SK8862002A3 - Non peptide tachykinin receptor antagonists - Google Patents

Non peptide tachykinin receptor antagonists Download PDF

Info

Publication number: SK8862002A3
Authority: SK; Slovakia
Prior art keywords: ylmethyl; phenyl; alkyl; benzofuran; indol
Prior art date: 1999-12-22

Application number

SK886-2002A

Other languages

English (en)

Slovak (sk)

Inventor

David Christopher Horwell

Russell Andrew Lewthwaite

Martin Clive Pritchard

Jennifer Raphy

Hubert Barth

Klaus Steiner

Bernd Schiefermayr

Original Assignee

Warner Lambert Co

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

2002-11-06

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

2000-12-21 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2002-11-06 Publication of SK8862002A3 publication Critical patent/SK8862002A3/sk

Links

239000002462 tachykinin receptor antagonist Substances 0.000 title abstract description 7
108090000765 processed proteins & peptides Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 102
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206010029113 Neovascularisation Diseases 0.000 claims abstract description 11
230000001594 aberrant effect Effects 0.000 claims abstract description 11
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
239000003795 chemical substances by application Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 62
-1 benzo [1,3] dioxolyl Chemical group 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 49
238000000034 method Methods 0.000 claims description 39
229910052757 nitrogen Inorganic materials 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 29
229910052717 sulfur Inorganic materials 0.000 claims description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
208000035475 disorder Diseases 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
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000002541 furyl group Chemical group 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 18
125000001544 thienyl group Chemical group 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000001041 indolyl group Chemical group 0.000 claims description 16
108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 15
102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 15
208000026935 allergic disease Diseases 0.000 claims description 15
208000019901 Anxiety disease Diseases 0.000 claims description 14
230000036506 anxiety Effects 0.000 claims description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
208000011231 Crohn disease Diseases 0.000 claims description 12
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
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 10
229910052731 fluorine Inorganic materials 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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230000002757 inflammatory effect Effects 0.000 claims description 9
125000005956 isoquinolyl group Chemical group 0.000 claims description 9
125000000168 pyrrolyl group Chemical group 0.000 claims description 9
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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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UZZHXUNNVKMDTG-OAHLLOKOSA-N methyl (2r)-2-amino-2-[(dimethylamino)methyl]-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@@](N)(CN(C)C)C(=O)OC)=CNC2=C1 UZZHXUNNVKMDTG-OAHLLOKOSA-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 7
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
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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
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 5
239000003085 diluting agent Substances 0.000 claims description 5
VVDUZZGYBOWDSQ-UHFFFAOYSA-M eschenmoser's salt Chemical compound [I-].C[N+](C)=C VVDUZZGYBOWDSQ-UHFFFAOYSA-M 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
OOLYAWMRXNHWHP-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylamino)-2-(1h-indol-3-ylmethyl)-3-methoxy-n-(1-phenylethyl)propanamide Chemical compound C=1NC2=CC=CC=C2C=1CC(COC)(NCC=1OC2=CC=CC=C2C=1)C(=O)NC(C)C1=CC=CC=C1 OOLYAWMRXNHWHP-UHFFFAOYSA-N 0.000 claims description 4
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125000000753 cycloalkyl group Chemical group 0.000 claims description 4
238000003384 imaging method Methods 0.000 claims description 4
238000001727 in vivo Methods 0.000 claims description 4
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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208000011117 substance-related disease Diseases 0.000 claims description 4
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125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
208000024891 symptom Diseases 0.000 claims description 3
230000003533 narcotic effect Effects 0.000 claims description 2
LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
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 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000003623 enhancer Substances 0.000 claims 1
230000010261 cell growth Effects 0.000 abstract 1
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
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239000012267 brine Substances 0.000 description 18
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Classifications

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- 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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Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pulmonology (AREA)
Otolaryngology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (AREA)
Dermatology (AREA)
Immunology (AREA)
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Reproductive Health (AREA)
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SK886-2002A 1999-12-22 2000-12-21 Non peptide tachykinin receptor antagonists SK8862002A3 (en)

Applications Claiming Priority (3)

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

Publications (1)

Publication Number	Publication Date
SK8862002A3 true SK8862002A3 (en)	2002-11-06

Family

ID=26070578

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK886-2002A SK8862002A3 (en)	1999-12-22	2000-12-21	Non peptide tachykinin receptor antagonists

Country Status (18)

Country	Link
EP (1)	EP1244653A1 (is)
JP (1)	JP2003518111A (is)
KR (1)	KR20020062364A (is)
CN (1)	CN1413206A (is)
AP (1)	AP2002002556A0 (is)
AU (1)	AU2370801A (is)
BG (1)	BG106804A (is)
BR (1)	BR0016626A (is)
CA (1)	CA2399584A1 (is)
IL (1)	IL150203A0 (is)
IS (1)	IS6395A (is)
MA (1)	MA26854A1 (is)
MX (1)	MXPA02006282A (is)
NO (1)	NO20022942D0 (is)
OA (1)	OA12129A (is)
PL (1)	PL357650A1 (is)
SK (1)	SK8862002A3 (is)
WO (1)	WO2001046176A2 (is)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008090114A1 (en)	2007-01-24	2008-07-31	Glaxo Group Limited	Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-)

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
EP1140914A1 (en) *	1998-12-18	2001-10-10	Warner-Lambert Company	Non-peptide nk1 receptors antagonists

2000
- 2000-12-21 WO PCT/EP2000/013349 patent/WO2001046176A2/en not_active Ceased
- 2000-12-21 CA CA002399584A patent/CA2399584A1/en not_active Abandoned
- 2000-12-21 KR KR1020027008007A patent/KR20020062364A/ko not_active Withdrawn
- 2000-12-21 OA OA1200200196A patent/OA12129A/en unknown
- 2000-12-21 MX MXPA02006282A patent/MXPA02006282A/es unknown
- 2000-12-21 EP EP00987477A patent/EP1244653A1/en not_active Withdrawn
- 2000-12-21 AP APAP/P/2002/002556A patent/AP2002002556A0/en unknown
- 2000-12-21 IL IL15020300A patent/IL150203A0/xx unknown
- 2000-12-21 AU AU23708/01A patent/AU2370801A/en not_active Abandoned
- 2000-12-21 JP JP2001547086A patent/JP2003518111A/ja active Pending
- 2000-12-21 PL PL00357650A patent/PL357650A1/xx not_active Application Discontinuation
- 2000-12-21 SK SK886-2002A patent/SK8862002A3/sk unknown
- 2000-12-21 BR BR0016626-0A patent/BR0016626A/pt not_active Application Discontinuation
- 2000-12-21 CN CN00817549A patent/CN1413206A/zh active Pending
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/NO20022942D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2001046176A2 (en)	2001-06-28
NO20022942L (no)	2002-06-19
JP2003518111A (ja)	2003-06-03
BR0016626A (pt)	2002-11-05
OA12129A (en)	2006-05-05
CA2399584A1 (en)	2001-06-28
KR20020062364A (ko)	2002-07-25
PL357650A1 (en)	2004-07-26
CN1413206A (zh)	2003-04-23
WO2001046176A3 (en)	2002-07-04
AP2002002556A0 (en)	2002-06-30
IS6395A (is)	2002-05-24
BG106804A (en)	2003-03-31
NO20022942D0 (no)	2002-06-19
MXPA02006282A (es)	2004-09-06
IL150203A0 (en)	2002-12-01
MA26854A1 (fr)	2004-12-20
AU2370801A (en)	2001-07-03
EP1244653A1 (en)	2002-10-02

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