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 PDF

Info

Publication number
AU2015204609B2
AU2015204609B2 AU2015204609A AU2015204609A AU2015204609B2 AU 2015204609 B2 AU2015204609 B2 AU 2015204609B2 AU 2015204609 A AU2015204609 A AU 2015204609A AU 2015204609 A AU2015204609 A AU 2015204609A AU 2015204609 B2 AU2015204609 B2 AU 2015204609B2
Authority
AU
Australia
Prior art keywords
alkyl
compound according
pharmaceutically acceptable
group
solvates
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
AU2015204609A
Other versions
AU2015204609A1 (en
Inventor
Douglas E. Brenneman
William Alvin Kinney
Mark Mcdonnell
Dean PETKANAS
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.)
Kannalife Sciences Inc
Original Assignee
Kannalife Sciences Inc
Kannalife Sciences Inc
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 US201461926869P priority Critical
Priority to US61/926,869 priority
Application filed by Kannalife Sciences Inc, Kannalife Sciences Inc filed Critical Kannalife Sciences Inc
Priority to PCT/US2015/010827 priority patent/WO2015106108A2/en
Publication of AU2015204609A1 publication Critical patent/AU2015204609A1/en
Application granted granted Critical
Publication of AU2015204609B2 publication Critical patent/AU2015204609B2/en
Assigned to Kannalife Science, Inc. reassignment Kannalife Science, Inc. Amend patent request/document other than specification (104) Assignors: KANNALIFE, INC.
Assigned to KANNALIFE SCIENCES, INC. reassignment KANNALIFE SCIENCES, INC. Amend patent request/document other than specification (104) Assignors: Kannalife Science, Inc.
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 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
Figure AU2015204609B2_D0001
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)

  1. Figure AU2015204609B2_C0001
    Including hydrates, solvates, pharmaceutically acceptable salts, prodrugs, enantiomers, and complexes thereof, wherein:
    Figure AU2015204609B2_C0002
    z is 0, 1, or 2;
    Figure AU2015204609B2_C0003
    Figure AU2015204609B2_C0004
    Y-N , R1 is selected from the group consisting of
    When A is R1
    Figure AU2015204609B2_C0005
    Figure AU2015204609B2_C0006
    R , and R
    Figure AU2015204609B2_C0007
    When A is R1
    Figure AU2015204609B2_C0008
    and z is 0, R1 is
    Figure AU2015204609B2_C0009
    When A is R1
    Figure AU2015204609B2_C0010
    Figure AU2015204609B2_C0011
    Y-N
    R3;
    and z is 1, R1 is
    Figure AU2015204609B2_C0012
    and z is 2, R1 is selected from the group consisting of
    When A is R1
    Figure AU2015204609B2_C0013
    When R1 is
    Figure AU2015204609B2_C0014
    , n is not 0;
    2015204609 24 Sep 2019 □4a Tn,
    X.N
    When 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;
    100
    2015204609 24 Sep 2019
    R10 is selected from the group consisting of hydrogen and Ci-6 alkyl.
  2. 2. The compound according to claim 1 having formula (II):
    Figure AU2015204609B2_C0015
    including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof
  3. 3. The compound according to claim 1 having formula (III):
    R4c
    Figure AU2015204609B2_C0016
    including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof
  4. 4. The compound according to claim 1 having formula (IV):
    Figure AU2015204609B2_C0017
    including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof
  5. 5. The compound according to claim 1 having formula (V):
    Figure AU2015204609B2_C0018
    including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof
  6. 6. The compound according to claim 1 having formula (VI):
    101 including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and
    2015204609 24 Sep 2019 complexes thereof.
    Figure AU2015204609B2_C0019
  7. 7. The compound according to claim 1 having formula (VII):
    Figure AU2015204609B2_C0020
    (VII) including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof.
  8. 8. The compound according to claim 1 having formula (VIII):
    Figure AU2015204609B2_C0021
    OH (VIII) ' including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof.
  9. 9. The compound according to claim 1 having formula (IX):
    Figure AU2015204609B2_C0022
    including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof.
  10. 10. The compound according to claim 1 having formula (X):
    102 including hydrates, solvates, pharmaceutically acceptable salts, enantiomers, and complexes thereof.
  11. 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 2019
    Figure AU2015204609B2_C0023
    1-(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. 12. A compound of the formula (I) according to claim 1 that is isotopically labeled with 1 to 10 deuterium atoms.
  13. 13. A composition comprising an effective amount of at least one compound according to any one of claims 1 to 12.
  14. 14. The composition according to claim 13, further comprising at least one excipient.
  15. 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. 16. The neuroprotection method of claim 15, wherein the neurons are protected from oxidative stress.
  17. 17. The neuroprotection method of claim 15, wherein the neurons are protected from death or damage caused by oxidative stress or excess glutamate.
  18. 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).
    103
    WO 2015/106108
    PCT/US2015/010827
    1/1
    Figure 1
    Mean 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 Ί
    1000 ¾ -b—IV-2 mg/kg
    Ji
    Figure AU2015204609B2_C0024
    1 0.1 -I........-.............: ..................,-----------------------------------;----------------s
    0 4 8 12 16 20 24
    Time (hr)
    Figure 2
    Mean plasma concentration-time profiles of KLS-13019 after single 10 mg.kg PO administrations in CD1 mice (N=3/time point)
    Figure AU2015204609B2_C0025
AU2015204609A 2014-01-13 2015-01-09 Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy Active AU2015204609B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US201461926869P true 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)

Publication Number Publication Date
AU2015204609A1 AU2015204609A1 (en) 2016-09-01
AU2015204609B2 true AU2015204609B2 (en) 2019-11-07

Family

ID=53524475

Family Applications (1)

Application Number Title Priority Date Filing Date
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

Country Status (10)

Country Link
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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (4)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
DK3094318T3 (en) 2020-05-04
WO2015106108A2 (en) 2015-07-16
CN106456573A (en) 2017-02-22
US9611213B2 (en) 2017-04-04
JP2017507119A (en) 2017-03-16
CA2936506C (en) 2021-02-23
EP3094318A2 (en) 2016-11-23
CN106456573B (en) 2019-12-03
CA2936506A1 (en) 2015-07-16
JP6486950B2 (en) 2019-03-20
EP3094318B1 (en) 2020-02-19
EP3094318A4 (en) 2016-11-23
AU2015204609A1 (en) 2016-09-01
US10004722B2 (en) 2018-06-26
ES2791291T3 (en) 2020-11-03
RU2676475C2 (en) 2018-12-29
US20170157097A1 (en) 2017-06-08
WO2015106108A3 (en) 2015-11-12
US20160311769A1 (en) 2016-10-27
RU2016133213A3 (en) 2018-06-14
RU2016133213A (en) 2018-02-20

Similar Documents

Publication Publication Date Title
IL227496D0 (en) Derivatives of azaindazole or diazaindazole type as medicament
WO2017123884A8 (en) Heterocyclic compounds as rsv inhibitors
MA37405A1 (en) Heterocyclyl compounds
JP2014511892A5 (en)
NZ627750A (en) Carbamate compounds and of making and using same
WO2011126910A3 (en) Compositions and methods for the treatment of somatosensory disorders
JP2009541223A5 (en)
US20180344713A1 (en) Methods for treatment of fibrotic diseases
MX2009010759A (en) Imidazolidine carboxamide derivatives as p2x7 modulators.
NZ721645A (en) Compounds for use as gpr120 agonists
JP2016513696A5 (en)
WO2008125600A3 (en) Pyrazole derivatives as p2x7 modulators
MX2011008910A (en) Substituted azole derivatives, pharmaceutical composition containing the derivatives, and method for treating parkinson's disease using the same.
MX2013011290A (en) Pyrrole derivatives as nicotinic acetylcholine receptor modulators for use in the treatment of neurodegenerative disorders such as alzheimer's and parkinson's disease.
WO2008119685A3 (en) Oxazolidine and morpholine carboxamide derivatives as p2x7 modulators
MX2019000451A (en) Heterocyclic compound used as fgfr inhibitor.
JP2015502371A5 (en)
AU2015204609B2 (en) Novel functionalized 1,3-benzene diols and their method of use for the treatment of hepatic encephalopathy
MX2019012827A (en) Novel tetrahydronaphthyl urea derivatives.
MX2019010096A (en) 1, 4, 6-trisubstituted-2-alkyl-1h-benzo[d]imidazole derivatives as dihydroorotate oxygenase inhibitors.
PH12019550083A1 (en) Inhibitors of bruton's tyrosine kinase
MX2019008626A (en) 1,1,1-trifluoro-3-hydroxypropan-2-yl carbamate derivatives as magl inhibitors.
BR112012023178A2 (en) substituted ramidines as prostaglandin 2 receptor antagonists
CA3148613A1 (en) Compounds for inhibition of alpha 4 beta 7 integrin
SG190067A1 (en) Trans-2-decenoic acid derivative and pharmaceutical agent containing the same

Legal Events

Date Code Title Description
HB Alteration of name in register

Owner name: KANNALIFE SCIENCE, INC.

Free format text: FORMER NAME(S): KANNALIFE, INC.

HB Alteration of name in register

Owner name: KANNALIFE SCIENCES, INC.

Free format text: FORMER NAME(S): KANNALIFE SCIENCE, INC.

FGA Letters patent sealed or granted (standard patent)