CA2935899C - Fluorinated cbd compounds, compositions and uses thereof - Google Patents

Fluorinated cbd compounds, compositions and uses thereof Download PDF

Info

Publication number
CA2935899C
CA2935899C CA2935899A CA2935899A CA2935899C CA 2935899 C CA2935899 C CA 2935899C CA 2935899 A CA2935899 A CA 2935899A CA 2935899 A CA2935899 A CA 2935899A CA 2935899 C CA2935899 C CA 2935899C
Authority
CA
Canada
Prior art keywords
branched
straight
disease
compound according
alkyl
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
CA2935899A
Other languages
English (en)
French (fr)
Other versions
CA2935899A1 (en
Inventor
Raphael Mechoulam
Antonio Waldo ZUARDI
Flavio Pereira KAPCZINSKI
Jaime Eduardo Cecilio HALLAK
Francisco Silveira GUIMARAES
Jose Alexandre de Souza CRIPPA
Aviva Breuer
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.)
Universidade de São Paulo
Federal University of Rio Grande do Sul
Yissum Research Development Co of Hebrew University of Jerusalem
Original Assignee
Universidade de São Paulo
Federal University of Rio Grande do Sul
Yissum Research Development Co of Hebrew University of Jerusalem
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 Universidade de São Paulo, Federal University of Rio Grande do Sul, Yissum Research Development Co of Hebrew University of Jerusalem filed Critical Universidade de São Paulo
Publication of CA2935899A1 publication Critical patent/CA2935899A1/en
Application granted granted Critical
Publication of CA2935899C publication Critical patent/CA2935899C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A61K31/055—Phenols the aromatic ring being substituted by halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/373—Halogenated derivatives with all hydroxy groups on non-condensed rings and with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/16—Acetic acid esters of dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Addiction (AREA)
  • Ophthalmology & Optometry (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Biochemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Toxicology (AREA)
CA2935899A 2013-01-08 2014-01-08 Fluorinated cbd compounds, compositions and uses thereof Active CA2935899C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361750043P 2013-01-08 2013-01-08
US61/750,043 2013-01-08
PCT/IL2014/050023 WO2014108899A1 (en) 2013-01-08 2014-01-08 Fluorinated cbd compounds, compositions and uses thereof

Publications (2)

Publication Number Publication Date
CA2935899A1 CA2935899A1 (en) 2014-07-17
CA2935899C true CA2935899C (en) 2021-08-31

Family

ID=50272668

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2935899A Active CA2935899C (en) 2013-01-08 2014-01-08 Fluorinated cbd compounds, compositions and uses thereof

Country Status (9)

Country Link
US (3) US9447019B2 (enExample)
EP (1) EP2943463B1 (enExample)
JP (3) JP6228230B2 (enExample)
CN (1) CN105209424B (enExample)
AU (2) AU2014206036B2 (enExample)
CA (1) CA2935899C (enExample)
ES (1) ES2894836T3 (enExample)
MX (1) MX381719B (enExample)
WO (1) WO2014108899A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2014206036B2 (en) 2013-01-08 2017-11-02 Universidade De Sao Paulo - Usp Fluorinated CBD compounds, compositions and uses thereof
GB2531282A (en) 2014-10-14 2016-04-20 Gw Pharma Ltd Use of cannabinoids in the treatment of epilepsy
GB2539472A (en) 2015-06-17 2016-12-21 Gw Res Ltd Use of cannabinoids in the treatment of epilepsy
AU2016293387A1 (en) * 2015-07-16 2018-01-25 Universidade De São Paulo - Usp Flourinated CBD compounds, compositions and uses thereof
US11207414B2 (en) 2015-09-22 2021-12-28 Graphium Biosciences, Inc. Cannabinoid glycoside prodrugs and methods of synthesis
MX2018004632A (es) * 2015-10-16 2018-11-09 Scythian Biosciences Inc Metodos y composiciones para el tratamiento de una lesion cerebral traumatica.
US10239808B1 (en) 2016-12-07 2019-03-26 Canopy Holdings, LLC Cannabis extracts
EP3634390B1 (en) 2017-05-09 2023-09-27 Graphium Biosciences, Inc. Antimicrobial compositions comprising cbd or thc against c. difficile infection or e. faecalis
CA3065167A1 (en) * 2017-05-31 2018-12-06 Phytecs, Inc. Pharmaceutical compositions comprising cannabidiol and beta-caryophyllene and methods for their use
CA3300266A1 (en) 2017-09-28 2026-03-02 Harmony Biosciences Management, Inc. Treatment of fragile x syndrome with cannabidiol
GB2568929A (en) 2017-12-01 2019-06-05 Gw Res Ltd Use of cannabinoids in the treatment of epilepsy
US11202771B2 (en) 2018-01-31 2021-12-21 Treehouse Biotech, Inc. Hemp powder
IL325123A (en) 2018-12-14 2026-02-01 Harmony Biosciences Man Inc Treating 22q11.2 Deficiency Syndrome with Cannabidiol
EP4069215B1 (en) 2019-12-06 2026-07-01 Jlabs Beauty LLC Topical compositions containing rose oil and cannabidiol, and processes for their preparation and use
CA3173339A1 (en) 2020-02-26 2021-09-02 Graphium Biosciences, Inc. Novel cannabinoid glycosides and uses thereof
GB202002754D0 (en) 2020-02-27 2020-04-15 Gw Res Ltd Methods of treating tuberous sclerosis complex with cannabidiol and everolimus
EP4153306A4 (en) 2020-05-22 2024-06-26 Ilera Derm LLC Compositions for treating acne and dermatological conditions
GB202009321D0 (en) 2020-06-18 2020-08-05 Gw Res Ltd Use of cannabinoids in the treatment of epilepsy
GB2642523A (en) * 2024-07-12 2026-01-14 Sonas Pharmaceuticals N I Ltd Novel halogenated cannabinoid derivatives

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6566560B2 (en) 1999-03-22 2003-05-20 Immugen Pharmaceuticals, Inc. Resorcinolic compounds
DK2176208T3 (en) * 2007-07-30 2015-04-27 Zynerba Pharmaceuticals Inc Prodrugs of cannabidiol, compositions containing prodrugs of cannabidiol and methods of use thereof
WO2011006099A1 (en) * 2009-07-10 2011-01-13 Northeastern University Angiogenic resorcinol derivatives
PT2473475T (pt) * 2009-08-31 2017-08-02 Zynerba Pharmaceuticals Inc Utilização de profármacos de canabidiol na administração tópica e transdérmica com microagulhas
WO2012011112A1 (en) * 2010-07-22 2012-01-26 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Non psychoactive cannabinoids and uses thereof
AU2014206036B2 (en) 2013-01-08 2017-11-02 Universidade De Sao Paulo - Usp Fluorinated CBD compounds, compositions and uses thereof

Also Published As

Publication number Publication date
WO2014108899A1 (en) 2014-07-17
US20150344403A1 (en) 2015-12-03
CA2935899A1 (en) 2014-07-17
AU2018200570B2 (en) 2019-09-26
AU2014206036A2 (en) 2016-06-16
AU2014206036A1 (en) 2015-08-13
CN105209424B (zh) 2019-12-13
US20170326078A1 (en) 2017-11-16
JP6952727B2 (ja) 2021-10-20
EP2943463B1 (en) 2021-07-14
EP2943463A1 (en) 2015-11-18
MX2015008766A (es) 2016-03-07
HK1214586A1 (zh) 2016-07-29
JP2016505614A (ja) 2016-02-25
ES2894836T3 (es) 2022-02-16
US20170197904A1 (en) 2017-07-13
JP6228230B2 (ja) 2017-11-08
US9782360B2 (en) 2017-10-10
US10441553B2 (en) 2019-10-15
US9447019B2 (en) 2016-09-20
JP2018065794A (ja) 2018-04-26
AU2014206036B2 (en) 2017-11-02
AU2018200570A1 (en) 2018-02-15
CN105209424A (zh) 2015-12-30
MX381719B (es) 2025-03-12
JP2019073547A (ja) 2019-05-16

Similar Documents

Publication Publication Date Title
AU2018200570B2 (en) Fluorinated cbd compounds, compositions and uses thereof
US20190084909A1 (en) Fluorinated cbd compounds, compositions and uses thereof
ES2332009T3 (es) Formas cristalinas de hidrocloruro de (r)-8-cloro-1-metil-2,3,4,5-tetrahidro-1h-3-benzazepina.
ES2736507T3 (es) 2-Tioxo-imidazolidin-4-onas sustituidas y análogos espiro de las mismas, ingrediente activo contra el cáncer, composición farmacéutica, preparación medicinal, método para tratar cáncer de próstata
CN106478502B (zh) 1,2,3,4-四氢异喹啉衍生物、其制备方法和应用
EP1727817B1 (en) Azabicyclooctan-3-one derivatives and use thereof
KR102784814B1 (ko) 항불안제 제조시 치환된 신남아미드 유도체의 적용
CN105658634A (zh) 作为TCR-Nck相互作用的抑制剂的被醇盐取代的色烯衍生物
TW202102502A (zh) 作為流感病毒複製抑制劑之稠合多環吡啶酮化合物
HK1214586B (en) Fluorinated cbd compounds, compositions and uses thereof
CN102617448B (zh) 4-甲氧甲基-4-(n-丙酰基)苯胺哌啶类化合物、制备方法及用途
BR112015016492B1 (pt) Compostos cbd fluorados, composições e usos
CN102617449B (zh) 4-取代-4-(n-丙酰基)苯胺哌啶类化合物、制备方法及用途
RU2323210C9 (ru) Замещенные эфиры 1н-индол-3-карбоновой кислоты, фармацевтическая композиция, способ их получения и применения
CN103121970A (zh) 苯并咪唑及其衍生物,其药物组合物及其在制备抗抑郁药物中的应用
US9999613B2 (en) 2H-chromene derivatives as analgesic agents
HK40032676A (en) Fused polycyclic pyridone compounds as influenza virus replication inhibitors
WO2018209062A1 (en) Prodrug derivatives of protein kinase c modulators

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190107

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 11TH ANNIV.) - STANDARD

Year of fee payment: 11

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241215

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241215

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241215

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 12TH ANNIV.) - STANDARD

Year of fee payment: 12

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251228

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20260105