NL8501829A - Glutaminezuur- respectievelijk asparaginezuurderivaten, werkwijze voor de bereiding ervan alsmede de toepassing ervan in preparaten. - Google Patents
Glutaminezuur- respectievelijk asparaginezuurderivaten, werkwijze voor de bereiding ervan alsmede de toepassing ervan in preparaten. Download PDFInfo
- Publication number
- NL8501829A NL8501829A NL8501829A NL8501829A NL8501829A NL 8501829 A NL8501829 A NL 8501829A NL 8501829 A NL8501829 A NL 8501829A NL 8501829 A NL8501829 A NL 8501829A NL 8501829 A NL8501829 A NL 8501829A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- compounds
- compound
- activity
- treatment
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 10
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical class OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 103
- 238000011282 treatment Methods 0.000 claims description 32
- 241001465754 Metazoa Species 0.000 claims description 27
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 claims description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 229940107137 cholecystokinin Drugs 0.000 claims description 15
- 101800001982 Cholecystokinin Proteins 0.000 claims description 14
- 102100025841 Cholecystokinin Human genes 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 230000001663 anti-spastic effect Effects 0.000 claims description 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 239000000730 antalgic agent Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229940035676 analgesics Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- -1 morpholino, piperidino Chemical group 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
- 235000013922 glutamic acid Nutrition 0.000 claims description 5
- 230000004584 weight gain Effects 0.000 claims description 5
- 235000019786 weight gain Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 208000022531 anorexia Diseases 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 229960002989 glutamic acid Drugs 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 230000007246 mechanism Effects 0.000 claims description 3
- 210000002569 neuron Anatomy 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 239000002948 appetite stimulant Substances 0.000 claims description 2
- 229960005261 aspartic acid Drugs 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001989 choleretic effect Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940124641 pain reliever Drugs 0.000 claims 1
- 230000007119 pathological manifestation Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 description 29
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 26
- 229940079593 drug Drugs 0.000 description 17
- 239000003814 drug Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 230000000202 analgesic effect Effects 0.000 description 14
- 229960005181 morphine Drugs 0.000 description 13
- 241000700159 Rattus Species 0.000 description 12
- 238000010609 cell counting kit-8 assay Methods 0.000 description 12
- 108010087230 Sincalide Proteins 0.000 description 11
- 210000000232 gallbladder Anatomy 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000005303 weighing Methods 0.000 description 8
- 210000000941 bile Anatomy 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000003389 potentiating effect Effects 0.000 description 7
- 230000008602 contraction Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 5
- 229940127240 opiate Drugs 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 206010052747 Adenocarcinoma pancreas Diseases 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 208000002193 Pain Diseases 0.000 description 4
- 230000036407 pain Effects 0.000 description 4
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000234282 Allium Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 3
- 229960004193 dextropropoxyphene Drugs 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 102000001490 Opioid Peptides Human genes 0.000 description 2
- 108010093625 Opioid Peptides Proteins 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 210000002249 digestive system Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 201000002528 pancreatic cancer Diseases 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001228 trophic effect Effects 0.000 description 2
- UCFHLGYZODDCIJ-HACHORDNSA-N (2r)-2-benzamido-3,4-dichloropentanedioic acid Chemical compound OC(=O)C(Cl)C(Cl)[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 UCFHLGYZODDCIJ-HACHORDNSA-N 0.000 description 1
- PNCQTRSFSYUTDV-VIFPVBQESA-N (2s)-2-[(3,4-dichlorobenzoyl)amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 PNCQTRSFSYUTDV-VIFPVBQESA-N 0.000 description 1
- LHUMPWOBZPBWRA-VIFPVBQESA-N 3,4-dichloro-n-[(3s)-2,6-dioxooxan-3-yl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N[C@@H]1C(=O)OC(=O)CC1 LHUMPWOBZPBWRA-VIFPVBQESA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- BYBJDDZACMHGTC-UHFFFAOYSA-N 5-(dibutylamino)-4-[(3,4-dichlorobenzoyl)amino]-5-oxopentanoic acid Chemical compound CCCCN(CCCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 BYBJDDZACMHGTC-UHFFFAOYSA-N 0.000 description 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 description 1
- 101100383992 Arabidopsis thaliana CLC-C gene Proteins 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
- ZMAKCCXIFPCMEE-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOO ZMAKCCXIFPCMEE-UHFFFAOYSA-N 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000001164 bioregulatory effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000003754 cholecystokinin receptor blocking agent Substances 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- YDGWVHHYXBMDAD-UHFFFAOYSA-N ethyl formate;propan-2-one Chemical compound CC(C)=O.CCOC=O YDGWVHHYXBMDAD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960005195 morphine hydrochloride Drugs 0.000 description 1
- XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 210000003384 transverse colon Anatomy 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/66—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT67644/84A IT1178982B (it) | 1984-06-25 | 1984-06-25 | Derivati del acido gludamico aventi attivita antagonista su polipep tidi bioattivi e procedimento per la loro preparazione |
| IT6764484 | 1984-06-25 | ||
| IT6807084 | 1984-10-26 | ||
| IT68070/84A IT1196751B (it) | 1984-10-26 | 1984-10-26 | Alogeno e ciano derivati dell'acido glutammico ed aspartico ad attivita antagonista su polipeptidi bioattivi e procedimento per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8501829A true NL8501829A (nl) | 1986-01-16 |
Family
ID=26329809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8501829A NL8501829A (nl) | 1984-06-25 | 1985-06-25 | Glutaminezuur- respectievelijk asparaginezuurderivaten, werkwijze voor de bereiding ervan alsmede de toepassing ervan in preparaten. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4791215A (cs) |
| AT (1) | AT390949B (cs) |
| AU (1) | AU566601B2 (cs) |
| BE (1) | BE902726A (cs) |
| CA (1) | CA1325633C (cs) |
| CH (1) | CH674203A5 (cs) |
| DE (1) | DE3522506A1 (cs) |
| DK (1) | DK285685A (cs) |
| ES (1) | ES8604859A1 (cs) |
| FR (1) | FR2566397B1 (cs) |
| GB (1) | GB2160869B (cs) |
| IE (1) | IE57892B1 (cs) |
| NL (1) | NL8501829A (cs) |
| NZ (1) | NZ212436A (cs) |
| SE (1) | SE503111C2 (cs) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1215169B (it) * | 1985-12-17 | 1990-01-31 | Rotta Research Lab | Derivati alchil ossigenati degli acidi glutammico ed aspartico ad attivita antagonista su polipeptidi bioattivi e procedimento per la loro preparazione |
| IT1196849B (it) * | 1986-02-16 | 1988-11-25 | Rotta Research Lab | Nuovi derivati degli acidi 5 pentilammino 5 oxo pentaoico e 4 pentilammino 4 oxo butanoico ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| US4880938A (en) * | 1986-06-16 | 1989-11-14 | Merck & Co., Inc. | Amino acid analogs |
| US5089638A (en) * | 1986-06-16 | 1992-02-18 | Merck & Co., Inc. | Amino acid analogs as CCK-antagonists |
| IT1217123B (it) * | 1987-02-05 | 1990-03-14 | Rotta Research Lab | Derivati otticamente attivi dell acido 5 pentilammino 5 oxo pentanoico r ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| US4971978A (en) * | 1987-09-21 | 1990-11-20 | Nadzan Alex M | Derivatives of D-glutamic acid and D-aspartic acid |
| WO1990003399A1 (en) * | 1988-09-30 | 1990-04-05 | Australian Commercial Research & Development Limited | Amino acid transport proteins, amino acid analogues, assay apparatus, uses thereof for treatment and diagnosis of cancer |
| FR2643371B1 (fr) * | 1989-02-17 | 1993-11-05 | Roussel Uclaf | Nouveaux derives de l'acide 2-amino pentanedioique, leur procede de preparation et leur application comme medicaments |
| DK0411668T4 (da) * | 1989-08-04 | 1999-08-09 | Merck Sharp & Dohme | Central-chlolecystokinin-antagonister til behandling af psykiske forstyrrelser |
| IE912285A1 (en) * | 1990-07-12 | 1992-01-15 | Black James Foundation | Amino acid derivatives |
| IT1241029B (it) * | 1990-12-11 | 1993-12-27 | Rotta Research Lab | Derivati amidici biciclici e policiclici degli acidi glutammico, aspartico e 2-ammino adipico ad attivita' antigastrinica e procedimento per la loro preparazione |
| US5217957A (en) * | 1991-08-20 | 1993-06-08 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| US5153191A (en) * | 1991-08-20 | 1992-10-06 | Warner-Lambert Company | Cholecystokinin antagonists useful for treating depression |
| JPH07507993A (ja) * | 1991-12-20 | 1995-09-07 | メルク シヤープ エンド ドーム リミテツド | 医薬活性を有する中枢神経系コレシストキニンアンタゴニスト |
| US5716958A (en) * | 1994-10-27 | 1998-02-10 | Tobishi Pharmaceutical Co., Ltd. | Amino acid derivative having anti-CCK activity |
| GB9721746D0 (en) * | 1997-10-15 | 1997-12-10 | Panos Therapeutics Limited | Compositions |
| KR20120062681A (ko) * | 2003-11-27 | 2012-06-14 | 가부시키가이샤 시세이도 | 부전각화 억제제 및 피부 외용 조성물 |
| CN108912007B (zh) * | 2018-06-20 | 2021-02-26 | 中国农业科学院兰州畜牧与兽药研究所 | 一种右氯谷胺的制备方法 |
| CN110325052B (zh) * | 2018-11-05 | 2022-11-18 | 彭险峰 | 天门冬氨酸脂肪酰基衍生物在制备动物饲料添加剂中的应用 |
| EP3888471A4 (en) * | 2018-12-18 | 2021-12-22 | Peng, Xianfeng | USE OF A GLUTAMINE DERIVATIVE IN THE MANUFACTURE OF ANIMAL FEED ADDITIVE |
| WO2021028106A2 (en) * | 2019-08-15 | 2021-02-18 | Firmenich Sa | Taste-modifying compounds and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2828327A (en) * | 1953-12-17 | 1958-03-25 | Monsanto Chemicals | Esters of n-aroylaspartic acids |
| US3551419A (en) * | 1964-07-31 | 1970-12-29 | Rotta Research Lab | Amino acid amides and process for their production |
| JPS5111608B2 (cs) * | 1972-06-07 | 1976-04-13 |
-
1985
- 1985-06-17 NZ NZ212436A patent/NZ212436A/xx unknown
- 1985-06-17 IE IE1502/85A patent/IE57892B1/en not_active IP Right Cessation
- 1985-06-18 CA CA000484341A patent/CA1325633C/en not_active Expired - Fee Related
- 1985-06-18 US US06/746,065 patent/US4791215A/en not_active Expired - Lifetime
- 1985-06-19 GB GB08515555A patent/GB2160869B/en not_active Expired
- 1985-06-20 CH CH2617/85A patent/CH674203A5/it not_active IP Right Cessation
- 1985-06-20 SE SE8503097A patent/SE503111C2/sv not_active IP Right Cessation
- 1985-06-20 FR FR8509383A patent/FR2566397B1/fr not_active Expired
- 1985-06-21 BE BE0/215244A patent/BE902726A/fr not_active IP Right Cessation
- 1985-06-22 ES ES544462A patent/ES8604859A1/es not_active Expired
- 1985-06-24 DK DK285685A patent/DK285685A/da not_active Application Discontinuation
- 1985-06-24 DE DE19853522506 patent/DE3522506A1/de active Granted
- 1985-06-24 AU AU44109/85A patent/AU566601B2/en not_active Ceased
- 1985-06-24 AT AT0186985A patent/AT390949B/de not_active IP Right Cessation
- 1985-06-25 NL NL8501829A patent/NL8501829A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE503111C2 (sv) | 1996-03-25 |
| DE3522506C2 (cs) | 1988-03-10 |
| ES8604859A1 (es) | 1986-03-16 |
| ES544462A0 (es) | 1986-03-16 |
| DK285685A (da) | 1985-12-26 |
| AU4410985A (en) | 1986-01-02 |
| AT390949B (de) | 1990-07-25 |
| US4791215A (en) | 1988-12-13 |
| AU566601B2 (en) | 1987-10-22 |
| GB8515555D0 (en) | 1985-07-24 |
| BE902726A (fr) | 1985-10-16 |
| IE57892B1 (en) | 1993-05-05 |
| FR2566397A1 (fr) | 1985-12-27 |
| FR2566397B1 (fr) | 1988-08-05 |
| IE851502L (en) | 1985-12-22 |
| CH674203A5 (cs) | 1990-05-15 |
| DE3522506A1 (de) | 1986-01-02 |
| SE8503097D0 (sv) | 1985-06-20 |
| NZ212436A (en) | 1989-04-26 |
| DK285685D0 (da) | 1985-06-24 |
| CA1325633C (en) | 1993-12-28 |
| ATA186985A (de) | 1990-01-15 |
| GB2160869A (en) | 1986-01-02 |
| GB2160869B (en) | 1988-03-16 |
| SE8503097L (sv) | 1985-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8501829A (nl) | Glutaminezuur- respectievelijk asparaginezuurderivaten, werkwijze voor de bereiding ervan alsmede de toepassing ervan in preparaten. | |
| Sanger et al. | Ghrelin and motilin receptors as drug targets for gastrointestinal disorders | |
| JP2007536243A (ja) | ホスホリパーゼ−ａ２阻害薬を用いた、高コレステロール血症、高トリグリセリド血症、心臓血管疾患の治療 | |
| US5776972A (en) | Kappa-opiate agonists for inflammatory bowel disorders | |
| US9447040B2 (en) | Tricyclic compounds, compositions comprising them and uses thereof | |
| Delvaux | Pharmacology and clinical experience with fedotozine | |
| CN105636584A (zh) | 使用维生素b组合物促进胃肠系统动力的方法 | |
| WO2021198195A1 (en) | Agonist combination | |
| US20120071458A1 (en) | Methods for treating obesity | |
| CN114072147A (zh) | 使用葫芦巴碱和高蛋白质来预防或治疗骨骼肌病症或障碍的组合物和方法 | |
| Vu et al. | Discovery of benzothiazole derivatives as efficacious and enterocyte-specific MTP inhibitors | |
| Taniguchi et al. | Endogenous ghrelin and 5-HT regulate interdigestive gastrointestinal contractions in conscious rats | |
| JPH0543698B2 (cs) | ||
| CN119948050A (zh) | 用于治疗代谢和肝脏病症的组合物和方法 | |
| WO2021194152A1 (ko) | 섬유화 질환 치료용 복합 약학 조성물 | |
| CN104447611A (zh) | 阿考替胺化合物 | |
| Pustovit et al. | Muscarinic receptor 1 allosteric modulators stimulate colorectal emptying in dog, mouse and rat and resolve constipation | |
| CN114126630A (zh) | 使用葫芦巴碱和矿物质来预防或治疗骨骼肌病症或障碍的组合物和方法 | |
| US10568852B2 (en) | Combination compositions and their use in methods for treating obesity and obesity-related disorders | |
| WO2012167243A1 (en) | Compositions and methods of treatment for obesity | |
| CN108250219B (zh) | 一种治疗甲状腺炎的药物及其制备方法 | |
| WO2021194153A1 (ko) | 섬유화 질환 복합 치료제 개발 | |
| KR20220151044A (ko) | 바이구아나이드 약물을 이용한 대사 이상 동반된 mcp1 과도 활성 골관절염 질환 치료 주사 조성물 | |
| KR102357396B1 (ko) | 아스파탐의 새로운 용도 | |
| Zhang et al. | Physiological roles of ghrelin in the regulation of gastrointestinal motility in vertebrates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |