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
102100034216 Melanocyte-stimulating hormone receptor Human genes 0.000 description 5
101710161100 Melanocyte-stimulating hormone receptor Proteins 0.000 description 5
102000004378 Melanocortin Receptors Human genes 0.000 description 4
108090000950 Melanocortin Receptors Proteins 0.000 description 4
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
239000005556 hormone Substances 0.000 description 3
229940088597 hormone Drugs 0.000 description 3
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
108010069820 Pro-Opiomelanocortin Proteins 0.000 description 2
239000000683 Pro-Opiomelanocortin Substances 0.000 description 2
102100027467 Pro-opiomelanocortin Human genes 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 2
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
230000000638 stimulation Effects 0.000 description 2
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
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
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
101710115814 Adrenocorticotropic hormone receptor Proteins 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
101800000414 Corticotropin Proteins 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000009025 Endorphins Human genes 0.000 description 1
108010049140 Endorphins Proteins 0.000 description 1
102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229940126661 MC4 antagonist Drugs 0.000 description 1
102100023726 Melanocortin receptor 3 Human genes 0.000 description 1
101710085774 Melanocortin receptor 3 Proteins 0.000 description 1
102100023723 Melanocortin receptor 5 Human genes 0.000 description 1
101710085771 Melanocortin receptor 5 Proteins 0.000 description 1
108010008364 Melanocortins Proteins 0.000 description 1
239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 1
101710201349 Metallothionein B Proteins 0.000 description 1
102100031347 Metallothionein-2 Human genes 0.000 description 1
101710094505 Metallothionein-2 Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
101100274389 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chz-1 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010033307 Overweight Diseases 0.000 description 1
YQNBKXUTWBRQCS-BVSLBCMMSA-N Phe-Arg-Trp Chemical compound C([C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)C1=CC=CC=C1 YQNBKXUTWBRQCS-BVSLBCMMSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000270942 Rana pipiens Species 0.000 description 1
208000000453 Skin Neoplasms Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
108010042362 beta-Lipotropin Proteins 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000036541 health Effects 0.000 description 1
230000005802 health problem Effects 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000002865 melanocortin Substances 0.000 description 1
230000001802 melanotrophic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000010172 mouse model Methods 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
210000000211 third ventricle Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1

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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Toxicology (AREA)
Zoology (AREA)
Gastroenterology & Hepatology (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

Family

ID=22860145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200301015A ZA200301015B (en)	2000-08-30	2003-02-05	Selective cyclic peptides.

Country Status (35)

Country	Link
US (1)	US7045591B2 (cs)
EP (1)	EP1315750B1 (cs)
JP (1)	JP4217069B2 (cs)
KR (1)	KR100483300B1 (cs)
CN (1)	CN100491396C (cs)
AR (2)	AR030504A1 (cs)
AT (1)	ATE353918T1 (cs)
AU (2)	AU8402601A (cs)
BR (1)	BR0113637A (cs)
CA (1)	CA2420058C (cs)
CY (1)	CY1106562T1 (cs)
CZ (1)	CZ2003584A3 (cs)
DE (1)	DE60126624T2 (cs)
DK (1)	DK1315750T3 (cs)
EC (1)	ECSP034503A (cs)
ES (1)	ES2280393T3 (cs)
HR (1)	HRP20030126B1 (cs)
HU (1)	HUP0303078A3 (cs)
IL (2)	IL154575A0 (cs)
JO (1)	JO2454B1 (cs)
MA (1)	MA27681A1 (cs)
MX (1)	MXPA03001721A (cs)
MY (1)	MY137457A (cs)
NO (1)	NO20030916L (cs)
NZ (1)	NZ523989A (cs)
PA (1)	PA8527201A1 (cs)
PE (1)	PE20020483A1 (cs)
PL (1)	PL366630A1 (cs)
PT (1)	PT1315750E (cs)
RU (1)	RU2239642C1 (cs)
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
US7456184B2 (en)	2003-05-01	2008-11-25	Palatin Technologies Inc.	Melanocortin receptor-specific compounds
WO2003013571A1 (en)	2001-08-10	2003-02-20	Palatin Technologies, Inc.	Peptidomimetics of biologically active metallopeptides
US7354923B2 (en)	2001-08-10	2008-04-08	Palatin Technologies, Inc.	Piperazine melanocortin-specific compounds
US7732451B2 (en)	2001-08-10	2010-06-08	Palatin Technologies, Inc.	Naphthalene-containing melanocortin receptor-specific small molecule
US7655658B2 (en)	2001-08-10	2010-02-02	Palatin Technologies, Inc.	Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds
US7718802B2 (en)	2001-08-10	2010-05-18	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
AU2003248888A1 (en)	2002-07-09	2004-01-23	Palatin Technologies, Inc.	Peptide composition for treatment of sexual dysfunction
US7727991B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific single acyl piperazine compounds
US7727990B2 (en)	2003-05-01	2010-06-01	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine and keto-piperazine compounds
US7968548B2 (en)	2003-05-01	2011-06-28	Palatin Technologies, Inc.	Melanocortin receptor-specific piperazine compounds with diamine groups
KR20060026011A (ko)	2003-05-09	2006-03-22	노보 노르디스크 에이/에스	비만 치료용 펩티드
AU2004235872A1 (en) *	2003-05-09	2004-11-18	Novo Nordisk A/S	Peptides for use in treating obesity
WO2005000338A1 (en) *	2003-06-19	2005-01-06	Eli Lilly And Company	Uses of melanocortin-3 receptor (mc3r) agonist peptides
EA200600055A1 (ru) *	2003-06-19	2006-08-25	Эли Лилли Энд Компани	Агонисты рецептора меланокортина 4 (мк4 ) и их применение
US7084111B2 (en)	2003-06-23	2006-08-01	University Of Florida Research Foundation, Inc.	Melanocortin receptor templates, peptides, and use thereof
JP2007532471A (ja)	2003-09-30	2007-11-15	ノボ　ノルディスク　アクティーゼルスカブ	新規メラノコルチンレセプターアゴニスト
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
MXPA06011521A (es) *	2004-04-08	2007-03-21	Astellas Pharma Inc	Compuesto ws 727713.
US7709484B1 (en)	2004-04-19	2010-05-04	Palatin Technologies, Inc.	Substituted melanocortin receptor-specific piperazine compounds
WO2006048452A2 (en) *	2004-11-04	2006-05-11	Novo Nordisk A/S	Peptides for use in treating of obesity
CN101052648A (zh) *	2004-11-04	2007-10-10	诺和诺德公司	用于治疗肥胖的新颖的肽类
WO2006048450A2 (en) *	2004-11-04	2006-05-11	Novo Nordisk A/S	Peptides for use in the treating obesity
US20080306008A1 (en) *	2004-11-04	2008-12-11	Nova Nordisk A/S	Peptides for Use in the Treatment of Obesity
CA2609951A1 (en) *	2005-05-31	2006-12-07	Yissum Research Development Company Of The Hebrew University Of Jerusale M	Backbone cyclized melanocortin stimulating hormone (.alpha.s) analogs
MX2007015819A (es) *	2005-06-13	2008-02-22	Nastech Pharm Co	Suministro de derivados peptidicos a traves de la mucosa.
US20080015304A1 (en)	2006-07-13	2008-01-17	Klaus Hintzer	Aqueous emulsion polymerization process for producing fluoropolymers
US20070015937A1 (en) *	2005-07-15	2007-01-18	3M Innovative Properties Company	Process for recovery of fluorinated carboxylic acid surfactants from exhaust gas
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
EP2132143B1 (en) *	2007-02-16	2012-12-26	3M Innovative Properties Company	System and process for the removal of fluorochemicals from water
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
CA2689016C (en)	2007-05-25	2014-08-12	Ipsen Pharma S.A.S.	Melanocortin receptor ligands modified with hydantoin
WO2009011261A1 (ja) *	2007-07-19	2009-01-22	Tokuyama Corporation	ヒダントイン環を有する化合物及びその製造方法
KR20120075500A (ko)	2008-03-27	2012-07-06	그뤼넨탈 게엠베하	치환된 4-아미노사이클로헥산 유도체
AU2009228637B2 (en) *	2008-03-27	2013-12-19	Grunenthal Gmbh	(Hetero-)aryl cyclohexane derivatives
AR072072A1 (es) *	2008-06-09	2010-08-04	Palatin Technologies Inc	Peptidos especificos del receptor de melanocortina para el tratamiento de la obesidad / 669
EP2300036B1 (en)	2008-06-09	2017-04-05	Palatin Technologies, Inc.	Melanocortin receptor-specific peptides for treatment of sexual dysfunction
BRPI1009644B1 (pt)	2009-06-08	2022-02-08	Palatin Technologies, Inc	Peptídeo cíclico ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica e uso da composição farmacêutica
UY32690A (es)	2009-06-08	2011-01-31	Astrazeneca Ab	Péptidos específicos para receptores de melanocortina
WO2010144341A2 (en)	2009-06-08	2010-12-16	Palatin Technologies, Inc.	Lactam-bridged melanocortin receptor-specific peptides
EP2504351A4 (en)	2009-11-23	2013-10-30	Palatin Technologies Inc	MELANOCORTIN-1 RECEPTOR-SPECIFIC LINEAR PEPTIDE
AU2010321738B2 (en)	2009-11-23	2016-07-14	Palatin Technologies, Inc.	Melanocortin-1 receptor-specific cyclic peptides
JP6622690B2 (ja)	2013-03-15	2019-12-18	リズム・ファーマシューティカルズ・インコーポレイテッド	ペプチド組成物
GB201416351D0 (en)	2014-09-16	2014-10-29	Shire Internat Gmbh	Heterocyclic derivatives
GB201416352D0 (en) *	2014-09-16	2014-10-29	Shire Internat Gmbh	Spirocyclic derivatives
CN107001440A (zh) *	2014-09-26	2017-08-01	拜耳制药股份公司	稳定化的肾上腺髓质素衍生物及其用途
WO2018074999A1 (en) *	2016-10-17	2018-04-26	The Arizona Board Of Regents On Behalf Of The University Of Arizona	Novel modulators of melanocortin receptors for the treatment of depression and anxiety
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
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
HK1044954B (en)	1999-03-29	2008-11-21	The Procter & Gamble Company	Melanocortin receptor ligands

2001
- 2001-08-21 PT PT01962958T patent/PT1315750E/pt unknown
- 2001-08-21 DE DE60126624T patent/DE60126624T2/de not_active Expired - Lifetime
- 2001-08-21 SI SI200130703T patent/SI1315750T1/sl unknown
- 2001-08-21 EP EP01962958A patent/EP1315750B1/en not_active Expired - Lifetime
- 2001-08-21 WO PCT/EP2001/009630 patent/WO2002018437A2/en not_active Ceased
- 2001-08-21 YU YU15603A patent/YU15603A/sh unknown
- 2001-08-21 KR KR10-2003-7002931A patent/KR100483300B1/ko not_active Expired - Fee Related
- 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 IL IL15457501A patent/IL154575A0/xx unknown
- 2001-08-21 AT AT01962958T patent/ATE353918T1/de active
- 2001-08-21 NZ NZ523989A patent/NZ523989A/en unknown
- 2001-08-21 CN CNB018150284A patent/CN100491396C/zh not_active Expired - Fee Related
- 2001-08-21 RU RU2003107921/04A patent/RU2239642C1/ru not_active IP Right Cessation
- 2001-08-21 DK DK01962958T patent/DK1315750T3/da active
- 2001-08-21 PL PL01366630A patent/PL366630A1/xx not_active Application Discontinuation
- 2001-08-21 MX MXPA03001721A patent/MXPA03001721A/es active IP Right Grant
- 2001-08-21 AU AU8402601A patent/AU8402601A/xx active Pending
- 2001-08-21 AU AU2001284026A patent/AU2001284026B2/en not_active Ceased
- 2001-08-21 CZ CZ2003584A patent/CZ2003584A3/cs unknown
- 2001-08-21 CA CA002420058A patent/CA2420058C/en not_active Expired - Fee Related
- 2001-08-21 ES ES01962958T patent/ES2280393T3/es not_active Expired - Lifetime
- 2001-08-21 HR HR20030126A patent/HRP20030126B1/xx not_active IP Right Cessation
- 2001-08-21 BR BR0113637-2A patent/BR0113637A/pt not_active IP Right Cessation
- 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 AR ARP010104096A patent/AR030504A1/es active IP Right Grant
- 2001-08-28 PE PE2001000859A patent/PE20020483A1/es not_active Application Discontinuation
- 2001-08-28 PA PA20018527201A patent/PA8527201A1/es unknown
- 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 NO NO20030916A patent/NO20030916L/no not_active Application Discontinuation
- 2003-02-27 MA MA27059A patent/MA27681A1/fr unknown
- 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
AU8402601A (en)	2002-03-13
DK1315750T3 (da)	2007-06-11
MXPA03001721A (es)	2003-05-27
CY1106562T1 (el)	2012-01-25
CN100491396C (zh)	2009-05-27
JP4217069B2 (ja)	2009-01-28
HUP0303078A3 (en)	2012-02-28
EP1315750A2 (en)	2003-06-04
PT1315750E (pt)	2007-05-31
TWI248941B (en)	2006-02-11
JO2454B1 (en)	2008-10-09
JP2004507558A (ja)	2004-03-11
AU2001284026B2 (en)	2007-03-01
MY137457A (en)	2009-01-30
HUP0303078A2 (hu)	2003-12-29
PA8527201A1 (es)	2002-04-25
KR100483300B1 (ko)	2005-04-15
CA2420058C (en)	2009-04-07
NZ523989A (en)	2004-08-27
ATE353918T1 (de)	2007-03-15
EP1315750B1 (en)	2007-02-14
KR20030061788A (ko)	2003-07-22
BR0113637A (pt)	2004-02-25
CZ2003584A3 (cs)	2003-08-13
AR061422A2 (es)	2008-08-27
NO20030916D0 (no)	2003-02-27
YU15603A (sh)	2006-05-25
HRP20030126B1 (en)	2009-01-31
PL366630A1 (en)	2005-02-07
WO2002018437A2 (en)	2002-03-07
ECSP034503A (es)	2003-04-25
HRP20030126A2 (en)	2005-10-31
PE20020483A1 (es)	2002-06-06
US20020143141A1 (en)	2002-10-03
CN1451017A (zh)	2003-10-22
MA27681A1 (fr)	2006-01-02
CA2420058A1 (en)	2002-03-07
DE60126624T2 (de)	2007-11-22
DE60126624D1 (de)	2007-03-29
NO20030916L (no)	2003-02-27
IL154575A0 (en)	2003-09-17
US7045591B2 (en)	2006-05-16
RU2239642C1 (ru)	2004-11-10
ES2280393T3 (es)	2007-09-16
AR030504A1 (es)	2003-08-20
IL154575A (en)	2008-12-29
SI1315750T1 (sl)	2007-06-30
WO2002018437A3 (en)	2002-06-06

Publication	Publication Date	Title
DE60038734T2 (de)	2009-07-02	Melanocortinrezeptor-liganden
JP4734411B2 (ja)	2011-07-27	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
AU783718B2 (en)	2005-12-01	Compositions and methods for treatment of sexual dysfunction
RU2381233C2 (ru)	2010-02-10	Агонисты рецептора меланокортина
JP4217069B2 (ja)	2009-01-28	選択的環状ペプチド
TW458958B (en)	2001-10-11	Compound with growth hormone releasing properties
EP2473518B1 (en)	2017-02-22	Stabilized melanocortin ligands
EP0417454A2 (en)	1991-03-20	Reduced size LHRH analogs
WO2007139921A2 (en)	2007-12-06	N-oxides of kappa opioid receptor peptides
US20040038897A1 (en)	2004-02-26	Melanocortin metallopeptides for treatment of sexual dysfunction
CA2271788A1 (en)	1998-05-22	Analogs of peptide yy and uses thereof
CA2573142A1 (en)	2006-02-09	Cyclic peptides for treatment of cachexia
US7345144B2 (en)	2008-03-18	Cyclic peptides for treatment of cachexia
AU602657B2 (en)	1990-10-25	Therapeutic somatostatin analogs
US8247530B2 (en)	2012-08-21	N-alkylated cyclic peptide melanocortin agonists
US6228841B1 (en)	2001-05-08	Peptide derivatives
JPS61293999A (ja)	1986-12-24	バソプレシン拮抗剤
CA2088664A1 (en)	1992-12-04	Immunoregulatory and neuroregulatory pentapeptides
US7754691B1 (en)	2010-07-13	Linear melanocortin receptor-specific peptides for cachexia
WO2002000688A1 (en)	2002-01-03	Peptide compound and pharmaceutical compositions and medicines containing the same as the active ingredient