SK147297A3 - Piperazino derivatives as neurokinin antagonists - Google Patents

Piperazino derivatives as neurokinin antagonists Download PDF

Info

Publication number: SK147297A3
Authority: SK; Slovakia
Prior art keywords: formula; mmol; compound; reaction; compounds
Prior art date: 1995-05-02

Application number

SK1472-97A

Other languages

English (en)

Slovak (sk)

Inventor

Ho-Jane Shue

Neng-Yang Shih

David J Blythin

Xiao Chen

Wing C Tom

John J Piwinski

Kevin D Mccormick

Original Assignee

Schering Corp

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.)

1995-05-02

Filing date

1996-05-01

Publication date

1998-07-08

1995-05-02 Priority claimed from US08/432,739 external-priority patent/US5719156A/en

1996-05-01 Application filed by Schering Corp filed Critical Schering Corp

1998-07-08 Publication of SK147297A3 publication Critical patent/SK147297A3/sk

Links

239000005557 antagonist Substances 0.000 title abstract description 4
-1 Piperazino Chemical class 0.000 title description 39
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
150000003839 salts Chemical group 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 10
229910052740 iodine Inorganic materials 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910004013 NO 2 Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 194
208000006673 asthma Diseases 0.000 abstract description 7
230000001684 chronic effect Effects 0.000 abstract 1
208000023504 respiratory system disease Diseases 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 197
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
239000000243 solution Substances 0.000 description 92
238000006243 chemical reaction Methods 0.000 description 91
238000000034 method Methods 0.000 description 81
239000007787 solid Substances 0.000 description 55
238000002360 preparation method Methods 0.000 description 43
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
239000002904 solvent Substances 0.000 description 37
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
229920006395 saturated elastomer Polymers 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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238000003818 flash chromatography Methods 0.000 description 27
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
102100024304 Protachykinin-1 Human genes 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
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229910002027 silica gel Inorganic materials 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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239000000543 intermediate Substances 0.000 description 18
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125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
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235000019439 ethyl acetate Nutrition 0.000 description 15
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 14
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PUJZPGUYDJGSAC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1NCCNC1 PUJZPGUYDJGSAC-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 9
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101800003906 Substance P Proteins 0.000 description 8
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RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 7
HVFQJWGYVXKLTE-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HVFQJWGYVXKLTE-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
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229940125782 compound 2 Drugs 0.000 description 7
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231100000673 dose–response relationship Toxicity 0.000 description 7
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125000001424 substituent group Chemical group 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
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210000003437 trachea Anatomy 0.000 description 7
OIJOTGFCYGNHDS-UHFFFAOYSA-N 2-amino-2-(3,4-dichlorophenyl)acetonitrile Chemical compound N#CC(N)C1=CC=C(Cl)C(Cl)=C1 OIJOTGFCYGNHDS-UHFFFAOYSA-N 0.000 description 6
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NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
OJMSAPUIRBBPAS-UHFFFAOYSA-N 1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-3-phenylpiperazine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2CC(NCC2)C=2C=CC=CC=2)=C1 OJMSAPUIRBBPAS-UHFFFAOYSA-N 0.000 description 4
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RKKAPCSDNLGCTJ-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]piperazin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1C(=O)NCCN1 RKKAPCSDNLGCTJ-UHFFFAOYSA-N 0.000 description 4
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Classifications

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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Neurology (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1472-97A 1995-05-02 1996-05-01 Piperazino derivatives as neurokinin antagonists SK147297A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/432,739 US5719156A (en)	1995-05-02	1995-05-02	Piperazino derivatives as neurokinin antagonists
US308495P	1995-08-31	1995-08-31
PCT/US1996/005660 WO1996034864A1 (fr)	1995-05-02	1996-05-01	Derives piperazino en tant qu'antagonistes des neurokinines

Publications (1)

Publication Number	Publication Date
SK147297A3 true SK147297A3 (en)	1998-07-08

Family

ID=26671291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1472-97A SK147297A3 (en)	1995-05-02	1996-05-01	Piperazino derivatives as neurokinin antagonists

Country Status (18)

Country	Link
EP (1)	EP0823906B1 (fr)
JP (1)	JP4173912B2 (fr)
KR (1)	KR19990008230A (fr)
CN (1)	CN1111528C (fr)
AT (1)	ATE244712T1 (fr)
AU (1)	AU705683B2 (fr)
BR (1)	BR9608245A (fr)
CA (1)	CA2218887C (fr)
CZ (1)	CZ342397A3 (fr)
DE (1)	DE69629023T2 (fr)
ES (1)	ES2197238T3 (fr)
HU (1)	HUP9801382A3 (fr)
MX (1)	MX9708416A (fr)
NO (1)	NO315852B1 (fr)
NZ (1)	NZ307716A (fr)
PL (1)	PL323235A1 (fr)
SK (1)	SK147297A3 (fr)
WO (1)	WO1996034864A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5892039A (en) *	1995-08-31	1999-04-06	Schering Corporation	Piperazino derivatives as neurokinin antagonists
US5968929A (en) *	1996-10-30	1999-10-19	Schering Corporation	Piperazino derivatives as neurokinin antagonists
ATE325118T1 (de) *	1996-10-30	2006-06-15	Schering Corp	Piperazinoderivate als neurokinin-antagonisten
US5783579A (en) *	1996-12-20	1998-07-21	Schering Corporation	Spiro-substituted azacyclic-substituted piperazino derivatives as neurokinin antagonists
KR100420616B1 (ko) *	1996-12-26	2004-05-17	동화약품공업주식회사	신규테레프탈산아미드유도체
US6207665B1 (en)	1997-06-12	2001-03-27	Schering Aktiengesellschaft	Piperazine derivatives and their use as anti-inflammatory agents
AUPO735997A0 (en)	1997-06-17	1997-07-10	Fujisawa Pharmaceutical Co., Ltd.	Piperazine derivatives
DE19737334A1 (de) *	1997-08-27	1999-03-04	Solvay Pharm Gmbh	7-Phenyl-1,4-diazepan-Derivate, sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
TW591025B (en) *	2000-06-13	2004-06-11	Fujisawa Pharmaceutical Co	Production of the piperazine derivative
AUPR237301A0 (en) *	2001-01-02	2001-01-25	Fujisawa Pharmaceutical Co., Ltd.	Benzhydryl derivatives
MXPA02002749A (es) *	2001-03-27	2002-10-28	Warner Lambert Co	Derivados de ciclohexilamina como antagonistas del subtipo selectivo del n-metil-d-aspartato.
UA75425C2 (en)	2001-07-09	2006-04-17		Piperazine oxime derivatives with antagonistic activity to nk-1 receptor, use thereof, a pharmaceutical composition based thereon, a method for producing and a method for producing intermediary compounds
AUPR970701A0 (en) *	2001-12-21	2002-01-24	Fujisawa Pharmaceutical Co., Ltd.	Benzhydryl derivatives
CN107602317A (zh) *	2017-08-02	2018-01-19	凯莱英医药集团（天津）股份有限公司	手性2‑氨基‑2‑芳基乙酸衍生物的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8908587D0 (en) *	1989-04-15	1989-06-01	Scras Societe De Conseils De R	New 2-substituted n,n'-ditrimethoxybenzoyl piperazines
WO1992020661A1 (fr) *	1991-05-22	1992-11-26	Merck & Co., Inc.	N, n-diacylpiperazines
US5344830A (en) *	1992-12-10	1994-09-06	Merck & Co., Inc.	N,N-diacylpiperazine tachykinin antagonists
IL111730A (en) *	1993-11-29	1998-12-06	Fujisawa Pharmaceutical Co	Piperazine derivatives, processes for their preparation and pharmaceutical preparations containing them
US5607936A (en) *	1994-09-30	1997-03-04	Merck & Co., Inc.	Substituted aryl piperazines as neurokinin antagonists

1996
- 1996-05-01 WO PCT/US1996/005660 patent/WO1996034864A1/fr not_active Application Discontinuation
- 1996-05-01 KR KR1019970707756A patent/KR19990008230A/ko active IP Right Grant
- 1996-05-01 DE DE69629023T patent/DE69629023T2/de not_active Expired - Lifetime
- 1996-05-01 JP JP53335596A patent/JP4173912B2/ja not_active Expired - Fee Related
- 1996-05-01 BR BR9608245A patent/BR9608245A/pt not_active Application Discontinuation
- 1996-05-01 SK SK1472-97A patent/SK147297A3/sk unknown
- 1996-05-01 AU AU57141/96A patent/AU705683B2/en not_active Ceased
- 1996-05-01 CZ CZ973423A patent/CZ342397A3/cs unknown
- 1996-05-01 HU HU9801382A patent/HUP9801382A3/hu unknown
- 1996-05-01 CN CN96195171A patent/CN1111528C/zh not_active Expired - Fee Related
- 1996-05-01 ES ES96915342T patent/ES2197238T3/es not_active Expired - Lifetime
- 1996-05-01 CA CA002218887A patent/CA2218887C/fr not_active Expired - Fee Related
- 1996-05-01 MX MX9708416A patent/MX9708416A/es not_active IP Right Cessation
- 1996-05-01 EP EP96915342A patent/EP0823906B1/fr not_active Expired - Lifetime
- 1996-05-01 PL PL96323235A patent/PL323235A1/xx unknown
- 1996-05-01 AT AT96915342T patent/ATE244712T1/de not_active IP Right Cessation
- 1996-05-01 NZ NZ307716A patent/NZ307716A/en unknown
1997
- 1997-10-31 NO NO19975028A patent/NO315852B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
PL323235A1 (en)	1998-03-16
JPH11504921A (ja)	1999-05-11
CA2218887A1 (fr)	1996-11-07
NO975028L (no)	1997-12-30
ES2197238T3 (es)	2004-01-01
DE69629023T2 (de)	2004-04-22
BR9608245A (pt)	1999-05-04
JP4173912B2 (ja)	2008-10-29
HUP9801382A2 (hu)	1999-06-28
CN1189829A (zh)	1998-08-05
WO1996034864A1 (fr)	1996-11-07
NO975028D0 (no)	1997-10-31
NO315852B1 (no)	2003-11-03
EP0823906B1 (fr)	2003-07-09
CA2218887C (fr)	2008-04-29
EP0823906A1 (fr)	1998-02-18
AU705683B2 (en)	1999-05-27
KR19990008230A (ko)	1999-01-25
DE69629023D1 (de)	2003-08-14
CZ342397A3 (cs)	1998-03-18
ATE244712T1 (de)	2003-07-15
CN1111528C (zh)	2003-06-18
AU5714196A (en)	1996-11-21
NZ307716A (en)	1999-10-28
HUP9801382A3 (en)	2000-09-28
MX9708416A (es)	1998-02-28

Publication	Publication Date	Title
US5981520A (en)	1999-11-09	Piperazino derivatives as neurokinin antagonists
US6051575A (en)	2000-04-18	Piperazino derivatives as neurokinin antagonists
AU706744B2 (en)	1999-06-24	Piperidine derivatives as neurokinin antagonists
US5719156A (en)	1998-02-17	Piperazino derivatives as neurokinin antagonists
EP0850236B1 (fr)	2001-07-04	Derives de piperazino antagonistes de la neurokinine
US5869488A (en)	1999-02-09	Piperazino derivatives as neurokinin antagonists
SK147297A3 (en)	1998-07-08	Piperazino derivatives as neurokinin antagonists
US5892039A (en)	1999-04-06	Piperazino derivatives as neurokinin antagonists
DE60206781T2 (de)	2006-06-01	2-substituierte 1-arylpiperazine als tachykinin-antagonisten und/oder serotonin-wiederaufnahme-hemmer
AU733454B2 (en)	2001-05-17	Piperazino derivatives as neurokinin antagonists
JP2009523747A (ja)	2009-06-25	α７ニコチン性アセチルコリン受容体のモジュレーターおよびその治療上の使用
KR19990044138A (ko)	1999-06-25	뉴로키닌 길항제로서의 피페라지노 유도체
MXPA99001751A (en)	1999-09-20	Piperazino derivatives as neurokinin antagonists