JP2004507558A5 - - Google Patents
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- JP2004507558A5 JP2004507558A5 JP2002523951A JP2002523951A JP2004507558A5 JP 2004507558 A5 JP2004507558 A5 JP 2004507558A5 JP 2002523951 A JP2002523951 A JP 2002523951A JP 2002523951 A JP2002523951 A JP 2002523951A JP 2004507558 A5 JP2004507558 A5 JP 2004507558A5
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- JP
- Japan
- Prior art keywords
- hydrogen
- carbon atoms
- lys
- compound according
- asp
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 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 18
- 108010092854 aspartyllysine Proteins 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 53
- 239000001257 hydrogen Substances 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 43
- 125000004432 carbon atom Chemical group C* 0.000 claims 37
- 125000000217 alkyl group Chemical group 0.000 claims 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 102000001796 Melanocortin 4 receptors Human genes 0.000 claims 2
- OZILORBBPKKGRI-RYUDHWBXSA-N Phe-Arg Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 OZILORBBPKKGRI-RYUDHWBXSA-N 0.000 claims 2
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 108010018625 phenylalanylarginine Proteins 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 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 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 108010004073 cysteinylcysteine Proteins 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- -1 5- Methylamino-2-aminotetralin-2-carboxylic acid Chemical compound 0.000 description 6
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- RWLSBXBFZHDHHX-VIFPVBQESA-N (2s)-2-(naphthalen-2-ylamino)propanoic acid Chemical compound C1=CC=CC2=CC(N[C@@H](C)C(O)=O)=CC=C21 RWLSBXBFZHDHHX-VIFPVBQESA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- XHBDUHFCJSMXIU-UHFFFAOYSA-N 1-amino-4-(3-methoxyphenyl)cyclohexane-1-carboxylic acid Chemical compound COC1=CC=CC(C2CCC(N)(CC2)C(O)=O)=C1 XHBDUHFCJSMXIU-UHFFFAOYSA-N 0.000 description 1
- JYFVOJODHSMLNN-UHFFFAOYSA-N 1-amino-4-(4-ethoxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C1CCC(N)(C(O)=O)CC1 JYFVOJODHSMLNN-UHFFFAOYSA-N 0.000 description 1
- NHESZUWTJISWMW-UHFFFAOYSA-N 1-amino-4-(4-hydroxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(N)(C(O)=O)CCC1C1=CC=C(O)C=C1 NHESZUWTJISWMW-UHFFFAOYSA-N 0.000 description 1
- MTBXEODIGPQIDZ-UHFFFAOYSA-N 1-amino-4-(4-methoxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1CCC(N)(C(O)=O)CC1 MTBXEODIGPQIDZ-UHFFFAOYSA-N 0.000 description 1
- ZIZOGQRCTIPNGS-UHFFFAOYSA-N 1-amino-4-(4-methylphenyl)cyclohexane-1-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1CCC(N)(C(O)=O)CC1 ZIZOGQRCTIPNGS-UHFFFAOYSA-N 0.000 description 1
- OUHFMUCLEQWCAV-UHFFFAOYSA-N 1-amino-4-cyclohexylcyclohexane-1-carboxylic acid Chemical compound C1CC(N)(C(O)=O)CCC1C1CCCCC1 OUHFMUCLEQWCAV-UHFFFAOYSA-N 0.000 description 1
- XOKJVJPRWMSSRV-UHFFFAOYSA-N 1-azaniumyl-4-(4-chlorophenyl)cyclohexane-1-carboxylate Chemical compound C1CC(N)(C(O)=O)CCC1C1=CC=C(Cl)C=C1 XOKJVJPRWMSSRV-UHFFFAOYSA-N 0.000 description 1
- TWAYLYPZRSXEOS-UHFFFAOYSA-N 1-azaniumyl-4-phenylcyclohexane-1-carboxylate Chemical compound C1CC(N)(C(O)=O)CCC1C1=CC=CC=C1 TWAYLYPZRSXEOS-UHFFFAOYSA-N 0.000 description 1
- FRYOUKNFWFXASU-UHFFFAOYSA-N 2-(methylamino)acetic acid Chemical compound CNCC(O)=O.CNCC(O)=O FRYOUKNFWFXASU-UHFFFAOYSA-N 0.000 description 1
- VZKGHJWZNXLHGL-UHFFFAOYSA-N 2-amino-5-bromo-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1=CC=C2CC(N)(C(O)=O)CCC2=C1Br VZKGHJWZNXLHGL-UHFFFAOYSA-N 0.000 description 1
- QJJJBCCHEJIXRN-UHFFFAOYSA-N 2-amino-5-chloro-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1=CC=C2CC(N)(C(O)=O)CCC2=C1Cl QJJJBCCHEJIXRN-UHFFFAOYSA-N 0.000 description 1
- TZOUVKFDSMHCDO-UHFFFAOYSA-N 2-amino-5-ethoxy-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2OCC TZOUVKFDSMHCDO-UHFFFAOYSA-N 0.000 description 1
- YWHHZSRATCCCFB-UHFFFAOYSA-N 2-amino-5-ethyl-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2CC YWHHZSRATCCCFB-UHFFFAOYSA-N 0.000 description 1
- BBLVLRHQGNQNEH-UHFFFAOYSA-N 2-amino-5-methoxy-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2OC BBLVLRHQGNQNEH-UHFFFAOYSA-N 0.000 description 1
- UGXYLCUDHNGECR-UHFFFAOYSA-N 2-amino-5-methyl-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2C UGXYLCUDHNGECR-UHFFFAOYSA-N 0.000 description 1
- BJRDIGNYMJTPGG-UHFFFAOYSA-N 2-amino-5-propan-2-yl-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2C(C)C BJRDIGNYMJTPGG-UHFFFAOYSA-N 0.000 description 1
- ACQBYUJUBTYSFF-UHFFFAOYSA-N 2-amino-5-propan-2-yloxy-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound C1C(N)(C(O)=O)CCC2=C1C=CC=C2OC(C)C ACQBYUJUBTYSFF-UHFFFAOYSA-N 0.000 description 1
- CDULPPOISZOUTK-UHFFFAOYSA-N 2-azaniumyl-3,4-dihydro-1h-naphthalene-2-carboxylate Chemical compound C1=CC=C2CC(N)(C(O)=O)CCC2=C1 CDULPPOISZOUTK-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- GSWYUZQBLVUEPH-UHFFFAOYSA-N 3-(azaniumylmethyl)benzoate Chemical compound NCC1=CC=CC(C(O)=O)=C1 GSWYUZQBLVUEPH-UHFFFAOYSA-N 0.000 description 1
- PECYZEOJVXMISF-UWTATZPHSA-N 3-amino-D-alanine Chemical compound NC[C@@H](N)C(O)=O PECYZEOJVXMISF-UWTATZPHSA-N 0.000 description 1
- PECYZEOJVXMISF-REOHCLBHSA-N 3-amino-L-alanine Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 description 1
- OQSHSLCHNWPCHO-UHFFFAOYSA-N 4-amino-1-(2-methylphenyl)piperidine-4-carboxylic acid Chemical compound CC1=CC=CC=C1N1CCC(N)(C(O)=O)CC1 OQSHSLCHNWPCHO-UHFFFAOYSA-N 0.000 description 1
- QJKFHKJVNHAADI-UHFFFAOYSA-N 4-amino-1-(2-propan-2-yloxyphenyl)piperidine-4-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1N1CCC(N)(C(O)=O)CC1 QJKFHKJVNHAADI-UHFFFAOYSA-N 0.000 description 1
- LPBXKPRVUOLGGX-UHFFFAOYSA-N 4-amino-1-(3-methoxyphenyl)piperidine-4-carboxylic acid Chemical compound COC1=CC=CC(N2CCC(N)(CC2)C(O)=O)=C1 LPBXKPRVUOLGGX-UHFFFAOYSA-N 0.000 description 1
- OPZDTJADUMAIOP-UHFFFAOYSA-N 4-amino-1-(3-methylphenyl)piperidine-4-carboxylic acid Chemical compound CC1=CC=CC(N2CCC(N)(CC2)C(O)=O)=C1 OPZDTJADUMAIOP-UHFFFAOYSA-N 0.000 description 1
- BJZMFQQWGQAXHI-UHFFFAOYSA-N 4-amino-1-(4-chlorophenyl)piperidine-4-carboxylic acid Chemical compound C1CC(N)(C(O)=O)CCN1C1=CC=C(Cl)C=C1 BJZMFQQWGQAXHI-UHFFFAOYSA-N 0.000 description 1
- DJNWXMMFBXAOLF-UHFFFAOYSA-N 4-amino-1-(4-methylphenyl)piperidine-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1N1CCC(N)(C(O)=O)CC1 DJNWXMMFBXAOLF-UHFFFAOYSA-N 0.000 description 1
- SFTGJHTVCZFZTF-UHFFFAOYSA-N 4-amino-1-(4-phenoxyphenyl)piperidine-4-carboxylic acid Chemical compound C1CC(N)(C(O)=O)CCN1C(C=C1)=CC=C1OC1=CC=CC=C1 SFTGJHTVCZFZTF-UHFFFAOYSA-N 0.000 description 1
- FPGAOFXYANTSRQ-UHFFFAOYSA-N 4-amino-1-phenylpiperidine-4-carboxylic acid Chemical compound C1CC(N)(C(O)=O)CCN1C1=CC=CC=C1 FPGAOFXYANTSRQ-UHFFFAOYSA-N 0.000 description 1
- OGNSCSPNOLGXSM-GSVOUGTGSA-N D-2,4-diaminobutyric acid Chemical compound NCC[C@@H](N)C(O)=O OGNSCSPNOLGXSM-GSVOUGTGSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 1
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22918400P | 2000-08-30 | 2000-08-30 | |
| PCT/EP2001/009630 WO2002018437A2 (en) | 2000-08-30 | 2001-08-21 | Cyclic peptides having melanocortin-4 receptor agonist activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004507558A JP2004507558A (ja) | 2004-03-11 |
| JP2004507558A5 true JP2004507558A5 (https=) | 2005-04-07 |
| JP4217069B2 JP4217069B2 (ja) | 2009-01-28 |
Family
ID=22860145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002523951A Expired - Fee Related JP4217069B2 (ja) | 2000-08-30 | 2001-08-21 | 選択的環状ペプチド |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US7045591B2 (https=) |
| EP (1) | EP1315750B1 (https=) |
| JP (1) | JP4217069B2 (https=) |
| KR (1) | KR100483300B1 (https=) |
| CN (1) | CN100491396C (https=) |
| AR (2) | AR030504A1 (https=) |
| AT (1) | ATE353918T1 (https=) |
| AU (2) | AU2001284026B2 (https=) |
| BR (1) | BR0113637A (https=) |
| CA (1) | CA2420058C (https=) |
| CY (1) | CY1106562T1 (https=) |
| CZ (1) | CZ2003584A3 (https=) |
| DE (1) | DE60126624T2 (https=) |
| DK (1) | DK1315750T3 (https=) |
| EC (1) | ECSP034503A (https=) |
| ES (1) | ES2280393T3 (https=) |
| HR (1) | HRP20030126B1 (https=) |
| HU (1) | HUP0303078A3 (https=) |
| IL (2) | IL154575A0 (https=) |
| JO (1) | JO2454B1 (https=) |
| MA (1) | MA27681A1 (https=) |
| MX (1) | MXPA03001721A (https=) |
| MY (1) | MY137457A (https=) |
| NO (1) | NO20030916L (https=) |
| NZ (1) | NZ523989A (https=) |
| PA (1) | PA8527201A1 (https=) |
| PE (1) | PE20020483A1 (https=) |
| PL (1) | PL366630A1 (https=) |
| PT (1) | PT1315750E (https=) |
| RU (1) | RU2239642C1 (https=) |
| SI (1) | SI1315750T1 (https=) |
| TW (1) | TWI248941B (https=) |
| WO (1) | WO2002018437A2 (https=) |
| YU (1) | YU15603A (https=) |
| ZA (1) | ZA200301015B (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1409521A2 (en) * | 2001-07-12 | 2004-04-21 | Merck & Co., Inc. | Cyclic peptides as potent and selective melanocortin-4 receptor agonists |
| CA2462200A1 (en) | 2001-08-10 | 2003-02-20 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
| 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 |
| 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 |
| US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
| WO2004005324A2 (en) | 2002-07-09 | 2004-01-15 | 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 |
| US7968548B2 (en) | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
| 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 |
| BRPI0409976A (pt) * | 2003-05-09 | 2006-05-09 | Novo Nordisk As | composto, métodos para retardar a progressão de igt diabetes do tipo 2, para retardar a progressão de diabetes do tipo 2 para diabetes que requer insulina, para tratar obesidade ou prevenir excesso de peso para regular o apetite para induzir saciedade, para prevenir ganho de peso após se ter tido sucesso em perder peso, para aumentar dispêndio de energia, para tratar uma doença ou estado e para tratar bulimia, composição farmacêutica, e, uso de um composto |
| CA2530024A1 (en) * | 2003-06-19 | 2005-01-06 | Eli Lilly And Company | Melanocortin receptor 4(mc4) agonists and their uses |
| WO2005000338A1 (en) * | 2003-06-19 | 2005-01-06 | Eli Lilly And Company | Uses of melanocortin-3 receptor (mc3r) agonist peptides |
| US7084111B2 (en) | 2003-06-23 | 2006-08-01 | University Of Florida Research Foundation, Inc. | Melanocortin receptor templates, peptides, and use thereof |
| EP1670815A2 (en) * | 2003-09-30 | 2006-06-21 | 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 |
| US20070123453A1 (en) * | 2004-03-29 | 2007-05-31 | Heiman Mark L | Uses of melanocortin-4 receptor (mc4r) agonist peptides administered by continuous 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 |
| EP1809665A2 (en) * | 2004-11-04 | 2007-07-25 | Novo Nordisk A/S | Mc4r selective peptides and their use in the treatment of obesity |
| 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 |
| EP1809666A2 (en) * | 2004-11-04 | 2007-07-25 | Novo Nordisk A/S | Peptides for use in the treating obesity |
| JP2008519009A (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 |
| CN101203527A (zh) * | 2005-05-31 | 2008-06-18 | 耶路撒冷希伯来大学伊森姆研究发展公司 | 主链环化的促黑皮质素激素（αMSH）类似物 |
| 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 |
| EP2125862A1 (en) * | 2006-12-29 | 2009-12-02 | F. Hoffmann-Roche AG | Methods for the synthesis of cyclic peptides |
| CN101605728B (zh) * | 2007-02-16 | 2013-07-24 | 3M创新有限公司 | 用于从水中去除含氟化合物的系统和方法 |
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| US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
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| US5858972A (en) | 1996-01-11 | 1999-01-12 | La Jolla Cancer Research Foundation | Antithrombotic agents and methods of use |
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