LU87496A1 - Nouveaux peptides de la somatostatine,leur preparation et leur utilisation comme medicaments - Google Patents
Nouveaux peptides de la somatostatine,leur preparation et leur utilisation comme medicaments Download PDFInfo
- Publication number
- LU87496A1 LU87496A1 LU87496A LU87496A LU87496A1 LU 87496 A1 LU87496 A1 LU 87496A1 LU 87496 A LU87496 A LU 87496A LU 87496 A LU87496 A LU 87496A LU 87496 A1 LU87496 A1 LU 87496A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- signifies
- residue
- formula
- phe
- thr
- Prior art date
Links
- 108010056088 Somatostatin Proteins 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 102000005157 Somatostatin Human genes 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 32
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229920001184 polypeptide Polymers 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 8
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 102000007079 Peptide Fragments Human genes 0.000 claims description 7
- 108010033276 Peptide Fragments Proteins 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 235000001014 amino acid Nutrition 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- -1 hydrogen) Re Chemical class 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000539 amino acid group Chemical group 0.000 claims description 5
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- IYKLZBIWFXPUCS-VIFPVBQESA-N (2s)-2-(naphthalen-1-ylamino)propanoic acid Chemical compound C1=CC=C2C(N[C@@H](C)C(O)=O)=CC=CC2=C1 IYKLZBIWFXPUCS-VIFPVBQESA-N 0.000 claims description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 229940124277 aminobutyric acid Drugs 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000011282 treatment Methods 0.000 description 15
- 102000018997 Growth Hormone Human genes 0.000 description 8
- 108010051696 Growth Hormone Proteins 0.000 description 8
- 239000000122 growth hormone Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- DZHDVYLBNKMLMB-ZFWWWQNUSA-N Trp-Lys Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CCCCN)C(O)=O)=CNC2=C1 DZHDVYLBNKMLMB-ZFWWWQNUSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010039966 Senile dementia Diseases 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 229910052500 inorganic mineral Chemical class 0.000 description 3
- 230000003780 keratinization Effects 0.000 description 3
- 239000011707 mineral Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- 206010000599 Acromegaly Diseases 0.000 description 2
- 206010059245 Angiopathy Diseases 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 208000002699 Digestive System Neoplasms Diseases 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000006809 Pancreatic Fistula Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 208000009311 VIPoma Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 230000003412 degenerative effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 229960005309 estradiol Drugs 0.000 description 2
- 229930182833 estradiol Natural products 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 208000030304 gastrointestinal bleeding Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- FQRURPFZTFUXEZ-MRVPVSSYSA-N (2s)-2,3,3,3-tetrafluoro-2-(n-fluoroanilino)propanoic acid Chemical compound OC(=O)[C@](F)(C(F)(F)F)N(F)C1=CC=CC=C1 FQRURPFZTFUXEZ-MRVPVSSYSA-N 0.000 description 1
- UWPXWOJLMYFRGY-VKHMYHEASA-N (2s)-2-(difluoroamino)-2,3,3-trifluoropropanoic acid Chemical group OC(=O)[C@](F)(C(F)F)N(F)F UWPXWOJLMYFRGY-VKHMYHEASA-N 0.000 description 1
- CCQGGCWKGAMHGT-KKMMWDRVSA-N (2s)-2-[(4-aminocyclohexyl)amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC1CCC(N)CC1 CCQGGCWKGAMHGT-KKMMWDRVSA-N 0.000 description 1
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 description 1
- 206010052097 Dawn phenomenon Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000008279 Dumping Syndrome Diseases 0.000 description 1
- 206010056474 Erythrosis Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010065713 Gastric Fistula Diseases 0.000 description 1
- 206010018404 Glucagonoma Diseases 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- MNQZXJOMYWMBOU-GSVOUGTGSA-N L-(-)-glyceraldehyde Chemical compound OC[C@H](O)C=O MNQZXJOMYWMBOU-GSVOUGTGSA-N 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033647 Pancreatitis acute Diseases 0.000 description 1
- 208000032395 Post gastric surgery syndrome Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010038934 Retinopathy proliferative Diseases 0.000 description 1
- 108050001286 Somatostatin Receptor Proteins 0.000 description 1
- 102000011096 Somatostatin receptor Human genes 0.000 description 1
- SRMCRCFPAXNTBI-ZDUSSCGKSA-N [(2R)-2-hexanoyloxy-3-oxopropyl] hexanoate Chemical compound C(CCCCC)(=O)O[C@@H](C=O)COC(CCCCC)=O SRMCRCFPAXNTBI-ZDUSSCGKSA-N 0.000 description 1
- VVJPPJXHUOINRS-ZETCQYMHSA-N [(2R)-3-oxo-2-propanoyloxypropyl] propanoate Chemical compound C(CC)(=O)O[C@@H](C=O)COC(CC)=O VVJPPJXHUOINRS-ZETCQYMHSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000003229 acute pancreatitis Diseases 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical group CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 208000002458 carcinoid tumor Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 206010022498 insulinoma Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 201000011116 pancreatic cholera Diseases 0.000 description 1
- 208000021255 pancreatic insulinoma Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 1
- MLDSDVASYUUDLT-UHFFFAOYSA-N tert-butyl n-(3-oxopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC=O MLDSDVASYUUDLT-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- C07K14/575—Hormones
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Biophysics (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Psychiatry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB888808442A GB8808442D0 (en) | 1988-04-11 | 1988-04-11 | Peptide derivatives |
GB8808442 | 1988-04-11 | ||
GB888826452A GB8826452D0 (en) | 1988-11-11 | 1988-11-11 | Peptide derivatives |
GB8826452 | 1988-11-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU87496A1 true LU87496A1 (fr) | 1989-11-14 |
Family
ID=26293760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU87496A LU87496A1 (fr) | 1988-04-11 | 1989-04-07 | Nouveaux peptides de la somatostatine,leur preparation et leur utilisation comme medicaments |
Country Status (14)
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100325972B1 (ko) * | 1993-08-09 | 2002-07-27 | 바이오메져 인코퍼레이티드 | 치료성펩타이드유도체 |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4139526A (en) * | 1977-12-01 | 1979-02-13 | Merck & Co., Inc. | Somatostatin analogs |
HUT42101A (en) * | 1985-01-07 | 1987-06-29 | Sandoz Ag | Process for preparing stomatostatine derivatives and pharmaceutical compositions containing such compounds |
JPH085913B2 (ja) * | 1985-09-12 | 1996-01-24 | ザ・アドミニストレ−タ−ズ・オブ・ザ・ツ−レイン・エデユケイシヨナル・フアンド | 治療用ソマトスタチン同族体 |
HU206890B (en) * | 1986-10-13 | 1993-01-28 | Sandoz Ag | Process for producing sugar-modified somatostatin peptide derivatives and pharmaceutical compositions containing them as active components |
-
1989
- 1989-04-03 DE DE3910667A patent/DE3910667A1/de not_active Withdrawn
- 1989-04-07 CH CH1301/89A patent/CH677795A5/de not_active IP Right Cessation
- 1989-04-07 GB GB8907902A patent/GB2224280B/en not_active Expired - Lifetime
- 1989-04-07 LU LU87496A patent/LU87496A1/fr unknown
- 1989-04-10 NL NL8900882A patent/NL8900882A/nl not_active Application Discontinuation
- 1989-04-10 SE SE8901278A patent/SE8901278L/ not_active Application Discontinuation
- 1989-04-10 DK DK171489A patent/DK171489A/da active Protection Beyond IP Right Term
- 1989-04-10 AU AU32639/89A patent/AU3263989A/en not_active Abandoned
- 1989-04-10 FR FR8904785A patent/FR2629824B1/fr not_active Expired - Fee Related
- 1989-04-10 IL IL89897A patent/IL89897A0/xx unknown
- 1989-04-10 BE BE8900400A patent/BE1003200A4/fr not_active IP Right Cessation
- 1989-04-10 IT IT8947833A patent/IT1231943B/it active
- 1989-04-10 JP JP1090507A patent/JPH01305098A/ja active Pending
- 1989-04-11 ES ES8901255A patent/ES2013431A6/es not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
FR2629824A1 (fr) | 1989-10-13 |
JPH01305098A (ja) | 1989-12-08 |
DK171489D0 (da) | 1989-04-10 |
NL8900882A (nl) | 1989-11-01 |
GB2224280B (en) | 1992-07-08 |
IT1231943B (it) | 1992-01-16 |
DE3910667A1 (de) | 1989-10-19 |
DK171489A (da) | 1989-10-12 |
IT8947833A0 (it) | 1989-04-10 |
CH677795A5 (enrdf_load_html_response) | 1991-06-28 |
SE8901278D0 (sv) | 1989-04-10 |
AU3263989A (en) | 1989-10-12 |
GB2224280A (en) | 1990-05-02 |
FR2629824B1 (fr) | 1995-03-10 |
ES2013431A6 (es) | 1990-05-01 |
IL89897A0 (en) | 1989-12-15 |
GB8907902D0 (en) | 1989-05-24 |
SE8901278L (sv) | 1989-10-12 |
BE1003200A4 (fr) | 1992-01-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
BE1003752A4 (fr) | Nouveaux derives peptidiques, leur preparation et leur utilisation comme medicaments. | |
BE1004357A4 (fr) | Nouveaux derives peptidiques, leur preparation et leur utilisation comme medicaments. | |
FR2501199A1 (fr) | Nouveaux polypeptides, leur preparation et leur application comme medicaments | |
LU87633A1 (fr) | Derives peptidiques | |
EP0676411A2 (fr) | Peptides et pseudopeptides dérivés de tachykinines, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
LU87262A1 (fr) | Nouveaux derives de la somatostatine,leur preparation et leur utilisation comme medicaments | |
JP2002542224A (ja) | Ii型糖尿病の治療薬としてのppar−(ガンマ)作用物質 | |
CH655936A5 (fr) | Derives du 3-amino pregn-5-ene, leurs sels, leur preparation, medicaments et compositions les renfermant. | |
CH634041A5 (fr) | Derives de la pepstatine, leur preparation et composition les contenant. | |
FR2658421A1 (fr) | Nouvelle utilisation therapeutique de peptides derives de la somatostatine. | |
FR2632188A1 (fr) | Nouvelle utilisation therapeutique d'analogues ou de derives de la somatostatine | |
BE1003200A4 (fr) | Nouveaux peptides de la somatostatine, leur preparation et leur utilisation comme medicaments. | |
FR2532308A1 (fr) | Nouveaux polypeptides, leur preparation et leur application comme medicaments | |
WO1988000594A1 (fr) | Tetrapeptide inhibiteur de l'entree en cycle des cellules souches hematopoietiques, procedes pour son obtention et ses applications | |
FR2522655A1 (fr) | Analogues de la somatostatine possedant une liaison du type hydrazide et medicaments en contenant | |
EP1140981B1 (fr) | Composes tripeptidiques utiles a titre d'inhibiteurs selectifs de l'aminopeptidase a et compositions pharmaceutiques correspondantes | |
FR2489320A1 (fr) | Nouveaux peptides anorexigenes | |
FR2548187A1 (fr) | Composes d'organo-germanium et leurs utilisations therapeutiques en tant qu'inhibiteurs des enzymes qui degradent les peptides opioides | |
FR2491922A1 (fr) | Nouveaux hexapeptides, procede pour leur preparation et application comme medicaments | |
FR2531952A1 (fr) | Analogues a forte activite gonadotrope du facteur liberant l'hormone luteinisante et l'hormone folliculostimulante et leur procede de preparation | |
EP0115227B1 (fr) | Nouveaux dérivés peptidiques, leur procédé de fabrication et leur utilisation pharmaceutique | |
BE839405A (fr) | Nouveaux polypeptides, leur preparation et leur application comme medicaments | |
EP0750635B1 (fr) | Peptides pour inhiber la liberation de pepsine | |
FR2521133A1 (fr) | Nouvel heptadecapeptide a effet de liberation d'hormone de croissance et medicament le contenant | |
FR2469395A1 (fr) | Nouveau cyclopeptide, sa preparation et les medicaments qui le contiennent |