DE2423390A1 - Pyroglutamylverbindungen mit antidepressiver wirkung und verfahren zu ihrer herstellung - Google Patents
Pyroglutamylverbindungen mit antidepressiver wirkung und verfahren zu ihrer herstellungInfo
- Publication number
- DE2423390A1 DE2423390A1 DE2423390A DE2423390A DE2423390A1 DE 2423390 A1 DE2423390 A1 DE 2423390A1 DE 2423390 A DE2423390 A DE 2423390A DE 2423390 A DE2423390 A DE 2423390A DE 2423390 A1 DE2423390 A1 DE 2423390A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally
- compounds
- acid
- carbon atoms
- branched alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 8
- 230000001430 anti-depressive effect Effects 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000006239 protecting group Chemical group 0.000 claims abstract description 7
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims abstract description 6
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 11
- 125000005518 carboxamido group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000002308 glutamine derivatives Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 alkyl radical Chemical class 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UICDNADSGVMHKL-ZETCQYMHSA-N (2s)-n-butyl-5-oxopyrrolidine-2-carboxamide Chemical compound CCCCNC(=O)[C@@H]1CCC(=O)N1 UICDNADSGVMHKL-ZETCQYMHSA-N 0.000 description 3
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DEPSACIPTIZHFP-QMMMGPOBSA-N (2,4,5-trichlorophenyl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound C1=C(Cl)C(Cl)=CC(Cl)=C1OC(=O)[C@H]1NC(=O)CC1 DEPSACIPTIZHFP-QMMMGPOBSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229940124277 aminobutyric acid Drugs 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
- GPOGKMPXBDGPJH-UHFFFAOYSA-N butan-2-yl acetate hydrochloride Chemical compound Cl.CCC(C)OC(C)=O GPOGKMPXBDGPJH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 description 1
- FMROFZXZHJKSRK-QMMMGPOBSA-N (2s)-5-oxo-n-pentylpyrrolidine-2-carboxamide Chemical compound CCCCCNC(=O)[C@@H]1CCC(=O)N1 FMROFZXZHJKSRK-QMMMGPOBSA-N 0.000 description 1
- CLNSLBYOSNFAOC-UHNVWZDZSA-N (2s)-n-[(2r)-1-amino-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound NC(=O)[C@@H](C)NC(=O)[C@@H]1CCC(=O)N1 CLNSLBYOSNFAOC-UHNVWZDZSA-N 0.000 description 1
- CLNSLBYOSNFAOC-WHFBIAKZSA-N (2s)-n-[(2s)-1-amino-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide Chemical compound NC(=O)[C@H](C)NC(=O)[C@@H]1CCC(=O)N1 CLNSLBYOSNFAOC-WHFBIAKZSA-N 0.000 description 1
- OMSBLEXGRIBBNL-VIFPVBQESA-N (2s)-n-hexyl-5-oxopyrrolidine-2-carboxamide Chemical compound CCCCCCNC(=O)[C@@H]1CCC(=O)N1 OMSBLEXGRIBBNL-VIFPVBQESA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- DAZRVKBSFHYTLI-GDVGLLTNSA-N 4-amino-2-[(2S)-5-oxopyrrolidine-2-carbonyl]butanoic acid Chemical compound NCCC(C(O)=O)C(=O)[C@@H]1CCC(=O)N1 DAZRVKBSFHYTLI-GDVGLLTNSA-N 0.000 description 1
- RWBBDSAYSNJJHM-UHFFFAOYSA-N 5-methyl-3-oxo-2-phenyl-1h-pyrazole-4-carbaldehyde Chemical compound O=C1C(C=O)=C(C)NN1C1=CC=CC=C1 RWBBDSAYSNJJHM-UHFFFAOYSA-N 0.000 description 1
- PASOSHLGESWRPG-MQWKRIRWSA-N 6-amino-2-[(2S)-5-oxopyrrolidine-2-carbonyl]hexanoic acid Chemical compound NCCCCC(C(O)=O)C(=O)[C@@H]1CCC(=O)N1 PASOSHLGESWRPG-MQWKRIRWSA-N 0.000 description 1
- 241001133287 Artocarpus hirsutus Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 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
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 108010086663 pyroglutamylalanine amide Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZVNLCOJFFYZPG-UHFFFAOYSA-N tert-butyl 4-aminobutanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CCCN CZVNLCOJFFYZPG-UHFFFAOYSA-N 0.000 description 1
- 230000001646 thyrotropic effect Effects 0.000 description 1
- PZSJOBKRSVRODF-UHFFFAOYSA-N vanillin acetate Chemical compound COC1=CC(C=O)=CC=C1OC(C)=O PZSJOBKRSVRODF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- 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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2423390A DE2423390A1 (de) | 1974-05-14 | 1974-05-14 | Pyroglutamylverbindungen mit antidepressiver wirkung und verfahren zu ihrer herstellung |
| IL47258A IL47258A (en) | 1974-05-14 | 1975-05-08 | Pyroglutamyl compounds having antidepressive activity and process for their manufacture |
| NL7505473A NL7505473A (nl) | 1974-05-14 | 1975-05-09 | Werkwijze voor het bereiden van pyroglutamylver- bindingen met antidepressieve werking. |
| CH608075A CH612180A5 (en) | 1974-05-14 | 1975-05-12 | Process for the preparation of novel pyroglutamyl compounds |
| LU72450A LU72450A1 (enrdf_load_stackoverflow) | 1974-05-14 | 1975-05-12 | |
| GB1984075A GB1472154A (en) | 1974-05-14 | 1975-05-12 | Pyroglutamyl compounds and process for their manufacture |
| CH85079A CH613689A5 (en) | 1974-05-14 | 1975-05-12 | Process for the preparation of novel pyroglutamyl compounds |
| IE1069/75A IE41145B1 (en) | 1974-05-14 | 1975-05-13 | Pyroglutamyl compounds and process for their manufacture |
| CA227,255A CA1064942A (en) | 1974-05-14 | 1975-05-13 | Pyroglutamy compounds having antidepressive activity and process for their manufacture |
| DK209575A DK209575A (da) | 1974-05-14 | 1975-05-13 | Pyroglutamylforbindelser med antidepressiv virkning og fremgangsmade til deres fremstilling |
| AT364875A AT352707B (de) | 1974-05-14 | 1975-05-13 | Verfahren zur herstellung von neuen pyroglutamylverbindungen |
| SE7505546A SE405113B (sv) | 1974-05-14 | 1975-05-14 | Forfarande for framstellning av pyroglutamylforeningar med antidepressiv verkan |
| JP50056232A JPS50157362A (enrdf_load_stackoverflow) | 1974-05-14 | 1975-05-14 | |
| FR7515026A FR2270866B1 (enrdf_load_stackoverflow) | 1974-05-14 | 1975-05-14 | |
| BE156337A BE829059A (fr) | 1974-05-14 | 1975-05-14 | Derives de pyroglutamyle leur procede de preparation et leurs applications |
| AT64078A AT357279B (de) | 1974-05-14 | 1978-01-30 | Verfahren zur herstellung von neuen pyroglutamylverbindungen |
| AT0013179A AT364875B (de) | 1974-05-14 | 1979-01-08 | Fluessiges reinigungsmittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2423390A DE2423390A1 (de) | 1974-05-14 | 1974-05-14 | Pyroglutamylverbindungen mit antidepressiver wirkung und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2423390A1 true DE2423390A1 (de) | 1975-12-04 |
Family
ID=5915523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2423390A Withdrawn DE2423390A1 (de) | 1974-05-14 | 1974-05-14 | Pyroglutamylverbindungen mit antidepressiver wirkung und verfahren zu ihrer herstellung |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1024134A4 (en) * | 1997-10-09 | 2003-05-14 | Ono Pharmaceutical Co | DERIVATIVES OF AMINOBUTANIC ACID |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3184395A (en) * | 1994-08-05 | 1996-03-04 | Warwick International Group Limited | Bleach activators |
| RU2232578C1 (ru) * | 2003-04-10 | 2004-07-20 | Ахапкина Валентина Ивановна | Вещество, обладающее антидепрессивной активностью |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5220996B2 (enrdf_load_stackoverflow) * | 1972-01-14 | 1977-06-07 | ||
| JPS5015793B2 (enrdf_load_stackoverflow) * | 1972-06-07 | 1975-06-07 |
-
1974
- 1974-05-14 DE DE2423390A patent/DE2423390A1/de not_active Withdrawn
-
1975
- 1975-05-08 IL IL47258A patent/IL47258A/xx unknown
- 1975-05-09 NL NL7505473A patent/NL7505473A/xx not_active Application Discontinuation
- 1975-05-12 CH CH608075A patent/CH612180A5/xx not_active IP Right Cessation
- 1975-05-12 CH CH85079A patent/CH613689A5/xx not_active IP Right Cessation
- 1975-05-12 LU LU72450A patent/LU72450A1/xx unknown
- 1975-05-12 GB GB1984075A patent/GB1472154A/en not_active Expired
- 1975-05-13 DK DK209575A patent/DK209575A/da not_active Application Discontinuation
- 1975-05-13 IE IE1069/75A patent/IE41145B1/xx unknown
- 1975-05-13 CA CA227,255A patent/CA1064942A/en not_active Expired
- 1975-05-13 AT AT364875A patent/AT352707B/de not_active IP Right Cessation
- 1975-05-14 JP JP50056232A patent/JPS50157362A/ja active Pending
- 1975-05-14 SE SE7505546A patent/SE405113B/xx unknown
- 1975-05-14 FR FR7515026A patent/FR2270866B1/fr not_active Expired
- 1975-05-14 BE BE156337A patent/BE829059A/xx not_active IP Right Cessation
-
1979
- 1979-01-08 AT AT0013179A patent/AT364875B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1024134A4 (en) * | 1997-10-09 | 2003-05-14 | Ono Pharmaceutical Co | DERIVATIVES OF AMINOBUTANIC ACID |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7505473A (nl) | 1975-11-18 |
| DK209575A (da) | 1975-11-15 |
| CH613689A5 (en) | 1979-10-15 |
| AT352707B (de) | 1979-10-10 |
| GB1472154A (en) | 1977-05-04 |
| BE829059A (fr) | 1975-11-14 |
| FR2270866A1 (enrdf_load_stackoverflow) | 1975-12-12 |
| IL47258A (en) | 1978-07-31 |
| IL47258A0 (en) | 1975-07-28 |
| ATA364875A (de) | 1979-03-15 |
| IE41145B1 (en) | 1979-10-24 |
| IE41145L (en) | 1975-11-14 |
| SE7505546L (sv) | 1975-11-17 |
| LU72450A1 (enrdf_load_stackoverflow) | 1977-02-09 |
| CH612180A5 (en) | 1979-07-13 |
| ATA13179A (de) | 1981-04-15 |
| SE405113B (sv) | 1978-11-20 |
| AT364875B (de) | 1979-03-15 |
| FR2270866B1 (enrdf_load_stackoverflow) | 1978-08-04 |
| JPS50157362A (enrdf_load_stackoverflow) | 1975-12-19 |
| CA1064942A (en) | 1979-10-23 |
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| 8130 | Withdrawal |