HRP20211927T1 - Derivati spojenih pentacikličnih imidazola kao modulatori aktivnosti tnf - Google Patents
Derivati spojenih pentacikličnih imidazola kao modulatori aktivnosti tnf Download PDFInfo
- Publication number
- HRP20211927T1 HRP20211927T1 HRP20211927TT HRP20211927T HRP20211927T1 HR P20211927 T1 HRP20211927 T1 HR P20211927T1 HR P20211927T T HRP20211927T T HR P20211927TT HR P20211927 T HRP20211927 T HR P20211927T HR P20211927 T1 HRP20211927 T1 HR P20211927T1
- Authority
- HR
- Croatia
- Prior art keywords
- methanobenzimidazo
- benzodiazocin
- difluoromethoxy
- amino
- methyl
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- UROFXMLQPAUCGV-WOJBJXKFSA-N (1R,11R)-5-[2-(1-aminocyclobutyl)pyrimidin-5-yl]-18-(difluoromethoxy)-12-methyl-2,9,12-triazapentacyclo[9.8.1.02,10.03,8.014,19]icosa-3(8),4,6,9,14(19),15,17-heptaen-13-one Chemical compound CN1[C@@H]2C[C@H](c3c(OC(F)F)cccc3C1=O)n1c2nc2ccc(cc12)-c1cnc(nc1)C1(N)CCC1 UROFXMLQPAUCGV-WOJBJXKFSA-N 0.000 claims 1
- SFCCDCHZSHIFBN-UPCIGPOOSA-N (1R,11R)-5-[6-[(1R,2S)-1-amino-2-methylcyclobutyl]-5-fluoropyridin-3-yl]-18-(difluoromethoxy)-2,9,12-triazapentacyclo[9.8.1.02,10.03,8.014,19]icosa-3(8),4,6,9,14(19),15,17-heptaen-13-one Chemical compound N[C@]1([C@H](CC1)C)C1=C(C=C(C=N1)C=1C=CC2=C(C=1)N1[C@H]3C4=C(C(N[C@@H](C1=N2)C3)=O)C=CC=C4OC(F)F)F SFCCDCHZSHIFBN-UPCIGPOOSA-N 0.000 claims 1
- SFCCDCHZSHIFBN-GCOUEFSDSA-N (1R,11R)-5-[6-[(1S,2R)-1-amino-2-methylcyclobutyl]-5-fluoropyridin-3-yl]-18-(difluoromethoxy)-2,9,12-triazapentacyclo[9.8.1.02,10.03,8.014,19]icosa-3(8),4,6,9,14(19),15,17-heptaen-13-one Chemical compound C[C@@H]1CC[C@@]1(N)C1=C(F)C=C(C=N1)C1=CC2=C(C=C1)N=C1[C@H]3C[C@@H](N21)C1=C(C=CC=C1OC(F)F)C(=O)N3 SFCCDCHZSHIFBN-GCOUEFSDSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- -1 cyano, hydroxy Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 230000003040 nociceptive effect Effects 0.000 claims 1
- 230000000771 oncological effect Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- 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
- C07D487/12—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 three hetero rings
- C07D487/18—Bridged 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- 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
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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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)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (8)
1. Spoj formule (I), ili njegova farmaceutski prihvatljiva sol:
[image]
gdje
X predstavlja N ili C-F;
R1 predstavlja vodik ili metil ;
R2 predstavlja vodik, metil ili trifluorometil ; i R3 predstavlja vodik, cijano, hidroksi ili hidroksimetil.
2. Spoj prema zahtjevu 1 predstavljeno formulom (IIA), ili njegova farmaceutski prihvatljiva sol:
[image]
gdje X, R1, R2 i R3 su kao što je definirano u zahtjevu 1.
3. Spoj prema zahtjevu 1 predstavljeno formulom (IIB), ili njegova farmaceutski prihvatljiva sol:
[image]
gdje X, R1, R2 i R3 su kao što je definirano u zahtjevu 1.
4. Spoj prema zahtjevu 1 koje je izabrano od sljedećih:
cis-3-amino-3-{5-[(7R,14R)-1-(difluorometoksi)-6-metil-5-okso-5,6,7,14-tetrahidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-11-il]pirimidin-2-il}-1-Metil ciklobutankarbonitrila;
cis-3-amino-3-{5-[(7R,14R)-1-(difluorometoksi)-5-okso-5,6,7,14-tetrahidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-11-il]pirimidin-2-il}-1-metil ciklobutankarbonitrila;
cis-3-amino-3-{5-[(7R,14R)-1-(difluorometoksi)-6-metil-5-okso-5,6,7,14-tetrahidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-11-il]-3-fluoropiridin-2-il}-1-metil ciklobutankarbonitrila;
cis-3-amino-3-{5-[(7R,14R)-1-(difluorometoksi)-5-okso-5,6,7,14-tetrahidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-11-il]-3-fluoropiridin-2-il}-1-metil ciklobutankarbonitrila;
(7R,14R)-11-{6-[(1S,2R)-1-amino-2-metilciklobutil]-5-fluoropiridin-3-il}-1-(diflourometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-ona;
(7R,14R)-11-{6-[(1R,2S)-1-amino-2-metilciklobutil]-5-fluoropiridin-3-il}-1-(diflourometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-[2-(1-aminociklobutil)pirimidin-5-il]-1-(difluorometoksi)-6-metil-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-ona;
(7R,14R)-11-[6-(cis-1-amino-3-hidroksi-3-metilciklobutil)-5-fluoropiridin-3-il]-1-(difluorometoksi)-6-metil-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-[6-(cis-1-amino-3-hidroksi-3-metilciklobutil)-5-fluoropiridin-3-il]-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-ona;
(7R,14R)-11-{2-[cis-1-amino-3-(hidroksimetil)-3-metilciklobutil]pirimidin-5-il}-1-(difluorometoksi)-6-metil-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-(6-[cis-1-amino-3-(hidroksimetil)-3-metilciklobutil]-5-fluoropiridin-3-il}-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-(6-[cis-1-amino-3-hidroksi-3-(trifluorometil)ciklobutil]-5-fluoropiridin-3-il}-1-(difluorometoksi)-6-metil-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-{2-[cis-1-amino-3-hidroksi-3-(trifluorometil)ciklobutil]pirimidin-5-il}-1-(difluorometoksi)-6-metil-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-(6-[cis-1-amino-3-hidroksi-3-(trifluorometil)ciklobutil]-5-fluoropiridin-3-il}-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-(2-{cis-1-amino-3-[hidroksi(dideutero)metil ]-3-metil ciklobutil}-pirimidin-5-il)-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]-benzodiazocin-5(14H)-ona;
(7R,14R)-11-{2-[cis-1-amino-3-(hidroksimetil)-3-metilciklobutil]pirimidin-5il}-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b][2,5]benzodiazocin-5(14H)-ona; i
(7R,14R)-11-(6-{cis-1-amino-3-[hidroksi(dideutero)metil]-3-metilciklobutil}-5-fluoropiridin-3-il)-1-(difluorometoksi)-6,7-dihidro-7,14-metanobenzimidazo[1,2-b]-[2,5]benzodiazocin-5(14H)-ona.
5. Spoj formule (I) kao što je definirano u zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, za upotrebu u terapiji.
6. Spoj formule (I) kao što je definirano u zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, za upotrebu u liječenju i/ili prevenciji upalnog ili autoimunog poremećaja, neurološkog ili neurodegenerativnog poremećaja, boli ili nociceptivnog poremećaja, kardiovaskularnog poremećaja, metaboličkog poremećaja, očnog poremećaja, ili onkološkog poremećaja.
7. Farmaceutski sastav koja sadrži spoj formule (I) kao što je definirano u zahtjevu 1, ili njegovu farmaceutski prihvatljivu sol, zajedno sa farmaceutski prihvatljivim nosačem.
8. Farmaceutski sastav prema zahtjevu 7, koji dalje sadrži dodatni farmaceutski aktivni sastojak.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP17168027 | 2017-04-25 | ||
EP18719178.8A EP3615534B1 (en) | 2017-04-25 | 2018-04-24 | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
PCT/EP2018/060489 WO2018197503A1 (en) | 2017-04-25 | 2018-04-24 | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20211927T1 true HRP20211927T1 (hr) | 2022-03-18 |
Family
ID=58632834
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Application Number | Title | Priority Date | Filing Date |
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HRP20211927TT HRP20211927T1 (hr) | 2017-04-25 | 2018-04-24 | Derivati spojenih pentacikličnih imidazola kao modulatori aktivnosti tnf |
Country Status (34)
Country | Link |
---|---|
US (3) | US10980814B2 (hr) |
EP (2) | EP3939980B1 (hr) |
JP (2) | JP7083358B2 (hr) |
KR (1) | KR102565132B1 (hr) |
CN (1) | CN110582495B (hr) |
AR (1) | AR111426A1 (hr) |
AU (1) | AU2018259040B2 (hr) |
BR (1) | BR112019020314A2 (hr) |
CA (1) | CA3058980A1 (hr) |
CL (1) | CL2019002875A1 (hr) |
CO (1) | CO2019012856A2 (hr) |
CR (1) | CR20190526A (hr) |
DK (1) | DK3615534T3 (hr) |
EA (1) | EA039049B1 (hr) |
ES (2) | ES2956555T3 (hr) |
HR (1) | HRP20211927T1 (hr) |
HU (1) | HUE056593T2 (hr) |
IL (1) | IL269890B (hr) |
LT (1) | LT3615534T (hr) |
MA (2) | MA49055B1 (hr) |
MX (1) | MX2019012443A (hr) |
MY (1) | MY197212A (hr) |
NZ (1) | NZ758198A (hr) |
PE (1) | PE20200662A1 (hr) |
PH (1) | PH12019502182A1 (hr) |
PL (2) | PL3939980T3 (hr) |
PT (2) | PT3939980T (hr) |
RS (1) | RS62596B1 (hr) |
SG (1) | SG11201908871SA (hr) |
SI (1) | SI3615534T1 (hr) |
TW (1) | TWI801378B (hr) |
UY (1) | UY37700A (hr) |
WO (1) | WO2018197503A1 (hr) |
ZA (1) | ZA201906255B (hr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6968089B2 (ja) * | 2016-04-01 | 2021-11-17 | ユーシービー バイオファルマ エスアールエル | Tnf活性のモジュレーターとしての縮合六環式イミダゾール誘導体 |
WO2020084008A1 (en) * | 2018-10-24 | 2020-04-30 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US9550737B2 (en) * | 2012-06-11 | 2017-01-24 | Ucb Biopharma Sprl | TNF -α modulating benzimidazoles |
GB201212513D0 (en) * | 2012-07-13 | 2012-08-29 | Ucb Pharma Sa | Therapeutic agents |
WO2014009295A1 (en) * | 2012-07-13 | 2014-01-16 | Ucb Pharma S.A. | Imidazopyridine derivatives as modulators of tnf activity |
GB201321728D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
MA40770B1 (fr) * | 2014-10-03 | 2021-11-30 | Sanofi Sa | Dérivés d'imidazoles pentacyclic fusionnés |
US9856253B2 (en) | 2015-04-17 | 2018-01-02 | Abbvie, Inc. | Tricyclic modulators of TNF signaling |
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2018
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- 2018-04-24 WO PCT/EP2018/060489 patent/WO2018197503A1/en unknown
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- 2018-04-24 US US16/497,217 patent/US10980814B2/en active Active
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- 2018-04-25 AR ARP180101067A patent/AR111426A1/es unknown
- 2018-04-25 UY UY0001037700A patent/UY37700A/es not_active Application Discontinuation
- 2018-08-24 MA MA57699A patent/MA57699B1/fr unknown
-
2019
- 2019-09-20 ZA ZA2019/06255A patent/ZA201906255B/en unknown
- 2019-09-23 PH PH12019502182A patent/PH12019502182A1/en unknown
- 2019-10-07 IL IL269890A patent/IL269890B/en unknown
- 2019-10-09 CL CL2019002875A patent/CL2019002875A1/es unknown
- 2019-11-18 CO CONC2019/0012856A patent/CO2019012856A2/es unknown
-
2021
- 2021-02-15 US US17/176,018 patent/US20210252012A1/en not_active Abandoned
-
2022
- 2022-05-31 JP JP2022088172A patent/JP7299382B2/ja active Active
-
2023
- 2023-02-27 US US18/175,030 patent/US20230250105A1/en active Pending
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