NO844560L - Nye amidforbindelser. - Google Patents

Info

Publication number

NO844560L

NO844560L NO844560A NO844560A NO844560L NO 844560 L NO844560 L NO 844560L NO 844560 A NO844560 A NO 844560A NO 844560 A NO844560 A NO 844560A NO 844560 L NO844560 L NO 844560L

Authority

NO

Norway

Prior art keywords

lower alkyl

phenyl

substituted

formula

alkyl

Prior art date

1983-11-16

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• -1 heterocyclic aryl radical Chemical class 0.000 claims description 322
• 150000001875 compounds Chemical class 0.000 claims description 287
• 125000000217 alkyl group Chemical group 0.000 claims description 269
• 239000000203 mixture Substances 0.000 claims description 155
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 154
• 125000003282 alkyl amino group Chemical group 0.000 claims description 113
• 238000000034 method Methods 0.000 claims description 109
• 125000003545 alkoxy group Chemical group 0.000 claims description 108
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 92
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 84
• 239000001257 hydrogen Substances 0.000 claims description 78
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 229910052736 halogen Inorganic materials 0.000 claims description 75
• 150000002367 halogens Chemical class 0.000 claims description 75
• 150000003839 salts Chemical class 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
• 125000002947 alkylene group Chemical group 0.000 claims description 59
• 125000004432 carbon atom Chemical group C* 0.000 claims description 58
• 229910052757 nitrogen Inorganic materials 0.000 claims description 56
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
• 150000002431 hydrogen Chemical class 0.000 claims description 44
• 230000003287 optical effect Effects 0.000 claims description 38
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 36
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 35
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
• 125000001544 thienyl group Chemical group 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 28
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 125000002541 furyl group Chemical group 0.000 claims description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 23
• 125000004414 alkyl thio group Chemical group 0.000 claims description 22
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 21
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000004423 acyloxy group Chemical group 0.000 claims description 19
• 239000000126 substance Substances 0.000 claims description 19
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 17
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 16
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 16
• 125000002837 carbocyclic group Chemical group 0.000 claims description 16
• 125000001589 carboacyl group Chemical group 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• JPXPPUOCSLMCHK-CQSZACIVSA-N 76093-33-9 Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-CQSZACIVSA-N 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 238000012546 transfer Methods 0.000 claims description 10
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical group C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000004306 triazinyl group Chemical group 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000000369 oxido group Chemical group [*]=O 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 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
• UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• 239000012876 carrier material Substances 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
• 235000019441 ethanol Nutrition 0.000 description 71
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
• 235000002639 sodium chloride Nutrition 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
• 229910052740 iodine Inorganic materials 0.000 description 49
• 239000000155 melt Substances 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 38
• 239000007858 starting material Substances 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• 239000012043 crude product Substances 0.000 description 25
• HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 24
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 238000001953 recrystallisation Methods 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• 239000000243 solution Substances 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 150000002148 esters Chemical class 0.000 description 18
• 239000013543 active substance Substances 0.000 description 17
• DNIMLZXXCIKJEJ-UHFFFAOYSA-N 5-o-(benzotriazol-1-yl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)ON2C3=CC=CC=C3N=N2)C1C1=CC=CC([N+]([O-])=O)=C1 DNIMLZXXCIKJEJ-UHFFFAOYSA-N 0.000 description 15
• JPXPPUOCSLMCHK-AWEZNQCLSA-N 76093-34-0 Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-AWEZNQCLSA-N 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
• 239000012452 mother liquor Substances 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 150000001408 amides Chemical class 0.000 description 12
• 238000010828 elution Methods 0.000 description 12
• 229910052783 alkali metal Inorganic materials 0.000 description 11
• 150000001340 alkali metals Chemical class 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 238000000926 separation method Methods 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 description 8
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 150000001298 alcohols Chemical class 0.000 description 7
• 229910021529 ammonia Inorganic materials 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 150000004820 halides Chemical class 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 150000003254 radicals Chemical class 0.000 description 7
• 235000011121 sodium hydroxide Nutrition 0.000 description 7
• 238000001228 spectrum Methods 0.000 description 7
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 150000002430 hydrocarbons Chemical group 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 5
• 241000700199 Cavia porcellus Species 0.000 description 5
• 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 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• 125000005907 alkyl ester group Chemical group 0.000 description 5
• 150000001718 carbodiimides Chemical class 0.000 description 5
• PQGVTLQEKCJXKF-RGMNGODLSA-N ethyl (2s)-2-amino-3-methylbutanoate;hydron;chloride Chemical compound Cl.CCOC(=O)[C@@H](N)C(C)C PQGVTLQEKCJXKF-RGMNGODLSA-N 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 238000011065 in-situ storage Methods 0.000 description 5
• XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 5
• 230000000144 pharmacologic effect Effects 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
• UECYYFDIHJZYMZ-UHFFFAOYSA-N 5-o-(benzotriazol-1-yl) 3-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)ON2C3=CC=CC=C3N=N2)C1C1=CC=CC([N+]([O-])=O)=C1 UECYYFDIHJZYMZ-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 150000008064 anhydrides Chemical class 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 150000001735 carboxylic acids Chemical class 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 238000009833 condensation Methods 0.000 description 4
• 230000005494 condensation Effects 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 238000002955 isolation Methods 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• QWMSYUSMUAIXLK-PMACEKPBSA-N methyl (4s)-5-[[(2s)-1-ethoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)[C@H](C(C)C)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 QWMSYUSMUAIXLK-PMACEKPBSA-N 0.000 description 4
• 150000002829 nitrogen Chemical class 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
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• QWMSYUSMUAIXLK-WOJBJXKFSA-N methyl (4r)-5-[[(2r)-1-ethoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)[C@@H](C(C)C)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 QWMSYUSMUAIXLK-WOJBJXKFSA-N 0.000 description 1
• QWMSYUSMUAIXLK-UXHICEINSA-N methyl (4r)-5-[[(2s)-1-ethoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)[C@H](C(C)C)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 QWMSYUSMUAIXLK-UXHICEINSA-N 0.000 description 1
• OWTZJWDBADWQJZ-DYXDTQHNSA-N methyl (4r)-5-[[(2s,3s)-1-ethoxy-3-methyl-1-oxopentan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)[C@H]([C@@H](C)CC)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 OWTZJWDBADWQJZ-DYXDTQHNSA-N 0.000 description 1
• LNLKWYYWTXMVHD-APWZRJJASA-N methyl (4s)-5-[(2r)-2-methoxycarbonylpyrrolidine-1-carbonyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)[C@H]1CCCN1C(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 LNLKWYYWTXMVHD-APWZRJJASA-N 0.000 description 1
• PSKSWOUBRFDALM-FCHUYYIVSA-N methyl (4s)-5-[[(2r)-1-butoxy-3-methyl-1-oxobutan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCCCOC(=O)[C@@H](C(C)C)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 PSKSWOUBRFDALM-FCHUYYIVSA-N 0.000 description 1
• VXOHXIWBKDZISL-VXKWHMMOSA-N methyl (4s)-5-[[(2s)-1-[2-(dimethylamino)ethoxy]-3-methyl-1-oxobutan-2-yl]carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)N[C@@H](C(C)C)C(=O)OCCN(C)C)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 VXOHXIWBKDZISL-VXKWHMMOSA-N 0.000 description 1
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• PDZLODHDCYUSKL-UHFFFAOYSA-N methyl 5-[(1-ethoxy-2-methyl-1-oxopropan-2-yl)carbamoyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C(C)(C)NC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PDZLODHDCYUSKL-UHFFFAOYSA-N 0.000 description 1
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