SK285585B6 - Tricyklický delta 3-piperidín, spôsob jeho prípravy, použitie a prostriedok s jeho obsahom - Google Patents

Tricyklický delta 3-piperidín, spôsob jeho prípravy, použitie a prostriedok s jeho obsahom Download PDF

Info

Publication number: SK285585B6
Authority: SK; Slovakia
Prior art keywords: group; formula; alkyl; carbon atoms; hydrogen
Prior art date: 1998-10-06

Application number

SK432-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK4322001A3 (en

Inventor

Ludo Edmond Josephine Kennis

Den Keybus Frans Maria Alfons Van

Josephus Carolus Mertens

Original Assignee

Janssen Pharmaceutica N. V.

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.)

1998-10-06

Filing date

1999-10-01

Publication date

2007-04-05

1999-10-01 Application filed by Janssen Pharmaceutica N. V. filed Critical Janssen Pharmaceutica N. V.

2002-01-07 Publication of SK4322001A3 publication Critical patent/SK4322001A3/sk

2007-04-05 Publication of SK285585B6 publication Critical patent/SK285585B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 19
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 title claims 2
239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
-1 nitro, hydroxy Chemical group 0.000 claims abstract description 33
150000003839 salts Chemical class 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
150000002431 hydrogen Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 6
150000002367 halogens Chemical group 0.000 claims abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 68
239000002904 solvent Substances 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 10
239000002585 base Substances 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000007126 N-alkylation reaction Methods 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
208000018737 Parkinson disease Diseases 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
208000020401 Depressive disease Diseases 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
238000005932 reductive alkylation reaction Methods 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 22
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 2
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239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 abstract 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
239000012965 benzophenone Substances 0.000 abstract 1
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150000003053 piperidines Chemical class 0.000 abstract 1
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108060003345 Adrenergic Receptor Proteins 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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150000007524 organic acids Chemical class 0.000 description 1
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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JADFCQKRKICRKI-UHFFFAOYSA-N quinoline;sulfane Chemical compound S.N1=CC=CC2=CC=CC=C21 JADFCQKRKICRKI-UHFFFAOYSA-N 0.000 description 1
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BEKDZRXUWYOOPU-UHFFFAOYSA-N tert-butyl n-(4-chlorobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCl BEKDZRXUWYOOPU-UHFFFAOYSA-N 0.000 description 1
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BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
229960001600 xylazine Drugs 0.000 description 1

Classifications

- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- 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
- 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
- A61P25/24—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
- A61P25/28—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
- A61P27/00—Drugs for disorders of the senses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Psychiatry (AREA)
Obesity (AREA)
Reproductive Health (AREA)
Hematology (AREA)
Psychology (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Hospice & Palliative Care (AREA)
Gynecology & Obstetrics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Hydrogenated Pyridines (AREA)

SK432-2001A 1998-10-06 1999-10-01 Tricyklický delta 3-piperidín, spôsob jeho prípravy, použitie a prostriedok s jeho obsahom SK285585B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98203370		1998-10-06
PCT/EP1999/007419 WO2000020421A2 (en)	1998-10-06	1999-10-01	TRICYCLIC Δ3-PIPERIDINES AS α2-ANTAGONISTS

Publications (2)

Publication Number	Publication Date
SK4322001A3 SK4322001A3 (en)	2002-01-07
SK285585B6 true SK285585B6 (sk)	2007-04-05

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ID=8234191

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK432-2001A SK285585B6 (sk)	1998-10-06	1999-10-01	Tricyklický delta 3-piperidín, spôsob jeho prípravy, použitie a prostriedok s jeho obsahom

Country Status (30)

Country	Link
US (1)	US6495555B1 (cs)
EP (1)	EP1119571B1 (cs)
JP (1)	JP4590101B2 (cs)
KR (1)	KR20010071843A (cs)
CN (1)	CN1131230C (cs)
AR (1)	AR024216A1 (cs)
AT (1)	ATE232869T1 (cs)
AU (1)	AU760502B2 (cs)
BG (1)	BG64872B1 (cs)
BR (1)	BR9913507A (cs)
CA (1)	CA2345622C (cs)
CZ (1)	CZ20011104A3 (cs)
DE (1)	DE69905478T2 (cs)
DK (1)	DK1119571T3 (cs)
EE (1)	EE04770B1 (cs)
ES (1)	ES2193751T3 (cs)
HU (1)	HUP0104002A3 (cs)
ID (1)	ID28032A (cs)
IL (1)	IL142443A0 (cs)
NO (1)	NO20011270L (cs)
NZ (1)	NZ510115A (cs)
PL (1)	PL347894A1 (cs)
PT (1)	PT1119571E (cs)
RU (1)	RU2230744C2 (cs)
SI (1)	SI1119571T1 (cs)
SK (1)	SK285585B6 (cs)
TR (1)	TR200100952T2 (cs)
TW (1)	TWI248441B (cs)
UA (1)	UA69420C2 (cs)
WO (1)	WO2000020421A2 (cs)

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ID28451A (id) *	1998-10-06	2001-05-24	Janssen Pharmaceutica Nv	Trisiklik piperidin-δ3 sebagai bahan farmasi
ATE521593T1 (de) *	2002-04-03	2011-09-15	Orion Corp	Verwendung eines alfa2-adrenorezeptorantagonisten bei mit dem zns zusammenhängenden erkrankungen
WO2005100355A1 (ja)	2004-04-12	2005-10-27	Taisho Pharmaceutical Co., Ltd.	環状アミン化合物
WO2006006740A1 (ja) *	2004-07-14	2006-01-19	Japan Tobacco Inc.	３−アミノベンズアミド化合物及びバニロイド受容体１型(ｖｒ１)活性阻害剤
MX2007000480A (es) *	2004-07-15	2007-03-29	Japan Tobacco Inc	Compuesto de benzamida fusionado e inhibidor de actividad de receptor de vainilloide 1.
US7906508B2 (en) *	2005-12-28	2011-03-15	Japan Tobacco Inc.	3,4-dihydrobenzoxazine compounds and inhibitors of vanilloid receptor subtype 1 (VRI) activity
US8399465B2 (en)	2009-05-14	2013-03-19	Janssen Pharmaceutica Nv	Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene A4 hydrolase
EP3083610A1 (de)	2013-12-19	2016-10-26	Bayer Pharma Aktiengesellschaft	Substituierte bipiperidinyl-derivate als adrenrezeptor alpha 2c antagonisten
KR20160098424A (ko) *	2013-12-19	2016-08-18	바이엘 파마 악티엔게젤샤프트	치환된 피페리디닐-테트라히드로퀴놀린
CR20160276A (es) *	2013-12-19	2016-10-20	Bayer Pharma AG	"piperidiniltetrahidroquinolinas sustituidas y su uso como antagonistas de los adenoreceptores alpha-2c"
CN114276359B (zh) *	2022-01-05	2023-05-05	浙江大学	一种1,2,3,4-四氢苯并[4,5]呋喃[2,3-c]吡啶衍生物的制备方法

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SU926914A1 (ru) *	1980-05-26	1992-04-23	Научно-исследовательский институт фармакологии АМН СССР	Производные 1,2,3,4-тетрагидробензофуро[3,2-с]-пиридина или хлоргидрат, обладающие р дом свойств анальгетиков и антагонистов морфина
DE3522959A1 (de) *	1985-06-27	1987-01-08	Merck Patent Gmbh	Indolderivate
US4673680A (en) *	1985-09-18	1987-06-16	Pendleton Robert G	α2 -adrenergic receptor antagonists as modifiers of gastrointestinal motility
US4985422A (en) *	1988-04-27	1991-01-15	Glaxo Group Limited	Lactam derivatives
US4971974A (en) *	1988-06-16	1990-11-20	Neurex Corporation	Benzothiophenes as appetite suppressants
US5100891A (en) *	1991-01-18	1992-03-31	Hoechst-Roussel Pharmaceuticals Inc.	Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds
AU735764B2 (en) *	1996-12-06	2001-07-12	Abbott Laboratories	Benzopyranopyrrole and benzopyranopyridine alpha-1 adrenergic compounds
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ID28451A (id) *	1998-10-06	2001-05-24	Janssen Pharmaceutica Nv	Trisiklik piperidin-δ3 sebagai bahan farmasi

1999
- 1999-01-10 UA UA2001031999A patent/UA69420C2/uk unknown
- 1999-10-01 ID IDW20010780A patent/ID28032A/id unknown
- 1999-10-01 TW TW088116898A patent/TWI248441B/zh not_active IP Right Cessation
- 1999-10-01 JP JP2000574533A patent/JP4590101B2/ja not_active Expired - Fee Related
- 1999-10-01 HU HU0104002A patent/HUP0104002A3/hu unknown
- 1999-10-01 RU RU2001111812/04A patent/RU2230744C2/ru not_active IP Right Cessation
- 1999-10-01 BR BR9913507-8A patent/BR9913507A/pt not_active IP Right Cessation
- 1999-10-01 SI SI9930264T patent/SI1119571T1/xx unknown
- 1999-10-01 KR KR1020017000442A patent/KR20010071843A/ko not_active Ceased
- 1999-10-01 DK DK99950627T patent/DK1119571T3/da active
- 1999-10-01 CN CN99811682A patent/CN1131230C/zh not_active Expired - Fee Related
- 1999-10-01 US US09/806,547 patent/US6495555B1/en not_active Expired - Lifetime
- 1999-10-01 CZ CZ20011104A patent/CZ20011104A3/cs unknown
- 1999-10-01 TR TR2001/00952T patent/TR200100952T2/xx unknown
- 1999-10-01 SK SK432-2001A patent/SK285585B6/sk unknown
- 1999-10-01 AU AU63341/99A patent/AU760502B2/en not_active Ceased
- 1999-10-01 WO PCT/EP1999/007419 patent/WO2000020421A2/en not_active Ceased
- 1999-10-01 DE DE69905478T patent/DE69905478T2/de not_active Expired - Lifetime
- 1999-10-01 AT AT99950627T patent/ATE232869T1/de not_active IP Right Cessation
- 1999-10-01 PT PT99950627T patent/PT1119571E/pt unknown
- 1999-10-01 CA CA002345622A patent/CA2345622C/en not_active Expired - Fee Related
- 1999-10-01 EP EP99950627A patent/EP1119571B1/en not_active Expired - Lifetime
- 1999-10-01 NZ NZ510115A patent/NZ510115A/xx unknown
- 1999-10-01 EE EEP200100209A patent/EE04770B1/xx not_active IP Right Cessation
- 1999-10-01 IL IL14244399A patent/IL142443A0/xx not_active IP Right Cessation
- 1999-10-01 ES ES99950627T patent/ES2193751T3/es not_active Expired - Lifetime
- 1999-10-01 PL PL99347894A patent/PL347894A1/xx not_active Application Discontinuation
- 1999-10-05 AR ARP990105038A patent/AR024216A1/es not_active Application Discontinuation
2001
- 2001-03-12 BG BG105332A patent/BG64872B1/bg unknown
- 2001-03-13 NO NO20011270A patent/NO20011270L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69905478D1 (de)	2003-03-27
WO2000020421A2 (en)	2000-04-13
NO20011270D0 (no)	2001-03-13
ES2193751T3 (es)	2003-11-01
BG64872B1 (bg)	2006-07-31
TWI248441B (en)	2006-02-01
NO20011270L (no)	2001-03-13
JP4590101B2 (ja)	2010-12-01
UA69420C2 (uk)	2004-09-15
WO2000020421A3 (en)	2000-08-03
PL347894A1 (en)	2002-04-22
SK4322001A3 (en)	2002-01-07
BR9913507A (pt)	2001-06-05
AU760502B2 (en)	2003-05-15
HUP0104002A2 (hu)	2002-03-28
KR20010071843A (ko)	2001-07-31
EP1119571B1 (en)	2003-02-19
CN1332744A (zh)	2002-01-23
DK1119571T3 (da)	2003-05-26
EE200100209A (et)	2002-06-17
CA2345622C (en)	2007-12-04
EE04770B1 (et)	2007-02-15
CZ20011104A3 (cs)	2001-12-12
HK1038010A1 (en)	2002-03-01
US6495555B1 (en)	2002-12-17
RU2230744C2 (ru)	2004-06-20
PT1119571E (pt)	2003-06-30
JP2002526545A (ja)	2002-08-20
AR024216A1 (es)	2002-09-25
SI1119571T1 (en)	2003-08-31
CN1131230C (zh)	2003-12-17
AU6334199A (en)	2000-04-26
TR200100952T2 (tr)	2001-10-22
NZ510115A (en)	2002-11-26
HUP0104002A3 (en)	2003-12-29
ID28032A (id)	2001-05-03
EP1119571A2 (en)	2001-08-01
ATE232869T1 (de)	2003-03-15
IL142443A0 (en)	2002-03-10
CA2345622A1 (en)	2000-04-13
DE69905478T2 (de)	2004-03-18
BG105332A (en)	2001-11-30

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MXPA01003512A (en)	2001-12-04	TRICYCLIC&Dgr;3-PIPERIDINES AS PHARMACEUTICALS
MXPA01003514A (en)	2001-12-04	BENZOTHIENO[3,2-c]PYRIDINES AS&agr;2
HK1038010B (en)	2003-05-23	Tricyclic delta3-piperidines as alpha2-antagonists
HK1038009B (en)	2004-12-24	Tricyclic delta3-piperidines as pharmaceuticals
HK1039113B (en)	2007-07-20	Benzothieno[3,2-c]pyridines as alpha2 antagonists