JPS5833221B2 - シンキナアミノアシルアニリドカゴウブツノセイホウ - Google Patents

シンキナアミノアシルアニリドカゴウブツノセイホウ

Info

Publication number: JPS5833221B2
Authority: JP; Japan
Prior art keywords: hydrogen; methyl; ethyl; group; amino
Prior art date: 1973-01-08
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

JP49005015A

Other languages

English (en)

Japanese (ja)

Other versions

JPS49116034A (fr

Inventor

リチヤードスミスエミル

ランドールデユースベンジヤミン

ウイリアムバーンズユージン

ニコルボイエスロバート

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.)

Hassle AB

Original Assignee

Hassle AB

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.)

1973-01-08

Filing date

1974-01-07

Publication date

1983-07-18

1974-01-07 Application filed by Hassle AB filed Critical Hassle AB

1974-11-06 Publication of JPS49116034A publication Critical patent/JPS49116034A/ja

1983-07-18 Publication of JPS5833221B2 publication Critical patent/JPS5833221B2/ja

Status Expired legal-status Critical Current

Links

-1 aminoacyl anilide Chemical class 0.000 title description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
229910052739 hydrogen Inorganic materials 0.000 claims description 103
239000001257 hydrogen Substances 0.000 claims description 101
150000002431 hydrogen Chemical group 0.000 claims description 57
150000001875 compounds Chemical class 0.000 claims description 50
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
229910021529 ammonia Inorganic materials 0.000 claims description 9
230000003287 optical effect Effects 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
NSKGQURZWSPSBC-VVPCINPTSA-N ribostamycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](N)C[C@@H]1N NSKGQURZWSPSBC-VVPCINPTSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
239000003153 chemical reaction reagent Substances 0.000 claims 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
239000000203 mixture Substances 0.000 description 41
239000000243 solution Substances 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
230000015572 biosynthetic process Effects 0.000 description 27
238000003786 synthesis reaction Methods 0.000 description 27
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000002585 base Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000007787 solid Substances 0.000 description 13
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
208000003663 ventricular fibrillation Diseases 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 7
239000003416 antiarrhythmic agent Substances 0.000 description 7
239000000284 extract Substances 0.000 description 7
235000015320 potassium carbonate Nutrition 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
230000003288 anthiarrhythmic effect Effects 0.000 description 6
239000002775 capsule Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 6
239000012530 fluid Substances 0.000 description 6
229960004194 lidocaine Drugs 0.000 description 6
239000003589 local anesthetic agent Substances 0.000 description 6
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
229940087562 sodium acetate trihydrate Drugs 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
206010003119 arrhythmia Diseases 0.000 description 4
206010061592 cardiac fibrillation Diseases 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000002600 fibrillogenic effect Effects 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
230000029058 respiratory gaseous exchange Effects 0.000 description 4
239000002002 slurry Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000011282 treatment Methods 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
ZVBAPPZCAFKUKN-UHFFFAOYSA-N 2,6-dimethyl-4-propoxyaniline Chemical compound CCCOC1=CC(C)=C(N)C(C)=C1 ZVBAPPZCAFKUKN-UHFFFAOYSA-N 0.000 description 3
ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 3
ATSGOICIGSRYNV-UHFFFAOYSA-N 3-amino-n-(2-ethyl-6-methylphenyl)propanamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CCN ATSGOICIGSRYNV-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 3
230000003444 anaesthetic effect Effects 0.000 description 3
230000006793 arrhythmia Effects 0.000 description 3
238000000576 coating method Methods 0.000 description 3
229960001270 d- tartaric acid Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229960005015 local anesthetics Drugs 0.000 description 3
229960002036 phenytoin Drugs 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000001629 suppression Effects 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000002861 ventricular Effects 0.000 description 3
QXINHCPSJNJFOL-UHFFFAOYSA-N 2-amino-n-(2,3,6-trimethylphenyl)acetamide Chemical compound CC1=CC=C(C)C(NC(=O)CN)=C1C QXINHCPSJNJFOL-UHFFFAOYSA-N 0.000 description 2
SWWACRQMECSAGR-UHFFFAOYSA-N 2-amino-n-(4-butoxy-2,6-dimethylphenyl)propanamide Chemical compound CCCCOC1=CC(C)=C(NC(=O)C(C)N)C(C)=C1 SWWACRQMECSAGR-UHFFFAOYSA-N 0.000 description 2
SQBYZLSKEHLGCY-UHFFFAOYSA-N 2-bromo-n-(2-ethyl-6-methylphenyl)propanamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)C(C)Br SQBYZLSKEHLGCY-UHFFFAOYSA-N 0.000 description 2
RWAUXUKNHFCMJV-UHFFFAOYSA-N 2-chloro-n-(2,3,6-trimethylphenyl)acetamide Chemical compound CC1=CC=C(C)C(NC(=O)CCl)=C1C RWAUXUKNHFCMJV-UHFFFAOYSA-N 0.000 description 2
RFELJRSFWNBKHL-UHFFFAOYSA-N 3-amino-n-(2,6-dimethyl-4-propoxyphenyl)propanamide Chemical compound CCCOC1=CC(C)=C(NC(=O)CCN)C(C)=C1 RFELJRSFWNBKHL-UHFFFAOYSA-N 0.000 description 2
OXCRLLANEWZJPQ-UHFFFAOYSA-N 3-bromo-n-(2-ethyl-6-methylphenyl)propanamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CCBr OXCRLLANEWZJPQ-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
XZJZXPFFLHBNGJ-UHFFFAOYSA-N Cc1cc(O)cc(C)c1N=Nc1ccccc1 Chemical compound Cc1cc(O)cc(C)c1N=Nc1ccccc1 XZJZXPFFLHBNGJ-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
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 description 2
229930195725 Mannitol Natural products 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
LBJVHMAYBNQJBK-UHFFFAOYSA-N N-(2,6-diethylphenyl)-2-chloroacetamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)CCl LBJVHMAYBNQJBK-UHFFFAOYSA-N 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000003931 anilides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000000460 chlorine Chemical group 0.000 description 2
229910052801 chlorine Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000033001 locomotion Effects 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000033764 rhythmic process Effects 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000007939 sustained release tablet Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
YQBUUEDECWZPTJ-UHFFFAOYSA-N (2,6-dimethyl-4-propoxyphenyl)-phenyldiazene Chemical compound CC1=CC(OCCC)=CC(C)=C1N=NC1=CC=CC=C1 YQBUUEDECWZPTJ-UHFFFAOYSA-N 0.000 description 1
LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical class C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 description 1
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
NXCNEIVTXXRMOY-UHFFFAOYSA-N 2-amino-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)CN NXCNEIVTXXRMOY-UHFFFAOYSA-N 0.000 description 1
BPEGXLVMGOSTGK-UHFFFAOYSA-N 2-amino-n-(2,6-diethylphenyl)propanamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C(C)N BPEGXLVMGOSTGK-UHFFFAOYSA-N 0.000 description 1
ZYMZLQYSLUNBPO-UHFFFAOYSA-N 2-amino-n-(2-ethyl-6-methylphenyl)acetamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CN ZYMZLQYSLUNBPO-UHFFFAOYSA-N 0.000 description 1
HPQVCXPZGHHDOZ-UHFFFAOYSA-N 2-amino-n-(2-ethyl-6-methylphenyl)propanamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)C(C)N HPQVCXPZGHHDOZ-UHFFFAOYSA-N 0.000 description 1
KGLDIFVKGFFTLX-UHFFFAOYSA-N 2-bromo-n-(2,6-dimethyl-4-propoxyphenyl)propanamide Chemical compound CCCOC1=CC(C)=C(NC(=O)C(C)Br)C(C)=C1 KGLDIFVKGFFTLX-UHFFFAOYSA-N 0.000 description 1
FRXLFVNGTPQFEJ-UHFFFAOYSA-N 3-bromopropanoyl bromide Chemical compound BrCCC(Br)=O FRXLFVNGTPQFEJ-UHFFFAOYSA-N 0.000 description 1
KIHUWAOTZVYMFH-UHFFFAOYSA-N 4-butoxy-2,6-dimethylaniline Chemical compound CCCCOC1=CC(C)=C(N)C(C)=C1 KIHUWAOTZVYMFH-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
238000005642 Gabriel synthesis reaction Methods 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
108010061951 Methemoglobin Proteins 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
SMINYPCTNJDYGK-UHFFFAOYSA-N N-(2-ethyl-6-methylphenyl)-2-chloroacetamide Chemical compound CCC1=CC=CC(C)=C1NC(=O)CCl SMINYPCTNJDYGK-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
208000009729 Ventricular Premature Complexes Diseases 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
CASOXAYOCHCWQU-UHFFFAOYSA-N butan-2-one;ethanol Chemical compound CCO.CCC(C)=O CASOXAYOCHCWQU-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
238000011281 clinical therapy Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000857 drug effect Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
210000005003 heart tissue Anatomy 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
IILPUHXLVPEPAV-UHFFFAOYSA-N n-ethyl-2,3-dimethylaniline Chemical group CCNC1=CC=CC(C)=C1C IILPUHXLVPEPAV-UHFFFAOYSA-N 0.000 description 1
OAPVPGPVBZRARK-UHFFFAOYSA-N n-ethyl-2,6-dimethylaniline Chemical group CCNC1=C(C)C=CC=C1C OAPVPGPVBZRARK-UHFFFAOYSA-N 0.000 description 1
MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000011422 pharmacological therapy Methods 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 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
REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
229960000244 procainamide Drugs 0.000 description 1
239000008213 purified water Substances 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
102220067365 rs143592561 Human genes 0.000 description 1
238000009738 saturating Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
229940072358 xylocaine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP49005015A 1973-01-08 1974-01-07 シンキナアミノアシルアニリドカゴウブツノセイホウ Expired JPS5833221B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32159073A	1973-01-08	1973-01-08
US32180073A	1973-01-08	1973-01-08

Publications (2)

Publication Number	Publication Date
JPS49116034A JPS49116034A (fr)	1974-11-06
JPS5833221B2 true JPS5833221B2 (ja)	1983-07-18

Family

ID=26983031

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP49005015A Expired JPS5833221B2 (ja)	1973-01-08	1974-01-07	シンキナアミノアシルアニリドカゴウブツノセイホウ

Country Status (13)

Country	Link
JP (1)	JPS5833221B2 (fr)
AR (2)	AR205617A1 (fr)
CA (1)	CA1024528A (fr)
CH (2)	CH603556A5 (fr)
DD (1)	DD113749A5 (fr)
DE (1)	DE2400540A1 (fr)
ES (1)	ES422085A1 (fr)
FR (1)	FR2213065B1 (fr)
GB (1)	GB1461602A (fr)
HU (1)	HU166667B (fr)
IE (1)	IE39541B1 (fr)
NL (1)	NL7400167A (fr)
SU (2)	SU563119A3 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4098895A (en) *	1975-09-30	1978-07-04	Ciba-Geigy Corporation	Triazolylacetanilide compounds and microbicidal compositions
GB2267709A (en) *	1992-06-11	1993-12-15	Merck & Co Inc	Novel process for the preparation of alpha-aminoacylanilides

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB705460A (en) *	1951-02-26	1954-03-10	Astra Apotekarnes Kem Fab	Process for the preparation of aminoacetyl-anilides having alkyl substituents at theamino nitrogen and products thereof
DE939207C (de) *	1952-02-25	1956-02-16	Cilag Ag	Verfahren zur Herstellung von als Lokalanaesthetica verwendbaren basisch substituierten Fettsaeure-(2-chlor-6-methyl-aniliden) und ihren Salzen
DE1046059B (de) *	1952-06-12	1958-12-11	Astra Ab	Verfahren zur Herstellung von als lokalanaesthetische Mittel verwendbaren N-Alkyl-alaninaniliden
US2912460A (en) *	1952-08-18	1959-11-10	Hoechst Ag	Basically substituted carboxylic acid amides and a process of preparing them
FR1167026A (fr) *	1953-08-21	1958-11-19	Hoechst Ag	Amides d'acides à substituant basique et procédé de préparation de ces amides d'acides
DE1001277B (de) *	1953-11-10	1957-01-24	Leo Pharm Prod Ltd	Verfahren zur Herstellung von lokalanaesthetisch wirksamen Dialkylaminoacylaniliden
CH318077A (de) *	1954-01-29	1956-12-15	Cilag Ag	Verfahren zur Herstellung von B-Amino-buttersäureaniliden
DE1055541B (de) *	1954-11-01	1959-04-23	Geistlich Soehne Ag	Verfahren zur Herstellung von beta-Dialkylaminoacylaniliden
DE1028099B (de) *	1955-06-11	1958-04-17	Goesta Lennart Flemmert Dr Tec	Verfahren zur Herstellung von amorphem, feinverteiltem Siliciumdioxyd
DE1170856B (de) *	1960-10-11	1964-05-21	Degussa	Verfahren zur Herstellung von festhaftenden und loetfaehigen Metallschichten, insbesondere Silberschichten, auf keramischem Material, insbesondere Aluminiumoxydkoerpern
GB1028099A (en)	1965-03-30	1966-05-04	Tanabe Seiyaku Co	Substituted propionanilides
CH449042A (de) *	1965-04-02	1967-12-31	Tanabe Seiyaku Co	Verfahren zur Herstellung substituierter Propionanilide
SE337810B (fr)	1966-05-13	1971-08-23	Tanabe Seiyaku Co

1974
- 1974-01-01 AR AR251845A patent/AR205617A1/es active
- 1974-01-04 SU SU1982938A patent/SU563119A3/ru active
- 1974-01-07 FR FR7400485A patent/FR2213065B1/fr not_active Expired
- 1974-01-07 NL NL7400167A patent/NL7400167A/xx not_active Application Discontinuation
- 1974-01-07 JP JP49005015A patent/JPS5833221B2/ja not_active Expired
- 1974-01-07 ES ES422085A patent/ES422085A1/es not_active Expired
- 1974-01-07 DD DD175865A patent/DD113749A5/xx unknown
- 1974-01-07 IE IE28/74A patent/IE39541B1/xx unknown
- 1974-01-07 CH CH1010277A patent/CH603556A5/xx not_active IP Right Cessation
- 1974-01-07 CH CH14174A patent/CH596148A5/xx not_active IP Right Cessation
- 1974-01-07 HU HUAA763A patent/HU166667B/hu unknown
- 1974-01-07 CA CA189,559A patent/CA1024528A/fr not_active Expired
- 1974-01-07 DE DE2400540A patent/DE2400540A1/de not_active Ceased
- 1974-01-07 GB GB57074A patent/GB1461602A/en not_active Expired
1975
- 1975-03-24 SU SU752116825A patent/SU656504A3/ru active
- 1975-09-26 AR AR260567A patent/AR211695A1/es active

Also Published As

Publication number	Publication date
AR205617A1 (es)	1976-05-21
DD113749A5 (fr)	1975-06-20
ES422085A1 (es)	1977-01-01
CH603556A5 (fr)	1978-08-31
SU563119A3 (ru)	1977-06-25
HU166667B (fr)	1975-05-28
JPS49116034A (fr)	1974-11-06
FR2213065A1 (fr)	1974-08-02
CA1024528A (fr)	1978-01-17
GB1461602A (en)	1977-01-13
IE39541L (en)	1974-07-08
NL7400167A (fr)	1974-07-10
DE2400540A1 (de)	1974-08-15
FR2213065B1 (fr)	1978-01-06
CH596148A5 (fr)	1978-02-28
AR211695A1 (es)	1978-02-28
IE39541B1 (en)	1978-11-08
AU6424774A (en)	1975-07-10
SU656504A3 (ru)	1979-04-05

Publication	Publication Date	Title
US4400394A (en)	1983-08-23	Benzylidene derivatives
JPS62167767A (ja)	1987-07-24	デカヒドロキノリンの新誘導体、それらの製造法及び薬剤
CH683427A5 (fr)	1994-03-15	Composé d'isoquinoléine comme agents de blocage neuromusculaire.
EP0003029B1 (fr)	1980-12-10	Nouveaux dérivés de l'acide 2-oxo-1-pyrrolidine-acétique, procédé pour leur préparation, médicaments les contenant et procédé pour leur préparation
DE4333761A1 (de)	1995-04-06	Heterocyclische Carbamate, Verfahren zu ihrer Herstellung und Arzneimittel
EP0025192A2 (fr)	1981-03-18	Acides oxiranne-carboxyliques substitués, procédé pour leur préparation, leur utilisation et médicaments les contenant
DE1914456A1 (de)	1971-06-16	Papaveringlyoxylat,seine Herstellung und Verwendung
US3445518A (en)	1969-05-20	P-acylphenylethylamines
US3402198A (en)	1968-09-17	2-(phenoxy), 2-(phenylthio) and 2-(anilino) substituted 2-alkylideneacetic acid derivatives
JPS5833221B2 (ja)	1983-07-18	シンキナアミノアシルアニリドカゴウブツノセイホウ
US4218477A (en)	1980-08-19	Primary aminoacylanilides, methods of making the same and use as antiarrhythmic drugs
FR2460294A1 (fr)	1981-01-23	Nouveaux oxime-ethers, leur procede de preparation et compositions pharmaceutiques les contenant
US3845123A (en)	1974-10-29	Phenoxypropanolamine therapeutic agents
JPH0471067B2 (fr)	1992-11-12
US3248292A (en)	1966-04-26	Pharmaceutically active dimethoxyquinazolines
US4237068A (en)	1980-12-02	Primary aminoacylanilides
RU2068261C1 (ru)	1996-10-27	Антиаритмическое средство
HU180617B (en)	1983-03-28	Process for producing 1,2-bis-bracket-nicotinamido-bracket closed-propane,salts and pharmaceutical compositions containing them
US3961072A (en)	1976-06-01	Phenoxypropanolamine therapeutic agents
CH645357A5 (fr)	1984-09-28	Imino-2-imidazolidines 4-substituees utiles en therapie et des medicaments les contenant.
FI57254C (fi)	1980-07-10	Analogifoerfarande foer framstaellning av antiarytmiskt aktiva primaera aminoacylanilider
US4053603A (en)	1977-10-11	Benzylisoquinoline derivatives, and use as anti-arrhythmic drugs
US3487154A (en)	1969-12-30	Method of lowering blood pressure
US3056792A (en)	1962-10-02	Unsymmetrical 1, 3-diamino-2-propanols
JPS6154777B2 (fr)	1986-11-25