RU2560144C2 - Выделяющие оксид азота соединения - Google Patents
Выделяющие оксид азота соединения Download PDFInfo
- Publication number
- RU2560144C2 RU2560144C2 RU2011118522/04A RU2011118522A RU2560144C2 RU 2560144 C2 RU2560144 C2 RU 2560144C2 RU 2011118522/04 A RU2011118522/04 A RU 2011118522/04A RU 2011118522 A RU2011118522 A RU 2011118522A RU 2560144 C2 RU2560144 C2 RU 2560144C2
- Authority
- RU
- Russia
- Prior art keywords
- dystrophy
- formula
- nitric oxide
- muscle
- treatment
- Prior art date
Links
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title abstract description 40
- 150000001875 compounds Chemical class 0.000 title abstract description 20
- 201000006938 muscular dystrophy Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims description 15
- 239000002840 nitric oxide donor Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 10
- 238000011161 development Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract 1
- -1 nitroxy Chemical class 0.000 description 16
- 229940079593 drug Drugs 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 7
- 229960001145 deflazacort Drugs 0.000 description 7
- FBHSPRKOSMHSIF-GRMWVWQJSA-N deflazacort Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)=N[C@@]3(C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O FBHSPRKOSMHSIF-GRMWVWQJSA-N 0.000 description 7
- 229960004618 prednisone Drugs 0.000 description 7
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 6
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 6
- 210000002027 skeletal muscle Anatomy 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 102000004420 Creatine Kinase Human genes 0.000 description 5
- 108010042126 Creatine kinase Proteins 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 5
- 239000003246 corticosteroid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 210000001087 myotubule Anatomy 0.000 description 5
- 229960002965 pravastatin Drugs 0.000 description 5
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 4
- 230000001338 necrotic effect Effects 0.000 description 4
- 102000016579 Alpha-sarcoglycan Human genes 0.000 description 3
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
- 208000029578 Muscle disease Diseases 0.000 description 3
- 208000021642 Muscular disease Diseases 0.000 description 3
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 3
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 3
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 3
- 108010083379 Sarcoglycans Proteins 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229960001334 corticosteroids Drugs 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102100022745 Laminin subunit alpha-2 Human genes 0.000 description 2
- 208000029549 Muscle injury Diseases 0.000 description 2
- 201000009623 Myopathy Diseases 0.000 description 2
- 206010068871 Myotonic dystrophy Diseases 0.000 description 2
- 208000021017 Weight Gain Diseases 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 229960005370 atorvastatin Drugs 0.000 description 2
- 229910000062 azane Inorganic materials 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 201000006815 congenital muscular dystrophy Diseases 0.000 description 2
- 208000011425 congenital myotonic dystrophy Diseases 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 201000009340 myotonic dystrophy type 1 Diseases 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 230000037081 physical activity Effects 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 0 C*C(Cc1cccc(C(c(cc2)ccc2Br)=O)c1N)=O Chemical compound C*C(Cc1cccc(C(c(cc2)ccc2Br)=O)c1N)=O 0.000 description 1
- LECFRILCOIULEU-UHFFFAOYSA-N CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c2ccc(C=C)cc2)[n]1CCC(CC(CC(C)=O)O)O Chemical compound CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c2ccc(C=C)cc2)[n]1CCC(CC(CC(C)=O)O)O LECFRILCOIULEU-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- 102000001039 Dystrophin Human genes 0.000 description 1
- 108010069091 Dystrophin Proteins 0.000 description 1
- 206010048554 Endothelial dysfunction Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 208000026214 Skeletal muscle atrophy Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 230000006502 antiplatelets effects Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000008694 endothelial dysfunction Effects 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012595 freezing medium Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 230000005931 immune cell recruitment Effects 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 208000026526 progressive weakness Diseases 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000000518 sarcolemma Anatomy 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000025185 skeletal muscle atrophy Effects 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
- A61K31/04—Nitro compounds
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
- A61K31/38—Heterocyclic compounds 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/42—Oxazoles
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
-
- 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
-
- 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
-
- 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
-
- 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
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76475506P | 2006-02-03 | 2006-02-03 | |
| US60/764.755 | 2006-02-03 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008135153/15A Division RU2429828C2 (ru) | 2006-02-03 | 2007-01-23 | Применение нитрооксипроизводного лекарственного средства для лечения мышечной дистрофии |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011118522A RU2011118522A (ru) | 2012-11-20 |
| RU2560144C2 true RU2560144C2 (ru) | 2015-08-20 |
Family
ID=38004694
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011118522/04A RU2560144C2 (ru) | 2006-02-03 | 2007-01-23 | Выделяющие оксид азота соединения |
| RU2008135153/15A RU2429828C2 (ru) | 2006-02-03 | 2007-01-23 | Применение нитрооксипроизводного лекарственного средства для лечения мышечной дистрофии |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008135153/15A RU2429828C2 (ru) | 2006-02-03 | 2007-01-23 | Применение нитрооксипроизводного лекарственного средства для лечения мышечной дистрофии |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8575222B2 (enExample) |
| EP (2) | EP1978947B1 (enExample) |
| JP (1) | JP5745210B2 (enExample) |
| KR (1) | KR20080097989A (enExample) |
| CN (1) | CN101378739B (enExample) |
| AU (1) | AU2007211508B2 (enExample) |
| CA (1) | CA2641816C (enExample) |
| DK (1) | DK1978947T3 (enExample) |
| ES (1) | ES2520893T3 (enExample) |
| IL (1) | IL192299A0 (enExample) |
| NZ (1) | NZ569396A (enExample) |
| PL (1) | PL1978947T3 (enExample) |
| PT (1) | PT1978947E (enExample) |
| RU (2) | RU2560144C2 (enExample) |
| SI (1) | SI1978947T1 (enExample) |
| WO (1) | WO2007088123A2 (enExample) |
| ZA (1) | ZA200805716B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1888510A4 (en) | 2005-05-27 | 2013-01-16 | Univ North Carolina | NITROGEN OXIDE-RELATED PARTICLES FOR NITROGEN OXIDE THERAPEUTICS AND BIOMEDICAL APPLICATIONS |
| CA2659909A1 (en) | 2006-08-01 | 2008-02-07 | Phrixus Pharmaceuticals, Inc. | Treatment for chronic progressive heart failure |
| JP2010523612A (ja) * | 2007-04-13 | 2010-07-15 | ニコックス エス エイ | アトルバスタチン４−（ニトロオキシ）ブチルエステルの結晶形態 |
| ES2594302T3 (es) | 2007-12-17 | 2016-12-19 | The Regents Of The University Of Michigan | Composiciones y procedimientos de tratamiento y prevención de deficiencias de músculo esquelético |
| JP2011516442A (ja) * | 2008-04-04 | 2011-05-26 | ビオマリン アイジーエー リミテッド | 筋ジストロフィーを治療するための化合物 |
| WO2010108843A1 (en) | 2009-03-27 | 2010-09-30 | Nicox S.A. | Use of nitrooxyderivative of paracetamol for the treatment of muscular dystrophies |
| CA3062005C (en) | 2009-08-21 | 2022-02-15 | Novan, Inc. | Topical gels comprising nitric oxide-releasing polysiloxane macromolecules and uses thereof |
| BR112012003804B1 (pt) | 2009-08-21 | 2019-02-19 | Novan, Inc. | Curativo para ferimentos, método para formar um curativo para ferimentos, e, kit de curativo para ferimento |
| US9023890B2 (en) | 2009-12-02 | 2015-05-05 | The Charlotte-Mecklenburg Hospital Authority | Nitrate esters and their use for the treatment of muscle and muscle related diseases |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| EP2681286B1 (en) | 2011-02-28 | 2018-08-15 | Novan, Inc. | Nitric oxide-releasing s-nitrosothiol-modified silica particles and methods of making the same |
| US9452117B2 (en) | 2011-06-01 | 2016-09-27 | The Charlotte-Mecklenburg Hospital Authority | Nitrate esters and their use for the treatment of muscle and muscle related diseases |
| US9844599B2 (en) | 2013-01-21 | 2017-12-19 | Apparao Satyam | Nitric oxide releasing produgs of therapeutic agents |
| RU2517259C1 (ru) * | 2013-03-06 | 2014-05-27 | Федеральное государственное бюджетное учреждение науки Государственный научный центр Российской Федерации - Институт медико-биологических проблем Российской академии наук (ГНЦ РФ-ИМБП РАН) | Способ профилактики и снижения деструкции белков скелетных мышц при их атрофии, вызванной гипокинезией и/или гравитационной разгрузкой |
| WO2014169976A1 (en) * | 2013-04-18 | 2014-10-23 | Nicox Science Ireland | Quinone based nitric oxide donating compounds |
| US9974767B2 (en) | 2014-07-14 | 2018-05-22 | University Of Washington | Statins in the treatment of muscular dystrophies and myopathies |
| US10993993B2 (en) | 2015-05-28 | 2021-05-04 | Immunoforge Co., Ltd. | Pharmaceutical composition for treating muscle atrophy or sarcopenia including glucagon-like peptide (GLP-1) or GLP-1 receptor agonist |
| KR101661332B1 (ko) | 2015-05-28 | 2016-09-29 | (의료)길의료재단 | 글루카곤 유사 펩타이드-1 수용체 항진제를 포함하는 근감소증 치료용 약학 조성물 |
| TN2019000290A1 (en) | 2017-03-20 | 2021-05-07 | Forma Therapeutics Inc | Pyrrolopyrrole compositions as pyruvate kinase (pkr) activators |
| ES3015109T3 (en) | 2018-04-25 | 2025-04-29 | Oncocross Co Ltd | Dimenhydrinate and calcium pantothenate for preventing and treating muscular disease |
| WO2020055186A1 (ko) | 2018-09-14 | 2020-03-19 | 고려대학교 산학협력단 | If1 을 유효성분으로 함유하는 비만 또는 근감소증의 예방 또는 치료용 약학 조성물 |
| JP7450610B2 (ja) | 2018-09-19 | 2024-03-15 | ノヴォ・ノルディスク・ヘルス・ケア・アーゲー | ピルビン酸キナーゼｒの活性化 |
| BR112021005188A2 (pt) | 2018-09-19 | 2021-06-08 | Forma Therapeutics, Inc. | tratamento de anemia falciforme com um composto de ativação de piruvato cinase r |
| BR112022004715A2 (pt) | 2019-09-19 | 2022-06-14 | Forma Therapeutics Inc | Composições de ativação de piruvato quinase r (pkr) |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| KR102272616B1 (ko) | 2021-03-25 | 2021-07-05 | 주식회사 엔테로바이옴 | 피컬리박테리움 프로스니치 균주를 포함하는 근위축증 예방 또는 치료용 약학적 조성물 |
| KR102329853B1 (ko) | 2021-03-25 | 2021-11-23 | 주식회사 엔테로바이옴 | 아커만시아 뮤시니필라 균주를 포함하는 근위축증 예방 또는 치료용 약학적 조성물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003013499A2 (en) * | 2001-08-09 | 2003-02-20 | Nicox S.A. | Drugs for vasculopaties |
| WO2004000273A1 (en) * | 2002-06-25 | 2003-12-31 | Nicox S.A. | Oral pharmaceutical forms of liquid drugs having improved bioavailability |
| RU2248348C2 (ru) * | 1999-08-04 | 2005-03-20 | Никокс С.А. | Способ получения нитроксиалкиловых эфиров напроксена |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU702662B2 (en) * | 1994-05-10 | 1999-02-25 | Nicox S.A. | Nitro compounds and their compositions having anti-inflammatory, analgesic and anti-thrombotic acitivities |
| US5583101A (en) * | 1994-07-15 | 1996-12-10 | Harvard College | Use of nitrogen oxide species and adducts to inhibit skeletal muscle contraction |
| IT1288123B1 (it) * | 1996-09-04 | 1998-09-10 | Nicox Sa | Uso di nitroderivati per l'incontinenza urinaria |
| CA2371927A1 (en) * | 1999-03-11 | 2000-09-14 | The University Of Manitoba | Nitric oxide manipulation of muscle satellite cell activation |
| FR2794647A1 (fr) * | 1999-06-11 | 2000-12-15 | Centre Nat Rech Scient | Compositions pharmaceutique comprenant du no ou au moins un compose capable de liberer ou d'induire la formation de no dans les cellules |
| ITMI991517A1 (it) | 1999-07-09 | 2001-01-09 | Nicox Sa | Procedimento per ottenere nitrossimetil fenil esterni di derivati dell'acido salicilico |
| US7166638B2 (en) * | 2003-05-27 | 2007-01-23 | Nicox S.A. | Statin derivatives |
| WO2005023189A2 (en) * | 2003-09-03 | 2005-03-17 | Pharmacia Corporation | Method of cox-2 selective inhibitor and nitric oxide-donating agent |
| GB0321228D0 (en) * | 2003-09-10 | 2003-10-08 | Inpharmatica Ltd | Modulating cell activity |
| CA2820200C (en) * | 2005-06-09 | 2015-08-18 | Judith Esther Anderson | Compositions and methods for enhancing nitric oxide delivery |
| US8247460B2 (en) | 2006-02-03 | 2012-08-21 | Giulio Cossu | Method of treatment for muscular dystrophy |
-
2007
- 2007-01-23 RU RU2011118522/04A patent/RU2560144C2/ru not_active IP Right Cessation
- 2007-01-23 PL PL07712084T patent/PL1978947T3/pl unknown
- 2007-01-23 RU RU2008135153/15A patent/RU2429828C2/ru not_active IP Right Cessation
- 2007-01-23 CN CN200780004219.7A patent/CN101378739B/zh not_active Expired - Fee Related
- 2007-01-23 WO PCT/EP2007/050630 patent/WO2007088123A2/en not_active Ceased
- 2007-01-23 CA CA2641816A patent/CA2641816C/en not_active Expired - Fee Related
- 2007-01-23 EP EP07712084.8A patent/EP1978947B1/en active Active
- 2007-01-23 NZ NZ569396A patent/NZ569396A/en not_active IP Right Cessation
- 2007-01-23 DK DK07712084.8T patent/DK1978947T3/da active
- 2007-01-23 PT PT77120848T patent/PT1978947E/pt unknown
- 2007-01-23 SI SI200731542T patent/SI1978947T1/sl unknown
- 2007-01-23 JP JP2008552778A patent/JP5745210B2/ja not_active Expired - Fee Related
- 2007-01-23 EP EP20140175223 patent/EP2786749A1/en not_active Withdrawn
- 2007-01-23 AU AU2007211508A patent/AU2007211508B2/en not_active Ceased
- 2007-01-23 US US12/159,577 patent/US8575222B2/en not_active Expired - Fee Related
- 2007-01-23 KR KR1020087015930A patent/KR20080097989A/ko not_active Ceased
- 2007-01-23 ES ES07712084.8T patent/ES2520893T3/es active Active
-
2008
- 2008-06-19 IL IL192299A patent/IL192299A0/en unknown
- 2008-06-30 ZA ZA200805716A patent/ZA200805716B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2248348C2 (ru) * | 1999-08-04 | 2005-03-20 | Никокс С.А. | Способ получения нитроксиалкиловых эфиров напроксена |
| WO2003013499A2 (en) * | 2001-08-09 | 2003-02-20 | Nicox S.A. | Drugs for vasculopaties |
| WO2004000273A1 (en) * | 2002-06-25 | 2003-12-31 | Nicox S.A. | Oral pharmaceutical forms of liquid drugs having improved bioavailability |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2011118522A (ru) | 2012-11-20 |
| ZA200805716B (en) | 2009-11-25 |
| AU2007211508B2 (en) | 2012-08-23 |
| WO2007088123A2 (en) | 2007-08-09 |
| PT1978947E (pt) | 2014-11-03 |
| CN101378739A (zh) | 2009-03-04 |
| JP2009525302A (ja) | 2009-07-09 |
| CA2641816C (en) | 2016-01-05 |
| KR20080097989A (ko) | 2008-11-06 |
| ES2520893T3 (es) | 2014-11-12 |
| WO2007088123A3 (en) | 2007-09-20 |
| CN101378739B (zh) | 2014-06-04 |
| RU2429828C2 (ru) | 2011-09-27 |
| CA2641816A1 (en) | 2007-08-09 |
| DK1978947T3 (da) | 2014-11-03 |
| IL192299A0 (en) | 2009-08-03 |
| EP2786749A1 (en) | 2014-10-08 |
| PL1978947T3 (pl) | 2015-03-31 |
| AU2007211508A1 (en) | 2007-08-09 |
| SI1978947T1 (sl) | 2014-12-31 |
| JP5745210B2 (ja) | 2015-07-08 |
| HK1129592A1 (en) | 2009-12-04 |
| US20090093510A1 (en) | 2009-04-09 |
| NZ569396A (en) | 2011-06-30 |
| US8575222B2 (en) | 2013-11-05 |
| EP1978947B1 (en) | 2014-08-13 |
| RU2008135153A (ru) | 2010-03-10 |
| EP1978947A2 (en) | 2008-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2560144C2 (ru) | Выделяющие оксид азота соединения | |
| JP6422163B2 (ja) | ウロリチンまたはその前駆体の投与によるオートファジーの増強または寿命の延長 | |
| FR2753098A1 (fr) | Composition pharmaceutique comprenant au moins un inhibiteur de no synthase et au moins un piegeur des formes reactives de l'oxygene | |
| US20130157986A1 (en) | Novel methylenedioxy phenolic compounds and their use to treat disease | |
| EP2120919B1 (en) | New combination for use in the treatment of inflammatory disorders | |
| JP2005526768A (ja) | 炎症関連遺伝子を調節するデキサナビノール及びデキサナビノール類似体 | |
| WO2010127313A1 (en) | Hmg-coa secondary metabolites and uses thereof | |
| EP2107907B1 (en) | Combination of pemirolast and ramatroban for use in the treatment of inflammatory disorders | |
| AU2009235276A1 (en) | New combination for use in the treatment of inflammatory disorders | |
| US8802726B2 (en) | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies | |
| HK1129592B (en) | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies | |
| WO2009122182A1 (en) | New combination for use in the treatment of inflammatory disorders | |
| HK1134032B (en) | New combination for use in the treatment of inflammatory disorders | |
| WO2009122183A1 (en) | New combination for use in the treatment of inflammatory disorders | |
| JP2007509054A (ja) | 血管健康を促進するシリルフェノール |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HZ9A | Changing address for correspondence with an applicant | ||
| PC41 | Official registration of the transfer of exclusive right |
Effective date: 20181229 |
|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20200124 |