DK2758394T3 - Heteroarylforbindelser som 5-ht4-receptorligander - Google Patents
Heteroarylforbindelser som 5-ht4-receptorligander Download PDFInfo
- Publication number
- DK2758394T3 DK2758394T3 DK12716662.7T DK12716662T DK2758394T3 DK 2758394 T3 DK2758394 T3 DK 2758394T3 DK 12716662 T DK12716662 T DK 12716662T DK 2758394 T3 DK2758394 T3 DK 2758394T3
- Authority
- DK
- Denmark
- Prior art keywords
- oxadiazol
- piperidin
- chloro
- ylamine
- chroman
- Prior art date
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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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
- A61K31/41—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
- A61K31/4245—Oxadiazoles
-
- 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
- A61P25/14—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
- A61P25/18—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
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Semiconductor Integrated Circuits (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Claims (9)
1. Forbindelse med den almene formel (I):
hvor, er er eller er bindingspunkt;
Ri er alkyl, R3-O-R3 eller R2 er cycloalkyl eller heterocyclyl og eventuelt substitueret med hydrogen, alkyl eller -CO-OR3; R3 er alkyl; "Y" er C eller O; "m" er et heltal i intervallet fra 0 til 1; med det forbehold, når m er 0, så er R 1 cycloalkyl eller heterocyclyl; "n" er et heltal i intervallet fra 0 til 2; "p" er et heltal i intervallet fra 0 til 1; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, der er udvalgt fra gruppen bestående af: 6-chlor-8-[5-(l-cyclopropyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin- hemifumarat; 6-chlor-8-[5-(l-cyclobutyl piperidin-4-ylmethyl)-[l,3,4]oxadiazol-2-yl]-chroman-5- ylamin L(+)-tartratsalt; 6-chlor-8-[5-(l-cyclobutyl piperidin-4-ylmethyl)-[l,3,4]oxadiazol-2-yl]-chroman-5- ylamin; 1 -isopropyl-3 - {5-[l -(3 -methoxypropyl)piperidin-4-yl] -[ 1,3,4] oxadiazol-2-yl} -1H-indazoloxalatsalt; 3- [5-(l-cyclobutyl-piperidin-4-yl methyl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-lH-indazol L(+)-tartratsalt; 6-chlor-8-[5-(3-cyclobutyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]chroman- 5-ylamin-oxalatsalt; 4- [5-(8-amino-7-chlor-2,3-dihydrobenzo[l,4]dioxan-5-yl)-[l,3,4]oxadiazol-2-yl]-[ 1,4 ’ jbipiperidinyl-1 ’ -carboxylsyre-ethylesteroxalatsalt; 5- chlor-7-{5-[l-(tetrahydropyran-4-yl)piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-2,3-dihydro, benzofuran-4-ylamin-oxalatsalt; 6-chlor-8-{5-[l-(2-methoxy-ethyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-chroman-5- ylamin; 6-chlor-8- {5-[ 1 -(3-methyl-butyl)-piperidin-4-yl]-[l ,3,4]oxadiazol-2-yl} -chroman-5-ylamin; 6-chlor-8-[5-(l,-cyclobutylmethyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5- ylamin; 6-chlor-8-[5-(l-cyclopropylmethyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5- ylamin; 6-chlor-8-[5-(l-isopropyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin; 6-chlor-8-{5-[l-(3-methoxy-propyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-chroman-5- ylamin; 6-chlor-8-[5-(l-cyclobutyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin; 6-chlor-8-[5-(l-cyclobutylmethyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-2,3-dihydro-benzo [ 1,4] dioxin-5 -ylamin; 6-chlor-8-[5-(l-cyclobutyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-2,3-dihydro-benzo [ 1,4] dioxin-5 -ylamin; 6-chlor-8-[5-(l-cyclopentyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin; 6-chlor-8-[5-(2-piperidin-l-yl-ethyl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin; 4- [5-(5-Amino-6-chlor-chroman-8-yl)-[l,3,4]oxadiazol-2-yl]-[l,4’]bipiperidinyl-l ’-carboxylsyre-ethylester; 6-chlor-8-[5-(3-piperidin-l-yl-propyl)-[l,3,4]oxadiazol-2-yl]-chroman-5-ylamin; 6-chlor-8-[5-(l-cyclopentyl-piperidin-4-ylmethyl)-[l,3,4]oxadiazol-2-yl]-chroman-5- ylamin-oxalatsalt; 6-chlor-8 -[5 -(3 -isopropyl-3 -aza-bicyclo [3.1.0]hex-6-yl)- [ 1,3,4] oxadiazol-2-yl] -chroman- 5- ylamin-oxalatsalt; 6- chlor-8-[5-(3-cyclobutylmethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5 -ylamin-oxalatsalt; 6-chlor-8-[5-(3-cyclopropylmethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]-chroman-5 -ylamin; 6-chlor-8- {5-[ 1 -(tetrahydro-pyran-4-yl)-piperidin-4-yl]-[l ,3,4]oxadiazol-2-yl} -chroman- 5- ylamin-oxalatsalt; 6- chlor-8- {5-[ 1 -(tetrahydro-pyran-4-ylmethyl)-piperidin-4-yl]-[l ,3,4]oxadiazol-2-yl} -chroman-5 -ylamin-oxalatsalt; 5-chlor-7-[5-(l-cyclopropyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-2,3-dihydro- benzofuran-4-ylamin-oxalatsalt; 5-chlor-7-[5-(l-cyclobutyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-2,3-dihydro-benzofuran- 4-vlamin-oxalatsalt; 6-chlor-8-[5-(l-cyclopropyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-2,3-dihydro-benzo [ 1,4] dioxin-5 -ylamin-oxalatsalt; 6-chlor-8- {5-[ 1 -(tetrahydro-pyran-4-yl)-piperidin-4-yl]-[l ,3,4]oxadiazol-2-yl} -2,3-dihydro-benzo[l,4]dioxin-5-ylamin-oxalatsalt; 6-chlor-8-{5-[l-(3-methoxy-propyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-2,3-dihydro-benzo [ 1,4] dioxin-5 -ylamin-oxalatsalt; 6-chlor-8-{5-[l-(tetrahydro-pyran-4-ylmethyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-2,3- dihydro-benzo[l,4]dioxin-5-ylamin-oxalatsalt; 5-chlor-7 - {5-[ 1 -(tetrahydro-pyran-4-ylmethyl)-piperidin-4-yl] -[ 1,3,4]oxadiazol-2-yl} -2,3 -dihydro-benzofuran-4-ylaminoxalat; 4-[5-(4-amino-5-chlor-2,3-dihydro-benzofuran-7-yl)-[l,3,4]oxadiazol-2-yl]-[ 1,4’]bipiperidinyl-l’-carboxylsyre ethylesteroxalat; 3-[5-(l-cyclobutylmethyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-1 H-indazol; 1 -isopropyl-3- {5-[l -(2-methoxy-ethyl)-piperidin-4-yl]-[l ,3,4]oxadiazol-2-yl} - 1H-indazol; 3 -[5-( 1 -cyclobutyl-piperidin-4-yl)- [ 1,3,4] oxadiazol-2-yl] -1 -isopropyl-1 H-indazol; 1 -isopropyl-3 - [5 -(1 -isopropyl-piperidin-4-yl)- [ 1,3,4] oxadiazol-2-yl] -1 H-indazol; 3 -[5-( 1 -cyclopropylmethyl-piperidin-4-yl)- [ 1,3,4] oxadiazol-2-yl] -1 -isopropyl-1 H-indazol; 1-isopropyl-3-{5-[l-(3-methyl-butyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-lH-indazol; 3-[5-(l-cyclopropyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-lH-indazol; 3-[5-(l-cyclopentyl-piperidin-4-yl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-lH-indazol; 1- isopropyl-3-{5-[3-(3-methoxy-propyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-[l,3,4]oxadiazol- 2- yl} -lH-indazoloxalatsalt; 3- [5-(3-cyclobutyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-lH-indazoloxalatsalt; 3-[5-(3-cyclobutylmethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]-l- isopropyl-lH-indazoloxalatsalt; 3-[5-(3-cyclopropylmethyl-3-aza-bicyclo[3.1.0]hex-6-yl)-[l,3,4]oxadiazol-2-yl]-l- isopropyl-lH-indazoloxalatsalt; 1-isopropyl-3-{5-[l-(tetrahydro-pyran-4-ylmethyl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl} - lH-indazoloxalatsalt; 1-isopropyl-3-{5-[l-(tetrahydro-pyran-4-yl)-piperidin-4-yl]-[l,3,4]oxadiazol-2-yl}-lH-indazoloxalatsalt; 1 -isopropyl-3 - [5 -(2-piperidin-1 -yl-ethyl)-[ 1,3,4] oxadiazol-2-yl] -1 H-indazoloxalatsalt og 3-[5-(l-cyclobutyl piperidin-4-yl methyl)-[l,3,4]oxadiazol-2-yl]-l-isopropyl-lH-indazoloxalatsalt; eller farmaceutisk acceptable salte deraf.
3. Fremgangsmåde til fremstilling af en forbindelse med formlen (I) ifølge krav 1, hvilken fremgangsmåde omfatter: (a) kobling af forbindelsen med formlen (1) med forbindelsen med formlen (2)
i nærvær af dehydreringsmiddel for at danne en forbindelse med formlen (1), hvor samtlige substitutioner er som defineret i krav 1, (b) eventuel omdannelse af forbindelsen med formlen (1) til farmaceutisk acceptable salte deraf.
4. Fremgangsmåde til fremstilling af en forbindelse med formlen (1) ifølge krav 1, hvilken fremgangsmåde omfatter: (a) kobling af forbindelsen med formlen (1) med forbindelsen med formlen (2)
i nærvær af et egnet opløsningsmiddel for at danne en forbindelse med formlen (4),
(b) cyklisering af forbindelsen med formlen (4) for at danne en forbindelse med formlen (I), hvor samtlige substitutioner er som defineret i krav 1, (c) eventuel omdannelse af forbindelsen med formlen (I) til de farmaceutisk acceptable salte deraf.
5. Farmaceutisk sammensætning omfattende en forbindelse ifølge et hvilket som helst af kravene 1 til 2 og farmaceutisk acceptable excipienser.
6. Farmaceutisk sammensætning ifølge krav 5 til behandling af kliniske tilstande medieret via 5- HT4-receptorer, såsom ADHD, alzheimers sygdom, kognitive forstyrrelser, demens eller skizofreni.
7. Forbindelse ifølge et hvilket som helst af kravene 1 til 2 til anvendelse i behandling af sygdomme relateret til 5-HT4-receptorer.
8. Forbindelse ifølge krav 7, til anvendelse in behandling af kliniske tilstande såsom ADHD, alzheimers sygdom, kognitive forstyrrelser, demens eller skizofreni.
9. Forbindelse med formlen (I) ifølge krav 1 eller krav 2 til anvendelse i behandling af forstyrrelse i centralnervesystemet relateret til eller påvirket af 5-HT 4-receptoreme.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3203CH2011 | 2011-09-19 | ||
| PCT/IN2012/000011 WO2013042135A1 (en) | 2011-09-19 | 2012-01-05 | Heteroaryl compounds as 5-ht4 receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2758394T3 true DK2758394T3 (da) | 2015-04-20 |
Family
ID=46001349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12716662.7T DK2758394T3 (da) | 2011-09-19 | 2012-01-05 | Heteroarylforbindelser som 5-ht4-receptorligander |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US9079894B2 (da) |
| EP (1) | EP2758394B1 (da) |
| JP (1) | JP5714729B2 (da) |
| KR (1) | KR101551481B1 (da) |
| CN (1) | CN103380131B (da) |
| AP (1) | AP3307A (da) |
| AU (1) | AU2012311057B2 (da) |
| BR (1) | BR112014001083B8 (da) |
| CA (1) | CA2823548C (da) |
| CY (1) | CY1116173T1 (da) |
| DK (1) | DK2758394T3 (da) |
| EA (1) | EA022374B1 (da) |
| ES (1) | ES2531885T3 (da) |
| HK (1) | HK1187340A1 (da) |
| HR (1) | HRP20150229T1 (da) |
| IL (1) | IL231305A0 (da) |
| ME (1) | ME02107B (da) |
| MX (1) | MX337721B (da) |
| PL (1) | PL2758394T3 (da) |
| PT (1) | PT2758394E (da) |
| RS (1) | RS53940B1 (da) |
| SG (1) | SG2014003560A (da) |
| SI (1) | SI2758394T1 (da) |
| SM (1) | SMT201500087B (da) |
| WO (1) | WO2013042135A1 (da) |
| ZA (1) | ZA201309100B (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2833507A1 (en) * | 2011-06-07 | 2012-12-13 | Dainippon Sumitomo Pharma Co., Ltd. | Indazole- and pyrrolopyridine-derivative and pharmaceutical use thereof |
| CN105120851A (zh) * | 2013-04-05 | 2015-12-02 | Abc生物科学公司 | 用于医疗用途，具体为用于治疗与氧化应激相关的疾病或者炎症和用于保存或者洗涤器官的barettin及其衍生物 |
| EP3099675B1 (en) | 2013-12-16 | 2018-02-14 | Suven Life Sciences Limited | Indazole compounds as 5-ht4 receptor agonists |
| EP3180333B1 (en) * | 2014-08-16 | 2020-07-08 | Suven Life Sciences Limited | Process for large scale production of 1-isopropyl-3-{5- [1-(3-methoxypropyl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-1h-indazole oxalate |
| MA41633B1 (fr) * | 2015-02-13 | 2019-07-31 | Suven Life Sciences Ltd | Composés amide en tant qu'agonistes du récepteur 5-ht4 |
| CN107540568A (zh) * | 2017-08-25 | 2018-01-05 | 许昌恒生制药有限公司 | 一种乙氧酰胺苯甲酯的制备方法 |
| US20210386727A1 (en) * | 2018-10-18 | 2021-12-16 | Suven Life Sciences Limited | New uses of a 5-ht4 receptor agonist |
| WO2020243423A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| CN110746450A (zh) * | 2019-09-17 | 2020-02-04 | 济南康和医药科技有限公司 | 一种贝前列素钠关键中间体的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0596933A1 (en) * | 1991-08-03 | 1994-05-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| TW360653B (en) * | 1995-03-01 | 1999-06-11 | Janssen Pharmaceutica Nv | A oxadiazole compound having colon motility stimulating properties, its preparation process and its pharmaceutical composition |
| SK282335B6 (sk) * | 1995-11-09 | 2002-01-07 | Sanofi-Synthelabo | Deriváty 5-fenyl-3-(piperidin-4-yl)-1,3,4,-oxadiazol-2(3H)-ónu, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje |
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| BRPI0416813A (pt) | 2003-11-24 | 2007-03-06 | Pfizer | compostos de ácido quinolonacarboxìlico com atividade agonista do receptor 5-ht4 |
| AP2007004067A0 (en) * | 2005-02-22 | 2007-08-31 | Pfizer | Oxyindole derivatives as 5HT4 receptor agonists |
| CA2598516C (en) | 2005-02-25 | 2010-05-11 | Pfizer Inc. | Benzisoxazole derivatives |
| EP1910340B1 (en) | 2005-07-22 | 2009-11-18 | Pfizer, Inc. | Indazolecarboxamide derivatives as 5ht4 receptor agonists |
| CA2633425A1 (en) * | 2005-12-23 | 2007-06-28 | F. Hoffmann-La Roche Ag | Aryl-isoxazolo-4-yl-oxadiazole derivatives |
| US20080167286A1 (en) * | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| US20080255203A1 (en) * | 2007-04-12 | 2008-10-16 | Abbott Laboratories | Heterocyclic compounds and their methods of use |
| JP5656880B2 (ja) * | 2009-03-09 | 2015-01-21 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | Ｐｉ３キナーゼの阻害剤としての４−オキサジアゾール−２−イル−インダゾール |
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2012
- 2012-01-05 MX MX2013014577A patent/MX337721B/es active IP Right Grant
- 2012-01-05 SI SI201230163T patent/SI2758394T1/sl unknown
- 2012-01-05 CA CA2823548A patent/CA2823548C/en active Active
- 2012-01-05 CN CN201280009072.1A patent/CN103380131B/zh active Active
- 2012-01-05 ME MEP-2015-47A patent/ME02107B/me unknown
- 2012-01-05 ES ES12716662.7T patent/ES2531885T3/es active Active
- 2012-01-05 SG SG2014003560A patent/SG2014003560A/en unknown
- 2012-01-05 WO PCT/IN2012/000011 patent/WO2013042135A1/en active Application Filing
- 2012-01-05 KR KR1020137020582A patent/KR101551481B1/ko active IP Right Grant
- 2012-01-05 JP JP2013554062A patent/JP5714729B2/ja active Active
- 2012-01-05 EP EP12716662.7A patent/EP2758394B1/en active Active
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- 2012-01-05 PL PL12716662T patent/PL2758394T3/pl unknown
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- 2012-01-05 US US13/982,486 patent/US9079894B2/en active Active
- 2012-01-05 PT PT127166627T patent/PT2758394E/pt unknown
- 2012-01-05 BR BR112014001083A patent/BR112014001083B8/pt not_active IP Right Cessation
- 2012-01-05 DK DK12716662.7T patent/DK2758394T3/da active
- 2012-01-05 RS RS20150234A patent/RS53940B1/en unknown
- 2012-01-05 AU AU2012311057A patent/AU2012311057B2/en active Active
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2013
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2015
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- 2015-06-10 US US14/735,237 patent/US9636335B2/en active Active
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