KR970705576A - 페닐 펩티드, 이를 제조하는 방법, 및 이 펩티드를 함유하는 약제학적 조성물(phenyl peptides, method for preparing same, and pharmaceutical compositions containing said peptides) - Google Patents
페닐 펩티드, 이를 제조하는 방법, 및 이 펩티드를 함유하는 약제학적 조성물(phenyl peptides, method for preparing same, and pharmaceutical compositions containing said peptides) Download PDFInfo
- Publication number
- KR970705576A KR970705576A KR1019970701333A KR19970701333A KR970705576A KR 970705576 A KR970705576 A KR 970705576A KR 1019970701333 A KR1019970701333 A KR 1019970701333A KR 19970701333 A KR19970701333 A KR 19970701333A KR 970705576 A KR970705576 A KR 970705576A
- Authority
- KR
- South Korea
- Prior art keywords
- leu
- formula
- amino
- ile
- phenyl
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract 5
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title claims 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 239000011593 sulfur Substances 0.000 claims abstract 6
- 125000003277 amino group Chemical group 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 150000003462 sulfoxides Chemical class 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 150000001413 amino acids Chemical class 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- -1 nitro, amino Chemical group 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- MDXGYYOJGPFFJL-QMMMGPOBSA-N N(alpha)-t-butoxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OC(C)(C)C MDXGYYOJGPFFJL-QMMMGPOBSA-N 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 abstract 2
- 102000004580 Aspartic Acid Proteases Human genes 0.000 abstract 1
- 108010017640 Aspartic Acid Proteases Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 108010076039 Polyproteins Proteins 0.000 abstract 1
- 101710172711 Structural protein Proteins 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 230000010076 replication Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
- C07K14/08—RNA viruses
- C07K14/15—Retroviridae, e.g. bovine leukaemia virus, feline leukaemia virus human T-cell leukaemia-lymphoma virus
- C07K14/155—Lentiviridae, e.g. human immunodeficiency virus [HIV], visna-maedi virus or equine infectious anaemia virus
- C07K14/16—HIV-1 ; HIV-2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16211—Human Immunodeficiency Virus, HIV concerning HIV gagpol
- C12N2740/16222—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- AIDS & HIV (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
본 발명은 유기 화학 및 특히 치료 화학에 사용하는 합성 펩티드에 관한 것이다. 이러한 펩티드는 하기 구조의 아미노산을 9개 이상 함유한다 :
상기 식에서, X 및 Y는 보호되거나 보호되지 않은 아미노산 잔기, 또는 펩티드이고, R은 직쇄 또는 측쇄 알킬 라디칼이고, R″은 알킬, 페닐, 할로겐, 니트로, 아미노, 알킬 아미노, 알콕시, 트리플루오로메틸, 트리플루오로메톡시, 카르복사미도 또는 시아노 라다칼 중 하나이고, Z는 황, 산소, 아미노기 또는 술폭시화물이며, n은 0, 1, 2 또는 3이다.
상기 화학식의 화합물은 HIV 바이러스의 구조 단백질 및 구성 효소를 코드화하는 다단백질의 전구체를 분해하는 작은 아스파르틸 프로테아제 이합체의 억제제로서 작용함으로써 HIV의 복제를 억제한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 하기 화학식의 9개 이상의 아미노산을 함유하는 합성 펩티드:상기 식에서, X 및 Y는 보호되거나 보호되지 않은 아미노산 잔기, 또는 펩티드이고, R은 직쇄 또는 측쇄 알킬 라디칼이고, R″은 알킬, 페닐, 할로겐, 니트로, 아미노, 알킬 아미노, 알콕시, 트리플루오로메틸, 트리플루오로메톡시, 카르복사미도 또는 시아노 라다칼 중 하나이고, Z는 황, 산소, 아미노기 또는 술폭시화물이며, n은 0,1,2 또는 3이다.
- 제1항에 있어서, 하기 화학식을 가지는 것을 특징으로 하는 펩티드:상기 식에서, X, Y, R, R″및 n은 제1항에서 정의한 바와 같다.
- 제1항에 있어서, 하기의 단순화된 화학식을 가지는 것을 특징으로 하는 펩티드:상기 식에서, Ar은 치환되지 않거나 치환된 페닐 라디칼이고, Z는 황, 산소, 아미노 또는 술폭시화물이다.
- 제3항에 있어서, 하기의 단순화된 화학식을 가지는 것을 특징으로 하는 펩티드:상기 식에서, Ar은 제3항에서 정의한 바와 같다.
- 제1항 또는 2항에 있어서, Ile-Arg-Lys-Ile-Leu-(S)Phe-Leu-Asp-Gly-NH2를 가지는 것을 특징으로 하는 펩티드.
- 제1항 또는 2항에 있어서, Ile-Arg-Lys-Ile-Leu-(S)Phe-Leu-Asp-Ile-OH인 것을 특징으로 하는 펩티드.
- 제1항 내지 6항 중 어느 한 한에 따른 펩티드를 제조하는 방법으로서, 하기 화학식(2)의 [(Boc Leu)-아미노]페닐 Z 아세트산이 신톤으로서 사용되고, 말단 아민 작용기가 트리플루오로아세트산에 의해 탈보호되거나, 사슬의 탈보호 및 수지의 분해이 아니솔의 존재하에 플루오르화수소산을 사용하여 수행되는 방법:상기 식에서, Y는 치환되지 않거나 1,2 또는 3개의 R″치환기에 의해 치환된 페닐 라디칼이고, Z는 황, 산소, 아미노 및 술폭시화물이며, 여기에 노나펩티드의 사슬을 구성하는 서로 다른 아미노산이 고체상 수지를 사용하는 기술에 의해 결합된다.
- 약제학적으로 수용가능하고, 비독성이고, 비활성인 부형제 또는 담체와 조합되거나 혼합된 하기 화학식(1b)의 하나 이상의 화합물을 활성 성분으로서 함유하는 약제학적 조성물:상기 식에서, X 및 Y는 보호되거나 보호되지 않은 아미노산 잔기, 또는 펩티드이고, R은 직쇄 또는 측쇄 알킬 라디칼이고, R″은 알킬, 페닐, 할로겐, 니트로, 아미노, 알킬 아미노, 알콕시, 트리플루오로메틸, 트리플루오로메톡시, 카르복사미도 또는 시아노 라다칼 중 하나이고, Z는 황, 산소, 아미노기 또는 술폭시화물이며, n은 0,1,2 또는 3이다.
- 약제학적 수용가능하고, 비독성이고, 비활성인 부형제 또는 담체와 조합되거나 혼합된 하기 화학식(1a)의 하나 이상의 화합물을 활성 성분으로서 함유하는 약제학적 조성물:상기 식에서, Z는 황, 산소, 아미노기 또는 술폭시화물이고, Ar은 치환되지 않거나 치환된 페닐 라디칼이다.
- 화학식(1a) 또는 (1b)의 화합물을 합성하기 위해 중간체로서 Fmoc-Ile-Arg-Lys-Ile-Leu-(S)Phe-Leu-Asp-Gly-NH2.
- 화학식(1a) 또는 (1b)의 화합물을 합성하기 위해 중간체로서 Fmoc-Ile-Arg-Lys-Ile-Leu-(S)Phe-Leu-Asp-Gly-Ile-OH.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9507817A FR2736055B1 (fr) | 1995-06-29 | 1995-06-29 | Nouveaux thiophenoxy peptides, leur procede de preparation et les compositions pharmaceutiques en renfermant |
FR95/07817 | 1995-06-29 | ||
PCT/FR1996/001008 WO1997001576A2 (fr) | 1995-06-29 | 1996-06-28 | Peptides phenyles, leur procede de preparation et les compositions pharmaceutiques qui en renferment |
Publications (1)
Publication Number | Publication Date |
---|---|
KR970705576A true KR970705576A (ko) | 1997-10-09 |
Family
ID=9480502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970701333A KR970705576A (ko) | 1995-06-29 | 1996-06-28 | 페닐 펩티드, 이를 제조하는 방법, 및 이 펩티드를 함유하는 약제학적 조성물(phenyl peptides, method for preparing same, and pharmaceutical compositions containing said peptides) |
Country Status (17)
Country | Link |
---|---|
US (1) | US5844078A (ko) |
EP (1) | EP0787143A2 (ko) |
JP (1) | JPH10505613A (ko) |
KR (1) | KR970705576A (ko) |
CN (1) | CN1165521A (ko) |
AP (1) | AP683A (ko) |
AU (1) | AU706799B2 (ko) |
BR (1) | BR9606455A (ko) |
CA (1) | CA2197861A1 (ko) |
FR (1) | FR2736055B1 (ko) |
HU (1) | HUP9701940A3 (ko) |
IL (1) | IL120341A (ko) |
NO (1) | NO970895L (ko) |
NZ (1) | NZ312726A (ko) |
OA (1) | OA10403A (ko) |
PL (1) | PL318880A1 (ko) |
WO (1) | WO1997001576A2 (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1292438B1 (it) * | 1997-06-30 | 1999-02-08 | Zambon Spa | Derivati peptidomimetici inibitori suicidi della proliferazione del hiv |
US6118226A (en) | 1998-07-31 | 2000-09-12 | Federal-Mogul World Wide, Inc. | Electrodeless neon light module for vehicle lighting systems |
US8886480B2 (en) | 2011-06-27 | 2014-11-11 | Synaptics Incorporated | System and method for signaling in gradient sensor devices |
US9188675B2 (en) | 2012-03-23 | 2015-11-17 | Synaptics Incorporated | System and method for sensing multiple input objects with gradient sensor devices |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1193598A (en) * | 1982-05-06 | 1985-09-17 | Rafael Foguet | 2-amino-benzoic acid derivatives and processes for their production |
ZA832844B (en) * | 1982-05-18 | 1984-03-28 | Smithkline Beckman Corp | Oligopeptide prodrugs |
US4454065A (en) * | 1982-05-18 | 1984-06-12 | Smithkline Beckman Corporation | Oligopeptide prodrugs |
US5036054A (en) * | 1988-02-11 | 1991-07-30 | Warner-Lambert Company | Renin inhibitors containing alpha-heteroatom amino acids |
US5221667A (en) * | 1990-01-22 | 1993-06-22 | Warner-Lambert Company | Renin inhibiting peptides having an α-heteroatom amino acid at the P3 position |
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1995
- 1995-06-29 FR FR9507817A patent/FR2736055B1/fr not_active Expired - Lifetime
-
1996
- 1996-06-28 KR KR1019970701333A patent/KR970705576A/ko not_active Application Discontinuation
- 1996-06-28 AP APAP/P/1997/000964A patent/AP683A/en active
- 1996-06-28 HU HU9701940A patent/HUP9701940A3/hu unknown
- 1996-06-28 JP JP9504212A patent/JPH10505613A/ja active Pending
- 1996-06-28 IL IL12034196A patent/IL120341A/xx active IP Right Grant
- 1996-06-28 PL PL96318880A patent/PL318880A1/xx unknown
- 1996-06-28 EP EP96924035A patent/EP0787143A2/fr not_active Withdrawn
- 1996-06-28 CA CA002197861A patent/CA2197861A1/fr not_active Abandoned
- 1996-06-28 US US08/793,647 patent/US5844078A/en not_active Expired - Fee Related
- 1996-06-28 AU AU64624/96A patent/AU706799B2/en not_active Ceased
- 1996-06-28 WO PCT/FR1996/001008 patent/WO1997001576A2/fr not_active Application Discontinuation
- 1996-06-28 BR BR9606455A patent/BR9606455A/pt not_active Application Discontinuation
- 1996-06-28 CN CN96190943A patent/CN1165521A/zh active Pending
- 1996-06-28 NZ NZ312726A patent/NZ312726A/en unknown
-
1997
- 1997-02-27 NO NO970895A patent/NO970895L/no not_active Application Discontinuation
- 1997-02-28 OA OA60971A patent/OA10403A/fr unknown
Also Published As
Publication number | Publication date |
---|---|
IL120341A (en) | 2001-01-28 |
FR2736055B1 (fr) | 1997-09-12 |
FR2736055A1 (fr) | 1997-01-03 |
CA2197861A1 (fr) | 1997-01-16 |
AP9700964A0 (en) | 1997-04-30 |
HUP9701940A3 (en) | 2001-07-30 |
NO970895D0 (no) | 1997-02-27 |
NZ312726A (en) | 1998-07-28 |
WO1997001576A3 (fr) | 1997-05-15 |
AU6462496A (en) | 1997-01-30 |
BR9606455A (pt) | 1998-07-14 |
JPH10505613A (ja) | 1998-06-02 |
OA10403A (fr) | 2001-12-05 |
HUP9701940A2 (hu) | 1998-03-02 |
IL120341A0 (en) | 1997-06-10 |
WO1997001576A2 (fr) | 1997-01-16 |
AP683A (en) | 1998-09-30 |
NO970895L (no) | 1997-02-27 |
AU706799B2 (en) | 1999-06-24 |
US5844078A (en) | 1998-12-01 |
CN1165521A (zh) | 1997-11-19 |
PL318880A1 (en) | 1997-07-07 |
EP0787143A2 (fr) | 1997-08-06 |
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