corporation
    Inventors: James D. Rodgers, Stacey Shepard
  • Patent number: 10626118
    Abstract: The present application relates to the field of pharmaceutical chemistry. The application specifically relates to a crystal form A and crystal form B of a pyrrolopyrimidine (formula I) for preparing a JAK inhibitor. The application further relates to a method for preparing the crystal form A and crystal form B, a crystalline composition comprising the crystal form A or crystal form B, a pharmaceutical composition comprising the crystal form A, crystal form B, or crystalline composition, and a pharmaceutical application of the pharmaceutical composition, the crystal form A, and the crystal form B. The crystal form A and crystal form B of the application has the advantages of high purity, high crystallinity, and good stability.
    Type: Grant
    Filed: June 15, 2017
    Date of Patent: April 21, 2020
    Assignees: CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD., CENTAURUS BIOPHARMA CO., LTD.
    Inventors: Zhou Zhou, Aiming Zhang, Xiquan Zhang, Huadong Yao
  • Patent number: 10610530
    Abstract: The present invention provides salt forms of (R)-3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile that are useful in the modulation of Janus kinase activity and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.
    Type: Grant
    Filed: June 8, 2018
    Date of Patent: April 7, 2020
    Assignees: Incyte Corporation, Incyte Holdings Corporation
    Inventors: Hui-Yin Li, James D. Rodgers
  • Patent number: 10611765
    Abstract: Disclosed herein are novel compounds that are Mps1/TTK inhibitors. Also disclosed are compositions comprising the compounds and methods of using the compounds in treating various diseases.
    Type: Grant
    Filed: November 5, 2015
    Date of Patent: April 7, 2020
    Inventors: Robert Brueggemeier, Harold Fisk, Pui-Kai Li, Chenglong Li, Yasuro Sugimoto
  • Patent number: 10570141
    Abstract: The present invention belongs to the field of pharmaceutical chemistry, and relates to a substituted pyrrolopyrimidine CDK inhibitor, in particular to a compound as shown in formula I or a pharmaceutically acceptable salt or solvate thereof, as well as a preparation method thereof and a pharmaceutical composition thereof. The present invention also relates to the use of the compound and the pharmaceutical composition thereof in the preparation of a drug for treating diseases associated with CDK inhibition. The compound according to the present invention has a marked inhibitory effect on CDK, excellent drug absorption and significantly superior oral absorption effect.
    Type: Grant
    Filed: March 27, 2017
    Date of Patent: February 25, 2020
    Assignees: CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., CENTAURUS BIOPHARMA CO., LTD., LIANYUNGANG RUNZHONG PHARMACEUTICAL CO., LTD.
    Inventors: Shulong Wang, Kuncheng Chen, Xijie Liu, Yuandong Hu, Bo Liu, Yong Peng, Hong Luo, Yongxin Han, Shanchun Wang, Mei Liu, Hongjiang Xu
  • Patent number: 10562902
    Abstract: Disclosed are a compound related to inhibiting the activity of an IRAK4 kinase, a pharmaceutical composition thereof, a use thereof in preparing drugs, a method in which same is used for inhibiting the activity of the IRAK4 kinase and a method in which same is used for treating and/or preventing IRAK4 kinase mediated diseases or conditions in mammals (especially humans). The compound has a structural formula I.
    Type: Grant
    Filed: August 12, 2016
    Date of Patent: February 18, 2020
    Assignee: Beijing Hanmi Pharmaceutical Co., Ltd.
    Inventors: Jiangcheng Xu, Qinguan Cai, Mi Young Cha, Maengsup Kim
  • Patent number: 10472366
    Abstract: The invention relates to glucuronide prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib having formula I: where A1 and R1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.
    Type: Grant
    Filed: March 7, 2018
    Date of Patent: November 12, 2019
    Assignee: THERAVANCE BIOPHARMA R&D IP, LLC
    Inventors: Daniel D. Long, Donna A.A. Wilton, Mandy M. Loo
  • Patent number: 10420768
    Abstract: Disclosed are chemical entities of formula I: wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.
    Type: Grant
    Filed: April 24, 2018
    Date of Patent: September 24, 2019
    Assignee: Rugen Holdings (Cayman) Limited
    Inventor: Gideon Shapiro
  • Patent number: 10398699
    Abstract: The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.
    Type: Grant
    Filed: April 23, 2018
    Date of Patent: September 3, 2019
    Assignees: Incyte Holdings Corporation, Incyte Corporation
    Inventors: James D. Rodgers, Stacey Shepard
  • Patent number: 10364248
    Abstract: The present invention is related to processes for preparing 4-chloro-7H-pyrollo[2,3,-d]pyrimidine, and related synthetic intermediate compounds. 4-Chloro-7H-pyrrolo[2,3,-d]pyrimidine is an intermediate for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines, which are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.
    Type: Grant
    Filed: January 12, 2018
    Date of Patent: July 30, 2019
    Assignees: Incyte Corporation, Incyte Holdings Corporation
    Inventors: Jiacheng Zhou, James D. Rodgers, Haisheng Wang
  • Patent number: 10328080
    Abstract: In some embodiments, the invention includes a therapeutic combination of a phosphoinositide 3-kinase (PI3K) inhibitor, including PI3K inhibitors selective for the ?- and ?-isoforms and selective for both ?- and ?-isoforms, and a Bruton's tyrosine kinase (BTK) inhibitor. In some embodiments, the invention includes therapeutic methods of using a BTK inhibitor and a PI3K-? inhibitor to treat solid tumor cancers by modulation of the tumor microenvironment, including macrophages, monocytes, mast cells, helper T cells, cytotoxic T cells, regulatory T cells, natural killer cells, myeloid-derived suppressor cells, regulatory B cells, neutrophils, dendritic cells, and fibroblasts.
    Type: Grant
    Filed: December 5, 2014
    Date of Patent: June 25, 2019
    Assignee: Acerta Pharma, B.V.
    Inventors: Ahmed Hamdy, Wayne Rothbaum, Raquel Izumi, Brian Lannutti, Todd Covey, Roger Ulrich, Dave Johnson, Tjeerd Barf, Allard Kaptein
  • Patent number: 10259814
    Abstract: This invention concerns pyrrolo[3,2-d]pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treatment and/or therapy of diseases.
    Type: Grant
    Filed: October 25, 2016
    Date of Patent: April 16, 2019
    Assignee: Janssen Sciences Ireland UC
    Inventors: David Craig McGowan, Stefaan Julien Last, Serge Maria Aloysius Pieters, Werner Embrechts, Tim Hugo Maria Jonckers, Pierre Jean-Marie Bernard Raboisson
  • Patent number: 10233174
    Abstract: The invention relates to thiocarbamate prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib having formula I: wherein R1, R2, R3, R4 and n are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.
    Type: Grant
    Filed: May 22, 2018
    Date of Patent: March 19, 2019
    Assignee: THERAVANCE BIOPHARMA R&D IP, LLC
    Inventor: Daniel D. Long
  • Patent number: 10220037
    Abstract: Compounds of the general formula): processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.
    Type: Grant
    Filed: June 2, 2017
    Date of Patent: March 5, 2019
    Assignee: Pfizer Inc.
    Inventors: John Howard Tatlock, Indrawan James McAlpine, Michelle Bich Tran-Dube, Eugene Yuanjin Rui, Martin James Wythes, Robert Arnold Kumpf, Michele Ann McTigue, Ryan Patman
  • Patent number: 10167287
    Abstract: This invention provides substituted pyrimidine compounds having the formula: wherein X is absent, CH2, S, or O, and R is an alkyl group having from one to ten carbon atoms, and optionally salts, hydrates, or solvates thereof, that are useful in treating a patient having a disease or cancer. The compounds of this invention are useful as multi-enzyme antifolates selectively targeting the folate receptor (FR). Further, a method of making 5- and 6-substituted cyclopenta[d]pyrimidine for nonclassical and classical antifolates as TS and DHFR inhibitors is provided.
    Type: Grant
    Filed: April 5, 2017
    Date of Patent: January 1, 2019
    Assignee: Duquesne University of the Holy Spirit
    Inventors: Aleem Gangjee, Larry H. Matherly
  • Patent number: 10138250
    Abstract: The present invention relates to novel crystalline forms of 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (compound I), its salts, and process for preparation thereof. Crystalline forms in the present invention have good stability, low hygroscopicity, good processability, easy treatability and other favorable properties. In addition, the process is simple, low cost, and has an important value for future optimization and development of the drug.
    Type: Grant
    Filed: May 21, 2018
    Date of Patent: November 27, 2018
    Assignee: Crystal Pharmatech Co., Ltd.
    Inventors: Minhua Chen, Yanfeng Zhang, Xiaoyu Zhang
  • Patent number: 10034882
    Abstract: The present invention relates to Orally Disintegrating Tablets (ODT) of Tofacitinib and its pharmaceutically acceptable salts and the process to produce the ODT. The invention further relates to ODTs comprising Tofacitinib and its pharmaceutically acceptable salts, at least one sweetening agent, at least one disintegrant and optionally other excipients. The weight of the Orally Disintegrating tablets is 200 mg or less. The invention further relates to Orally Disintegrating Tablets of Tofacitinib Citrate.
    Type: Grant
    Filed: June 24, 2016
    Date of Patent: July 31, 2018
    Assignee: Unichem Laboratories Limited
    Inventors: Saurabh Gupta, Saiesh P. Phaldesai, Nsk. Senthil Kumar, Milind Vinayak Sathe
  • Patent number: 10016427
    Abstract: Disclosed is a compound of formula (I): crystalline forms thereof, and solvates thereof; pharmaceutical compositions comprising a pharmaceutically effective amount of the compound of formula (I), or a crystalline form thereof, or a solvate thereof, and a pharmaceutically acceptable carrier or diluent; and the use of a compound of formula (I), or a crystalline form thereof, or a solvate thereof, for treating a patient suffering from, or subject to, a pathological condition capable of being ameliorated by inhibiting an E1 activating enzyme, particularly NAE, including, e.g., cancer.
    Type: Grant
    Filed: October 9, 2015
    Date of Patent: July 10, 2018
    Assignee: Millennium Pharmacetuicals, Inc.
    Inventors: Ian G. Armitage, Reenu Chopra, Martin Ian Cooper, Marianne Langston, Steven P. Langston, Stepan Vyskocil
  • Patent number: 10016432
    Abstract: Adenosine kinase inhibitors, including pharmaceutical compositions containing the adenosine kinase inhibitors, and their use for preventing epilepsy and its progression in patients. The adenosine kinase inhibitors have the formula: where the moieties J and K, considered in combination, are —CH2—, or K and L, considered in combination, are —CH2—. The R1 moiety can be —NH2, C1-C6 alkyl, C1-C6 alkoxy, or C1-C6 hydroxyalkyl. The R2 and R3 moieties are each independently C1-C6 alkyl. The R4 moiety is hydrogen or C1-C6 alkyl. The R5 and R6 moieties are each independently C6-C12 aryl, C3-C8 cycloalkyl, or C3-C8 heteroaryl, that is optionally further substituted.
    Type: Grant
    Filed: May 26, 2017
    Date of Patent: July 10, 2018
    Assignees: Legacy Emanuel Hospital & Health Center, The United States of America, as represented by the Secretary, Department of Health and Human Services
    Inventors: Kenneth Alan Jacobson, Detlev Boison, Kiran Shambhu Toti
  • Patent number: 10016429
    Abstract: The present invention provides salt forms of (R)-3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile that are useful in the modulation of Janus kinase activity and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.
    Type: Grant
    Filed: May 25, 2016
    Date of Patent: July 10, 2018
    Assignees: INCYTE CORPORATION, INCYTE HOLDINGS CORPORATION
    Inventors: James D. Rodgers, Hui-Yin Li
  • Patent number: 9994579
    Abstract: The present invention relates to novel crystalline forms of 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-car boxylic acid dimethylamide(compound I), its salts, and process for preparation thereof. Crystalline forms in the present invention have good stability, low hygroscopicity, good processability, easy treatability and other favorable properties. In addition, the process is simple, low cost, and has an important value for future optimization and development of the drug.
    Type: Grant
    Filed: December 11, 2015
    Date of Patent: June 12, 2018
    Assignee: Crystal Pharmatech Co., Ltd.
    Inventors: Minhua Chen, Yanfeng Zhang, Kai Liu, Jiaoyang Li, Xiaoyu Zhang
  • Patent number: 9981949
    Abstract: The present invention relates to the stereospecific synthesis of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine, its salt forms, and novel polymorphic forms of these salts.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: May 29, 2018
    Assignee: Oyster Point Pharma, Inc.
    Inventors: Srinivasa Rao Akireddy, Balwinder Singh Bhatti, Timothy J. Cuthbertson, Gary Maurice Dull, Craig Harrison Miller, Joseph Pike Mitchener, Jr., Julio A. Munoz, Pieter Albert Otten
  • Patent number: 9974790
    Abstract: The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.
    Type: Grant
    Filed: November 21, 2016
    Date of Patent: May 22, 2018
    Assignees: Incyte Corporation, Incyte Holdings Corporation
    Inventors: James D. Rodgers, Stacey Shepard
  • Patent number: 9968610
    Abstract: Disclosed are chemical entities of formula I: wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.
    Type: Grant
    Filed: February 9, 2017
    Date of Patent: May 15, 2018
    Assignee: Rugen Holdings (Cayman) Limited
    Inventor: Gideon Shapiro
  • Patent number: 9963456
    Abstract: A pyrrolopyrimidine compound or a salt thereof and compositions, NAE inhibitors and anti-tumor agents containing the pyrrolopyrimidine compound or a salt thereof.
    Type: Grant
    Filed: June 24, 2015
    Date of Patent: May 8, 2018
    Assignee: Taiho Pharmaceutical Co., Ltd
    Inventors: Takashi Mizutani, Chihoko Yoshimura, Hitomi Kondo, Makoto Kitade, Shuichi Ohkubo
  • Patent number: 9951012
    Abstract: The present invention is related to an improved and efficient process for preparation of (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine which comprises: (a) N-acylation of 3-Amino-4-methyl pyridine; (b) Quarternization of 3-Acetylamino-4-methyl pyridine using benzyl halide; (c) Partial reduction of quarternized 3-Acetylamino-4-methyl pyridine by Sodium borohydride in Methanol or water; (d) Hydrolysis of partially reduced product to 1-Benzyl-4-methylpiperidin-3-one in presence of acid; (e) Reductive amination of 1-Benzyl-4-methylpiperidin-3-one using Methanolic methylamine in presence of Titanium(IV) isopropoxide in Methanol; (f) Resolution of 1-Benzyl-4-methylpiperidin-3-yl)-methylamine using Ditoluoyl (L) tartaric acid to get (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine. The invention is also related to novel intermediates: wherein R, R? and X are as described in the specification.
    Type: Grant
    Filed: December 2, 2014
    Date of Patent: April 24, 2018
    Assignee: UNICHEM LABORATORIES LIMITED
    Inventors: Dhananjay G. Sathe, Arijit Das, Yogesh Subhash Patil, Nilesh L. Bonde, Ankush Sampat Kekan
  • Patent number: 9908888
    Abstract: The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.
    Type: Grant
    Filed: February 5, 2016
    Date of Patent: March 6, 2018
    Assignees: Incyte Corporation, Incyte Holdings Corporation
    Inventors: Jiacheng Zhou, Pingli Liu, Qiyan Lin, Brian W. Metcalf, David Meloni, Yongchun Pan, Michael Xia, Mei Li, Tai-Yuen Yue, James D. Rodgers, Haisheng Wang
  • Patent number: 9873706
    Abstract: The present invention provides a process for the preparation of baricitinib and an intermediate thereof. The present invention provides a convenient, economical, and industrially advantageous two-step process for the preparation of [4-(IH-pyrazol-4-yl)-7Hpyrrolo[2,3-d] pyrimidin-7-yl]methyl pivalate of Formula (II). The process of the present invention involves the use of an alkali or alkaline earth metal hydroxide, carbonate, or bicarbonate as a base for reacting 4-chloro-7H-pyrrolo[2,3-d]pyrimidine of Formula (III) with chloromethyl pivalate of Formula (IV), and the use of an unprotected pyrazole borolane of Formula (VIII) for the conversion of (4-chloro-7H-pyrrolo[2,3-d] pyrimidin-7-yl)methyl 2,2-dimethylpropanoate of Formula V into [4-(1H-pyrazol-4-yl)-7Hpyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate of Formula (II). The process of the present invention provides [4-(1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]methyl pivalate of Formula (I) in high yield.
    Type: Grant
    Filed: December 4, 2015
    Date of Patent: January 23, 2018
    Assignee: Sun Pharmaceutical Industries Limited
    Inventors: Md Abul Kalam Azad, Gyanendra Pandey, Kaptan Singh, Mohan Prasad
  • Patent number: 9718829
    Abstract: Provided are crystalline forms of N-[4-[2-(2-amino-4, 7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]ben-zoyl]-L-glutamic acid, pemetrexed diacid, and processes for the preparation thereof.
    Type: Grant
    Filed: November 23, 2016
    Date of Patent: August 1, 2017
    Assignee: Sicor Inc.
    Inventors: Jonathan Busolli, Nicola Diulgheroff, Csilla Nemethne Racz, Moran Pirkes, Alessandro Pontiroli, Marco Villa, Judith Aronhime
  • Patent number: 9714233
    Abstract: This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.
    Type: Grant
    Filed: December 21, 2015
    Date of Patent: July 25, 2017
    Assignees: Incyte Corporation, Incyte Holdings Corporation
    Inventors: Pingli Liu, Dengjin Wang, Yongzhong Wu, Ganfeng Cao, Michael Xia
  • Patent number: 9682981
    Abstract: Compounds and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described, wherein the compounds have formula Ia: In certain aspects and embodiments, the described compounds or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof are active on one or more of Fms, Kit, Flt3, TrkA, TrkB and TrkC kinase protein.
    Type: Grant
    Filed: December 1, 2014
    Date of Patent: June 20, 2017
    Assignee: Plexxikon Inc.
    Inventors: Jiazhong Zhang, Prabha N. Ibrahim, Wayne Spevak, Jianming Tsai, Todd Ewing, Ying Zhang, Chao Zhang
  • Patent number: 9650384
    Abstract: This invention provides substituted pyrimidine compounds having the formula: wherein X is absent, CH2, S, or O, and R is an alkyl group having from one to ten carbon atoms, and optionally salts, hydrates, or solvates thereof, that are useful in treating a patient having a disease or cancer. The compounds of this invention are useful as multi-enzyme antifolates selectively targeting the folate receptor (FR). Further, a method of making 5- and 6-substituted cyclopenta[d]pyrimidine for nonclassical and classical antifolates as TS and DHFR inhibitors is provided.
    Type: Grant
    Filed: August 7, 2015
    Date of Patent: May 16, 2017
    Assignee: Duquesne University of the Holy Ghost
    Inventors: Aleem Gangjee, Larry H. Matherly
  • Patent number: 9617267
    Abstract: Compounds of formula (I): and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described. In certain aspects and embodiments, the described compounds of formula (I) or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof are active on at least one Raf protein kinase. In certain aspects and embodiments, the described compounds are active in inhibiting proliferation of a Ras mutant cell line. Also described are methods of use thereof to treat diseases and conditions, including diseases and conditions associated with activity of B-Raf V600E mutant protein kinase, including melanoma, glioma, glioblastoma multiforme, pilocytic astrocytoma, colorectal cancer, thyroid cancer, lung cancer, ovarian cancer, prostate cancer, liver cancer, gallbladder cancer, gastrointestinal stromal tumors, biliary tract cancer, and cholangiocarcinoma.
    Type: Grant
    Filed: March 17, 2014
    Date of Patent: April 11, 2017
    Assignee: Plexxikon Inc.
    Inventors: Prabha N. Ibrahim, Wayne Spevak, Hanna Cho, Songyuan Shi, Chao Zhang, Ying Zhang
  • Patent number: 9580429
    Abstract: There are disclosed novel compounds of formula (I) wherein R1, R12, L, X and Y are as defined in the specification, and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are inhibitors of the enzyme MPO and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders, cardiovascular disorders and respiratory disorders.
    Type: Grant
    Filed: September 15, 2014
    Date of Patent: February 28, 2017
    Assignee: AstraZeneca AB
    Inventors: Anders Bogevig, Yvonne Lo-Alfredsson, Donald Pivonka, Anna-Karin Tiden
  • Patent number: 9567341
    Abstract: Disclosed are chemical entities of formula I: wherein X, Y, Z, R1, R3, R4, R5 and R6 are defined herein, as NR2B subtype selective receptor antagonists. Also disclosed are pharmaceutical compositions comprising a chemical entity of formula I, and methods of treating various diseases and disorders associated with NR2B antagonism, e.g., diseases and disorders of the CNS, such as depression, by administering a chemical entity of formula I.
    Type: Grant
    Filed: September 15, 2015
    Date of Patent: February 14, 2017
    Assignee: Rugen Holdings (Cayman) Limited
    Inventor: Gideon Shapiro
  • Patent number: 9562050
    Abstract: Provided are crystalline forms of N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]ben-zoyl]-L-glutamic acid, pemetrexed diacid, and processes for the preparation thereof.
    Type: Grant
    Filed: September 16, 2015
    Date of Patent: February 7, 2017
    Assignee: Sicor, Inc.
    Inventors: Jonathan Busolli, Nicola Diulgheroff, Csilla Nemethne Racz, Moran Pirkes, Alessandro Pontiroli, Marco Villa, Judith Aronhime
  • Patent number: 9499549
    Abstract: This invention concerns pyrrolo[3,2-d]pyrimidine derivatives, processes for their preparation, pharmaceutical compositions, and their use in treatment and/or therapy of diseases.
    Type: Grant
    Filed: October 9, 2013
    Date of Patent: November 22, 2016
    Assignee: JANSSEN SCIENCES IRELAND UC
    Inventors: David Craig McGowan, Stefaan Julien Last, Serge Maria Aloysius Pieters, Werner Embrechts, Tim Hugo Maria Jonckers, Pierre Jean-Marie Bernard Raboisson
  • Patent number: 9492453
    Abstract: The invention relates to a novel group of compounds of Formula (I) or salts thereof: wherein Y, Z1, Z2, R1, R4, R5 and n are as described in the specification, which may be useful in the treatment or prevention of a disease or medical condition mediated through protein kinase B (PKB) such as cancer. The invention also relates to pharmaceutical compositions comprising said compounds, methods of treatment of diseases mediated by PKB using said compounds and methods for preparing compounds of Formula (I).
    Type: Grant
    Filed: February 19, 2015
    Date of Patent: November 15, 2016
    Assignee: AstraZeneca AB
    Inventors: Paul David Johnson, Andrew Leach, Richard William Arthur Luke, Zbigniew Stanley Matusiak, Jeffrey James Morris
  • Patent number: 9493465
    Abstract: The present invention relates to 3-hydroxypyrrolidine compounds of the general formula (I) which are inhibitors of 5?-methylthioadenosine phosphorylase or 5?-methylthioadenosine nucleosidase. The invention also relates to the use of these compounds in the treatment of diseases or conditions in which it is desirable to inhibit 5?-methylthioadenosine phosphorylase or 5?-methylthioadenosine nucleosidase including cancer, and to pharmaceutical compositions containing the compounds.
    Type: Grant
    Filed: July 16, 2010
    Date of Patent: November 15, 2016
    Assignees: Victoria Link Limited, Albert Einstein College of Medicine, Inc.
    Inventors: Gary Brian Evans, Alistair Ian Longshaw, Vern L. Schramm, Peter Charles Tyler
  • Patent number: 9487521
    Abstract: This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.
    Type: Grant
    Filed: September 6, 2012
    Date of Patent: November 8, 2016
    Assignees: Incyte Holdings Corporation, Incyte Corporation
    Inventors: Jiacheng Zhou, Yongzhong Wu, Pingli Liu, Ganfeng Cao
  • Patent number: 9428508
    Abstract: The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/or Pyk2 mediated disorder or disease.
    Type: Grant
    Filed: January 7, 2012
    Date of Patent: August 30, 2016
    Assignee: Centaurus BioPharma Co., Ltd.
    Inventors: Dengming Xiao, Liang Cheng, Xijie Liu, Yuandong Hu, Xinhe Xu, Zhihua Liu, Lipeng Zhang, Wei Wu, Shulong Wang, Yu Shen, Gen Li, Yin Wang, Sheng Zhao, Chonglong Li, Jia Tang, Honghao Yu