JPH0473425B2 - - Google Patents
Info
- Publication number
- JPH0473425B2 JPH0473425B2 JP60140103A JP14010385A JPH0473425B2 JP H0473425 B2 JPH0473425 B2 JP H0473425B2 JP 60140103 A JP60140103 A JP 60140103A JP 14010385 A JP14010385 A JP 14010385A JP H0473425 B2 JPH0473425 B2 JP H0473425B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- formula
- alkyl group
- different
- mono
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 81
- -1 tri-substituted phenyl Chemical group 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 34
- 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 26
- 230000000202 analgesic effect Effects 0.000 claims description 19
- 101800001982 Cholecystokinin Proteins 0.000 claims description 16
- 102100025841 Cholecystokinin Human genes 0.000 claims description 16
- 229940107137 cholecystokinin Drugs 0.000 claims description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical class OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 229920001184 polypeptide Polymers 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 208000022531 anorexia Diseases 0.000 claims description 5
- 230000001773 anti-convulsant effect Effects 0.000 claims description 5
- 239000001961 anticonvulsive agent Substances 0.000 claims description 5
- 229960003965 antiepileptics Drugs 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 229960002989 glutamic acid Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000004584 weight gain Effects 0.000 claims description 4
- 235000019786 weight gain Nutrition 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 150000002306 glutamic acid derivatives Chemical class 0.000 claims description 3
- 210000002569 neuron Anatomy 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 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
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 238000003975 animal breeding Methods 0.000 claims 1
- 239000000731 choleretic agent Substances 0.000 claims 1
- 230000010534 mechanism of action Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 description 36
- 241000700159 Rattus Species 0.000 description 27
- 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 24
- 238000012360 testing method Methods 0.000 description 19
- 229940079593 drug Drugs 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- 229960005181 morphine Drugs 0.000 description 12
- 239000003193 general anesthetic agent Substances 0.000 description 11
- 108010087230 Sincalide Proteins 0.000 description 10
- 238000010609 cell counting kit-8 assay Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 229940035674 anesthetics Drugs 0.000 description 9
- 230000008602 contraction Effects 0.000 description 7
- 210000000232 gallbladder Anatomy 0.000 description 7
- 230000003389 potentiating effect Effects 0.000 description 7
- 108010092674 Enkephalins Proteins 0.000 description 6
- URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical class C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 230000003042 antagnostic effect Effects 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 210000000941 bile Anatomy 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000001595 contractor effect Effects 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 206010052747 Adenocarcinoma pancreas Diseases 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 210000002249 digestive system Anatomy 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 description 3
- 201000002528 pancreatic cancer Diseases 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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 2
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003754 cholecystokinin receptor blocking agent Substances 0.000 description 2
- 230000001989 choleretic effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001228 trophic effect Effects 0.000 description 2
- RJEUERNNQHNSKG-CCKFTAQKSA-N (2s)-2-amino-n-[(2r)-1-[[2-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide Chemical compound C([C@H](N)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 RJEUERNNQHNSKG-CCKFTAQKSA-N 0.000 description 1
- RZMLEWIGPJPYLQ-CISYKLKFSA-N (3s)-3-[[(2s)-2-[[(2s)-2-[[2-[[(2s)-2-amino-4-methylsulfanylbutanoyl]amino]acetyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)[C@@H](N)CCSC)C(N)=O)C1=CC=CC=C1 RZMLEWIGPJPYLQ-CISYKLKFSA-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
- 241000238876 Acari Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009471 action 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
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000011712 cell development Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 108010073383 cholecystokinin hexapeptide Proteins 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000003086 colorant Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 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 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 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
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 230000008558 metabolic pathway by substance 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 208000008443 pancreatic carcinoma Diseases 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
- 230000008569 process Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 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
- 235000012712 vegetable carbon Nutrition 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT67644A/84 | 1984-06-25 | ||
| 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 |
| IT68070A/84 | 1984-10-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6144855A JPS6144855A (ja) | 1986-03-04 |
| JPH0473425B2 true JPH0473425B2 (fr) | 1992-11-20 |
Family
ID=11304166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60140103A Granted JPS6144855A (ja) | 1984-06-25 | 1985-06-25 | 生物学的活性ポリペプチド類に対し拮抗活性を有するグルタミン酸誘導体およびアスパラギン酸誘導体およびその製造法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6144855A (fr) |
| IT (1) | IT1178982B (fr) |
| ZA (1) | ZA854660B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1984
- 1984-06-25 IT IT67644/84A patent/IT1178982B/it active
-
1985
- 1985-06-20 ZA ZA854660A patent/ZA854660B/xx unknown
- 1985-06-25 JP JP60140103A patent/JPS6144855A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8467644A0 (it) | 1984-06-25 |
| IT1178982B (it) | 1987-09-16 |
| IT8467644A1 (it) | 1985-12-25 |
| ZA854660B (en) | 1986-02-26 |
| JPS6144855A (ja) | 1986-03-04 |
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