AU2015204609B2 - Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy - Google Patents
Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy Download PDFInfo
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- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title abstract description 4
- 208000007386 Hepatic Encephalopathy Diseases 0.000 title abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- 239000011780 sodium chloride Substances 0.000 claims 11
- 150000004677 hydrates Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 210000002569 neurons Anatomy 0.000 claims 4
- 230000004112 neuroprotection Effects 0.000 claims 4
- 108009000578 Oxidative Stress Proteins 0.000 claims 3
- 210000002381 Plasma Anatomy 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 230000036542 oxidative stress Effects 0.000 claims 3
- 208000004051 Chronic Traumatic Encephalopathy Diseases 0.000 claims 2
- 230000035492 administration Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- FHEPZBIUHGLJMP-UHFFFAOYSA-N cyclohexene Chemical group [CH]1CCCC=C1 FHEPZBIUHGLJMP-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 108009000433 Amyotrophic lateral sclerosis (ALS) Proteins 0.000 claims 1
- 208000008581 Brain Disease Diseases 0.000 claims 1
- 206010007515 Cardiac arrest Diseases 0.000 claims 1
- 208000008208 Craniocerebral Trauma Diseases 0.000 claims 1
- 206010014623 Encephalopathy Diseases 0.000 claims 1
- 206010014625 Encephalopathy Diseases 0.000 claims 1
- 206010015037 Epilepsy Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000010496 Heart Arrest Diseases 0.000 claims 1
- 201000001971 Huntington's disease Diseases 0.000 claims 1
- 206010070511 Hypoxic-ischaemic encephalopathy Diseases 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- 208000004296 Neuralgia Diseases 0.000 claims 1
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 1
- VWVIOABMCXYUAS-RBUKOAKNSA-N OC=1C=C(CC2CN(C2)C(C)=O)C=C(C1[C@@H]1C=C(CC[C@H]1C(=C)C)C)O Chemical compound OC=1C=C(CC2CN(C2)C(C)=O)C=C(C1[C@@H]1C=C(CC[C@H]1C(=C)C)C)O VWVIOABMCXYUAS-RBUKOAKNSA-N 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- KVVMXWRFYAGASO-UHFFFAOYSA-M azetidine-1-carboxylate Chemical compound [O-]C(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-M 0.000 claims 1
- 125000004431 deuterium atoms Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000001037 epileptic Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- 229960001755 resorcinol Drugs 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 230000000472 traumatic Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 239000004090 neuroprotective agent Substances 0.000 abstract description 2
- 0 C*(CC(C)(C)c1cc(O)c([C@@]2C=C(C)CC[C@]2C(C)=C)c(O)c1)[n]1c(*)nnc1* Chemical compound C*(CC(C)(C)c1cc(O)c([C@@]2C=C(C)CC[C@]2C(C)=C)c(O)c1)[n]1c(*)nnc1* 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET 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
- A61K31/4192—1,2,3-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET 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
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- A61P25/28—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
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
Abstract
Pharmaceutical compositions of the invention include novel functionalized 1,3-benzenediols having a disease-modifying action in the treatment of hepatic encephalopathy and related conditions. Pharmaceutical compositions of the invention further include novel neuroprotective agents.
Description
(57) Abstract: Pharmaceutical compositions of the invention include novel functionalized 1,3-benzenediols having a disease-modifying action in the treatment of hepatic encephalopathy and related conditions. Pharmaceutical compositions of the invention further include novel neuroprotective agents.
-H—IV-2 mg/kg —·—PO-10 mg/kg
20 24 wo 2015/106108 A3 lllllllllllllllllllllllllllllllll (88) Date of publication of the international search report:
November 2015
2015204609 24 Sep 2019
NOVEL FUNCTIONALIZED 1,3-BENZENE DIOLS AND THEIR METHOD OF USE FOR THE TREATMENT OF HEPATIC ENCEPHALOPATHY
CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Provisional Application No. 61926869 filed January 13th, 2014, which is herein incorporated by reference in its entirety.
FIELD OF INVENTION
Claims (18)
- Including hydrates, solvates, pharmaceutically acceptable salts, prodrugs, enantiomers, and complexes thereof, wherein:z is 0, 1, or 2;Y-N , R1 is selected from the group consisting ofWhen A is R1R , and RWhen A is R1and z is 0, R1 isWhen A is R1Y-NR3;and z is 1, R1 isand z is 2, R1 is selected from the group consisting ofWhen A is R1When R1 is, n is not 0;2015204609 24 Sep 2019 □4a Tn,X.NWhen R1 is R4b N , n is not 0;Y-N'R2 is R3;W is (CH2)m;m is 1 or 2;Y is (CH2)q;q is 1 or 2;n is 0, 1, 2, or 3;b is 0, 1, 2, or 3;d is 0, 1, 2, or 3;R3 is selected from the group consisting of COR5, CO2R6, CONR7aR7b, SO2NR7aR7b, SO2R8, and optionally substituted heteroaryl;R4a and R4b are each independently selected from the group consisting of hydrogen and Ci-6 alkyl;R4c is selected from the group consisting of hydrogen and OH;R5 is selected from the group consisting of hydrogen, Ci-6 alkyl, optional substituted heteroaryl, -C(R9aR9b)NR7aR7b, and -C(R9aR9b)OR10;R5 is also selected from optional substituted Ci-6 alkyl;R6 is Ci-6 alkyl;R6 is also selected from optional substituted Ci-6 alkyl;R7a and R7b are each independently selected from the group consisting of hydrogen and Ci-6 alkyl;R7a and R7b are also each independently selected from optional substituted Ci-6 alkyl;R8 is selected from the group consisting of hydrogen, Ci-6 alkyl and optional substituted heteroaryl;R8 is also selected from optional substituted Ci-6 alkyl;R9a and R9b are each independently selected from the group consisting of hydrogen, Ci-6 alkyl, C3-7 branched alkyl, CH2OH, CH(OH)CH3, CH2Ph, CH2(4OH-Ph), (CH2)4NH2, (CH2)3NHC(NH2)NH, CH2(3-indole), CH2(5-imidazole), CH2CO2H, CH2CH2CO2H, CH2CONH2, and CH2CH2CONH2;1002015204609 24 Sep 2019R10 is selected from the group consisting of hydrogen and Ci-6 alkyl.
- 10. The compound according to claim 1 having formula (X):102 including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof.
- 11. The compound according to claim 1 that is:5-(2-( 1 Η-1,2,3-triazol-1 -yl)ethyl)-2-(( 1 R,6R)-3-methyl-6-(prop-1 -en-2yl)cyclohex-2-enyl)benzene-1,3 -diol;2015204609 24 Sep 20191-(3-(3,5-dihydro xy-4-((lR, 6R)-3-methyl-6-(prop-l-en-2-yl)cyclohex-2enyl)benzyl)azetidin-1 -yl)ethanone;ethyl 3-(3,5-dihydro xy-4-((lR, 6R)-3-methyl-6-(prop-l-en-2-yl)cyclohex-2enyl)benzyl) azetidine-1 -carboxylate;or a pharmaceutically acceptable salt thereof.
- 12. A compound of the formula (I) according to claim 1 that is isotopically labeled with 1 to 10 deuterium atoms.
- 13. A composition comprising an effective amount of at least one compound according to any one of claims 1 to 12.
- 14. The composition according to claim 13, further comprising at least one excipient.
- 15. A neuroprotection method comprising administering to a subject at least one compound according to any one of claims 1-12 in an amount effective to protect neurons.
- 16. The neuroprotection method of claim 15, wherein the neurons are protected from oxidative stress.
- 17. The neuroprotection method of claim 15, wherein the neurons are protected from death or damage caused by oxidative stress or excess glutamate.
- 18. The neuroprotection method of claim 15, wherein the neurons are protected from death or damage caused by oxidative stress associated with a disease or condition selected from the group consisting of epilepsy, neuropathic pain, traumatic head injury, stroke, Chronic Traumatic Encephalopathy (CTE), Post Cardiac Arrest Hypoxic Ischemic Encephalopathy, Epileptic Encephalopathy, and neurodegenerative diseases such as Parkinson’s disease, Alzheimer’s, Huntington’s disease, and amyotrophic lateral sclerosis (ALS).103WO 2015/106108PCT/US2015/0108271/1Figure 1Mean plasma concentration-time profiles of KLS-13019 after single IV and PO administrations in CD1 mice (N=3/time point)Mean plasma concentration (ng/mL) Mean plasma cot (centration (ng/mL)10000 Ί1000 ¾ -b—IV-2 mg/kgJi1 0.1 -I........-.............: ..................,-----------------------------------;----------------s0 4 8 12 16 20 24Time (hr)Figure 2Mean plasma concentration-time profiles of KLS-13019 after single 10 mg.kg PO administrations in CD1 mice (N=3/time point)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201461926869P | 2014-01-13 | 2014-01-13 | |
US61/926,869 | 2014-01-13 | ||
PCT/US2015/010827 WO2015106108A2 (en) | 2014-01-13 | 2015-01-09 | Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy |
Publications (2)
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AU2015204609A1 AU2015204609A1 (en) | 2016-09-01 |
AU2015204609B2 true AU2015204609B2 (en) | 2019-11-07 |
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AU2015204609A Active AU2015204609B2 (en) | 2014-01-13 | 2015-01-09 | Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy |
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US (2) | US9611213B2 (en) |
EP (1) | EP3094318B1 (en) |
JP (1) | JP6486950B2 (en) |
CN (1) | CN106456573B (en) |
AU (1) | AU2015204609B2 (en) |
CA (1) | CA2936506C (en) |
DK (1) | DK3094318T3 (en) |
ES (1) | ES2791291T3 (en) |
RU (1) | RU2676475C2 (en) |
WO (1) | WO2015106108A2 (en) |
Families Citing this family (3)
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CN111943813A (en) * | 2019-05-17 | 2020-11-17 | 上海特化医药科技有限公司 | Preparation method of cannabidiol compound |
WO2021097351A1 (en) * | 2019-11-13 | 2021-05-20 | Kannalife Sciences, Inc. | Functionalized 1,3-benzene diols and their method of use for the treatment of radiation dermatitis and other skin disorders |
WO2022165332A2 (en) * | 2021-02-01 | 2022-08-04 | Neuropathix, Inc. | Functionalized 1,3-benzene diols and their method of use for the treatment of inflammation and pain |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100022631A1 (en) * | 2006-10-25 | 2010-01-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Treatment of hepatic encephalopathy and liver cirrhosis |
US20120172339A1 (en) * | 2009-07-10 | 2012-07-05 | Northeastern University | Angiogenic resorcinol derivatives |
EA016813B1 (en) * | 2005-06-16 | 2012-07-30 | Еуро-Селтик С.А. | Cannabinoid pharmaceutical composition and methods for preparing and administration thereof |
CN103113340A (en) * | 2013-01-21 | 2013-05-22 | 四川大学 | Genistein alkylamine compound, preparation method and use of genistein alkylamine compound |
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2015
- 2015-01-09 CN CN201580013646.6A patent/CN106456573B/en active Active
- 2015-01-09 ES ES15734870T patent/ES2791291T3/en active Active
- 2015-01-09 JP JP2016547058A patent/JP6486950B2/en active Active
- 2015-01-09 AU AU2015204609A patent/AU2015204609B2/en active Active
- 2015-01-09 WO PCT/US2015/010827 patent/WO2015106108A2/en active Application Filing
- 2015-01-09 DK DK15734870.7T patent/DK3094318T3/en active
- 2015-01-09 CA CA2936506A patent/CA2936506C/en active Active
- 2015-01-09 EP EP15734870.7A patent/EP3094318B1/en active Active
- 2015-01-09 US US14/781,081 patent/US9611213B2/en active Active
- 2015-01-09 RU RU2016133213A patent/RU2676475C2/en active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EA016813B1 (en) * | 2005-06-16 | 2012-07-30 | Еуро-Селтик С.А. | Cannabinoid pharmaceutical composition and methods for preparing and administration thereof |
US20100022631A1 (en) * | 2006-10-25 | 2010-01-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Treatment of hepatic encephalopathy and liver cirrhosis |
US20120172339A1 (en) * | 2009-07-10 | 2012-07-05 | Northeastern University | Angiogenic resorcinol derivatives |
CN103113340A (en) * | 2013-01-21 | 2013-05-22 | 四川大学 | Genistein alkylamine compound, preparation method and use of genistein alkylamine compound |
Also Published As
Publication number | Publication date |
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US20160311769A1 (en) | 2016-10-27 |
US20170157097A1 (en) | 2017-06-08 |
US9611213B2 (en) | 2017-04-04 |
RU2016133213A (en) | 2018-02-20 |
CA2936506C (en) | 2021-02-23 |
CN106456573A (en) | 2017-02-22 |
EP3094318A4 (en) | 2016-11-23 |
ES2791291T3 (en) | 2020-11-03 |
WO2015106108A3 (en) | 2015-11-12 |
CN106456573B (en) | 2019-12-03 |
RU2676475C2 (en) | 2018-12-29 |
RU2016133213A3 (en) | 2018-06-14 |
AU2015204609A1 (en) | 2016-09-01 |
EP3094318B1 (en) | 2020-02-19 |
US10004722B2 (en) | 2018-06-26 |
EP3094318A2 (en) | 2016-11-23 |
CA2936506A1 (en) | 2015-07-16 |
DK3094318T3 (en) | 2020-05-04 |
JP2017507119A (en) | 2017-03-16 |
WO2015106108A2 (en) | 2015-07-16 |
JP6486950B2 (en) | 2019-03-20 |
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