ZA200301015B - Selective cyclic peptides. - Google Patents

Selective cyclic peptides. Download PDF

Info

Publication number: ZA200301015B
Authority: ZA; South Africa
Prior art keywords: lys; asp; hydrogen; phe; cyclo
Prior art date: 2000-08-30

Application number

ZA200301015A

Other languages

English (en)

Inventor

Li Chen

Xin-Jie Chu

Joseph Swistok

Keith Alan Yagaloff

Adrian Wai-Hing Cheung

Waleed Danho

Yao Wang

Original Assignee

Hoffmann La Roche

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.)

2000-08-30

Filing date

2003-02-05

Publication date

2004-05-05

2003-02-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-05-05 Publication of ZA200301015B publication Critical patent/ZA200301015B/en

Links

102000001189 Cyclic Peptides Human genes 0.000 title description 3
108010069514 Cyclic Peptides Proteins 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 100
229910052739 hydrogen Inorganic materials 0.000 claims description 100
239000001257 hydrogen Substances 0.000 claims description 100
125000000217 alkyl group Chemical group 0.000 claims description 71
125000004432 carbon atom Chemical group C* 0.000 claims description 69
108010092854 aspartyllysine Proteins 0.000 claims description 58
OAMLVOVXNKILLQ-BQBZGAKWSA-N Asp-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC(O)=O OAMLVOVXNKILLQ-BQBZGAKWSA-N 0.000 claims description 57
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
150000002431 hydrogen Chemical class 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
108010021436 Type 4 Melanocortin Receptor Proteins 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 8
235000020824 obesity Nutrition 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
108090000765 processed proteins & peptides Proteins 0.000 claims description 5
102000004196 processed proteins & peptides Human genes 0.000 claims description 5
OABOXRPGTFRBFZ-IMJSIDKUSA-N Cys-Cys Chemical compound SC[C@H](N)C(=O)N[C@@H](CS)C(O)=O OABOXRPGTFRBFZ-IMJSIDKUSA-N 0.000 claims description 4
108010004073 cysteinylcysteine Proteins 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
229910019567 Re Re Inorganic materials 0.000 claims description 3
-1 or Chemical group 0.000 claims description 3
BBBXWRGITSUJPB-YUMQZZPRSA-N Glu-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCC(O)=O BBBXWRGITSUJPB-YUMQZZPRSA-N 0.000 claims description 2
238000000034 method Methods 0.000 claims 13
125000001475 halogen functional group Chemical group 0.000 claims 11
239000000203 mixture Substances 0.000 claims 7
239000000126 substance Substances 0.000 claims 6
201000010099 disease Diseases 0.000 claims 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
102000001796 Melanocortin 4 receptors Human genes 0.000 claims 3
238000011321 prophylaxis Methods 0.000 claims 3
241001465754 Metazoa Species 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
230000001225 therapeutic effect Effects 0.000 claims 2
241000735495 Erica <angiosperm> Species 0.000 claims 1
235000008694 Humulus lupulus Nutrition 0.000 claims 1
244000025221 Humulus lupulus Species 0.000 claims 1
241000283984 Rodentia Species 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
239000000556 agonist Substances 0.000 description 12
102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 8
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
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230000008484 agonism Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000037406 food intake Effects 0.000 description 3
235000012631 food intake Nutrition 0.000 description 3
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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150000001412 amines Chemical class 0.000 description 2
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229960000258 corticotropin Drugs 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
210000002752 melanocyte Anatomy 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
JDKLPDJLXHXHNV-MFVUMRCOSA-N (3s,6s,9r,12s,15s,23s)-15-[[(2s)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1h-imidazol-5-ylmethyl)-3-(1h-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxamide Chemical compound C([C@@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCNC(=O)C[C@@H](C(N[C@@H](CC=2NC=NC=2)C(=O)N1)=O)NC(=O)[C@@H](NC(C)=O)CCCC)C(N)=O)C1=CC=CC=C1 JDKLPDJLXHXHNV-MFVUMRCOSA-N 0.000 description 1
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
102100022455 Adrenocorticotropic hormone receptor Human genes 0.000 description 1
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ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
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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
- C07K7/64—Cyclic peptides containing only normal peptide links
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- 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
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/68—Melanocyte-stimulating hormone [MSH]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

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Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
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Medicinal Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
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Biochemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Zoology (AREA)
Gastroenterology & Hepatology (AREA)
Toxicology (AREA)
Endocrinology (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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ZA200301015A 2000-08-30 2003-02-05 Selective cyclic peptides. ZA200301015B (en)

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US22918400P	2000-08-30	2000-08-30

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ZA200301015A ZA200301015B (en)	2000-08-30	2003-02-05	Selective cyclic peptides.

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JP (1)	JP4217069B2 (fr)
KR (1)	KR100483300B1 (fr)
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AR (2)	AR030504A1 (fr)
AT (1)	ATE353918T1 (fr)
AU (2)	AU8402601A (fr)
BR (1)	BR0113637A (fr)
CA (1)	CA2420058C (fr)
CY (1)	CY1106562T1 (fr)
CZ (1)	CZ2003584A3 (fr)
DE (1)	DE60126624T2 (fr)
DK (1)	DK1315750T3 (fr)
EC (1)	ECSP034503A (fr)
ES (1)	ES2280393T3 (fr)
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IL (2)	IL154575A0 (fr)
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MA (1)	MA27681A1 (fr)
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PA (1)	PA8527201A1 (fr)
PE (1)	PE20020483A1 (fr)
PL (1)	PL366630A1 (fr)
PT (1)	PT1315750E (fr)
RU (1)	RU2239642C1 (fr)
SI (1)	SI1315750T1 (fr)
TW (1)	TWI248941B (fr)
WO (1)	WO2002018437A2 (fr)
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ZA (1)	ZA200301015B (fr)

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- 2001-08-21 PL PL01366630A patent/PL366630A1/xx not_active Application Discontinuation
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- 2001-08-21 AT AT01962958T patent/ATE353918T1/de active
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Also Published As

Publication number	Publication date
NZ523989A (en)	2004-08-27
DE60126624T2 (de)	2007-11-22
JP2004507558A (ja)	2004-03-11
HRP20030126B1 (en)	2009-01-31
ECSP034503A (es)	2003-04-25
MA27681A1 (fr)	2006-01-02
ES2280393T3 (es)	2007-09-16
WO2002018437A2 (fr)	2002-03-07
KR20030061788A (ko)	2003-07-22
BR0113637A (pt)	2004-02-25
PE20020483A1 (es)	2002-06-06
WO2002018437A3 (fr)	2002-06-06
RU2239642C1 (ru)	2004-11-10
IL154575A (en)	2008-12-29
US20020143141A1 (en)	2002-10-03
HRP20030126A2 (en)	2005-10-31
AU8402601A (en)	2002-03-13
CN100491396C (zh)	2009-05-27
NO20030916D0 (no)	2003-02-27
YU15603A (sh)	2006-05-25
AU2001284026B2 (en)	2007-03-01
MY137457A (en)	2009-01-30
PT1315750E (pt)	2007-05-31
AR061422A2 (es)	2008-08-27
US7045591B2 (en)	2006-05-16
PA8527201A1 (es)	2002-04-25
JO2454B1 (en)	2008-10-09
TWI248941B (en)	2006-02-11
MXPA03001721A (es)	2003-05-27
EP1315750B1 (fr)	2007-02-14
KR100483300B1 (ko)	2005-04-15
SI1315750T1 (sl)	2007-06-30
HUP0303078A3 (en)	2012-02-28
DE60126624D1 (de)	2007-03-29
PL366630A1 (en)	2005-02-07
CA2420058C (fr)	2009-04-07
HUP0303078A2 (hu)	2003-12-29
CY1106562T1 (el)	2012-01-25
NO20030916L (no)	2003-02-27
AR030504A1 (es)	2003-08-20
CA2420058A1 (fr)	2002-03-07
CZ2003584A3 (cs)	2003-08-13
IL154575A0 (en)	2003-09-17
JP4217069B2 (ja)	2009-01-28
EP1315750A2 (fr)	2003-06-04
CN1451017A (zh)	2003-10-22
DK1315750T3 (da)	2007-06-11
ATE353918T1 (de)	2007-03-15

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RU2381233C2 (ru)	2010-02-10	Агонисты рецептора меланокортина
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