NO744383L - - Google Patents
Info
- Publication number
- NO744383L NO744383L NO744383A NO744383A NO744383L NO 744383 L NO744383 L NO 744383L NO 744383 A NO744383 A NO 744383A NO 744383 A NO744383 A NO 744383A NO 744383 L NO744383 L NO 744383L
- Authority
- NO
- Norway
- Prior art keywords
- sulfonamide
- carbon atoms
- group
- alkyl
- carbamoyl
- Prior art date
Links
- -1 pyrrolidino, morpholino, thiomorpholino Chemical group 0.000 claims description 137
- 238000000034 method Methods 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 71
- 229940124530 sulfonamide Drugs 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 24
- 150000003456 sulfonamides Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 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 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000000460 chlorine Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 230000017858 demethylation Effects 0.000 claims description 4
- 238000010520 demethylation reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- DGHIJQRWXSDFSY-UHFFFAOYSA-N 2-phenylethenylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)C=CC1=CC=CC=C1 DGHIJQRWXSDFSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- 239000000047 product Substances 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 21
- 239000003921 oil Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- SHPHBMZZXHFXDF-VOTSOKGWSA-N (E)-2-phenylethenesulfonamide Chemical class NS(=O)(=O)\C=C\C1=CC=CC=C1 SHPHBMZZXHFXDF-VOTSOKGWSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 238000007792 addition Methods 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- VFLCWXLJSMFEJA-UHFFFAOYSA-N 1-phenylprop-1-ene-2-sulfonamide Chemical compound NS(=O)(=O)C(C)=CC1=CC=CC=C1 VFLCWXLJSMFEJA-UHFFFAOYSA-N 0.000 description 10
- MSCJCFQSOXCHQK-UHFFFAOYSA-N 2-phenylprop-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(C)C1=CC=CC=C1 MSCJCFQSOXCHQK-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- IPTLVHRSGNZLKY-UHFFFAOYSA-N 1,1-diphenyl-3-(2-phenylethenylsulfonyl)urea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)NS(=O)(=O)C=CC1=CC=CC=C1 IPTLVHRSGNZLKY-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QIGLJVBIRIXQRN-UHFFFAOYSA-N DL-leucine ethyl ester Natural products CCOC(=O)C(N)CC(C)C QIGLJVBIRIXQRN-UHFFFAOYSA-N 0.000 description 8
- 239000003524 antilipemic agent Substances 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- YMINPTCNVFONOC-UHFFFAOYSA-N 1-phenylbut-1-ene-2-sulfonamide Chemical compound CCC(S(N)(=O)=O)=CC1=CC=CC=C1 YMINPTCNVFONOC-UHFFFAOYSA-N 0.000 description 7
- BFEQPJYRUMTPAD-UHFFFAOYSA-N 2-(4-chlorophenyl)prop-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(C)C1=CC=C(Cl)C=C1 BFEQPJYRUMTPAD-UHFFFAOYSA-N 0.000 description 7
- YILJJUSYDNSUIB-UHFFFAOYSA-N 3-phenylbut-2-ene-2-sulfonamide Chemical compound NS(=O)(=O)C(C)=C(C)C1=CC=CC=C1 YILJJUSYDNSUIB-UHFFFAOYSA-N 0.000 description 7
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- RVDSGCWRJLORQO-UHFFFAOYSA-N n-(2-phenylethenylsulfonyl)-4-(3-phenylpropyl)piperidine-1-carboxamide Chemical compound C1CC(CCCC=2C=CC=CC=2)CCN1C(=O)NS(=O)(=O)C=CC1=CC=CC=C1 RVDSGCWRJLORQO-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 230000000055 hyoplipidemic effect Effects 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- MFXWPUDWZIDKDM-UHFFFAOYSA-N 1-(4-chlorophenyl)prop-1-ene-2-sulfonamide Chemical compound NS(=O)(=O)C(C)=CC1=CC=C(Cl)C=C1 MFXWPUDWZIDKDM-UHFFFAOYSA-N 0.000 description 5
- NBBQENMZTBDHPJ-UHFFFAOYSA-N 2,2-diphenylethenesulfonamide Chemical compound C=1C=CC=CC=1C(=CS(=O)(=O)N)C1=CC=CC=C1 NBBQENMZTBDHPJ-UHFFFAOYSA-N 0.000 description 5
- WDNJYXIESUMYHL-UHFFFAOYSA-N 2-(4-chlorophenyl)ethenesulfonamide Chemical compound NS(=O)(=O)C=CC1=CC=C(Cl)C=C1 WDNJYXIESUMYHL-UHFFFAOYSA-N 0.000 description 5
- BENVYXWHQGCLRQ-UHFFFAOYSA-N 2-phenylbut-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(CC)C1=CC=CC=C1 BENVYXWHQGCLRQ-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- DWKPPFQULDPWHX-UHFFFAOYSA-N methyl 2-aminopropanoate Chemical compound COC(=O)C(C)N DWKPPFQULDPWHX-UHFFFAOYSA-N 0.000 description 5
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- SSOBTDMVHPEHCW-UHFFFAOYSA-N 1,1-diphenyl-3-(1-phenylprop-1-en-2-ylsulfonyl)urea Chemical group C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)NS(=O)(=O)C(C)=CC1=CC=CC=C1 SSOBTDMVHPEHCW-UHFFFAOYSA-N 0.000 description 4
- VNYMFXKSEFIOMS-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)prop-1-ene-1-sulfonamide Chemical compound CC(C)C1=CC=C(C(C)=CS(N)(=O)=O)C=C1 VNYMFXKSEFIOMS-UHFFFAOYSA-N 0.000 description 4
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- HASRFXGIJALRRB-UHFFFAOYSA-N 4-(3-phenylpropyl)piperidine Chemical compound C=1C=CC=CC=1CCCC1CCNCC1 HASRFXGIJALRRB-UHFFFAOYSA-N 0.000 description 4
- HUNNGCWEUBGJLB-UHFFFAOYSA-N 4-(3-phenylpropyl)piperidine-1-carbonyl chloride Chemical compound C1CN(C(=O)Cl)CCC1CCCC1=CC=CC=C1 HUNNGCWEUBGJLB-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 4
- FCDSNHMTBAYTFE-UHFFFAOYSA-N n-(4-chlorophenyl)-n-phenylcarbamoyl chloride Chemical compound C=1C=C(Cl)C=CC=1N(C(=O)Cl)C1=CC=CC=C1 FCDSNHMTBAYTFE-UHFFFAOYSA-N 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KOYFODYQNAZAAL-UHFFFAOYSA-N 1-(3-chlorophenyl)prop-1-ene-2-sulfonamide Chemical compound NS(=O)(=O)C(C)=CC1=CC=CC(Cl)=C1 KOYFODYQNAZAAL-UHFFFAOYSA-N 0.000 description 3
- RCZMKWIGGCRRLC-UHFFFAOYSA-N 1-(4-fluorophenyl)prop-1-ene-2-sulfonamide Chemical compound NS(=O)(=O)C(C)=CC1=CC=C(F)C=C1 RCZMKWIGGCRRLC-UHFFFAOYSA-N 0.000 description 3
- LKIHLZCCUSLXAD-UHFFFAOYSA-N 2-(2-chlorophenyl)ethenesulfonamide Chemical compound NS(=O)(=O)C=CC1=CC=CC=C1Cl LKIHLZCCUSLXAD-UHFFFAOYSA-N 0.000 description 3
- OOXMOTZJENLQJW-UHFFFAOYSA-N 2-(3-chlorophenyl)ethenesulfonamide Chemical compound NS(=O)(=O)C=CC1=CC=CC(Cl)=C1 OOXMOTZJENLQJW-UHFFFAOYSA-N 0.000 description 3
- BDEWDPDNNMZLBQ-UHFFFAOYSA-N 2-(3-methoxyphenyl)prop-1-ene-1-sulfonamide Chemical compound COC1=CC=CC(C(C)=CS(N)(=O)=O)=C1 BDEWDPDNNMZLBQ-UHFFFAOYSA-N 0.000 description 3
- SKCUJEIMNMTRGU-UHFFFAOYSA-N 2-(3-methylphenyl)ethenesulfonamide Chemical compound CC1=CC=CC(C=CS(N)(=O)=O)=C1 SKCUJEIMNMTRGU-UHFFFAOYSA-N 0.000 description 3
- YIJOMEXPMNOZSY-UHFFFAOYSA-N 2-(4-chlorophenyl)but-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(CC)C1=CC=C(Cl)C=C1 YIJOMEXPMNOZSY-UHFFFAOYSA-N 0.000 description 3
- XWAXPWHHNCQWRK-UHFFFAOYSA-N 2-(4-fluorophenyl)prop-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(C)C1=CC=C(F)C=C1 XWAXPWHHNCQWRK-UHFFFAOYSA-N 0.000 description 3
- CQBVWPSJNUYXGA-UHFFFAOYSA-N 2-(4-methylphenyl)prop-1-ene-1-sulfonamide Chemical compound NS(=O)(=O)C=C(C)C1=CC=C(C)C=C1 CQBVWPSJNUYXGA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WGVPSALPIAOFFL-UHFFFAOYSA-N 4-[3-(4-methoxyphenyl)propyl]piperidine Chemical compound C1=CC(OC)=CC=C1CCCC1CCNCC1 WGVPSALPIAOFFL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 3
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- GOPSLMQZYNTBQY-UHFFFAOYSA-N n-[1-(4-chlorophenyl)prop-1-en-2-ylsulfonyl]-2-ethylpiperidine-1-carboxamide Chemical compound CCC1CCCCN1C(=O)NS(=O)(=O)C(C)=CC1=CC=C(Cl)C=C1 GOPSLMQZYNTBQY-UHFFFAOYSA-N 0.000 description 1
- RYEIZHZPCDCIQT-UHFFFAOYSA-N n-[1-(4-propan-2-ylphenyl)prop-1-enylsulfonyl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NS(=O)(=O)C(=CC)C1=CC=C(C(C)C)C=C1 RYEIZHZPCDCIQT-UHFFFAOYSA-N 0.000 description 1
- SNURNIPRIAUKLQ-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethenylsulfonyl]-4-(3-phenylpropyl)piperidine-1-carboxamide Chemical compound FC1=CC=CC=C1C=CS(=O)(=O)NC(=O)N1CCC(CCCC=2C=CC=CC=2)CC1 SNURNIPRIAUKLQ-UHFFFAOYSA-N 0.000 description 1
- ALIDAXOSOYKCFE-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethenylsulfonyl]thiomorpholine-4-carboxamide Chemical compound C1=CC(Br)=CC=C1C=CS(=O)(=O)NC(=O)N1CCSCC1 ALIDAXOSOYKCFE-UHFFFAOYSA-N 0.000 description 1
- BTIAQCCHVWGZML-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethenylsulfonyl]-4-(2-phenylbutyl)piperidine-1-carboxamide Chemical compound C=1C=CC=CC=1C(CC)CC(CC1)CCN1C(=O)NS(=O)(=O)C=CC1=CC=C(Cl)C=C1 BTIAQCCHVWGZML-UHFFFAOYSA-N 0.000 description 1
- MJEYSTLJOSIXEK-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethenylsulfonyl]-4-(2-phenylethyl)piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C=CS(=O)(=O)NC(=O)N1CCC(CCC=2C=CC=CC=2)CC1 MJEYSTLJOSIXEK-UHFFFAOYSA-N 0.000 description 1
- UMVJIOWQCVDZLW-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethenylsulfonyl]-4-[2-(4-propan-2-yloxyphenyl)ethyl]piperidine-1-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1CCC1CCN(C(=O)NS(=O)(=O)C=CC=2C=CC(Cl)=CC=2)CC1 UMVJIOWQCVDZLW-UHFFFAOYSA-N 0.000 description 1
- LWFDLXWXVWUYKR-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethenylsulfonyl]-4-phenylpiperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C=CS(=O)(=O)NC(=O)N1CCC(C=2C=CC=CC=2)CC1 LWFDLXWXVWUYKR-UHFFFAOYSA-N 0.000 description 1
- ZKRJYEQUSAFPRQ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)prop-1-enylsulfonyl]morpholine-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)=CS(=O)(=O)NC(=O)N1CCOCC1 ZKRJYEQUSAFPRQ-UHFFFAOYSA-N 0.000 description 1
- XCNMACKSURDLKO-UHFFFAOYSA-N n-[2-(4-ethylphenyl)ethenylsulfonyl]-4-methoxypiperidine-1-carboxamide Chemical compound C1=CC(CC)=CC=C1C=CS(=O)(=O)NC(=O)N1CCC(OC)CC1 XCNMACKSURDLKO-UHFFFAOYSA-N 0.000 description 1
- GKOJSRVVQKAZPF-UHFFFAOYSA-N n-[2-(4-fluorophenyl)prop-1-enylsulfonyl]thiomorpholine-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C(C)=CS(=O)(=O)NC(=O)N1CCSCC1 GKOJSRVVQKAZPF-UHFFFAOYSA-N 0.000 description 1
- GIHUMTDTMYPLES-UHFFFAOYSA-N n-[2-(4-methylphenyl)but-1-enylsulfonyl]-4-phenylpiperidine-1-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC)=CS(=O)(=O)NC(=O)N(CC1)CCC1C1=CC=CC=C1 GIHUMTDTMYPLES-UHFFFAOYSA-N 0.000 description 1
- DAQHQRBQDKFSLM-UHFFFAOYSA-N n-[2-(4-propan-2-yloxyphenyl)ethenylsulfonyl]piperidine-1-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1C=CS(=O)(=O)NC(=O)N1CCCCC1 DAQHQRBQDKFSLM-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KVNPRHJSNCFLEG-UHFFFAOYSA-N n-benzyl-n-phenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)CC1=CC=CC=C1 KVNPRHJSNCFLEG-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- NLRLKWCPACLGLM-UHFFFAOYSA-N n-butyl-n-(4-methylphenyl)carbamoyl chloride Chemical compound CCCCN(C(Cl)=O)C1=CC=C(C)C=C1 NLRLKWCPACLGLM-UHFFFAOYSA-N 0.000 description 1
- DCMHYBSUEDRYQF-UHFFFAOYSA-N n-decyl-n-(4-ethylphenyl)carbamoyl chloride Chemical compound CCCCCCCCCCN(C(Cl)=O)C1=CC=C(CC)C=C1 DCMHYBSUEDRYQF-UHFFFAOYSA-N 0.000 description 1
- CXWUMYWMRZEWPV-UHFFFAOYSA-N n-ethyl-n-(4-nitrophenyl)carbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=C([N+]([O-])=O)C=C1 CXWUMYWMRZEWPV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- YKRLMZKCVQTOAZ-UHFFFAOYSA-N prop-1-ene-1-sulfonamide Chemical compound CC=CS(N)(=O)=O YKRLMZKCVQTOAZ-UHFFFAOYSA-N 0.000 description 1
- JHHIBGYNKSWPMJ-UHFFFAOYSA-N prop-1-ene-2-sulfonamide Chemical compound CC(=C)S(N)(=O)=O JHHIBGYNKSWPMJ-UHFFFAOYSA-N 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- 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
- C07D211/16—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 acylated 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
- C07D211/08—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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen 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
- C07D211/06—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
- C07D211/38—Halogen atoms or nitro radicals
-
- 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
-
- 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
- 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
- C07D217/06—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 the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged 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)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42208873A | 1973-12-05 | 1973-12-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO744383L true NO744383L (fr) | 1975-06-30 |
Family
ID=23673328
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO744383A NO744383L (fr) | 1973-12-05 | 1974-12-04 |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS50111046A (fr) |
AR (2) | AR208187A1 (fr) |
AU (1) | AU7575774A (fr) |
BE (1) | BE822874A (fr) |
CA (1) | CA1042909A (fr) |
DD (1) | DD115491A5 (fr) |
DE (1) | DE2456947A1 (fr) |
DK (1) | DK144270C (fr) |
ES (1) | ES432573A1 (fr) |
FI (1) | FI351574A (fr) |
FR (1) | FR2253513B1 (fr) |
GB (1) | GB1473200A (fr) |
IE (1) | IE40430B1 (fr) |
IL (1) | IL46116A0 (fr) |
LU (1) | LU71425A1 (fr) |
NL (1) | NL7415796A (fr) |
NO (1) | NO744383L (fr) |
ZA (1) | ZA747728B (fr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3330603A1 (de) * | 1983-08-25 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Neue 2-amino-alkenylsulfonylharnstoffe |
US5216026A (en) * | 1990-07-17 | 1993-06-01 | Eli Lilly And Company | Antitumor compositions and methods of treatment |
WO2002076404A2 (fr) | 2001-03-23 | 2002-10-03 | Protarga, Inc. | Conjugues d'agents pharmaceutiques et d'alcools gras |
AU2002303164A1 (en) | 2001-03-23 | 2002-10-08 | Protarga, Inc. | Fatty amine drug conjugates |
WO2019043610A1 (fr) * | 2017-08-31 | 2019-03-07 | Cadila Healthcare Limited | Nouveaux dérivés de sulfonylurées substitués |
MX2021008426A (es) * | 2019-01-14 | 2021-09-23 | Cadila Healthcare Ltd | Nuevos derivados de sulfonilurea sustituida. |
-
1974
- 1974-01-01 AR AR256789A patent/AR208187A1/es active
- 1974-11-25 IL IL46116A patent/IL46116A0/xx unknown
- 1974-11-26 AU AU75757/74A patent/AU7575774A/en not_active Expired
- 1974-12-02 DE DE19742456947 patent/DE2456947A1/de not_active Withdrawn
- 1974-12-03 BE BE151087A patent/BE822874A/fr unknown
- 1974-12-04 FI FI3515/74A patent/FI351574A/fi unknown
- 1974-12-04 ES ES432573A patent/ES432573A1/es not_active Expired
- 1974-12-04 NO NO744383A patent/NO744383L/no unknown
- 1974-12-04 NL NL7415796A patent/NL7415796A/xx not_active Application Discontinuation
- 1974-12-04 CA CA215,239A patent/CA1042909A/fr not_active Expired
- 1974-12-04 LU LU71425A patent/LU71425A1/xx unknown
- 1974-12-04 ZA ZA00747728A patent/ZA747728B/xx unknown
- 1974-12-04 DK DK629974A patent/DK144270C/da not_active IP Right Cessation
- 1974-12-04 DD DD182788A patent/DD115491A5/xx unknown
- 1974-12-05 GB GB5275174A patent/GB1473200A/en not_active Expired
- 1974-12-05 IE IE2515/74A patent/IE40430B1/xx unknown
- 1974-12-05 JP JP49140047A patent/JPS50111046A/ja active Pending
- 1974-12-05 FR FR7439786A patent/FR2253513B1/fr not_active Expired
-
1975
- 1975-10-23 AR AR260897A patent/AR211918A1/es active
Also Published As
Publication number | Publication date |
---|---|
ZA747728B (en) | 1976-02-25 |
DK144270C (da) | 1982-07-12 |
ES432573A1 (es) | 1976-11-01 |
NL7415796A (nl) | 1975-06-09 |
IE40430B1 (en) | 1979-05-23 |
FI351574A (fr) | 1975-06-06 |
GB1473200A (en) | 1977-05-11 |
AR208187A1 (es) | 1976-12-09 |
FR2253513B1 (fr) | 1978-07-28 |
JPS50111046A (fr) | 1975-09-01 |
CA1042909A (fr) | 1978-11-21 |
DK629974A (fr) | 1975-07-21 |
DD115491A5 (fr) | 1975-10-05 |
IL46116A0 (en) | 1975-02-10 |
AU7575774A (en) | 1976-05-27 |
DK144270B (da) | 1982-02-01 |
DE2456947A1 (de) | 1975-06-12 |
FR2253513A1 (fr) | 1975-07-04 |
IE40430L (en) | 1975-06-05 |
LU71425A1 (fr) | 1975-08-20 |
BE822874A (fr) | 1975-06-03 |
AR211918A1 (es) | 1978-04-14 |
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