BE623243A - - Google Patents
Info
- Publication number
- BE623243A BE623243A BE623243DA BE623243A BE 623243 A BE623243 A BE 623243A BE 623243D A BE623243D A BE 623243DA BE 623243 A BE623243 A BE 623243A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- alanyl
- prolyl
- leucyl
- glycyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 229920001184 polypeptide Polymers 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 230000001681 protective Effects 0.000 claims description 10
- 239000004472 Lysine Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 230000001077 hypotensive Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 230000003000 nontoxic Effects 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001980 alanyl group Chemical group 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 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 claims description 3
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 150000001509 aspartic acid derivatives Chemical class 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- BLMPQMFVWMYDKT-NZTKNTHTSA-N Carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims 2
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
- 230000000261 vasodilator Effects 0.000 claims 2
- 239000003071 vasodilator agent Substances 0.000 claims 2
- SBMNPABNWKXNBJ-BQBZGAKWSA-N (2S)-6-amino-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CO SBMNPABNWKXNBJ-BQBZGAKWSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 claims 1
- NOQGZXFMHARMLW-UHFFFAOYSA-N Succinic acid 2,2-dimethylhydrazide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 230000002588 toxic Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 23
- 239000002904 solvent Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- -1 L-alanyl- Chemical group 0.000 description 7
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 7
- 229960002429 Proline Drugs 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Carbodicyclohexylimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 241000565118 Cordylophora caspia Species 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N Dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 2
- 229940021015 I.V. solution additive Amino Acids Drugs 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 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
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- 206010061529 Polyp Diseases 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001809 detectable Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000002633 protecting Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000002072 seryl group Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 201000010874 syndrome Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RLXSTJVYBMNHEP-UWVGGRQHSA-N (2S)-2-[(2-aminoacetyl)amino]-N-[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]-4-methylpentanamide Chemical compound CSCC[C@@H](C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)CN RLXSTJVYBMNHEP-UWVGGRQHSA-N 0.000 description 1
- XUXRXWLKUYPGMZ-UHFFFAOYSA-N 2-(tritylamino)acetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCC(=O)O)C1=CC=CC=C1 XUXRXWLKUYPGMZ-UHFFFAOYSA-N 0.000 description 1
- GSYTVXOARWSQSV-UHFFFAOYSA-N 2-amino-4-methylsulfanylbutanamide Chemical compound CSCCC(N)C(N)=O GSYTVXOARWSQSV-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229960003767 Alanine Drugs 0.000 description 1
- 206010001902 Amaurosis Diseases 0.000 description 1
- 206010002383 Angina pectoris Diseases 0.000 description 1
- 229960005261 Aspartic Acid Drugs 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920001429 Chelating resin Polymers 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 210000004351 Coronary Vessels Anatomy 0.000 description 1
- 210000003414 Extremities Anatomy 0.000 description 1
- 210000001105 Femoral Artery Anatomy 0.000 description 1
- 229960002989 Glutamic Acid Drugs 0.000 description 1
- 229960002449 Glycine Drugs 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010019233 Headache Diseases 0.000 description 1
- 229960000310 ISOLEUCINE Drugs 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-M L-isoleucinate Chemical compound CC[C@H](C)[C@H](N)C([O-])=O AGPKZVBTJJNPAG-WHFBIAKZSA-M 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N L-serine Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 101700008037 LYAR Proteins 0.000 description 1
- 210000000088 Lip Anatomy 0.000 description 1
- 229960004452 Methionine Drugs 0.000 description 1
- 206010027599 Migraine Diseases 0.000 description 1
- 208000008085 Migraine Disorders Diseases 0.000 description 1
- 210000002460 Muscle, Smooth Anatomy 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229960005190 Phenylalanine Drugs 0.000 description 1
- 208000003782 Raynaud Disease Diseases 0.000 description 1
- 206010037912 Raynaud's phenomenon Diseases 0.000 description 1
- 210000001525 Retina Anatomy 0.000 description 1
- 210000001210 Retinal Vessels Anatomy 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N Triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 206010068760 Ulcers Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 229910052614 beryl Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VTWRFRVMKPWCFL-UHFFFAOYSA-N diethyl phosphite Chemical compound CCOP([O-])OCC VTWRFRVMKPWCFL-UHFFFAOYSA-N 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 230000001631 hypertensive Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 125000001998 leucyl group Chemical group 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QVDXUKJJGUSGLS-UHFFFAOYSA-N methyl 2-amino-4-methylpentanoate Chemical compound COC(=O)C(N)CC(C)C QVDXUKJJGUSGLS-UHFFFAOYSA-N 0.000 description 1
- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
- KPNBUPJZFJCCIQ-LURJTMIESA-N methyl L-lysinate Chemical compound COC(=O)[C@@H](N)CCCCN KPNBUPJZFJCCIQ-LURJTMIESA-N 0.000 description 1
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 108010091886 peptide V Proteins 0.000 description 1
- 230000002093 peripheral Effects 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 125000000405 phenylalanyl group Chemical group 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000001148 spastic Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating Effects 0.000 description 1
- 230000024883 vasodilation Effects 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
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/22—Tachykinins, e.g. Eledoisins, Substance P; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE623243A true BE623243A (US06262066-20010717-C00315.png) |
Family
ID=195464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE623243D BE623243A (US06262066-20010717-C00315.png) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE623243A (US06262066-20010717-C00315.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415803A (en) * | 1963-03-01 | 1968-12-10 | Schering Ag | Hexa- and heptapeptides related to the c-terminal sequence of eledoisin |
| EP0190852A2 (en) * | 1985-01-31 | 1986-08-13 | Ajinomoto Co., Inc. | Dipeptide derivatives and antihypertensive drugs containing them |
-
0
- BE BE623243D patent/BE623243A/fr unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3415803A (en) * | 1963-03-01 | 1968-12-10 | Schering Ag | Hexa- and heptapeptides related to the c-terminal sequence of eledoisin |
| EP0190852A2 (en) * | 1985-01-31 | 1986-08-13 | Ajinomoto Co., Inc. | Dipeptide derivatives and antihypertensive drugs containing them |
| EP0190852A3 (en) * | 1985-01-31 | 1988-11-02 | Ajinomoto Co., Inc. | Dipeptide derivatives and antihypertensive drugs containing them |
| US4971993A (en) * | 1985-01-31 | 1990-11-20 | Ajinomoto Co., Inc. | Dipeptide derivatives and antihypertensive drugs containing them |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS643870B2 (US06262066-20010717-C00315.png) | ||
| JPS6059226B2 (ja) | プロリン誘導体および関連化合物 | |
| EP0082088A1 (fr) | Nouveaux dérivés d'aminoacides, et leur application thérapeutique | |
| EP0038758A1 (fr) | Dérivés d'acides aminés et leur application thérapeutique | |
| LU82316A1 (fr) | Mercaptoacyldipeptides a action anti-hypertensive | |
| FR2460291A1 (fr) | Nouveaux tripeptides agissant sur le systeme nerveux central et leur procede de preparation | |
| CH627734A5 (fr) | Procede de synthese de peptides modifies. | |
| CH653039A5 (fr) | Tri-, tetra- et pentapeptides, leur preparation et les medicaments qui les contiennent. | |
| FR2549051A1 (fr) | Nouveaux agents radioprotecteurs ayant une structure amino-thioalkyle et procede pour leur preparation | |
| FR2460292A1 (fr) | Nouveaux tripeptidamides actifs sur le systeme nerveux central et procede de preparation de ceux-ci | |
| FR2525215A1 (fr) | Analogues de la vasopressine | |
| EP0124420B1 (fr) | Nouveaux dérivés peptidiques inhibiteurs de la sécrétion gastrique, procédé pour leur préparation et médicaments les contenant | |
| DK149110B (da) | Analogifremgangsmaade til fremstilling af bestatin eller et analogt dipeptid samt alfa-hydroxy-beta-aminocarboxylsyrer til brug som udgangsforbindelser herfor | |
| BE623243A (US06262066-20010717-C00315.png) | ||
| EP0188947B1 (fr) | Peptides réduits, inhibiteurs de la sécrétion gastrique, procédé d'obtention et compositions pharmaceutiques les contenant | |
| FR2530238A1 (US06262066-20010717-C00315.png) | ||
| FR2516924A1 (fr) | Acides phosphinylalcanoyl- amines a action therapeutique | |
| EP0354108A1 (fr) | Amino-acides et peptides présentant un résidu tyrosine modifiée, leur préparation et leur application comme médicaments | |
| PT758342E (pt) | Nova substancia activa peptidica e sua preparacao | |
| BE814419R (fr) | (1-alpha-aminoisobutyryl)-corticotropines peptidiques | |
| JPH02209865A (ja) | ３―チオプロピオン酸誘導体の製造法 | |
| FR2508040A1 (fr) | Derives de proline, leur procede de preparation et medicament les contenant | |
| CH434286A (de) | Verfahren zur Herstellung eines neuen Hendekapeptids | |
| JPS6333361A (ja) | ジペプチド誘導体及びその製法並びに用途 | |
| BE568942A (US06262066-20010717-C00315.png) |
