DD247214A5 - Verfahren zur herstellung von amino-propanol-derivaten - Google Patents

Info

Publication number

DD247214A5

DD247214A5 DD86288793A DD28879386A DD247214A5 DD 247214 A5 DD247214 A5 DD 247214A5 DD 86288793 A DD86288793 A DD 86288793A DD 28879386 A DD28879386 A DD 28879386A DD 247214 A5 DD247214 A5 DD 247214A5

Authority

DD

German Democratic Republic

Prior art keywords

propanol

group

nitroxy

ethylamino

dimethyl

Prior art date

1985-04-06

Links

• Espacenet
• Global Dossier
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• MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 title 1
• -1 legs straight-chain Chemical group 0.000 claims abstract description 545
• 150000001875 compounds Chemical class 0.000 claims abstract description 91
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 67
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 10
• 239000001257 hydrogen Substances 0.000 claims abstract description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• 150000003839 salts Chemical class 0.000 claims abstract description 10
• 238000000034 method Methods 0.000 claims abstract description 9
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000003118 aryl group Chemical group 0.000 claims abstract description 4
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 4
• 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
• 150000001412 amines Chemical class 0.000 claims description 29
• 238000006243 chemical reaction Methods 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims description 8
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 238000003786 synthesis reaction Methods 0.000 claims description 3
• 229910052721 tungsten Inorganic materials 0.000 claims description 3
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 239000002243 precursor Substances 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
• 125000000623 heterocyclic group Chemical group 0.000 claims 1
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
• IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims 1
• 238000011282 treatment Methods 0.000 abstract description 4
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 3
• 230000000144 pharmacologic effect Effects 0.000 abstract description 3
• 239000003814 drug Substances 0.000 abstract description 2
• 238000011321 prophylaxis Methods 0.000 abstract description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 143
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• 229960004592 isopropanol Drugs 0.000 description 109
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 103
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 238000002844 melting Methods 0.000 description 51
• 230000008018 melting Effects 0.000 description 51
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 48
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
• 239000002904 solvent Substances 0.000 description 37
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 29
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 25
• 239000000243 solution Substances 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 24
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 21
• FBBJXJRFGXZOIQ-UHFFFAOYSA-N [4-(2-aminoethylamino)-4-oxobutyl] nitrate Chemical compound NCCNC(=O)CCCO[N+]([O-])=O FBBJXJRFGXZOIQ-UHFFFAOYSA-N 0.000 description 21
• 229910017604 nitric acid Inorganic materials 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 15
• 239000001294 propane Substances 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 239000003960 organic solvent Substances 0.000 description 10
• SRBNNNAAAKQFMB-UHFFFAOYSA-N (3-chloro-2,2-dimethyl-3-oxopropyl) nitrate Chemical compound ClC(=O)C(C)(C)CO[N+]([O-])=O SRBNNNAAAKQFMB-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• CYWBKVPYXOCIOB-UHFFFAOYSA-N [4-[(2-amino-2-methylpropyl)amino]-4-oxobutyl] nitrate Chemical compound CC(C)(N)CNC(=O)CCCO[N+]([O-])=O CYWBKVPYXOCIOB-UHFFFAOYSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 9
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• JUDPWYRXEJAGOF-UHFFFAOYSA-N [5-(2-aminoethylamino)-5-oxopentyl] nitrate Chemical compound NCCNC(=O)CCCCO[N+]([O-])=O JUDPWYRXEJAGOF-UHFFFAOYSA-N 0.000 description 8
• 229940109275 cyclamate Drugs 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 7
• 239000000203 mixture Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 description 6
• DAGBZRAFMXTXNY-UHFFFAOYSA-N 2-[(2-chloro-5-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=C(Cl)C(OCC2OC2)=C1 DAGBZRAFMXTXNY-UHFFFAOYSA-N 0.000 description 6
• XENMLDGAMXHYMH-UHFFFAOYSA-N 2-[(2-prop-2-enylphenoxy)methyl]oxirane Chemical compound C=CCC1=CC=CC=C1OCC1OC1 XENMLDGAMXHYMH-UHFFFAOYSA-N 0.000 description 6
• QPBYYTKPYJRYKF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1,3-dihydroindol-2-one Chemical compound N1C(=O)CC2=C1C=CC=C2OCC1CO1 QPBYYTKPYJRYKF-UHFFFAOYSA-N 0.000 description 6
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 229910002651 NO3 Inorganic materials 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 description 5
• CTWQPSSVUYPWOM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CO1 CTWQPSSVUYPWOM-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
• WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
• 125000005978 1-naphthyloxy group Chemical group 0.000 description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
• XKHLKNJSCIDVGW-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole-3-carbonitrile Chemical compound C=12C(C#N)=CNC2=CC=CC=1OCC1CO1 XKHLKNJSCIDVGW-UHFFFAOYSA-N 0.000 description 4
• VQTWQOBNPISQPG-UHFFFAOYSA-N 5-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC1CO1 VQTWQOBNPISQPG-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
• XSSKJRJNYWESJU-NXEZZACHSA-N O([N+](=O)[O-])[C@H]1[C@@H](CCCC1)N(CCN)C(C)=O Chemical compound O([N+](=O)[O-])[C@H]1[C@@H](CCCC1)N(CCN)C(C)=O XSSKJRJNYWESJU-NXEZZACHSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• FIYKWBHWUURYBU-UHFFFAOYSA-N [4-(2-aminoethylamino)-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCCN FIYKWBHWUURYBU-UHFFFAOYSA-N 0.000 description 4
• HJLFKTSVWNYKFO-UHFFFAOYSA-N [4-[(2-amino-2-methylpropyl)amino]-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCC(C)(C)N HJLFKTSVWNYKFO-UHFFFAOYSA-N 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000001530 fumaric acid Substances 0.000 description 4
• 229960002479 isosorbide Drugs 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 3
• 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 3
• UEOWFGJMGUIGHC-UHFFFAOYSA-N 2-[[4-(2-methoxyethyl)phenoxy]methyl]oxirane Chemical compound C1=CC(CCOC)=CC=C1OCC1OC1 UEOWFGJMGUIGHC-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• UCQAPROAHYVQIS-UHFFFAOYSA-N butanoic acid;propan-1-ol Chemical compound CCCO.CCCC(O)=O UCQAPROAHYVQIS-UHFFFAOYSA-N 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000012074 organic phase Substances 0.000 description 3
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
• 125000006308 propyl amino group Chemical group 0.000 description 3
• 239000000376 reactant Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• GRDPPSMNRDZCGL-TYYBGVCCSA-N (e)-but-2-enedioic acid;propan-2-ol Chemical compound CC(C)O.OC(=O)\C=C\C(O)=O GRDPPSMNRDZCGL-TYYBGVCCSA-N 0.000 description 2
• 125000005657 1,3-cyclobutylene group Chemical group [H]C1([H])C([H])([*:1])C([H])([H])C1([H])[*:2] 0.000 description 2
• 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 2
• RBAJCZCYJOCDCQ-UHFFFAOYSA-N 1-[(1-amino-2-methylpropan-2-yl)amino]-3-(3-methylbenzimidazol-4-yl)oxypropan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)CN)=C2N(C)C=NC2=C1 RBAJCZCYJOCDCQ-UHFFFAOYSA-N 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
• AWACIWVAABNWPO-UHFFFAOYSA-N 1-methyl-7-(oxiran-2-ylmethoxy)benzimidazole Chemical compound C=12N(C)C=NC2=CC=CC=1OCC1CO1 AWACIWVAABNWPO-UHFFFAOYSA-N 0.000 description 2
• UZKATEAEAWUUBH-UHFFFAOYSA-N 1-n,1-n-dibenzyl-2-methylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CC(C)(N)C)CC1=CC=CC=C1 UZKATEAEAWUUBH-UHFFFAOYSA-N 0.000 description 2
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
• BKYYOPSMOZNITO-UHFFFAOYSA-N 2-[(2,5-dichlorophenoxy)methyl]oxirane Chemical compound ClC1=CC=C(Cl)C(OCC2OC2)=C1 BKYYOPSMOZNITO-UHFFFAOYSA-N 0.000 description 2
• FZONULHLKBOHHY-UHFFFAOYSA-N 2-[(2-prop-2-enoxyphenoxy)methyl]oxirane Chemical compound C=CCOC1=CC=CC=C1OCC1OC1 FZONULHLKBOHHY-UHFFFAOYSA-N 0.000 description 2
• GWRBPJXLXXKTEL-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1OCC1CO1 GWRBPJXLXXKTEL-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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• BYPGXZNTYVFFPE-LYNLNPNLSA-N [(1R,2S)-2-[2-[2-[[3-[(3-cyano-6-methyl-1H-indol-4-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound C(#N)C1=CNC2=CC(=CC(=C12)OCC(CNCCNC(C[C@H]1[C@@H](CCCC1)O[N+](=O)[O-])=O)O)C BYPGXZNTYVFFPE-LYNLNPNLSA-N 0.000 description 1
• PWBIIZFOORPXIB-YKBQRGLWSA-N [(1R,2S)-2-[2-[[2-[[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]-2-methylpropyl]amino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound CC(CNC(C[C@H]1[C@@H](CCCC1)O[N+](=O)[O-])=O)(C)NCC(COC1=C2C=CNC2=CC=C1)O PWBIIZFOORPXIB-YKBQRGLWSA-N 0.000 description 1
• IQSOINXSLUMRTO-LVLJQFTKSA-N [(1R,2S)-2-[2-[[2-[[2-hydroxy-3-(3-methylbenzimidazol-4-yl)oxypropyl]amino]-2-methylpropyl]amino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound CN1C=NC2=C1C(=CC=C2)OCC(CNC(CNC(C[C@H]1[C@@H](CCCC1)O[N+](=O)[O-])=O)(C)C)O IQSOINXSLUMRTO-LVLJQFTKSA-N 0.000 description 1
• AJQRUGZKEYJURQ-LJJQOFDWSA-N [(1R,2S)-2-[2-[[2-[[2-hydroxy-3-[2-[2-(methylamino)-2-oxoethoxy]phenoxy]propyl]amino]-2-methylpropyl]amino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound CC(CNC(C[C@H]1[C@@H](CCCC1)O[N+](=O)[O-])=O)(C)NCC(COC1=C(C=CC=C1)OCC(=O)NC)O AJQRUGZKEYJURQ-LJJQOFDWSA-N 0.000 description 1
• BHDLGDROBHSOEI-PWKISDLSSA-N [(1R,2S)-2-[2-[[2-[[2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-2-methylpropyl]amino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound COCCC1=CC=C(OCC(CNC(CNC(C[C@H]2[C@@H](CCCC2)O[N+](=O)[O-])=O)(C)C)O)C=C1 BHDLGDROBHSOEI-PWKISDLSSA-N 0.000 description 1
• OHNKRBGTTLXERA-GVVCSIHDSA-N [(1R,2S)-2-[2-[[2-[[3-(2,5-dichlorophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-2-oxoethyl]cyclohexyl] nitrate Chemical compound ClC1=C(OCC(CNC(CNC(C[C@H]2[C@@H](CCCC2)O[N+](=O)[O-])=O)(C)C)O)C=C(C=C1)Cl OHNKRBGTTLXERA-GVVCSIHDSA-N 0.000 description 1
• SYTQNRPKISNNFN-YUZWYKEKSA-N [(1r,2r)-2-[2-[2-[[2-hydroxy-3-(1h-indol-4-yloxy)propyl]amino]ethylamino]-2-oxoethyl]sulfanylcyclohexyl] nitrate Chemical compound C=1C=CC=2NC=CC=2C=1OCC(O)CNCCNC(=O)CS[C@@H]1CCCC[C@H]1O[N+]([O-])=O SYTQNRPKISNNFN-YUZWYKEKSA-N 0.000 description 1
• MMNYOUBFLAMZQS-UHFFFAOYSA-N [1-[[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]carbamoyl]piperidin-4-yl]methyl nitrate Chemical compound C=1C=CC=C(C#N)C=1OCC(O)CNC(C)(C)CNC(=O)N1CCC(CO[N+]([O-])=O)CC1 MMNYOUBFLAMZQS-UHFFFAOYSA-N 0.000 description 1
• WRONVHKRESQZQC-UHFFFAOYSA-N [2,3,6-trimethyl-4-(oxiran-2-ylmethoxy)phenyl] acetate Chemical compound CC1=C(C)C(OC(=O)C)=C(C)C=C1OCC1OC1 WRONVHKRESQZQC-UHFFFAOYSA-N 0.000 description 1
• FKGAFAQNUPOVCZ-UHFFFAOYSA-N [3-(2-aminoethylamino)-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound [O-][N+](=O)OCC(C)(C)C(=O)NCCN FKGAFAQNUPOVCZ-UHFFFAOYSA-N 0.000 description 1
• JNOMPHFDBHJPAG-UHFFFAOYSA-N [3-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethylamino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound CC(C(=O)NCCNCC(COC1=CC=CC2=CC=CC=C12)O)(CO[N+](=O)[O-])C JNOMPHFDBHJPAG-UHFFFAOYSA-N 0.000 description 1
• YBLTXFFPOAJMEX-UHFFFAOYSA-N [3-[2-[[2-hydroxy-3-[(2-oxo-1,3-dihydroindol-4-yl)oxy]propyl]amino]ethylamino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound CC(C(=O)NCCNCC(COC1=C2CC(NC2=CC=C1)=O)O)(CO[N+](=O)[O-])C YBLTXFFPOAJMEX-UHFFFAOYSA-N 0.000 description 1
• WATZRZKRXNBEPI-UHFFFAOYSA-N [3-[2-[[3-[2-acetyl-4-(butanoylamino)phenoxy]-2-hydroxypropyl]amino]ethylamino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNCCNC(=O)C(C)(C)CO[N+]([O-])=O)C(C(C)=O)=C1 WATZRZKRXNBEPI-UHFFFAOYSA-N 0.000 description 1
• WAMYPCHWOSYZKU-UHFFFAOYSA-N [3-[[2-[[2-hydroxy-3-[(2-oxo-1,3-dihydroindol-4-yl)oxy]propyl]amino]-2-methylpropyl]amino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound [O-][N+](=O)OCC(C)(C)C(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1CC(=O)N2 WAMYPCHWOSYZKU-UHFFFAOYSA-N 0.000 description 1
• KCLIPJPMVWTGRT-UHFFFAOYSA-N [3-[[2-[[3-[2-acetyl-4-(butanoylamino)phenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-2,2-dimethyl-3-oxopropyl] nitrate Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)(C)CNC(=O)C(C)(C)CO[N+]([O-])=O)C(C(C)=O)=C1 KCLIPJPMVWTGRT-UHFFFAOYSA-N 0.000 description 1
• CBMQMHRVHTVYSN-UHFFFAOYSA-N [3-chloro-2-methyl-2-(nitrooxymethyl)-3-oxopropyl] nitrate Chemical compound [O-][N+](=O)OCC(C)(CO[N+]([O-])=O)C(Cl)=O CBMQMHRVHTVYSN-UHFFFAOYSA-N 0.000 description 1
• NKFUVXUDYWVRLV-UHFFFAOYSA-N [4-(2-aminoethylamino)-3-methyl-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCC(C)C(=O)NCCN NKFUVXUDYWVRLV-UHFFFAOYSA-N 0.000 description 1
• JRJCSKWVMONKEJ-UHFFFAOYSA-N [4-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethylamino]-4-oxobutan-2-yl] nitrate Chemical compound C1=CC=C2C(OCC(O)CNCCNC(=O)CC(C)O[N+]([O-])=O)=CC=CC2=C1 JRJCSKWVMONKEJ-UHFFFAOYSA-N 0.000 description 1
• JXKMFJCFJIFODL-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]ethylamino]-4-oxobutan-2-yl] nitrate Chemical compound N1C=CC2=C(C=CC=C12)OCC(CNCCNC(CC(C)O[N+](=O)[O-])=O)O JXKMFJCFJIFODL-UHFFFAOYSA-N 0.000 description 1
• KSDQXYWFEFUADM-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-(3-methylbenzimidazol-4-yl)oxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound CN1C=NC2=C1C(=CC=C2)OCC(CNCCNC(CCCO[N+](=O)[O-])=O)O KSDQXYWFEFUADM-UHFFFAOYSA-N 0.000 description 1
• GKVYBOODKYCBKQ-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]amino]ethylamino]-3-methyl-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCC(C)C(=O)NCCNCC(O)COC1=CC(C)=C(O)C(C)=C1C GKVYBOODKYCBKQ-UHFFFAOYSA-N 0.000 description 1
• KNPSLJDSBNICJD-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound CC1=CC(OCC(O)CNCCNC(=O)CCCO[N+]([O-])=O)=C(C)C(C)=C1O KNPSLJDSBNICJD-UHFFFAOYSA-N 0.000 description 1
• IXINDIHLLCCDIO-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-[(2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]propyl]amino]ethylamino]-3-methyl-4-oxobutyl] nitrate Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNCCNC(=O)C(CCO[N+]([O-])=O)C IXINDIHLLCCDIO-UHFFFAOYSA-N 0.000 description 1
• SLUQPGKSQGNGCZ-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-[(3-oxo-1,2-dihydroinden-4-yl)oxy]propyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound O([N+](=O)[O-])CCCC(=O)NCCNCC(COC=1C=CC=C2CCC(C=12)=O)O SLUQPGKSQGNGCZ-UHFFFAOYSA-N 0.000 description 1
• KKJJJCBPAXTQOG-UHFFFAOYSA-N [4-[2-[[2-hydroxy-3-[[2-(hydroxymethyl)-1h-indol-4-yl]oxy]propyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound C1=CC=C2NC(CO)=CC2=C1OCC(O)CNCCNC(=O)CCCO[N+]([O-])=O KKJJJCBPAXTQOG-UHFFFAOYSA-N 0.000 description 1
• SVLANKCZBJWRCC-UHFFFAOYSA-N [4-[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]ethylamino]-4-oxobutan-2-yl] nitrate Chemical compound C(#N)C1=C(OCC(CNCCNC(CC(C)O[N+](=O)[O-])=O)O)C=CC=C1 SVLANKCZBJWRCC-UHFFFAOYSA-N 0.000 description 1
• RUTVCJVEAVOBGE-UHFFFAOYSA-N [4-[2-[[3-[(2,2-dioxo-3,4-dihydro-1,2$l^{6}-benzoxathiin-5-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound O1S(=O)(=O)CCC2=C1C=CC=C2OCC(CNCCNC(=O)CCCO[N+]([O-])=O)O RUTVCJVEAVOBGE-UHFFFAOYSA-N 0.000 description 1
• XVDBWMQGVCGUKG-UHFFFAOYSA-N [4-[2-[[3-[(3-cyano-2-oxo-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound N1C(=O)C(C#N)=CC2=C1C=CC=C2OCC(CNCCNC(=O)CCCO[N+]([O-])=O)O XVDBWMQGVCGUKG-UHFFFAOYSA-N 0.000 description 1
• KPKCBYJQCUAGRL-UHFFFAOYSA-N [4-[2-[[3-[(3-cyano-2h-chromen-8-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutan-2-yl] nitrate Chemical compound C1=C(C#N)COC2=C1C=CC=C2OCC(O)CNCCNC(=O)CC(C)O[N+]([O-])=O KPKCBYJQCUAGRL-UHFFFAOYSA-N 0.000 description 1
• ITQXDYVXSXMIRA-UHFFFAOYSA-N [4-[2-[[3-[(3-cyano-2h-chromen-8-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound C1=C(C#N)COC2=C1C=CC=C2OCC(CNCCNC(=O)CCCO[N+]([O-])=O)O ITQXDYVXSXMIRA-UHFFFAOYSA-N 0.000 description 1
• ZOVQTLVUMURPFY-UHFFFAOYSA-N [4-[2-[[3-[(3-cyano-7-methyl-2-oxo-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound C1=C(C#N)C(=O)NC2=CC(C)=CC(OCC(O)CNCCNC(=O)CCCO[N+]([O-])=O)=C21 ZOVQTLVUMURPFY-UHFFFAOYSA-N 0.000 description 1
• RWTLZPUBRKQACP-UHFFFAOYSA-N [4-[2-[[3-[2-acetyl-4-(butanoylamino)phenoxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound C(CCC)(=O)NC1=CC(=C(OCC(CNCCNC(CCCO[N+](=O)[O-])=O)O)C=C1)C(=O)C RWTLZPUBRKQACP-UHFFFAOYSA-N 0.000 description 1
• NUXAGGWNRRKTTQ-UHFFFAOYSA-N [4-[2-[[3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound NC(=O)CC1=CC=C(OCC(O)CNCCNC(=O)CCCO[N+]([O-])=O)C=C1 NUXAGGWNRRKTTQ-UHFFFAOYSA-N 0.000 description 1
• ACOQFJSAFJIGSA-UHFFFAOYSA-N [4-[2-[[3-[4-(butanoylamino)-2-cyanophenoxy]-2-hydroxypropyl]amino]ethylamino]-4-oxobutyl] nitrate Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNCCNC(=O)CCCO[N+]([O-])=O)C(C#N)=C1 ACOQFJSAFJIGSA-UHFFFAOYSA-N 0.000 description 1
• ATNOTPINCWQMCU-UHFFFAOYSA-N [4-[2-hydroxy-3-[2-(5-nitrooxypentanoylamino)ethylamino]propoxy]-2,3,6-trimethylphenyl] acetate Chemical compound CC(=O)OC1=C(C)C=C(OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O)C(C)=C1C ATNOTPINCWQMCU-UHFFFAOYSA-N 0.000 description 1
• FPKDZWLLIFXKNJ-UHFFFAOYSA-N [4-[2-hydroxy-3-[2-[[2-(2-nitrooxyethoxy)acetyl]amino]ethylamino]propoxy]-2,3,6-trimethylphenyl] acetate Chemical compound CC(=O)OC1=C(C)C=C(OCC(O)CNCCNC(=O)COCCO[N+]([O-])=O)C(C)=C1C FPKDZWLLIFXKNJ-UHFFFAOYSA-N 0.000 description 1
• YUTVTHWJMXAPSM-UHFFFAOYSA-N [4-[2-hydroxy-3-[2-[[2-(2-nitrooxyethylsulfanyl)acetyl]amino]ethylamino]propoxy]-2,3,6-trimethylphenyl] acetate Chemical compound CC(=O)OC1=C(C(=C(OCC(CNCCNC(CSCCO[N+](=O)[O-])=O)O)C=C1C)C)C YUTVTHWJMXAPSM-UHFFFAOYSA-N 0.000 description 1
• BWSCBURCYXTQAS-UHFFFAOYSA-N [4-[2-hydroxy-3-[[2-methyl-1-[[4-(1-nitrooxyethyl)piperidine-1-carbonyl]amino]propan-2-yl]amino]propoxy]-2,3,6-trimethylphenyl] acetate Chemical compound C1CC(C(O[N+]([O-])=O)C)CCN1C(=O)NCC(C)(C)NCC(O)COC1=CC(C)=C(OC(C)=O)C(C)=C1C BWSCBURCYXTQAS-UHFFFAOYSA-N 0.000 description 1
• RNTAWNUUQNNOJW-UHFFFAOYSA-N [4-[3-[(1-amino-2-methylpropan-2-yl)amino]-2-hydroxypropoxy]-2,3,6-trimethylphenyl] acetate Chemical compound CC(=O)OC1=C(C)C=C(OCC(O)CNC(C)(C)CN)C(C)=C1C RNTAWNUUQNNOJW-UHFFFAOYSA-N 0.000 description 1
• DDDOYSYVBXOFMW-UHFFFAOYSA-N [4-[3-[[3-[(3-cyano-1H-indol-4-yl)oxy]-2-hydroxypropyl]amino]propylamino]-4-oxobutyl] nitrate Chemical compound C(#N)C1=CNC2=CC=CC(=C12)OCC(CNCCCNC(CCCO[N+](=O)[O-])=O)O DDDOYSYVBXOFMW-UHFFFAOYSA-N 0.000 description 1
• OOBKLQXVRMVHJK-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CC(CNC(CCCO[N+](=O)[O-])=O)(C)NCC(COC1=C2C=CNC2=CC=C1)O OOBKLQXVRMVHJK-UHFFFAOYSA-N 0.000 description 1
• POLKZKFKBLLTCK-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound COC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CC(C)O[N+]([O-])=O POLKZKFKBLLTCK-UHFFFAOYSA-N 0.000 description 1
• YSOSESTZNPNFEB-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O YSOSESTZNPNFEB-UHFFFAOYSA-N 0.000 description 1
• VQBZLNGDKZUDDY-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(2-methylsulfanylphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CSC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O VQBZLNGDKZUDDY-UHFFFAOYSA-N 0.000 description 1
• ZTMQGPPXUAJUJX-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(2-prop-2-ynoxyphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC=C1OCC#C ZTMQGPPXUAJUJX-UHFFFAOYSA-N 0.000 description 1
• BHDQKBGRDCYVKE-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(3-methylphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CC1=CC=CC(OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O)=C1 BHDQKBGRDCYVKE-UHFFFAOYSA-N 0.000 description 1
• WWZWUGMWOLGXHZ-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCC(C)(C)NCC(O)COC1=CC(C)=C(O)C(C)=C1C WWZWUGMWOLGXHZ-UHFFFAOYSA-N 0.000 description 1
• OUWJFIRGRGJTBX-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[(2-methyl-1h-indol-4-yl)oxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O OUWJFIRGRGJTBX-UHFFFAOYSA-N 0.000 description 1
• ZOECWYDWIYLGOG-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[(2-oxo-1h-quinazolin-5-yl)oxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound N1C(=O)N=CC2=C1C=CC=C2OCC(O)CNC(C)(CNC(=O)CCCO[N+]([O-])=O)C ZOECWYDWIYLGOG-UHFFFAOYSA-N 0.000 description 1
• LJALVAQAAZQHHU-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[(2-oxo-1h-quinolin-5-yl)oxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound N1C(=O)C=CC2=C1C=CC=C2OCC(O)CNC(C)(C)CNC(=O)CC(C)O[N+]([O-])=O LJALVAQAAZQHHU-UHFFFAOYSA-N 0.000 description 1
• SHRQCLIPRKWESW-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[(3-oxo-1,2-dihydroinden-4-yl)oxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1C(=O)CC2 SHRQCLIPRKWESW-UHFFFAOYSA-N 0.000 description 1
• MSSVVPPTTDKKGP-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[(3-oxo-1,2-dihydroinden-4-yl)oxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1C(=O)CC2 MSSVVPPTTDKKGP-UHFFFAOYSA-N 0.000 description 1
• LLMYISWOSHMVEI-UHFFFAOYSA-N [4-[[2-[[2-hydroxy-3-[2-[2-(methylamino)-2-oxoethoxy]phenoxy]propyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CNC(=O)COC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O LLMYISWOSHMVEI-UHFFFAOYSA-N 0.000 description 1
• GVLPPCTWLYIVOM-UHFFFAOYSA-N [4-[[2-[[3-(1,3-benzothiazol-7-yloxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1SC=N2 GVLPPCTWLYIVOM-UHFFFAOYSA-N 0.000 description 1
• GWDWQBOTTZQIBF-UHFFFAOYSA-N [4-[[2-[[3-(2,5-dichlorophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound [O-][N+](=O)OCCCC(=O)NCC(C)(C)NCC(O)COC1=CC(Cl)=CC=C1Cl GWDWQBOTTZQIBF-UHFFFAOYSA-N 0.000 description 1
• LUFHCUKKERDLNG-UHFFFAOYSA-N [4-[[2-[[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCC(C)(C)NCC(O)COC1=CC(C)=CC=C1Cl LUFHCUKKERDLNG-UHFFFAOYSA-N 0.000 description 1
• SBMBCLVCBGDUTJ-UHFFFAOYSA-N [4-[[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CC(=O)NCC(C)(C)NCC(O)COC1=CC=CC=C1C#N SBMBCLVCBGDUTJ-UHFFFAOYSA-N 0.000 description 1
• SAQQLDFSWZIAQH-UHFFFAOYSA-N [4-[[2-[[3-(3,4-dihydro-2H-thiochromen-8-yloxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1CCSC2=C1C=CC=C2OCC(O)CNC(C)(CNC(=O)CCCO[N+]([O-])=O)C SAQQLDFSWZIAQH-UHFFFAOYSA-N 0.000 description 1
• DMAZSBSXCPARQY-UHFFFAOYSA-N [4-[[2-[[3-[(2-formyl-3,4-dihydro-1h-isoquinolin-5-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1N(C=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(CNC(=O)CCCO[N+]([O-])=O)C DMAZSBSXCPARQY-UHFFFAOYSA-N 0.000 description 1
• YQIQDSDDZACDNO-UHFFFAOYSA-N [4-[[2-[[3-[(3-cyano-2h-chromen-8-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutan-2-yl] nitrate Chemical compound C1=C(C#N)COC2=C1C=CC=C2OCC(O)CNC(C)(C)CNC(=O)CC(C)O[N+]([O-])=O YQIQDSDDZACDNO-UHFFFAOYSA-N 0.000 description 1
• FHRPYHZRERGCSJ-UHFFFAOYSA-N [4-[[2-[[3-[(3-cyano-2h-chromen-8-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1=C(C#N)COC2=C1C=CC=C2OCC(O)CNC(C)(CNC(=O)CCCO[N+]([O-])=O)C FHRPYHZRERGCSJ-UHFFFAOYSA-N 0.000 description 1
• ACVOZEAYYAKNSX-UHFFFAOYSA-N [4-[[2-[[3-[(3-cyano-7-methyl-2-oxo-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1=C(C#N)C(=O)NC2=CC(C)=CC(OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O)=C21 ACVOZEAYYAKNSX-UHFFFAOYSA-N 0.000 description 1
• MNWINCXROVFXGF-UHFFFAOYSA-N [4-[[2-[[3-[(8-acetamido-2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound C1CC(=O)NC2=C1C(OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O)=CC=C2NC(=O)C MNWINCXROVFXGF-UHFFFAOYSA-N 0.000 description 1
• GGQSMUKOKNABEV-UHFFFAOYSA-N [4-[[2-[[3-[4-(butanoylamino)-2-cyanophenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-4-oxobutyl] nitrate Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)(C)CNC(=O)CCCO[N+]([O-])=O)C(C#N)=C1 GGQSMUKOKNABEV-UHFFFAOYSA-N 0.000 description 1
• DZMSYGYJWSJXQS-UHFFFAOYSA-N [4-[[3-[[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amino]-3-methylbutyl]amino]-4-oxobutyl] nitrate Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)CCNC(=O)CCCO[N+]([O-])=O)=C1 DZMSYGYJWSJXQS-UHFFFAOYSA-N 0.000 description 1
• HQSUFAXZRKNMTN-UHFFFAOYSA-N [5-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethylamino]-5-oxopentan-2-yl] nitrate Chemical compound C1=CC=C2C(OCC(O)CNCCNC(=O)CCC(C)O[N+]([O-])=O)=CC=CC2=C1 HQSUFAXZRKNMTN-UHFFFAOYSA-N 0.000 description 1
• UTIIAOUMDJHESQ-UHFFFAOYSA-N [5-[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]ethylamino]-5-oxopentyl] nitrate Chemical compound C1(=CC=CC2=CC=CC=C12)OCC(CNCCNC(CCCCO[N+](=O)[O-])=O)O UTIIAOUMDJHESQ-UHFFFAOYSA-N 0.000 description 1
• JBMLKWBZNHRULB-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound N1C=CC2=C(C=CC=C12)OCC(CNCCNC(CCCCO[N+](=O)[O-])=O)O JBMLKWBZNHRULB-UHFFFAOYSA-N 0.000 description 1
• KHQBWJMENBZTTI-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[(2-oxo-1,3-dihydroindol-4-yl)oxy]propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCCNCC(O)COC1=CC=CC2=C1CC(=O)N2 KHQBWJMENBZTTI-UHFFFAOYSA-N 0.000 description 1
• XJKKRRYUJAOUMR-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[(2-oxo-1h-quinolin-5-yl)oxy]propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound N1C(=O)C=CC2=C1C=CC=C2OCC(CNCCNC(=O)CCCCO[N+]([O-])=O)O XJKKRRYUJAOUMR-UHFFFAOYSA-N 0.000 description 1
• NDSDZJBUAUIKDU-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[(6-methyl-1H-indol-4-yl)oxy]propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound CC1=CC(=C2C=CNC2=C1)OCC(CNCCNC(CCCCO[N+](=O)[O-])=O)O NDSDZJBUAUIKDU-UHFFFAOYSA-N 0.000 description 1
• CDUFCLSAQHSOPG-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[(7-methyl-2-oxo-1h-quinolin-5-yl)oxy]propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound C1=CC(=O)NC2=CC(C)=CC(OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O)=C21 CDUFCLSAQHSOPG-UHFFFAOYSA-N 0.000 description 1
• VKJVGVCYQIPPHJ-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[(7-methyl-2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]propyl]amino]ethylamino]-5-oxopentan-2-yl] nitrate Chemical compound N1C(=O)CCC2=C1C=C(C)C=C2OCC(O)CNCCNC(=O)CCC(C)O[N+]([O-])=O VKJVGVCYQIPPHJ-UHFFFAOYSA-N 0.000 description 1
• PRKPVHQOMMKYJD-UHFFFAOYSA-N [5-[2-[[2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound COCCC1=CC=C(OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O)C=C1 PRKPVHQOMMKYJD-UHFFFAOYSA-N 0.000 description 1
• QFSKXBWHVAJZQN-UHFFFAOYSA-N [5-[2-[[3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCCNCC(O)COC1=CC=CC=C1C1CCCC1 QFSKXBWHVAJZQN-UHFFFAOYSA-N 0.000 description 1
• NRYQQYUPJARCLH-UHFFFAOYSA-N [5-[2-[[3-[(2,6-dimethyl-1h-indol-4-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound C1=C(C)C=C2NC(C)=CC2=C1OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O NRYQQYUPJARCLH-UHFFFAOYSA-N 0.000 description 1
• OPKKYSIZKZUDFI-UHFFFAOYSA-N [5-[2-[[3-[(3-cyano-6-methyl-1h-indol-4-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound CC1=CC(OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O)=C2C(C#N)=CNC2=C1 OPKKYSIZKZUDFI-UHFFFAOYSA-N 0.000 description 1
• DGLCZJMKEIVKAV-UHFFFAOYSA-N [5-[2-[[3-[(8-acetamido-2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]ethylamino]-5-oxopentyl] nitrate Chemical compound C1CC(=O)NC2=C1C(OCC(O)CNCCNC(=O)CCCCO[N+]([O-])=O)=CC=C2NC(=O)C DGLCZJMKEIVKAV-UHFFFAOYSA-N 0.000 description 1
• FKQAAFWYNWHKAE-UHFFFAOYSA-N [5-[[2-[(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]-2-methylpropyl]amino]-5-oxopentan-2-yl] nitrate Chemical compound C1=CC=C2C(OCC(O)CNC(C)(C)CNC(=O)CCC(C)O[N+]([O-])=O)=CC=CC2=C1 FKQAAFWYNWHKAE-UHFFFAOYSA-N 0.000 description 1
• FIMBFNSGSRFYMT-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound COC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O FIMBFNSGSRFYMT-UHFFFAOYSA-N 0.000 description 1
• ITXFSENFDHQLQF-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-(2-methylsulfanylphenoxy)propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound CSC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O ITXFSENFDHQLQF-UHFFFAOYSA-N 0.000 description 1
• JXACAKBZFXVXMM-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]amino]-2-methylpropyl]amino]-5-oxopentan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CCC(=O)NCC(C)(C)NCC(O)COC1=CC(C)=C(O)C(C)=C1C JXACAKBZFXVXMM-UHFFFAOYSA-N 0.000 description 1
• FPNDTZSERQUZHZ-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound CC1=CC(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)=C(C)C(C)=C1O FPNDTZSERQUZHZ-UHFFFAOYSA-N 0.000 description 1
• AHYSMUCALINRGN-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-[(3-oxo-1,2-dihydroinden-4-yl)oxy]propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1C(=O)CC2 AHYSMUCALINRGN-UHFFFAOYSA-N 0.000 description 1
• ZNYJGDJJQPFFML-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-[(7-methyl-2-oxo-1h-quinolin-5-yl)oxy]propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound C1=CC(=O)NC2=CC(C)=CC(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)=C21 ZNYJGDJJQPFFML-UHFFFAOYSA-N 0.000 description 1
• QYGAIDDYJSIWPK-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-[2-[2-(methylamino)-2-oxoethoxy]phenoxy]propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound CNC(=O)COC1=CC=CC=C1OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O QYGAIDDYJSIWPK-UHFFFAOYSA-N 0.000 description 1
• HBKFYARWKSGWJO-UHFFFAOYSA-N [5-[[2-[[2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound COCCC1=CC=C(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)C=C1 HBKFYARWKSGWJO-UHFFFAOYSA-N 0.000 description 1
• SQMTXVXKDHFGAM-UHFFFAOYSA-N [5-[[2-[[3-(2,5-dichlorophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCC(C)(C)NCC(O)COC1=CC(Cl)=CC=C1Cl SQMTXVXKDHFGAM-UHFFFAOYSA-N 0.000 description 1
• VQAXSMSTBXZWSW-UHFFFAOYSA-N [5-[[2-[[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CCC(=O)NCC(C)(C)NCC(O)COC1=CC(C)=CC=C1Cl VQAXSMSTBXZWSW-UHFFFAOYSA-N 0.000 description 1
• JMMJUQKTVVKJQR-UHFFFAOYSA-N [5-[[2-[[3-(2-chloro-5-methylphenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)=C1 JMMJUQKTVVKJQR-UHFFFAOYSA-N 0.000 description 1
• UXWDJDKJYKEWFC-UHFFFAOYSA-N [5-[[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC=C1C#N UXWDJDKJYKEWFC-UHFFFAOYSA-N 0.000 description 1
• ZOOOBGLWYRMUIY-UHFFFAOYSA-N [5-[[2-[[3-(2-cyclopentylphenoxy)-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC=C1C1CCCC1 ZOOOBGLWYRMUIY-UHFFFAOYSA-N 0.000 description 1
• FFSUJOOCMZPHGJ-UHFFFAOYSA-N [5-[[2-[[3-[(2-cyano-1h-indol-4-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound [O-][N+](=O)OCCCCC(=O)NCC(C)(C)NCC(O)COC1=CC=CC2=C1C=C(C#N)N2 FFSUJOOCMZPHGJ-UHFFFAOYSA-N 0.000 description 1
• OCRAWANRMXPJNN-UHFFFAOYSA-N [5-[[2-[[3-[(3-cyano-2h-chromen-8-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound C1=C(C#N)COC2=C1C=CC=C2OCC(O)CNC(C)(CNC(=O)CCCCO[N+]([O-])=O)C OCRAWANRMXPJNN-UHFFFAOYSA-N 0.000 description 1
• VBJSUKBTBMNBNB-UHFFFAOYSA-N [5-[[2-[[3-[(3-cyano-7-methyl-2-oxo-1h-quinolin-5-yl)oxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound C1=C(C#N)C(=O)NC2=CC(C)=CC(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)=C21 VBJSUKBTBMNBNB-UHFFFAOYSA-N 0.000 description 1
• JIHNCNYSOIORSR-UHFFFAOYSA-N [5-[[2-[[3-[4-(butanoylamino)-2-cyanophenoxy]-2-hydroxypropyl]amino]-2-methylpropyl]amino]-5-oxopentyl] nitrate Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)(C)CNC(=O)CCCCO[N+]([O-])=O)C(C#N)=C1 JIHNCNYSOIORSR-UHFFFAOYSA-N 0.000 description 1
• BBZWRXGYFXZVDG-UHFFFAOYSA-N [6-[2-[[2-hydroxy-3-[(2-methyl-1h-indol-4-yl)oxy]propyl]amino]ethylamino]-6-oxohexan-2-yl] nitrate Chemical compound [O-][N+](=O)OC(C)CCCC(=O)NCCNCC(O)COC1=CC=CC2=C1C=C(C)N2 BBZWRXGYFXZVDG-UHFFFAOYSA-N 0.000 description 1
• LESMLCREAPBXCL-UHFFFAOYSA-N [O-][N+](=O)OC(C)CCC(=O)NCCN Chemical compound [O-][N+](=O)OC(C)CCC(=O)NCCN LESMLCREAPBXCL-UHFFFAOYSA-N 0.000 description 1
• BNNVINXNNLOWDE-UHFFFAOYSA-N [O-][N+](=O)OC(CC)C(=O)NCCN Chemical compound [O-][N+](=O)OC(CC)C(=O)NCCN BNNVINXNNLOWDE-UHFFFAOYSA-N 0.000 description 1
• KIWBBUAFBKLIII-UHFFFAOYSA-N [O-][N+](=O)OCCON(C(=O)C)CCNCC(O)COC1=CC(C)=C(O)C(C)=C1C Chemical compound [O-][N+](=O)OCCON(C(=O)C)CCNCC(O)COC1=CC(C)=C(O)C(C)=C1C KIWBBUAFBKLIII-UHFFFAOYSA-N 0.000 description 1
• RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 150000008065 acid anhydrides Chemical class 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 235000010419 agar Nutrition 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910001508 alkali metal halide Inorganic materials 0.000 description 1
• 150000008045 alkali metal halides Chemical class 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
• 125000004848 alkoxyethyl group Chemical group 0.000 description 1
• 125000004849 alkoxymethyl group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000005239 aroylamino group Chemical group 0.000 description 1
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
• 239000012964 benzotriazole Substances 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 230000001588 bifunctional effect Effects 0.000 description 1
• 230000036772 blood pressure Effects 0.000 description 1
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• 229910052794 bromium Inorganic materials 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• DDYAZDRFUVZBMM-UHFFFAOYSA-N chloro-[chloro-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)O[Si](Cl)(C(C)C)C(C)C DDYAZDRFUVZBMM-UHFFFAOYSA-N 0.000 description 1
• 239000007979 citrate buffer Substances 0.000 description 1
• 239000008139 complexing agent Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006612 decyloxy group Chemical group 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
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