IL94981A - Antiviral peptides having a side chain of 2-oxoalkyl, their preparation and pharmaceutical preparations containing them - Google Patents

Antiviral peptides having a side chain of 2-oxoalkyl, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL94981A
Authority: IL; Israel
Prior art keywords: alkyl; hydrogen; peptide; lower alkyl; phenyl
Prior art date: 1989-07-07

Application number

IL9498190A

Other languages

English (en)

Hebrew (he)

Other versions

IL94981A0 (en

Original Assignee

Bio Mega Boehringer Ingelheim

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.)

1989-07-07

Filing date

1990-07-05

Publication date

1995-03-15

1990-07-05 Application filed by Bio Mega Boehringer Ingelheim filed Critical Bio Mega Boehringer Ingelheim

1991-06-10 Publication of IL94981A0 publication Critical patent/IL94981A0/xx

1995-03-15 Publication of IL94981A publication Critical patent/IL94981A/en

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 96
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
102000004196 processed proteins & peptides Human genes 0.000 title description 37
238000002360 preparation method Methods 0.000 title description 12
230000000840 anti-viral effect Effects 0.000 title description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 67
239000001257 hydrogen Substances 0.000 claims abstract description 45
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
150000002431 hydrogen Chemical class 0.000 claims abstract description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
125000000539 amino acid group Chemical group 0.000 claims abstract description 14
150000001413 amino acids Chemical class 0.000 claims abstract description 14
125000001589 carboacyl group Chemical group 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 3
-1 2-carboxyphenyl Chemical group 0.000 claims description 96
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 17
230000008878 coupling Effects 0.000 claims description 17
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238000005859 coupling reaction Methods 0.000 claims description 17
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125000006239 protecting group Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 12
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 3
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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125000005842 heteroatom Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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150000003254 radicals Chemical class 0.000 abstract description 5
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Classifications

- 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
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
- 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
- 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
- C12N2710/00—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA dsDNA viruses
- C12N2710/00011—Details
- C12N2710/16011—Herpesviridae
- C12N2710/16611—Simplexvirus, e.g. human herpesvirus 1, 2
- C12N2710/16622—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Virology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Cosmetics (AREA)

IL9498190A 1989-07-07 1990-07-05 Antiviral peptides having a side chain of 2-oxoalkyl, their preparation and pharmaceutical preparations containing them IL94981A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000605062A CA1340682C (en)	1989-07-07	1989-07-07	Antiviral peptides having a 2-oxoalkyl amino acid side chain

Publications (2)

Publication Number	Publication Date
IL94981A0 IL94981A0 (en)	1991-06-10
IL94981A true IL94981A (en)	1995-03-15

Family

ID=4140313

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9498190A IL94981A (en)	1989-07-07	1990-07-05	Antiviral peptides having a side chain of 2-oxoalkyl, their preparation and pharmaceutical preparations containing them

Country Status (8)

Country	Link
US (1)	US5700780A (de)
EP (1)	EP0411332B1 (de)
JP (1)	JP2877910B2 (de)
AT (1)	ATE131174T1 (de)
AU (1)	AU643448B2 (de)
CA (1)	CA1340682C (de)
DE (1)	DE69023977T2 (de)
IL (1)	IL94981A (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU643636B2 (en) *	1989-07-07	1993-11-18	Bio-Mega/Boehringer Ingelheim Research Inc.	Antiherpes pentapeptide derivatives having a substituted aspartic acid side chain
EP0411333B1 (de) *	1989-07-07	1995-05-31	Bio-Mega/Boehringer Ingelheim Research Inc.	Antiherpes-Tetrapeptid-Derivate mit einer substituierten Seitenkette aus Asparaginsäure
CA1340681C (en) *	1989-07-07	1999-07-27	Robert Deziel	Antiherpes tetrapeptides having a substituted aspartic acid side chain
US5846941A (en) *	1992-03-12	1998-12-08	Boehringer Ingelheim (Canada) Ltd.	Isosteric antiherpes peptide derivatives II
ATE169931T1 (de)	1992-03-12	1998-09-15	Boehringer Ingelheim Ca Ltd	Isosterische peptidderivate gegen herpes
US6465612B1 (en) *	1998-09-23	2002-10-15	The Regents Of The University Of California	Synthetic peptides, conjugation reagents and methods
WO2001057072A2 (en)	2000-02-07	2001-08-09	Wisconsin Alumni Research Foundation	Pharmacologically active antiviral peptides and methods of their use
WO2005060541A2 (en) *	2003-12-01	2005-07-07	Wisconsin Alumni Research Foundation	Peptides and methods for inducing cellular resistance to infection

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4795740A (en) *	1986-05-20	1989-01-03	Cohen Eric A	Antiviral peptides and means for treating herpes infections
EP0292255A3 (de) *	1987-05-22	1990-08-22	Merck & Co. Inc.	Hemmungsstoff für Ribonukleotid-Reduktase
US4845195A (en) *	1987-05-22	1989-07-04	Merck & Co., Inc.	Inhibitor of ribonucleotide reductase
US4814432A (en) *	1987-05-22	1989-03-21	Merck & Co., Inc.	Inhibitor of ribonucleotide reductase
US4837304A (en) *	1987-05-22	1989-06-06	Merck & Co., Inc.	Inhibitor of ribonucleotide reductase
IL90872A0 (en) *	1988-07-08	1990-02-09	Smithkline Beckman Corp	Retroviral protease binding peptides
EP0357332A3 (de) *	1988-08-24	1991-07-31	Merck & Co. Inc.	Renin-Inhibitoren zur Behandlung von AIDS durch Hemmung der HIV-Protease
EP0374097A3 (de) *	1988-12-15	1991-06-12	Ciba-Geigy Ag	Verwendung von Peptidisosteren als retrovirale Proteasehemmer
AU643636B2 (en) *	1989-07-07	1993-11-18	Bio-Mega/Boehringer Ingelheim Research Inc.	Antiherpes pentapeptide derivatives having a substituted aspartic acid side chain
EP0411333B1 (de) *	1989-07-07	1995-05-31	Bio-Mega/Boehringer Ingelheim Research Inc.	Antiherpes-Tetrapeptid-Derivate mit einer substituierten Seitenkette aus Asparaginsäure
CA1340684C (en) *	1989-07-07	1999-07-27	Pierre Louis Beaulieu	Antiherpes pentapeptides
CA1340683C (en) *	1989-07-07	1999-07-27	Pierre Louis Beaulieu	Antiherpes pentapeptides having a substituted aspartic acid side chain

1989
- 1989-07-07 CA CA000605062A patent/CA1340682C/en not_active Expired - Fee Related
1990
- 1990-07-03 EP EP90112644A patent/EP0411332B1/de not_active Expired - Lifetime
- 1990-07-03 DE DE69023977T patent/DE69023977T2/de not_active Expired - Fee Related
- 1990-07-03 AT AT90112644T patent/ATE131174T1/de active
- 1990-07-05 IL IL9498190A patent/IL94981A/en unknown
- 1990-07-06 JP JP2179374A patent/JP2877910B2/ja not_active Expired - Lifetime
- 1990-07-06 AU AU58777/90A patent/AU643448B2/en not_active Ceased
1995
- 1995-10-11 US US08/540,862 patent/US5700780A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69023977D1 (de)	1996-01-18
DE69023977T2 (de)	1996-05-15
EP0411332A1 (de)	1991-02-06
EP0411332B1 (de)	1995-12-06
JP2877910B2 (ja)	1999-04-05
AU643448B2 (en)	1993-11-18
ATE131174T1 (de)	1995-12-15
AU5877790A (en)	1991-01-10
US5700780A (en)	1997-12-23
IL94981A0 (en)	1991-06-10
CA1340682C (en)	1999-07-27
JPH03115296A (ja)	1991-05-16

Publication	Publication Date	Title
EP0461546B1 (de)	1995-03-22	Antiherpes-Peptidderivate mit einem 1,4-Dioxo-C4-N-Terminus
EP0411332B1 (de)	1995-12-06	Antivirale Peptide, die eine 2-Ketoalkylaminosäureseitenkette enthalten
CA1340681C (en)	1999-07-27	Antiherpes tetrapeptides having a substituted aspartic acid side chain
US5552384A (en)	1996-09-03	Antiherpes compositions and method of use
EP0411334B1 (de)	1995-02-22	Pentapeptidderivate, wirksam gegen Herpes, die eine ersetzte Asparaginsäureseitenkette enthalten
US5502036A (en)	1996-03-26	Antiherpes pentapeptide derivatives having a substituted aspartic acid side chain
CA1340684C (en)	1999-07-27	Antiherpes pentapeptides
EP0411333B1 (de)	1995-05-31	Antiherpes-Tetrapeptid-Derivate mit einer substituierten Seitenkette aus Asparaginsäure
AU683450B2 (en)	1997-11-13	Inhibitors of herpes viral ribonucleotide reductase
US5149778A (en)	1992-09-22	Cyclic peptides for treating herpes infections
US5648337A (en)	1997-07-15	Antiherpes pentapeptides
US5258493A (en)	1993-11-02	Cyclic peptides for treating herpes infections
CA2019005C (en)	2000-04-18	Antiherpes pentapeptide derivatives having a cycloalkyl substituted aspartic acid side chain
CA2019006C (en)	2000-06-13	Antiherpes tetrapeptide derivatives having a cycloalkyl substituted aspartic acid side chain
NZ234373A (en)	1997-06-24	Acylated n-terminal tetrapeptides having an esterified or amidified aspartic acid residue and optionally substituted at the c-terminal by 5-1h-tetrazolyl; use in treatment of herpes virus infections