NZ524190A - Melanocortin receptor ligands - Google Patents

Melanocortin receptor ligands

Info

Publication number: NZ524190A
Authority: NZ; New Zealand
Prior art keywords: hydrogen; alkyl; ring; mmol; compound
Prior art date: 2000-09-27

Application number

NZ524190A

Other languages

English (en)

Inventor

Frank Hallock Ebetino

Adam W Mazur

Jeffrey Charles Hayes

Feng Wang

Mark Gregory Solinsky

Anny-Odile Colson

Qishen Lin

Original Assignee

Procter & Gamble

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.)

2000-09-27

Filing date

2001-09-26

Publication date

2004-09-24

2001-09-26 Application filed by Procter & Gamble filed Critical Procter & Gamble

2004-09-24 Publication of NZ524190A publication Critical patent/NZ524190A/en

Links

239000003446 ligand Substances 0.000 title description 13
108090000950 Melanocortin Receptors Proteins 0.000 title description 12
102000004378 Melanocortin Receptors Human genes 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims abstract description 215
125000003118 aryl group Chemical group 0.000 claims abstract description 69
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
125000001424 substituent group Chemical group 0.000 claims abstract description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
238000011282 treatment Methods 0.000 claims abstract description 14
208000035475 disorder Diseases 0.000 claims abstract description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 8
208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 7
206010028980 Neoplasm Diseases 0.000 claims abstract description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 4
230000036772 blood pressure Effects 0.000 claims abstract description 4
201000011510 cancer Diseases 0.000 claims abstract description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 3
208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 3
206010018429 Glucose tolerance impaired Diseases 0.000 claims abstract description 3
201000005569 Gout Diseases 0.000 claims abstract description 3
206010020112 Hirsutism Diseases 0.000 claims abstract description 3
206010020772 Hypertension Diseases 0.000 claims abstract description 3
206010022489 Insulin Resistance Diseases 0.000 claims abstract description 3
208000037093 Menstruation Disturbances Diseases 0.000 claims abstract description 3
208000030934 Restrictive pulmonary disease Diseases 0.000 claims abstract description 3
208000029078 coronary artery disease Diseases 0.000 claims abstract description 3
208000020694 gallbladder disease Diseases 0.000 claims abstract description 3
208000000509 infertility Diseases 0.000 claims abstract description 3
230000036512 infertility Effects 0.000 claims abstract description 3
231100000535 infertility Toxicity 0.000 claims abstract description 3
231100000544 menstrual irregularity Toxicity 0.000 claims abstract description 3
201000008482 osteoarthritis Diseases 0.000 claims abstract description 3
201000002859 sleep apnea Diseases 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims description 141
229910052739 hydrogen Inorganic materials 0.000 claims description 141
125000000217 alkyl group Chemical group 0.000 claims description 130
238000000034 method Methods 0.000 claims description 111
230000002829 reductive effect Effects 0.000 claims description 110
125000004432 carbon atom Chemical group C* 0.000 claims description 79
-1 cyano, amino Chemical group 0.000 claims description 77
150000002431 hydrogen Chemical group 0.000 claims description 67
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 54
125000000753 cycloalkyl group Chemical group 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
102100028701 General vesicular transport factor p115 Human genes 0.000 claims description 34
101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 claims description 34
125000003545 alkoxy group Chemical group 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 32
125000004404 heteroalkyl group Chemical group 0.000 claims description 30
125000004442 acylamino group Chemical group 0.000 claims description 29
125000002252 acyl group Chemical group 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 25
150000001336 alkenes Chemical class 0.000 claims description 24
125000001153 fluoro group Chemical group F* 0.000 claims description 23
125000004104 aryloxy group Chemical group 0.000 claims description 21
125000004429 atom Chemical group 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 21
125000005647 linker group Chemical group 0.000 claims description 21
150000001345 alkine derivatives Chemical class 0.000 claims description 20
150000002148 esters Chemical class 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
239000000546 pharmaceutical excipient Substances 0.000 claims description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000002837 carbocyclic group Chemical group 0.000 claims description 17
208000016261 weight loss Diseases 0.000 claims description 17
230000004580 weight loss Effects 0.000 claims description 16
125000004423 acyloxy group Chemical group 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 15
150000003573 thiols Chemical class 0.000 claims description 15
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
125000002619 bicyclic group Chemical group 0.000 claims description 14
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
150000001408 amides Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000002950 monocyclic group Chemical group 0.000 claims description 11
125000006413 ring segment Chemical group 0.000 claims description 11
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
241001465754 Metazoa Species 0.000 claims description 8
208000008589 Obesity Diseases 0.000 claims description 8
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000005035 acylthio group Chemical group 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
229930192474 thiophene Chemical group 0.000 claims description 7
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
238000005303 weighing Methods 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
102000001189 Cyclic Peptides Human genes 0.000 claims description 5
108010069514 Cyclic Peptides Proteins 0.000 claims description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 4
230000037396 body weight Effects 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
FGFBEHFJSQBISW-UHFFFAOYSA-N 1h-cyclopenta[b]pyridine Chemical compound C1=CNC2=CC=CC2=C1 FGFBEHFJSQBISW-UHFFFAOYSA-N 0.000 claims description 3
125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
125000005265 dialkylamine group Chemical group 0.000 claims description 3
150000003949 imides Chemical class 0.000 claims description 3
230000002611 ovarian Effects 0.000 claims description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 3
BGFHMYJZJZLMHW-UHFFFAOYSA-N 4-[2-[[2-(1-benzothiophen-3-yl)-9-propan-2-ylpurin-6-yl]amino]ethyl]phenol Chemical group N1=C(C=2C3=CC=CC=C3SC=2)N=C2N(C(C)C)C=NC2=C1NCCC1=CC=C(O)C=C1 BGFHMYJZJZLMHW-UHFFFAOYSA-N 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
208000001435 Thromboembolism Diseases 0.000 claims description 2
GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical group CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims description 2
208000022531 anorexia Diseases 0.000 claims description 2
210000000481 breast Anatomy 0.000 claims description 2
150000001923 cyclic compounds Chemical class 0.000 claims description 2
206010061428 decreased appetite Diseases 0.000 claims description 2
230000002357 endometrial effect Effects 0.000 claims description 2
210000000232 gallbladder Anatomy 0.000 claims description 2
210000002307 prostate Anatomy 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims 1
208000026310 Breast neoplasm Diseases 0.000 claims 1
206010008342 Cervix carcinoma Diseases 0.000 claims 1
206010009944 Colon cancer Diseases 0.000 claims 1
206010014733 Endometrial cancer Diseases 0.000 claims 1
206010014759 Endometrial neoplasm Diseases 0.000 claims 1
208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
206010033128 Ovarian cancer Diseases 0.000 claims 1
206010061535 Ovarian neoplasm Diseases 0.000 claims 1
206010060862 Prostate cancer Diseases 0.000 claims 1
208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
201000010881 cervical cancer Diseases 0.000 claims 1
208000029742 colonic neoplasm Diseases 0.000 claims 1
201000010175 gallbladder cancer Diseases 0.000 claims 1
239000007935 oral tablet Substances 0.000 claims 1
229940096978 oral tablet Drugs 0.000 claims 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 claims 1
201000010099 disease Diseases 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract 1
WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 231
239000000243 solution Substances 0.000 description 195
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 184
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 172
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 134
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
239000002904 solvent Substances 0.000 description 130
239000000203 mixture Substances 0.000 description 119
238000003786 synthesis reaction Methods 0.000 description 100
230000015572 biosynthetic process Effects 0.000 description 97
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 71
102000005962 receptors Human genes 0.000 description 67
108020003175 receptors Proteins 0.000 description 67
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 60
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 58
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 58
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
235000019439 ethyl acetate Nutrition 0.000 description 52
239000012043 crude product Substances 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
239000002253 acid Substances 0.000 description 44
239000000047 product Substances 0.000 description 43
108090000765 processed proteins & peptides Proteins 0.000 description 42
238000002953 preparative HPLC Methods 0.000 description 37
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 35
238000004007 reversed phase HPLC Methods 0.000 description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
239000013058 crude material Substances 0.000 description 33
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
239000000725 suspension Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
229940086542 triethylamine Drugs 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
229940024606 amino acid Drugs 0.000 description 29
238000002390 rotary evaporation Methods 0.000 description 29
235000001014 amino acid Nutrition 0.000 description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
238000003756 stirring Methods 0.000 description 27
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 26
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 26
238000003818 flash chromatography Methods 0.000 description 26
150000001413 amino acids Chemical class 0.000 description 25
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 25
239000012267 brine Substances 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
238000001914 filtration Methods 0.000 description 22
108010008364 Melanocortins Proteins 0.000 description 21
238000010168 coupling process Methods 0.000 description 21
230000008878 coupling Effects 0.000 description 20
238000005859 coupling reaction Methods 0.000 description 20
238000000746 purification Methods 0.000 description 20
239000000706 filtrate Substances 0.000 description 19
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
229910000041 hydrogen chloride Inorganic materials 0.000 description 19
239000002865 melanocortin Substances 0.000 description 19
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 19
229910052763 palladium Inorganic materials 0.000 description 19
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229910000029 sodium carbonate Inorganic materials 0.000 description 17
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
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NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 16
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APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 15
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NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 11
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 11
239000011347 resin Substances 0.000 description 11
229920005989 resin Polymers 0.000 description 11
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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238000010992 reflux Methods 0.000 description 10
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
- C—CHEMISTRY; METALLURGY
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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Health & Medical Sciences (AREA)
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Medicinal Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
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General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Diabetes (AREA)
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NZ524190A 2000-09-27 2001-09-26 Melanocortin receptor ligands NZ524190A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US23585800P	2000-09-27	2000-09-27
PCT/US2001/030051 WO2002026774A2 (en)	2000-09-27	2001-09-26	Melanocortin receptor ligands

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EP (1)	EP1409540A2 (de)
JP (1)	JP2004509974A (de)
KR (1)	KR100519204B1 (de)
CN (1)	CN1571796A (de)
AR (1)	AR030806A1 (de)
AU (2)	AU2001296313B2 (de)
BR (1)	BR0114257A (de)
CA (1)	CA2420045A1 (de)
CZ (1)	CZ2003788A3 (de)
HU (1)	HUP0303085A2 (de)
IL (1)	IL154437A0 (de)
MX (1)	MXPA03002691A (de)
NO (1)	NO20031287L (de)
NZ (1)	NZ524190A (de)
PE (1)	PE20020447A1 (de)
PL (1)	PL362003A1 (de)
RU (1)	RU2246501C2 (de)
WO (1)	WO2002026774A2 (de)
ZA (1)	ZA200301561B (de)

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US7176279B2 (en)	2000-06-28	2007-02-13	Palatin Technologies, Inc.	Cyclic peptide compositions and methods for treatment of sexual dysfunction
US7507568B2 (en)	2002-09-25	2009-03-24	The Proctor & Gamble Company	Three dimensional coordinates of HPTPbeta
US7226755B1 (en)	2002-09-25	2007-06-05	The Procter & Gamble Company	HPTPbeta as a target in treatment of angiogenesis mediated disorders
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ZA200301561B (en)	2004-03-10
IL154437A0 (en)	2003-09-17
NO20031287D0 (no)	2003-03-20
CN1571796A (zh)	2005-01-26
HUP0303085A2 (hu)	2003-12-29
JP2004509974A (ja)	2004-04-02
CZ2003788A3 (cs)	2003-08-13
EP1409540A2 (de)	2004-04-21
KR20030061814A (ko)	2003-07-22
MXPA03002691A (es)	2003-06-06
WO2002026774A2 (en)	2002-04-04
KR100519204B1 (ko)	2005-10-06
AR030806A1 (es)	2003-09-03
PE20020447A1 (es)	2002-07-02
RU2246501C2 (ru)	2005-02-20
BR0114257A (pt)	2003-07-01
AU9631301A (en)	2002-04-08
PL362003A1 (en)	2004-10-18
CA2420045A1 (en)	2002-04-04
WO2002026774A3 (en)	2003-03-27
NO20031287L (no)	2003-03-20
AU2001296313B2 (en)	2005-06-02

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