WO2013110309A1 - Triazolo[4,5-d]pyrimidine derivatives - Google Patents

Triazolo[4,5-d]pyrimidine derivatives Download PDF

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Publication number
WO2013110309A1
WO2013110309A1 PCT/EP2012/005358 EP2012005358W WO2013110309A1 WO 2013110309 A1 WO2013110309 A1 WO 2013110309A1 EP 2012005358 W EP2012005358 W EP 2012005358W WO 2013110309 A1 WO2013110309 A1 WO 2013110309A1
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WO
WIPO (PCT)
Prior art keywords
pyrazol
pyrimidin
triazolo
amine
phenyl
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.)
Ceased
Application number
PCT/EP2012/005358
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English (en)
French (fr)
Inventor
Dieter Dorsch
Guenter Hoelzemann
Kai Schiemann
Ansgar Wegener
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 to CA2862694A priority Critical patent/CA2862694C/en
Priority to US14/375,067 priority patent/US9409914B2/en
Priority to AU2012367141A priority patent/AU2012367141B2/en
Priority to JP2014553622A priority patent/JP6063482B2/ja
Priority to SG11201404234YA priority patent/SG11201404234YA/en
Priority to ES12816002.5T priority patent/ES2655264T3/es
Priority to CN201280068233.4A priority patent/CN104066734B/zh
Priority to EP12816002.5A priority patent/EP2807161B1/en
Priority to MX2014008864A priority patent/MX2014008864A/es
Priority to KR1020147023872A priority patent/KR20140117636A/ko
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to BR112014016884A priority patent/BR112014016884A2/pt
Publication of WO2013110309A1 publication Critical patent/WO2013110309A1/en
Priority to IL233808A priority patent/IL233808B/en
Anticipated expiration legal-status Critical
Priority to ZA2014/06323A priority patent/ZA201406323B/en
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
    • A61K31/535—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
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/28—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
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the substrate analogue 1 methyl-tryptophan (1MT) and related molecules have been used widely to target IDO in the cancer context and other settings.
  • 1MT was unable to elicit tumor regression in several tumor models, suggesting only modest antitumor efficacy when IDO inhibition was applied as a monotherapy.
  • the combinatory treatment with 1MT and a variety of cytotoxic chemotherapeutic agents elicited regression of established MMTV-neu/HER2 tumors, which responded poorly to any single-agent therapy [Muller et al 2005a].
  • the elF2 kinase GCN2 is activated by interacting with deacylated tRNA that is accumulating as direct consequence of nutritional deprivation stress.
  • Other cellular stress factors like UV irridation, redox stress or proteasome inhibition can induce GCN2 activation indirectly [Wek et al 2006].
  • elF2a becomes phosphorylated and this induces the specific expression of stress related target genes mainly by cap- independent initiation via the activating transcription factor 4 (ATF4).
  • the combination of inhibitory activities on GCN2 particularly with inhibition of FLT3 could be advantageous for the treatment of neurodegenerative disorders as it could synergize suppressive effects on inflammatory processes with the modulation of protein deposites generation in the brain.
  • the combination of inhibitory activities on GCN2 particularly with inhibition of FLT3 could provide advantages for modulating the immune response to treat immune related disorders and inflammatory or autoimmune diseases.
  • the compounds of the formula I can furthermore be used for the isolation and investigation of the activity or expression of SykGCN2, FMS (CSF1R), FLT3 or FLT4. In addition, they are particularly suitable for use in diagnostic methods for diseases in connection with unregulated or disturbed SykGCN2, FMS (CSF1R), FLT3 or FLT4activity.
  • the host or patient can belong to any mammalian species, for example a primate species, particularly humans;
  • kinase inhibitors For the identification of kinase inhibitors, various assay systems are available. In scintillation proximity assay (Sorg et al., J. of. Biomolecular Screening, 2002, 7, 11-19) and flashplate assay, the radioactive phosphorylation of a protein or peptide as substrate with ⁇ is measured. In the presence of an inhibitory compound, a decreased radioactive signal, or none at all, is detectable.
  • A preferably denotes methyl, furthermore ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1 ,1- , 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1- , 2- , 3- or 4-methylpentyl, 1 ,1- , 1 ,2- , 1 ,3- , 2,2- , 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-ethyl-l-methylpropyl, 1-ethyl-2-methylpropyl, 1 ,1 ,2- or 1 ,2,2- trimethylpropyl, furthermore preferably, for example, trifluoromethyl.
  • Cyc preferably denotes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
  • R 2 preferably denotes furyl, thienyl, pyrrolyl, thiadiazolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, triazolyl ortetrazolyl which is unsubstituted or monosubstituted by A, [C(R 3 ) 2 ] p Cyc, [C(R 3 ) 2 ]pAr, [C(R 3 ) 2 ] p Het 1 , CN or [C(R 3 ) 2 ] p COOR 3 .
  • compositions adapted for topical administration can be formulated as ointments, creams, suspensions, lotions, powders, solutions, pastes, gels, sprays, aerosols or oils.
  • the formulations are preferably applied as topical ointment or cream.
  • the active ingredient can be employed either with a paraffinic or a water-miscible cream base.
  • the active ingredient can be formulated to give a cream with an oil-in-water cream base or a water-in-oil base.
  • NSAIDs non-steroidal anti-inflammatory drugs
  • analgesics analgesics
  • the present invention specifically relates to compounds, for the use for the treatment and/or prevention of cancer, where the where the tumour originates from the group of acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia and/or chronic lymphatic leukaemia.
  • TNF-alpha Virulizin (Lorus Therapeu- Revimid (Celgene) agonists/ tics)
  • PCK-3145 apoptosis SRL-172 (T-cell stimulant, promoter, Procyon)
  • immunmodulators preferably with anti-PDL-1- or IL-12.
  • eluent B acetonitrile + 0.04 % formic acid
  • a solution of 100 g of an active ingredient of the formula I and 5 g of disodium hydrogenphosphate in 3 1 of bidistilled water is adjusted to pH 6.5 using 2 N hydrochloric acid, sterile filtered, transferred into injection vials, lyophilised under sterile conditions and sealed under sterile conditions. Each injection vial contains 5 mg of active ingredient.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Obesity (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Biotechnology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Endocrinology (AREA)
  • Hospice & Palliative Care (AREA)
PCT/EP2012/005358 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives Ceased WO2013110309A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
MX2014008864A MX2014008864A (es) 2012-01-28 2012-12-21 Derivados de triazolo[4,5-d]pirimidina.
AU2012367141A AU2012367141B2 (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives
JP2014553622A JP6063482B2 (ja) 2012-01-28 2012-12-21 トリアゾロ［４，５−ｄ］ピリミジン誘導体
SG11201404234YA SG11201404234YA (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives
ES12816002.5T ES2655264T3 (es) 2012-01-28 2012-12-21 Derivados de triazolo[4,5-d]pirimidina
CN201280068233.4A CN104066734B (zh) 2012-01-28 2012-12-21 三唑并[4,5‑d]嘧啶衍生物
EP12816002.5A EP2807161B1 (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives
CA2862694A CA2862694C (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives
US14/375,067 US9409914B2 (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives
KR1020147023872A KR20140117636A (ko) 2012-01-28 2012-12-21 트리아졸로[4,5-ｄ]피리미딘 유도체
BR112014016884A BR112014016884A2 (pt) 2012-01-28 2012-12-21 derivados de triazolo[4,5-d]pirimidina
IL233808A IL233808B (en) 2012-01-28 2014-07-24 History of triazole[5,4-d]pyrimidine and drugs containing them
ZA2014/06323A ZA201406323B (en) 2012-01-28 2014-08-27 Triazolo[4,5-d]pyrimidine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12000558 2012-01-28
EP12000558.2 2012-01-28

Publications (1)

Publication Number Publication Date
WO2013110309A1 true WO2013110309A1 (en) 2013-08-01

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PCT/EP2012/005358 Ceased WO2013110309A1 (en) 2012-01-28 2012-12-21 Triazolo[4,5-d]pyrimidine derivatives

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Country Link
US (1) US9409914B2 (enExample)
EP (1) EP2807161B1 (enExample)
JP (1) JP6063482B2 (enExample)
KR (1) KR20140117636A (enExample)
CN (1) CN104066734B (enExample)
AR (1) AR089810A1 (enExample)
AU (1) AU2012367141B2 (enExample)
BR (1) BR112014016884A2 (enExample)
CA (1) CA2862694C (enExample)
ES (1) ES2655264T3 (enExample)
IL (1) IL233808B (enExample)
MX (1) MX2014008864A (enExample)
SG (1) SG11201404234YA (enExample)
WO (1) WO2013110309A1 (enExample)
ZA (1) ZA201406323B (enExample)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014180524A1 (en) * 2013-05-06 2014-11-13 Merck Patent Gmbh Macrocycles as kinase inhibitors
WO2015038417A1 (en) * 2013-09-10 2015-03-19 Asana Biosciences, Llc Compounds for regulating fak and/or src pathways
KR20190038627A (ko) 2016-08-10 2019-04-08 다케다 야쿠힌 고교 가부시키가이샤 헤테로고리 화합물
KR20200029949A (ko) * 2018-09-11 2020-03-19 재단법인 대구경북첨단의료산업진흥재단 신규 트리아졸로-피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 단백질 키나아제 관련 질환의 예방 또는 치료용 약학적 조성물
WO2021222147A1 (en) * 2020-04-27 2021-11-04 Hibercell, Inc. Heterocyclic gcn2 modulators
US11945799B2 (en) 2020-06-09 2024-04-02 Ip2Ipo Innovations Limited 4-ethynylpyridine derivatives useful as GCN2 inhibitors
KR20250122240A (ko) 2024-02-06 2025-08-13 한미약품 주식회사 신규한 함질소 헤테로고리 유도체 및 이의 용도
WO2025179188A1 (en) * 2024-02-22 2025-08-28 Juno Therapeutics, Inc. Pyrazole-based inhibitors of dna-dependent protein kinase and compositions and applications in gene editing

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
WO2016169504A1 (zh) * 2015-04-24 2016-10-27 广州再极医药科技有限公司 稠环嘧啶氨基衍生物﹑其制备方法、中间体、药物组合物及应用
ES2970715T3 (es) 2016-12-22 2024-05-30 Prec Pharmaceuticals Inc Composiciones y métodos para inhibir la actividad de la arginasa
WO2020070053A1 (en) * 2018-10-01 2020-04-09 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of inhibitors of stress granule formation for targeting the regulation of immune responses
CN120504636B (zh) * 2025-07-22 2025-10-31 江西中医药大学 一种磺胺噻唑-甲氧苄啶药物晶盐及其制备方法和应用

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WO1997030035A1 (en) 1996-02-13 1997-08-21 Zeneca Limited Quinazoline derivatives as vegf inhibitors
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