ES2578363B1 - Moduladores de los receptores A3 de adenosina - Google Patents

Moduladores de los receptores A3 de adenosina Download PDF

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Publication number
ES2578363B1
ES2578363B1 ES201530085A ES201530085A ES2578363B1 ES 2578363 B1 ES2578363 B1 ES 2578363B1 ES 201530085 A ES201530085 A ES 201530085A ES 201530085 A ES201530085 A ES 201530085A ES 2578363 B1 ES2578363 B1 ES 2578363B1
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Spain
Prior art keywords
group
acid
thiazol
cyano
ylcarbamoyl
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Application number
ES201530085A
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English (en)
Spanish (es)
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ES2578363A1 (es
Inventor
Julio CASTRO- PALOMINO LÁRIA
Juan CAMACHO GÓMEZ
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Palobiofarma SL
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Palobiofarma SL
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
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Priority to ES201530085A priority Critical patent/ES2578363B1/es
Application filed by Palobiofarma SL filed Critical Palobiofarma SL
Priority to PT167046804T priority patent/PT3248964T/pt
Priority to CA2974596A priority patent/CA2974596C/en
Priority to EA201791657A priority patent/EA031627B1/ru
Priority to LTEP16704680.4T priority patent/LT3248964T/lt
Priority to MEP-2019-265A priority patent/ME03570B/me
Priority to BR112017015597-4A priority patent/BR112017015597B1/pt
Priority to HRP20191779TT priority patent/HRP20191779T1/hr
Priority to US15/544,429 priority patent/US10238637B2/en
Priority to PCT/ES2016/070032 priority patent/WO2016116652A1/es
Priority to SM20190554T priority patent/SMT201900554T1/it
Priority to SI201630442T priority patent/SI3248964T1/sl
Priority to RSP20191282 priority patent/RS59388B1/sr
Priority to JP2017538582A priority patent/JP6637983B2/ja
Priority to ES16704680T priority patent/ES2750030T3/es
Priority to KR1020177023348A priority patent/KR102424575B1/ko
Priority to AU2016210091A priority patent/AU2016210091B2/en
Priority to MX2017009514A priority patent/MX2017009514A/es
Priority to EP16704680.4A priority patent/EP3248964B1/en
Priority to HUE16704680A priority patent/HUE046307T2/hu
Priority to CN201680006653.8A priority patent/CN107207445B/zh
Priority to DK16704680.4T priority patent/DK3248964T3/da
Priority to PL16704680T priority patent/PL3248964T3/pl
Publication of ES2578363A1 publication Critical patent/ES2578363A1/es
Application granted granted Critical
Publication of ES2578363B1 publication Critical patent/ES2578363B1/es
Priority to CY20191101070T priority patent/CY1122172T1/el
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/549—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 sulfur as the ring hetero atoms, e.g. sulthiame having two or more nitrogen atoms in the same ring, e.g. hydrochlorothiazide

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
ES201530085A 2015-01-22 2015-01-22 Moduladores de los receptores A3 de adenosina Active ES2578363B1 (es)

Priority Applications (24)

Application Number Priority Date Filing Date Title
ES201530085A ES2578363B1 (es) 2015-01-22 2015-01-22 Moduladores de los receptores A3 de adenosina
JP2017538582A JP6637983B2 (ja) 2015-01-22 2016-01-22 アデノシンａ３受容体の調節剤
EA201791657A EA031627B1 (ru) 2015-01-22 2016-01-22 Модуляторы аденозиновых рецепторов a
LTEP16704680.4T LT3248964T (lt) 2015-01-22 2016-01-22 A3 adenozino receptorių tiazolo moduliatoriai
KR1020177023348A KR102424575B1 (ko) 2015-01-22 2016-01-22 아데노신 ａ₃수용체의 조절제
BR112017015597-4A BR112017015597B1 (pt) 2015-01-22 2016-01-22 Composto modulador do receptor da adenosina a3, composição farmacêutica, uso e combinação deste
HRP20191779TT HRP20191779T1 (hr) 2015-01-22 2016-01-22 Tiazolski modulatori adenozinskih receptora a3
US15/544,429 US10238637B2 (en) 2015-01-22 2016-01-22 Modulators of the adenosine A3 receptors
PCT/ES2016/070032 WO2016116652A1 (es) 2015-01-22 2016-01-22 Moduladores de los receptores a3 de adenosina
SM20190554T SMT201900554T1 (it) 2015-01-22 2016-01-22 Modulatori tiazolici dei recettori dell'adenosina a3
SI201630442T SI3248964T1 (sl) 2015-01-22 2016-01-22 Tiazolovi modulatorji A3 adenozinskega receptorja
RSP20191282 RS59388B1 (sr) 2015-01-22 2016-01-22 Tiazolni modulatori a3 adenozinskih receptora
PT167046804T PT3248964T (pt) 2015-01-22 2016-01-22 Moduladores tiazólicos de recetores a3 de adenosina
ES16704680T ES2750030T3 (es) 2015-01-22 2016-01-22 Moduladores De Los Receptores A3 De Adenosina
MEP-2019-265A ME03570B (me) 2015-01-22 2016-01-22 Tiazolni modulatori a3 adenozinskih receptora
AU2016210091A AU2016210091B2 (en) 2015-01-22 2016-01-22 Modulators of the adenosine A3 receptors
MX2017009514A MX2017009514A (es) 2015-01-22 2016-01-22 Moduladores de los receptores a3 de adenosina.
EP16704680.4A EP3248964B1 (en) 2015-01-22 2016-01-22 Thiazole modulators of a3 adenosine receptors
HUE16704680A HUE046307T2 (hu) 2015-01-22 2016-01-22 A3 adenozin receptorok tiazol modulátorai
CA2974596A CA2974596C (en) 2015-01-22 2016-01-22 Modulators of the adenosine a3 receptors
DK16704680.4T DK3248964T3 (da) 2015-01-22 2016-01-22 Thiazol-modulatorer af A3-adenosinreceptorer
PL16704680T PL3248964T3 (pl) 2015-01-22 2016-01-22 Tiazolowe modulatory receptorów adenozynowych a3
CN201680006653.8A CN107207445B (zh) 2015-01-22 2016-01-22 腺苷a3受体的调节剂
CY20191101070T CY1122172T1 (el) 2015-01-22 2019-10-11 Τροποποιητες θειαζολης των a3 υποδοχεων αδενοσινης

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES201530085A ES2578363B1 (es) 2015-01-22 2015-01-22 Moduladores de los receptores A3 de adenosina

Publications (2)

Publication Number Publication Date
ES2578363A1 ES2578363A1 (es) 2016-07-26
ES2578363B1 true ES2578363B1 (es) 2017-01-31

Family

ID=55359537

Family Applications (2)

Application Number Title Priority Date Filing Date
ES201530085A Active ES2578363B1 (es) 2015-01-22 2015-01-22 Moduladores de los receptores A3 de adenosina
ES16704680T Active ES2750030T3 (es) 2015-01-22 2016-01-22 Moduladores De Los Receptores A3 De Adenosina

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES16704680T Active ES2750030T3 (es) 2015-01-22 2016-01-22 Moduladores De Los Receptores A3 De Adenosina

Country Status (23)

Country Link
US (1) US10238637B2 (enExample)
EP (1) EP3248964B1 (enExample)
JP (1) JP6637983B2 (enExample)
KR (1) KR102424575B1 (enExample)
CN (1) CN107207445B (enExample)
AU (1) AU2016210091B2 (enExample)
BR (1) BR112017015597B1 (enExample)
CA (1) CA2974596C (enExample)
CY (1) CY1122172T1 (enExample)
DK (1) DK3248964T3 (enExample)
EA (1) EA031627B1 (enExample)
ES (2) ES2578363B1 (enExample)
HR (1) HRP20191779T1 (enExample)
HU (1) HUE046307T2 (enExample)
LT (1) LT3248964T (enExample)
ME (1) ME03570B (enExample)
MX (1) MX2017009514A (enExample)
PL (1) PL3248964T3 (enExample)
PT (1) PT3248964T (enExample)
RS (1) RS59388B1 (enExample)
SI (1) SI3248964T1 (enExample)
SM (1) SMT201900554T1 (enExample)
WO (1) WO2016116652A1 (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2676535B1 (es) * 2017-01-20 2019-04-29 Palobiofarma Sl Moduladores de los receptores a3 de adenosina
KR102155406B1 (ko) 2017-08-18 2020-09-11 주식회사 엘지화학 아연철산화물 내 잔류 Cl의 정량분석 방법
US11458974B2 (en) * 2019-07-08 2022-10-04 Toyota Motor Engineering & Manufacturing North America, Inc. Fleet-based average lane change and driver-specific behavior modelling for autonomous vehicle lane change operation
IT202300014340A1 (it) * 2023-07-10 2025-01-10 Consiglio Nazionale Ricerche Trattamento di malattie associate alla disfunzione del gene ocrl.

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