AT317196B - Verfahren zur Herstellung neuer 1-Benzoyloxy-2-niedrig-alkylaminobenzocycloalkanderivate - Google Patents

Verfahren zur Herstellung neuer 1-Benzoyloxy-2-niedrig-alkylaminobenzocycloalkanderivate

Info

Publication number: AT317196B
Authority: AT; Austria
Prior art keywords: sep; dimethylaminotetralin; compound; cis; benzoyloxy
Prior art date: 1971-06-22

Application number

AT535272A

Other languages

German (de)

English (en)

Inventor

Murakami Masuo

Hirata Yasubumi

Takeda Masaaki

Ino Hiroki

Original Assignee

Yamanouchi Pharma 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.)

1971-06-22

Filing date

1972-06-21

Publication date

1974-08-12

1972-06-21 Application filed by Yamanouchi Pharma Co Ltd filed Critical Yamanouchi Pharma Co Ltd

1973-08-22 Priority to AT731873A priority Critical patent/AT333266B/de

1974-08-12 Application granted granted Critical

1974-08-12 Publication of AT317196B publication Critical patent/AT317196B/de

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
150000001875 compounds Chemical class 0.000 description 41
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000000047 product Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
-1 dimethylamino compound Chemical class 0.000 description 12
239000003589 local anesthetic agent Substances 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000013078 crystal Substances 0.000 description 11
230000003444 anaesthetic effect Effects 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
210000004051 gastric juice Anatomy 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
208000007882 Gastritis Diseases 0.000 description 6
239000000284 extract Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000243 solution Substances 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-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
239000002253 acid Substances 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
ZAQRZIOJHJSUMA-UHFFFAOYSA-N 1-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1=CC=C2C(N(C)C)C(O)CCC2=C1 ZAQRZIOJHJSUMA-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
FTVLIUAUWUINLT-UHFFFAOYSA-N [2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-yl] benzoate;hydrochloride Chemical compound [Cl-].C[NH+](C)C1CCC2=CC=CC=C2C1OC(=O)C1=CC=CC=C1 FTVLIUAUWUINLT-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000004899 motility Effects 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
VLSPYRNKOSGIIW-VXGBXAGGSA-N (1r,2r)-2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2[C@@H](O)[C@H](N(C)C)CCC2=C1 VLSPYRNKOSGIIW-VXGBXAGGSA-N 0.000 description 2
HPIUUGOSAPZIEG-UHFFFAOYSA-N (2-benzoyloxy-1,2,3,4-tetrahydronaphthalen-1-yl)-dimethylazanium;chloride Chemical compound [Cl-].C1CC2=CC=CC=C2C([NH+](C)C)C1OC(=O)C1=CC=CC=C1 HPIUUGOSAPZIEG-UHFFFAOYSA-N 0.000 description 2
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 2
VLSPYRNKOSGIIW-UHFFFAOYSA-N 2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)C(N(C)C)CCC2=C1 VLSPYRNKOSGIIW-UHFFFAOYSA-N 0.000 description 2
IIMSEFZOOYSTDO-UHFFFAOYSA-N 2-amino-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)C(N)CCC2=C1 IIMSEFZOOYSTDO-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FTLDJPRFCGDUFH-UHFFFAOYSA-N Oxethazaine Chemical compound C=1C=CC=CC=1CC(C)(C)N(C)C(=O)CN(CCO)CC(=O)N(C)C(C)(C)CC1=CC=CC=C1 FTLDJPRFCGDUFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006480 benzoylation reaction Methods 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
208000023652 chronic gastritis Diseases 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
230000030135 gastric motility Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000011835 investigation Methods 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229960000986 oxetacaine Drugs 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
IIMSEFZOOYSTDO-NXEZZACHSA-N (1r,2r)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2[C@@H](O)[C@H](N)CCC2=C1 IIMSEFZOOYSTDO-NXEZZACHSA-N 0.000 description 1
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 1
GIQQAQFTVJTULV-UHFFFAOYSA-N 1,3-oxazol-3-ium;chloride Chemical compound Cl.C1=COC=N1 GIQQAQFTVJTULV-UHFFFAOYSA-N 0.000 description 1
VFLKZHRZQTVWBE-UHFFFAOYSA-N 1-(dimethylamino)-3,4-dihydro-2H-naphthalen-1-ol Chemical compound C1=CC=C2C(N(C)C)(O)CCCC2=C1 VFLKZHRZQTVWBE-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
DJDAPLBWGIXUAG-UHFFFAOYSA-N 2-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(Cl)=O DJDAPLBWGIXUAG-UHFFFAOYSA-N 0.000 description 1
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
CWANAJQMHZVLGX-UHFFFAOYSA-N 3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-4-ol Chemical compound NC=1C=CC2=C(CCCCC2)C1O CWANAJQMHZVLGX-UHFFFAOYSA-N 0.000 description 1
YBCOOGQGBVDQSB-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(Cl)=O YBCOOGQGBVDQSB-UHFFFAOYSA-N 0.000 description 1
NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
206010000087 Abdominal pain upper Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WTBPBTGMXKEUHJ-UHFFFAOYSA-N Cl.C(C)NC1C(C2=CC=CC=C2C1)O Chemical compound Cl.C(C)NC1C(C2=CC=CC=C2C1)O WTBPBTGMXKEUHJ-UHFFFAOYSA-N 0.000 description 1
KJDHJYUJPNODDK-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)(=O)OC1C(CC2=CC=CC=C12)NCC Chemical compound Cl.C(C1=CC=CC=C1)(=O)OC1C(CC2=CC=CC=C12)NCC KJDHJYUJPNODDK-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
BASBFGPZXIWCLP-UHFFFAOYSA-N NC1=CC=C(C(=O)OC2C(C3=CC=CC=C3CC2)N(C)C)C=C1 Chemical class NC1=CC=C(C(=O)OC2C(C3=CC=CC=C3CC2)N(C)C)C=C1 BASBFGPZXIWCLP-UHFFFAOYSA-N 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
RXCYZGYZJKOTRV-UHFFFAOYSA-N OC1=C(C=CC2=C1CCCCC2)N(C)C Chemical compound OC1=C(C=CC2=C1CCCCC2)N(C)C RXCYZGYZJKOTRV-UHFFFAOYSA-N 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
KVSHZSBORGCZRT-UHFFFAOYSA-N [2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-yl] 4-aminobenzoate Chemical class CN(C)C1CCC2=CC=CC=C2C1OC(=O)C1=CC=C(N)C=C1 KVSHZSBORGCZRT-UHFFFAOYSA-N 0.000 description 1
GGTRPFJSSOOBRR-UHFFFAOYSA-N [2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-yl] 4-nitrobenzoate Chemical compound CN(C1C(C2=CC=CC=C2CC1)OC(C1=CC=C(C=C1)[N+](=O)[O-])=O)C GGTRPFJSSOOBRR-UHFFFAOYSA-N 0.000 description 1
LBQGJHNNGUZLOH-UHFFFAOYSA-N [2-(dimethylamino)-1,2,3,4-tetrahydronaphthalen-1-yl] benzoate Chemical compound CN(C)C1CCC2=CC=CC=C2C1OC(=O)C1=CC=CC=C1 LBQGJHNNGUZLOH-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
GUXSVLKPLFZZEV-UHFFFAOYSA-N benzene;benzoyl chloride Chemical compound C1=CC=CC=C1.ClC(=O)C1=CC=CC=C1 GUXSVLKPLFZZEV-UHFFFAOYSA-N 0.000 description 1
WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000035876 healing Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000003152 motion sickness Diseases 0.000 description 1
UYOZHOUPIHNUJN-UHFFFAOYSA-N n-(1-oxo-3,4-dihydro-2h-naphthalen-2-yl)acetamide Chemical compound C1=CC=C2C(=O)C(NC(=O)C)CCC2=C1 UYOZHOUPIHNUJN-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
230000036407 pain Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

AT535272A 1971-06-22 1972-06-21 Verfahren zur Herstellung neuer 1-Benzoyloxy-2-niedrig-alkylaminobenzocycloalkanderivate AT317196B (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT731873A AT333266B (de)	1971-12-10	1973-08-22	Verfahren zur herstellung neuer 1-benzoyloxy-2-dimethylaminobenzocycloalkanderivate

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP46044491A JPS516669B1 (2)	1971-06-22	1971-06-22

Publications (1)

Publication Number	Publication Date
AT317196B true AT317196B (de)	1974-08-12

Family

ID=12693006

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT535272A AT317196B (de)	1971-06-22	1972-06-21	Verfahren zur Herstellung neuer 1-Benzoyloxy-2-niedrig-alkylaminobenzocycloalkanderivate

Country Status (2)

Country	Link
JP (1)	JPS516669B1 (2)
AT (1)	AT317196B (2)

1971
- 1971-06-22 JP JP46044491A patent/JPS516669B1/ja active Pending
1972
- 1972-06-21 AT AT535272A patent/AT317196B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS516669B1 (2)	1976-03-01

Legal Events

Date	Code	Title	Description
1979-09-15	ELJ	Ceased due to non-payment of the annual fee

Publication	Publication Date	Title
DE1245357B (de)	1967-07-27	Verfahren zur Herstellung von basischen AEthern von substituierten Hydroxybenzoesaeureamiden
AT317196B (de)	1974-08-12	Verfahren zur Herstellung neuer 1-Benzoyloxy-2-niedrig-alkylaminobenzocycloalkanderivate
CH643843A5 (de)	1984-06-29	Phenthiazin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.
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DE2216627C3 (de)	1975-10-09	2,4,6-Trijodbenzoe säurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel
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DE3420387A1 (de)	1984-12-06	2-(4-biphenylyl)-4-hexenonsaeure und ihre derivate mit entzuendungshemmender wirksamkeit
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