IL99628A - Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them - Google Patents

Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them

Info

Publication number: IL99628A
Authority: IL; Israel
Prior art keywords: formula; compound; group; amino acid; give
Prior art date: 1991-10-02

Application number

IL9962891A

Other languages

English (en)

Other versions

IL99628A0 (en

Inventor

Chaim Gilon

Zvi Zelinger

Original Assignee

Yissum Res Dev Co

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.)

1991-10-02

Filing date

1991-10-02

Publication date

2004-07-25

1991-10-02 Application filed by Yissum Res Dev Co filed Critical Yissum Res Dev Co

1991-10-02 Priority to IL9962891A priority Critical patent/IL99628A/en

1992-08-18 Publication of IL99628A0 publication Critical patent/IL99628A0/xx

1992-10-02 Priority to EP92309016A priority patent/EP0564739B1/en

1992-10-02 Priority to AT92309016T priority patent/ATE189228T1/de

1992-10-02 Priority to DE69230610T priority patent/DE69230610T2/de

1992-10-02 Priority to JP30434792A priority patent/JP3509029B2/ja

1995-05-18 Priority to US08/444,135 priority patent/US5723575A/en

1995-12-07 Priority to US08/569,042 priority patent/US6117974A/en

2004-07-25 Publication of IL99628A publication Critical patent/IL99628A/en

Links

238000000034 method Methods 0.000 title claims abstract description 74
230000008569 process Effects 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
108010069514 Cyclic Peptides Proteins 0.000 title description 7
102000001189 Cyclic Peptides Human genes 0.000 title description 7
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 103
102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims description 97
125000006239 protecting group Chemical group 0.000 claims description 49
150000001413 amino acids Chemical group 0.000 claims description 32
125000000539 amino acid group Chemical group 0.000 claims description 29
238000010647 peptide synthesis reaction Methods 0.000 claims description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
230000000903 blocking effect Effects 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
229920001184 polypeptide Polymers 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
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239000004480 active ingredient Substances 0.000 claims description 4
125000006850 spacer group Chemical group 0.000 claims description 4
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125000001424 substituent group Chemical group 0.000 claims description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
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CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
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239000010452 phosphate Substances 0.000 claims description 2
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QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims 1
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OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
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 class 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 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
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239000003153 chemical reaction reagent Substances 0.000 description 8
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
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UUZURPUIMYJOIL-JNRWAQIZSA-N (2s)-n-[(2s)-1-[[(2s)-1-[(2s)-2-[[(2s)-1-[[(2s)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound CSCC[C@@H](C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=CC=C1 UUZURPUIMYJOIL-JNRWAQIZSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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230000000694 effects Effects 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
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HMHYXLVEFVGOPM-QKUYTOGTSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[2-[[(2s)-1-[[(2s)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]-methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(3-carboxypropanoylamino)-4-oxobutan Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)N(C)C(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)CCC(O)=O)C1=CC=CC=C1 HMHYXLVEFVGOPM-QKUYTOGTSA-N 0.000 description 5
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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
- C07K7/04—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic 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
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

IL9962891A 1991-10-02 1991-10-02 Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them IL99628A (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
IL9962891A IL99628A (en)	1991-10-02	1991-10-02	Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them
EP92309016A EP0564739B1 (en)	1991-10-02	1992-10-02	Backbone cyclic peptides, processes for their preparation and pharmaceutical compositions containing them
AT92309016T ATE189228T1 (de)	1991-10-02	1992-10-02	Peptide mit zyklischen hauptketten, deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE69230610T DE69230610T2 (de)	1991-10-02	1992-10-02	Peptide mit zyklischen Hauptketten, deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
JP30434792A JP3509029B2 (ja)	1991-10-02	1992-10-02	生物活性環化ポリペプチド
US08/444,135 US5723575A (en)	1991-10-02	1995-05-18	Process for the preparation of backbone cyclic peptides
US08/569,042 US6117974A (en)	1991-10-02	1995-12-07	Libraries of backbone-cyclized peptidomimetics

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL9962891A IL99628A (en)	1991-10-02	1991-10-02	Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them

Publications (2)

Publication Number	Publication Date
IL99628A0 IL99628A0 (en)	1992-08-18
IL99628A true IL99628A (en)	2004-07-25

Family

ID=11062920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9962891A IL99628A (en)	1991-10-02	1991-10-02	Processes for the preparation of cyclic peptides, and pharmaceutical compositions containing them

Country Status (6)

Country	Link
US (1)	US5723575A (ru)
EP (1)	EP0564739B1 (ru)
JP (1)	JP3509029B2 (ru)
AT (1)	ATE189228T1 (ru)
DE (1)	DE69230610T2 (ru)
IL (1)	IL99628A (ru)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6117974A (en) *	1991-10-02	2000-09-12	Peptor Limited	Libraries of backbone-cyclized peptidomimetics
US6872803B1 (en)	1993-09-21	2005-03-29	Kyowa Hakko Kogyo Co., Ltd.	Peptides
IL109943A (en) *	1994-06-08	2006-08-01	Develogen Israel Ltd	Conformationally constrained backbone cyclized peptide analogs
US6407059B1 (en) *	1994-06-08	2002-06-18	Peptor Limited	Conformationally constrained backbone cyclized peptide analogs
AU724386B2 (en) *	1994-06-08	2000-09-21	Peptor Ltd	Conformationally constrained backbone cyclized peptide analogs
US6051554A (en) *	1995-06-07	2000-04-18	Peptor Limited	Conformationally constrained backbone cyclized somatostatin analogs
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1992
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- 1992-10-02 DE DE69230610T patent/DE69230610T2/de not_active Expired - Fee Related
- 1992-10-02 EP EP92309016A patent/EP0564739B1/en not_active Expired - Lifetime
- 1992-10-02 JP JP30434792A patent/JP3509029B2/ja not_active Expired - Fee Related
1995
- 1995-05-18 US US08/444,135 patent/US5723575A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ATE189228T1 (de)	2000-02-15
IL99628A0 (en)	1992-08-18
EP0564739A3 (ru)	1995-04-26
JPH06263797A (ja)	1994-09-20
JP3509029B2 (ja)	2004-03-22
DE69230610D1 (de)	2000-03-02
DE69230610T2 (de)	2000-12-28
EP0564739B1 (en)	2000-01-26
EP0564739A2 (en)	1993-10-13
US5723575A (en)	1998-03-03

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KR20010022924A (ko)	2001-03-26	페네틸아민 유도체
KR100286242B1 (ko)	2001-04-16	돌라스타틴 유도체
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EP2662087A1 (en)	2013-11-13	Somatostatin vectors
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CA1157466A (en)	1983-11-22	Peptides having thymopoietin-like activity
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EP1348714B1 (en)	2007-01-03	Polypeptide useful as anti-allergic/antiasthmatic, methods for the preparation thereof and pharmaceutical compositions containing such polypeptide and their use
JPH10500404A (ja)	1998-01-13	混合したμアゴニスト／δアンタゴニストの性質を有する新規なオピオイドペプチド類似体
US20060160989A1 (en)	2006-07-20	Polypeptide useful as antiallergic/antiasthmatic activity, methods for the preparation thereof, pharmaceutical compositions containing such polypeptide and use thereof
AU766495B2 (en)	2003-10-16	Synthesis of cyclic peptides
JPS59101450A (ja)	1984-06-12	ペプチド

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