ATE92079T1 - Zyklische pentapeptide als endothelinantagonisten. - Google Patents

Zyklische pentapeptide als endothelinantagonisten.

Info

Publication number: ATE92079T1
Authority: AT; Austria
Prior art keywords: group; alpha; dtrp; met; cho
Prior art date: 1989-12-28

Application number

AT90124947T

Other languages

English (en)

Inventor

Ishikawa Kiyofumi

Fukami Takehiro

Hayama Takashi

Niiyama Kenji

Nagase Toshio

Mase Toshiaki

Fujita Kagari

Nishikibe Masaru

Ihara Masaki

Yano Mitsuo

Original Assignee

Banyu Pharma Co Ltd

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.)

1989-12-28

Filing date

1990-12-20

Publication date

1993-08-15

1990-12-20 Application filed by Banyu Pharma Co Ltd filed Critical Banyu Pharma Co Ltd

1993-08-15 Application granted granted Critical

1993-08-15 Publication of ATE92079T1 publication Critical patent/ATE92079T1/de

Links

102000002045 Endothelin Human genes 0.000 title 1
108050009340 Endothelin Proteins 0.000 title 1
239000005557 antagonist Substances 0.000 title 1
ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 title 1
-1 alpha Aba Chemical compound 0.000 abstract 4
QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 abstract 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 abstract 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 abstract 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 abstract 1
125000002237 D-aspartyl group Chemical group [H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])C(*)=O 0.000 abstract 1
125000000028 D-cysteine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C(S[H])([H])[H] 0.000 abstract 1
125000004077 D-glutamic acid group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 abstract 1
125000000249 D-isoleucyl group Chemical group N[C@@H](C(=O)*)[C@@H](CC)C 0.000 abstract 1
125000003301 D-leucyl group Chemical group N[C@@H](C(=O)*)CC(C)C 0.000 abstract 1
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract 1
125000000197 D-threonyl group Chemical group N[C@@H](C(=O)*)[C@H](C)O 0.000 abstract 1
OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 abstract 1
125000003625 D-valyl group Chemical group N[C@@H](C(=O)*)C(C)C 0.000 abstract 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
QEFRNWWLZKMPFJ-YGVKFDHGSA-N L-methionine S-oxide Chemical compound CS(=O)CC[C@H](N)C(O)=O QEFRNWWLZKMPFJ-YGVKFDHGSA-N 0.000 abstract 1
125000000539 amino acid group Chemical group 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
IJVMOGKBEVRBPP-ZETCQYMHSA-N dcpg Chemical compound OC(=O)[C@@H](N)C1=CC=C(C(O)=O)C(C(O)=O)=C1 IJVMOGKBEVRBPP-ZETCQYMHSA-N 0.000 abstract 1
125000002883 imidazolyl group Chemical group 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1

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
- C07K7/64—Cyclic peptides containing only normal peptide links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/57536—Endothelin, vasoactive intestinal contractor [VIC]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/80—Antihypertensive peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Genetics & Genomics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Zoology (AREA)
Endocrinology (AREA)
Toxicology (AREA)
Gastroenterology & Hepatology (AREA)
Vascular Medicine (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

AT90124947T 1989-12-28 1990-12-20 Zyklische pentapeptide als endothelinantagonisten. ATE92079T1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP34269589		1989-12-28
JP18586790		1990-07-13

Publications (1)

Publication Number	Publication Date
ATE92079T1 true ATE92079T1 (de)	1993-08-15

Family

ID=26503375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT90124947T ATE92079T1 (de)	1989-12-28	1990-12-20	Zyklische pentapeptide als endothelinantagonisten.

Country Status (8)

Country	Link
US (1)	US5114918A (de)
EP (1)	EP0436189B1 (de)
KR (1)	KR0145317B1 (de)
AT (1)	ATE92079T1 (de)
AU (1)	AU632193B2 (de)
CA (1)	CA2032559C (de)
DE (2)	DE436189T1 (de)
ES (1)	ES2041611T3 (de)

Families Citing this family (81)

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US5591761A (en) *	1993-05-20	1997-01-07	Texas Biotechnology Corporation	Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
US5962490A (en)	1987-09-25	1999-10-05	Texas Biotechnology Corporation	Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
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CA2043741C (en) *	1990-06-07	2003-04-01	Kiyofumi Ishikawa	Endothelin antagonistic peptide derivatives
US5496928A (en) *	1990-06-07	1996-03-05	Banyu Pharmaceutical Co., Ltd.	Endothelin antagonistic substance
US5736509A (en) *	1990-12-14	1998-04-07	Texas Biotechnology Corporation	Cyclic peptide surface feature mimics of endothelin
US5331573A (en) *	1990-12-14	1994-07-19	Balaji Vitukudi N	Method of design of compounds that mimic conformational features of selected peptides
DE69212011T2 (de) *	1991-02-15	1997-01-09	Takeda Chemical Industries Ltd	Endothelin Antagoniste
EP0574530A4 (en) *	1991-03-08	1996-04-03	Res Corp Technologies Inc	Endothelin antagonists
US5382569A (en) *	1991-05-16	1995-01-17	Warner-Lambert Company	Endotherlin antagonists
US5260276A (en) *	1991-06-14	1993-11-09	Warner-Lambert Company	Linear and monocyclic endothelin antagonists
CA2072934C (en) *	1991-07-19	2007-08-28	Karl William Aston	Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide
ATE155486T1 (de) *	1991-08-13	1997-08-15	Takeda Chemical Industries Ltd	Zyklische peptide und ihre verwendung
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WO1993013218A1 (fr) *	1991-12-27	1993-07-08	Kyowa Hakko Kogyo Co., Ltd.	Peptide antagoniste de l'endotheline
WO1993017701A1 (en) *	1992-03-12	1993-09-16	The Administrators Of The Tulane Educational Fund	Endothelin receptor-binding peptides
WO1993023404A1 (en) *	1992-05-19	1993-11-25	Immunopharmaceutics, Inc.	Compounds that modulate endothelin activity
WO1993025580A1 (en) *	1992-06-18	1993-12-23	Immunopharmaceutics, Inc.	Cyclic peptides that modulate endothelin activity
WO1994003483A1 (en) *	1992-07-30	1994-02-17	Chiron Corporation	Endothelin receptor-binding compounds
US5922681A (en) *	1992-09-14	1999-07-13	Warner-Lambert Company	Endothelin antagonists
EP0606881B1 (de) *	1993-01-13	1999-05-12	Takeda Chemical Industries, Ltd.	Cyclische Pentapeptide mit Beta-Turn und Gamma-Turn
US6204259B1 (en)	1993-01-14	2001-03-20	Monsanto Company	Manganese complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide
US5352800A (en) *	1993-03-11	1994-10-04	Merck & Co., Inc.	Process for the production of a novel endothelin antagonist
US5334598A (en) *	1993-03-19	1994-08-02	Merck & Co., Inc.	Six-membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives
US5767310A (en) *	1993-03-19	1998-06-16	Merck & Co., Inc.	Phenoxyphenylacetic acid derivatives
US5565485A (en) *	1993-03-19	1996-10-15	Merck & Co., Inc.	Biphenyl compounds useful or endothelin antagonists
US5420133A (en) *	1993-03-19	1995-05-30	Merck & Co., Inc.	Quinazolinones substituted with phenoxyphenylacetic acid derivatives
US5374638A (en) *	1993-03-19	1994-12-20	Merck & Co., Inc.	Six membered ring fused imidazoles substituted with phenoxyphenylacetic acid derivatives used to treat asthma
US5401745A (en) *	1993-03-19	1995-03-28	Merck & Co., Inc.	Quinazolinones substituted with phenoxyphenylacetic acid derivatives
FI941826L (fi)	1993-04-21	1994-10-22	Takeda Chemical Industries Ltd	Menetelmät ja koostumukset elimen hypofunktion ennaltaehkäisemiseksi ja/tai terapeuttiseksi hoitamiseksi
US6342610B2 (en)	1993-05-20	2002-01-29	Texas Biotechnology Corp.	N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
US6613804B2 (en)	1993-05-20	2003-09-02	Encysive Pharmaceuticals, Inc.	Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
US6030991A (en) *	1993-05-20	2000-02-29	Texas Biotechnology Corp.	Benzenesulfonamides and the use thereof to modulate the activity of endothelin
AU673731B2 (en) *	1993-06-03	1996-11-21	Banyu Pharmaceutical Co., Ltd.	Novel endothelin antagonistic peptide
US6087324A (en) *	1993-06-24	2000-07-11	Takeda Chemical Industries, Ltd.	Sustained-release preparation
EP0788370A4 (de)	1993-07-09	1998-07-08	Smithkline Beecham Corp	Zyklische, teilzufallige peptidbibliotheken
US5391566A (en) *	1993-07-20	1995-02-21	Merck & Co., Inc.	Benzimidazolinones substituted with phenoxyphenylacetic acid derivatives
US5686478A (en) *	1993-07-20	1997-11-11	Merck & Co. Inc.	Endothelin antagonists
SK20396A3 (en) *	1993-08-19	1997-03-05	Warner Lambert Co	Substituted 2(5h)furanone, 2(5h)thiophenone or 2(5h)pyrrolone derivatives and pharmaceutical compositions on their base
US5492917A (en) *	1993-09-29	1996-02-20	Merck & Co., Inc.	Endothelin antagonists incorporating a cyclobutane
US5780498A (en) *	1993-11-01	1998-07-14	Ciba-Geigy Japan Limited	Endothelin receptor antagonists
CA2135151A1 (en) *	1993-11-08	1995-05-09	Mitsuhiro Wakimasu	Cyclic hexapeptides, their production and use
US6346604B1 (en)	1995-10-31	2002-02-12	Takeda Chemical Industries, Inc.	Method for controlling conformation of cyclopentapeptide
US5620953A (en) *	1994-07-27	1997-04-15	Merck & Co., Inc.	Antiprotozoal cyclic tetrapeptides
US5610177A (en) *	1994-08-08	1997-03-11	Warner-Lambert Company	Acylated amino acids as endothelin antagonists
US5538991A (en) *	1994-09-14	1996-07-23	Merck & Co., Inc.	Endothelin antagonists bearing 5-membered heterocyclic amides
US5559135A (en) *	1994-09-14	1996-09-24	Merck & Co., Inc.	Endothelin antagonists bearing pyridyl amides
US5482960A (en) *	1994-11-14	1996-01-09	Warner-Lambert Company	Nonpeptide endothelin antagonists
US5658902A (en) *	1994-12-22	1997-08-19	Warner-Lambert Company	Quinazolines as inhibitors of endothelin converting enzyme
US5599811A (en) *	1995-02-21	1997-02-04	Warner-Lambert Company	Benzothiazine dioxides as endothelin antagonists
US5573762A (en) *	1995-04-24	1996-11-12	Genentech, Inc.	Use of leukemia inhibitory factor specific antibodies and endothelin antagonists for treatment of cardiac hypertrophy
CN1183104A (zh) *	1995-04-28	1998-05-27	武田药品工业株式会社	Lh－rh受体拮抗剂
US6525041B1 (en)	1995-06-06	2003-02-25	Pharmacia Corporation	Manganese or iron complexes of nitrogen-containing macrocyclic ligands effective as catalysts for dismutating superoxide
US5922759A (en) *	1996-06-21	1999-07-13	Warner-Lambert Company	Butenolide endothelin antagonists
US5998468A (en) *	1995-08-24	1999-12-07	Warner-Lambert Company	Furanone endothelin antagonists
CA2192782C (en)	1995-12-15	2008-10-14	Nobuyuki Takechi	Production of microspheres
US5977117A (en) *	1996-01-05	1999-11-02	Texas Biotechnology Corporation	Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin
US5958905A (en)	1996-03-26	1999-09-28	Texas Biotechnology Corporation	Phosphoramidates, phosphinic amides and related compounds and the use thereof to modulate the activity of endothelin
US6133263A (en) *	1996-04-10	2000-10-17	Warner-Lambert Company	Endothelin antagonists with ether-linked groups
US5804585A (en)	1996-04-15	1998-09-08	Texas Biotechnology Corporation	Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin
US5891892A (en) *	1996-10-29	1999-04-06	Warner-Lambert Company	Small molecule biaryl compounds as inhibitors of endothelin converting enzyme
US5783705A (en)	1997-04-28	1998-07-21	Texas Biotechnology Corporation	Process of preparing alkali metal salys of hydrophobic sulfonamides
JP3455233B2 (ja)	1997-04-28	2003-10-14	テキサス・バイオテクノロジー・コーポレイシヨン	エンドテリン介在障害治療用のスルホンアミド類
US6608027B1 (en)	1999-04-06	2003-08-19	Boehringer Ingelheim (Canada) Ltd	Macrocyclic peptides active against the hepatitis C virus
US7566452B1 (en)	1999-05-04	2009-07-28	New York University	Cancer treatment with endothelin receptor antagonists
MXPA02006461A (es)	1999-12-31	2003-09-05	Texas Biotechnology Corp	Sulfonamidas y derivados de las mismas que modulan la actividad de endotelina.
CA2430934C (en)	2000-12-01	2011-06-21	Takeda Chemical Industries, Ltd.	A method of producing sustained-release preparations of a bioactive substance using high-pressure gas
KR20050111306A (ko)	2002-11-19	2005-11-24	아칠리온 파르마세우티칼스 인코포레이티드	바이러스 복제 억제제로서의 치환된 아릴 티오우레아 및관련 화합물
ES2361997T3 (es) *	2003-09-22	2011-06-27	Boehringer Ingelheim International Gmbh	Péptidos macrocíclicos activos contra el virus de la hepatitis c.
GB0326632D0 (en)	2003-11-14	2003-12-17	Jagotec Ag	Dry powder formulations
ATE495185T1 (de) *	2004-01-21	2011-01-15	Boehringer Ingelheim Int	Makrocyclische peptide mit wirkung gegen das hepatitis-c-virus
CA2644784A1 (en) *	2006-03-13	2007-09-20	Jinling Chen	Formulations of sitaxsentan sodium
JP2009530284A (ja) *	2006-03-13	2009-08-27	エンサイシブ・ファーマシューティカルズ・インコーポレイテッド	拡張期心不全を治療するための方法と組成物
WO2007109620A2 (en) *	2006-03-17	2007-09-27	San Diego State University Foundation	Macrocyclic peptides and methods for making and using them
US20080026061A1 (en) *	2006-06-22	2008-01-31	Reichwein John F	Crystalline N-(4-chloro-3-methyl-5-isoxazolyl)-2-[2-methyl-4.5-(methylenedioxy)phenylacetyl]-thiophene-3-sulfonamide
WO2009033665A2 (en) *	2007-09-11	2009-03-19	Mondobiotech Laboratories Ag	Use of a rgd-peptide and/or parathyroid hormone (1-34 ) as anti-hiv agent
US20130177651A1 (en)	2010-09-03	2013-07-11	Pharmaterials Limited	Pharmaceutical Composition Suitable for Use in a Dry Powder Inhaler
JP6224586B2 (ja)	2012-07-10	2017-11-01	武田薬品工業株式会社	注射用製剤
CN113286576B (zh) *	2019-01-04	2024-05-14	雅芳产品公司	Gdf-11片段的氧化衍生物

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4505897A (en) *	1983-04-18	1985-03-19	The Administrators Of The Tulane Educational Fund	Cyclic pentapeptides displaying somatostatin antagonism and method of treatment of mammals therewith
DE3401545A1 (de) *	1983-08-03	1985-02-14	Hoechst Ag, 6230 Frankfurt	Neue peptide mit immunstimulierender wirkung, verfahren zu deren herstellung und deren verwendung
DE3881467T2 (de) *	1987-10-09	1993-10-21	Agency Ind Science Techn	Vasokonstriktor-Peptid.

1990
- 1990-12-18 CA CA002032559A patent/CA2032559C/en not_active Expired - Lifetime
- 1990-12-19 AU AU68285/90A patent/AU632193B2/en not_active Expired
- 1990-12-20 DE DE199090124947T patent/DE436189T1/de active Pending
- 1990-12-20 ES ES90124947T patent/ES2041611T3/es not_active Expired - Lifetime
- 1990-12-20 US US07/630,505 patent/US5114918A/en not_active Expired - Lifetime
- 1990-12-20 AT AT90124947T patent/ATE92079T1/de not_active IP Right Cessation
- 1990-12-20 EP EP90124947A patent/EP0436189B1/de not_active Expired - Lifetime
- 1990-12-20 DE DE90124947T patent/DE69002448T2/de not_active Expired - Lifetime
- 1990-12-28 KR KR1019900022235A patent/KR0145317B1/ko not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU6828590A (en)	1991-07-11
CA2032559C (en)	2001-11-06
EP0436189B1 (de)	1993-07-28
DE69002448T2 (de)	1994-03-17
KR0145317B1 (ko)	1998-07-01
EP0436189A1 (de)	1991-07-10
US5114918A (en)	1992-05-19
ES2041611T3 (es)	1994-11-16
AU632193B2 (en)	1992-12-17
KR910011899A (ko)	1991-07-30
CA2032559A1 (en)	1991-06-29
DE69002448D1 (de)	1993-09-02
DE436189T1 (de)	1992-09-24
ES2041611T1 (es)	1993-12-01

Legal Events

Date	Code	Title	Description
2011-03-15	EELA	Cancelled due to lapse of time

Publication	Publication Date	Title
ATE92079T1 (de)	1993-08-15	Zyklische pentapeptide als endothelinantagonisten.
KR0139632B1 (ko)	1998-07-01	브라디키닌 길항 작용을 갖는 펩티드
Manning et al.	1982	Design of more potent and selective antagonists of the antidiuretic responses to arginine-vasopressin devoid of antidiuretic agonism
JPS6434997A (en)	1989-02-06	Peptide, manufacture, lhrh antagonistic medicine and manufacture
FI842166A0 (fi)	1984-05-30	Bukspottskoertelns grf hos maenniskan.
KR850008681A (ko)	1985-12-21	합성펩티드의 제조방법
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