SK13012001A3 - N-(2-Fenyl-4-amino-butyl)-1-naftamidy ako antagonisty receptora neurokinínu-1 - Google Patents

N-(2-Fenyl-4-amino-butyl)-1-naftamidy ako antagonisty receptora neurokinínu-1 Download PDF

Info

Publication number: SK13012001A3
Authority: SK; Slovakia
Prior art keywords: group; cyano; compound; alkyl; methyl
Prior art date: 1999-04-06

Application number

SK1301-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Robert Bernstein

Original Assignee

Astrazeneca Ab

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.)

1999-04-06

Filing date

2000-04-03

Publication date

2002-04-04

2000-04-03 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2002-04-04 Publication of SK13012001A3 publication Critical patent/SK13012001A3/sk

Links

239000002742 neurokinin 1 receptor antagonist Substances 0.000 title description 3
VFTQJCVZNTYOKM-UHFFFAOYSA-N n-(4-amino-2-phenylbutyl)naphthalene-1-carboxamide Chemical class C=1C=CC2=CC=CC=C2C=1C(=O)NCC(CCN)C1=CC=CC=C1 VFTQJCVZNTYOKM-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 80
125000003118 aryl group Chemical group 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
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 abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 2
-1 C 1-6 -alkanoyl Chemical group 0.000 claims description 43
238000000034 method Methods 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
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125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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206010020772 Hypertension Diseases 0.000 claims description 2
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125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
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125000005843 halogen group Chemical group 0.000 claims 1
102100024304 Protachykinin-1 Human genes 0.000 abstract description 16
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ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 abstract description 7
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125000001475 halogen functional group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 23
239000000203 mixture Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
238000001819 mass spectrum Methods 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 11
238000011282 treatment Methods 0.000 description 11
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
108010040718 Neurokinin-1 Receptors Proteins 0.000 description 8
102000002002 Neurokinin-1 Receptors Human genes 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000007787 solid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
101800000399 Neurokinin A Proteins 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000556 agonist Substances 0.000 description 6
229910002091 carbon monoxide Inorganic materials 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QDSLQEBZBNSMQU-QGZVFWFLSA-N 3-cyano-n-[(2s)-2-(3,4-dichlorophenyl)-4-oxobutyl]-2-methoxy-n-methylnaphthalene-1-carboxamide Chemical compound C1([C@H](CC=O)CN(C)C(=O)C2=C3C=CC=CC3=CC(=C2OC)C#N)=CC=C(Cl)C(Cl)=C1 QDSLQEBZBNSMQU-QGZVFWFLSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000008485 antagonism Effects 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
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HEAUFJZALFKPBA-JPQUDPSNSA-N (3s)-3-[[(2s,3r)-2-[[(2s)-6-amino-2-[[(2s)-2-amino-3-(1h-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]-3-hydroxybutanoyl]amino]-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[2-[[(2s)-1-[[(2s)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-JPQUDPSNSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
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239000005557 antagonist Substances 0.000 description 4
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BAIYNFZNNISXSV-UHFFFAOYSA-N methyl 3-bromonaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC(Br)=CC2=C1 BAIYNFZNNISXSV-UHFFFAOYSA-N 0.000 description 3
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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230000024883 vasodilation Effects 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
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Classifications

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- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
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- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
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- 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
- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pulmonology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Rheumatology (AREA)
Otolaryngology (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Psychology (AREA)
Dermatology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK1301-2001A 1999-04-06 2000-04-03 N-(2-Fenyl-4-amino-butyl)-1-naftamidy ako antagonisty receptora neurokinínu-1 SK13012001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9907571.5A GB9907571D0 (en)	1999-04-06	1999-04-06	Compounds
PCT/GB2000/001252 WO2000059873A1 (en)	1999-04-06	2000-04-03	N-(2-phenyl-4-amino-butyl)-1-naphthamides as neurokinin-1 receptor antagonists

Publications (1)

Publication Number	Publication Date
SK13012001A3 true SK13012001A3 (sk)	2002-04-04

Family

ID=10850835

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1301-2001A SK13012001A3 (sk)	1999-04-06	2000-04-03	N-(2-Fenyl-4-amino-butyl)-1-naftamidy ako antagonisty receptora neurokinínu-1

Country Status (25)

Country	Link
US (3)	US6476077B1 (ko)
EP (1)	EP1169302B1 (ko)
JP (1)	JP2002541137A (ko)
KR (1)	KR20010102580A (ko)
CN (2)	CN1534017A (ko)
AT (1)	ATE277893T1 (ko)
AU (1)	AU3569200A (ko)
BG (1)	BG106074A (ko)
BR (1)	BR0009582A (ko)
CA (1)	CA2368240A1 (ko)
CZ (1)	CZ20013574A3 (ko)
DE (1)	DE60014343T2 (ko)
EE (1)	EE200100520A (ko)
GB (1)	GB9907571D0 (ko)
HK (1)	HK1044145A1 (ko)
HU (1)	HUP0200707A3 (ko)
IL (1)	IL145645A0 (ko)
IS (1)	IS6087A (ko)
NO (1)	NO20014855L (ko)
PL (1)	PL350568A1 (ko)
SK (1)	SK13012001A3 (ko)
TR (1)	TR200102875T2 (ko)
UA (1)	UA67839C2 (ko)
WO (1)	WO2000059873A1 (ko)
ZA (1)	ZA200108176B (ko)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9907571D0 (en) *	1999-04-06	1999-05-26	Zeneca Ltd	Compounds
GB0019008D0 (en) *	2000-08-04	2000-09-27	Astrazeneca Ab	Therapeutic compounds
SE0201938D0 (sv) *	2002-06-20	2002-06-20	Astrazeneca Ab	New process
WO2004041671A1 (en) *	2002-11-05	2004-05-21	Astrazeneca Ab	Security container with locking closure and method for locking a closure
AU2003291589A1 (en) *	2002-12-20	2004-07-14	Astrazeneca Ab	Piperidine amine compounds and their use
CA2580694A1 (en) *	2004-09-23	2006-03-30	Alexander Michalow	Methods for regulating neurotransmitter systems by inducing counteradaptations
US20080045610A1 (en) *	2004-09-23	2008-02-21	Alexander Michalow	Methods for regulating neurotransmitter systems by inducing counteradaptations
ES2672099T3 (es)	2011-07-04	2018-06-12	Irbm - Science Park S.P.A.	Antagonistas del receptor NK-1 para el tratamiento de la neovascularización corneal
CN107635557A (zh)	2015-05-18	2018-01-26	尼尔医疗有限公司	用于治疗性激素依赖性疾病的双重nk‑1/nk‑3受体拮抗剂
RU2020131446A (ru)	2018-02-26	2022-03-28	Оспедале Сан Раффаэле С.Р.Л.	Антагонисты nk-1 для применения в лечении глазной боли
CN112292132A (zh)	2018-03-14	2021-01-29	KaNDy治疗有限公司	含有双重nk-1/nk-3受体拮抗剂的新颖的药物制剂
RU2697414C1 (ru)	2018-05-11	2019-08-14	Общество с ограниченной ответственностью "АЙ БИ ДИ Терапевтикс"	Новый антагонист тахикининовых рецепторов и его применение
WO2021180885A1 (en)	2020-03-11	2021-09-16	Ospedale San Raffaele S.R.L.	Treatment of stem cell deficiency

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE903957A1 (en) *	1989-11-06	1991-05-08	Sanofi Sa	Aromatic amine compounds, their method of preparation and¹pharmaceutical compositions in which they are present
JPH08511522A (ja)	1993-06-07	1996-12-03	メルクエンドカンパニーインコーポレーテッド	ニューロキニンアンタゴニストとしてのスピロ置換アザ環
DK0777659T3 (da) *	1994-08-15	2001-09-03	Merck Sharp & Dohme	Morpholinderivater og deres anvendelse som terapeutiske midler
AU5522498A (en)	1996-12-13	1998-07-03	Merck & Co., Inc.	Substituted aryl piperazines as modulators of chemokine receptor activity
GB9907571D0 (en) *	1999-04-06	1999-05-26	Zeneca Ltd	Compounds
HUP0400252A3 (en) *	2001-03-21	2011-09-28	Pharmacopeia Drug Discovery	Aryl and biaryl compounds having mch modulatory activity, pharmaceutical compositions containing them and process for producing them

1999
- 1999-04-06 GB GBGB9907571.5A patent/GB9907571D0/en not_active Ceased
2000
- 2000-03-04 UA UA2001117535A patent/UA67839C2/uk unknown
- 2000-04-03 KR KR1020017012692A patent/KR20010102580A/ko not_active Application Discontinuation
- 2000-04-03 CA CA002368240A patent/CA2368240A1/en not_active Abandoned
- 2000-04-03 HU HU0200707A patent/HUP0200707A3/hu unknown
- 2000-04-03 AT AT00914298T patent/ATE277893T1/de not_active IP Right Cessation
- 2000-04-03 SK SK1301-2001A patent/SK13012001A3/sk unknown
- 2000-04-03 IL IL14564500A patent/IL145645A0/xx unknown
- 2000-04-03 EP EP00914298A patent/EP1169302B1/en not_active Expired - Lifetime
- 2000-04-03 CN CNA2004100053467A patent/CN1534017A/zh active Pending
- 2000-04-03 BR BR0009582-6A patent/BR0009582A/pt not_active IP Right Cessation
- 2000-04-03 PL PL00350568A patent/PL350568A1/xx unknown
- 2000-04-03 CZ CZ20013574A patent/CZ20013574A3/cs unknown
- 2000-04-03 JP JP2000609386A patent/JP2002541137A/ja active Pending
- 2000-04-03 US US09/937,981 patent/US6476077B1/en not_active Expired - Fee Related
- 2000-04-03 CN CN00805623A patent/CN1345307A/zh active Pending
- 2000-04-03 AU AU35692/00A patent/AU3569200A/en not_active Abandoned
- 2000-04-03 TR TR2001/02875T patent/TR200102875T2/xx unknown
- 2000-04-03 EE EEP200100520A patent/EE200100520A/xx unknown
- 2000-04-03 DE DE60014343T patent/DE60014343T2/de not_active Expired - Fee Related
- 2000-04-03 WO PCT/GB2000/001252 patent/WO2000059873A1/en not_active Application Discontinuation
2001
- 2001-09-26 IS IS6087A patent/IS6087A/is unknown
- 2001-10-04 ZA ZA200108176A patent/ZA200108176B/en unknown
- 2001-10-05 NO NO20014855A patent/NO20014855L/no not_active Application Discontinuation
- 2001-11-01 BG BG106074A patent/BG106074A/xx unknown
2002
- 2002-06-26 HK HK02104758.2A patent/HK1044145A1/zh unknown
- 2002-11-01 US US10/286,624 patent/US6586432B2/en not_active Expired - Fee Related
2003
- 2003-06-30 US US10/611,052 patent/US6821973B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CZ20013574A3 (cs)	2002-05-15
ZA200108176B (en)	2003-01-06
ATE277893T1 (de)	2004-10-15
NO20014855L (no)	2001-12-06
IS6087A (is)	2001-09-26
TR200102875T2 (tr)	2002-01-21
AU3569200A (en)	2000-10-23
WO2000059873A1 (en)	2000-10-12
US6821973B2 (en)	2004-11-23
GB9907571D0 (en)	1999-05-26
KR20010102580A (ko)	2001-11-15
US20040106610A1 (en)	2004-06-03
CA2368240A1 (en)	2000-10-12
BG106074A (en)	2002-05-31
UA67839C2 (uk)	2004-07-15
DE60014343T2 (de)	2006-03-02
EE200100520A (et)	2002-12-16
IL145645A0 (en)	2002-06-30
DE60014343D1 (de)	2004-11-04
EP1169302B1 (en)	2004-09-29
BR0009582A (pt)	2001-12-26
US6476077B1 (en)	2002-11-05
HUP0200707A3 (en)	2002-11-28
NO20014855D0 (no)	2001-10-05
CN1534017A (zh)	2004-10-06
PL350568A1 (en)	2002-12-16
US6586432B2 (en)	2003-07-01
EP1169302A1 (en)	2002-01-09
HUP0200707A2 (en)	2002-06-29
JP2002541137A (ja)	2002-12-03
US20030092713A1 (en)	2003-05-15
CN1345307A (zh)	2002-04-17
HK1044145A1 (zh)	2002-10-11

Publication	Publication Date	Title
JP2763036B2 (ja)	1998-06-11	複素環化合物
SK13012001A3 (sk)	2002-04-04	N-(2-Fenyl-4-amino-butyl)-1-naftamidy ako antagonisty receptora neurokinínu-1
EP1119355B1 (en)	2003-01-08	Naphthalenecarboxamides as tachykinin receptor antagonists
US6403601B1 (en)	2002-06-11	N-(2-phenyl-4-piperidinybutyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamides and their use as neurokinin 1 (NK1) and/or neurokinin 2 (NK2) receptor antagonists
JP3498849B2 (ja)	2004-02-23	ニューロキニンａ拮抗剤としての二環式複素環化合物
EP1590335A2 (en)	2005-11-02	Process for preparing pyrrolotriazine kinase inhibitors
JP2003231633A (ja)	2003-08-19	医薬組成物
EP1278719B1 (en)	2005-11-02	Naphthamide neurokinin antagonists for use as medicaments
JP4088154B2 (ja)	2008-05-21	ニューロキニン１拮抗薬
MXPA01010032A (en)	2002-05-09	N-(2-phenyl-4-amino-butyl)-1-naphthamides as neurokinin-1 receptor antagonists
WO2008044632A1 (fr)	2008-04-17	Dérivé de la 1-naphthyl alkylpipéridine
US20030158180A1 (en)	2003-08-21	Naphthamide neurokinin antagonists for use as medicaments
JP2011219467A (ja)	2011-11-04	７−ピペリジノアルキル−３，４−ジヒドロキノロン誘導体を含有する医薬
JPH06211770A (ja)	1994-08-02	シアノアミジン誘導体
KR20110049833A (ko)	2011-05-12	피롤리디닐-알킬-아미드 유도체, 이의 제조방법 및 ｃｃｒ３ 수용체 리간드로서의 이의 치료학적 용도
MXPA01003560A (es)	2001-12-04	Naftalenocarbxamidas como antagonistas receptores de taquicinina
ZA200102658B (en)	2002-07-01	Naphthalenecarboxamides as tachykinin receptor antagonists.