AR082230A1 - DERIVATIVES OF TRIAZOLO- AND PIRAZOLOQUINAZOLINA AS INHIBITOR OF THE ENZYME PDE10A - Google Patents
DERIVATIVES OF TRIAZOLO- AND PIRAZOLOQUINAZOLINA AS INHIBITOR OF THE ENZYME PDE10AInfo
- Publication number
- AR082230A1 AR082230A1 ARP110102557A ARP110102557A AR082230A1 AR 082230 A1 AR082230 A1 AR 082230A1 AR P110102557 A ARP110102557 A AR P110102557A AR P110102557 A ARP110102557 A AR P110102557A AR 082230 A1 AR082230 A1 AR 082230A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- methoxy
- alkyl
- ethoxy
- butyl
- Prior art date
Links
- 101001072037 Homo sapiens cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- -1 methoxy, dimethoxy, ethoxy, methoxy-ethoxy Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/18—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Su uso como ingredientes farmacéuticos, en particular para el tratamiento de enfermedades relacionadas con el SNC.Reivindicación 1: El compuesto de fórmula (1) donde R1 - R4 se selecciona del grupo integrado por H; alquilo C1-6 tal como metilo; halógeno tal como cloro y bromo; ciano; haloalquilo C1-6 tal como trifluorometilo; arilo tal como fenilo; alcoxi, tal como metoxi, dimetoxi, etoxi, metoxi-etoxi y etoxi-metoxi, e hidroxialquilo C1-6 tal como CH2CH2OH; y donde Y se selecciona del grupo integrado por N, CH, o C-CN; y donde het se selecciona del grupo integrado por las fórmulas (2) donde * indica el punto de unión; y donde R5 y R6 pueden ser seleccionados individualmente del grupo integrado por alquilo C1-6 tal como metilo, etilo, 1-propilo, 2-propilo, isobutilo, n- butilo, sec-butilo o ter-butilo; H; alquil C1-6-cicloalquilo C3-8 tal como ciclopropilmetilo; hidroxialquilo C1-6 tal como hidroxietilo; CH2CN; CH2C(O)NH2; arilalquilo C1-6 tal como bencilo y 4-clorobencilo; y alquil C1-6-heterocicloalquilo tal como tetrahidropiran-4-il-metilo y 2-morfolin-4-il-etilo; y donde R7 - R11 se selecciona del grupo integrado por H; alcoxi C1-6 tal como metoxi; y halógeno tal como cloro o flúor; y donde además L es un conector seleccionado del grupo integrado por -CH2-CH2-, -S-CH2- y -CH2-S-; así como sus tautómeros y sales de adición de ácidos farmacéuticamente aceptables.Its use as pharmaceutical ingredients, in particular for the treatment of CNS-related diseases. Claim 1: The compound of formula (1) wherein R1-R4 is selected from the group consisting of H; C1-6 alkyl such as methyl; halogen such as chlorine and bromine; cyano; C1-6 haloalkyl such as trifluoromethyl; aryl such as phenyl; alkoxy, such as methoxy, dimethoxy, ethoxy, methoxy-ethoxy and ethoxy-methoxy, and C1-6 hydroxyalkyl such as CH2CH2OH; and where Y is selected from the group consisting of N, CH, or C-CN; and where het is selected from the group consisting of formulas (2) where * indicates the point of attachment; and where R5 and R6 can be individually selected from the group consisting of C1-6 alkyl such as methyl, ethyl, 1-propyl, 2-propyl, isobutyl, n-butyl, sec-butyl or tert-butyl; H; C 1-6 alkyl C 3-8 cycloalkyl such as cyclopropylmethyl; C1-6 hydroxyalkyl such as hydroxyethyl; CH2CN; CH2C (O) NH2; C 1-6 arylalkyl such as benzyl and 4-chlorobenzyl; and C1-6 alkyl heterocycloalkyl such as tetrahydropyran-4-yl-methyl and 2-morpholin-4-yl-ethyl; and where R7-R11 is selected from the group consisting of H; C1-6 alkoxy such as methoxy; and halogen such as chlorine or fluorine; and where also L is a connector selected from the group consisting of -CH2-CH2-, -S-CH2- and -CH2-S-; as well as its tautomers and pharmaceutically acceptable acid addition salts.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201000637 | 2010-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR082230A1 true AR082230A1 (en) | 2012-11-21 |
Family
ID=44511687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110102557A AR082230A1 (en) | 2010-07-16 | 2011-07-15 | DERIVATIVES OF TRIAZOLO- AND PIRAZOLOQUINAZOLINA AS INHIBITOR OF THE ENZYME PDE10A |
Country Status (3)
| Country | Link |
|---|---|
| AR (1) | AR082230A1 (en) |
| TW (1) | TW201206935A (en) |
| WO (1) | WO2012007006A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140009372A (en) | 2011-02-18 | 2014-01-22 | 알러간, 인코포레이티드 | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| WO2013107856A1 (en) * | 2012-01-20 | 2013-07-25 | H. Lundbeck A/S | Imidazole derivatives as pde10a enzyme inhibitors |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| KR102706457B1 (en) * | 2018-12-06 | 2024-09-11 | 한국화학연구원 | Compound for inhibiting PDE9A and medical uses thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8307865D0 (en) | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| US5571775A (en) | 1994-07-11 | 1996-11-05 | Dowelanco | N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides |
| US20030032579A1 (en) | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| IL149106A0 (en) | 2001-04-20 | 2002-11-10 | Pfizer Prod Inc | Therapeutic use of selective pde10 inhibitors |
| US20070105840A1 (en) | 2003-06-30 | 2007-05-10 | Altana Pharma Ag | Pyrrolo-dihydroisoquinoline derivatives as pde10 inhibitors |
| CN1809565A (en) | 2003-06-30 | 2006-07-26 | 奥坦纳医药公司 | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| WO2005012485A2 (en) | 2003-07-31 | 2005-02-10 | Bayer Pharmaceuticals Corporation | Methods for treating diabetes and related disorders using pde10a inhibitors |
| JP2007523152A (en) | 2004-02-18 | 2007-08-16 | ファイザー・プロダクツ・インク | Tetrahydroisoquinolinyl derivatives of quinazoline and isoquinoline |
| JP2008501776A (en) | 2004-06-07 | 2008-01-24 | ファイザー・プロダクツ・インク | Inhibition of phosphodiesterase 10 as a treatment for conditions associated with obesity and associated with metabolic syndrome |
| US20060019975A1 (en) | 2004-07-23 | 2006-01-26 | Pfizer Inc | Novel piperidyl derivatives of quinazoline and isoquinoline |
| US20060160814A1 (en) | 2004-09-03 | 2006-07-20 | Arrington Mark P | Phosphodiesterase 10 inhibitors |
| WO2009070583A1 (en) * | 2007-11-30 | 2009-06-04 | Wyeth | Pyrido[3,2-e]pyrazines, process for preparing the same, and their use as inhibitors of phosphodiesterase 10 |
| TWI501965B (en) | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | Novel phenylimidazole derivatives as pde10a enzyme inhibitors |
-
2011
- 2011-07-07 TW TW100124014A patent/TW201206935A/en unknown
- 2011-07-15 WO PCT/DK2011/050278 patent/WO2012007006A1/en not_active Ceased
- 2011-07-15 AR ARP110102557A patent/AR082230A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012007006A1 (en) | 2012-01-19 |
| TW201206935A (en) | 2012-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |