MA39947B1 - Dérivés aminoestérifiés - Google Patents
Dérivés aminoestérifiésInfo
- Publication number
- MA39947B1 MA39947B1 MA39947A MA39947A MA39947B1 MA 39947 B1 MA39947 B1 MA 39947B1 MA 39947 A MA39947 A MA 39947A MA 39947 A MA39947 A MA 39947A MA 39947 B1 MA39947 B1 MA 39947B1
- Authority
- MA
- Morocco
- Prior art keywords
- buffer
- edta
- hcl
- tris
- binding
- Prior art date
Links
- 239000000872 buffer Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 abstract 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract 3
- 230000027455 binding Effects 0.000 abstract 3
- 238000003556 assay Methods 0.000 abstract 2
- 238000005119 centrifugation Methods 0.000 abstract 2
- 238000002474 experimental method Methods 0.000 abstract 2
- 239000012528 membrane Substances 0.000 abstract 2
- 239000008188 pellet Substances 0.000 abstract 2
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 abstract 1
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 abstract 1
- LZCOQTDXKCNBEE-XJMZPCNVSA-N N-methylscopolamine Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-XJMZPCNVSA-N 0.000 abstract 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract 1
- 210000001728 clone cell Anatomy 0.000 abstract 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- LZCOQTDXKCNBEE-IKIFYQGPSA-N methscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-IKIFYQGPSA-N 0.000 abstract 1
- 229960001383 methylscopolamine Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003681 muscarinic M3 receptor antagonist Substances 0.000 abstract 1
- 230000003551 muscarinic effect Effects 0.000 abstract 1
- 230000009871 nonspecific binding Effects 0.000 abstract 1
- 239000002953 phosphate buffered saline Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000002285 radioactive effect Effects 0.000 abstract 1
- 239000002287 radioligand Substances 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring 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
- A61K31/395—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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
-
- 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
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
L'invention concerne de nouveaux composés qui sont à la fois des inhibiteurs de l'enzyme phosphodiestérase 4 (pde4) et des antagonistes du récepteur muscarinique m3, des procédés de préparation de tels composés, des compositions les contenant et leur utilisation thérapeutique. Dosage de binging m3: des cellules de clones cho-ki exprimant le récepteur m3 humain (swissprot p20309) ont été récoltées dans une solution saline tamponnée au phosphate sans ca ++ / mg ++ et recueillies par centrifugation à 1500 tr / min pendant 3 min. Les pastilles ont été remises en suspension dans du tampon a glacé (tris-hcl 15 mm ph 7,4, mgcl2 2 mm, edta 0,3 mm, egta 1 mm) et homogénéisées par un politron pbi (réglage 5 pendant 15 s). La fraction membranaire brute a été recueillie par deux étapes de centrifugation consécutives à 40000 g pendant 20 min à 4 ° c, séparées par une étape de lavage dans le tampon a. Les pastilles obtenues ont finalement été remises en suspension dans du tampon b (tris hcl 75 mm, ph 7,4, 12,5 mm). Mgcl2, edta 0,3 mm, egta 1 mm, saccharose 250 mm) et des aliquotes ont été stockés à - 80 ° c. Le jour de l'expérience, les membranes congelées ont été remises en suspension dans du tampon c (tris-hcl 50 mm, ph 7,4, mgcb 2,5 mm, edta 1 mm). Le ligand radioélectrique muscarinique non sélectif [3h] -n-méthyl scopolamine (mol. Pharmacol.45: 899-907) a été utilisé pour marquer les sites de liaison à m3. Les expériences de liaison ont été effectuées en double (courbes de concentration en dix points) dans des plaques à 96 puits à une concentration de radioligand de 0,1-0,3 nm. La liaison non spécifique a été déterminée en présence de n-méthyl scopolamine à froid 10 um. Les échantillons (volume final 0,75 ml) ont été incubés à la température ambiante pendant 90 minutes. La réaction a été arrêtée par filtration rapide à travers des plaques unifilter gf / b et deux lavages (0,75 ml) avec du tampon froid c en utilisant un harvester filtermate harvester. La radioactivité sur les filtres a été mesurée par un compteur à scintillation de microplaques tricarb 2500 (perkinelmer). Des composés représentatifs de l'invention, lorsqu'ils ont été testés dans l'un des protocoles mentionnés ci-dessus, ont présenté une ic50 inférieure à 100 nm. Des composés représentatifs de l'invention présentaient une ic50 inférieure à 100 nm à la fois dans les dosages sans cellules pde4 et dans les taux de liaison à m3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14171266 | 2014-06-05 | ||
| EP15731261.2A EP3152201B1 (fr) | 2014-06-05 | 2015-06-03 | Dérivés aminoestérifiés |
| PCT/EP2015/062417 WO2015185649A1 (fr) | 2014-06-05 | 2015-06-03 | Dérivés aminoesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MA39947A MA39947A (fr) | 2017-04-12 |
| MA39947B1 true MA39947B1 (fr) | 2018-10-31 |
Family
ID=50884281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MA39947A MA39947B1 (fr) | 2014-06-05 | 2015-06-03 | Dérivés aminoestérifiés |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US9763924B2 (fr) |
| EP (1) | EP3152201B1 (fr) |
| JP (1) | JP2017516824A (fr) |
| KR (1) | KR102420323B1 (fr) |
| CN (1) | CN106459020B (fr) |
| AR (1) | AR100732A1 (fr) |
| AU (1) | AU2015270539B2 (fr) |
| BR (1) | BR112016026725B1 (fr) |
| CA (1) | CA2953198C (fr) |
| CL (1) | CL2016003117A1 (fr) |
| CY (1) | CY1120698T1 (fr) |
| DK (1) | DK3152201T3 (fr) |
| EA (1) | EA032761B1 (fr) |
| ES (1) | ES2688826T3 (fr) |
| GE (1) | GEP20186922B (fr) |
| HR (1) | HRP20181967T1 (fr) |
| HU (1) | HUE042119T2 (fr) |
| IL (1) | IL249325B (fr) |
| LT (1) | LT3152201T (fr) |
| MA (1) | MA39947B1 (fr) |
| MX (1) | MX2016015958A (fr) |
| PE (1) | PE20161557A1 (fr) |
| PH (1) | PH12016502221A1 (fr) |
| PL (1) | PL3152201T3 (fr) |
| PT (1) | PT3152201T (fr) |
| RS (1) | RS57787B1 (fr) |
| SG (1) | SG11201610132RA (fr) |
| SI (1) | SI3152201T1 (fr) |
| TN (1) | TN2016000546A1 (fr) |
| TW (1) | TW201625600A (fr) |
| WO (1) | WO2015185649A1 (fr) |
| ZA (1) | ZA201608331B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016177849A1 (fr) | 2015-05-07 | 2016-11-10 | Chiesi Farmaceutici S.P.A. | Dérivés d'aminoesters |
| AR104829A1 (es) * | 2015-06-01 | 2017-08-16 | Chiesi Farm Spa | Derivados de aminoésteres |
| AR104822A1 (es) * | 2015-06-01 | 2017-08-16 | Chiesi Farm Spa | Derivado de aminoésteres |
| CN106866474B (zh) * | 2017-02-16 | 2018-12-28 | 陕西师范大学 | 一种手性α-芳基甘氨酸酯衍生物的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2022783A1 (fr) * | 2007-08-08 | 2009-02-11 | CHIESI FARMACEUTICI S.p.A. | Dérivés d'alcools 1-phényl-2-pyridinylalkyliques en tant qu'inhibiteurs de la phosphodiestérase |
| UY31637A1 (es) | 2008-02-06 | 2009-08-03 | Farmacoforos duales-antagonistas muscarinicos de pde4 | |
| EP2216327A1 (fr) * | 2009-02-06 | 2010-08-11 | CHIESI FARMACEUTICI S.p.A. | Benzoate de (1-Phenyl-2-Pyridin-4-yl)ethyle en tant qu'inhibiteurs de phosphodiestérase |
| TW201439089A (zh) | 2012-12-05 | 2014-10-16 | Chiesi Farma Spa | 新穎化合物 |
| TW201434817A (zh) * | 2012-12-05 | 2014-09-16 | Chiesi Farma Spa | 新穎化合物 |
| BR112015012949A2 (pt) | 2012-12-05 | 2017-07-11 | Chiesi Farm Spa | composto, composição farmaceutica, uso de um composto, dispositivo inalatório e kit |
| CA2932486A1 (fr) | 2013-12-05 | 2015-06-11 | Chiesi Farmaceutici S.P.A. | Derives benzhydryle pour le traitement de maladies respiratoires |
| KR20160086351A (ko) * | 2013-12-05 | 2016-07-19 | 키에시 파르마슈티시 엣스. 피. 에이. | 호흡기 질환의 치료를 위한 헤테로아릴 유도체 |
-
2015
- 2015-05-28 US US14/723,964 patent/US9763924B2/en active Active
- 2015-06-03 KR KR1020167032346A patent/KR102420323B1/ko active IP Right Grant
- 2015-06-03 BR BR112016026725-7A patent/BR112016026725B1/pt active Search and Examination
- 2015-06-03 SG SG11201610132RA patent/SG11201610132RA/en unknown
- 2015-06-03 AU AU2015270539A patent/AU2015270539B2/en not_active Expired - Fee Related
- 2015-06-03 JP JP2016571037A patent/JP2017516824A/ja not_active Withdrawn
- 2015-06-03 WO PCT/EP2015/062417 patent/WO2015185649A1/fr active Application Filing
- 2015-06-03 DK DK15731261.2T patent/DK3152201T3/en active
- 2015-06-03 HU HUE15731261A patent/HUE042119T2/hu unknown
- 2015-06-03 EA EA201692227A patent/EA032761B1/ru not_active IP Right Cessation
- 2015-06-03 MA MA39947A patent/MA39947B1/fr unknown
- 2015-06-03 EP EP15731261.2A patent/EP3152201B1/fr active Active
- 2015-06-03 SI SI201530392T patent/SI3152201T1/sl unknown
- 2015-06-03 CN CN201580029748.7A patent/CN106459020B/zh active Active
- 2015-06-03 LT LTEP15731261.2T patent/LT3152201T/lt unknown
- 2015-06-03 GE GEAP201514338A patent/GEP20186922B/en unknown
- 2015-06-03 PE PE2016002520A patent/PE20161557A1/es unknown
- 2015-06-03 CA CA2953198A patent/CA2953198C/fr active Active
- 2015-06-03 PT PT15731261T patent/PT3152201T/pt unknown
- 2015-06-03 RS RS20181192A patent/RS57787B1/sr unknown
- 2015-06-03 ES ES15731261.2T patent/ES2688826T3/es active Active
- 2015-06-03 TN TN2016000546A patent/TN2016000546A1/en unknown
- 2015-06-03 PL PL15731261T patent/PL3152201T3/pl unknown
- 2015-06-03 MX MX2016015958A patent/MX2016015958A/es active IP Right Grant
- 2015-06-04 AR ARP150101772A patent/AR100732A1/es unknown
- 2015-06-04 TW TW104118107A patent/TW201625600A/zh unknown
-
2016
- 2016-11-09 PH PH12016502221A patent/PH12016502221A1/en unknown
- 2016-12-01 IL IL249325A patent/IL249325B/en not_active IP Right Cessation
- 2016-12-02 ZA ZA2016/08331A patent/ZA201608331B/en unknown
- 2016-12-02 CL CL2016003117A patent/CL2016003117A1/es unknown
-
2017
- 2017-08-10 US US15/673,710 patent/US10117860B2/en active Active
-
2018
- 2018-09-24 CY CY181100984T patent/CY1120698T1/el unknown
- 2018-11-23 HR HRP20181967TT patent/HRP20181967T1/hr unknown
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