NO973001L - Pyrimidin-derivater - Google Patents

Info

Publication number

NO973001L

NO973001L NO973001A NO973001A NO973001L NO 973001 L NO973001 L NO 973001L NO 973001 A NO973001 A NO 973001A NO 973001 A NO973001 A NO 973001A NO 973001 L NO973001 L NO 973001L

Authority

NO

Norway

Prior art keywords

compound

pyrimidinyl

methoxyphenoxy

pyrimidinyloxy

synthesis

Prior art date

1994-12-28

Links

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• 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 28
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
• 108050009340 Endothelin Proteins 0.000 claims abstract description 22
• 102000002045 Endothelin Human genes 0.000 claims abstract description 22
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 239000003814 drug Substances 0.000 claims abstract description 14
• 239000004480 active ingredient Substances 0.000 claims abstract description 5
• 238000000034 method Methods 0.000 claims description 135
• 239000000203 mixture Substances 0.000 claims description 39
• 229940079593 drug Drugs 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims 2
• 150000001875 compounds Chemical class 0.000 abstract description 303
• 125000000217 alkyl group Chemical group 0.000 abstract description 27
• 125000003710 aryl alkyl group Chemical group 0.000 abstract description 11
• 125000003118 aryl group Chemical group 0.000 abstract description 6
• 230000000694 effects Effects 0.000 abstract description 5
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 5
• 230000003639 vasoconstrictive effect Effects 0.000 abstract description 3
• 125000003545 alkoxy group Chemical group 0.000 abstract description 2
• 230000002401 inhibitory effect Effects 0.000 abstract description 2
• 230000004663 cell proliferation Effects 0.000 abstract 1
• 230000003389 potentiating effect Effects 0.000 abstract 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
• 230000015572 biosynthetic process Effects 0.000 description 124
• 238000003786 synthesis reaction Methods 0.000 description 124
• 238000005160 1H NMR spectroscopy Methods 0.000 description 112
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 94
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
• -1 methoxy, ethoxy, n-propoxy, isopropoxy Chemical group 0.000 description 80
• 239000003921 oil Substances 0.000 description 71
• 239000000843 powder Substances 0.000 description 60
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 230000002829 reductive effect Effects 0.000 description 29
• 239000000243 solution Substances 0.000 description 29
• 125000001424 substituent group Chemical group 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• 239000002904 solvent Substances 0.000 description 19
• 159000000000 sodium salts Chemical class 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 238000002844 melting Methods 0.000 description 16
• 230000008018 melting Effects 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
• 229940080818 propionamide Drugs 0.000 description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 13
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• 102000005962 receptors Human genes 0.000 description 11
• 108020003175 receptors Proteins 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 101150084411 crn1 gene Proteins 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• 239000000872 buffer Substances 0.000 description 7
• WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 7
• YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 230000008485 antagonism Effects 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 230000008602 contraction Effects 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 238000001035 drying Methods 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 239000012300 argon atmosphere Substances 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 210000000056 organ Anatomy 0.000 description 5
• 238000012746 preparative thin layer chromatography Methods 0.000 description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 4
• WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 4
• JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
• 206010020772 Hypertension Diseases 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 210000002376 aorta thoracic Anatomy 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
• MQYQOVYIJOLTNX-UHFFFAOYSA-N dichloromethane;n,n-dimethylformamide Chemical compound ClCCl.CN(C)C=O MQYQOVYIJOLTNX-UHFFFAOYSA-N 0.000 description 4
• 239000003480 eluent Substances 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 208000019423 liver disease Diseases 0.000 description 4
• 210000004379 membrane Anatomy 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
• RZBOMSOHMOVUES-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1Cl RZBOMSOHMOVUES-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• 230000003042 antagnostic effect Effects 0.000 description 3
• 239000012230 colorless oil Substances 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 125000005343 heterocyclic alkyl group Chemical group 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• DGNZGWDLQMQJRJ-UHFFFAOYSA-N n-[2-[4,6-bis(3-hydroxypropoxy)pyrimidin-2-yl]-6-(3-hydroxypropoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=C(OCCCO)C=C(OCCCO)N=2)OCCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 DGNZGWDLQMQJRJ-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
• VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 3
• 239000008188 pellet Substances 0.000 description 3
• 239000013014 purified material Substances 0.000 description 3
• CUYKNJBYIJFRCU-UHFFFAOYSA-N pyridine-3-amine Natural products NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• PALBHKATLKQZER-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl 3-phenylmethoxypropanoate Chemical compound C=1C=CC=CC=1COCCC(=O)OCC1(C)COC1 PALBHKATLKQZER-UHFFFAOYSA-N 0.000 description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
• WMEJFOASTQGIRO-UHFFFAOYSA-N 1-methyl-4-(2-phenylmethoxyethyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(C)(CO2)COC21CCOCC1=CC=CC=C1 WMEJFOASTQGIRO-UHFFFAOYSA-N 0.000 description 2
• RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
• UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
• AUSGHWJMOCPLII-UHFFFAOYSA-N 2-(1-methyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)ethanol Chemical compound C1OC2(CCO)OCC1(C)CO2 AUSGHWJMOCPLII-UHFFFAOYSA-N 0.000 description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
• MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
• PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
• OZGUGVRKYBSDBN-UHFFFAOYSA-N 3-phenylmethoxypropanoic acid Chemical compound OC(=O)CCOCC1=CC=CC=C1 OZGUGVRKYBSDBN-UHFFFAOYSA-N 0.000 description 2
• MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
• LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 2
• 208000009304 Acute Kidney Injury Diseases 0.000 description 2
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 206010002388 Angina unstable Diseases 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
• 208000020084 Bone disease Diseases 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• 206010007559 Cardiac failure congestive Diseases 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 208000018522 Gastrointestinal disease Diseases 0.000 description 2
• 206010019280 Heart failures Diseases 0.000 description 2
• 239000003810 Jones reagent Substances 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
• 208000033626 Renal failure acute Diseases 0.000 description 2
• 101710205037 Sarafotoxin Proteins 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 2
• 208000007814 Unstable Angina Diseases 0.000 description 2
• 208000012931 Urologic disease Diseases 0.000 description 2
• 206010047163 Vasospasm Diseases 0.000 description 2
• 150000008065 acid anhydrides Chemical class 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 201000011040 acute kidney failure Diseases 0.000 description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 206010003119 arrhythmia Diseases 0.000 description 2
• 230000006793 arrhythmia Effects 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• 208000006673 asthma Diseases 0.000 description 2
• 239000002585 base Substances 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
• 210000004204 blood vessel Anatomy 0.000 description 2
• 229940098773 bovine serum albumin Drugs 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
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• 208000020832 chronic kidney disease Diseases 0.000 description 2
• 208000022831 chronic renal failure syndrome Diseases 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 125000004093 cyano group Chemical group *C#N 0.000 description 2
• 125000006165 cyclic alkyl group Chemical group 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 206010012601 diabetes mellitus Diseases 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
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• 208000037765 diseases and disorders Diseases 0.000 description 2
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• 239000006185 dispersion Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
• 201000005577 familial hyperlipidemia Diseases 0.000 description 2
• 239000000194 fatty acid Substances 0.000 description 2
• 229930195729 fatty acid Natural products 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 210000001156 gastric mucosa Anatomy 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 208000019622 heart disease Diseases 0.000 description 2
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 201000004332 intermediate coronary syndrome Diseases 0.000 description 2
• 230000000302 ischemic effect Effects 0.000 description 2
• 208000017169 kidney disease Diseases 0.000 description 2
• 210000002752 melanocyte Anatomy 0.000 description 2
• 208000010125 myocardial infarction Diseases 0.000 description 2
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