MX2020003815A - Sintesis de cantaridina. - Google Patents

Sintesis de cantaridina.

Info

Publication number
MX2020003815A
MX2020003815A MX2020003815A MX2020003815A MX2020003815A MX 2020003815 A MX2020003815 A MX 2020003815A MX 2020003815 A MX2020003815 A MX 2020003815A MX 2020003815 A MX2020003815 A MX 2020003815A MX 2020003815 A MX2020003815 A MX 2020003815A
Authority
MX
Mexico
Prior art keywords
cantharidin
provides
compounds
analogues
formula
Prior art date
Application number
MX2020003815A
Other languages
English (en)
Inventor
Steven R Schow
Matthew Gene Davidson
Brian Matthew Eklov
Peter Wuts
Brad Melvin Loertscher
Original Assignee
Verrica Pharmaceuticals Inc
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 Verrica Pharmaceuticals Inc filed Critical Verrica Pharmaceuticals Inc
Publication of MX2020003815A publication Critical patent/MX2020003815A/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic 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 four or more hetero rings
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • 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
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic 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
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic 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 three hetero rings
    • C07D495/18—Bridged systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Abstract

La invención proporciona métodos sintéticos para la preparación de cantaridina y análogos de la misma; en un aspecto, la invención proporciona una cicloadición Diels-Alder mejorada para generar un intermedio clave en el camino hacia la cantaridina y sus análogos; en ciertas modalidades, la nueva reacción de Diels-Alder implica hacer reaccionar el compuesto (2) en presencia de furano, y en ausencia de ácido o presión aumentada, en un solvente polar aprótico con ligero calentamiento, para producir el compuesto (1) con un rendimiento favorable y relación exoendo; en otro aspecto, la invención también proporciona una nueva reacción Diels-Alder entre compuestos de fórmula (III) y furano para producir compuestos de fórmula (IV), que luego pueden transformarse en cantaridina o análogos de los mismos; en otro aspecto más, la invención describe una nueva carbonilación mediada por paladio que proporciona otro intermedio clave en el camino hacia la cantaridina y sus análogos; además de los métodos sintéticos, la presente invención también proporciona compuestos (es decir, intermedios) útiles en la síntesis de cantaridina y análogos de los mismos; los compuestos proporcionados en este documento pueden tener actividad biológica y, por lo tanto, pueden usarse en el tratamiento de enfermedades o afecciones (por ejemplo, enfermedades infecciosas y afecciones de la piel). (FORMULA).
MX2020003815A 2017-10-04 2018-10-04 Sintesis de cantaridina. MX2020003815A (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762568004P 2017-10-04 2017-10-04
PCT/US2018/054373 WO2019070980A2 (en) 2017-10-04 2018-10-04 SYNTHESIS OF CANTHARIDINE

Publications (1)

Publication Number Publication Date
MX2020003815A true MX2020003815A (es) 2020-11-09

Family

ID=65994279

Family Applications (2)

Application Number Title Priority Date Filing Date
MX2020003815A MX2020003815A (es) 2017-10-04 2018-10-04 Sintesis de cantaridina.
MX2022013045A MX2022013045A (es) 2017-10-04 2020-07-13 Sintesis de cantaridina.

Family Applications After (1)

Application Number Title Priority Date Filing Date
MX2022013045A MX2022013045A (es) 2017-10-04 2020-07-13 Sintesis de cantaridina.

Country Status (11)

Country Link
US (2) US20200270269A1 (es)
EP (2) EP3692044B1 (es)
JP (2) JP7411545B2 (es)
KR (1) KR20200065031A (es)
CN (1) CN111819182B (es)
AU (2) AU2018346414B2 (es)
BR (1) BR112020006703A2 (es)
CA (1) CA3078325A1 (es)
IL (2) IL305371A (es)
MX (2) MX2020003815A (es)
WO (1) WO2019070980A2 (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114209688A (zh) 2013-08-21 2022-03-22 威瑞卡制药公司 用于治疗皮肤病症的组合物、方法和系统
US11168091B2 (en) 2015-01-20 2021-11-09 Verrica Pharmaceuticals Inc. Quantification and preparation of pharmaceutical grade cantharidin
JP7280870B2 (ja) 2017-06-06 2023-05-24 ヴェリカ ファーマシューティカルズ インコーポレーテッド 皮膚障害の処置
CN113455515A (zh) * 2021-06-24 2021-10-01 广东省农业科学院果树研究所 斑蝥素在制备防治柑橘采后绿霉菌的农药杀菌剂的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3981924A (en) * 1974-04-22 1976-09-21 International Flavors & Fragrances Inc. Diels-Alder adduct product
JPS51141863A (en) * 1975-06-02 1976-12-07 Nippon Nohyaku Co Ltd Process for preparing organo-phosphoric acid esters
US4413154A (en) * 1982-09-27 1983-11-01 Mobil Oil Corporation Diels-Alder cyclodimerization over a carbon molecular sieve catalyst
US5464855A (en) * 1994-08-09 1995-11-07 Warner-Lambert Company Thiophene-2-carboxamidotetrazoles and pharmaceutical use thereof
EP2307558A4 (en) * 2008-07-03 2012-08-08 Allelogic Biosciences Corp COMPOSITIONS AND PROCEDURES FOR THE PROTECTION OF NUCLEOPHILER GROUPS
JP6215924B2 (ja) * 2012-06-19 2017-10-18 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ 新規の二環式チオフェニルアミド化合物
MX2017008097A (es) 2014-12-17 2018-01-09 Verrica Pharmaceuticals Inc Sintesis comercialmente viable de cantaridina y derivados bioactivos de cantaridina.
CN106674248B (zh) 2016-12-17 2019-02-26 重庆市中药研究院 一种斑蝥素的合成工艺

Also Published As

Publication number Publication date
AU2018346414B2 (en) 2023-07-06
CA3078325A1 (en) 2019-04-11
JP7411545B2 (ja) 2024-01-11
EP3692044A2 (en) 2020-08-12
US20200270269A1 (en) 2020-08-27
AU2023204584A1 (en) 2023-08-24
EP3692044A4 (en) 2021-08-04
IL273784A (en) 2020-05-31
US20240109911A1 (en) 2024-04-04
CN111819182B (zh) 2024-01-30
EP4339199A3 (en) 2024-05-15
IL305371A (en) 2023-10-01
JP2024045118A (ja) 2024-04-02
IL273784B1 (en) 2023-10-01
EP3692044B1 (en) 2024-01-24
WO2019070980A2 (en) 2019-04-11
BR112020006703A2 (pt) 2020-10-06
JP2020536879A (ja) 2020-12-17
AU2018346414A1 (en) 2020-04-30
WO2019070980A3 (en) 2019-05-16
EP4339199A2 (en) 2024-03-20
MX2022013045A (es) 2022-11-10
KR20200065031A (ko) 2020-06-08
IL273784B2 (en) 2024-02-01
CN111819182A (zh) 2020-10-23

Similar Documents

Publication Publication Date Title
MX2020003815A (es) Sintesis de cantaridina.
AR114631A1 (es) Métodos e intermedios para preparar compuestos de piridina
BR112022008144A2 (pt) Processo para a produção de um composto, cristal de piroxassulfona, composição agroquímica, e, uso de um composto
CL2004000687A1 (es) Procedimiento para la preparacion de telmisartan.
UY33682A (es) ?producción de carbonato de calcio precipitado de alta pureza?.
AR092278A1 (es) Proceso de obtencion de derivados n-acilicos de bifenil-alanina e intermediarios relacionados
EP4169924A3 (en) Synthesis of halichondrins
CO6321248A2 (es) Derivados de triazol utiles para el tratamiento de enfermedades
PE20120617A1 (es) Procesos para preparar cobicistat y sus productos intermedios
AR116790A1 (es) PROCEDIMIENTO PARA LA PREPARACIÓN DE 3a-HIDROXI-5a-PREGNAN-20-ONA (BREXANOLONA)
ECSP088773A (es) Derivados de amida y su aplicación para el tratamiento de enfermedades relacionadas con proteína-g
AR116423A1 (es) Un proceso de fabricación de compuestos heterocíclicos de 2-nitroimino
AR113808A1 (es) Método para la preparación de compuestos intermedios de azoxistrobina
BR112017020484A2 (pt) método para a fabricação de novo composto contendo nitrogênio ou sal do mesmo e intermediário de fabricação do novo composto contendo nitrogênio ou sal do mesmo
ECSP088383A (es) Tetrahidroquinolinas, su síntesis e intermediarios campo de la invención
MX2017001459A (es) Sintesis de fosforamidatos.
AR118647A1 (es) Proceso de preparación de 2-(3,5-diclorofenil)-6-benzoxazolcarboxilato de 1-deoxi-1-metilamino-d-glucitol
GT200600207A (es) Proceso para la síntesis de compuestos orgánicos
AR121483A1 (es) Hidrato cristalino de un compuesto inhibidor de jak
AR107494A1 (es) Proceso para la preparación de osimertinib (azd9291) o una sal del mismo, y “azd9291 anilina” o una sal de la misma
Maghsoodlou et al. An efficient synthesis of α‐Amino phosphonates using silica sulfuric acid as a heterogeneous catalyst
AR117834A1 (es) Complejo de gadolinio y un ligando quelatante derivado de pcta diastereoisoméricamente enriquecido y método de síntesis
BR112021018733A2 (pt) Composições de d-metirosina e métodos para preparar as mesmas
CL2019002795A1 (es) Proceso para preparar 2-exo-(2-metilbenciloxi)-1-metil-4-isopropil-7-oxabiciclo[2.2.1]heptano.
BR112022009688A2 (pt) Processo para a síntese de (3-cloro-2-piridil)hidrazina