KR840002377A - 3-(4-피페리딜)-1,2-벤즈이속사졸의 제조방법 - Google Patents
3-(4-피페리딜)-1,2-벤즈이속사졸의 제조방법 Download PDFInfo
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- KR840002377A KR840002377A KR1019820005082A KR820005082A KR840002377A KR 840002377 A KR840002377 A KR 840002377A KR 1019820005082 A KR1019820005082 A KR 1019820005082A KR 820005082 A KR820005082 A KR 820005082A KR 840002377 A KR840002377 A KR 840002377A
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- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- hydrogen
- lower alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims 2
- KEIQPPQTKPFHLZ-UHFFFAOYSA-N 3-piperidin-4-yl-1,2-benzoxazole Chemical compound C1CNCCC1C1=NOC2=CC=CC=C12 KEIQPPQTKPFHLZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- -1 alkenyl halide Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000002923 oximes Chemical class 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- YXTROGRGRSPWKL-UHFFFAOYSA-N 1-benzoylpiperidine Chemical compound C=1C=CC=CC=1C(=O)N1CCCCC1 YXTROGRGRSPWKL-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
Classifications
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- Z가 하이드록시인 다음 일반식(2)의 벤조일 피페리딘을 우선 이의 옥심유도체로 전환시키고, 이 옥심 유도체를 0－아실화하여 다음 일반식(16′)의 0－알카노일옥심으로 한후, 마지막으로 수득한 0－알카노일옥심을 염기로 처리하여 페환하거나, 또는 Z가 할로겐인 다음 일반식(2)의 벤조일 피페리딘을 이의 옥심 유도체로 전환시키고 유리 과정없이 염기의 존재하에서 페환하거나, 또는 유리된 옥심 유도체를 알칼리 수소화물로서 페환하고, 임의로 x 및 m이 다음에 정의하는 바와 같고, R이 그룹 －COR5(여기서 R5는 수소 또는 알킬이다) 또는 벤질옥시카보닐 그룹인 다음 일반식(1)의 화합물을 광산으로 가수분해하여 R이 수소인 다음 일반식(1)의 화합물을 수득하고, 임의로 다음 이란식(1)의 3－(1－알킬－ 도는 벤질－치환된－4－피페리딜)－1,2－벤즈이속사졸을 페닐 할로포르메이트로 처리함으로써 R이 알킬 또는 벤질인 다음 일반식(1)의 화합물을 탈알킬화 또는 탈벤질화하여 다음 일반식(24)의 화합물을 수득하고, 임의로 수득한 이 화합물을 알칼리 수산화물로써 가수분해하여 r이 수소인 다음 일반식(1)의 화합물을 수득하고, 임의로 r이 수소인 다음 일반식(1)의 화합물을 저급알킬할리드, 저급알케닐할리드, 사이클로알킬 저급알킬할리드 또는 디저급알킬 아미노저급알킬 할리드와 반응시켜 r이 저급알킬, 저급알케닐, 사이클로알킬 저급알킬 또는 디저급알킬 아미노저급알킬인 다음 일반식(1)의 상응하는 화합물을 수득하고, 임의로 R이 수소인 다음 일반식(1)의 화합물을 벤조일 퍼옥사이드와 반응시켜 R이 벤조일옥시 그룹인 다음 일반식(1)의 화합물을 수득한 후, 이 화합물을 알칼리 수산화물로써 가수분해하여 R이 하이드록시인 다음 일반식(1)의 화합물을 수득하고, 임의로 R이 수소인 다음 일반식(1)의 화합물을 할로겐화 시안과 반응시켜 R이 시아노인 다음 일반식(1)의 화합물을 수득하거나, 또는 R이 알킬인 다음 일반식(1)의 화합물을 할로겐화시안과 반응시켜 다음 일반식(42)의 화합물을 수득하고 수득한 이 화합물을 상승된 온도에서 전환시켜 R이 시아노인 다음 일반식(1)의 화합물을 수득하고, 임의로 R이 시아노인 다음 일반식(1)의 화합물을 가수분해하여 R이 수소인 다음 일반식(1)의 화합물을 수득하고, 임의로 R이 수소인 다음 일반식(1)의 화합물을 일반식 HalCH2CN(여기서 Hal은 클로로 또는 브로모이다)의 할로아세토니트릴과 반응시켜 R이 시아노메틸인 다음 일반식(1)의 화합물을 수득하고, 임의로 다음 일반식(1)의 화합물의 약학직으로 허용되는 산부가염을 제조함을 특징으로 하는, 다음 일반식(1)의 화합물, 이의 기하 이성체 및 광학적 대장체 또는 이의 약학직으로 허용되는 산부가염의 제조방법.상기 일반식(1)에서 R은 수소, 저급알킬, 저급알케닐, 사이클로알킬저급알킬, 페닐저급알킬, 하이드록시, 디저급알킬아미노저급알킬, 시아노, 시아노메틸,또는 일반식의 그룹이고, R1은 수소, 저급알킬 또는 일반식 OR2의 그룹이며, R2는 페닐 또는 벤질이고, X는 저급알킬, 저급알콕시, 할로겐 또는 하이드록시이며, m은 0, 1 또는 2이다.상기 일반식(2)에서 R은 그룹 COR5(단 R5는 수소 또는 알킬이다) 또는 저급알킬, 저급알케닐, 사이클로알킬 저급알킬, 페닐저급알킬, 벤질 또는 벤질옥시카보닐 그룹이고, Z는 할로겐 또는 하이드록시이며, x 및 m은 전술한 바와 같다.상기 일반식(16′)에서 R, Z, X 및 m은 전술한 바와 같고, R6은 알킬이다.상기 일반식(24)에서 x 및 m은 전술한 바와 같다.상기 일반식(42)에서 x 및 m은 전술한 바와 같고, R13은 알킬이며, Hal은 할로겐이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019880011283A KR880002592B1 (ko) | 1981-11-10 | 1988-09-01 | 벤조일 피페리딘 |
| KR1019880011284A KR880002593B1 (ko) | 1981-11-12 | 1988-09-01 | 벤조일 피페리딘 옥심 및 이의 0-유도체 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/319,871 US4355037A (en) | 1981-11-12 | 1981-11-12 | 3-(4-Piperidyl)-1,2-benzisoxales |
| US319871 | 2002-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002377A true KR840002377A (ko) | 1984-06-25 |
| KR880002012B1 KR880002012B1 (ko) | 1988-10-12 |
Family
ID=23243957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205082A KR880002012B1 (ko) | 1981-11-10 | 1982-11-10 | 3-(4-피페리딜)-1,2-벤즈 이속사졸 및 이의 제조방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4355037A (ko) |
| EP (1) | EP0080104B1 (ko) |
| JP (1) | JPS5890582A (ko) |
| KR (1) | KR880002012B1 (ko) |
| AT (1) | ATE39251T1 (ko) |
| AU (2) | AU567865B2 (ko) |
| CA (1) | CA1215066A (ko) |
| DE (1) | DE3279282D1 (ko) |
| ES (3) | ES517245A0 (ko) |
| IE (1) | IE54857B1 (ko) |
| ZA (1) | ZA828281B (ko) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5835177A (ja) * | 1981-08-26 | 1983-03-01 | Dainippon Pharmaceut Co Ltd | ２−環状アミノ−２−（１，２−ベンズイソキサゾ−ル−３−イル）酢酸エステル類並びにその酸付加塩類および第４級アンモニウム塩類 |
| US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
| US4408054A (en) * | 1981-11-12 | 1983-10-04 | Hoechst-Roussel Pharmaceuticals Inc. | Oximes of 4-benzoyl-piperidines |
| US4528376A (en) * | 1982-08-11 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(4-Piperidyl)-1,2-benzisoxazoles |
| US4458076A (en) * | 1983-05-31 | 1984-07-03 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
| US4528292A (en) * | 1984-04-23 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | Antihypertensive 1,2-benzisothiazole piperidines |
| US4590196A (en) * | 1984-08-23 | 1986-05-20 | Bristol-Myers Company | Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives |
| EP0192935B1 (en) * | 1985-01-23 | 1991-02-27 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-(piperidinyl)-1h-indazoles a process for their preparation and their use as medicaments |
| US5057611A (en) * | 1985-04-22 | 1991-10-15 | Hoechst-Roussel Pharmaceuticals Inc. | Benzoylpiperidines |
| EP0243184A3 (en) * | 1986-04-25 | 1989-05-10 | Roussel-Uclaf | Pesticidal compounds |
| JPS63185141A (ja) * | 1987-01-27 | 1988-07-30 | Daikin Ind Ltd | 空気調和機のデ−タ伝送方式 |
| CA1335289C (en) * | 1987-10-26 | 1995-04-18 | Fujio Antoku | Piperidinyl benzisoxazole derivatives, their production and pharmaceutical use |
| GR1000667B (el) * | 1988-03-21 | 1992-09-25 | Janssen Pharmaceutica Nv | Μεθοδος παρασκευης 3-πιπεριδινυλο-1,2-βενζισοξαζολων. |
| FR2641278B1 (fr) * | 1989-01-05 | 1991-03-22 | Lipha | Piperidines, procedes de preparation et medicaments les contenant |
| DE69021645T2 (de) * | 1989-05-19 | 1996-02-22 | Hoechst-Roussel Pharmaceuticals Inc., Somerville, N.J. | N-(aryloxyalkyl)heteroarylpiperidine und -heteroarylpiperazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente. |
| US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
| US5364866A (en) | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| FR2654104B1 (fr) * | 1989-11-07 | 1992-01-03 | Adir | Nouveaux derives du 1,2-benzisoxazole, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| NZ236501A (en) * | 1989-12-21 | 1992-12-23 | Merrell Dow Pharma | Piperidine derivatives and antithrombotic compositions |
| FR2671350A1 (fr) * | 1991-01-08 | 1992-07-10 | Adir | Nouveaux derives de benzisoxazole et de benzisothiazole, leur procede de preparation, et les compositions pharmaceutiques les renfermant. |
| JP2800953B2 (ja) * | 1990-07-06 | 1998-09-21 | 住友製薬株式会社 | 新規なイミド誘導体 |
| US5055476A (en) * | 1990-08-13 | 1991-10-08 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-(1,2-benzisoxazol-3-yl)-4-pyridinamines and derivatives |
| US7253165B2 (en) * | 1999-09-14 | 2007-08-07 | Aventis Pharmaceuticals Inc. | Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists |
| 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 |
| WO2001085731A1 (en) | 2000-05-05 | 2001-11-15 | Rpg Life Sciences Limited | A PROCESS FOR THE PREPARATION OF ANTI-PSCHOTIC 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2,-a]pyrimidin-4-one |
| CN111518019B (zh) * | 2019-02-01 | 2023-10-24 | 江苏豪森药业集团有限公司 | 一种棕榈酸帕里哌酮中间体的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2517695A (en) * | 1945-07-13 | 1950-08-08 | Ciba Pharm Prod Inc | Production of 1-alkyl 4-phenylpiperidyl 4-ketones |
| JPS5545545B2 (ko) * | 1972-03-17 | 1980-11-18 | ||
| DE2245971A1 (de) * | 1972-07-13 | 1974-03-14 | Merck Patent Gmbh | Isoxazolderivate und verfahren zu ihrer herstellung |
| US4217349A (en) * | 1974-07-01 | 1980-08-12 | Sumitomo Chemical Company, Limited | Benzisoxazole derivatives |
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| 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 |
| US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
| US4352811A (en) * | 1981-11-12 | 1982-10-05 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles |
-
1981
- 1981-11-12 US US06/319,871 patent/US4355037A/en not_active Expired - Lifetime
-
1982
- 1982-11-09 AT AT82110318T patent/ATE39251T1/de not_active IP Right Cessation
- 1982-11-09 EP EP82110318A patent/EP0080104B1/en not_active Expired
- 1982-11-09 DE DE8282110318T patent/DE3279282D1/de not_active Expired
- 1982-11-10 ES ES517245A patent/ES517245A0/es active Granted
- 1982-11-10 CA CA000415352A patent/CA1215066A/en not_active Expired
- 1982-11-10 KR KR8205082A patent/KR880002012B1/ko active
- 1982-11-11 JP JP57196885A patent/JPS5890582A/ja active Granted
- 1982-11-11 ZA ZA828281A patent/ZA828281B/xx unknown
- 1982-11-11 AU AU90390/82A patent/AU567865B2/en not_active Ceased
- 1982-11-11 IE IE2684/82A patent/IE54857B1/en not_active IP Right Cessation
-
1984
- 1984-02-01 ES ES529370A patent/ES8507519A1/es not_active Expired
- 1984-02-01 ES ES529369A patent/ES529369A0/es active Granted
-
1988
- 1988-02-08 AU AU11385/88A patent/AU612621B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU1138588A (en) | 1988-05-19 |
| ZA828281B (en) | 1983-09-28 |
| ES529370A0 (es) | 1985-09-01 |
| ES8507519A1 (es) | 1985-09-01 |
| DE3279282D1 (en) | 1989-01-19 |
| ATE39251T1 (de) | 1988-12-15 |
| AU612621B2 (en) | 1991-07-18 |
| AU567865B2 (en) | 1987-12-10 |
| EP0080104A2 (en) | 1983-06-01 |
| CA1215066A (en) | 1986-12-09 |
| EP0080104A3 (en) | 1983-08-24 |
| ES8601193A1 (es) | 1985-09-16 |
| US4355037A (en) | 1982-10-19 |
| IE54857B1 (en) | 1990-02-28 |
| JPH0411546B2 (ko) | 1992-02-28 |
| JPS5890582A (ja) | 1983-05-30 |
| EP0080104B1 (en) | 1988-12-14 |
| ES529369A0 (es) | 1985-09-16 |
| ES8405791A1 (es) | 1984-06-16 |
| ES517245A0 (es) | 1984-06-16 |
| KR880002012B1 (ko) | 1988-10-12 |
| IE822684L (en) | 1983-05-12 |
| AU9039082A (en) | 1983-05-19 |
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