KR102469167B1 - Nmda 길항제 전구약물 - Google Patents

Nmda 길항제 전구약물 Download PDF

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KR102469167B1
KR102469167B1 KR1020217039470A KR20217039470A KR102469167B1 KR 102469167 B1 KR102469167 B1 KR 102469167B1 KR 1020217039470 A KR1020217039470 A KR 1020217039470A KR 20217039470 A KR20217039470 A KR 20217039470A KR 102469167 B1 KR102469167 B1 KR 102469167B1
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phenyl
pyridin
ethanamine
mmol
pharmaceutical composition
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KR20210148443A (ko
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구나르 노르드발
카타리나 회그딘
페르 조나스 말름보그
안니카 커스
디르크 바이겔트
페터 베른스타인
미카엘 퀴르크
발레스트라 미카엘
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아스트라제네카 아베
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052—Val-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • C07K5/06095—Arg-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06147—Dipeptides with the first amino acid being heterocyclic and His-amino acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06156—Dipeptides with the first amino acid being heterocyclic and Trp-amino acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
KR1020217039470A 2013-11-05 2014-10-30 Nmda 길항제 전구약물 Active KR102469167B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361899903P 2013-11-05 2013-11-05
US61/899,903 2013-11-05
KR1020167014625A KR102336426B1 (ko) 2013-11-05 2014-10-30 Nmda 길항제 전구약물
PCT/GB2014/053236 WO2015067923A1 (en) 2013-11-05 2014-10-30 Nmda antagonist prodrugs

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KR1020167014625A Division KR102336426B1 (ko) 2013-11-05 2014-10-30 Nmda 길항제 전구약물

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KR20210148443A KR20210148443A (ko) 2021-12-07
KR102469167B1 true KR102469167B1 (ko) 2022-11-22

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KR1020167014625A Active KR102336426B1 (ko) 2013-11-05 2014-10-30 Nmda 길항제 전구약물
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EP (3) EP3564234B1 (OSRAM)
JP (4) JP6479834B2 (OSRAM)
KR (2) KR102336426B1 (OSRAM)
CN (2) CN111187202B (OSRAM)
AR (1) AR098319A1 (OSRAM)
AU (1) AU2014345407B2 (OSRAM)
CA (1) CA2928004C (OSRAM)
CY (1) CY1121749T1 (OSRAM)
DK (1) DK3066091T3 (OSRAM)
ES (3) ES2894903T3 (OSRAM)
HR (2) HRP20241784T1 (OSRAM)
HU (2) HUE045001T2 (OSRAM)
LT (1) LT3066091T (OSRAM)
MX (2) MX377276B (OSRAM)
PL (2) PL4001272T3 (OSRAM)
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RU (1) RU2695372C2 (OSRAM)
SI (1) SI3066091T1 (OSRAM)
SM (1) SMT202500023T1 (OSRAM)
TR (1) TR201909632T4 (OSRAM)
TW (1) TW201609653A (OSRAM)
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Publication number Priority date Publication date Assignee Title
ES2894903T3 (es) 2013-11-05 2022-02-16 Astrazeneca Ab Profármacos antagonistas de NMDA
US11358935B2 (en) 2016-11-28 2022-06-14 Biohaven Pharmaceutical Holding Company Ltd. Prodrugs of lanicemine and their method of use
CN107578281B (zh) * 2017-08-31 2021-03-30 湖南大学 电子商务环境下用户优惠券行为预测方法及模型构建方法
KR20230026449A (ko) * 2020-06-23 2023-02-24 바이오하벤 테라퓨틱스 리미티드 (1s)-1-페닐-2-피리딘-2-일레탄아민의 국소 제형
WO2025137661A1 (en) * 2023-12-22 2025-06-26 Biohaven Therapeutics Ltd. Combination treatment of neurological disorders

Citations (3)

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Publication number Priority date Publication date Assignee Title
KR100259567B1 (ko) 1992-04-03 2000-07-01 클래스 빌헬름슨 신경변성 질환 치료용 1-페닐-2-(2-피리디닐)에틸아민 에난티오머
WO2010017504A1 (en) 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
WO2011089216A1 (en) 2010-01-22 2011-07-28 Ascendis Pharma As Dipeptide-based prodrug linkers for aliphatic amine-containing drugs

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US4769466A (en) * 1987-02-06 1988-09-06 Pennwalt Corporation 2-aminoacetamide pyridinyl derivatives
EP0356035B1 (en) * 1988-08-12 1996-03-13 Astra Aktiebolag Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties
SE9901077D0 (sv) 1999-03-23 1999-03-23 Astra Ab Novel use
SE9901340D0 (sv) 1999-04-15 1999-04-15 Astra Pharma Prod Novel process
US6613879B1 (en) * 1999-05-14 2003-09-02 Boehringer Ingelheim Pharma Kg FAP-activated anti-tumour compounds
US6407235B1 (en) 2000-08-21 2002-06-18 Hoffmann-La Roche Inc. Prodrug acid esters of [2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethansulfonyl]phenol
EP1404324B2 (en) * 2001-06-11 2011-04-06 XenoPort, Inc. Prodrugs of gaba analogs, compositions and uses thereof
GB0310593D0 (en) * 2003-05-08 2003-06-11 Leuven K U Res & Dev Peptidic prodrugs
WO2005066122A2 (en) 2003-12-30 2005-07-21 Xenoport, Inc. Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
CA2621847A1 (en) * 2005-09-08 2007-03-15 Shire Llc Prodrugs of t3 and t4 with enhanced bioavailability
CN101246417B (zh) 2007-02-13 2010-09-29 艾威梯科技(北京)有限公司 音频数据流输入/输出无间断软件切换的方法和系统
CA2710538A1 (en) 2008-01-25 2009-07-30 Xenoport, Inc. Crystalline form of a (3s)-aminomethyl-5-methyl-hexanoic acid prodrug and methods of use
US8580850B2 (en) * 2011-08-11 2013-11-12 Xenoport, Inc. Anhydrous and hemihydrate crystalline forms of an (R)-baclofen prodrug, methods of synthesis and methods of use
ES2894903T3 (es) 2013-11-05 2022-02-16 Astrazeneca Ab Profármacos antagonistas de NMDA

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100259567B1 (ko) 1992-04-03 2000-07-01 클래스 빌헬름슨 신경변성 질환 치료용 1-페닐-2-(2-피리디닐)에틸아민 에난티오머
WO2010017504A1 (en) 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
WO2011089216A1 (en) 2010-01-22 2011-07-28 Ascendis Pharma As Dipeptide-based prodrug linkers for aliphatic amine-containing drugs

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KR20210148443A (ko) 2021-12-07
ES2894903T3 (es) 2022-02-16
ES2733344T3 (es) 2019-11-28
LT3066091T (lt) 2019-07-10
HRP20191159T1 (hr) 2019-10-04
US20160280647A1 (en) 2016-09-29
EP3066091B1 (en) 2019-04-03
RU2016119493A (ru) 2017-12-07
JP2021100950A (ja) 2021-07-08
EP3066091A1 (en) 2016-09-14
RS58991B1 (sr) 2019-08-30
TR201909632T4 (tr) 2019-07-22
WO2015067923A1 (en) 2015-05-14
US20180037550A1 (en) 2018-02-08
EP4001272C0 (en) 2024-11-13
AU2014345407A1 (en) 2016-06-02
MX2016005567A (es) 2016-07-21
US20210040039A1 (en) 2021-02-11
US20190152914A1 (en) 2019-05-23
TW201609653A (zh) 2016-03-16
CN111187202A (zh) 2020-05-22
CN105683180B (zh) 2020-01-21
RU2695372C2 (ru) 2019-07-23
AU2014345407B2 (en) 2018-10-18
PL4001272T3 (pl) 2025-02-10
KR20160079094A (ko) 2016-07-05
US9822075B2 (en) 2017-11-21
CA2928004C (en) 2022-04-12
JP6479834B2 (ja) 2019-03-06
PT3066091T (pt) 2019-07-11
AR098319A1 (es) 2016-05-26
EP4001272B1 (en) 2024-11-13
EP3564234B1 (en) 2021-09-29
RU2016119493A3 (OSRAM) 2018-06-29
HRP20241784T1 (hr) 2025-02-28
JP7234278B2 (ja) 2023-03-07
JP2016535098A (ja) 2016-11-10
CA2928004A1 (en) 2015-05-14
MX394633B (es) 2025-03-24
JP6633233B2 (ja) 2020-01-22
BR112016009949A8 (pt) 2020-04-14
DK3066091T3 (da) 2019-07-15
US10207994B2 (en) 2019-02-19
KR102336426B1 (ko) 2021-12-08
EP3564234A1 (en) 2019-11-06
HUE070532T2 (hu) 2025-06-28
JP2020055857A (ja) 2020-04-09
PL3066091T3 (pl) 2019-10-31
JP6856737B2 (ja) 2021-04-07
SMT202500023T1 (it) 2025-03-12
SI3066091T1 (sl) 2019-09-30
HUE045001T2 (hu) 2019-12-30
CN105683180A (zh) 2016-06-15
MX2020011946A (es) 2022-08-10
MX377276B (es) 2025-03-07
EP4001272A1 (en) 2022-05-25
CN111187202B (zh) 2025-01-21
RS66369B1 (sr) 2025-01-31
UY35823A (es) 2015-04-30
ES2999064T3 (en) 2025-02-24
US10815199B2 (en) 2020-10-27
JP2019081781A (ja) 2019-05-30
CY1121749T1 (el) 2020-07-31

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