FI107918B - Menetelmä terapeuttisesti aktiivisten trisyklisten 1-aminoalkyylipyrrolijohdannaisten valmistamiseksi - Google Patents

Menetelmä terapeuttisesti aktiivisten trisyklisten 1-aminoalkyylipyrrolijohdannaisten valmistamiseksi Download PDF

Info

Publication number: FI107918B
Authority: FI; Finland
Prior art keywords: mmol; solution; mixture; hours; anhydrous
Prior art date: 1993-10-22

Application number

FI944970A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI944970A0 (fi

FI944970A7 (fi

Inventor

Juergen Wichmann

Ulrich Widmer

Michael Boes

Original Assignee

Hoffmann La Roche

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.)

1993-10-22

Filing date

1994-10-21

Publication date

2001-10-31

1994-10-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1994-10-21 Publication of FI944970A0 publication Critical patent/FI944970A0/fi

1995-04-23 Publication of FI944970A7 publication Critical patent/FI944970A7/fi

2001-10-31 Application granted granted Critical

2001-10-31 Publication of FI107918B publication Critical patent/FI107918B/fi

Links

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238000002360 preparation method Methods 0.000 title claims description 15
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239000002253 acid Substances 0.000 claims abstract description 22
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239000001257 hydrogen Substances 0.000 claims abstract description 12
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
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150000002431 hydrogen Chemical class 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
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150000007514 bases Chemical class 0.000 claims abstract description 3
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125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 47
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000011282 treatment Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Anesthesiology (AREA)
Diabetes (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)
Indole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Organic Insulating Materials (AREA)
Materials For Medical Uses (AREA)

FI944970A 1993-10-22 1994-10-21 Menetelmä terapeuttisesti aktiivisten trisyklisten 1-aminoalkyylipyrrolijohdannaisten valmistamiseksi FI107918B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH320293		1993-10-22
CH320293		1993-10-22
CH252994		1994-08-17
CH252994		1994-08-17

Publications (3)

Publication Number	Publication Date
FI944970A0 FI944970A0 (fi)	1994-10-21
FI944970A7 FI944970A7 (fi)	1995-04-23
FI107918B true FI107918B (fi)	2001-10-31

Family

ID=25690677

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI944970A FI107918B (fi)	1993-10-22	1994-10-21	Menetelmä terapeuttisesti aktiivisten trisyklisten 1-aminoalkyylipyrrolijohdannaisten valmistamiseksi

Country Status (20)

Country	Link
US (1)	US5646173A (fr)
EP (1)	EP0657426B1 (fr)
JP (1)	JP2638751B2 (fr)
KR (1)	KR100348029B1 (fr)
CN (1)	CN1057083C (fr)
AT (1)	ATE168675T1 (fr)
AU (1)	AU680543B2 (fr)
CA (1)	CA2132887C (fr)
CZ (1)	CZ260394A3 (fr)
DE (1)	DE59406489D1 (fr)
DK (1)	DK0657426T3 (fr)
ES (1)	ES2120551T3 (fr)
FI (1)	FI107918B (fr)
HU (1)	HU217840B (fr)
IL (1)	IL111315A (fr)
NO (1)	NO301637B1 (fr)
NZ (1)	NZ264711A (fr)
RU (1)	RU2128649C1 (fr)
TW (1)	TW334423B (fr)
UA (1)	UA41316C2 (fr)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9518572D0 (en) *	1995-09-12	1995-11-15	Smithkline Beecham Plc	Compounds
AU727654B2 (en) *	1997-06-13	2000-12-21	Yamanouchi Pharmaceutical Co., Ltd.	Tricyclic pyrazole derivative
US6960579B1 (en)	1998-05-19	2005-11-01	Alcon Manufacturing, Ltd.	Serotonergic 5HT7 receptor compounds for treating ocular and CNS disorders
GB9819019D0 (en) *	1998-09-01	1998-10-28	Cerebrus Ltd	Chemical compounds II
US6326379B1 (en)	1998-09-16	2001-12-04	Bristol-Myers Squibb Co.	Fused pyridine inhibitors of cGMP phosphodiesterase
ATE310566T1 (de)	1998-09-18	2005-12-15	Alcon Mfg Ltd	5ht2-agoniste zur behandlung des glaukoms
GB9902047D0 (en)	1999-01-29	1999-03-17	Cerebrus Ltd	Chemical compounds XI
US6465467B1 (en)	1999-05-21	2002-10-15	Biovitrum Ab	Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
GB9918965D0 (en) *	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxi
GB9918962D0 (en) *	1999-08-11	1999-10-13	Cerebrus Ltd	Chemical compounds xxii
EP1132389A1 (fr)	2000-03-06	2001-09-12	Vernalis Research Limited	Nouveaux dérivés de l'azaindole pour le traitement de l'obésité
US7012090B1 (en)	2000-03-17	2006-03-14	Alcon, Inc.	Pyranoindoles for treating glaucoma
JP2004538240A (ja) *	2000-03-31	2004-12-24	パーデュー・リサーチ・ファウンデーション	ホスホラミデートおよびそのための方法
AU2167002A (en) *	2000-10-16	2002-06-11	Hoffmann La Roche	Indoline derivatives and their use as 5-ht2 receptor ligands
NZ525699A (en)	2000-11-20	2005-03-24	Biovitrum Ab	Piperazinylpyrazines compounds as antagonists of serotonin 5-HT2 receptor
SE0004245D0 (sv)	2000-11-20	2000-11-20	Pharmacia Ab	Novel compounds and their use
WO2004098807A1 (fr) *	2000-11-21	2004-11-18	Barsplice Products, Inc.	Procede de fabrication de coupleurs en acier permettant d'assembler des barres d'armature du beton
KR100539143B1 (ko)	2000-12-27	2005-12-26	에프. 호프만-라 로슈 아게	인돌 유도체 및 그의 5-ｈｔ2ｂ 및 5-ｈｔ2ｃ 수용체리간드로서의 용도
EP1392658A4 (fr) *	2001-06-01	2004-10-13	Alcon Inc	Indazoles et indoles nouveaux fusionnes et leur utilisation dans le traitement de glaucomes
EP1392292B1 (fr) *	2001-06-01	2006-03-01	Alcon, Inc.	Pyranoindazoles et leur utilisation dans le traitement du glaucome
US6884816B2 (en)	2001-08-31	2005-04-26	Alcon, Inc.	Hydroxy substituted fused naphthyl-azoles and fused indeno-azoles and their use for the treatment of glaucoma
TW593302B (en) *	2001-12-20	2004-06-21	Alcon Inc	Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma
JP4460450B2 (ja)	2002-06-19	2010-05-12	ビオヴィトルム・アクチボラゲット（プブリクト）	新規化合物、その使用および製造法
PL375564A1 (en) *	2002-08-30	2005-11-28	Alcon, Inc.	Substituted 5-chroman-5-yl-ethylamine compounds and their use for the treatment of glaucoma
CA2506204A1 (fr) *	2002-12-13	2004-07-01	Alcon, Inc.	Nouveaux analogues de benzopyranne et leur utilisation pour le traitement du glaucome
CL2004000826A1 (es)	2003-04-25	2005-03-04	Pfizer	Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129
WO2004103960A2 (fr)	2003-05-16	2004-12-02	Ambit Biosciences Corporation	Composes et utilisations de ces derniers
JP2007501866A (ja) *	2003-06-13	2007-02-01	マイクロバイアインコーポレイテッド	胃腸疾患の治療のための方法および組成物
GB0314967D0 (en)	2003-06-26	2003-07-30	Hoffmann La Roche	Piperazine derivatives
US7476687B2 (en) *	2003-11-26	2009-01-13	Alcon, Inc.	Substituted furo[2,3-g]indazoles for the treatment of glaucoma
WO2005058911A2 (fr) *	2003-12-15	2005-06-30	Alcon, Inc.	[1,4]oxazino[2,3-g]indazoles substitues pour traiter le glaucome
US7338972B1 (en)	2003-12-15	2008-03-04	Alcon, Inc.	Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma
US7129257B1 (en)	2003-12-15	2006-10-31	Alcon, Inc.	Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma
US20050182044A1 (en) *	2004-02-17	2005-08-18	Bruinsma Gosse B.	Combinatorial therapy with an acetylcholinesterase inhibitor and (3aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3,-b]indol-5-yl phenylcarbamate
CA2508585A1 (fr) *	2004-06-01	2005-12-01	Axonyx, Inc.	Dispositif d'administration transdermique pour le traitement des troubles cognitifs
JP2005350471A (ja) *	2004-06-08	2005-12-22	Axonyx Inc	β−アミロイド前駆体タンパク質阻害剤およびＨＭＧＣｏＡ還元酵素阻害剤を使用するアルツハイマー病の進行を遅延させる方法
KR101257233B1 (ko) *	2004-07-29	2013-04-29	아더시스 인코포레이티드	세로토닌 수용체 조절제로서의 트리사이클릭 인데노-피롤유도체
JP5173190B2 (ja)	2004-08-25	2013-03-27	武田薬品工業株式会社	腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法
US20060073172A1 (en) *	2004-10-01	2006-04-06	Schneider L W	Stabilized ophthalmic solution for the treatment of glaucoma and lowering intraocular pressure
WO2006062839A1 (fr) *	2004-12-08	2006-06-15	Alcon, Inc.	Utilisation de dioxindoindazoles et de dioxoloindazoles pour traiter le glaucome
BRPI0609268A2 (pt)	2005-03-31	2010-03-09	Pfizer Prod Inc	derivados de ciclopentapiridina e tetraidroquinolina
TW200744567A (en) *	2005-09-23	2007-12-16	Alcon Inc	Phenylethylamine analogs and their use for treating glaucoma
EP2727585A1 (fr)	2006-05-16	2014-05-07	Takeda Pharmaceutical Company Limited	Méthode de dépistage in-vivo
US20070293475A1 (en) *	2006-06-20	2007-12-20	Alcon Manufacturing Ltd.	Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma
ATE496894T1 (de) *	2006-07-14	2011-02-15	Pfizer Prod Inc	Tartratsalz von (7s)-7-ä(5-fluor-2-
JP5140080B2 (ja) *	2006-09-21	2013-02-06	ラクオリア創薬株式会社	選択的アシッドポンプ阻害剤としてのベンゾイミダゾール誘導体
EP2789338A3 (fr)	2007-11-15	2015-01-14	Takeda Pharmaceutical Company Limited	Dérivé de pyridine condensé et son utilisation
KR101062376B1 (ko)	2008-04-10	2011-09-06	한국화학연구원	신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물
SG10201510665WA (en)	2009-12-04	2016-01-28	Sunovion Pharmaceuticals Inc	Multicycle Compounds And Pharmaceutical Compositions Useful For The Treatment Of Neurological Disorders
EP2510949A4 (fr)	2009-12-11	2013-11-13	Astellas Pharma Inc	Agent thérapeutique pour la fibromyalgie
KR102205400B1 (ko) *	2014-02-14	2021-01-21	삼성디스플레이 주식회사	인덴계 화합물 및 이를 포함한 유기 발광 소자
PT3494119T (pt)	2016-07-29	2024-12-10	Pgi Drug Discovery Llc	Compostos e composições e seus usos
MA45795A (fr)	2016-07-29	2019-06-05	Sunovion Pharmaceuticals Inc	Composés et compositions, et utilisations associées
MX390141B (es)	2017-02-16	2025-03-20	Sunovion Pharmaceuticals Inc	Metodos para tratar esquizofrenia
CA3070993C (fr)	2017-08-02	2025-05-20	Sunovion Pharmaceuticals Inc.	Composés d’isochromane et leurs utilisations
US20210052600A1 (en)	2017-12-27	2021-02-25	Takeda Pharmaceutical Company Limited	Therapeutic agents for stress urinary incontinence and incotinence of feces
UA130249C2 (uk)	2018-02-16	2025-12-31	Сумітомо Фарма Америка, Інк.	Солі, кристалічні форми і способи їх отримання
EP3938045A1 (fr)	2019-03-14	2022-01-19	Sunovion Pharmaceuticals Inc.	Sels d'un composé d'isochromanyle et formes cristallines, procédés de préparation, utilisations thérapeutiques et compositions pharmaceutiques associées
CA3180115A1 (fr)	2020-04-14	2021-10-21	Sunovion Pharmaceuticals Inc.	(s)-(4,5-dihydro-7 h-thieno[2,3-c]pyran-7-yl)-n-methylmethanamine pour le traitement de troubles neurologiques et psychiatriques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU463261A3 (ru) *	1970-02-20	1975-03-05	Империал Кемикал Индастриз Лимитед (Фирма)	Способ получени производных алканоламина
US3997557A (en) *	1974-04-23	1976-12-14	American Hoechst Corporation	Substituted N-aminoalkylpyrroles
US5244888A (en) *	1989-11-17	1993-09-14	Abbott Laboratories	5-HT selective agents
TW224974B (fr) *	1991-07-02	1994-06-11	Hoffmann La Roche
EP0638071B1 (fr) *	1992-12-28	1997-04-09	Eisai Co., Ltd.	Derives d'acide carbonique heterocyclique se fixant sur des recepteurs des retinoides

1994
- 1994-09-07 TW TW083108266A patent/TW334423B/zh active
- 1994-09-21 CA CA002132887A patent/CA2132887C/fr not_active Expired - Fee Related
- 1994-10-07 DK DK94115812T patent/DK0657426T3/da active
- 1994-10-07 DE DE59406489T patent/DE59406489D1/de not_active Expired - Fee Related
- 1994-10-07 ES ES94115812T patent/ES2120551T3/es not_active Expired - Lifetime
- 1994-10-07 EP EP94115812A patent/EP0657426B1/fr not_active Expired - Lifetime
- 1994-10-07 AT AT94115812T patent/ATE168675T1/de not_active IP Right Cessation
- 1994-10-14 AU AU75838/94A patent/AU680543B2/en not_active Ceased
- 1994-10-17 HU HU9402985A patent/HU217840B/hu not_active IP Right Cessation
- 1994-10-17 NZ NZ264711A patent/NZ264711A/en unknown
- 1994-10-17 IL IL11131594A patent/IL111315A/xx not_active IP Right Cessation
- 1994-10-20 RU RU94037968/04A patent/RU2128649C1/ru not_active IP Right Cessation
- 1994-10-20 CN CN94117150A patent/CN1057083C/zh not_active Expired - Fee Related
- 1994-10-21 UA UA94105955A patent/UA41316C2/uk unknown
- 1994-10-21 FI FI944970A patent/FI107918B/fi not_active IP Right Cessation
- 1994-10-21 CZ CZ942603A patent/CZ260394A3/cs unknown
- 1994-10-21 NO NO944000A patent/NO301637B1/no unknown
- 1994-10-21 KR KR1019940026931A patent/KR100348029B1/ko not_active Expired - Fee Related
- 1994-10-24 JP JP6257774A patent/JP2638751B2/ja not_active Expired - Fee Related
1996
- 1996-02-21 US US08/594,533 patent/US5646173A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO944000L (no)	1995-04-24
NO301637B1 (no)	1997-11-24
UA41316C2 (uk)	2001-09-17
US5646173A (en)	1997-07-08
DK0657426T3 (da)	1999-04-26
JPH07149725A (ja)	1995-06-13
IL111315A (en)	1999-10-28
KR100348029B1 (ko)	2002-12-28
NZ264711A (en)	1996-07-26
DE59406489D1 (de)	1998-08-27
IL111315A0 (en)	1994-12-29
FI944970A0 (fi)	1994-10-21
EP0657426A3 (fr)	1996-03-06
CZ260394A3 (en)	1995-07-12
CN1057083C (zh)	2000-10-04
FI944970A7 (fi)	1995-04-23
JP2638751B2 (ja)	1997-08-06
RU2128649C1 (ru)	1999-04-10
CA2132887A1 (fr)	1995-04-23
RU94037968A (ru)	1996-09-10
EP0657426A2 (fr)	1995-06-14
AU7583894A (en)	1995-05-11
AU680543B2 (en)	1997-07-31
HU9402985D0 (en)	1995-02-28
CN1105989A (zh)	1995-08-02
HUT70443A (en)	1995-10-30
CA2132887C (fr)	2007-07-17
ES2120551T3 (es)	1998-11-01
ATE168675T1 (de)	1998-08-15
KR950011407A (ko)	1995-05-15
NO944000D0 (no)	1994-10-21
HU217840B (hu)	2000-04-28
EP0657426B1 (fr)	1998-07-22
TW334423B (en)	1998-06-21

Legal Events

Date	Code	Title	Description
2008-04-30	MA	Patent expired

Publication	Publication Date	Title
FI107918B (fi)	2001-10-31	Menetelmä terapeuttisesti aktiivisten trisyklisten 1-aminoalkyylipyrrolijohdannaisten valmistamiseksi
US7183282B2 (en)	2007-02-27	Substituted heterocycle fused γ-carbolines
US6552017B1 (en)	2003-04-22	Substituted heterocycle fused gamma-carbolines
US6713471B1 (en)	2004-03-30	Substituted heterocycle fused gamma-carbolines
EP2054421B1 (fr)	2010-11-17	Pyrazolopyrimidines, procédé permettant de les préparer et de les utiliser en tant que médicaments
AU665207B2 (en)	1995-12-21	Quinazoline derivatives as acetylcholinesterase inhibitors
EP2090576A1 (fr)	2009-08-19	6-halo-pyrazolo[1,5-a]pyridines, leur procédé de préparation et leur utilisation en tant que modulateurs des récepteurs metabotropiques du glutamate (mGluR)
WO2009095254A1 (fr)	2009-08-06	Pyrazolopyrimidines, leur méthode de préparation et leur utilisation comme médicaments
Forbes et al.	1995	5-Methyl-1-(3-pyridylcarbamoyl)-1, 2, 3, 5-tetrahydropyrrolo [2, 3-f] indole: a novel 5-HT2C/5-HT2B receptor antagonist with improved affinity, selectivity, and oral activity
KR20030070590A (ko)	2003-08-30	세로토닌 효능제 및 길항제로서 치환된 피롤로퀴놀린 및피리도퀴놀린
NZ272731A (en)	1996-09-25	Tricyclic-1-aminoethylpyrazole derivatives, preparation and pharmaceutical compositions thereof
EP0869958B1 (fr)	2004-12-29	Nouveaux derives d'indol-2,3-dion-3-oxime
WO1994021608A1 (fr)	1994-09-29	Indoletetralines a activite dopaminergique
HUP0002843A2 (hu)	2001-04-28	Új béta-karbolin-származékok, eljárás előállításukra és az ezeket tartalmazó gyógyszerkészítmények
CA2076948C (fr)	2002-04-16	Derives d'isatineoxime; preparation et utilisation
RU2284325C2 (ru)	2006-09-27	Производные фенил-3-аминометил-хинолона-2 в качестве ингибиторов no-синтетазы, способ их получения, биологически активные соединения и фармацевтическая композиция на их основе
WO2006054912A1 (fr)	2006-05-26	Derives d'aryl(hetaryl)-3-aminomethylchinolone-2 utilises en tant qu'inhibiteurs de no-synthetase et de cyclo-oxygenase-2, procedes de leur fabrication et compositions pharmaceutiques sur leur base
PL194852B1 (pl)	2007-07-31	Nowe pochodne indan-1-olu, sposób ich wytwarzania i zawierające je kompozycje farmaceutyczne
US3980797A (en)	1976-09-14	Hexahydro-diazepino-indole derivatives
PL179511B1 (pl)	2000-09-29	Tricykliczne pochodne 1-aminoetylopirolu, sposób ich wytwarzaniaoraz zawierajace je srodki lecznicze PL PL PL PL PL