DD153207A5 - Verfahren zur herstellung von neuen carbonsaeureamiden - Google Patents
Verfahren zur herstellung von neuen carbonsaeureamiden Download PDFInfo
- Publication number
- DD153207A5 DD153207A5 DD222511A DD22251180A DD153207A5 DD 153207 A5 DD153207 A5 DD 153207A5 DD 222511 A DD222511 A DD 222511A DD 22251180 A DD22251180 A DD 22251180A DD 153207 A5 DD153207 A5 DD 153207A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- general formula
- carbon atoms
- benzoic acid
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- 239000002253 acid Substances 0.000 claims abstract description 114
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- -1 hydroxy, nitro, amino Chemical group 0.000 claims description 395
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 151
- 239000000460 chlorine Substances 0.000 claims description 146
- 125000004432 carbon atom Chemical group C* 0.000 claims description 134
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 239000002904 solvent Substances 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 28
- 229910052740 iodine Inorganic materials 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims description 19
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 13
- 239000012954 diazonium Substances 0.000 claims description 13
- 150000001989 diazonium salts Chemical class 0.000 claims description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 150000007530 organic bases Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 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 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 238000006359 acetalization reaction Methods 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000006264 debenzylation reaction Methods 0.000 claims description 3
- 238000005695 dehalogenation reaction Methods 0.000 claims description 3
- 238000007323 disproportionation reaction Methods 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- 125000005469 ethylenyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 241001521416 Leva Species 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000004060 metabolic process Effects 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 321
- 230000008018 melting Effects 0.000 description 321
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 284
- 239000005711 Benzoic acid Substances 0.000 description 171
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 154
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 154
- 229960000583 acetic acid Drugs 0.000 description 134
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 127
- 235000010233 benzoic acid Nutrition 0.000 description 125
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 124
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 116
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 88
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 83
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 75
- 239000000243 solution Substances 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
- RBLUWLZGAZETKS-UHFFFAOYSA-N ethyl 4-(2-aminoethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CCN)C=C1 RBLUWLZGAZETKS-UHFFFAOYSA-N 0.000 description 49
- 235000019441 ethanol Nutrition 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 38
- 229910002027 silica gel Inorganic materials 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 33
- 150000002148 esters Chemical class 0.000 description 32
- 125000004494 ethyl ester group Chemical group 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 27
- 230000008020 evaporation Effects 0.000 description 27
- 235000011121 sodium hydroxide Nutrition 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 238000007127 saponification reaction Methods 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 23
- 235000011152 sodium sulphate Nutrition 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 18
- 150000004702 methyl esters Chemical class 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- XGBXOGQDEAGJKO-UHFFFAOYSA-N methyl 4-(2-aminoethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCN)C=C1 XGBXOGQDEAGJKO-UHFFFAOYSA-N 0.000 description 13
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 description 12
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 235000010288 sodium nitrite Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000002026 chloroform extract Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- JOTMFOWEVMXFHO-UHFFFAOYSA-N 2-aminoethyl benzoate Chemical compound NCCOC(=O)C1=CC=CC=C1 JOTMFOWEVMXFHO-UHFFFAOYSA-N 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 7
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- MRBFWTDIRYEDBQ-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid Chemical compound NCCC1=CC=C(C(O)=O)C=C1 MRBFWTDIRYEDBQ-UHFFFAOYSA-N 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229940095076 benzaldehyde Drugs 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QUEKGYQTRJVEQC-UHFFFAOYSA-N 2516-96-3 Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl QUEKGYQTRJVEQC-UHFFFAOYSA-N 0.000 description 4
- MHZVXMASUGURKJ-UHFFFAOYSA-N 5-chloro-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCCCC1 MHZVXMASUGURKJ-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- XSXVXSCMWUJXOS-UHFFFAOYSA-N ethyl 2-ethylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1CC XSXVXSCMWUJXOS-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 150000002905 orthoesters Chemical class 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- AWUSNAPJSJWXMU-UHFFFAOYSA-N 2-(azepan-1-yl)-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCCCCC1 AWUSNAPJSJWXMU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- TYTDINDFLWOUBN-UHFFFAOYSA-N 5-chloro-2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(Cl)C=C1C(O)=O TYTDINDFLWOUBN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- KWYLWYSUPXFVJH-UHFFFAOYSA-N 2-(azepan-1-yl)-5-methoxybenzoic acid Chemical compound COc1ccc(N2CCCCCC2)c(c1)C(O)=O KWYLWYSUPXFVJH-UHFFFAOYSA-N 0.000 description 2
- XBHJNYIJWKCFCI-PHIMTYICSA-N 2-[(3R,5S)-3,5-dimethylpiperidin-1-yl]-5-methoxybenzoic acid Chemical compound COC=1C=CC(=C(C(=O)O)C=1)N1C[C@H](C[C@H](C1)C)C XBHJNYIJWKCFCI-PHIMTYICSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- USWQSSAXKAYZII-UHFFFAOYSA-N 3-chloro-2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=C(Cl)C=CC=C1C(O)=O USWQSSAXKAYZII-UHFFFAOYSA-N 0.000 description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 2
- LEJHUEWYEKQILF-UHFFFAOYSA-N 4-chloro-5-nitro-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1N1CCCCC1 LEJHUEWYEKQILF-UHFFFAOYSA-N 0.000 description 2
- QBZVDIRFIDFVQA-UHFFFAOYSA-N 5-bromo-2-(2-methylpiperidin-1-yl)benzoic acid Chemical compound CC1CCCCN1C1=CC=C(Br)C=C1C(O)=O QBZVDIRFIDFVQA-UHFFFAOYSA-N 0.000 description 2
- UZVFXYNDMSDNBT-UHFFFAOYSA-N 5-chloro-2-(4-ethoxycarbonylpiperidin-1-yl)benzoic acid Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C(Cl)C=C1C(O)=O UZVFXYNDMSDNBT-UHFFFAOYSA-N 0.000 description 2
- KTGQRSBFFISBHO-UHFFFAOYSA-N 5-chloro-2-(4-propan-2-ylpiperidin-1-yl)benzoic acid Chemical compound C1CC(C(C)C)CCN1C1=CC=C(Cl)C=C1C(O)=O KTGQRSBFFISBHO-UHFFFAOYSA-N 0.000 description 2
- OCHGCLDQVKXWFT-UHFFFAOYSA-N 5-chloro-2-(n-methylanilino)benzoic acid Chemical compound C=1C=C(Cl)C=C(C(O)=O)C=1N(C)C1=CC=CC=C1 OCHGCLDQVKXWFT-UHFFFAOYSA-N 0.000 description 2
- ITNCLVAQRUEBAM-AOOOYVTPSA-N 5-chloro-2-[(3s,5r)-3,5-dimethylpiperidin-1-yl]benzoic acid Chemical compound C1[C@@H](C)C[C@@H](C)CN1C1=CC=C(Cl)C=C1C(O)=O ITNCLVAQRUEBAM-AOOOYVTPSA-N 0.000 description 2
- RLUBLRQPRBPJGQ-UHFFFAOYSA-N 5-chloro-2-[cyclohexyl(2-methylpropyl)amino]benzoic acid Chemical compound C=1C=C(Cl)C=C(C(O)=O)C=1N(CC(C)C)C1CCCCC1 RLUBLRQPRBPJGQ-UHFFFAOYSA-N 0.000 description 2
- HCXWVEFBJYGVAM-UHFFFAOYSA-N 5-chloro-2-morpholin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCOCC1 HCXWVEFBJYGVAM-UHFFFAOYSA-N 0.000 description 2
- LEMIJOINGPOVQV-UHFFFAOYSA-N 5-chloro-2-pyrrolidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCCC1 LEMIJOINGPOVQV-UHFFFAOYSA-N 0.000 description 2
- YLTYULRTQLHZNV-UHFFFAOYSA-N 5-chloro-2-thiomorpholin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCSCC1 YLTYULRTQLHZNV-UHFFFAOYSA-N 0.000 description 2
- RQRBLTZTXJRFDD-UHFFFAOYSA-N 5-hexoxy-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(OCCCCCC)=CC=C1N1CCCCC1 RQRBLTZTXJRFDD-UHFFFAOYSA-N 0.000 description 2
- CYPOVTAFMRLRCW-UHFFFAOYSA-N 5-nitro-2,4-di(piperidin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(N2CCCCC2)C=C1N1CCCCC1 CYPOVTAFMRLRCW-UHFFFAOYSA-N 0.000 description 2
- BJOSCVBMMPNMLK-UHFFFAOYSA-N 5-phenylmethoxy-2-piperidin-1-ylbenzoic acid Chemical compound C=1C=C(N2CCCCC2)C(C(=O)O)=CC=1OCC1=CC=CC=C1 BJOSCVBMMPNMLK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- KGBMIAYNJRCVGH-UHFFFAOYSA-N ethyl 2-(2-aminoethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCN KGBMIAYNJRCVGH-UHFFFAOYSA-N 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- URYAVPPYTHJURP-UHFFFAOYSA-N ethyl benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=CC=C1 URYAVPPYTHJURP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- IYDBWBQCKQHHPA-UHFFFAOYSA-N methyl 2-(2-aminoethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CCN IYDBWBQCKQHHPA-UHFFFAOYSA-N 0.000 description 2
- KQQKFHNRMJHXLR-UHFFFAOYSA-N methyl 2-ethylbenzoate Chemical compound CCC1=CC=CC=C1C(=O)OC KQQKFHNRMJHXLR-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 101150068774 thyX gene Proteins 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- RHBGITBPARBDPH-ZPUQHVIOSA-N (E,E)-piperic acid Chemical group OC(=O)\C=C\C=C\C1=CC=C2OCOC2=C1 RHBGITBPARBDPH-ZPUQHVIOSA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 1
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- LMGYOBQJBQAZKC-UHFFFAOYSA-N 1-(2-ethylphenyl)-2-hydroxy-2-phenylethanone Chemical compound CCC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 LMGYOBQJBQAZKC-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical group CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- XDHOEHJVXXTEDV-UHFFFAOYSA-N 1-ethoxyprop-1-ene Chemical group CCOC=CC XDHOEHJVXXTEDV-UHFFFAOYSA-N 0.000 description 1
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- TXJUTRJFNRYTHH-UHFFFAOYSA-N 1h-3,1-benzoxazine-2,4-dione Chemical class C1=CC=C2C(=O)OC(=O)NC2=C1 TXJUTRJFNRYTHH-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 1
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 1
- SQGIOBQKNXOJTC-UHFFFAOYSA-N 2,4-diethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C(CC)=C1 SQGIOBQKNXOJTC-UHFFFAOYSA-N 0.000 description 1
- NCSLSNBZPNXIBP-UHFFFAOYSA-N 2-(1,2,4,5,5a,6,7,8,9,9a-decahydrobenzo[d]azepin-3-yl)-5-aminobenzoic acid Chemical compound OC(=O)C1=CC(N)=CC=C1N1CCC2CCCCC2CC1 NCSLSNBZPNXIBP-UHFFFAOYSA-N 0.000 description 1
- JZGMTBXIAZMCBM-UHFFFAOYSA-N 2-(1,2,4,5,5a,6,7,8,9,9a-decahydrobenzo[d]azepin-3-yl)-5-bromobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1N1CCC2CCCCC2CC1 JZGMTBXIAZMCBM-UHFFFAOYSA-N 0.000 description 1
- DRNZCKFDAGHCGO-UHFFFAOYSA-N 2-(1,2,4,5,5a,6,7,8,9,9a-decahydrobenzo[d]azepin-3-yl)-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCC2CCCCC2CC1 DRNZCKFDAGHCGO-UHFFFAOYSA-N 0.000 description 1
- NXHPJMQPCZEENH-UHFFFAOYSA-N 2-(1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CC2CCCCC2C1 NXHPJMQPCZEENH-UHFFFAOYSA-N 0.000 description 1
- GURPUCJRJDWTBI-UHFFFAOYSA-N 2-(2-aminopropyl)benzoic acid Chemical compound CC(N)CC1=CC=CC=C1C(O)=O GURPUCJRJDWTBI-UHFFFAOYSA-N 0.000 description 1
- OZCUCQLHGQMOAV-UHFFFAOYSA-N 2-(2-azaniumylethyl)benzoate Chemical compound NCCC1=CC=CC=C1C(O)=O OZCUCQLHGQMOAV-UHFFFAOYSA-N 0.000 description 1
- ARCGWSIHHQVAJL-UHFFFAOYSA-N 2-(2-methylpiperidin-1-yl)-5-nitrobenzoic acid Chemical compound CC1CCCCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O ARCGWSIHHQVAJL-UHFFFAOYSA-N 0.000 description 1
- HHOHKKOVPZTCLA-UHFFFAOYSA-N 2-(2-methylpiperidin-1-yl)benzoic acid Chemical compound CC1CCCCN1C1=CC=CC=C1C(O)=O HHOHKKOVPZTCLA-UHFFFAOYSA-N 0.000 description 1
- HNTSIQICPWAIER-UHFFFAOYSA-N 2-(3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl)-5-nitrobenzoic acid Chemical compound C1N(CCC2CCCCC12)C1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-] HNTSIQICPWAIER-UHFFFAOYSA-N 0.000 description 1
- HCVFLTYSLOFRCI-UHFFFAOYSA-N 2-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CC2CCCCC2CC1 HCVFLTYSLOFRCI-UHFFFAOYSA-N 0.000 description 1
- RBARJOPUOKMYJM-UHFFFAOYSA-N 2-(3,5-dimethylpiperidin-1-yl)-5-nitrobenzoic acid Chemical compound C1C(C)CC(C)CN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O RBARJOPUOKMYJM-UHFFFAOYSA-N 0.000 description 1
- YADYXZROCIDALP-UHFFFAOYSA-N 2-(3,5-dimethylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)CC(C)CN1C1=CC=CC=C1C(O)=O YADYXZROCIDALP-UHFFFAOYSA-N 0.000 description 1
- DIQJRFDFQZDOTB-UHFFFAOYSA-N 2-(3,5-dimethylthiomorpholin-4-yl)-5-nitrobenzoic acid Chemical compound CC1CSCC(C)N1C1=CC=C([N+]([O-])=O)C=C1C(O)=O DIQJRFDFQZDOTB-UHFFFAOYSA-N 0.000 description 1
- QOEMYWHGIQIVQX-UHFFFAOYSA-N 2-(3-methylpiperidin-1-yl)-5-nitrobenzoic acid Chemical compound C1C(C)CCCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O QOEMYWHGIQIVQX-UHFFFAOYSA-N 0.000 description 1
- KKHPZMVOPGYMHD-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-chlorobenzoic acid hydrochloride Chemical compound Cl.C(C1=CC=CC=C1)N1CCN(CC1)C1=C(C(=O)O)C=C(C=C1)Cl KKHPZMVOPGYMHD-UHFFFAOYSA-N 0.000 description 1
- SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 description 1
- ZLASGXOTUKQSAT-UHFFFAOYSA-N 2-(4-ethoxycarbonylpiperazin-1-yl)-5-nitrobenzoic acid Chemical compound C1CN(C(=O)OCC)CCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O ZLASGXOTUKQSAT-UHFFFAOYSA-N 0.000 description 1
- FQZBRAJJMZZXSV-UHFFFAOYSA-N 2-(4-ethoxycarbonylpiperidin-1-yl)-5-nitrobenzoic acid Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O FQZBRAJJMZZXSV-UHFFFAOYSA-N 0.000 description 1
- ZMRKWYMLWHYGLO-UHFFFAOYSA-N 2-(4-methoxypiperidin-1-yl)-5-nitrobenzoic acid Chemical compound C1CC(OC)CCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O ZMRKWYMLWHYGLO-UHFFFAOYSA-N 0.000 description 1
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 description 1
- FMAYFDOGXDJAAR-UHFFFAOYSA-N 2-(4-tert-butylpiperidin-1-yl)-5-methoxybenzoic acid Chemical compound CC(C)(C)C1CCN(CC1)C2=C(C=C(C=C2)OC)C(=O)O FMAYFDOGXDJAAR-UHFFFAOYSA-N 0.000 description 1
- NRMGEVANPNQOFQ-UHFFFAOYSA-N 2-(4-tert-butylpiperidin-1-yl)-5-nitrobenzoic acid Chemical compound C(C)(C)(C)C1CCN(CC1)C1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-] NRMGEVANPNQOFQ-UHFFFAOYSA-N 0.000 description 1
- XCVVJJCXGYGILD-UHFFFAOYSA-N 2-(azepan-1-yl)-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1N1CCCCCC1 XCVVJJCXGYGILD-UHFFFAOYSA-N 0.000 description 1
- QOJMMCVSGRDNJA-UHFFFAOYSA-N 2-(azepan-1-yl)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCCCCC1 QOJMMCVSGRDNJA-UHFFFAOYSA-N 0.000 description 1
- RMRIEQUDBWUVQQ-UHFFFAOYSA-N 2-(dimethylamino)-5-fluorobenzoic acid Chemical compound CN(C)C1=CC=C(F)C=C1C(O)=O RMRIEQUDBWUVQQ-UHFFFAOYSA-N 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- RBARJOPUOKMYJM-UWVGGRQHSA-N 2-[(3S,5S)-3,5-dimethylpiperidin-1-yl]-5-nitrobenzoic acid Chemical compound C[C@@H]1CN(C[C@H](C1)C)C1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-] RBARJOPUOKMYJM-UWVGGRQHSA-N 0.000 description 1
- OFWGPDGSUXWDRC-AOOOYVTPSA-N 2-[(3s,5r)-3,5-dimethylpiperidin-1-yl]-5-hydroxybenzoic acid Chemical compound C1[C@@H](C)C[C@@H](C)CN1C1=CC=C(O)C=C1C(O)=O OFWGPDGSUXWDRC-AOOOYVTPSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- SLJIKKRTQUDACV-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-5-chlorobenzoic acid Chemical compound C=1C=C(Cl)C=C(C(O)=O)C=1N(C)CC1=CC=CC=C1 SLJIKKRTQUDACV-UHFFFAOYSA-N 0.000 description 1
- HCZNADAWKQXMGG-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-5-nitrobenzoic acid Chemical compound C=1C=C([N+]([O-])=O)C=C(C(O)=O)C=1N(C)CC1=CC=CC=C1 HCZNADAWKQXMGG-UHFFFAOYSA-N 0.000 description 1
- NKTKQUOKRJNDFU-UHFFFAOYSA-N 2-[benzyl(methyl)amino]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1N(C)CC1=CC=CC=C1 NKTKQUOKRJNDFU-UHFFFAOYSA-N 0.000 description 1
- AJRSIXXDGPFIQN-UHFFFAOYSA-N 2-[bis(2-methylpropyl)amino]-5-chlorobenzoic acid Chemical compound CC(C)CN(CC(C)C)C1=CC=C(Cl)C=C1C(O)=O AJRSIXXDGPFIQN-UHFFFAOYSA-N 0.000 description 1
- IGMFWKIEEYQDNZ-UHFFFAOYSA-N 2-[cyclohexyl(2-methylpropyl)amino]-5-nitrobenzoic acid Chemical compound C=1C=C([N+]([O-])=O)C=C(C(O)=O)C=1N(CC(C)C)C1CCCCC1 IGMFWKIEEYQDNZ-UHFFFAOYSA-N 0.000 description 1
- RKOPXRFETZMONP-UHFFFAOYSA-N 2-[cyclohexyl(ethyl)amino]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1N(CC)C1CCCCC1 RKOPXRFETZMONP-UHFFFAOYSA-N 0.000 description 1
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 1
- RBCPJQQJBAQSOU-UHFFFAOYSA-N 2-bromo-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Br RBCPJQQJBAQSOU-UHFFFAOYSA-N 0.000 description 1
- IAKUNNMLUJHOAF-UHFFFAOYSA-N 2-chloro-6-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(Cl)=C1C(O)=O IAKUNNMLUJHOAF-UHFFFAOYSA-N 0.000 description 1
- BVLYMNSAGPVROS-UHFFFAOYSA-N 2-ethylbenzoic acid;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(O)=O BVLYMNSAGPVROS-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XUBUJTVBAXQIKG-UHFFFAOYSA-N 2-morpholin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1CCOCC1 XUBUJTVBAXQIKG-UHFFFAOYSA-N 0.000 description 1
- MRCONLVSTRNJQT-UHFFFAOYSA-N 2-morpholino-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCOCC1 MRCONLVSTRNJQT-UHFFFAOYSA-N 0.000 description 1
- SKGAOJXVBPBIEM-UHFFFAOYSA-N 2-piperidin-1-yl-5-propan-2-yloxybenzoic acid Chemical compound OC(=O)C1=CC(OC(C)C)=CC=C1N1CCCCC1 SKGAOJXVBPBIEM-UHFFFAOYSA-N 0.000 description 1
- YNZJJMDTAFCBGO-UHFFFAOYSA-N 2-piperidin-1-ylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1N1CCCCC1 YNZJJMDTAFCBGO-UHFFFAOYSA-N 0.000 description 1
- GTYZDORKFFSTLS-UHFFFAOYSA-N 2h-3,1-benzoxazine Chemical compound C1=CC=CC2=NCOC=C21 GTYZDORKFFSTLS-UHFFFAOYSA-N 0.000 description 1
- PPJYSSNKSXAVDB-UHFFFAOYSA-N 3,3',5,5'-tetraiodothyroacetic acid Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 PPJYSSNKSXAVDB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LSPGLRSKFJOUMQ-UHFFFAOYSA-N 3-chloro-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1N1CCCCC1 LSPGLRSKFJOUMQ-UHFFFAOYSA-N 0.000 description 1
- NBKNFNAHFNVUOW-UHFFFAOYSA-N 3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CC(O)=O NBKNFNAHFNVUOW-UHFFFAOYSA-N 0.000 description 1
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- QPVBLLQBUNVSJT-UHFFFAOYSA-N 3-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=CC(C(O)=O)=C1 QPVBLLQBUNVSJT-UHFFFAOYSA-N 0.000 description 1
- BKMRWJWLBHHGCF-UHFFFAOYSA-N 4-(2-bromoethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCBr)C=C1 BKMRWJWLBHHGCF-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- ULVMSIJSDZNMHP-UHFFFAOYSA-N 4-chloro-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1N1CCCCC1 ULVMSIJSDZNMHP-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- VKJXAQYPOTYDLO-UHFFFAOYSA-N 4-methylphenethylamine Chemical compound CC1=CC=C(CCN)C=C1 VKJXAQYPOTYDLO-UHFFFAOYSA-N 0.000 description 1
- RQXQMUUSQGCLPL-UHFFFAOYSA-N 4-thiomorpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCSCC1 RQXQMUUSQGCLPL-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- YILAZDUANQYWIV-UHFFFAOYSA-N 5-amino-2-(2-methylpiperidin-1-yl)benzoic acid Chemical compound CC1CCCCN1C1=CC=C(N)C=C1C(O)=O YILAZDUANQYWIV-UHFFFAOYSA-N 0.000 description 1
- YNMNQZPTYJZGID-UHFFFAOYSA-N 5-amino-2-(3,3,5,5-tetramethylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)(C)CC(C)(C)CN1C1=CC=C(N)C=C1C(O)=O YNMNQZPTYJZGID-UHFFFAOYSA-N 0.000 description 1
- TYHRDGSAWMCTJR-UHFFFAOYSA-N 5-amino-2-(3,5-dimethylmorpholin-4-yl)benzoic acid Chemical compound CC1COCC(C)N1C1=CC=C(N)C=C1C(O)=O TYHRDGSAWMCTJR-UHFFFAOYSA-N 0.000 description 1
- HLHXVRSOPLAEAC-UHFFFAOYSA-N 5-amino-2-(3-methylpiperidin-1-ium-1-yl)benzoate Chemical compound C1C(C)CCCN1C1=CC=C(N)C=C1C(O)=O HLHXVRSOPLAEAC-UHFFFAOYSA-N 0.000 description 1
- FXOZKPCRGKAQAF-UHFFFAOYSA-N 5-amino-2-(4-ethoxycarbonylpiperazin-1-yl)benzoic acid Chemical compound C1CN(C(=O)OCC)CCN1C1=CC=C(N)C=C1C(O)=O FXOZKPCRGKAQAF-UHFFFAOYSA-N 0.000 description 1
- MLQUXRUGIUNMMH-UHFFFAOYSA-N 5-amino-2-(4-ethoxycarbonylpiperidin-1-yl)benzoic acid Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C(N)C=C1C(O)=O MLQUXRUGIUNMMH-UHFFFAOYSA-N 0.000 description 1
- WLIBXILRXKJRAY-UHFFFAOYSA-N 5-amino-2-(4-methylpiperidin-1-ium-1-yl)benzoate Chemical compound C1CC(C)CCN1C1=CC=C(N)C=C1C(O)=O WLIBXILRXKJRAY-UHFFFAOYSA-N 0.000 description 1
- YHQOIAWXAVZVEQ-UHFFFAOYSA-N 5-amino-2-(4-phenylpiperazin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC(N)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 YHQOIAWXAVZVEQ-UHFFFAOYSA-N 0.000 description 1
- ZYLJRULCPWPINV-UHFFFAOYSA-N 5-amino-2-(4-phenylpiperidin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC(N)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 ZYLJRULCPWPINV-UHFFFAOYSA-N 0.000 description 1
- ZQVWUNXJXNTRRY-UHFFFAOYSA-N 5-amino-2-(4-tert-butylpiperidin-1-yl)benzoic acid Chemical compound C1CC(C(C)(C)C)CCN1C1=CC=C(N)C=C1C(O)=O ZQVWUNXJXNTRRY-UHFFFAOYSA-N 0.000 description 1
- UZISGXPDDOVJGK-UHFFFAOYSA-N 5-amino-2-(5-ethyl-2-methylpiperidin-1-yl)benzoic acid Chemical compound C1C(CC)CCC(C)N1C1=CC=C(N)C=C1C(O)=O UZISGXPDDOVJGK-UHFFFAOYSA-N 0.000 description 1
- QSXVNKWWRYKSDG-UHFFFAOYSA-N 5-amino-2-(n-methylanilino)benzoic acid Chemical compound C=1C=C(N)C=C(C(O)=O)C=1N(C)C1=CC=CC=C1 QSXVNKWWRYKSDG-UHFFFAOYSA-N 0.000 description 1
- PEPUMPQTKIHPMR-AOOOYVTPSA-N 5-amino-2-[(3s,5r)-3,5-dimethylpiperidin-1-yl]benzoic acid Chemical compound C1[C@@H](C)C[C@@H](C)CN1C1=CC=C(N)C=C1C(O)=O PEPUMPQTKIHPMR-AOOOYVTPSA-N 0.000 description 1
- PEPUMPQTKIHPMR-UWVGGRQHSA-N 5-amino-2-[(3s,5s)-3,5-dimethylpiperidin-1-yl]benzoic acid Chemical compound C1[C@@H](C)C[C@H](C)CN1C1=CC=C(N)C=C1C(O)=O PEPUMPQTKIHPMR-UWVGGRQHSA-N 0.000 description 1
- AMBYEYBIHLSTKG-UHFFFAOYSA-N 5-amino-2-[butyl(cyclohexyl)amino]benzoic acid Chemical compound C=1C=C(N)C=C(C(O)=O)C=1N(CCCC)C1CCCCC1 AMBYEYBIHLSTKG-UHFFFAOYSA-N 0.000 description 1
- XHGJRPHMWRRIDE-UHFFFAOYSA-N 5-amino-2-morpholin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC(N)=CC=C1N1CCOCC1 XHGJRPHMWRRIDE-UHFFFAOYSA-N 0.000 description 1
- JGJCZZGVSPAUQF-UHFFFAOYSA-N 5-bromo-2-(4-methoxypiperidin-1-yl)benzoic acid Chemical compound C1CC(OC)CCN1C1=CC=C(Br)C=C1C(O)=O JGJCZZGVSPAUQF-UHFFFAOYSA-N 0.000 description 1
- CYTXUPXHVXSDML-UHFFFAOYSA-N 5-bromo-2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(Br)C=C1C(O)=O CYTXUPXHVXSDML-UHFFFAOYSA-N 0.000 description 1
- YGBHWEWVDIWHTJ-AOOOYVTPSA-N 5-bromo-2-[(3R,5S)-3,5-dimethylpiperidin-1-yl]benzoic acid Chemical compound BrC=1C=CC(=C(C(=O)O)C=1)N1C[C@H](C[C@H](C1)C)C YGBHWEWVDIWHTJ-AOOOYVTPSA-N 0.000 description 1
- DNDDHSSKHIAPCA-UHFFFAOYSA-N 5-bromo-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1N1CCCCC1 DNDDHSSKHIAPCA-UHFFFAOYSA-N 0.000 description 1
- ZPJWXHPYFLTQJQ-UHFFFAOYSA-N 5-chloro-2-(2,6-dimethylmorpholin-4-yl)benzoic acid Chemical compound C1C(C)OC(C)CN1C1=CC=C(Cl)C=C1C(O)=O ZPJWXHPYFLTQJQ-UHFFFAOYSA-N 0.000 description 1
- FYMPFLABUBWFSL-UHFFFAOYSA-N 5-chloro-2-(2,6-dimethylthiomorpholin-4-yl)benzoic acid Chemical compound C1C(C)SC(C)CN1C1=CC=C(Cl)C=C1C(O)=O FYMPFLABUBWFSL-UHFFFAOYSA-N 0.000 description 1
- ZPUQGJHIGUYDTP-UHFFFAOYSA-N 5-chloro-2-(2-methylpiperidin-1-yl)benzoic acid Chemical compound CC1CCCCN1C1=CC=C(Cl)C=C1C(O)=O ZPUQGJHIGUYDTP-UHFFFAOYSA-N 0.000 description 1
- OVZVMGBCOKCLBR-UHFFFAOYSA-N 5-chloro-2-(3,3,5,5-tetramethylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)(C)CC(C)(C)CN1C1=CC=C(Cl)C=C1C(O)=O OVZVMGBCOKCLBR-UHFFFAOYSA-N 0.000 description 1
- ZZNGGNLYPNZGIR-UHFFFAOYSA-N 5-chloro-2-(3,4,5,6,7,8-hexahydro-1h-isoquinolin-2-yl)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CC(CCCC2)=C2CC1 ZZNGGNLYPNZGIR-UHFFFAOYSA-N 0.000 description 1
- ITNCLVAQRUEBAM-UHFFFAOYSA-N 5-chloro-2-(3,5-dimethylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)CC(C)CN1C1=CC=C(Cl)C=C1C(O)=O ITNCLVAQRUEBAM-UHFFFAOYSA-N 0.000 description 1
- GSFBMSHQWXSKGP-UHFFFAOYSA-N 5-chloro-2-(3,5-dimethylthiomorpholin-4-yl)benzoic acid Chemical compound CC1CSCC(C)N1C1=CC=C(Cl)C=C1C(O)=O GSFBMSHQWXSKGP-UHFFFAOYSA-N 0.000 description 1
- VYUIBEZXJBXHKB-UHFFFAOYSA-N 5-chloro-2-(3-methylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)CCCN1C1=CC=C(Cl)C=C1C(O)=O VYUIBEZXJBXHKB-UHFFFAOYSA-N 0.000 description 1
- AVJODSRLMMOBFK-UHFFFAOYSA-N 5-chloro-2-(4-ethoxycarbonylpiperazin-1-yl)benzoic acid Chemical compound C1CN(C(=O)OCC)CCN1C1=CC=C(Cl)C=C1C(O)=O AVJODSRLMMOBFK-UHFFFAOYSA-N 0.000 description 1
- MNKKPODCJXOTFM-UHFFFAOYSA-N 5-chloro-2-(4-methoxypiperidin-1-yl)benzoic acid Chemical compound C1CC(OC)CCN1C1=CC=C(Cl)C=C1C(O)=O MNKKPODCJXOTFM-UHFFFAOYSA-N 0.000 description 1
- XINDWSVEMLWQDS-UHFFFAOYSA-N 5-chloro-2-(4-methylpiperazin-1-yl)benzoic acid hydrochloride Chemical compound Cl.ClC=1C=CC(=C(C(=O)O)C1)N1CCN(CC1)C XINDWSVEMLWQDS-UHFFFAOYSA-N 0.000 description 1
- BAZIZDFWLLCYMR-UHFFFAOYSA-N 5-chloro-2-(4-phenylpiperazin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 BAZIZDFWLLCYMR-UHFFFAOYSA-N 0.000 description 1
- OSJSLLRQIYEWKN-UHFFFAOYSA-N 5-chloro-2-(4-phenylpiperidin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 OSJSLLRQIYEWKN-UHFFFAOYSA-N 0.000 description 1
- GVDHMJOGYJTOKB-UHFFFAOYSA-N 5-chloro-2-(diethylamino)benzoic acid Chemical compound CCN(CC)C1=CC=C(Cl)C=C1C(O)=O GVDHMJOGYJTOKB-UHFFFAOYSA-N 0.000 description 1
- FEGTVVZUPVZRMQ-UHFFFAOYSA-N 5-chloro-2-(dipentylamino)benzoic acid Chemical compound CCCCCN(CCCCC)C1=CC=C(Cl)C=C1C(O)=O FEGTVVZUPVZRMQ-UHFFFAOYSA-N 0.000 description 1
- ITNCLVAQRUEBAM-UWVGGRQHSA-N 5-chloro-2-[(3S,5S)-3,5-dimethylpiperidin-1-yl]benzoic acid Chemical compound ClC=1C=CC(=C(C(=O)O)C=1)N1C[C@H](C[C@@H](C1)C)C ITNCLVAQRUEBAM-UWVGGRQHSA-N 0.000 description 1
- KYCKIYAOEGAGTQ-UHFFFAOYSA-N 5-chloro-2-[2-methylpropyl(propyl)amino]benzoic acid Chemical compound CCCN(CC(C)C)C1=CC=C(Cl)C=C1C(O)=O KYCKIYAOEGAGTQ-UHFFFAOYSA-N 0.000 description 1
- REOJABRWMFBZPQ-UHFFFAOYSA-N 5-chloro-2-[4-(4-chlorophenyl)piperazin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCN(C=2C=CC(Cl)=CC=2)CC1 REOJABRWMFBZPQ-UHFFFAOYSA-N 0.000 description 1
- DCDJBUPTNBXDFF-UHFFFAOYSA-N 5-chloro-2-[4-(furan-2-carbonyl)piperazin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1CCN(C(=O)C=2OC=CC=2)CC1 DCDJBUPTNBXDFF-UHFFFAOYSA-N 0.000 description 1
- YPIWHNJUZNQZCD-UHFFFAOYSA-N 5-chloro-2-[cyclohexyl(ethyl)amino]benzoic acid Chemical compound C=1C=C(Cl)C=C(C(O)=O)C=1N(CC)C1CCCCC1 YPIWHNJUZNQZCD-UHFFFAOYSA-N 0.000 description 1
- XRSRSDLVOFVSFT-UHFFFAOYSA-N 5-chloro-2-morpholin-4-ylbenzamide Chemical compound NC(=O)C1=CC(Cl)=CC=C1N1CCOCC1 XRSRSDLVOFVSFT-UHFFFAOYSA-N 0.000 description 1
- YQMKFEMHJPDAEX-UHFFFAOYSA-N 5-chloro-2-piperidin-1-ylbenzohydrazide Chemical compound ClC=1C=CC(=C(C(=O)NN)C=1)N1CCCCC1 YQMKFEMHJPDAEX-UHFFFAOYSA-N 0.000 description 1
- UXORLGHDHUTZCI-UHFFFAOYSA-N 5-chloro-2-pyrrol-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1N1C=CC=C1 UXORLGHDHUTZCI-UHFFFAOYSA-N 0.000 description 1
- MKSHNHIBWOUFDK-UHFFFAOYSA-N 5-cyano-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(C#N)=CC=C1N1CCCCC1 MKSHNHIBWOUFDK-UHFFFAOYSA-N 0.000 description 1
- ZQEWAKSVSODFQG-UHFFFAOYSA-N 5-methoxy-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1N1CCCCC1 ZQEWAKSVSODFQG-UHFFFAOYSA-N 0.000 description 1
- UNEAUOPNMFUVEC-UHFFFAOYSA-N 5-nitro-2-(3,3,5,5-tetramethylpiperidin-1-yl)benzoic acid Chemical compound C1C(C)(C)CC(C)(C)CN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O UNEAUOPNMFUVEC-UHFFFAOYSA-N 0.000 description 1
- PFHJMRRYUIYQTH-UHFFFAOYSA-N 5-nitro-2-(4-phenylpiperazin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 PFHJMRRYUIYQTH-UHFFFAOYSA-N 0.000 description 1
- TUIBWENOIVPIAT-UHFFFAOYSA-N 5-nitro-2-(4-phenylpiperidin-1-yl)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 TUIBWENOIVPIAT-UHFFFAOYSA-N 0.000 description 1
- CHSOARKRVYSVQB-UHFFFAOYSA-N 5-nitro-2-(4-propan-2-ylpiperidin-1-yl)benzoic acid Chemical compound C1CC(C(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1C(O)=O CHSOARKRVYSVQB-UHFFFAOYSA-N 0.000 description 1
- BJFMTEPHRNENIO-UHFFFAOYSA-N 5-nitro-2-piperidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCCCC1 BJFMTEPHRNENIO-UHFFFAOYSA-N 0.000 description 1
- BFGCALKAENBFBV-UHFFFAOYSA-N 5-nitro-2-thiomorpholin-4-ylbenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCSCC1 BFGCALKAENBFBV-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- 101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241001124532 Bubalus depressicornis Species 0.000 description 1
- JAYNVIPOHJITNS-UHFFFAOYSA-N C(C)C1=C(C(=O)OCCN)C=CC=C1 Chemical compound C(C)C1=C(C(=O)OCCN)C=CC=C1 JAYNVIPOHJITNS-UHFFFAOYSA-N 0.000 description 1
- SUPYHMWFAXKORB-UHFFFAOYSA-N CC(C)CN(C1CCCCC1)C2=C(C=CC=C2N)C(=O)O Chemical compound CC(C)CN(C1CCCCC1)C2=C(C=CC=C2N)C(=O)O SUPYHMWFAXKORB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000016936 Dendrocalamus strictus Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- OZLGRUXZXMRXGP-UHFFFAOYSA-N Fluo-3 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)N(CC(O)=O)CC(O)=O)=C1 OZLGRUXZXMRXGP-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000005548 Hexokinase Human genes 0.000 description 1
- 108700040460 Hexokinases Proteins 0.000 description 1
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- GWBWGPRZOYDADH-UHFFFAOYSA-N [C].[Na] Chemical compound [C].[Na] GWBWGPRZOYDADH-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- JFBKNMAATLUBIX-UHFFFAOYSA-N [K+].ClC=1C=CC(=C(C(=O)N[O-])C=1)N1CCCCC1 Chemical compound [K+].ClC=1C=CC(=C(C(=O)N[O-])C=1)N1CCCCC1 JFBKNMAATLUBIX-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical compound C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 description 1
- PVEDXUXKUSBLFK-UHFFFAOYSA-N benzaldehyde;hydrochloride Chemical compound Cl.O=CC1=CC=CC=C1 PVEDXUXKUSBLFK-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KLQNJBAFEFFWQZ-UHFFFAOYSA-N benzoic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)C1=CC=CC=C1 KLQNJBAFEFFWQZ-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- OVHDZBAFUMEXCX-UHFFFAOYSA-N benzyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1 OVHDZBAFUMEXCX-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- LSLWNAOQPPLHSW-UHFFFAOYSA-N butan-2-yl benzoate Chemical compound CCC(C)OC(=O)C1=CC=CC=C1 LSLWNAOQPPLHSW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- KQHLPMCNDYYZMB-UHFFFAOYSA-N chloromethylbenzene;hydrochloride Chemical compound Cl.ClCC1=CC=CC=C1 KQHLPMCNDYYZMB-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 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 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- NEEUQIUQWPULBJ-UHFFFAOYSA-N dipotassium 2-methylpropan-2-olate Chemical compound [K+].[K+].CC(C)(C)[O-].CC(C)(C)[O-] NEEUQIUQWPULBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001729 effect on metabolism Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 125000004050 enoyl group Chemical group 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- OEZNTSMHCAKDNV-UHFFFAOYSA-N ethyl 4-(1-hydrazinylethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(C(C)NN)C=C1 OEZNTSMHCAKDNV-UHFFFAOYSA-N 0.000 description 1
- YFLWCZIVJVCWNQ-UHFFFAOYSA-N ethyl 4-(2-aminoethyl)benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=C(CCN)C=C1 YFLWCZIVJVCWNQ-UHFFFAOYSA-N 0.000 description 1
- ZPUKPAPWEWUPTC-UHFFFAOYSA-N ethyl 4-ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(CC)C=C1 ZPUKPAPWEWUPTC-UHFFFAOYSA-N 0.000 description 1
- VZNLGZNHFOVPJT-UHFFFAOYSA-N ethyl acetate;ethylbenzene Chemical compound CCOC(C)=O.CCC1=CC=CC=C1 VZNLGZNHFOVPJT-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- HGTZHLPSLSVQRY-UHFFFAOYSA-N methyl 2-(1-bromoethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C(C)Br HGTZHLPSLSVQRY-UHFFFAOYSA-N 0.000 description 1
- RHBGWZSBVYGMNY-UHFFFAOYSA-N methyl 4-(2-aminopropyl)benzoate Chemical compound COC(=O)C1=CC=C(CC(C)N)C=C1 RHBGWZSBVYGMNY-UHFFFAOYSA-N 0.000 description 1
- YDEWYJZBFFXSPE-UHFFFAOYSA-N methyl 4-(aminooxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(CON)C=C1 YDEWYJZBFFXSPE-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- XDIWDRFZCSZPTO-UHFFFAOYSA-N n,n-dipropylbenzamide Chemical compound CCCN(CCC)C(=O)C1=CC=CC=C1 XDIWDRFZCSZPTO-UHFFFAOYSA-N 0.000 description 1
- RAFVKOLBEOKYJW-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Cl)=CN=C1C(=O)NC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 RAFVKOLBEOKYJW-SFHVURJKSA-N 0.000 description 1
- BAULSHLTGVOYKM-UHFFFAOYSA-N n-butylbenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1 BAULSHLTGVOYKM-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- INOVPKZAEASFME-UHFFFAOYSA-N n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1 INOVPKZAEASFME-UHFFFAOYSA-N 0.000 description 1
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 1
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-M o-toluate Chemical compound CC1=CC=CC=C1C([O-])=O ZWLPBLYKEWSWPD-UHFFFAOYSA-M 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- ATCNEEZKWDFMMK-UHFFFAOYSA-N potassium 5-chloro-2-(dimethylamino)-N-oxidobenzamide Chemical compound [K+].ClC=1C=CC(=C(C(=O)N[O-])C=1)N(C)C ATCNEEZKWDFMMK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792928352 DE2928352A1 (de) | 1979-07-13 | 1979-07-13 | Neue aminobenzoesaeureamide, ihre herstellung und ihre verwendung als arzneimittel |
| DE19792949259 DE2949259A1 (de) | 1979-07-13 | 1979-12-07 | Neue aminobenzoesaeureamide, ihre herstellung und ihre verwendung als arzneimittel |
| DE19803016651 DE3016651A1 (de) | 1980-04-30 | 1980-04-30 | Neue carbonsaeureamide, deren herstellung und diese sie enthaltende arzneimittel |
| DE19803016650 DE3016650A1 (de) | 1979-07-13 | 1980-04-30 | Neue 2-amino-benzoesaeure-derivate, deren herstellung und deren verwendung als arzneimittel oder zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD153207A5 true DD153207A5 (de) | 1981-12-30 |
Family
ID=27432434
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD222511A DD153207A5 (de) | 1979-07-13 | 1980-07-09 | Verfahren zur herstellung von neuen carbonsaeureamiden |
| DD80231669A DD200152A5 (de) | 1979-07-13 | 1980-07-09 | Verfahren zur herstellung neuer 2-aminobenzoesaeure-derivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80231669A DD200152A5 (de) | 1979-07-13 | 1980-07-09 | Verfahren zur herstellung neuer 2-aminobenzoesaeure-derivate |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0023569B1 (enExample) |
| AU (1) | AU535924B2 (enExample) |
| DD (2) | DD153207A5 (enExample) |
| DE (1) | DE3063878D1 (enExample) |
| DK (1) | DK294180A (enExample) |
| ES (1) | ES493313A0 (enExample) |
| FI (1) | FI802228A7 (enExample) |
| GR (1) | GR69336B (enExample) |
| IE (1) | IE50292B1 (enExample) |
| NO (1) | NO152005C (enExample) |
| NZ (1) | NZ194317A (enExample) |
| PT (1) | PT71551B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100535A1 (de) * | 1981-01-10 | 1982-08-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue carbonsaeure-derivate, ihre herstellung und ihre verwendung als arzneimittel" |
| DE3139970A1 (de) * | 1981-10-08 | 1983-04-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| DE3211934A1 (de) * | 1982-03-31 | 1983-10-13 | Hoechst Ag, 6230 Frankfurt | Salicylsaeurederivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| DE3682136D1 (de) * | 1985-07-31 | 1991-11-28 | Hoechst Ag | N-substituierte 5-nitroanthranilsaeuren, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen. |
| EP0716656A1 (en) * | 1993-09-03 | 1996-06-19 | Smithkline Beecham Plc | Amide derivatives as 5ht1d receptor antagonists |
| US5741926A (en) * | 1997-02-12 | 1998-04-21 | Shaman Pharmaceuticals, Inc. | Aniline derivatives having antihyperglycemic activity |
| BR9914018A (pt) * | 1998-09-22 | 2001-07-03 | Yamanouchi Pharmaceuticals Co | Derivado de cianofenila |
| RU2221785C2 (ru) * | 1998-09-22 | 2004-01-20 | Яманоути Фармасьютикал Ко., Лтд. | Гетероциклическое производное, фармацевтическая композиция, его содержащая, и промежуточный продукт |
| EP1310488A4 (en) * | 2000-08-09 | 2005-08-10 | Mitsubishi Pharma Corp | CONCENTRATED BICYCLIC AMID COMPOUNDS AND THEIR MEDICAL USE |
| CN100471838C (zh) | 2000-12-28 | 2009-03-25 | 第一制药株式会社 | Vla-4抑制剂 |
| US7250518B2 (en) | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| ATE293109T1 (de) * | 2001-01-31 | 2005-04-15 | Pfizer Prod Inc | Nikotinsäureamid-derivate und ihre mimetika als inhibitoren von pde4-isozyms |
| IL161134A0 (en) * | 2002-02-28 | 2004-08-31 | Japan Tobacco Inc | Ester compound and medical use thereof |
| US7601868B2 (en) | 2003-02-12 | 2009-10-13 | Takeda Pharmaceutical Company Limited | Amine derivative |
| CA2528586A1 (en) | 2003-07-24 | 2005-02-03 | Daiichi Pharmaceutical Co., Ltd. | Cyclohexanecarboxylic acid compound |
| US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
| CN107759477A (zh) * | 2017-11-20 | 2018-03-06 | 阿里化学(常州)有限公司 | 一种对硝基苯乙胺盐酸盐的生产制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936467A (en) * | 1968-03-27 | 1976-02-03 | Ciba-Geigy Corporation | Hydroxyalkylenimino-phenyl-acetic acids |
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
| DE2604560A1 (de) * | 1976-02-06 | 1977-08-11 | Boehringer Mannheim Gmbh | Phenylalkancarbonsaeure-derivate und verfahren zu ihrer herstellung |
| DE2655144A1 (de) * | 1976-12-06 | 1978-06-08 | Basf Ag | Substituierte nicotinsaeureamide |
| DE2706977A1 (de) * | 1977-02-18 | 1978-08-24 | Hoechst Ag | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
-
1980
- 1980-06-28 EP EP80103670A patent/EP0023569B1/de not_active Expired
- 1980-06-28 DE DE8080103670T patent/DE3063878D1/de not_active Expired
- 1980-07-08 DK DK294180A patent/DK294180A/da not_active Application Discontinuation
- 1980-07-09 DD DD222511A patent/DD153207A5/de unknown
- 1980-07-09 DD DD80231669A patent/DD200152A5/de unknown
- 1980-07-11 IE IE1453/80A patent/IE50292B1/en unknown
- 1980-07-11 NO NO802087A patent/NO152005C/no unknown
- 1980-07-11 AU AU60362/80A patent/AU535924B2/en not_active Ceased
- 1980-07-11 FI FI802228A patent/FI802228A7/fi not_active Application Discontinuation
- 1980-07-11 NZ NZ194317A patent/NZ194317A/en unknown
- 1980-07-11 ES ES493313A patent/ES493313A0/es active Granted
- 1980-07-12 GR GR62446A patent/GR69336B/el unknown
- 1980-07-14 PT PT71551A patent/PT71551B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT71551B (de) | 1982-01-13 |
| FI802228A7 (fi) | 1981-01-01 |
| IE50292B1 (en) | 1986-03-19 |
| NO152005B (no) | 1985-04-09 |
| DK294180A (da) | 1981-01-14 |
| GR69336B (enExample) | 1982-05-17 |
| ES8107164A1 (es) | 1981-10-01 |
| AU6036280A (en) | 1981-01-15 |
| NZ194317A (en) | 1984-11-09 |
| PT71551A (de) | 1980-08-01 |
| ES493313A0 (es) | 1981-10-01 |
| EP0023569B1 (de) | 1983-06-22 |
| NO802087L (no) | 1981-01-14 |
| DD200152A5 (de) | 1983-03-23 |
| DE3063878D1 (en) | 1983-07-28 |
| EP0023569A1 (de) | 1981-02-11 |
| AU535924B2 (en) | 1984-04-12 |
| IE801453L (en) | 1981-01-13 |
| NO152005C (no) | 1985-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD153207A5 (de) | Verfahren zur herstellung von neuen carbonsaeureamiden | |
| US4595780A (en) | Sulfonamido-benzamide derivatives | |
| DE2940687C2 (enExample) | ||
| DE2700193A1 (de) | Veraetherte hydroxy-benzodiheterocyclen | |
| DE3132882A1 (de) | Neue piperazinone, ihre herstellung und verwendung | |
| EP0058779B1 (de) | Neue Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel | |
| DE2336130A1 (de) | Tricyclische verbindungen | |
| DD202021A5 (de) | Verfahren zur herstellung neuer carbonsaeure-derivate | |
| EP0250361B1 (de) | Disubstituierte Piperazine | |
| EP1233961B9 (de) | Verfahren zur herstellung von 5-(1-piperazinyl)-benzofuran-2-carboxamid durch übergansmetall-katalysierte aminierung | |
| DD149069A5 (de) | Verfahren zur herstellung neuer piperidinopropylerivate | |
| DE2737630C2 (enExample) | ||
| DE3132915A1 (de) | 1,5-diphenylpyrazolin-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| US5059599A (en) | Derivatives of 1-phenyl 1,4-dihydro 3-amino 4-oxo pyridazines, their preparation and their use in therapy | |
| EP0472166A1 (de) | Tricyclische Pyridonderivate | |
| NO138250B (no) | Analogifremgangsmaate for fremstilling av farmakologisk aktive benzylaminer | |
| DE2330124A1 (de) | Anilidderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2725019A1 (de) | Verfahren zur herstellung substituierter aminochinazolinderivate und zwischenprodukte dafuer | |
| US4457875A (en) | Substituted 2,4 dialkoxy benzene sulfonyl chlorides | |
| DE19932314A1 (de) | Benzofuranderivate | |
| HU183178B (en) | Process for preparing new carboxylic acid derivatives | |
| CH518964A (de) | Verfahren zur Herstellung von Benzoxazin-2-onen | |
| DD143910A5 (de) | Verfahren zur herstellung von pyridopyrimidinen | |
| EP0123977A1 (de) | Substituierte Piperazin-1-yl-essigsäure-amide, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| USRE29628E (en) | Aminobenzyl-amines and salts thereof |