CA2399584A1 - Non peptide tachykinin receptor antagonists - Google Patents

Non peptide tachykinin receptor antagonists Download PDF

Info

Publication number: CA2399584A1
Authority: CA; Canada
Prior art keywords: phenyl; ylmethyl; indol; alkyl; benzofuran
Prior art date: 1999-12-22
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

CA002399584A

Other languages

English (en)

French (fr)

Inventor

David Christopher Horwell

Russell Andrew Lewthwaite

Martin Clive Pritchard

Jennifer Raphy

Hubert Barth

Klaus Steiner

Bernd Schiefermayr

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.)

Warner Lambert Co LLC

Original Assignee

Individual

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.)

1999-12-22

Filing date

2000-12-21

Publication date

2001-06-28

2000-02-22 Priority claimed from EP00103665A external-priority patent/EP1127875A1/en

2000-12-21 Application filed by Individual filed Critical Individual

2001-06-28 Publication of CA2399584A1 publication Critical patent/CA2399584A1/en

Status Abandoned legal-status Critical Current

Links

239000002462 tachykinin receptor antagonist Substances 0.000 title abstract description 7
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150000001875 compounds Chemical class 0.000 claims abstract description 91
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230000001594 aberrant effect Effects 0.000 claims abstract description 10
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206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
210000004881 tumor cell Anatomy 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 120
125000000217 alkyl group Chemical group 0.000 claims description 58
-1 Benzofuran-2-ylmethyl Chemical group 0.000 claims description 46
238000000034 method Methods 0.000 claims description 40
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
230000008569 process Effects 0.000 claims description 19
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
125000002541 furyl group Chemical group 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 18
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208000011231 Crohn disease Diseases 0.000 claims description 12
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WSZFQYQLPMOBHO-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylamino)-2-[(dimethylamino)methyl]-3-(1h-indol-3-yl)-n-(1-phenylethyl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(CN(C)C)(NCC=1OC2=CC=CC=C2C=1)C(=O)NC(C)C1=CC=CC=C1 WSZFQYQLPMOBHO-UHFFFAOYSA-N 0.000 claims description 11
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125000004432 carbon atom Chemical group C* 0.000 claims description 11
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical group [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 11
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125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 10
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HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
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QABYBLFTBSCYHR-UHFFFAOYSA-N 1-(benzotriazol-1-yl)-n,n-dimethylmethanamine Chemical compound C1=CC=C2N(CN(C)C)N=NC2=C1 QABYBLFTBSCYHR-UHFFFAOYSA-N 0.000 claims description 6
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IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 6
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VVDUZZGYBOWDSQ-UHFFFAOYSA-M eschenmoser's salt Chemical compound [I-].C[N+](C)=C VVDUZZGYBOWDSQ-UHFFFAOYSA-M 0.000 claims description 5
UKYTZQPDSUAZSQ-IFUPQEAVSA-N (2s)-2-(1-benzofuran-2-ylmethylamino)-2-[(dimethylamino)methyl]-3-(1h-indol-3-yl)propanoic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2OC(CN[C@@](CC=3C4=CC=CC=C4NC=3)(CN(C)C)C(O)=O)=CC2=C1 UKYTZQPDSUAZSQ-IFUPQEAVSA-N 0.000 claims description 4
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HDMLUGFDPNTTIO-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylcarbamoylamino)-2-(hydroxymethyl)-3-(1h-indol-3-yl)-n-(1-phenylethyl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(CO)(NC(=O)NCC=1OC2=CC=CC=C2C=1)C(=O)NC(C)C1=CC=CC=C1 HDMLUGFDPNTTIO-UHFFFAOYSA-N 0.000 claims description 4
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KCUNTYMNJVXYKZ-JTQLQIEISA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 KCUNTYMNJVXYKZ-JTQLQIEISA-N 0.000 claims description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
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125000001424 substituent group Chemical group 0.000 claims description 4
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 3
NIFMQNFZDATVNO-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylamino)-2-(hydroxymethyl)-3-(1h-indol-3-yl)-n-(1-phenylethyl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(CO)(NCC=1OC2=CC=CC=C2C=1)C(=O)NC(C)C1=CC=CC=C1 NIFMQNFZDATVNO-UHFFFAOYSA-N 0.000 claims description 3
VNUIZIRGAROHHL-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylcarbamoylamino)-2-(1h-indol-3-ylmethyl)-3-methoxy-n-(1-phenylethyl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(COC)(NC(=O)NCC=1OC2=CC=CC=C2C=1)C(=O)NC(C)C1=CC=CC=C1 VNUIZIRGAROHHL-UHFFFAOYSA-N 0.000 claims description 3
230000003042 antagnostic effect Effects 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
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125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
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ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Otolaryngology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Immunology (AREA)
Hospice & Palliative Care (AREA)
Epidemiology (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Psychology (AREA)
Child & Adolescent Psychology (AREA)
Obesity (AREA)
Diabetes (AREA)
Orthopedic Medicine & Surgery (AREA)
Reproductive Health (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Physical Education & Sports Medicine (AREA)

CA002399584A 1999-12-22 2000-12-21 Non peptide tachykinin receptor antagonists Abandoned CA2399584A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US17154099P	1999-12-22	1999-12-22
US60/171,540		1999-12-22
EP00103665A EP1127875A1 (en)	2000-02-22	2000-02-22	Process for the preparation of alpha-dimethylaminomethyl-tryptophan methyl ester
EP00103665.6		2000-02-22
PCT/EP2000/013349 WO2001046176A2 (en)	1999-12-22	2000-12-21	Non peptide tachykinin receptor antagonists

Publications (1)

Publication Number	Publication Date
CA2399584A1 true CA2399584A1 (en)	2001-06-28

Family

ID=26070578

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002399584A Abandoned CA2399584A1 (en)	1999-12-22	2000-12-21	Non peptide tachykinin receptor antagonists

Country Status (18)

Country	Link
EP (1)	EP1244653A1 (zh)
JP (1)	JP2003518111A (zh)
KR (1)	KR20020062364A (zh)
CN (1)	CN1413206A (zh)
AP (1)	AP2002002556A0 (zh)
AU (1)	AU2370801A (zh)
BG (1)	BG106804A (zh)
BR (1)	BR0016626A (zh)
CA (1)	CA2399584A1 (zh)
IL (1)	IL150203A0 (zh)
IS (1)	IS6395A (zh)
MA (1)	MA26854A1 (zh)
MX (1)	MXPA02006282A (zh)
NO (1)	NO20022942L (zh)
OA (1)	OA12129A (zh)
PL (1)	PL357650A1 (zh)
SK (1)	SK8862002A3 (zh)
WO (1)	WO2001046176A2 (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010516731A (ja)	2007-01-24	2010-05-20	グラクソグループリミテッド	２−メトキシ−５−（５−トリフルオロメチル−テトラゾール−１−イル）−ベンジル］−（２ｓ−フェニル−ピペリジン−３ｓ−イル）−アミンを含む医薬組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0655055B1 (en) *	1992-08-13	2000-11-29	Warner-Lambert Company	Tachykinin antagonists
CA2355137A1 (en) *	1998-12-18	2000-06-29	Martyn Clive Pritchard	Non-peptide nk1 receptors antagonists

2000
- 2000-12-21 KR KR1020027008007A patent/KR20020062364A/ko not_active Application Discontinuation
- 2000-12-21 SK SK886-2002A patent/SK8862002A3/sk unknown
- 2000-12-21 OA OA1200200196A patent/OA12129A/en unknown
- 2000-12-21 BR BR0016626-0A patent/BR0016626A/pt not_active Application Discontinuation
- 2000-12-21 CA CA002399584A patent/CA2399584A1/en not_active Abandoned
- 2000-12-21 CN CN00817549A patent/CN1413206A/zh active Pending
- 2000-12-21 MX MXPA02006282A patent/MXPA02006282A/es unknown
- 2000-12-21 EP EP00987477A patent/EP1244653A1/en not_active Withdrawn
- 2000-12-21 WO PCT/EP2000/013349 patent/WO2001046176A2/en active Search and Examination
- 2000-12-21 IL IL15020300A patent/IL150203A0/xx unknown
- 2000-12-21 JP JP2001547086A patent/JP2003518111A/ja active Pending
- 2000-12-21 AP APAP/P/2002/002556A patent/AP2002002556A0/en unknown
- 2000-12-21 AU AU23708/01A patent/AU2370801A/en not_active Abandoned
- 2000-12-21 PL PL00357650A patent/PL357650A1/xx not_active Application Discontinuation
2002
- 2002-05-24 IS IS6395A patent/IS6395A/is unknown
- 2002-06-10 BG BG106804A patent/BG106804A/xx unknown
- 2002-06-14 MA MA26689A patent/MA26854A1/fr unknown
- 2002-06-19 NO NO20022942A patent/NO20022942L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
JP2003518111A (ja)	2003-06-03
OA12129A (en)	2006-05-05
WO2001046176A2 (en)	2001-06-28
KR20020062364A (ko)	2002-07-25
PL357650A1 (en)	2004-07-26
MA26854A1 (fr)	2004-12-20
WO2001046176A3 (en)	2002-07-04
IS6395A (is)	2002-05-24
SK8862002A3 (en)	2002-11-06
CN1413206A (zh)	2003-04-23
AP2002002556A0 (en)	2002-06-30
BG106804A (en)	2003-03-31
MXPA02006282A (es)	2004-09-06
NO20022942D0 (no)	2002-06-19
AU2370801A (en)	2001-07-03
NO20022942L (no)	2002-06-19
IL150203A0 (en)	2002-12-01
BR0016626A (pt)	2002-11-05
EP1244653A1 (en)	2002-10-02

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JP2001500850A (ja)	2001-01-23	非―ペプチドボンベシン受容体アンタゴニスト
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JPH07500604A (ja)	1995-01-19	高血圧治療用エチルアラニンアミノジオール化合物
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CZ289080B6 (cs)	2001-10-17	N-Substituovaný azabicykloheptanový derivát, způsob jeho výroby a pouľití
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Legal Events

Date	Code	Title	Description
2004-12-21	FZDE	Discontinued