WO2017152725A1 - Composé rétinoïde, son procédé de préparation, ses intermédiaires et application correspondante - Google Patents

Composé rétinoïde, son procédé de préparation, ses intermédiaires et application correspondante Download PDF

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Publication number
WO2017152725A1
WO2017152725A1 PCT/CN2017/071922 CN2017071922W WO2017152725A1 WO 2017152725 A1 WO2017152725 A1 WO 2017152725A1 CN 2017071922 W CN2017071922 W CN 2017071922W WO 2017152725 A1 WO2017152725 A1 WO 2017152725A1
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WIPO (PCT)
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compound
group
wyc
mmol
added
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PCT/CN2017/071922
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English (en)
Chinese (zh)
Inventor
曹鑫
俞飚
汪宁
陈俊威
Original Assignee
中国科学院上海有机化学研究所
华中科技大学
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
Priority claimed from CN201610310944.8A external-priority patent/CN107176945B/zh
Application filed by 中国科学院上海有机化学研究所, 华中科技大学 filed Critical 中国科学院上海有机化学研究所
Priority to EP17762411.1A priority Critical patent/EP3428155A4/fr
Priority to CA3017395A priority patent/CA3017395A1/fr
Priority to US16/083,879 priority patent/US10556879B2/en
Priority to JP2018548077A priority patent/JP2019509295A/ja
Publication of WO2017152725A1 publication Critical patent/WO2017152725A1/fr
Priority to US16/733,089 priority patent/US20200216407A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/382—Heterocyclic compounds having sulfur as a ring hetero atom having six-membered rings, e.g. thioxanthenes
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

La présente invention concerne un composé rétinoïde, son procédé de préparation, ses intermédiaires et une application correspondante. Le composé rétinoïde I de la présente invention présente un bon taux d'inhibition de la croissance tumorale.
PCT/CN2017/071922 2016-03-11 2017-01-20 Composé rétinoïde, son procédé de préparation, ses intermédiaires et application correspondante WO2017152725A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP17762411.1A EP3428155A4 (fr) 2016-03-11 2017-01-20 Composé rétinoïde, son procédé de préparation, ses intermédiaires et application correspondante
CA3017395A CA3017395A1 (fr) 2016-03-11 2017-01-20 Compose retinoide, son procede de preparation, ses intermediaires et application correspondante
US16/083,879 US10556879B2 (en) 2016-03-11 2017-01-20 Retinoid compound, preparation method therefor, intermediates thereof and application thereof
JP2018548077A JP2019509295A (ja) 2016-03-11 2017-01-20 レチノイン酸系化合物、その製造方法、中間体及び応用
US16/733,089 US20200216407A1 (en) 2016-03-11 2020-01-02 Retinoid compound, preparation method therefor, intermediates thereof and application thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201610141143 2016-03-11
CN201610141143.3 2016-03-11
CN201610310944.8 2016-05-11
CN201610310944.8A CN107176945B (zh) 2016-03-11 2016-05-11 一种视黄酸类化合物、其制备方法、中间体及应用

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US16/083,879 A-371-Of-International US10556879B2 (en) 2016-03-11 2017-01-20 Retinoid compound, preparation method therefor, intermediates thereof and application thereof
US16/733,089 Division US20200216407A1 (en) 2016-03-11 2020-01-02 Retinoid compound, preparation method therefor, intermediates thereof and application thereof

Publications (1)

Publication Number Publication Date
WO2017152725A1 true WO2017152725A1 (fr) 2017-09-14

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PCT/CN2017/071922 WO2017152725A1 (fr) 2016-03-11 2017-01-20 Composé rétinoïde, son procédé de préparation, ses intermédiaires et application correspondante

Country Status (1)

Country Link
WO (1) WO2017152725A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020183173A3 (fr) * 2019-03-11 2020-12-03 University Of Durham Rétinoïdes synthétiques destinés à être utilisés dans l'activation de rar
CN115974860A (zh) * 2022-12-15 2023-04-18 复旦大学附属中山医院 维甲酸类化合物及其制备方法和用途、含该化合物的药物组合物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1050385A (zh) * 1989-09-19 1991-04-03 阿勒根公司 制备具有类视黄酸生物活性的带有二取代的乙炔部分的化合物的方法以及中间体
WO1993016068A1 (fr) * 1992-02-14 1993-08-19 Allergan, Inc. Acetylenes disubstitues comportant des groupes heterobicycliques et des groupes heteroaromatiques ou phenyles possedant une efficacite analogue aux retinoides
US6001885A (en) * 1996-09-02 1999-12-14 Centre International De Recherches Dermatologiques Retinoid inhibition of expression of VEGF
CN1360890A (zh) * 1995-09-01 2002-07-31 阿勒根公司 具负性激素和/或拮抗剂活性视黄醛衍生物的用途
WO2003062369A2 (fr) * 2002-01-24 2003-07-31 Gamida-Cell Ltd. Developpement de populations de cellules souches renouvelables
CN102595892A (zh) * 2009-07-16 2012-07-18 施泰福实验室股份有限公司 他扎罗汀衍生物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1050385A (zh) * 1989-09-19 1991-04-03 阿勒根公司 制备具有类视黄酸生物活性的带有二取代的乙炔部分的化合物的方法以及中间体
WO1993016068A1 (fr) * 1992-02-14 1993-08-19 Allergan, Inc. Acetylenes disubstitues comportant des groupes heterobicycliques et des groupes heteroaromatiques ou phenyles possedant une efficacite analogue aux retinoides
CN1360890A (zh) * 1995-09-01 2002-07-31 阿勒根公司 具负性激素和/或拮抗剂活性视黄醛衍生物的用途
US6001885A (en) * 1996-09-02 1999-12-14 Centre International De Recherches Dermatologiques Retinoid inhibition of expression of VEGF
WO2003062369A2 (fr) * 2002-01-24 2003-07-31 Gamida-Cell Ltd. Developpement de populations de cellules souches renouvelables
CN102595892A (zh) * 2009-07-16 2012-07-18 施泰福实验室股份有限公司 他扎罗汀衍生物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEN, XIAOLI: "New Advances in Clinical Application of Tazarotene", FOREIGN MEDICAL SCIENCES(GERIATRICS, vol. 27, no. 5, 30 June 2006 (2006-06-30), pages 193 - 196, XP009508898 *
See also references of EP3428155A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020183173A3 (fr) * 2019-03-11 2020-12-03 University Of Durham Rétinoïdes synthétiques destinés à être utilisés dans l'activation de rar
CN115974860A (zh) * 2022-12-15 2023-04-18 复旦大学附属中山医院 维甲酸类化合物及其制备方法和用途、含该化合物的药物组合物

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