KR102711990B1 - 골관절염의 치료를 위한 에이디에이엠티에스 억제제로서 5-[(피페라진-1-일)-3-옥소-프로필]-이미다졸리딘-2,4-디온 유도체 - Google Patents

골관절염의 치료를 위한 에이디에이엠티에스 억제제로서 5-[(피페라진-1-일)-3-옥소-프로필]-이미다졸리딘-2,4-디온 유도체 Download PDF

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KR102711990B1
KR102711990B1 KR1020177020379A KR20177020379A KR102711990B1 KR 102711990 B1 KR102711990 B1 KR 102711990B1 KR 1020177020379 A KR1020177020379 A KR 1020177020379A KR 20177020379 A KR20177020379 A KR 20177020379A KR 102711990 B1 KR102711990 B1 KR 102711990B1
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methyl
dione
imidazolidine
piperazin
oxo
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KR20170122720A (ko
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프랑크 로렌트 브레비온
루크 조나단 앨비
데이비드 아만티니
피에르 마르크 마리에 조세피 드프레즈
로메인 룩 마리에 고스미니
헬레네 마리에 제리
크리스토프 페이쇼투
마리에 로렌스 클레어 바린
프레데릭 안드레 드 세우니닉
일루리아나 에카테리나 팝-포테즈
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갈라파고스 엔.브이.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
KR1020177020379A 2014-12-22 2015-12-18 골관절염의 치료를 위한 에이디에이엠티에스 억제제로서 5-[(피페라진-1-일)-3-옥소-프로필]-이미다졸리딘-2,4-디온 유도체 Active KR102711990B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14307129 2014-12-22
EP14307129.8 2014-12-22
PCT/EP2015/080430 WO2016102347A1 (en) 2014-12-22 2015-12-18 5-[(piperazin-1-yl)-3-oxo-propyl]-imidazolidine-2,4-dione derivatives as adamts inhibitors for the treatment of osteoarthritis

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Publication Number Publication Date
KR20170122720A KR20170122720A (ko) 2017-11-06
KR102711990B1 true KR102711990B1 (ko) 2024-10-02

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KR1020177020379A Active KR102711990B1 (ko) 2014-12-22 2015-12-18 골관절염의 치료를 위한 에이디에이엠티에스 억제제로서 5-[(피페라진-1-일)-3-옥소-프로필]-이미다졸리딘-2,4-디온 유도체

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JO3501B1 (ar) 2014-12-22 2020-07-05 Servier Lab مشتقات 5-{(بيبرازين - 1-يل)-3-أوكسو - بروبيل}- إيميدازوليدين-2، 4 - دايون كمثبطات ل adamts لمعالجة هشاشة العظام)
GB201610056D0 (en) * 2016-06-09 2016-07-27 Galapagos Nv And Laboratoires Servier Les Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders and osteoarthritis
GB201610055D0 (en) * 2016-06-09 2016-07-27 Galapagos Nv And Laboratoires Servier Les Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders and osteoarthritis
CN107540648A (zh) * 2017-08-09 2018-01-05 江苏工程职业技术学院 一种达格列净的制备方法
CN107652277A (zh) * 2017-08-09 2018-02-02 江苏工程职业技术学院 一种依帕列净的制备方法
WO2021011723A1 (en) * 2019-07-18 2021-01-21 Avidence Therapeutics, Inc. Anti-osteoarthritis hydantoin compounds and related compositions and methods
JP2023513121A (ja) * 2020-02-04 2023-03-30 江蘇恒瑞医薬股▲ふん▼有限公司 Ａｄａｍｔｓ阻害剤、その製造および医薬用途
WO2021204185A1 (zh) * 2020-04-10 2021-10-14 深圳信立泰药业股份有限公司 一种苯并[d]氮杂卓类衍生物蛋白聚糖酶2抑制剂及其制备方法和医药用途
CN113735825B (zh) * 2020-05-27 2024-08-27 成都康弘药业集团股份有限公司 1,2,3,6-四氢吡啶类化合物及其制备方法和用途
CN113754635B (zh) * 2020-06-02 2024-06-21 成都康弘药业集团股份有限公司 稠环类化合物及其制备方法和用途
WO2022007866A1 (zh) * 2020-07-09 2022-01-13 深圳信立泰药业股份有限公司 并三环类衍生物、其制备方法及其在医药上的应用
CN113943255B (zh) * 2020-07-17 2024-08-06 深圳信立泰药业股份有限公司 一种手性3-(4-环丙基-2,5-二氧杂咪唑啉-4-基)丙酸的制备方法
CN116723840A (zh) * 2020-12-15 2023-09-08 加拉帕戈斯股份有限公司 (5s)-环丙基-5-[3-[(3s)-4-(3,5-二氟苯基)-3-甲基-哌嗪-1-基]-3-氧代-丙基]咪唑烷-2,4-二酮的固体形式
AU2021399788A1 (en) 2020-12-15 2023-08-03 Lakefront Biotherapeutics Nv Solid forms of (5s)-cyclopropyl-5-[3-[(3s)-4-(3,5-difluorophenyl)-3-methyl-piperazin-1-yl]-3-oxo-propyl]imidazolidine-2,4-dione
WO2022212638A1 (en) * 2021-04-02 2022-10-06 Jiangsu Hengrui Pharmaceuticals Co., Ltd. Prodrugs of adamts inhibitors, preparation methods and medicinal uses thereof
TW202321221A (zh) * 2021-08-03 2023-06-01 大陸商江蘇恒瑞醫藥股份有限公司 抑制adamts-5和/或adamts-4功能的化合物的晶型及其製備方法和應用
KR20240140825A (ko) 2023-03-17 2024-09-24 주식회사 셀러스 이미다졸리딘 유도체 또는 이의 약학적으로 허용 가능한 염 및 이의 용도

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JP2004527515A (ja) 2001-03-15 2004-09-09 アストラゼネカ・アクチエボラーグ メタロプロテイナーゼ阻害剤
JP2009523795A (ja) 2006-01-17 2009-06-25 シェーリング コーポレイション 炎症性障害の処置のためのヒダントイン化合物
WO2013153189A1 (en) 2012-04-13 2013-10-17 Rottapharm Biotech S.R.L. Anti-adamts-5 antibody, derivatives and uses thereof
WO2014066151A1 (en) 2012-10-26 2014-05-01 Eli Lilly And Company Aggrecanase inhibitors

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EP2953932B1 (en) 2013-02-06 2017-03-01 Merck Patent GmbH Substituted carboxylic acid derivatives as aggrecanase inhibitors for the treatment of osteoarthritis
JO3501B1 (ar) 2014-12-22 2020-07-05 Servier Lab مشتقات 5-{(بيبرازين - 1-يل)-3-أوكسو - بروبيل}- إيميدازوليدين-2، 4 - دايون كمثبطات ل adamts لمعالجة هشاشة العظام)

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JP2004527515A (ja) 2001-03-15 2004-09-09 アストラゼネカ・アクチエボラーグ メタロプロテイナーゼ阻害剤
JP2009523795A (ja) 2006-01-17 2009-06-25 シェーリング コーポレイション 炎症性障害の処置のためのヒダントイン化合物
WO2013153189A1 (en) 2012-04-13 2013-10-17 Rottapharm Biotech S.R.L. Anti-adamts-5 antibody, derivatives and uses thereof
WO2014066151A1 (en) 2012-10-26 2014-05-01 Eli Lilly And Company Aggrecanase inhibitors

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CR20170248A (es) 2017-07-19
JP2018502906A (ja) 2018-02-01
PL3237406T3 (pl) 2019-07-31
LT3237406T (lt) 2019-03-25
EP3237406B1 (en) 2019-02-06
HRP20190514T1 (hr) 2019-05-03
EP3575294A1 (en) 2019-12-04
GEAP201914546A (en) 2019-07-25
US20210309614A1 (en) 2021-10-07
WO2016102347A1 (en) 2016-06-30
BR112017013258A8 (pt) 2022-08-16
TWI687414B (zh) 2020-03-11
CU20170085A7 (es) 2017-10-05
BR112017013258A2 (pt) 2018-02-06
NI201700081A (es) 2017-09-08
UA122065C2 (uk) 2020-09-10
PH12017501160A1 (en) 2017-12-11
RS58617B1 (sr) 2019-05-31
CA2971110A1 (en) 2016-06-30
BR112017013258B1 (pt) 2023-02-07
EA030637B1 (ru) 2018-09-28
MX2017008048A (es) 2017-10-19
CL2017001650A1 (es) 2018-01-26
ECSP17046848A (es) 2017-10-31
US10487060B2 (en) 2019-11-26
MY189764A (en) 2022-03-03
US20180002293A1 (en) 2018-01-04
US9926281B2 (en) 2018-03-27
GEP20197043B (en) 2019-11-25
RU2693459C2 (ru) 2019-07-03
AU2015371400B2 (en) 2019-07-25
JP2020063278A (ja) 2020-04-23
KR20170122720A (ko) 2017-11-06
PT3237406T (pt) 2019-03-19
ES2724989T3 (es) 2019-09-18
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MD3237406T2 (ro) 2019-05-31
SI3237406T1 (sl) 2019-04-30
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RU2017126187A (ru) 2019-01-24
CN107108579B (zh) 2019-12-17
TN2017000213A1 (en) 2018-10-19
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EP3237406A1 (en) 2017-11-01
EA201791451A1 (ru) 2017-11-30
US11718588B2 (en) 2023-08-08
ZA201703905B (en) 2022-03-30
TW201629041A (zh) 2016-08-16
US20180258052A1 (en) 2018-09-13
MA41238A (fr) 2017-11-01
IL252981B (en) 2019-07-31
UY36470A (es) 2016-07-29
JO3501B1 (ar) 2020-07-05
DOP2017000139A (es) 2017-10-31
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US20200216397A1 (en) 2020-07-09
DK3237406T3 (da) 2019-05-06
IL252981A0 (en) 2017-08-31
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RU2017126187A3 (enExample) 2019-01-24
AU2015371400A1 (en) 2017-07-06
ME03374B (me) 2020-01-20
AR103170A1 (es) 2017-04-19
MA41238B1 (fr) 2019-04-30
CA2971110C (en) 2023-05-16
US10941117B2 (en) 2021-03-09
CN107108579A (zh) 2017-08-29
SG11201705030SA (en) 2017-07-28
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