KR950701935A - 항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체(Conformationally restrained peptide analogs as antiplatelet agents) - Google Patents

항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체(Conformationally restrained peptide analogs as antiplatelet agents)

Info

Publication number
KR950701935A
KR950701935A KR1019940704404A KR19940704404A KR950701935A KR 950701935 A KR950701935 A KR 950701935A KR 1019940704404 A KR1019940704404 A KR 1019940704404A KR 19940704404 A KR19940704404 A KR 19940704404A KR 950701935 A KR950701935 A KR 950701935A
Authority
KR
South Korea
Prior art keywords
asp
benzyl
group
amino acid
bond
Prior art date
Application number
KR1019940704404A
Other languages
English (en)
Other versions
KR100297184B1 (ko
Inventor
엘. 하베손 스코트
제이. 비톤티 알란
Original Assignee
스티븐 엘. 네스비트
메렐 다우 파마슈티칼즈 인코포레이티드
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.)
Filing date
Publication date
Application filed by 스티븐 엘. 네스비트, 메렐 다우 파마슈티칼즈 인코포레이티드 filed Critical 스티븐 엘. 네스비트
Publication of KR950701935A publication Critical patent/KR950701935A/ko
Application granted granted Critical
Publication of KR100297184B1 publication Critical patent/KR100297184B1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10Tetrapeptides
    • C07K5/1002Tetrapeptides with the first amino acid being neutral
    • C07K5/1005Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/745Blood coagulation or fibrinolysis factors
    • C07K14/75Fibrinogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/021Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10Tetrapeptides
    • C07K5/1002Tetrapeptides with the first amino acid being neutral
    • C07K5/1005Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/101Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02Linear peptides containing at least one abnormal peptide link
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/50Cyclic peptides containing at least one abnormal peptide link
    • C07K7/54Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
    • C07K7/56Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Hematology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Zoology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Toxicology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
  • Measuring And Recording Apparatus For Diagnosis (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

본 발명은 혈소판 응집 억제제로서의 입테배좌적으로 억제된 (coformationally restrained) 펩타이드 동족체에 관한 것이다. 이들 화합물은 혈소판 응집을 억재하는 혈소판 GPⅡb-Ⅲa 인테그린(integrin) 수용체에 대한 피브리노겐의 결합을 억제하여 이들 화합물은 강력한 항혈전제로서 작용한다.

Description

항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체 (Conformationally restrained peptide analogs as antiplatelet agents)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (16)

  1. 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염.
    상기식에서, Y는 단편 -A1-A2-A3-NR1R2(여기서, A1은 결합이거나 Ser, Asp, Met, Trp, Phe 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, A2는 결합이거나 Pro, Nle, Met, Leu, Asn, Asp, Val, Arg 및 Leu로 이루어진 그룹에서 선택된 아미노산이며, A3는 결합이거나 Ala, Asp, Pro 및 Asn으로 이루어진 그룹에서 선택된 아미노산이고, R1및 R2는 각각 독립적으로 수소, C1-C10알킬, 벤질, 인돌릴, 피리디닐이거나 또는 Cl, Br, NO2, NH2, OH 및 OCH3로 이루어진 그룹에서 선택된 1 내지 3개의 치환cp로 임의 치환된 페닐이다)이며, Z는 단편 W-A6-A5-A4-(여기서, A4는 결합이거나 Gly및 βAla로 이루어진 그룹에서 선택된 아미노산이고, A5는 결합이거나 Arg, Lys, Thr, Ile, Leu, Asp, Asn 및 Val로 이루어진 그룹에서 선택된 아미노산이며, A6은 결합이거나 Val, Lys, Arg, Asp, Asn 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, W는 수소, 석시닐, C1-C10아실, C1-C10알킬, -(CH2)mC6H5(여기서, m은 정수 1 내지 3이다) 또는 -(CH2)pCO2H(여기서, p는 정수 1 내지 4이다)이다〕이며, X는 CONH, CH2NH, COCH2, CH2CH2, -CH20- 또는 -CH=CH-이고; R은 수소, C-C10알킬, 벤질 인돌릴, 나프틸, 티에닐, p-HO-벤질, p-NO2-벤질, p-Cl-벤질; 및 p-NH2-벤질이며, n은 정수 1 내지 3이고, 단 A6, A5및 A4중 하나가 아미노산인 경우 W는 C1-C10알킬, -(CH2)mC6H5또는 -(CH2)pCO2H가 아니다.
  2. 제1항에 있어서, X가 CONH, COCH2또는 CH2CH2인 화합물.
  3. 제1항에 있어서, Y가 벤질아민 또는 Asp-NH2인 화합물.
  4. 제1항에 있어서, n이 2인 화합물.
  5. 제1항에 있어서, R이 CH3, 벤질 또는 p-0H-벤질인 화합물.
  6. 제1항에 일어서, Z가 석시닐, -(CH2)3Co2H 또는 CH3CO-Asp-Gly인 화합물.
  7. 제1항에 있어서, X가 CONH, COCH2또는 CH2CH2이고; Y가 벤질아민 또는 Asp-NH2이며; n이 2이고; R이 CH3, 벤질 또는 p-OH-벤질이며; Z가 석시닐, -(CH2)3C02H 또는 CH3CO-Asp-Gly인 화합물.
  8. 제1항에 있어서, 사이클로〔Ala〔CH2NH〕-Arg-Gly-Asp-δ-Glu〕(NHBn) CF3CO2H인 화합물.
  9. 제1항에 있어서, 사이클로〔Ala〔CH2N(CO(CH2)2CO2H)-Arg-Gly-Asp-δ-Glu〕 (NHBn) ·CF3CO2H인 화합물.
  10. 제1항에 있어서, 사이클〔Ala〔CH2N(CO(CH2)3Ph)-Arg-Gly-Asp-δ-Glu〕 (NHBn)·CF3CO2H인 화합물.
  11. 제1항에 있어서, 사이클로〔Ala〔CH2N(CO(CH2)3CO2H)-Arg-Gly-Asp-δ-Glu〕 (NHBn) ·CF3CO2H인 화합물.
  12. 혈전 상태의 치료를 필요로 하는 환자에 대한 혈전 상태치료용 약제로서의, 제1항 내지 제11항중 어느 한 항에 따른 화합물의 용도.
  13. 약제로서의 제1항 내지 제11항중 어느 한 항에 따른 화합물의 용도.
  14. 제1항 내지 제11항중 어느 한 항에 따른 화합물을 불활성 담체와의 혼합물 형태로서 포함하는 조성물.
  15. 제14항에 있어서, 불활성 담체가 약제학적 담체인 조성물.
  16. 일반식(Ⅰ)화합물 또는 이의 약제학적으로 허용되는 염의 항혈소판 유효 투여량을 환자에게 투여함을 포함하여 혈전 상태의 치료를 필요로 하는 환자의 혈전 상태를 치료하는 방법.
    상기식에서, Y는 단편 -A1-A2-A3-NR1R2(여기서, A1은 결합이거나 Ser, Asp, Met, Trp, Phe 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, A2는 결합이거나 Pro, Nle, Met, Leu, Asn, Asp, Val, Arg 및 Leu로 이루어진 그룹에서 선택된 아미노산이며, A3는 결합이거나 Ala, Asp, Pro 및 Asn으로 이루어진 그룹에서 선택된 아미노산이고, R1및 R2는 각각 독립적으로 수소, C1-C10알킬, 벤질, 인돌릴, 피리디닐이거나 또는 Cl, Br, NO2, NH2, OH 및 OCH3로 이루어진 그룹에서 선택된 1 내지 3개의 치환체로 임의 치환된 페닐이다)이며, Z는 단편 W-A6-A5-A4-〔여기서, A4는 결합이거나 Gly및 βAla로 이루어진 그룹에서 선택된 아미노산이고, A5는 결합이거나 Arg, Lys, Thr, Ile, Leu, Asp, Asn 및 Val로 이루어진 그룹에서 선택된 아미노산이며, A6은 결합이거나 Val, Lys, Arg, Asp, Asn 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, W는 수소, 석시닐, C1-C10아실, C1-C10알킬, -(CH2)mC6H5(여기서, m은 정수 1 내지 3이다) 또는 -(CH2)pCO2H(여기서, p는 정수 1 내지 4이다)이다〕이며, X는 CONH, CH2NH, COCH2, CH2CH2, -CH20- 또는 -CH=CH-이고; R은 수소, C-C10알킬, 벤질 인돌릴, 나프틸, 티에닐, p-HO-벤질, p-NO2-벤질, p-Cl-벤질; 및 P-NH2-벤질이며, n은 정수 1 내지 3이고, 단 A6, A5및 A4중 하나가 아미노산인 경우 W는 C1-C10알킬, -(CH2)mC6H5또는 -(CH2)PCO2H가 아니다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940704404A 1992-06-04 1993-05-14 항혈소판제로서의입체배좌적으로억제된펩타이드동족체및이를포함하는약제학적조성물 KR100297184B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US89421492A 1992-06-04 1992-06-04
US07/894214 1992-06-04
US07/894,214 1992-06-04
US5611193A 1993-05-07 1993-05-07
US08/056,111 1993-05-07
US08/056111 1993-05-07
PCT/US1993/004660 WO1993024520A1 (en) 1992-06-04 1993-05-14 Conformationally restrained peptide analogs as antiplatelet agents

Publications (2)

Publication Number Publication Date
KR950701935A true KR950701935A (ko) 1995-05-17
KR100297184B1 KR100297184B1 (ko) 2001-10-22

Family

ID=26734982

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940704404A KR100297184B1 (ko) 1992-06-04 1993-05-14 항혈소판제로서의입체배좌적으로억제된펩타이드동족체및이를포함하는약제학적조성물

Country Status (16)

Country Link
US (1) US6107275A (ko)
EP (1) EP0648224B1 (ko)
JP (1) JP3398747B2 (ko)
KR (1) KR100297184B1 (ko)
AT (1) ATE168380T1 (ko)
AU (1) AU672010B2 (ko)
CA (1) CA2137072C (ko)
DE (1) DE69319733T2 (ko)
DK (1) DK0648224T3 (ko)
ES (1) ES2121088T3 (ko)
GR (1) GR3027738T3 (ko)
IL (1) IL105885A (ko)
MX (1) MX9303332A (ko)
NZ (1) NZ253452A (ko)
TW (1) TW274085B (ko)
WO (1) WO1993024520A1 (ko)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843156A (en) * 1988-08-24 1998-12-01 Endoluminal Therapeutics, Inc. Local polymeric gel cellular therapy
US6117974A (en) * 1991-10-02 2000-09-12 Peptor Limited Libraries of backbone-cyclized peptidomimetics
EP0729362B1 (en) * 1993-11-19 2000-01-12 G.D. SEARLE & CO. TRANSDERMAL COMPOSITION OF N- N- 5- 4-(AMINOIMINOMETHYL)PHENYL]-1-OXOPENTYL]-L-alpha-ASPARTYL]-L-PHENYLALANINE OR ITS ESTERS AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS
US6387880B1 (en) 1994-10-24 2002-05-14 G.D. Searle & Co. Transdermal N-[N-[5-[4-(aminoiminomethly)phenyl]-1-oxopentyl]-L-α-aspartyl]-L-phenylalainine or its esters and their pharmaceutically acceptable salts
DE19653036A1 (de) * 1996-12-19 1998-06-25 Merck Patent Gmbh Cyclopeptidderivate
DE19728524A1 (de) * 1997-07-04 1999-01-07 Merck Patent Gmbh Cyclische Azapeptide
CA2284459C (en) 1999-10-04 2012-12-11 Neokimia Inc. Combinatorial synthesis of libraries of macrocyclic compounds useful in drug discovery
CA2793838C (en) 2010-03-19 2019-09-17 H. Lee Moffitt Cancer Center & Research Institute, Inc. Integrin interaction inhibitors for the treatment of cancer
US10011635B2 (en) 2013-09-27 2018-07-03 H. Lee Moffitt Cancer Center And Research Institute, Inc. Cyclic peptide conjugates and methods of use

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1585061A (en) * 1977-03-15 1981-02-25 Nat Res Dev Synthesis of peptides
US5041380A (en) * 1982-08-04 1991-08-20 La Jolla Cancer Research Foundation Tetrapeptide
US5318899A (en) * 1989-06-16 1994-06-07 Cor Therapeutics, Inc. Platelet aggregation inhibitors
FI84025C (fi) * 1989-06-30 1991-10-10 Jukka Elias Saarikettu Filter som taol hoega temperaturer och foerfarande foer framstaellning daerav.
US5384309A (en) * 1989-07-17 1995-01-24 Genentech, Inc. Cyclized peptides and their use as platelet aggregation inhibitors
CA2021951A1 (en) * 1989-07-28 1991-01-29 Ruth F. Nutt Fibrinogen receptor antagonists
US5023233A (en) * 1989-07-28 1991-06-11 Merck & Co., Inc. Fibrinogen receptor antagonists
EP0410541A1 (en) * 1989-07-28 1991-01-30 Merck & Co. Inc. Fibrinogen receptor antagonists
US5192746A (en) * 1990-07-09 1993-03-09 Tanabe Seiyaku Co., Ltd. Cyclic cell adhesion modulation compounds

Also Published As

Publication number Publication date
WO1993024520A1 (en) 1993-12-09
CA2137072C (en) 2000-06-13
MX9303332A (es) 1994-06-30
TW274085B (ko) 1996-04-11
DK0648224T3 (da) 1998-10-26
US6107275A (en) 2000-08-22
JPH07507310A (ja) 1995-08-10
ES2121088T3 (es) 1998-11-16
CA2137072A1 (en) 1993-12-09
EP0648224A1 (en) 1995-04-19
GR3027738T3 (en) 1998-11-30
AU4378393A (en) 1993-12-30
IL105885A0 (en) 1993-10-20
DE69319733T2 (de) 1999-01-14
NZ253452A (en) 1996-06-25
JP3398747B2 (ja) 2003-04-21
EP0648224B1 (en) 1998-07-15
AU672010B2 (en) 1996-09-19
ATE168380T1 (de) 1998-08-15
DE69319733D1 (de) 1998-08-20
KR100297184B1 (ko) 2001-10-22
IL105885A (en) 1999-06-20

Similar Documents

Publication Publication Date Title
ES2247735T3 (es) Peptidos opiaceos afines a receptores kappa.
KR880005148A (ko) 아미노산 유도체
KR910006324A (ko) 펩티다아제 및 아이소머라제 억제제
BG98793A (en) Animoacid derivatives, method for their preparation and pharmaceutical composition containing them
KR927003631A (ko) 펩티드 유도체, 그 제조방법, 이를 함유한 제제 및 녹내장의 치료방법
KR920000785A (ko) 새로운 혈소판 응집 억제인자
KR950701935A (ko) 항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체(Conformationally restrained peptide analogs as antiplatelet agents)
KR950701646A (ko) 폴리펩티드 봄베신 길항제(polypeptide bombestn antagonisis)
KR960700269A (ko) 신규한 펩티드(New Peptides)
CY1107990T1 (el) Τριπεπτιδια και παραγωγα τριπεπτιδιων για τη θepαπεια νευροεκφυλιστικων ασθενειων
KR880011198A (ko) 사이클릭 펩타이드 및 이의 제조방법
KR900001719A (ko) 지질 및 폴리펩티드로 되는 합성 폐 계면활성제의 제조 방법
FR2575164B1 (fr) Esters de tri- et tetrapeptides inhibiteurs de la secretion gastrique, procede d'obtention et compositions pharmaceutiques les contenant
RU96123269A (ru) Три-, тетра-, пента- и полипептиды и их терапевтическое применение в качестве антидепрессивного агента
KR920002628A (ko) 펩티드
RU2001102617A (ru) Соединения, обладающие свойствами высвобождения гормона роста
HUP0401589A2 (hu) Új peptidek - humán növekedési hormont felszabadító hormonanalógok
AU718320B2 (en) Peptide derivatives
US6228841B1 (en) Peptide derivatives
KR930703348A (ko) 인자 Ⅱ에이(Ⅱa) 억제제
KR890009974A (ko) 신규 화합물들
KR960703612A (ko) 면역계 및 중추 신경계 치료용 신규의 트리펩티드(novel tripeptides useful in immune and cns therapy)
KR920701242A (ko) 환원된 비가역성 봄베신 길항제
KR880013902A (ko) 아미노산 유도체
Krasnov et al. The synthesis and biological activity of 4-[bis (2-chloroethyl) amino]-DL-, L, and D-phenylalanine amides and peptides

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20050518

Year of fee payment: 5

LAPS Lapse due to unpaid annual fee