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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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Animal Behavior & Ethology (AREA)
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Diabetes (AREA)
Toxicology (AREA)
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Obesity (AREA)
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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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JP (1)	JP4217069B2 (cs)
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CN (1)	CN100491396C (cs)
AR (2)	AR030504A1 (cs)
AT (1)	ATE353918T1 (cs)
AU (2)	AU2001284026B2 (cs)
BR (1)	BR0113637A (cs)
CA (1)	CA2420058C (cs)
CY (1)	CY1106562T1 (cs)
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DE (1)	DE60126624T2 (cs)
DK (1)	DK1315750T3 (cs)
EC (1)	ECSP034503A (cs)
ES (1)	ES2280393T3 (cs)
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HU (1)	HUP0303078A3 (cs)
IL (2)	IL154575A0 (cs)
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MA (1)	MA27681A1 (cs)
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PA (1)	PA8527201A1 (cs)
PE (1)	PE20020483A1 (cs)
PL (1)	PL366630A1 (cs)
PT (1)	PT1315750E (cs)
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SI (1)	SI1315750T1 (cs)
TW (1)	TWI248941B (cs)
WO (1)	WO2002018437A2 (cs)
YU (1)	YU15603A (cs)
ZA (1)	ZA200301015B (cs)

Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003006604A2 (en) *	2001-07-12	2003-01-23	Merck & Co., Inc.	Cyclic peptides as potent and selective melanocortin-4 receptor agonists
US7718802B2 (en)	2001-08-10	2010-05-18	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
US7732451B2 (en)	2001-08-10	2010-06-08	Palatin Technologies, Inc.	Naphthalene-containing melanocortin receptor-specific small molecule
CA2462200A1 (en)	2001-08-10	2003-02-20	Palatin Technologies, Inc.	Peptidomimetics of biologically active metallopeptides
US7655658B2 (en)	2001-08-10	2010-02-02	Palatin Technologies, Inc.	Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds
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
AU2003248888A1 (en)	2002-07-09	2004-01-23	Palatin Technologies, Inc.	Peptide composition for treatment of sexual dysfunction
US7968548B2 (en)	2003-05-01	2011-06-28	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine compounds with diamine groups
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
KR20060026011A (ko)	2003-05-09	2006-03-22	노보 노르디스크 에이/에스	비만 치료용 펩티드
JP2007524584A (ja) *	2003-05-09	2007-08-30	ノボ　ノルディスク　アクティーゼルスカブ	肥満の治療に使用するペプチド
WO2005000338A1 (en) *	2003-06-19	2005-01-06	Eli Lilly And Company	Uses of melanocortin-3 receptor (mc3r) agonist peptides
WO2005000339A2 (en) *	2003-06-19	2005-01-06	Eli Lilly And Company	Melanocortin receptor 4(mc4) agonists and their uses
US7084111B2 (en)	2003-06-23	2006-08-01	University Of Florida Research Foundation, Inc.	Melanocortin receptor templates, peptides, and use thereof
WO2005030797A2 (en) *	2003-09-30	2005-04-07	Novo Nordisk A/S	Melanocortin receptor agonists
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 (en) *	2004-03-29	2006-12-20	Eli Lilly And Company	Uses of melanocortin-4 receptor (mc4r) agonist peptides administered by continunous infusion
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 (en) *	2004-11-04	2007-07-25	Novo Nordisk A/S	Peptides for use in the treating obesity
WO2006048452A2 (en) *	2004-11-04	2006-05-11	Novo Nordisk A/S	Peptides for use in treating of obesity
WO2006048451A1 (en) *	2004-11-04	2006-05-11	Novo Nordisk A/S	Peptides for use in the treatment of obesity
JP2008519006A (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
EP1885743A1 (en) *	2005-05-31	2008-02-13	Yissum Research Development Company, of The Hebrew University of Jerusalem	BACKBONE CYCLIZED MELANOCORTIN STIMULATING HORMONE ( alpha S ) ANALOGS
US20090042790A1 (en) *	2005-06-13	2009-02-12	Nastech Pharmaceutical Company Inc.	Transmucosal delivery of peptide derivatives
US20080015304A1 (en)	2006-07-13	2008-01-17	Klaus Hintzer	Aqueous emulsion polymerization process for producing fluoropolymers
US7671112B2 (en) *	2005-07-15	2010-03-02	3M Innovative Properties Company	Method of making fluoropolymer dispersion
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
CN101573371A (zh) *	2006-12-29	2009-11-04	弗·哈夫曼-拉罗切有限公司	环肽类化合物的合成方法
BRPI0807109A2 (pt) *	2007-02-16	2014-05-06	3M Innovative Properties Co	Sistema e processo para a remoção de fluoroquiímicos da água
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
WO2008147556A2 (en) *	2007-05-25	2008-12-04	Ipsen Pharma S.A.S.	Melanocortin receptor ligands modified with hydantoin
EP2172459B1 (en)	2007-07-19	2014-03-19	Tokuyama Corporation	Compound having hydantoin ring and method of producing the same
CN103183630A (zh)	2008-03-27	2013-07-03	格吕伦塔尔有限公司	取代的4-氨基环己烷衍生物
AU2009228637B2 (en) *	2008-03-27	2013-12-19	Grunenthal Gmbh	(Hetero-)aryl cyclohexane derivatives
KR101687037B1 (ko)	2008-06-09	2016-12-15	팔라틴 테크놀로지스 인코포레이티드	성기능 장애 치료용 멜라노코르틴 수용체-특이적 펩티드
UY31877A (es) *	2008-06-09	2010-01-29	Palatin Technologies Inc	Péptidos específicos de los receptores de melanocortina para el tratamiento de la obesidad / 669
EA020959B1 (ru)	2009-06-08	2015-03-31	Палатин Текнолоджиз, Инк.	Пептиды, специфичные к меланокортиновым рецепторам
WO2010144341A2 (en)	2009-06-08	2010-12-16	Palatin Technologies, Inc.	Lactam-bridged melanocortin receptor-specific peptides
UY32690A (es)	2009-06-08	2011-01-31	Astrazeneca Ab	Péptidos específicos para receptores de melanocortina
EP2504352B1 (en)	2009-11-23	2018-11-14	Palatin Technologies, Inc.	Melanocortin-1 receptor-specific cyclic peptides
JP2013511554A (ja)	2009-11-23	2013-04-04	パラティンテクノロジーズ，インコーポレイテッド	メラノコルチン−１受容体特異的線状ペプチド
EP3450449A3 (en)	2013-03-15	2019-06-12	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
CA2962486A1 (en) *	2014-09-26	2016-03-31	Bayer Pharma Aktiengesellschaft	Stabilized adrenomedullin derivatives and use thereof
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
WO2017066754A1 (en)	2015-10-15	2017-04-20	The Arizona Board Of Regents On Behalf Of The University Of Arizona	Compositions and methods for the treatment of depression and anxiety
US10899793B2 (en)	2016-05-27	2021-01-26	Regents Of The University Of Minnesota	Melanocortin ligands and methods of use thereof
US20190255142A1 (en) *	2016-10-17	2019-08-22	Arizona Board Of Regents On Behalf Of The University Of Arizona	Novel modulators of melanocortin receptors for the treatment of depression and anxiety
US11124541B2 (en)	2016-10-18	2021-09-21	Regents Of The University Of Minnesota	Chimeric melanocortin ligands and methods of use thereof
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
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
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 (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5811391A (en)	1994-08-25	1998-09-22	Cytel Corporation	Cyclic CS-1 peptidomimetics, compositions and methods of using same
US5858972A (en)	1996-01-11	1999-01-12	La Jolla Cancer Research Foundation	Antithrombotic agents and methods of use
CA2368431C (en)	1999-03-29	2006-01-24	The Procter & Gamble Company	Melanocortin receptor ligands

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Also Published As

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

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
US7795378B2 (en)	2010-09-14	Peptide compositions for treatment of sexual dysfunction
US7897721B2 (en)	2011-03-01	Cyclic peptide compositions for treatment of sexual dysfunction
RU2381233C2 (ru)	2010-02-10	Агонисты рецептора меланокортина
TW458958B (en)	2001-10-11	Compound with growth hormone releasing properties
CA1268597A (en)	1990-05-01	Diamino acid derivatives
NZ516030A (en)	2004-10-29	Compositions and methods for treatment of sexual dysfunction using MSH analogs containing the sequence His-Phe-Arg-Trp
US8541545B2 (en)	2013-09-24	Stabilized melanocortin ligands
JP2004534851A (ja)	2004-11-18	メラノコルチン受容体に特異的な線状および環状ペプチド
US7307063B2 (en)	2007-12-11	Melanocortin metallopeptides for treatment of sexual dysfunction
US7342089B2 (en)	2008-03-11	Cyclic peptides for treatment for cachexia
DE69411342T2 (de)	1998-11-19	Polypeptid bombesin antagonisten
US8247530B2 (en)	2012-08-21	N-alkylated cyclic peptide melanocortin agonists
CA2271788A1 (en)	1998-05-22	Analogs of peptide yy and uses thereof
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
EP0222283A2 (de)	1987-05-20	Aminosäurederivate
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
US7754691B1 (en)	2010-07-13	Linear melanocortin receptor-specific peptides for cachexia
AU2012592A (en)	1993-01-08	Immunoregulatory and neuroregulatory pentapeptides
WO2002000688A1 (fr)	2002-01-03	Compose peptidique, compositions pharmaceutiques et medicaments contenant ceux-ci comme principe actif