CA2990088C - Hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them - Google Patents

Hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them Download PDF

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Publication number
CA2990088C
CA2990088C CA2990088A CA2990088A CA2990088C CA 2990088 C CA2990088 C CA 2990088C CA 2990088 A CA2990088 A CA 2990088A CA 2990088 A CA2990088 A CA 2990088A CA 2990088 C CA2990088 C CA 2990088C
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CA
Canada
Prior art keywords
group
formula
phenyl
compound
pyrimidin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2990088A
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English (en)
French (fr)
Other versions
CA2990088A1 (en
Inventor
Zoltan Szlavik
Andras Kotschy
Maia Chanrion
Didier DEMARLES
Olivier Geneste
James Edward Paul Davidson
James Brooke MURRAY
Szabolcs SIPOS
Attila Paczal
Balazs Balint
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Les Laboratoires Servier SAS
Vernalis R&D Ltd
Original Assignee
Les Laboratoires Servier SAS
Vernalis R&D Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Les Laboratoires Servier SAS, Vernalis R&D Ltd filed Critical Les Laboratoires Servier SAS
Publication of CA2990088A1 publication Critical patent/CA2990088A1/en
Application granted granted Critical
Publication of CA2990088C publication Critical patent/CA2990088C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Steroid Compounds (AREA)
CA2990088A 2015-06-23 2016-06-22 Hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them Active CA2990088C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1555752 2015-06-23
FR1555752A FR3037957B1 (fr) 2015-06-23 2015-06-23 Nouveaux derives d'hydroxyester, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
PCT/EP2016/064433 WO2016207225A1 (en) 2015-06-23 2016-06-22 New hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them

Publications (2)

Publication Number Publication Date
CA2990088A1 CA2990088A1 (en) 2016-12-29
CA2990088C true CA2990088C (en) 2021-04-13

Family

ID=54608634

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2990088A Active CA2990088C (en) 2015-06-23 2016-06-22 Hydroxyester derivatives, a process for their preparation and pharmaceutical compositions containing them

Country Status (43)

Country Link
US (2) US10227358B2 (https=)
EP (1) EP3313851B1 (https=)
JP (1) JP6741697B2 (https=)
KR (1) KR102718253B1 (https=)
CN (1) CN107709333B (https=)
AR (1) AR105103A1 (https=)
AU (1) AU2016282836B2 (https=)
BR (1) BR112017027414B1 (https=)
CA (1) CA2990088C (https=)
CL (1) CL2017003258A1 (https=)
CO (1) CO2017012786A2 (https=)
CR (1) CR20170564A (https=)
CU (1) CU20170160A7 (https=)
CY (1) CY1122542T1 (https=)
DK (1) DK3313851T3 (https=)
EA (1) EA033266B1 (https=)
EC (1) ECSP17081744A (https=)
ES (1) ES2759480T3 (https=)
FR (1) FR3037957B1 (https=)
GE (2) GEP20207074B (https=)
HK (1) HK1249506A1 (https=)
HR (1) HRP20200107T1 (https=)
HU (1) HUE047889T2 (https=)
IL (1) IL256270A (https=)
JO (1) JO3675B1 (https=)
MA (1) MA42239B1 (https=)
MD (1) MD3313851T2 (https=)
MX (1) MX372716B (https=)
MY (1) MY190561A (https=)
PE (1) PE20180742A1 (https=)
PH (1) PH12017502246B1 (https=)
PL (1) PL3313851T3 (https=)
PT (1) PT3313851T (https=)
RS (1) RS59904B1 (https=)
RU (1) RU2734418C2 (https=)
SI (1) SI3313851T1 (https=)
SV (1) SV2017005587A (https=)
TN (1) TN2017000511A1 (https=)
TW (1) TWI604844B (https=)
UA (1) UA122228C2 (https=)
UY (1) UY36736A (https=)
WO (1) WO2016207225A1 (https=)
ZA (1) ZA201708460B (https=)

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FR3037956B1 (fr) * 2015-06-23 2017-08-04 Servier Lab Nouveaux derives d'acide amine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3037959B1 (fr) * 2015-06-23 2017-08-04 Servier Lab Nouveaux derives bicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3037958B1 (fr) * 2015-06-23 2019-01-25 Les Laboratoires Servier Nouveaux derives d'hydroxy-acide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2018015526A1 (en) 2016-07-22 2018-01-25 Les Laboratoires Servier Combination of a bcl-2 inhibitor and a mcl-1 inhibitor, uses and pharmaceutical compositions thereof
EP3567043B1 (en) * 2017-01-05 2023-12-06 Henan Genuine Biotech Co., Ltd. 2-[[5-[(4-hydroxy-3-chloro-2-methyl)-phenyl]-thieno[2,3-d]pyrimidin-4-yl]oxy]-3-(2-methoxybenzene)propanoic acid derivatives as mcl-1 and bcl-2 inhibitors for treating cancer
UY37560A (es) 2017-01-06 2018-07-31 Servier Lab Combinación de un inhibidor de mcl-1 y un compuesto taxano, usos y composiciones farmacéuticas de ésta
CN110381937A (zh) * 2017-01-06 2019-10-25 法国施维雅药厂 Mcl-1抑制剂和紫杉烷化合物的组合及其用途和药物组合物
TWI753178B (zh) * 2017-06-22 2022-01-21 法商施維雅藥廠 Mcl-1抑制劑與血液癌症標準療法之組合,其用途及醫藥組合物
AU2018317828A1 (en) * 2017-08-15 2020-04-02 AbbVie Deutschland GmbH & Co. KG Macrocyclic MCL-1 inhibitors and methods of use
CN111818917A (zh) 2017-08-15 2020-10-23 艾伯维公司 大环mcl-1抑制剂和使用方法
WO2019101144A1 (zh) * 2017-11-23 2019-05-31 北京赛林泰医药技术有限公司 Mcl-1选择性抑制剂及其制备和用途
CN108424417B (zh) * 2017-12-21 2019-09-20 河南真实生物科技有限公司 噻吩并嘧啶衍生物、其制备方法及在制备抗肿瘤药物中的应用
CN110964034B (zh) * 2018-09-29 2022-04-12 江苏恒瑞医药股份有限公司 嘧啶并噻吩类衍生物、其制备方法及其在医药上的应用
TWI849001B (zh) 2018-11-14 2024-07-21 法商施維雅藥廠 Mcl-1抑制劑及米哚妥林(midostaurin)之組合,其用途及醫藥組合物
CN111187277B (zh) * 2018-11-14 2022-04-12 江苏恒瑞医药股份有限公司 噻吩并嘧啶类衍生物、其制备方法及其在医药上的应用
AU2019391329B2 (en) * 2018-12-06 2024-09-26 Les Laboratoires Servier New crystalline forms of a MCL-1 inhibitor, a process for their preparation and pharmaceutical compositions containing them.
KR20220024106A (ko) 2019-05-20 2022-03-03 노파르티스 아게 Mcl-1 억제제 항체-약물 접합체 및 사용 방법
AR119156A1 (es) 2019-06-17 2021-11-24 Servier Lab Combinación de un inhibidor de mcl-1 y un tratamiento estándar de atención médica para cáncer de mama, usos y composiciones farmacéuticas de la misma
US20230116602A1 (en) * 2019-10-03 2023-04-13 California Institute Of Technology Mcl1 inhibitors and uses thereof
US20240042051A1 (en) 2020-11-24 2024-02-08 Francesca Rocchetti Mcl-1 inhibitor antibody-drug conjugates and methods of use
WO2022216946A1 (en) * 2021-04-07 2022-10-13 California Institute Of Technology Mcl1 inhibitors and uses thereof
JP7673255B2 (ja) 2021-06-11 2025-05-08 ギリアード サイエンシーズ, インコーポレイテッド Mcl-1阻害剤と抗体薬物コンジュゲートとの組み合わせ
TWI910028B (zh) 2021-06-11 2025-12-21 美商基利科學股份有限公司 Mcl-1抑制劑與抗癌劑之組合
CN113651663B (zh) * 2021-08-20 2024-03-29 浙大宁波理工学院 一种氘代芳香羰基类化合物的制备方法
EP4413165A1 (en) 2021-10-06 2024-08-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for predicting and improving the efficacy of mcl-1 inhibitor therapy
CN120787162A (zh) 2022-05-20 2025-10-14 诺华股份有限公司 抗肿瘤化合物的抗体-药物缀合物及其使用方法
PY24103486A (es) 2023-11-22 2025-06-06 Servier Lab Conjugados de anticuerpo anti-cd74-fármaco y métodos de uso de los mismos
TW202540186A (zh) 2023-11-22 2025-10-16 瑞士商諾華公司 抗cd7抗體藥物結合物及其使用方法
TW202530255A (zh) 2023-12-15 2025-08-01 法商亞維西亞有限公司 抗il-1rap結合結構域及其抗體-藥物偶聯物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2217956B1 (es) * 2003-01-23 2006-04-01 Almirall Prodesfarma, S.A. Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo.
EA009920B1 (ru) * 2003-08-29 2008-04-28 Вернэлис (Кембридж) Лимитед Соединения пиримидотиофена
BRPI0908573A2 (pt) * 2008-03-05 2012-12-25 Methylgene Inc inibidores da atividade de proteÍna tirosina quinase
CN102464667B (zh) * 2010-11-03 2014-06-04 中国科学院上海药物研究所 一类五元杂环并嘧啶类化合物及其制备方法和用途
AR090037A1 (es) * 2011-11-15 2014-10-15 Xention Ltd Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio
FR3015483B1 (fr) * 2013-12-23 2016-01-01 Servier Lab Nouveaux derives de thienopyrimidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3037958B1 (fr) * 2015-06-23 2019-01-25 Les Laboratoires Servier Nouveaux derives d'hydroxy-acide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3037956B1 (fr) * 2015-06-23 2017-08-04 Servier Lab Nouveaux derives d'acide amine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR3037959B1 (fr) * 2015-06-23 2017-08-04 Servier Lab Nouveaux derives bicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Also Published As

Publication number Publication date
US20190161496A1 (en) 2019-05-30
PH12017502246A1 (en) 2018-05-28
UY36736A (es) 2016-12-30
ECSP17081744A (es) 2018-02-28
CR20170564A (es) 2018-02-20
PE20180742A1 (es) 2018-04-27
HK1249506A1 (zh) 2018-11-02
EA201890125A1 (ru) 2018-06-29
JP2018522855A (ja) 2018-08-16
ES2759480T3 (es) 2020-05-11
HK1254657A1 (en) 2019-07-26
RU2734418C2 (ru) 2020-10-16
US20180170947A1 (en) 2018-06-21
AU2016282836A1 (en) 2018-01-18
EP3313851B1 (en) 2019-11-06
KR102718253B1 (ko) 2024-10-16
UA122228C2 (uk) 2020-10-12
US10227358B2 (en) 2019-03-12
NZ738455A (en) 2024-03-22
ZA201708460B (en) 2021-06-30
CN107709333B (zh) 2021-01-01
MX2017016997A (es) 2018-09-07
FR3037957A1 (https=) 2016-12-30
AR105103A1 (es) 2017-09-06
AU2016282836B2 (en) 2020-07-09
WO2016207225A1 (en) 2016-12-29
CA2990088A1 (en) 2016-12-29
US10711010B2 (en) 2020-07-14
MA42239B1 (fr) 2020-02-28
BR112017027414A2 (pt) 2018-08-28
CO2017012786A2 (es) 2018-04-10
KR20180019223A (ko) 2018-02-23
GEAP201914678A (en) 2019-11-11
BR112017027414B1 (pt) 2023-12-19
SV2017005587A (es) 2018-04-11
CU20170160A7 (es) 2018-05-08
HRP20200107T1 (hr) 2020-04-03
MD3313851T2 (ro) 2020-02-29
TW201709911A (zh) 2017-03-16
RS59904B1 (sr) 2020-03-31
CN107709333A (zh) 2018-02-16
MX372716B (es) 2020-05-28
IL256270A (en) 2018-02-28
RU2018102365A3 (https=) 2019-09-23
SI3313851T1 (sl) 2020-03-31
FR3037957B1 (fr) 2019-01-25
CL2017003258A1 (es) 2018-06-01
EP3313851A1 (en) 2018-05-02
JO3675B1 (ar) 2020-08-27
DK3313851T3 (da) 2020-01-27
TN2017000511A1 (en) 2019-04-12
GEP20207074B (en) 2020-03-10
HUE047889T2 (hu) 2020-05-28
JP6741697B2 (ja) 2020-08-19
PT3313851T (pt) 2020-01-06
RU2018102365A (ru) 2019-07-23
PL3313851T3 (pl) 2020-05-18
PH12017502246B1 (en) 2018-05-28
EA033266B1 (ru) 2019-09-30
CY1122542T1 (el) 2021-01-27
MY190561A (en) 2022-04-27
TWI604844B (zh) 2017-11-11

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