KR910009700A - 3-피페리디닐-1,2-벤즈이속사졸 - Google Patents
3-피페리디닐-1,2-벤즈이속사졸 Download PDFInfo
- Publication number
- KR910009700A KR910009700A KR1019890016114A KR890016114A KR910009700A KR 910009700 A KR910009700 A KR 910009700A KR 1019890016114 A KR1019890016114 A KR 1019890016114A KR 890016114 A KR890016114 A KR 890016114A KR 910009700 A KR910009700 A KR 910009700A
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- South Korea
- Prior art keywords
- compound
- alkyl
- general formula
- acid addition
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- FFESGTAUFAZQRI-UHFFFAOYSA-N 3-piperidin-1-yl-1,2-benzoxazole Chemical compound C1CCCCN1C1=NOC2=CC=CC=C12 FFESGTAUFAZQRI-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012442 inert solvent Substances 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 230000000561 anti-psychotic effect Effects 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- -1 6-fluoro-1,2-benzisoxazol-3-yl Chemical group 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- IHJBKXUOSUJVJB-UHFFFAOYSA-N 9-hydroxy-2-methyl-1,2,3,6-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound OC=1C=CCN2C1NC(CC2=O)C IHJBKXUOSUJVJB-UHFFFAOYSA-N 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000002081 enamines Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
Claims (10)
- 일반식(Ⅰ)의 화합물 그 산부가염 또는 그 입체 이성체.위의 일반식에서, AIk는 C1-4알칸리일이고, R1은 수소, C1-4알킬 또는 할로이고, R2는 C1-4알킬이고, R3는 히드록시 또는 R4-C(=O)O이고, R4는 C1-19알킬이다.
- 제1항에 있어서, R3이 6,7,8,9-테트라히드로-2-C1-4알킬-4H-피리도[1,2-a]피리미딘-4-온 부분의 9위치에 치환된 일반식(I)의 화합물, 그 산부가염 또는 그 입체 이성체.
- 제2항에 있어서, AIk가 에탄리일, R1이 할로이고, R2가 메틸인 일반식(I)의 화합물, 그 산부가염 또는 그 입체이성체.
- 제1항에 있어서, 3-[2-[4-(6-플루오로-1,2-벤즈이속사졸-3-일)-1-피페리디닐]에틸-6,7,8,9-테트라히드로-9-히드록시-2-메틸-4H-피리도[1,2-a]피리미딘-4-온, 그 산부가염 또는 그 거울상체(enatiomer)인 화합물.
- 유효성분으로 일반식(I)의 화합물, 그 산부가염 또는 그 입체이성체를 항정신병성 치료효과량과 함께 불활성 담체로 조성된 항정신병성 약제조성물.위의 일반식에서, AIk는 C1-4알칸리일이고, R1은 수소, C1-4알킬 또는 할로이고, R2는 C1-4알킬이고, R3는 히드록시 또는 R4-C(=O)O이고, R4는 C1-19알킬이다.
- 제5항에 있어서, R3이 6,7,8,9-테트라히드로-2-C1-4알킬-4H-피리도[1,2-a]피리미딘-4-온 부분의 9위치에 치환된 약제조성물.
- 제5항에 있어서, 3-[2-[4-(6-플루오로-1,2-벤즈이속사졸-3-일)-1-피페리디닐]에틸]-6,7,8,9-테트라히드로-9-히드록시-2-메틸-4H-피리도[1,2-a]피리미딘-4-온, 그 산부가염 또는 그 거울상체인 약제 조성물.
- 일반식(I)의 화합물, 그 산부가염 또는 그 입체이성체를 항정신병성 치료효과량 온형동물에 투여하여, 정신병성 질환에 걸린 온혈동물을 치료하는 방법.위의 일반식에서, AIk는 C1-4알칸리일이고, R1은 수소, C1-4알킬 또는 할로이고, R2는 C1-4알킬이고, R3는 히드록시 또는 R4-C(=O)O이고, R4는 C1-19알킬이다.
- 제8항에 있어서, R3이 6,7,8,9-테트라히드로-2-C1-4알킬-4H-피리도[1,2-a]피리미딘-4-온 부분의 9위치에 치환된 일반식(I)의 화합물, 그 산부가염 또는 입체이성체를 항정신병성 치료효과량 온형동물에 투여하여, 정신병성 질환에 걸린 온형동물을 치료하는 방법.
- a)일반식(Ⅱ)의 3-피페리디닐-1,2-벤즈이속사졸을 불활성 용매중에서 승온하에 일반식(Ⅲ)의 화합물로 N-알킬화하거나, b)일반식(Ⅳ)의 욕심을 반응불활성 용매중에서 염기와 함께 승온하에 폐환 반응시키거나, c)일반식(V)의 활성옥심을 불활성 용매중에서 염기와 함께 승온하에 폐환 반응시키거나, d)일반식(I-a)의 화합물을 일반식(Ⅵ)의 카르복시산 또는 그 반응성 유도체를 불활성 용매 중에서 O-아실화하거나, e)일반식(VⅡ)의 아미딘을 일반식(VⅢ)의 -디카르보닐 중간화합물로 불활성용매중에서 승온하에 폐환 반응시키거나, f)일반식(IX)의 화합물을 일반식(X)의 에나민을 불활성 용매중에서 승온하에 폐환 반응시키거나, g)일반식(I-a)의 화합물의 라세미체 혼합물을, 분해제에 의해 부분입체 이성질체염 또는 화합물의 혼합물로 전환시키기고, 부분입체이성체 또는 화합물의 혼합물을 분리한후, 분리한 부분입체 이성체염 또는 화합물을 일반식(I-a)의 화합물의 상응하는 거울상체로 전환시켜 일반식(I)의 화합물, 그 산부가염 또는 그 입체이성체를 제조하는 방법.위의 일반식에서, AIk는 C1-4알칸디일이고, R1은 수소, C1-4알킬 또는 할로이고, R2는 C1-4알킬이고, R3는 히드록시 또는 R4-C(=O)O이고, R4는 C1-19알킬이고, Y는 반응성 이탈기이고, L은 산의 잔기이고, R5는 반응성 이탈기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26785788A | 1988-11-07 | 1988-11-07 | |
| US267857 | 1988-11-07 | ||
| US267,857 | 1988-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910009700A true KR910009700A (ko) | 1991-06-28 |
| KR0146053B1 KR0146053B1 (ko) | 1998-08-17 |
Family
ID=23020416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890016114A Expired - Lifetime KR0146053B1 (ko) | 1988-11-07 | 1989-11-07 | 3-피페리디닐-1,2-벤즈이속사졸 |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0368388B1 (ko) |
| JP (1) | JP2758045B2 (ko) |
| KR (1) | KR0146053B1 (ko) |
| AT (1) | ATE122349T1 (ko) |
| AU (1) | AU614437B2 (ko) |
| CA (1) | CA2000786C (ko) |
| CL (1) | CL43432B (ko) |
| CY (2) | CY1926A (ko) |
| DE (2) | DE68922577T2 (ko) |
| DK (1) | DK169923B1 (ko) |
| ES (1) | ES2075036T3 (ko) |
| FI (1) | FI92201C (ko) |
| HK (1) | HK131696A (ko) |
| IE (1) | IE66370B1 (ko) |
| IL (1) | IL92208A0 (ko) |
| LU (1) | LU91362I2 (ko) |
| NL (1) | NL300298I2 (ko) |
| NO (2) | NO173015C (ko) |
| NZ (1) | NZ231062A (ko) |
| PT (1) | PT92206B (ko) |
| ZA (1) | ZA898436B (ko) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9008850D0 (en) * | 1990-04-19 | 1990-06-13 | Janssen Pharmaceutica Nv | Novel 2,9-disubstituted-4h-pyridol(1,2-a)pyrimidin-4-ones |
| NZ245260A (en) * | 1991-11-27 | 1995-06-27 | Novo Nordisk As | Piperidine derivatives, preparation and pharmaceutical compositions thereof |
| US5378714A (en) * | 1991-11-27 | 1995-01-03 | Novo Nordisk A/S | Antipsychotic piperidine derivatives |
| ES2050069B1 (es) * | 1992-07-10 | 1994-12-16 | Vita Invest Sa | Procedimiento para la obtencion de 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-il)piperidino)etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido(1,2-a) pirimidin-4-ona. |
| DK60593D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
| DK60793D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
| RU2178695C2 (ru) * | 1993-11-19 | 2002-01-27 | Жансен Фармасетика Н.В. | Микрокапсулы, содержащие рисперидон, фармацевтическая композиция и способы их получения |
| ES2137486T3 (es) * | 1993-11-23 | 1999-12-16 | Janssen Pharmaceutica Nv | Derivados de 9-hidroxi-pirido(1,2-a)pirimidin-4-ona-eter. |
| ES2085234B1 (es) * | 1994-02-24 | 1997-01-16 | Vita Invest Sa | Agente activo sobre el sistema nervioso central, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| TW487572B (en) * | 1996-05-20 | 2002-05-21 | Janssen Pharmaceutica Nv | Aqueous suspensions of 9-hydroxyrisperidone fatty acid esters |
| US6028083A (en) * | 1997-07-25 | 2000-02-22 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| UA72189C2 (uk) * | 1997-11-17 | 2005-02-15 | Янссен Фармацевтика Н.В. | Фармацевтична композиція, що містить водну суспензію субмікронних ефірів 9-гідроксирисперидон жирних кислот |
| ES2141671B1 (es) * | 1997-12-26 | 2001-01-01 | Vita Invest Sa | Compuesto pirimidinico activo sobre el sistema nervioso central, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| AU3984899A (en) | 1998-05-18 | 1999-12-06 | Sepracor, Inc. | (-)-hydroxyrisperidone compositions and methods |
| WO1999059590A1 (en) * | 1998-05-18 | 1999-11-25 | Sepracor Inc. | (+)-hydroxyrisperidone compositions and methods |
| US6342488B1 (en) | 1998-08-18 | 2002-01-29 | Sepracor, Inc. | Phosphonorisperidone and sulforisperidone compositions and methods |
| ES2197801B1 (es) * | 2002-03-05 | 2005-03-16 | Ferrer Internacional,S.A | Procedimiento de obtencion de la 3-(2-(4-(6-fluoro-benzo(d)isoxazol-3-il) piperidin-1-il)-etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido-(1,2-a ) pirimidin-4-ona. |
| KR20040025224A (ko) * | 2002-09-18 | 2004-03-24 | 주식회사 대웅 | 2-(2-메틸-4-옥소-6,7,8,9-테트라하이드로-4H-피리도[1,2-a]피리미딘-3-일)아세트알데히드 및 그 제조방법 |
| WO2004043923A1 (en) | 2002-11-13 | 2004-05-27 | Synthon B.V. | Process for making risperidone and intermediates therefor |
| US7723518B2 (en) | 2004-09-09 | 2010-05-25 | Janssen Pharmaceutica N.V. | Preparation of 9-hydroxy-3-(2-hydroxyethyl)-2-methyl-4H-pyrido[1,2-A]pyrimidin-4-one |
| US20070197591A1 (en) | 2005-12-12 | 2007-08-23 | Sandra Boom | Use of paliperidone for the treatment of a mental disorder in a psychiatric patient with reduced hepatic function |
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| DK2154138T3 (en) * | 2007-04-19 | 2015-11-02 | Youxin Li | Novel compounds for the treatment of psychotic disorders, methods of preparation and uses thereof |
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| NZ584370A (en) | 2007-10-09 | 2011-04-29 | Cipla Ltd | Processes for the preparation of paliperidone and pharmaceutically acceptable salts thereof and intermediates for use in the processes |
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| BR112013012062B1 (pt) | 2010-11-15 | 2020-06-02 | Agenebio, Inc | Composto derivado da piridazina ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica e uso do composto |
| CN102153552B (zh) * | 2011-03-01 | 2012-08-22 | 吉林大学 | 两种帕潘立酮药物共晶及其制备方法 |
| CN102206210B (zh) * | 2011-04-01 | 2014-07-02 | 常州市第四制药厂有限公司 | 一种6-氟-3-(4-哌啶基)-1,2-苯并异噁唑盐酸盐的生产方法 |
| HK1215170A1 (zh) | 2012-11-14 | 2016-08-19 | The Johns Hopkins University | 治療精神分裂症的方法和組合物 |
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| MA42624A (fr) | 2015-06-19 | 2021-04-28 | Agenebio Inc | Dérivés de benzodiazépine, compositions et méthodes de traitement de la déficience cognitive |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
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|---|---|---|---|---|
| US4342870A (en) * | 1980-03-28 | 1982-08-03 | Janssen Pharmaceutica N.V. | Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives |
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
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1989
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- 1989-10-30 EP EP89202724A patent/EP0368388B1/en not_active Expired - Lifetime
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- 1989-11-06 DK DK551989A patent/DK169923B1/da not_active IP Right Cessation
- 1989-11-06 ZA ZA898436A patent/ZA898436B/xx unknown
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2007
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- 2007-10-15 CY CY200700025C patent/CY2007025I1/el unknown
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- 2007-12-21 NO NO2007017C patent/NO2007017I2/no unknown
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