CH665645A5 - Derives de dipeptides et leur procede de preparation. - Google Patents

Derives de dipeptides et leur procede de preparation. Download PDF

Info

Publication number: CH665645A5
Authority: CH; Switzerland
Prior art keywords: radical; general formula; acid; residue; anhydride
Prior art date: 1981-07-09

Application number

CH4514/81A

Other languages

English (en)

French (fr)

Inventor

Michel Flork

Original Assignee

Michel Flork

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.)

1981-07-09

Filing date

1981-07-09

Publication date

1988-05-31

1981-07-09 Application filed by Michel Flork filed Critical Michel Flork

1981-07-09 Priority to CH4514/81A priority Critical patent/CH665645A5/fr

1982-07-01 Priority to GR68622A priority patent/GR78088B/el

1982-07-07 Priority to DE8282401280T priority patent/DE3263121D1/de

1982-07-07 Priority to AT82401280T priority patent/ATE12768T1/de

1982-07-07 Priority to EP82401280A priority patent/EP0069674B1/fr

1982-07-08 Priority to EP82902071A priority patent/EP0083612A1/fr

1982-07-08 Priority to PCT/FR1982/000116 priority patent/WO1983000146A1/fr

1982-07-08 Priority to ES513829A priority patent/ES8306106A1/es

1982-07-09 Priority to JP57119677A priority patent/JPS5865214A/ja

1982-07-09 Priority to CA000406986A priority patent/CA1190243A/fr

1988-05-31 Publication of CH665645A5 publication Critical patent/CH665645A5/fr

Links

108010016626 Dipeptides Proteins 0.000 title claims abstract description 27
238000002360 preparation method Methods 0.000 title description 2
-1 N-acetyl amino Chemical group 0.000 claims abstract description 51
150000001413 amino acids Chemical class 0.000 claims abstract description 24
150000008064 anhydrides Chemical class 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 10
150000001735 carboxylic acids Chemical class 0.000 claims abstract 2
239000002253 acid Substances 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
230000009471 action Effects 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
239000012024 dehydrating agents‎ Substances 0.000 claims description 7
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000002609 medium Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
150000003949 imides Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
125000000539 amino acid group Chemical group 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
125000003047 N-acetyl group Chemical group 0.000 abstract description 29
150000001412 amines Chemical class 0.000 abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
230000008878 coupling Effects 0.000 abstract description 5
238000010168 coupling process Methods 0.000 abstract description 5
238000005859 coupling reaction Methods 0.000 abstract description 5
230000021736 acetylation Effects 0.000 abstract 1
238000006640 acetylation reaction Methods 0.000 abstract 1
230000005494 condensation Effects 0.000 abstract 1
238000009833 condensation Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
229940024606 amino acid Drugs 0.000 description 15
235000001014 amino acid Nutrition 0.000 description 15
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000013078 crystal Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011347 resin Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 8
229920002125 Sokalan® Polymers 0.000 description 8
235000004279 alanine Nutrition 0.000 description 8
229960003638 dopamine Drugs 0.000 description 8
229960002989 glutamic acid Drugs 0.000 description 7
239000004220 glutamic acid Substances 0.000 description 7
229960004502 levodopa Drugs 0.000 description 7
239000000203 mixture Substances 0.000 description 7
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 6
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
235000013922 glutamic acid Nutrition 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000005325 percolation Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OPVPGKGADVGKTG-BQBZGAKWSA-N Ac-Asp-Glu Chemical compound CC(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CCC(O)=O OPVPGKGADVGKTG-BQBZGAKWSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 3
MQUUQXIFCBBFDP-VKHMYHEASA-N N-formyl-L-aspartic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC=O MQUUQXIFCBBFDP-VKHMYHEASA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
229960005261 aspartic acid Drugs 0.000 description 3
235000003704 aspartic acid Nutrition 0.000 description 3
125000003164 beta-aspartyl group Chemical group 0.000 description 3
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
229960002885 histidine Drugs 0.000 description 3
239000007788 liquid Substances 0.000 description 3
OWOHWGNSBBGHTI-YFKPBYRVSA-N n-[(3s)-2,6-dioxooxan-3-yl]acetamide Chemical compound CC(=O)N[C@H]1CCC(=O)OC1=O OWOHWGNSBBGHTI-YFKPBYRVSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
239000002126 C01EB10 - Adenosine Substances 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
229960005305 adenosine Drugs 0.000 description 2
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 2
229960002449 glycine Drugs 0.000 description 2
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
229960000310 isoleucine Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
JMQITILRHSGUCB-BYPYZUCNSA-N n-[(3s)-2,5-dioxooxolan-3-yl]acetamide Chemical compound CC(=O)N[C@H]1CC(=O)OC1=O JMQITILRHSGUCB-BYPYZUCNSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
229940074569 salsolinol Drugs 0.000 description 2
IBRKLUSXDYATLG-UHFFFAOYSA-N salsolinol hydrobromide Natural products OC1=C(O)C=C2C(C)NCCC2=C1 IBRKLUSXDYATLG-UHFFFAOYSA-N 0.000 description 2
238000007790 scraping Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
QWWVBNODQCWBAZ-WHFBIAKZSA-N (2r)-2-amino-3-[(2r)-2-carboxy-2-(methylamino)ethyl]sulfanylpropanoic acid Chemical compound CN[C@H](C(O)=O)CSC[C@H](N)C(O)=O QWWVBNODQCWBAZ-WHFBIAKZSA-N 0.000 description 1
YYLQUHNPNCGKJQ-NHYDCYSISA-N (3R)-3-hydroxy-L-aspartic acid Chemical compound OC(=O)[C@@H](N)[C@@H](O)C(O)=O YYLQUHNPNCGKJQ-NHYDCYSISA-N 0.000 description 1
RFWFOJDAIRDAPK-VKHMYHEASA-N (3s)-3-aminooxane-2,6-dione Chemical compound N[C@H]1CCC(=O)OC1=O RFWFOJDAIRDAPK-VKHMYHEASA-N 0.000 description 1
FZOTUKLXXDJLEN-YFKPBYRVSA-N (4s)-4-amino-5-oxo-5-(2-sulfoethylamino)pentanoic acid Chemical compound OC(=O)CC[C@H](N)C(=O)NCCS(O)(=O)=O FZOTUKLXXDJLEN-YFKPBYRVSA-N 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 description 1
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
IBRKLUSXDYATLG-LURJTMIESA-N (S)-salsolinol Chemical compound OC1=C(O)C=C2[C@H](C)NCCC2=C1 IBRKLUSXDYATLG-LURJTMIESA-N 0.000 description 1
OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical class N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
ZOWYFYXTIWQBEP-UHFFFAOYSA-N 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxyisoquinoline Chemical compound C1=C(OCC)C(OCC)=CC=C1CC1=NC=CC2=CC(OCC)=C(OCC)C=C12 ZOWYFYXTIWQBEP-UHFFFAOYSA-N 0.000 description 1
RRPYHFHHVVWXIX-UHFFFAOYSA-N 1-aminopentan-2-one Chemical compound CCCC(=O)CN RRPYHFHHVVWXIX-UHFFFAOYSA-N 0.000 description 1
125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 1
GUCKKCMJTSNWCU-UHFFFAOYSA-N 2-[(3-acetamido-3-carboxypropanoyl)amino]pentanedioic acid Chemical compound CC(=O)NC(C(O)=O)CC(=O)NC(C(O)=O)CCC(O)=O GUCKKCMJTSNWCU-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MQUUQXIFCBBFDP-UHFFFAOYSA-N 2-formamidobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC=O MQUUQXIFCBBFDP-UHFFFAOYSA-N 0.000 description 1
VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
YHFXGBOUSIKGMZ-UHFFFAOYSA-N 3-(2-chloro-10-phenothiazinyl)-N-methyl-1-propanamine Chemical compound C1=C(Cl)C=C2N(CCCNC)C3=CC=CC=C3SC2=C1 YHFXGBOUSIKGMZ-UHFFFAOYSA-N 0.000 description 1
YDNMHDRXNOHCJH-UHFFFAOYSA-N 3-aminopyrrolidine-2,5-dione Chemical compound NC1CC(=O)NC1=O YDNMHDRXNOHCJH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HYUIDAKMNFQPTI-UHFFFAOYSA-N 4-(ethylamino)benzene-1,2-diol Chemical compound CCNC1=CC=C(O)C(O)=C1 HYUIDAKMNFQPTI-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
HMYJLVDKPJHJCF-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNC(C)C2=C1C=C(OC)C(OC)=C2 HMYJLVDKPJHJCF-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- 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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
- 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)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

CH4514/81A 1981-07-09 1981-07-09 Derives de dipeptides et leur procede de preparation. CH665645A5 (fr)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
CH4514/81A CH665645A5 (fr)	1981-07-09	1981-07-09	Derives de dipeptides et leur procede de preparation.
GR68622A GR78088B (2)	1981-07-09	1982-07-01
DE8282401280T DE3263121D1 (en)	1981-07-09	1982-07-07	Medicines containing an n-acyl-l-aspactyl-taurine
AT82401280T ATE12768T1 (de)	1981-07-09	1982-07-07	N-acyl-l-aspactyl-taurine enthaltende arzneimittel.
EP82401280A EP0069674B1 (fr)	1981-07-09	1982-07-07	Médicaments contenant une N-acyl-L-aspartyl-taurine
EP82902071A EP0083612A1 (fr)	1981-07-09	1982-07-08	Nouveaux derives de dipeptides, leur procede de preparation et leur emploi comme medicament
PCT/FR1982/000116 WO1983000146A1 (fr)	1981-07-09	1982-07-08	Nouveaux derives de dipeptides, leur procede de preparation et leur emploi comme medicament
ES513829A ES8306106A1 (es)	1981-07-09	1982-07-08	Procedimiento de preparacion de una n-acil-aspartil-taurina.
JP57119677A JPS5865214A (ja)	1981-07-09	1982-07-09	Ｎ−アシル−ｌ−アスパルチルタウリンを含有する医薬
CA000406986A CA1190243A (fr)	1981-07-09	1982-07-09	Medicament contenant une n-acyl-l-aspartyl-taurine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH4514/81A CH665645A5 (fr)	1981-07-09	1981-07-09	Derives de dipeptides et leur procede de preparation.

Publications (1)

Publication Number	Publication Date
CH665645A5 true CH665645A5 (fr)	1988-05-31

Family

ID=4277513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4514/81A CH665645A5 (fr)	1981-07-09	1981-07-09	Derives de dipeptides et leur procede de preparation.

Country Status (9)

Country	Link
EP (2)	EP0069674B1 (2)
JP (1)	JPS5865214A (2)
AT (1)	ATE12768T1 (2)
CA (1)	CA1190243A (2)
CH (1)	CH665645A5 (2)
DE (1)	DE3263121D1 (2)
ES (1)	ES8306106A1 (2)
GR (1)	GR78088B (2)
WO (1)	WO1983000146A1 (2)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2546407B1 (fr) *	1983-05-24	1986-04-18	Therapeutique Applic Sa	Medicament a activite anti-allergique pour administration locale a base d'acide n-acetyl(a,b)-aspartyl glutamique
IT1226552B (it) *	1988-07-29	1991-01-24	Ellem Ind Farmaceutica	Peptidi immunostimolanti.
ES2100222T3 (es) *	1990-07-19	1997-06-16	Nippon Zoki Pharmaceutical Co	Derivados del acido aminoalcansulfonico y compuestos farmaceuticos a utilizar para prevenir o tratar afecciones cardiacas.
AU5825094A (en) *	1993-11-19	1995-06-06	Astra Aktiebolag	Novel dipeptide derivatives
JP2002537307A (ja) *	1999-02-19	2002-11-05	ベー・エル・アー・ハー・エム・エス・ディアグノスティカ・ゲーエムベーハー	甲状腺機能亢進症の治療におけるブロッキング抗ｔｓｈレセプター抗体の使用およびかかる使用のためのモノクローナル抗体
TW200413283A (en) *	2002-08-27	2004-08-01	Asahi Chemical Ind	Novel composition containing acyl group
JP4847113B2 (ja) *	2005-11-30	2011-12-28	柳井紙工株式会社	組立て紙箱

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2257270A1 (en) *	1974-01-11	1975-08-08	Ferlux	CNS-Active N-acyl-asparagyl-glutamic acids and salts - prepd by reacting N-acyl aspartic acid with anhydride, then reaction with glutamic acid salt
IL47149A (en) *	1974-04-29	1979-05-31	Chinoin Gyogyszer Es Vegyeszet	Amino acid derivatives,their preparation and pharmaceutical compositions containing them

1981
- 1981-07-09 CH CH4514/81A patent/CH665645A5/fr not_active IP Right Cessation
1982
- 1982-07-01 GR GR68622A patent/GR78088B/el unknown
- 1982-07-07 DE DE8282401280T patent/DE3263121D1/de not_active Expired
- 1982-07-07 EP EP82401280A patent/EP0069674B1/fr not_active Expired
- 1982-07-07 AT AT82401280T patent/ATE12768T1/de not_active IP Right Cessation
- 1982-07-08 ES ES513829A patent/ES8306106A1/es not_active Expired
- 1982-07-08 EP EP82902071A patent/EP0083612A1/fr not_active Withdrawn
- 1982-07-08 WO PCT/FR1982/000116 patent/WO1983000146A1/fr not_active Ceased
- 1982-07-09 CA CA000406986A patent/CA1190243A/fr not_active Expired
- 1982-07-09 JP JP57119677A patent/JPS5865214A/ja active Pending

Also Published As

Publication number	Publication date
WO1983000146A1 (fr)	1983-01-20
GR78088B (2)	1984-09-26
CA1190243A (fr)	1985-07-09
ES513829A0 (es)	1983-05-01
ATE12768T1 (de)	1985-05-15
EP0069674B1 (fr)	1985-04-17
ES8306106A1 (es)	1983-05-01
EP0069674A1 (fr)	1983-01-12
EP0083612A1 (fr)	1983-07-20
DE3263121D1 (en)	1985-05-23
JPS5865214A (ja)	1983-04-18

Legal Events

Date	Code	Title	Description
1996-03-15	PL	Patent ceased

Publication	Publication Date	Title
CA1119177A (en)	1982-03-02	Compounds and method for alleviating angiotensin related hypertension
EP0038758B1 (fr)	1985-03-06	Dérivés d'acides aminés et leur application thérapeutique
EP0082088B1 (fr)	1986-04-02	Nouveaux dérivés d'aminoacides, et leur application thérapeutique
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