IE46497B1 - Meta-sulfonamido-benzamide derivatives - Google Patents
Meta-sulfonamido-benzamide derivativesInfo
- Publication number
- IE46497B1 IE46497B1 IE145/78A IE14578A IE46497B1 IE 46497 B1 IE46497 B1 IE 46497B1 IE 145/78 A IE145/78 A IE 145/78A IE 14578 A IE14578 A IE 14578A IE 46497 B1 IE46497 B1 IE 46497B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- methoxy
- ethyl
- pyrrolidinylmethyl
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 230000003474 anti-emetic effect Effects 0.000 claims abstract description 4
- 125000005237 alkyleneamino group Chemical group 0.000 claims abstract description 3
- 239000002111 antiemetic agent Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- -1 amino, methylamino Chemical group 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 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 claims description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- 238000006277 sulfonation reaction Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000008298 dragée Substances 0.000 claims description 3
- 125000004185 ester group Chemical class 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims description 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims description 2
- SZOLUXDHHKCYKT-ONEGZZNKSA-N (e)-but-1-en-1-amine Chemical compound CC\C=C\N SZOLUXDHHKCYKT-ONEGZZNKSA-N 0.000 claims description 2
- RHTLJPCIBYSWBU-UHFFFAOYSA-N 5-(butylsulfonylamino)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound CCCCS(=O)(=O)NC1=CC=C(OC)C(C(=O)NCC2N(CCC2)CC)=C1 RHTLJPCIBYSWBU-UHFFFAOYSA-N 0.000 claims description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- SCWBHWCAKIVLQO-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(methanesulfonamido)-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=CC=C1OC SCWBHWCAKIVLQO-UHFFFAOYSA-N 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 235000019271 petrolatum Nutrition 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 8
- XQTHGXBCVXTYTG-UHFFFAOYSA-N 3-(methanesulfonamido)benzamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(N)=O)=C1 XQTHGXBCVXTYTG-UHFFFAOYSA-N 0.000 claims 2
- NENGJAOIFFHXBY-UHFFFAOYSA-N 2-(piperidin-1-ylsulfonylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NS(=O)(=O)N1CCCCC1 NENGJAOIFFHXBY-UHFFFAOYSA-N 0.000 claims 1
- BDOIBFRYZCFLBN-UHFFFAOYSA-N 2-(propylsulfonylamino)benzamide Chemical compound CCCS(=O)(=O)NC1=CC=CC=C1C(N)=O BDOIBFRYZCFLBN-UHFFFAOYSA-N 0.000 claims 1
- ZUNMZCCDRLBDHW-UHFFFAOYSA-N 4-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(methanesulfonamido)-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=C(Cl)C=C1OC ZUNMZCCDRLBDHW-UHFFFAOYSA-N 0.000 claims 1
- KMBABEIGJHILNM-UHFFFAOYSA-N 5-(benzenesulfonamido)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(=O)(=O)C=2C=CC=CC=2)=CC=C1OC KMBABEIGJHILNM-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 244000269722 Thea sinensis Species 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- MPYNGMUFNQQQGW-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-4-fluoro-5-(methanesulfonamido)-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=C(F)C=C1OC MPYNGMUFNQQQGW-UHFFFAOYSA-N 0.000 claims 1
- QDSFGMCZCYXYJK-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-[ethylsulfonyl(methyl)amino]-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(N(C)S(=O)(=O)CC)=CC=C1OC QDSFGMCZCYXYJK-UHFFFAOYSA-N 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 230000000506 psychotropic effect Effects 0.000 abstract description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 237
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- 239000013078 crystal Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
- 239000011369 resultant mixture Substances 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 9
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 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 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 4
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
- AWUSVSCKCCFGII-UHFFFAOYSA-N 5-(methanesulfonamido)-2-methoxybenzoic acid Chemical compound COC1=CC=C(NS(C)(=O)=O)C=C1C(O)=O AWUSVSCKCCFGII-UHFFFAOYSA-N 0.000 description 2
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- CDZGCCGQXIIMJK-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(methanesulfonamido)-2,3-dimethoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=CC(OC)=C1OC CDZGCCGQXIIMJK-UHFFFAOYSA-N 0.000 description 1
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- SVIFGEVWHFNGCZ-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-2-(2-oxopyrrolidin-1-yl)acetamide;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCNC(=O)CN1CCCC1=O SVIFGEVWHFNGCZ-UHFFFAOYSA-N 0.000 description 1
- WGBSTIRRHNSMRN-UHFFFAOYSA-N n-tert-butylsulfamoyl chloride Chemical compound CC(C)(C)NS(Cl)(=O)=O WGBSTIRRHNSMRN-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 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 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52008443A JPS5920667B2 (ja) | 1977-01-27 | 1977-01-27 | スルホンアミド系ベンズアミド誘導体 |
| JP52094884A JPS5822110B2 (ja) | 1977-08-08 | 1977-08-08 | ベンズアミド誘導体の合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780145L IE780145L (en) | 1978-07-27 |
| IE46497B1 true IE46497B1 (en) | 1983-06-29 |
Family
ID=26342958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE145/78A IE46497B1 (en) | 1977-01-27 | 1978-01-23 | Meta-sulfonamido-benzamide derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US4351770A (en, 2012) |
| AR (1) | AR225881A1 (en, 2012) |
| AU (1) | AU512057B2 (en, 2012) |
| CA (1) | CA1085411A (en, 2012) |
| CH (1) | CH642945A5 (en, 2012) |
| DE (1) | DE2803651A1 (en, 2012) |
| DK (1) | DK154137C (en, 2012) |
| ES (1) | ES466366A1 (en, 2012) |
| FR (1) | FR2378758A1 (en, 2012) |
| GB (1) | GB1557019A (en, 2012) |
| GR (1) | GR70058B (en, 2012) |
| HU (1) | HU176613B (en, 2012) |
| IE (1) | IE46497B1 (en, 2012) |
| IL (1) | IL53881A (en, 2012) |
| NL (1) | NL7801005A (en, 2012) |
| NZ (1) | NZ186175A (en, 2012) |
| PH (1) | PH12853A (en, 2012) |
| SE (1) | SE426485B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| FR2485526A1 (fr) * | 1980-06-24 | 1981-12-31 | Shionogi & Co | Procede de preparation de derives de n-(diethylaminoethyl)-2 - alcoxybenzamide, nouveaux produits ainsi obtenus et leurs utilisations comme produits pharmaceutiques antiemetiques ou pour guerir les troubles gastriques |
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| PT77219B (fr) * | 1982-08-24 | 1986-02-04 | May & Baker Ltd | Procede de preparation des derives de la benzamide |
| SE8205135D0 (sv) * | 1982-09-09 | 1982-09-09 | Astra Laekemedel Ab | Benzamido-derivatives |
| FR2550447B1 (fr) * | 1983-08-10 | 1986-01-17 | Ile De France | Application du n-(ally-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide comme antiagregant plaquettaire |
| DE3445377A1 (de) * | 1983-12-23 | 1985-07-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen |
| AU567140B2 (en) * | 1984-01-06 | 1987-11-12 | Shionogi & Co., Ltd. | Sulphonamido-benzamide derivatives |
| US4544654A (en) * | 1984-03-20 | 1985-10-01 | Schering A.G. | Substituted sulfonamidobenzamides, antiarrhythmic agents and compositions thereof |
| CA2057324A1 (en) * | 1990-12-18 | 1992-06-19 | Lora Louise Fitch | Benzamide and sulfonamide hypoglycemic agents |
| CA2350903A1 (en) * | 1998-11-20 | 2000-06-02 | F. Hoffmann-La Roche Ag | Pyrrolidine derivatives-ccr-3 receptor antagonists |
| WO2009111279A1 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Pyrazole [3, 4-b] pyridine raf inhibitors |
| US20110003809A1 (en) * | 2008-02-29 | 2011-01-06 | Array Biopharma Inc. | Imidazo [4,5-b] pyridine derivatives used as raf inhibitors |
| WO2009111280A1 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | N- (6-aminopyridin-3-yl) -3- (sulfonamido) benzamide derivatives as b-raf inhibitors for the treatment of cancer |
| JP2011513330A (ja) | 2008-02-29 | 2011-04-28 | アレイ バイオファーマ、インコーポレイテッド | Ｒａｆ阻害化合物およびその使用方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2334186A (en) * | 1938-12-20 | 1943-11-16 | Du Pont | Organic sulphonamides and their preparation |
| GB993584A (en, 2012) * | 1962-01-24 | |||
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| US3210370A (en) * | 1964-06-22 | 1965-10-05 | Upjohn Co | Process for preparing 2, 2'-methylene-bisareneimiazoles |
| FR5916M (en, 2012) * | 1966-01-21 | 1968-05-06 | ||
| FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
| CH547797A (de) * | 1971-08-20 | 1974-04-11 | Fratmann Ag | Verfahren zur herstellung von n - ((1-aethyl-pyrrolidinyl2)-methyl) -2-methoxy-5-sulfamoyl-benzamid. |
| US4021229A (en) * | 1972-09-05 | 1977-05-03 | Stauffer Chemical Company | Sulfonamide herbicide antidote compositions and method of use |
| CH605793A5 (fr) * | 1974-03-05 | 1978-10-13 | Soc Et Scient Et Ind | Procédé de préparation de nouveaux N-(1benzylpyrrollidinil 2-alkyl) benzamides substitués |
| IL46696A (en) * | 1974-03-05 | 1978-07-31 | Soc Et Scient Et Ind | Substituted n-(2-pyrrolidinylalkyl)benzamides, their preparation and pharmaceutical compositions containing them |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
-
1978
- 1978-01-09 NZ NZ186175A patent/NZ186175A/xx unknown
- 1978-01-19 CA CA295,322A patent/CA1085411A/en not_active Expired
- 1978-01-19 GB GB2296/78A patent/GB1557019A/en not_active Expired
- 1978-01-21 GR GR55228A patent/GR70058B/el unknown
- 1978-01-23 IE IE145/78A patent/IE46497B1/en unknown
- 1978-01-24 AU AU32687/78A patent/AU512057B2/en not_active Expired
- 1978-01-24 IL IL53881A patent/IL53881A/xx unknown
- 1978-01-25 DK DK037278A patent/DK154137C/da not_active IP Right Cessation
- 1978-01-26 HU HU78SI1614A patent/HU176613B/hu not_active IP Right Cessation
- 1978-01-26 SE SE7800982A patent/SE426485B/sv not_active IP Right Cessation
- 1978-01-26 FR FR7802210A patent/FR2378758A1/fr active Granted
- 1978-01-26 AR AR270868A patent/AR225881A1/es active
- 1978-01-26 PH PH20712A patent/PH12853A/en unknown
- 1978-01-26 CH CH86678A patent/CH642945A5/de not_active IP Right Cessation
- 1978-01-26 ES ES466366A patent/ES466366A1/es not_active Expired
- 1978-01-27 NL NL7801005A patent/NL7801005A/xx not_active Application Discontinuation
- 1978-01-27 DE DE19782803651 patent/DE2803651A1/de active Granted
- 1978-12-06 US US05/967,011 patent/US4351770A/en not_active Expired - Lifetime
-
1980
- 1980-02-26 US US06/124,728 patent/US4328344A/en not_active Expired - Lifetime
- 1980-02-26 US US06/124,726 patent/US4350635A/en not_active Expired - Lifetime
- 1980-02-26 US US06/124,727 patent/US4328155A/en not_active Expired - Lifetime
- 1980-06-25 US US06/162,793 patent/US4330472A/en not_active Expired - Lifetime
-
1982
- 1982-07-15 US US06/398,702 patent/US4431663A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4328155A (en) | 1982-05-04 |
| SE7800982L (sv) | 1978-07-28 |
| HU176613B (en) | 1981-03-28 |
| DK37278A (da) | 1978-07-28 |
| DK154137C (da) | 1989-04-10 |
| ES466366A1 (es) | 1978-10-01 |
| NZ186175A (en) | 1980-03-05 |
| IL53881A (en) | 1981-05-20 |
| US4330472A (en) | 1982-05-18 |
| PH12853A (en) | 1979-09-12 |
| AU512057B2 (en) | 1980-09-18 |
| DK154137B (da) | 1988-10-17 |
| FR2378758A1 (fr) | 1978-08-25 |
| FR2378758B1 (en, 2012) | 1981-02-06 |
| GR70058B (en, 2012) | 1982-07-26 |
| IL53881A0 (en) | 1978-04-30 |
| SE426485B (sv) | 1983-01-24 |
| CH642945A5 (de) | 1984-05-15 |
| IE780145L (en) | 1978-07-27 |
| GB1557019A (en) | 1979-12-05 |
| US4351770A (en) | 1982-09-28 |
| DE2803651A1 (de) | 1978-08-03 |
| US4328344A (en) | 1982-05-04 |
| AU3268778A (en) | 1979-08-02 |
| DE2803651C2 (en, 2012) | 1988-10-20 |
| US4431663A (en) | 1984-02-14 |
| NL7801005A (nl) | 1978-07-31 |
| AR225881A1 (es) | 1982-05-14 |
| CA1085411A (en) | 1980-09-09 |
| US4350635A (en) | 1982-09-21 |
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