BE823841A - Derives de 5-(1-hydroxy-2-amino substitue) alkyl-8-carbostyryle substitue et de 5-(1-hydroxy-2-amino substitue) alkyl-8-(3,4-dihydro) carbostyryle substitue et leur procede de preparation - Google Patents
Derives de 5-(1-hydroxy-2-amino substitue) alkyl-8-carbostyryle substitue et de 5-(1-hydroxy-2-amino substitue) alkyl-8-(3,4-dihydro) carbostyryle substitue et leur procede de preparationInfo
- Publication number
- BE823841A BE823841A BE151913A BE151913A BE823841A BE 823841 A BE823841 A BE 823841A BE 151913 A BE151913 A BE 151913A BE 151913 A BE151913 A BE 151913A BE 823841 A BE823841 A BE 823841A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- hydroxy
- dihydrocarbostyryl
- mixture
- temperature
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 3,4dihydrocarbostyril compound Chemical class 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 32
- 230000009467 reduction Effects 0.000 claims description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 238000010992 reflux Methods 0.000 claims description 20
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical group ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
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- 230000008569 process Effects 0.000 claims description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- ZXZKYYHTWHJHFT-UHFFFAOYSA-N quinoline-2,8-diol Chemical group C1=CC(=O)NC2=C1C=CC=C2O ZXZKYYHTWHJHFT-UHFFFAOYSA-N 0.000 description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 9
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- 238000001914 filtration Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
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- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004044 bronchoconstricting agent Substances 0.000 description 1
- 230000003435 bronchoconstrictive effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP744192A JPS539227B2 (is") | 1973-12-26 | 1973-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE823841A true BE823841A (fr) | 1975-04-16 |
Family
ID=11577822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE151913A BE823841A (fr) | 1973-12-26 | 1974-12-24 | Derives de 5-(1-hydroxy-2-amino substitue) alkyl-8-carbostyryle substitue et de 5-(1-hydroxy-2-amino substitue) alkyl-8-(3,4-dihydro) carbostyryle substitue et leur procede de preparation |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS539227B2 (is") |
| BE (1) | BE823841A (is") |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4223137A (en) * | 1976-10-08 | 1980-09-16 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and process for preparing the same |
| US4314944A (en) | 1980-08-22 | 1982-02-09 | Smithkline Corporation | 4-Aminoalkyl-7-hydroxy-2(3H)-indolones |
| US5053514A (en) * | 1988-08-10 | 1991-10-01 | Otsuka Pharmaceutical Company, Limited | Cardiotonics |
| WO2013115793A1 (en) * | 2012-01-31 | 2013-08-08 | Varinel, Inc. | Iron chelators and uses thereof |
| US10288602B2 (en) | 2013-01-08 | 2019-05-14 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatement |
| US11357757B2 (en) | 2017-09-13 | 2022-06-14 | Atrogi Ab | Heteroaryl substituted beta-hydroxyethylamines for use in treating hyperglycaemia |
| US11427539B2 (en) | 2017-09-13 | 2022-08-30 | Atrogi Ab | Beta-hydroxy heterocyclic amines and their use in the treatment of hyperglycaemia |
| US11648216B2 (en) | 2017-09-13 | 2023-05-16 | Atrogi Ab | Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia |
| US11793774B2 (en) | 2017-09-13 | 2023-10-24 | Atrogi Ab | Chiral beta-hydroxyethylamines and their use in the treatment of hyperglycemia |
| WO2023203223A1 (en) | 2022-04-22 | 2023-10-26 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and beta 3-adrenergic receptor agonists, and medical uses thereof |
| WO2024153813A1 (en) | 2023-01-20 | 2024-07-25 | Atrogi Ab | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
| WO2024170727A1 (en) | 2023-02-16 | 2024-08-22 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and metformin for use in treating obesity and reducing body fat |
| WO2024184408A1 (en) | 2023-03-06 | 2024-09-12 | Atrogi Ab | Combination of beta-2-adrenergic receptor agonists and glp-1 receptor agonists for use in treating hyperglycaemia |
| US12378216B2 (en) | 2019-03-20 | 2025-08-05 | Atrogi Ab | Heteroaryl(heterocyclyl)methanol compounds useful in the treatment of hyperglycaemia |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS539232B2 (is") * | 1974-02-27 | 1978-04-04 | ||
| JPS5283380A (en) * | 1975-12-26 | 1977-07-12 | Otsuka Pharmaceut Co Ltd | Synthesis of thiocarbostyril derivatives |
-
1973
- 1973-12-26 JP JP744192A patent/JPS539227B2/ja not_active Expired
-
1974
- 1974-12-24 BE BE151913A patent/BE823841A/fr active Protection Beyond IP Right Term
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4223137A (en) * | 1976-10-08 | 1980-09-16 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and process for preparing the same |
| US4314944A (en) | 1980-08-22 | 1982-02-09 | Smithkline Corporation | 4-Aminoalkyl-7-hydroxy-2(3H)-indolones |
| US5053514A (en) * | 1988-08-10 | 1991-10-01 | Otsuka Pharmaceutical Company, Limited | Cardiotonics |
| WO2013115793A1 (en) * | 2012-01-31 | 2013-08-08 | Varinel, Inc. | Iron chelators and uses thereof |
| US10288602B2 (en) | 2013-01-08 | 2019-05-14 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatement |
| US11793774B2 (en) | 2017-09-13 | 2023-10-24 | Atrogi Ab | Chiral beta-hydroxyethylamines and their use in the treatment of hyperglycemia |
| US11427539B2 (en) | 2017-09-13 | 2022-08-30 | Atrogi Ab | Beta-hydroxy heterocyclic amines and their use in the treatment of hyperglycaemia |
| US11648216B2 (en) | 2017-09-13 | 2023-05-16 | Atrogi Ab | Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia |
| US11357757B2 (en) | 2017-09-13 | 2022-06-14 | Atrogi Ab | Heteroaryl substituted beta-hydroxyethylamines for use in treating hyperglycaemia |
| US12036210B2 (en) | 2017-09-13 | 2024-07-16 | Atrogi Ab | Heteroaryl substituted beta-hydroxyethylamines for use in treating hyperglycaemia |
| US12280023B2 (en) | 2017-09-13 | 2025-04-22 | Atrogi Ab | Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia |
| US12378216B2 (en) | 2019-03-20 | 2025-08-05 | Atrogi Ab | Heteroaryl(heterocyclyl)methanol compounds useful in the treatment of hyperglycaemia |
| WO2023203223A1 (en) | 2022-04-22 | 2023-10-26 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and beta 3-adrenergic receptor agonists, and medical uses thereof |
| WO2024153813A1 (en) | 2023-01-20 | 2024-07-25 | Atrogi Ab | Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting |
| WO2024170727A1 (en) | 2023-02-16 | 2024-08-22 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and metformin for use in treating obesity and reducing body fat |
| WO2024184408A1 (en) | 2023-03-06 | 2024-09-12 | Atrogi Ab | Combination of beta-2-adrenergic receptor agonists and glp-1 receptor agonists for use in treating hyperglycaemia |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5095279A (is") | 1975-07-29 |
| JPS539227B2 (is") | 1978-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CCPA | Application for a supplementary protection certificate |
Free format text: 093C0145 |
|
| RE20 | Patent expired |
Owner name: OTSUKA PHARMACEUTICAL CO. LTD Effective date: 19941224 |
|
| CCPV | Grant of a supplementary protection certificate |
Free format text: 093C0145, EXPIRES 19980314 |