AR032134A1 - Compuestos derivados de propilo tienoisoxazolil- y tienilpirrazolil-fenoxi-substituidos utiles como antagonistas d4, composiciones farmaceuticas, procedimientos de preparacion, compuestos intermediarios y usos en la fabricacion de medicamentos - Google Patents
Compuestos derivados de propilo tienoisoxazolil- y tienilpirrazolil-fenoxi-substituidos utiles como antagonistas d4, composiciones farmaceuticas, procedimientos de preparacion, compuestos intermediarios y usos en la fabricacion de medicamentosInfo
- Publication number
- AR032134A1 AR032134A1 ARP000104793A ARP000104793A AR032134A1 AR 032134 A1 AR032134 A1 AR 032134A1 AR P000104793 A ARP000104793 A AR P000104793A AR P000104793 A ARP000104793 A AR P000104793A AR 032134 A1 AR032134 A1 AR 032134A1
- Authority
- AR
- Argentina
- Prior art keywords
- phenyl
- compounds
- alkyl
- pyridyl
- alkoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 239000005557 antagonist Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 2
- 125000001041 indolyl group Chemical group 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 208000011117 substance-related disease Diseases 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 abstract 1
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 abstract 1
- 206010000117 Abnormal behaviour Diseases 0.000 abstract 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 abstract 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 abstract 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 208000027089 Parkinsonian disease Diseases 0.000 abstract 1
- 206010034010 Parkinsonism Diseases 0.000 abstract 1
- 208000028017 Psychotic disease Diseases 0.000 abstract 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 abstract 1
- 208000016620 Tourette disease Diseases 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 abstract 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 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 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000543 intermediate Chemical class 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000009032 substance abuse Diseases 0.000 abstract 1
- 231100000736 substance abuse Toxicity 0.000 abstract 1
- 201000006152 substance dependence Diseases 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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
- A61P25/14—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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Un compuesto de formula (1) o una sal o estereoisomero farmacéuticamente aceptable del mismo, donde: X es N(CH3) u O; R1 es OH o alcoxi C1-6; R2 es H o alquilo C1-6; R3 es (CH2)nQ, CH2CH(OH)Q, CH(CH3)Q, 1,2,3,4-tetrahidronaftilo, indanilo o adamantilo, donde Q es tienilo, fenilo, furanilo, naftilo, piridilo, indolilo, indazolilo, ciclohexilo, 1,2-metilendioxifenilo, ciclohexenilo o 1H-pirazolo[4,3-c]piridilo, y Q está eventualmente substituido con uno o dos restos independientemente seleccionados entre halo, alquilo C1-6, alcoxi C1-6, hidroxi, S(O)2NH2, trifluorometilo o ciano y n es 2; R4 es H o alquilo C1-6; o R3 y R4, junto con el átomo de nitrogeno al que R3 y R4 están unidos, forman 1,4-dioxa-8-azoespiro[4.5]decanilo, piperazinilo, morfolinilo, piperidinilo, pirrolidinilo, azocanilo, 1,2,3,4-tetrahidroisoquinolinilo, 1,2,3,4-tetrahidro-B-carbolinilo, 4,5,6,7-tetrahidrotienil[3,2-c]piridilo o 8-azabiciclo[3.2.1]octano, cada uno de los cuales puede estar mono- o independientemente disubstituido con halo, alquilo C1-6, alcoxi C1-6, C(O)fenilo, OH, CN, O-fenilo o (CH2)mZ; Z es benzisoxazolilo, indazolilo, benzisotiazolilo, benzotienilo, pirimidinilo, piridilo, 1,2-metilendioxifenilo o fenilo; y Z, CH(OH)fenilo u O-fenilo están eventualmente substituidos con uno o dos restos independientemente seleccionados entre halo, alquilo C1-6, alcoxi C1-6; hidroxi, trifluorometilo, S(O)2NH2 o ciano, y m es 0 o 1; siempre que, cuando R1 es OH, R2 sea H: (a) cuando R4 es H y R3 es (CH2)nQ, donde n es 1 o 2, entonces Q no puede ser indolilo o fenilo; o (b) cuando R3 y R4 forman piperazinilo substituído con (CH2)mZ, cuando m es 1 entonces no puede ser fenilo. Una composicion farmacéutica que incluye los compuestos de formula (1) en mezcla con un vehículo farmacéuticamente aceptable. Procedimientos de preparacion de dicha clase de compuestos y compuestos intermediarios. Usos de los compuestos de formula (1) para la fabricacion de medicamentos para el tratamiento de condiciones médicas mediadas por la inhibicion del receptor D4. Estas condiciones comprenden, por ejemplo, el trastorno de hiperactividad con déficit de atencion, el trastorno obsesivo-compulsivo, las psicosis, el abuso de substancias, la dependencia de substancias, la enfermedad de Parkinson, el parkinsonismo, la disquinesia tardía, el síndrome de Gilles de la Tourette, el trastorno de la conducta y el trastorno de provocacion oposicion.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39608199A | 1999-09-14 | 1999-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR032134A1 true AR032134A1 (es) | 2003-10-29 |
Family
ID=23565772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000104793A AR032134A1 (es) | 1999-09-14 | 2000-09-13 | Compuestos derivados de propilo tienoisoxazolil- y tienilpirrazolil-fenoxi-substituidos utiles como antagonistas d4, composiciones farmaceuticas, procedimientos de preparacion, compuestos intermediarios y usos en la fabricacion de medicamentos |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1216250B1 (es) |
| JP (1) | JP4847662B2 (es) |
| KR (1) | KR20020027647A (es) |
| AR (1) | AR032134A1 (es) |
| AT (1) | ATE254621T1 (es) |
| AU (1) | AU7577400A (es) |
| BR (1) | BR0014515A (es) |
| CA (1) | CA2383340C (es) |
| CY (1) | CY1101692T1 (es) |
| CZ (1) | CZ2002897A3 (es) |
| DE (1) | DE60006699T2 (es) |
| DK (1) | DK1216250T3 (es) |
| EA (1) | EA200200355A1 (es) |
| EE (1) | EE200200135A (es) |
| ES (1) | ES2209995T3 (es) |
| HR (1) | HRP20020220A2 (es) |
| HU (1) | HUP0203526A3 (es) |
| IL (1) | IL148623A0 (es) |
| MX (1) | MXPA02002695A (es) |
| NO (1) | NO20021251L (es) |
| PL (1) | PL354515A1 (es) |
| PT (1) | PT1216250E (es) |
| SK (1) | SK3512002A3 (es) |
| TW (1) | TW530060B (es) |
| WO (1) | WO2001019833A1 (es) |
| ZA (1) | ZA200201762B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125903B1 (en) | 1999-09-14 | 2006-10-24 | Aventis Pharmaceuticals Inc. | Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists |
| US7091199B1 (en) | 1999-09-14 | 2006-08-15 | Aventis Pharmaceuticals Inc. | Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists |
| US7253165B2 (en) | 1999-09-14 | 2007-08-07 | Aventis Pharmaceuticals Inc. | Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists |
| JP4497815B2 (ja) * | 2001-02-16 | 2010-07-07 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 新規な複素環式アミド誘導体およびドーパミンｄ３受容体リガンドとしてのその使用 |
| US6982274B2 (en) | 2001-04-16 | 2006-01-03 | Eisai Co., Ltd. | 1H-indazole compound |
| KR20040020457A (ko) * | 2002-08-30 | 2004-03-09 | 주식회사 대웅 | 3-｛2-[4-(6-플루오로벤조[ｄ]이속사졸-3-일)피페리디노]에틸｝-2-메틸-6,7,8,9-테트라하이드로-4Ｈ-피리도[1,2-ａ]피리미딘-4-온 또는 그 산부가염의 제조방법 |
| NZ541306A (en) * | 2003-01-17 | 2008-07-31 | Cv Therapeutics Inc | Substituted piperazine and piperidine derivatives useful in the treatment of cardiovascular diseases |
| JP2007297321A (ja) * | 2006-04-28 | 2007-11-15 | Daiso Co Ltd | アリール２−メチルグリシジルエーテル類の製造法 |
| JP2007297330A (ja) * | 2006-04-28 | 2007-11-15 | Daiso Co Ltd | ２−メチルグリシジル誘導体の製造法 |
| US9221794B2 (en) | 2012-12-21 | 2015-12-29 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
| WO2014100695A1 (en) * | 2012-12-21 | 2014-06-26 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
| SI2935222T1 (sl) | 2012-12-21 | 2019-02-28 | Epizyme Inc. | Inhibitorji PRMT5 in njihove uporabe |
| JP2016505001A (ja) | 2012-12-21 | 2016-02-18 | エピザイム，インコーポレイティド | Ｐｒｍｔ５阻害剤およびその使用 |
| WO2014100730A1 (en) | 2012-12-21 | 2014-06-26 | Epizyme, Inc. | Prmt5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof |
| WO2015200680A2 (en) * | 2014-06-25 | 2015-12-30 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
| AU2015301196A1 (en) | 2014-08-04 | 2017-01-12 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728651A (en) * | 1985-10-24 | 1988-03-01 | Hoechst-Roussel Pharmaceuticals Inc. | Antihypertensive thieno-isoxazoles and -pyrazoles |
| US6187774B1 (en) * | 1996-03-04 | 2001-02-13 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and pharmaceutical applications thereof |
| HUP9603001A3 (en) * | 1996-10-30 | 1999-07-28 | Richter Gedeon Vegyeszet | Heterocycle compounds comprising nitrogen, process for producing them and pharmaceutical compositions containing the same |
| ES2291023T3 (es) * | 1998-02-09 | 2008-02-16 | Duphar International Research B.V | Derivados de benzisoxazol que tienen actividad antagonista de d4. |
-
2000
- 2000-09-13 AU AU75774/00A patent/AU7577400A/en not_active Abandoned
- 2000-09-13 MX MXPA02002695A patent/MXPA02002695A/es active IP Right Grant
- 2000-09-13 ES ES00964969T patent/ES2209995T3/es not_active Expired - Lifetime
- 2000-09-13 KR KR1020027003366A patent/KR20020027647A/ko not_active Withdrawn
- 2000-09-13 PT PT00964969T patent/PT1216250E/pt unknown
- 2000-09-13 AT AT00964969T patent/ATE254621T1/de not_active IP Right Cessation
- 2000-09-13 EP EP00964969A patent/EP1216250B1/en not_active Expired - Lifetime
- 2000-09-13 HR HR20020220A patent/HRP20020220A2/hr not_active Application Discontinuation
- 2000-09-13 PL PL00354515A patent/PL354515A1/xx unknown
- 2000-09-13 DE DE60006699T patent/DE60006699T2/de not_active Expired - Lifetime
- 2000-09-13 EE EEP200200135A patent/EE200200135A/xx unknown
- 2000-09-13 DK DK00964969T patent/DK1216250T3/da active
- 2000-09-13 HU HU0203526A patent/HUP0203526A3/hu unknown
- 2000-09-13 SK SK351-2002A patent/SK3512002A3/sk unknown
- 2000-09-13 BR BR0014515-7A patent/BR0014515A/pt not_active IP Right Cessation
- 2000-09-13 CA CA2383340A patent/CA2383340C/en not_active Expired - Fee Related
- 2000-09-13 JP JP2001523410A patent/JP4847662B2/ja not_active Expired - Fee Related
- 2000-09-13 IL IL14862300A patent/IL148623A0/xx unknown
- 2000-09-13 AR ARP000104793A patent/AR032134A1/es not_active Application Discontinuation
- 2000-09-13 EA EA200200355A patent/EA200200355A1/ru unknown
- 2000-09-13 CZ CZ2002897A patent/CZ2002897A3/cs unknown
- 2000-09-13 WO PCT/US2000/024962 patent/WO2001019833A1/en not_active Ceased
- 2000-09-14 TW TW089118850A patent/TW530060B/zh not_active IP Right Cessation
-
2002
- 2002-03-13 NO NO20021251A patent/NO20021251L/no not_active Application Discontinuation
- 2002-03-21 ZA ZA200201762A patent/ZA200201762B/en unknown
-
2004
- 2004-02-12 CY CY20041100175T patent/CY1101692T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0203526A3 (en) | 2004-12-28 |
| EA200200355A1 (ru) | 2002-10-31 |
| DE60006699D1 (en) | 2003-12-24 |
| MXPA02002695A (es) | 2002-07-30 |
| ATE254621T1 (de) | 2003-12-15 |
| CY1101692T1 (el) | 2010-07-28 |
| IL148623A0 (en) | 2002-09-12 |
| DE60006699T2 (de) | 2004-09-30 |
| NO20021251L (no) | 2002-05-10 |
| PT1216250E (pt) | 2004-04-30 |
| JP2003509432A (ja) | 2003-03-11 |
| AU7577400A (en) | 2001-04-17 |
| BR0014515A (pt) | 2002-06-25 |
| HRP20020220A2 (en) | 2004-02-29 |
| CZ2002897A3 (cs) | 2002-07-17 |
| JP4847662B2 (ja) | 2011-12-28 |
| EE200200135A (et) | 2003-04-15 |
| EP1216250B1 (en) | 2003-11-19 |
| SK3512002A3 (en) | 2003-03-04 |
| WO2001019833A1 (en) | 2001-03-22 |
| CA2383340C (en) | 2010-06-15 |
| CA2383340A1 (en) | 2001-03-22 |
| HUP0203526A2 (hu) | 2003-01-28 |
| TW530060B (en) | 2003-05-01 |
| ZA200201762B (en) | 2003-08-27 |
| ES2209995T3 (es) | 2004-07-01 |
| KR20020027647A (ko) | 2002-04-13 |
| EP1216250A1 (en) | 2002-06-26 |
| NO20021251D0 (no) | 2002-03-13 |
| PL354515A1 (en) | 2004-01-26 |
| DK1216250T3 (da) | 2004-02-23 |
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