SK402890A3 - Substance p analog - Google Patents

Substance p analog Download PDF

Info

Publication number: SK402890A3
Authority: SK; Slovakia
Prior art keywords: phe; leu; pro; gln; trp
Prior art date: 1989-08-16

Application number

SK4028-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK280796B6 (sk

Inventor

David H Coy

Jacques-Pierre Moreau

Original Assignee

Univ Tulane

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.)

1989-08-16

Filing date

1990-08-16

Publication date

2000-07-11

1990-08-16 Application filed by Univ Tulane filed Critical Univ Tulane

2000-07-11 Publication of SK280796B6 publication Critical patent/SK280796B6/sk

2000-07-11 Publication of SK402890A3 publication Critical patent/SK402890A3/sk

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ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical class 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 title description 4
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims abstract description 33
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/22—Tachykinins, e.g. Eledoisins, Substance P; Related peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK4028-90A 1989-08-16 1990-08-16 Substance p analog SK402890A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US39472789A	1989-08-16	1989-08-16

Publications (2)

Publication Number	Publication Date
SK280796B6 SK280796B6 (sk)	2000-07-11
SK402890A3 true SK402890A3 (en)	2000-07-11

Family

ID=23560172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK4028-90A SK402890A3 (en)	1989-08-16	1990-08-16	Substance p analog

Country Status (15)

Country	Link
EP (1)	EP0438566B1 (de)
JP (1)	JPH04502922A (de)
AT (1)	ATE143372T1 (de)
CA (1)	CA2039175A1 (de)
CZ (2)	CZ285562B6 (de)
DD (1)	DD298411A5 (de)
DE (1)	DE69028692T2 (de)
DK (1)	DK0438566T3 (de)
ES (1)	ES2094160T3 (de)
GR (1)	GR900100613A (de)
HU (1)	HUT65465A (de)
IE (1)	IE77033B1 (de)
PT (1)	PT95016B (de)
SK (1)	SK402890A3 (de)
WO (1)	WO1991002745A1 (de)

Families Citing this family (12)

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Publication number	Priority date	Publication date	Assignee	Title
US5410019A (en) *	1987-09-24	1995-04-25	The Administrators Of The Tulane-Educational Fund	Therapeutic peptides
FR2680174A1 (fr) *	1991-08-05	1993-02-12	Michelot Robert	Nouveaux composes peptidiques, inhibiteurs de l'adsorption du virus hiv sur ses cellules cibles.
EP1082959A1 (de)	1991-09-20	2001-03-14	Glaxo Group Limited	NK1 Antagonisten zur Behandlung von Depression
US6156725A (en) *	1996-08-16	2000-12-05	National Institute Of Immunology	Drug for the treatment of cancer
US6492330B1 (en)	1996-08-16	2002-12-10	National Institute Of Immunology	Antiangiogenic drugs
EP0835662B1 (de) *	1996-10-08	2001-11-14	National Institute of Immunology	Arzneimittel zur Behandlung von Krebs
CA2225185A1 (en)	1997-08-11	1999-02-11	Peter K. Law	Myoblast transfer therapy for relieving pain and for treating behavioral and perceptive abnormalities
US6316414B1 (en)	2000-07-31	2001-11-13	Dabur Research Foundation	Somatostatin analogs for the treatment of cancer
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
JP5707101B2 (ja) *	2009-11-11	2015-04-22	国立大学法人山口大学	消化器疾患治療剤
US9446029B2 (en)	2010-07-27	2016-09-20	Colorado State University Research Foundation	Use of NK-1 receptor antagonists in management of visceral pain
WO2023139542A1 (en) *	2022-01-21	2023-07-27	Institut Pasteur De Montevideo	Active immunization for reducing osteoarthritic, neuropathic, and cancer pain

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Publication number	Priority date	Publication date	Assignee	Title
US3862114A (en) *	1971-11-22	1975-01-21	Ici Australia Ltd	Analogs of substance p
IT1212508B (it) *	1981-12-22	1989-11-22	Anic Spa	Analoghi retro - invertiti dei penta - ed esapeptidi c - terminali della sostanza p. utili come vasodilatatori
US4481139A (en) *	1983-04-13	1984-11-06	Board Of Regents, The University Of Texas System	Peptide antagonists of substance P
US4803261A (en) *	1986-06-27	1989-02-07	The Administrators Of The Tulane Educational Fund	Method for synthesizing a peptide containing a non-peptide
NZ229552A (en) *	1988-06-20	1992-06-25	Merrell Dow Pharma	Neurokinin a antagonists

1990
- 1990-08-15 IE IE295890A patent/IE77033B1/en not_active IP Right Cessation
- 1990-08-16 SK SK4028-90A patent/SK402890A3/sk unknown
- 1990-08-16 CA CA002039175A patent/CA2039175A1/en not_active Abandoned
- 1990-08-16 CZ CZ99774A patent/CZ285562B6/cs not_active IP Right Cessation
- 1990-08-16 JP JP2511667A patent/JPH04502922A/ja active Pending
- 1990-08-16 PT PT95016A patent/PT95016B/pt not_active IP Right Cessation
- 1990-08-16 DK DK90912128.7T patent/DK0438566T3/da active
- 1990-08-16 ES ES90912128T patent/ES2094160T3/es not_active Expired - Lifetime
- 1990-08-16 HU HU906872A patent/HUT65465A/hu unknown
- 1990-08-16 DD DD90343501A patent/DD298411A5/de not_active IP Right Cessation
- 1990-08-16 EP EP90912128A patent/EP0438566B1/de not_active Expired - Lifetime
- 1990-08-16 GR GR900100613A patent/GR900100613A/el unknown
- 1990-08-16 DE DE69028692T patent/DE69028692T2/de not_active Expired - Fee Related
- 1990-08-16 AT AT90912128T patent/ATE143372T1/de not_active IP Right Cessation
- 1990-08-16 CZ CS904028A patent/CZ285319B6/cs not_active IP Right Cessation
- 1990-08-16 WO PCT/US1990/004633 patent/WO1991002745A1/en not_active Ceased

Also Published As

Publication number	Publication date
CZ285319B6 (cs)	1999-07-14
IE902958A1 (en)	1991-02-27
DD298411A5 (de)	1992-02-20
SK280796B6 (sk)	2000-07-11
PT95016B (pt)	1997-05-28
CZ285562B6 (cs)	1999-09-15
EP0438566B1 (de)	1996-09-25
HUT65465A (en)	1994-06-28
HU906872D0 (en)	1991-07-29
JPH04502922A (ja)	1992-05-28
ATE143372T1 (de)	1996-10-15
WO1991002745A1 (en)	1991-03-07
DE69028692D1 (de)	1996-10-31
EP0438566A4 (en)	1993-03-31
DK0438566T3 (da)	1996-11-11
EP0438566A1 (de)	1991-07-31
IE77033B1 (en)	1997-11-19
ES2094160T3 (es)	1997-01-16
GR900100613A (el)	1991-12-30
PT95016A (pt)	1991-04-18
CZ402890A3 (cs)	1999-04-14
DE69028692T2 (de)	1997-02-20
CA2039175A1 (en)	1991-02-17

Publication	Publication Date	Title
EP0489089B1 (de)	1996-06-19	Heilmittelpeptide
US5877277A (en)	1999-03-02	Octapeptide bombesin analogs
US5410019A (en)	1995-04-25	Therapeutic peptides
US5552520A (en)	1996-09-03	Therapeutic peptide derivatives
FI104252B (fi)	1999-12-15	Menetelmä terapeuttisesti käyttökelpoisten peptidien kemialliseksi syntetisoimiseksi kiinteässä faasissa
RU2212247C2 (ru)	2003-09-20	Аналоги пептида лг-рф, их применение и содержащие их фармацевтические композиции
US5175146A (en)	1992-12-29	Synthetic calcitonin peptides
US5106834A (en)	1992-04-21	Linear free-sulfhydryl-containing oligopeptide derivatives as antihypertensive agents
SK280796B6 (sk)	2000-07-11	Analóg substancie p
US5736517A (en)	1998-04-07	Treatment of cancer with peptides
JP2927936B2 (ja)	1999-07-28	ペプチド類
JPH05506862A (ja)	1993-10-07	環状および鎖状の治療用ペプチド
JP3514754B2 (ja)	2004-03-31	肝臓癌の治療
US4826813A (en)	1989-05-02	4'-Methyl-β-mercapto-β,β-cyclopentamethylenepropionic acid vasopressin antagonists
RU2088592C1 (ru)	1997-08-27	Терапевтические пептиды или их фармацевтически приемлемые соли
HU211513A9 (hu)	1995-11-28	Az átmeneti oltalom az 1-9. igénypontokra vonatkozik