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)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Pharmacology & Pharmacy (AREA)
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Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Hematology (AREA)
Zoology (AREA)
Gastroenterology & Hepatology (AREA)
Diabetes (AREA)
Toxicology (AREA)
Endocrinology (AREA)
Obesity (AREA)
Child & Adolescent Psychology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US22918400P	2000-08-30	2000-08-30

Publications (1)

Publication Number	Publication Date
ZA200301015B true ZA200301015B (en)	2004-05-05

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

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Country	Link
US (1)	US7045591B2 (fr)
EP (1)	EP1315750B1 (fr)
JP (1)	JP4217069B2 (fr)
KR (1)	KR100483300B1 (fr)
CN (1)	CN100491396C (fr)
AR (2)	AR030504A1 (fr)
AT (1)	ATE353918T1 (fr)
AU (2)	AU2001284026B2 (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)
HR (1)	HRP20030126B1 (fr)
HU (1)	HUP0303078A3 (fr)
IL (2)	IL154575A0 (fr)
JO (1)	JO2454B1 (fr)
MA (1)	MA27681A1 (fr)
MX (1)	MXPA03001721A (fr)
MY (1)	MY137457A (fr)
NO (1)	NO20030916D0 (fr)
NZ (1)	NZ523989A (fr)
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)
YU (1)	YU15603A (fr)
ZA (1)	ZA200301015B (fr)

Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003006604A2 (fr) *	2001-07-12	2003-01-23	Merck & Co., Inc.	Peptides cycliques agonistes puissants et selectifs de recepteur de melanocortine-4
US7354923B2 (en)	2001-08-10	2008-04-08	Palatin Technologies, Inc.	Piperazine melanocortin-specific compounds
US7456184B2 (en)	2003-05-01	2008-11-25	Palatin Technologies Inc.	Melanocortin receptor-specific compounds
US7732451B2 (en)	2001-08-10	2010-06-08	Palatin Technologies, Inc.	Naphthalene-containing melanocortin receptor-specific small molecule
EP1425029A4 (fr)	2001-08-10	2006-06-07	Palatin Technologies Inc	Peptidomimetiques de metallopeptides biologiquement actifs
US7718802B2 (en)	2001-08-10	2010-05-18	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
US7655658B2 (en)	2001-08-10	2010-02-02	Palatin Technologies, Inc.	Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds
AU2003248888A1 (en)	2002-07-09	2004-01-23	Palatin Technologies, Inc.	Peptide composition for treatment of sexual dysfunction
US7727990B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine and keto-piperazine compounds
US7727991B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific single acyl piperazine compounds
US7968548B2 (en)	2003-05-01	2011-06-28	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine compounds with diamine groups
EP1625158A2 (fr) *	2003-05-09	2006-02-15	Novo Nordisk A/S	Peptides s'utilisant dans le traitement de l'obesite
KR20060026011A (ko)	2003-05-09	2006-03-22	노보 노르디스크 에이/에스	비만 치료용 펩티드
CA2527881A1 (fr) *	2003-06-19	2005-01-06	Eli Lilly And Company	Utilisation de peptides agonistes du recepteur de la melanocortine-3 (mc3r)
EP1644023A2 (fr) *	2003-06-19	2006-04-12	Eli Lilly And Company	Agonistes du recepteur 4 de la melanocortine (mc4) et utilisations
US7084111B2 (en)	2003-06-23	2006-08-01	University Of Florida Research Foundation, Inc.	Melanocortin receptor templates, peptides, and use thereof
CA2539596A1 (fr) *	2003-09-30	2005-04-07	Kilian Waldemar Conde-Frieboes	Nouveaux agonistes du recepteur de la melanocortine
US7550602B1 (en) *	2004-01-14	2009-06-23	Palatin Technologies, Inc.	Small molecule compositions for sexual dysfunction
US6974187B2 (en) *	2004-01-28	2005-12-13	Tachi-S Co., Ltd.	Vehicle seat structure
EP1732586A1 (fr) *	2004-03-29	2006-12-20	Eli Lilly And Company	Utilisations de peptides agonistes du recepteur de la melanocortine 4 (mc4r) administres par perfusion continue
KR101176758B1 (ko) *	2004-04-08	2012-08-23	아스테라스 세이야쿠 가부시키가이샤	화합물 ｗｓ727713
US7709484B1 (en)	2004-04-19	2010-05-04	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
EP1809666A2 (fr) *	2004-11-04	2007-07-25	Novo Nordisk A/S	Peptides utiles dans le traitement de l'obesite
JP2008519008A (ja) *	2004-11-04	2008-06-05	ノボノルディスクアクティーゼルスカブ	肥満症の治療に使用するためのペプチド
WO2006048449A2 (fr) *	2004-11-04	2006-05-11	Novo Nordisk A/S	Nouveaux peptides utiles dans le traitement de l'obesite
US20080280820A1 (en) *	2004-11-04	2008-11-13	Ulrich Sensfuss	Novel Peptides for Use in the Treatment of Obesity
WO2006129317A1 (fr) *	2005-05-31	2006-12-07	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Analogues de l'hormone stimulant la melanocortine ($g(a)msh) a squelette cyclise
EP1893240A2 (fr) *	2005-06-13	2008-03-05	Nastech Pharmaceutical Company Inc.	Administration transmucosale de dérivés peptidiques
US7671112B2 (en) *	2005-07-15	2010-03-02	3M Innovative Properties Company	Method of making fluoropolymer dispersion
US20080015304A1 (en)	2006-07-13	2008-01-17	Klaus Hintzer	Aqueous emulsion polymerization process for producing fluoropolymers
GB2430437A (en) *	2005-09-27	2007-03-28	3M Innovative Properties Co	Method of making a fluoropolymer
US7834017B2 (en)	2006-08-11	2010-11-16	Palatin Technologies, Inc.	Diamine-containing, tetra-substituted piperazine compounds having identical 1- and 4-substituents
EP2125862A1 (fr) *	2006-12-29	2009-12-02	F. Hoffmann-Roche AG	Procédés de synthèse de peptides cycliques
EP2132143B1 (fr) *	2007-02-16	2012-12-26	3M Innovative Properties Company	Système et procédé pour l'extraction de produits fluorochimiques à partir d'eau
US20080264864A1 (en) *	2007-04-27	2008-10-30	3M Innovative Properties Company	PROCESS FOR REMOVING FLUORINATED EMULSIFIER FROM FLUOROPOLMER DISPERSIONS USING AN ANION-EXCHANGE RESIN AND A pH-DEPENDENT SURFACTANT AND FLUOROPOLYMER DISPERSIONS CONTAINING A pH-DEPENDENT SURFACTANT
US8563000B2 (en)	2007-05-25	2013-10-22	Ipsen Pharma S.A.S.	Melanocortin receptor ligands modified with hydantoin
EP2172459B1 (fr)	2007-07-19	2014-03-19	Tokuyama Corporation	Composé ayant un cycle hydantoïne et son procédé de fabrication
CL2009000734A1 (es)	2008-03-27	2009-05-15	Gruenenthal Chemie	Compuestos derivados de 4-aminociclohexano sustituido; composicion farmaceutica que comprende a dichos compuestos; y su uso como moduladores del receptor de opioides u y el receptor orl-1 en el tratamiento de la ansiedad, estres, depresion, epilepsia y alzheimer.
PE20091657A1 (es) *	2008-03-27	2009-11-07	Gruenenthal Chemie	Derivados de (hetero)aril-ciclohexano
AU2009257631B2 (en)	2008-06-09	2014-07-24	Palatin Technologies, Inc.	Melanocortin receptor-specific peptides for treatment of sexual dysfunction
AR072072A1 (es) *	2008-06-09	2010-08-04	Palatin Technologies Inc	Peptidos especificos del receptor de melanocortina para el tratamiento de la obesidad / 669
EP2440572B1 (fr)	2009-06-08	2017-04-05	Palatin Technologies, Inc.	Peptides spécifiques des récepteurs aux mélanocortines à pont lactame
UY32690A (es)	2009-06-08	2011-01-31	Astrazeneca Ab	Péptidos específicos para receptores de melanocortina
AU2010259008C1 (en) *	2009-06-08	2016-04-21	Palatin Technologies, Inc.	Melanocortin receptor-specific peptides
AU2010321738B2 (en)	2009-11-23	2016-07-14	Palatin Technologies, Inc.	Melanocortin-1 receptor-specific cyclic peptides
AU2010321739A1 (en)	2009-11-23	2012-05-31	Palatin Technologies, Inc.	Melanocortin-1 receptor-specific linear peptides
AU2014227712B2 (en) *	2013-03-15	2018-08-02	Rhythm Pharmaceuticals, Inc.	Peptide compositions
GB201416352D0 (en)	2014-09-16	2014-10-29	Shire Internat Gmbh	Spirocyclic derivatives
GB201416351D0 (en)	2014-09-16	2014-10-29	Shire Internat Gmbh	Heterocyclic derivatives
EP3197481A1 (fr) *	2014-09-26	2017-08-02	Bayer Pharma Aktiengesellschaft	Dérivés d'adrénomédulline stabilisés et leur utilisation
US11542302B2 (en)	2015-10-15	2023-01-03	Arizona Board Of Regents On Behalf Of The University Of Arizona	Modulators of melanocortin receptors for the treatment of depression and anxiety
WO2018074999A1 (fr) *	2016-10-17	2018-04-26	The Arizona Board Of Regents On Behalf Of The University Of Arizona	Nouveaux modulateurs des récepteurs de mélanocortine pour le traitement de la dépression et de l'anxiété
US10653743B2 (en)	2015-10-15	2020-05-19	Arizona Board Of Regents On Behalf Of The University Of Arizona	Methods for the treatment of depression and anxiety by a melanocortin 5 receptor antagonist, PG-20N
US10899793B2 (en)	2016-05-27	2021-01-26	Regents Of The University Of Minnesota	Melanocortin ligands and methods of use thereof
US11124541B2 (en)	2016-10-18	2021-09-21	Regents Of The University Of Minnesota	Chimeric melanocortin ligands and methods of use thereof
CN106496008A (zh) *	2016-10-20	2017-03-15	上海毕得医药科技有限公司	一种合成4‑(4‑氯苯基)环己酮的方法
CN106496005B (zh) *	2016-10-20	2019-04-09	上海毕得医药科技有限公司	一种4-(4-氯苯基)环己酮的合成方法
US10745444B2 (en) *	2017-04-17	2020-08-18	National Tsing Hua University	Cyclopeptide, pharmaceutical or cosmetic composition comprising the same and method for preparing the same
US11332499B2 (en)	2018-08-16	2022-05-17	Regents Of The University Of Minnesota	Cyclic peptides and methods of use thereof
CN118530294B (zh) *	2024-05-10	2025-02-14	浙江大学	一种芳基二胺固载连接子、其前体以及制备方法和应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4237456A1 (de) *	1992-11-06	1994-05-11	Merck Patent Gmbh	Cyclopeptide
US5811391A (en)	1994-08-25	1998-09-22	Cytel Corporation	Cyclic CS-1 peptidomimetics, compositions and methods of using same
US5731408A (en) *	1995-04-10	1998-03-24	Arizona Board Of Regents On Behalf Of The University Of Arizona	Peptides having potent antagonist and agonist bioactivities at melanocortin receptors
US5858972A (en)	1996-01-11	1999-01-12	La Jolla Cancer Research Foundation	Antithrombotic agents and methods of use
SE9700620D0 (sv) *	1997-02-21	1997-02-21	Wapharm Ab	Cykliska peptider med selektivitet för MSH-receptor subtyper
KR100558131B1 (ko)	1999-03-29	2006-03-10	더 프록터 앤드 갬블 캄파니	멜라노코르틴 수용체 리간드를 함유하는 약제학적 조성물및 멜라노코르틴 수용체 리간드를 함유하는 약제의제조방법

2001
- 2001-08-21 KR KR10-2003-7002931A patent/KR100483300B1/ko not_active Expired - Fee Related
- 2001-08-21 CA CA002420058A patent/CA2420058C/fr not_active Expired - Fee Related
- 2001-08-21 YU YU15603A patent/YU15603A/sh unknown
- 2001-08-21 AU AU2001284026A patent/AU2001284026B2/en not_active Ceased
- 2001-08-21 IL IL15457501A patent/IL154575A0/xx unknown
- 2001-08-21 EP EP01962958A patent/EP1315750B1/fr not_active Expired - Lifetime
- 2001-08-21 PT PT01962958T patent/PT1315750E/pt unknown
- 2001-08-21 CN CNB018150284A patent/CN100491396C/zh not_active Expired - Fee Related
- 2001-08-21 ES ES01962958T patent/ES2280393T3/es not_active Expired - Lifetime
- 2001-08-21 JP JP2002523951A patent/JP4217069B2/ja not_active Expired - Fee Related
- 2001-08-21 HU HU0303078A patent/HUP0303078A3/hu unknown
- 2001-08-21 DE DE60126624T patent/DE60126624T2/de not_active Expired - Lifetime
- 2001-08-21 AU AU8402601A patent/AU8402601A/xx active Pending
- 2001-08-21 BR BR0113637-2A patent/BR0113637A/pt not_active IP Right Cessation
- 2001-08-21 MX MXPA03001721A patent/MXPA03001721A/es active IP Right Grant
- 2001-08-21 HR HR20030126A patent/HRP20030126B1/xx not_active IP Right Cessation
- 2001-08-21 PL PL01366630A patent/PL366630A1/xx not_active Application Discontinuation
- 2001-08-21 CZ CZ2003584A patent/CZ2003584A3/cs unknown
- 2001-08-21 NZ NZ523989A patent/NZ523989A/en unknown
- 2001-08-21 RU RU2003107921/04A patent/RU2239642C1/ru not_active IP Right Cessation
- 2001-08-21 SI SI200130703T patent/SI1315750T1/sl unknown
- 2001-08-21 WO PCT/EP2001/009630 patent/WO2002018437A2/fr not_active Ceased
- 2001-08-21 DK DK01962958T patent/DK1315750T3/da active
- 2001-08-21 AT AT01962958T patent/ATE353918T1/de active
- 2001-08-23 JO JO2001138A patent/JO2454B1/en active
- 2001-08-27 US US09/939,966 patent/US7045591B2/en not_active Expired - Fee Related
- 2001-08-28 PA PA20018527201A patent/PA8527201A1/es unknown
- 2001-08-28 AR ARP010104096A patent/AR030504A1/es active IP Right Grant
- 2001-08-28 PE PE2001000859A patent/PE20020483A1/es not_active Application Discontinuation
- 2001-08-28 MY MYPI20014025A patent/MY137457A/en unknown
- 2001-08-30 TW TW090121400A patent/TWI248941B/zh not_active IP Right Cessation
2003
- 2003-02-05 ZA ZA200301015A patent/ZA200301015B/en unknown
- 2003-02-20 IL IL154575A patent/IL154575A/en not_active IP Right Cessation
- 2003-02-27 MA MA27059A patent/MA27681A1/fr unknown
- 2003-02-27 NO NO20030916A patent/NO20030916D0/no not_active Application Discontinuation
- 2003-03-06 EC EC2003004503A patent/ECSP034503A/es unknown
2007
- 2007-05-07 CY CY20071100594T patent/CY1106562T1/el unknown
- 2007-05-30 AR ARP070102336A patent/AR061422A2/es unknown

Also Published As

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

Publication	Publication Date	Title
ZA200301015B (en)	2004-05-05	Selective cyclic peptides.
JP5965520B2 (ja)	2016-08-03	メラノコルチン受容体リガンド
AU783718B2 (en)	2005-12-01	Compositions and methods for treatment of sexual dysfunction
RU2381233C2 (ru)	2010-02-10	Агонисты рецептора меланокортина
US20050124553A1 (en)	2005-06-09	Peptide compositions for treatment of sexual dysfunction
US20100121027A1 (en)	2010-05-13	Cyclic Peptide Compositions for Treatment of Sexual Dysfunction
TW458958B (en)	2001-10-11	Compound with growth hormone releasing properties
CA1268597A (fr)	1990-05-01	Derives de diamino-acide
EP0417454A2 (fr)	1991-03-20	Analogues de LHRH à dimension réduite
EP2473518B1 (fr)	2017-02-22	Ligands de mélanocortine stabilisés
US7307063B2 (en)	2007-12-11	Melanocortin metallopeptides for treatment of sexual dysfunction
WO2007139921A2 (fr)	2007-12-06	N-oxydes de peptides de récepteurs de kappa-opioïdes
CA2271788A1 (fr)	1998-05-22	Analogues de peptide yy et leurs utilisations
JP2008505915A (ja)	2008-02-28	悪液質を治療するための環状ペプチド
JP2008505917A (ja)	2008-02-28	悪液質を治療するための環状ペプチド
AU602657B2 (en)	1990-10-25	Therapeutic somatostatin analogs
US8247530B2 (en)	2012-08-21	N-alkylated cyclic peptide melanocortin agonists
Bednarek et al.	2004	Ligands of the melanocortin receptors, 2002–2003 update
US6228841B1 (en)	2001-05-08	Peptide derivatives
JPS61293999A (ja)	1986-12-24	バソプレシン拮抗剤
AU2012592A (en)	1993-01-08	Immunoregulatory and neuroregulatory pentapeptides
US7754691B1 (en)	2010-07-13	Linear melanocortin receptor-specific peptides for cachexia
WO2002000688A1 (fr)	2002-01-03	Compose peptidique, compositions pharmaceutiques et medicaments contenant ceux-ci comme principe actif