AU2696797A - Piperidines and pyrrolidines - Google Patents

Piperidines and pyrrolidines

Info

Publication number: AU2696797A
Authority: AU; Australia
Prior art keywords: formula; ethyl; pyridyl; pyrrolidin; piperidin
Prior art date: 1996-04-18
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.): Abandoned

Application number

AU26967/97A

Other languages

English (en)

Inventor

Gerd Bartoszyk

Ronny Andersson Bengt

Henning Dr. Bottcher

Ralf Dr. Devant

Hartmut Greiner

Lars Olov Hansson

Jurgen Harting

Joachim Marz

Christoph Seyfried

Clas Ake Sonesson

Nils Peter Stjernlof

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date 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 date listed.)

1996-04-18

Filing date

1997-04-14

Publication date

1997-11-12

1997-04-14 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

1997-11-12 Publication of AU2696797A publication Critical patent/AU2696797A/en

Status Abandoned legal-status Critical Current

Links

150000003053 piperidines Chemical class 0.000 title description 2
150000003235 pyrrolidines Chemical class 0.000 title description 2
-1 3-indolyl Chemical group 0.000 claims description 144
150000001875 compounds Chemical class 0.000 claims description 135
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 27
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
230000002401 inhibitory effect Effects 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 8
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
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 description 6
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CFYYLUBNRPWHPL-UHFFFAOYSA-N 1-[2-[4-(6-fluoro-1h-indol-3-yl)piperidin-1-yl]ethyl]-3-(3-fluorophenyl)-1-pyridin-2-ylurea Chemical compound FC1=CC=CC(NC(=O)N(CCN2CCC(CC2)C=2C3=CC=C(F)C=C3NC=2)C=2N=CC=CC=2)=C1 CFYYLUBNRPWHPL-UHFFFAOYSA-N 0.000 claims description 3
ZYJUVOVVLLVZIS-UHFFFAOYSA-N 3-cyclohexyl-1-[2-[3-(6-fluoro-1H-indol-3-yl)piperidin-1-yl]ethyl]-1-pyridin-2-ylurea Chemical compound C1(CCCCC1)NC(=O)N(C1=NC=CC=C1)CCN1CC(CCC1)C1=CNC2=CC(=CC=C12)F ZYJUVOVVLLVZIS-UHFFFAOYSA-N 0.000 claims description 3
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ATWPRNREQOFDAP-UHFFFAOYSA-N n-[2-[3-(2-methoxyphenyl)pyrrolidin-1-yl]ethyl]-n-pyridin-2-ylcyclohexanecarboxamide Chemical compound COC1=CC=CC=C1C1CN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 ATWPRNREQOFDAP-UHFFFAOYSA-N 0.000 claims description 2
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238000006243 chemical reaction Methods 0.000 description 39
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
235000019439 ethyl acetate Nutrition 0.000 description 16
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
239000000126 substance Substances 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
239000003480 eluent Substances 0.000 description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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150000007513 acids Chemical class 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
238000000926 separation method Methods 0.000 description 7
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
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125000003277 amino group Chemical group 0.000 description 5
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HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
BSFPEVZAUTXHRI-UHFFFAOYSA-N 3-fluoro-n-[2-(4-naphthalen-1-ylpiperidin-1-yl)ethyl]aniline Chemical compound FC1=CC=CC(NCCN2CCC(CC2)C=2C3=CC=CC=C3C=CC=2)=C1 BSFPEVZAUTXHRI-UHFFFAOYSA-N 0.000 description 4
ZWQBLJKCRPTUSP-UHFFFAOYSA-N 5-fluoro-3-pyrrolidin-3-yl-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1C1CCNC1 ZWQBLJKCRPTUSP-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
- 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
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)

AU26967/97A 1996-04-18 1997-04-14 Piperidines and pyrrolidines Abandoned AU2696797A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19615232		1996-04-18
DE19615232A DE19615232A1 (de)	1996-04-18	1996-04-18	Neue Carbamoylderivate und deren Verwendung als 5-HT ¶1¶¶A¶-Antagonisten
PCT/EP1997/001853 WO1997040038A1 (en)	1996-04-18	1997-04-14	Piperidines and pyrrolidines

Publications (1)

Publication Number	Publication Date
AU2696797A true AU2696797A (en)	1997-11-12

Family

ID=7791576

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU26967/97A Abandoned AU2696797A (en)	1996-04-18	1997-04-14	Piperidines and pyrrolidines

Country Status (15)

Country	Link
EP (1)	EP0898569A1 (pt)
JP (1)	JP2000508670A (pt)
KR (1)	KR20000005505A (pt)
AR (1)	AR006690A1 (pt)
AU (1)	AU2696797A (pt)
BR (1)	BR9708677A (pt)
CA (1)	CA2252385A1 (pt)
CZ (1)	CZ330598A3 (pt)
DE (1)	DE19615232A1 (pt)
HU (1)	HUP9901389A3 (pt)
NO (1)	NO984861D0 (pt)
PL (1)	PL329351A1 (pt)
SK (1)	SK141998A3 (pt)
WO (1)	WO1997040038A1 (pt)
ZA (1)	ZA973301B (pt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19756036A1 (de) *	1997-12-17	1999-06-24	Merck Patent Gmbh	Amid- und Harnstoffderivate
ES2188155T3 (es) *	1998-04-08	2003-06-16	Wyeth Corp	N-ariloxietilindolilalquilaminas para el tratamiento de la depresion.
US6150533A (en) *	1998-04-08	2000-11-21	American Home Products Corp.	N-aryloxyethyl-indoly-alkylamines for the treatment of depression
EP1076658A1 (en) *	1998-04-29	2001-02-21	American Home Products Corporation	Serotonergic agents
US6376494B1 (en)	1998-06-15	2002-04-23	American Home Products Corporation	Cycloalkyl-substituted aryl-piperazines, piperidines and tetrahydropyridines as serotonergic agents
CN1312802A (zh) *	1998-06-15	2001-09-12	美国家用产品公司	作为5－羟色胺能药物的环烷基取代的芳基哌嗪、哌啶和四氢吡啶
US6239126B1 (en)	1998-12-17	2001-05-29	American Home Products Corporation	Arylpiperidine and aryl-1,2,5,6-tetra-hydropyridine urea derivatives
JP2002532472A (ja) *	1998-12-17	2002-10-02	アメリカン・ホーム・プロダクツ・コーポレイション	５−ｈｔ１ａ受容体活性を有するアリールピペリジンおよびアリール−１，２，５，６−テトラヒドロピリジン尿素誘導体
ATE294780T1 (de) *	1998-12-17	2005-05-15	Wyeth Corp	Arylpiperidin- und aryl-1,2,5,6- tetrahydropyridinamid-derivate mit 5ht1a rezeptor aktivität
US6326381B1 (en)	1998-12-17	2001-12-04	American Home Products Corporation	Arylpiperidine and aryl-1,2,5,6-tetrahydropyidine amide derivates
JP2002535365A (ja) *	1999-01-28	2002-10-22	ブリストル−マイヤーズスクイブカンパニー	抗うつ性複素環化合物
WO2002051987A1 (de) *	2000-12-27	2002-07-04	Axiogenesis Ag	System zur zell-und entwicklungsspezifischen selektion differenzierender embryonaler stammzellen; adulter stammzellen und embryonaler keinbahnzellen
KR100459917B1 (ko) *	2001-12-14	2004-12-03	(주)바이오뉴트리젠	페놀릭산 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물
DE10337184A1 (de) *	2003-08-13	2005-03-10	Gruenenthal Gmbh	Substituierte 3-Pyrrolidin-Indol-Derivate
UY36390A (es) *	2014-11-05	2016-06-01	Flexus Biosciences Inc	Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen
MX2017005462A (es)	2014-11-05	2017-07-28	Flexus Biosciences Inc	Agentes inmunorreguladores.
CA3220850A1 (en) *	2021-06-02	2022-12-08	Jason WALLACH	Fluorinated tryptamine compounds, analogues thereof, and methods using same
EP4469453A1 (en)	2022-01-29	2024-12-04	Suven Life Sciences Limited	Benzoisothiazole and benzoisoxazole compounds for the treatment of mental disorders

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3226392A (en) *	1960-03-07	1965-12-28	Sterling Drug Inc	1-[n-aryl-n-acylaminoalkyl]-4-aryl-1,2,3,6-tetrahydropyridines, the corresponding piperidines and their salts
US3635982A (en) *	1969-04-08	1972-01-18	American Home Prod	Amino-substituted-quinoxalinyloxazolidines and -oxazines
US4782071A (en) *	1986-11-03	1988-11-01	Warner-Lambert Company	Tetrasubstituted urea cholinergic agents
AU645681B2 (en) *	1991-05-02	1994-01-20	John Wyeth & Brother Limited	Piperazine derivatives
FR2706894A1 (en) *	1993-06-22	1994-12-30	Synthelabo	N-Phenyl-N-(piperidinoalkyl)arylamide derivatives, their preparation and their application in therapeutics
GB9314758D0 (en) *	1993-07-16	1993-08-25	Wyeth John & Brother Ltd	Heterocyclic derivatives
EP0661266A1 (en) *	1993-12-27	1995-07-05	Toa Eiyo Ltd.	Substituted cyclic amine compounds as 5HT2 antagonists
GB9411099D0 (en) *	1994-06-03	1994-07-27	Wyeth John & Brother Ltd	Piperazine derivatives

1996
- 1996-04-18 DE DE19615232A patent/DE19615232A1/de not_active Withdrawn
1997
- 1997-04-14 EP EP97920673A patent/EP0898569A1/en not_active Withdrawn
- 1997-04-14 KR KR1019980708295A patent/KR20000005505A/ko not_active Withdrawn
- 1997-04-14 AU AU26967/97A patent/AU2696797A/en not_active Abandoned
- 1997-04-14 SK SK1419-98A patent/SK141998A3/sk unknown
- 1997-04-14 BR BR9708677A patent/BR9708677A/pt not_active Application Discontinuation
- 1997-04-14 PL PL97329351A patent/PL329351A1/xx unknown
- 1997-04-14 JP JP9537685A patent/JP2000508670A/ja active Pending
- 1997-04-14 CZ CZ983305A patent/CZ330598A3/cs unknown
- 1997-04-14 WO PCT/EP1997/001853 patent/WO1997040038A1/en not_active Ceased
- 1997-04-14 HU HU9901389A patent/HUP9901389A3/hu unknown
- 1997-04-14 CA CA002252385A patent/CA2252385A1/en not_active Abandoned
- 1997-04-17 ZA ZA9703301A patent/ZA973301B/xx unknown
- 1997-04-18 AR ARP970101562A patent/AR006690A1/es unknown
1998
- 1998-10-16 NO NO984861A patent/NO984861D0/no unknown

Also Published As

Publication number	Publication date
ZA973301B (en)	1997-10-24
CA2252385A1 (en)	1997-10-30
AR006690A1 (es)	1999-09-08
NO984861L (no)	1998-10-16
CZ330598A3 (cs)	1999-01-13
DE19615232A1 (de)	1997-10-23
NO984861D0 (no)	1998-10-16
SK141998A3 (en)	1999-03-12
BR9708677A (pt)	1999-08-03
EP0898569A1 (en)	1999-03-03
KR20000005505A (ko)	2000-01-25
HUP9901389A2 (hu)	1999-08-30
HUP9901389A3 (en)	2000-09-28
JP2000508670A (ja)	2000-07-11
PL329351A1 (en)	1999-03-29
WO1997040038A1 (en)	1997-10-30

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AU2696797A (en)	1997-11-12	Piperidines and pyrrolidines
US6037352A (en)	2000-03-14	Muscarinic antagonists
US8889702B2 (en)	2014-11-18	Derivatives of azaspiranyl-alkylcarbamates of 5-member heterocyclic compounds, preparation thereof and therapeutic use thereof
TR201802550T4 (tr)	2018-03-21	Lökotrien üretiminin benzodioksan inhibitörleri.
RS20060318A (sr)	2008-11-28	Derivati n-/fenil(alkil-piperidin-2-il)metil/benzamida postupak za njihovo dobijanje i njihova terapeutska primena
CZ20031082A3 (cs)	2004-08-18	Derivát piperidinuŹ způsob jeho přípravyŹ jeho použití a farmaceutický prostředekŹ který ho obsahuje
SK50895A3 (en)	1995-11-08	3-indolylpiperidine derivative, method of its preparation, its use for preparation of pharmaceutical composition and pharmaceutical composition containing them
CN1146559C (zh)	2004-04-21	毒蕈碱性拮抗剂
CN117999265A (zh)	2024-05-07	取代的融合双环大环化合物及其相关治疗方法
EP0711291B1 (en)	1998-11-25	N-(piperidinyl-1-alkyl)-substituted cyclohexane carboxylic acid amides as 5-ht1a receptor antagonists
US6462056B1 (en)	2002-10-08	Oxazolidines as 5-HT2A-antagonists
US20070232657A1 (en)	2007-10-04	Novel compounds
AU2009315448A1 (en)	2010-05-20	Carbamate derivatives of alkyl-heterocycles, preparation thereof and therapeutic use thereof
AU715785B2 (en)	2000-02-10	1-(pyrazol-3-ylethyl)-4-(indol-3-yl) piperdines as compositions affecting the central nervous system
NO326514B1 (no)	2008-12-22	Nye heteroarylderivater, deres fremstilling og anvendelse
KR100591640B1 (ko)	2006-06-20	4-[1-히드록시-1-(2,3-디메톡시페닐)메틸]피페리딘의 제조방법
RU2175970C2 (ru)	2001-11-20	Производные пиперидинилметилоксазолидин-2-она, способ их получения и фармацевтическая композиция на их основе
HUP0003997A2 (en)	2001-03-28	3-benzylpiperidine derivatives, pharmaceutical compositions containing them and process for producing them
JP2005104896A (ja)	2005-04-21	２−アルコキシ−６−アミノ−５−ハロゲノピリジン−３−カルボキサミド誘導体およびそれを含有する医薬組成物
CZ2002499A3 (cs)	2002-05-15	Derivát piperidinalkoholu, způsob jeho přípravy, jeho pouľití a farmaceutický prostředek, který ho obsahuje
MXPA98008594A (en)	1999-05-31	Piperidines and pyrolrolidi

Legal Events

Date	Code	Title	Description
2000-12-21	MK5	Application lapsed section 142(2)(e) - patent request and compl. specification not accepted