JPS5920667B2 - スルホンアミド系ベンズアミド誘導体 - Google Patents

スルホンアミド系ベンズアミド誘導体

Info

Publication number: JPS5920667B2
Authority: JP; Japan
Prior art keywords: group; methylene chloride; alkyl group; residue; formula
Prior art date: 1977-01-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP52008443A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5392763A (en

Inventor

秀尾形

博松本

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shionogi and Co Ltd

Original Assignee

Shionogi and Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-01-27

Filing date

1977-01-27

Publication date

1984-05-15

1977-01-27 Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd

1977-01-27 Priority to JP52008443A priority Critical patent/JPS5920667B2/ja

1978-01-06 Priority to ZA00780096A priority patent/ZA7896B/xx

1978-01-09 Priority to NZ186175A priority patent/NZ186175A/xx

1978-01-19 Priority to GB2296/78A priority patent/GB1557019A/en

1978-01-19 Priority to CA295,322A priority patent/CA1085411A/fr

1978-01-21 Priority to GR55228A priority patent/GR70058B/el

1978-01-23 Priority to IE145/78A priority patent/IE46497B1/en

1978-01-24 Priority to AU32687/78A priority patent/AU512057B2/en

1978-01-24 Priority to IL53881A priority patent/IL53881A/xx

1978-01-25 Priority to BE184636A priority patent/BE863313A/fr

1978-01-25 Priority to DK037278A priority patent/DK154137C/da

1978-01-26 Priority to FR7802210A priority patent/FR2378758A1/fr

1978-01-26 Priority to PH20712A priority patent/PH12853A/en

1978-01-26 Priority to AR270868A priority patent/AR225881A1/es

1978-01-26 Priority to HU78SI1614A priority patent/HU176613B/hu

1978-01-26 Priority to ES466366A priority patent/ES466366A1/es

1978-01-26 Priority to CH86678A priority patent/CH642945A5/de

1978-01-26 Priority to SE7800982A priority patent/SE426485B/sv

1978-01-27 Priority to NL7801005A priority patent/NL7801005A/xx

1978-01-27 Priority to DE19782803651 priority patent/DE2803651A1/de

1978-08-15 Publication of JPS5392763A publication Critical patent/JPS5392763A/ja

1978-12-06 Priority to US05/967,011 priority patent/US4351770A/en

1980-02-26 Priority to US06/124,727 priority patent/US4328155A/en

1980-02-26 Priority to US06/124,726 priority patent/US4350635A/en

1980-02-26 Priority to US06/124,728 priority patent/US4328344A/en

1980-06-25 Priority to US06/162,793 priority patent/US4330472A/en

1982-07-15 Priority to US06/398,702 priority patent/US4431663A/en

1984-05-15 Publication of JPS5920667B2 publication Critical patent/JPS5920667B2/ja

Status Expired legal-status Critical Current

Links

229940124530 sulfonamide Drugs 0.000 title claims description 6
-1 Sulfonamide benzamide derivatives Chemical class 0.000 title description 29
238000006243 chemical reaction Methods 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000004663 dialkyl amino group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000003456 sulfonamides Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000003936 benzamides Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 161
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000013078 crystal Substances 0.000 description 19
239000012044 organic layer Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
235000002639 sodium chloride Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
238000001816 cooling Methods 0.000 description 9
239000010446 mirabilite Substances 0.000 description 9
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 9
239000002253 acid Substances 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000013076 target substance Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
150000001559 benzoic acids Chemical class 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002994 raw material Substances 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
238000004587 chromatography analysis Methods 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
150000002148 esters Chemical group 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
GINFTDKGOGCWPV-UHFFFAOYSA-B C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+] Chemical compound C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.C([O-])([O-])=O.[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+] GINFTDKGOGCWPV-UHFFFAOYSA-B 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
208000007107 Stomach Ulcer Diseases 0.000 description 2
229940054066 benzamide antipsychotics Drugs 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
201000005917 gastric ulcer Diseases 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
PSCXCIPPRCFAAO-UHFFFAOYSA-N methyl 5-amino-2-methoxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1OC PSCXCIPPRCFAAO-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000004089 psychotropic agent Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
RSBXOVZBSUWTCT-UHFFFAOYSA-N 4-chloro-2-methoxy-5-nitrobenzoic acid Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1C(O)=O RSBXOVZBSUWTCT-UHFFFAOYSA-N 0.000 description 1
HJVZGDWNFVNJAU-UHFFFAOYSA-N 5-(cyanoamino)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NC#N)=CC=C1OC HJVZGDWNFVNJAU-UHFFFAOYSA-N 0.000 description 1
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 1
JMOGARYRWMUPAE-UHFFFAOYSA-N 5-amino-2-methoxybenzamide Chemical compound COC1=CC=C(N)C=C1C(N)=O JMOGARYRWMUPAE-UHFFFAOYSA-N 0.000 description 1
FKLZXOIYBRAZIN-UHFFFAOYSA-N 5-amino-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(N)=CC=C1OC FKLZXOIYBRAZIN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
NONAZVNDDFGZJX-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N.CS(=O)(=O)N Chemical compound C(C1=CC=CC=C1)(=O)N.CS(=O)(=O)N NONAZVNDDFGZJX-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
244000189548 Chrysanthemum x morifolium Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
239000000164 antipsychotic agent Substances 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
239000002775 capsule Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
CCJXQRNXZKSOGJ-UHFFFAOYSA-N ethylsulfonyl ethanesulfonate Chemical compound CCS(=O)(=O)OS(=O)(=O)CC CCJXQRNXZKSOGJ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
PDSIOMKEYNZXLS-UHFFFAOYSA-H hexapotassium hexahydroxide Chemical compound [OH-].[K+].[K+].[K+].[K+].[K+].[K+].[OH-].[OH-].[OH-].[OH-].[OH-] PDSIOMKEYNZXLS-UHFFFAOYSA-H 0.000 description 1
UUCAYCOVAYXMLX-UHFFFAOYSA-H hexasodium hydrogen carbonate Chemical compound C([O-])(O)=O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].C([O-])(O)=O.C([O-])(O)=O.C([O-])(O)=O.C([O-])(O)=O.C([O-])(O)=O UUCAYCOVAYXMLX-UHFFFAOYSA-H 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
YSOOKVHJDSPPBE-UHFFFAOYSA-N methyl 5-(methanesulfonamido)-2-methoxybenzoate Chemical compound COC(=O)C1=CC(NS(C)(=O)=O)=CC=C1OC YSOOKVHJDSPPBE-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000008267 milk Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
ZFGPIYSLIZRQJN-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-(tetrazol-1-yl)benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(N2N=NN=C2)=CC=C1OC ZFGPIYSLIZRQJN-UHFFFAOYSA-N 0.000 description 1
DVRHYBYPKBFJKY-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-nitrobenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC([N+]([O-])=O)=CC=C1OC DVRHYBYPKBFJKY-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 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
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP52008443A 1977-01-27 1977-01-27 スルホンアミド系ベンズアミド誘導体 Expired JPS5920667B2 (ja)

Priority Applications (26)

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
ZA00780096A ZA7896B (en)	1977-01-27	1978-01-06	Meta-sulfonamido-benzamine derivatives
NZ186175A NZ186175A (en)	1977-01-27	1978-01-09	Meta-sulphonamidobenzamide derivatives
GB2296/78A GB1557019A (en)	1977-01-27	1978-01-19	Metalsulphonamido-benzamide derivatives
CA295,322A CA1085411A (fr)	1977-01-27	1978-01-19	Derives de la meta-sulfonamido-benzamide
GR55228A GR70058B (fr)	1977-01-27	1978-01-21
IE145/78A IE46497B1 (en)	1977-01-27	1978-01-23	Meta-sulfonamido-benzamide derivatives
AU32687/78A AU512057B2 (en)	1977-01-27	1978-01-24	Meta-sulfonamido-benzamide derivatives
IL53881A IL53881A (en)	1977-01-27	1978-01-24	Meta-sulfonamido-benzamide derivatives,processes for the production thereof and pharmaceutical or veterinary compositions containing the same
BE184636A BE863313A (fr)	1977-01-27	1978-01-25	M-sulfonamidobenzamides
DK037278A DK154137C (da)	1977-01-27	1978-01-25	Analogifremgangsmaade til fremstilling af meta-sulfonamido-benzamidderivater
PH20712A PH12853A (en)	1977-01-27	1978-01-26	Meta-sulfonamido-benzamide derivatives
SE7800982A SE426485B (sv)	1977-01-27	1978-01-26	Forfarande att framstella meta-sulfonamido-bensamid-derivat innehallande en pyrrolidinrest
FR7802210A FR2378758A1 (fr)	1977-01-27	1978-01-26	Derives de meta-sulfanomidobenzamide et nouveaux produits ainsi obtenus, a activite notamment antiemetique et psychotrope
AR270868A AR225881A1 (es)	1977-01-27	1978-01-26	Procedimiento para obtener derivados de n-(2-pirrolidinil-metil)-5-sulfonamida-benzamina y sus cales
HU78SI1614A HU176613B (en)	1977-01-27	1978-01-26	Process for preparing meta-sulphonamido-benzamide derivatives
ES466366A ES466366A1 (es)	1977-01-27	1978-01-26	Un procedimiento para preparar derivados de metasulfonamido-benzamida.
CH86678A CH642945A5 (de)	1977-01-27	1978-01-26	Meta-sulfonamido-benzamid derivate und verfahren zu ihrer herstellung.
NL7801005A NL7801005A (nl)	1977-01-27	1978-01-27	Derivaten van meta-sulfonamido-benzamide.
DE19782803651 DE2803651A1 (de)	1977-01-27	1978-01-27	M-sulfonamidobenzamid-derivate
US05/967,011 US4351770A (en)	1977-01-27	1978-12-06	Preparation of N(2-pyrrolidinylmethyl)2-methoxy-5-benzenesulfonamidobenzamides
US06/124,728 US4328344A (en)	1977-01-27	1980-02-26	Meta-amino sulfonamido-benzamides
US06/124,727 US4328155A (en)	1977-01-27	1980-02-26	Meta-sulfonamido-benzamides
US06/124,726 US4350635A (en)	1977-01-27	1980-02-26	N(2-Pyrrolidinylmethyl)meta-sulfonamido-benzamides
US06/162,793 US4330472A (en)	1977-01-27	1980-06-25	Meta-sulfonamido-benzamide derivatives
US06/398,702 US4431663A (en)	1977-01-27	1982-07-15	Treatment of psychosis with meta-sulfonamido-benzamide derivatives

Applications Claiming Priority (1)

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

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP22173483A Division JPS6017769B2 (ja)	1983-11-24	1983-11-24	メタ−（スルホンアミド）ベンズアミド系向精神薬

Publications (2)

Publication Number	Publication Date
JPS5392763A JPS5392763A (en)	1978-08-15
JPS5920667B2 true JPS5920667B2 (ja)	1984-05-15

Family

ID=11693258

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52008443A Expired 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

Country Status (3)

Country	Link
JP (1)	JPS5920667B2 (fr)
BE (1)	BE863313A (fr)
ZA (1)	ZA7896B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61265891A (ja) *	1985-05-20	1986-11-25	松下電工株式会社	配線具

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0320630A1 (fr) *	1987-11-19	1989-06-21	The Vanderbilt University	Iodobenzamides énantiomeriques

1977
- 1977-01-27 JP JP52008443A patent/JPS5920667B2/ja not_active Expired
1978
- 1978-01-06 ZA ZA00780096A patent/ZA7896B/xx unknown
- 1978-01-25 BE BE184636A patent/BE863313A/fr not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61265891A (ja) *	1985-05-20	1986-11-25	松下電工株式会社	配線具

Also Published As

Publication number	Publication date
BE863313A (fr)	1978-05-16
ZA7896B (en)	1978-10-25
JPS5392763A (en)	1978-08-15

Publication	Publication Date	Title
KR100915481B1 (ko)	2009-09-03	아미노퀴나졸린 화합물
EP0442820B1 (fr)	1995-09-13	Nouveaux dérivés de benzimidazole et d'azabenzimidazole, antagonistes des récepteurs au thromboxane; leurs procédés de préparation, intermédiaires de synthèse, compositions les contenant
JPH06507182A (ja)	1994-08-11	Ｎ−スルホニル−２−オキソインドール誘導体、それらの製造、及びそれらが存在する薬学的組成物
CZ178092A3 (en)	1993-01-13	Amidine compounds and process for preparing thereof
IE45574B1 (en)	1982-10-06	Piperidyl-indole derivatives, processes for preparing them and pharmaceutical compositions containing them
PL166392B1 (pl)	1995-05-31	Sposób wytwarzania nowych pochodnych fenyloacetamidowych PL PL PL PL
JPH0314315B2 (fr)	1991-02-26
US4431663A (en)	1984-02-14	Treatment of psychosis with meta-sulfonamido-benzamide derivatives
US4857644A (en)	1989-08-15	Aryl sulfonopiperazines as anti-inflammatory agents
MC1231A1 (fr)	1979-10-26	Nouveaux benzamides heterocycliques substitues,leurs procedes de preparation et leur application comme modificateurs du comportement
JPS5916871A (ja)	1984-01-28	スルホンアミド系ベンズアミド類
JPS5920667B2 (ja)	1984-05-15	スルホンアミド系ベンズアミド誘導体
JP2003532616A (ja)	2003-11-05	骨粗鬆症の治療に有用なａ．ｏ．インドール誘導体
US4018773A (en)	1977-04-19	Phenylpiperazinotetrahydronaphthols and derivatives
US4556669A (en)	1985-12-03	2,-3-Di-substituted-5,6-dihydroimidazo [2,1-b] thiazole, its salts, production thereof and anti-inflammatory agent containing the same
JP5305593B2 (ja)	2013-10-02	高化学的ｒ−５−（２−（２−エトキシフェノキシエチルアミノ）プロピル）−２−メトキシベンゼンスルホンアミド塩酸塩の調製
JP3901239B2 (ja)	2007-04-04	アリールアルカン誘導体
US4714700A (en)	1987-12-22	N-substituted 2,4-dialkoxy benzenesulfonamides and pharmaceutical compositions
JPS59205383A (ja)	1984-11-20	フラノピリジン誘導体
US3766245A (en)	1973-10-16	3,5-dialkoxyalkoxy-4-substituted benzoic acid esters
JPH0737442B2 (ja)	1995-04-26	アニリン類及びベンジルアミン類から得られるベンジルセレノベンズアミド類、及びその製造方法
NO881899L (no)	1988-11-03	Nye 2-aminoalkyl-4-benzyl-1-(2h)-ftalazino-derivater.
US3278599A (en)	1966-10-11	2-(benzyloxyalkyl)-4-phenylimino-1, 3-cyclopentanedione derivatives
US3577435A (en)	1971-05-04	Process for the preparation of 3-aryl-2-imino-3-indolinols and related compounds
JPS59186915A (ja)	1984-10-23	メタ−（スルホンアミド）ベンズアミド系向精神薬

JPS5920667B2 - スルホンアミド系ベンズアミド誘導体 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (26)

Applications Claiming Priority (1)

Related Child Applications (1)

Publications (2)

Family

ID=11693258

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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