NO311224B1 - Nye cykliske aminosyrederivater, farmasöytisk sammensetning som inneholder slike, samt fremgangsmåte for fremstilling av slike - Google Patents
Nye cykliske aminosyrederivater, farmasöytisk sammensetning som inneholder slike, samt fremgangsmåte for fremstilling av slike Download PDFInfo
- Publication number
- NO311224B1 NO311224B1 NO19944364A NO944364A NO311224B1 NO 311224 B1 NO311224 B1 NO 311224B1 NO 19944364 A NO19944364 A NO 19944364A NO 944364 A NO944364 A NO 944364A NO 311224 B1 NO311224 B1 NO 311224B1
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- compound
- formula
- hydrogen
- represents hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- -1 cyclic amino acid derivatives Chemical class 0.000 title claims description 117
- 230000008569 process Effects 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 67
- 239000001257 hydrogen Substances 0.000 claims abstract description 67
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 150000001721 carbon Chemical group 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 87
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 52
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 150000002431 hydrogen Chemical group 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 208000029422 Hypernatremia Diseases 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006383 alkylpyridyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract description 17
- 230000005764 inhibitory process Effects 0.000 abstract description 10
- 241000124008 Mammalia Species 0.000 abstract description 8
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000005841 biaryl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 150000002019 disulfides Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 241000700159 Rattus Species 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000012267 brine Substances 0.000 description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 102000003729 Neprilysin Human genes 0.000 description 9
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- 230000000694 effects Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 8
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- 239000011734 sodium Substances 0.000 description 8
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- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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- WMWOMMJQVXRFAP-UHFFFAOYSA-N 5-chloro-4,6-dimethoxytriazine Chemical compound COC1=NN=NC(OC)=C1Cl WMWOMMJQVXRFAP-UHFFFAOYSA-N 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 210000000231 kidney cortex Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000005291 magnetic effect Effects 0.000 description 1
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- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- VXYFARNRGZWHTJ-FVGYRXGTSA-N methyl (2s)-2-amino-3-(4-hydroxyphenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 VXYFARNRGZWHTJ-FVGYRXGTSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000002833 natriuretic agent Substances 0.000 description 1
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- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SLZHLQUFNFXTHB-UHFFFAOYSA-M sodium;5-butan-2-yl-5-ethyl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].CCC(C)C1(CC)C([O-])=NC(=S)NC1=O SLZHLQUFNFXTHB-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical class O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- 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
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/153,395 US5432186A (en) | 1993-11-16 | 1993-11-16 | Cyclic amino acid derivatives |
| US08/263,859 US5506244A (en) | 1993-11-16 | 1994-06-22 | Cyclic amino acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO944364D0 NO944364D0 (no) | 1994-11-15 |
| NO944364L NO944364L (no) | 1995-05-18 |
| NO311224B1 true NO311224B1 (no) | 2001-10-29 |
Family
ID=26850506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19944364A NO311224B1 (no) | 1993-11-16 | 1994-11-15 | Nye cykliske aminosyrederivater, farmasöytisk sammensetning som inneholder slike, samt fremgangsmåte for fremstilling av slike |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5668158A (zh) |
| EP (1) | EP0655461B1 (zh) |
| JP (1) | JP3647914B2 (zh) |
| CN (1) | CN1058019C (zh) |
| AT (1) | ATE193706T1 (zh) |
| AU (1) | AU687444B2 (zh) |
| CA (1) | CA2135711A1 (zh) |
| CY (1) | CY2234B1 (zh) |
| DE (1) | DE69424846T2 (zh) |
| DK (1) | DK0655461T3 (zh) |
| ES (1) | ES2148305T3 (zh) |
| FI (1) | FI118600B (zh) |
| GR (1) | GR3033829T3 (zh) |
| HU (1) | HU226300B1 (zh) |
| IL (1) | IL111581A (zh) |
| NO (1) | NO311224B1 (zh) |
| NZ (1) | NZ264913A (zh) |
| PH (1) | PH31056A (zh) |
| PT (1) | PT655461E (zh) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1273455B (it) * | 1995-01-27 | 1997-07-08 | Zambon Spa | Derivati tiolici ad attivita' inibitrice delle metallopeptidasi |
| JPH08325263A (ja) * | 1995-05-31 | 1996-12-10 | Sumitomo Metal Ind Ltd | 新規２−アミノ−３−フェニルプロピオン酸誘導体 |
| WO1997011717A1 (en) * | 1995-09-27 | 1997-04-03 | Novartis Ag | Treatment of chronic progressive renal failure |
| EP0894003A4 (en) * | 1996-04-12 | 2000-10-04 | Bristol Myers Squibb Co | N-FORMYL HYDROXYLAMINE-BASED COMPOUNDS SUITABLE AS INCEPTIENTS OF THE ACE ENZYME AND / OR ENDOPEPTIDASE NEP |
| US6777550B1 (en) | 1996-04-12 | 2004-08-17 | Bristol-Myers Squibb Company | N-formyl hydroxylamine containing compounds useful as ACE inhibitors and/or NEP inhibitors |
| US6423727B1 (en) | 1998-04-23 | 2002-07-23 | Novartis Ag | Certain thiol inhibitors of endothelin-converting enzyme |
| US6426354B1 (en) | 1998-04-23 | 2002-07-30 | Novartis Ag | Certain heteroaryl substituted thiol inhibitors of endothelin-converting enzyme |
| EP1073674A1 (en) * | 1998-04-23 | 2001-02-07 | Novartis AG | Thiol inhibitors of endothelin-converting enzyme |
| AU768880B2 (en) * | 1999-03-29 | 2004-01-08 | Bristol-Myers Squibb Company | Use of vasopeptidase inhibitors to treat angina pectoris |
| US6509330B2 (en) | 2000-02-17 | 2003-01-21 | Bristol-Myers Squibb Company | Hydroxamic acid containing compounds useful as ACE inhibitors and/or NEP inhibotors |
| DE60215368T2 (de) * | 2001-09-21 | 2007-08-16 | Novartis Ag | Pyranderivate als inhibitoren von ace und nep |
| US6919343B2 (en) | 2002-02-08 | 2005-07-19 | Merck & Co., Inc. | N-biphenyl(substituted methyl) aminocycloalkane-carboxamide derivatives |
| DE60303441T2 (de) | 2002-02-08 | 2006-09-21 | Merck & Co., Inc. | N-biphenylmethylaminocycloalkancarboxamid-derivative |
| US7045653B2 (en) | 2002-12-23 | 2006-05-16 | Pfizer, Inc. | Pharmaceuticals |
| EP2127658A4 (en) * | 2007-01-10 | 2011-04-27 | Kowa Co | THERAPEUTIC AGENT AGAINST MORBUS MENIERE |
| CN105670160A (zh) * | 2015-10-12 | 2016-06-15 | 陆思烨 | 一种防紫外抗老化电线电缆料及其制备方法 |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093739A (en) * | 1977-06-15 | 1978-06-06 | Mead Johnson & Company | Mercaptoacylamidobenzoyl glycine and mucolytic process |
| GB8820844D0 (en) * | 1988-09-05 | 1988-10-05 | Pfizer Ltd | Therapeutic agents |
| GB9004260D0 (en) * | 1990-02-26 | 1990-04-18 | Pfizer Ltd | Therapeutic agents |
| FR2679564A1 (fr) * | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
| US5208236A (en) * | 1992-09-23 | 1993-05-04 | Schering Corporation | N-(acylaminomethyl)glutaryl amino acids and use |
-
1994
- 1994-11-07 ES ES94810642T patent/ES2148305T3/es not_active Expired - Lifetime
- 1994-11-07 AT AT94810642T patent/ATE193706T1/de not_active IP Right Cessation
- 1994-11-07 DK DK94810642T patent/DK0655461T3/da active
- 1994-11-07 EP EP94810642A patent/EP0655461B1/en not_active Expired - Lifetime
- 1994-11-07 DE DE69424846T patent/DE69424846T2/de not_active Expired - Fee Related
- 1994-11-07 PT PT94810642T patent/PT655461E/pt unknown
- 1994-11-09 AU AU77729/94A patent/AU687444B2/en not_active Ceased
- 1994-11-10 IL IL11158194A patent/IL111581A/xx not_active IP Right Cessation
- 1994-11-11 PH PH49353A patent/PH31056A/en unknown
- 1994-11-14 FI FI945354A patent/FI118600B/fi not_active IP Right Cessation
- 1994-11-14 NZ NZ264913A patent/NZ264913A/en not_active IP Right Cessation
- 1994-11-14 CA CA002135711A patent/CA2135711A1/en not_active Abandoned
- 1994-11-15 CN CN94118911A patent/CN1058019C/zh not_active Expired - Fee Related
- 1994-11-15 NO NO19944364A patent/NO311224B1/no unknown
- 1994-11-15 JP JP28078594A patent/JP3647914B2/ja not_active Expired - Fee Related
- 1994-11-15 HU HU9403276A patent/HU226300B1/hu not_active IP Right Cessation
-
1996
- 1996-02-14 US US08/601,626 patent/US5668158A/en not_active Expired - Fee Related
-
2000
- 2000-06-30 GR GR20000401530T patent/GR3033829T3/el not_active IP Right Cessation
-
2001
- 2001-09-07 CY CY0100025A patent/CY2234B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK0655461T3 (da) | 2000-10-02 |
| AU687444B2 (en) | 1998-02-26 |
| NO944364L (no) | 1995-05-18 |
| NO944364D0 (no) | 1994-11-15 |
| ES2148305T3 (es) | 2000-10-16 |
| CN1107857A (zh) | 1995-09-06 |
| PH31056A (en) | 1998-02-03 |
| HU226300B1 (en) | 2008-08-28 |
| ATE193706T1 (de) | 2000-06-15 |
| NZ264913A (en) | 1997-02-24 |
| IL111581A (en) | 1999-07-14 |
| FI945354A (fi) | 1995-05-17 |
| FI945354A0 (fi) | 1994-11-14 |
| EP0655461B1 (en) | 2000-06-07 |
| CN1058019C (zh) | 2000-11-01 |
| JPH07196685A (ja) | 1995-08-01 |
| CY2234B1 (en) | 2003-04-18 |
| IL111581A0 (en) | 1995-01-24 |
| HUT71423A (en) | 1995-11-28 |
| AU7772994A (en) | 1995-05-25 |
| DE69424846T2 (de) | 2000-11-16 |
| FI118600B (fi) | 2008-01-15 |
| HU9403276D0 (en) | 1995-01-30 |
| EP0655461A1 (en) | 1995-05-31 |
| GR3033829T3 (en) | 2000-10-31 |
| US5668158A (en) | 1997-09-16 |
| DE69424846D1 (de) | 2000-07-13 |
| PT655461E (pt) | 2000-11-30 |
| CA2135711A1 (en) | 1995-05-17 |
| JP3647914B2 (ja) | 2005-05-18 |
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