DE2803651C2 - - Google Patents
Info
- Publication number
- DE2803651C2 DE2803651C2 DE2803651A DE2803651A DE2803651C2 DE 2803651 C2 DE2803651 C2 DE 2803651C2 DE 2803651 A DE2803651 A DE 2803651A DE 2803651 A DE2803651 A DE 2803651A DE 2803651 C2 DE2803651 C2 DE 2803651C2
- Authority
- DE
- Germany
- Prior art keywords
- methylene chloride
- general formula
- mixture
- compound
- methoxy
- Prior art date
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 16
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000000506 psychotropic effect Effects 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 194
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- -1 1-ethyl-2-pyrrolidinylmethyl Chemical group 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000013078 crystal Substances 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 239000000284 extract Substances 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 229960004046 apomorphine Drugs 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- ZUNMZCCDRLBDHW-UHFFFAOYSA-N 4-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(methanesulfonamido)-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=C(Cl)C=C1OC ZUNMZCCDRLBDHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 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
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- YTRPYXNQCLTHGY-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(methanesulfonamido)-2-methoxy-4-methylbenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(C)(=O)=O)=C(C)C=C1OC YTRPYXNQCLTHGY-UHFFFAOYSA-N 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-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
- WBXMKLUMWBPNFY-UHFFFAOYSA-N 2-(methanesulfonamido)benzamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1C(N)=O WBXMKLUMWBPNFY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- UFEYMXHWIHFRBX-UHFFFAOYSA-N 4-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(Cl)=CC=C1C(O)=O UFEYMXHWIHFRBX-UHFFFAOYSA-N 0.000 description 2
- XOUZIGCMSMPFJW-UHFFFAOYSA-N 4-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(N(C)S(C)(=O)=O)=C(Cl)C=C1OC XOUZIGCMSMPFJW-UHFFFAOYSA-N 0.000 description 2
- GJPQDUZAQIKKLP-UHFFFAOYSA-N 5-(dimethylsulfamoylamino)-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-4-methylbenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(NS(=O)(=O)N(C)C)=C(C)C=C1OC GJPQDUZAQIKKLP-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000003474 anti-emetic effect Effects 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000009194 climbing Effects 0.000 description 2
- 230000002493 climbing effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- 238000006396 nitration reaction Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 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
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 229960004940 sulpiride Drugs 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DWCNNQOORRREID-UHFFFAOYSA-N 1,2-dichloroethane;methanol Chemical compound OC.ClCCCl DWCNNQOORRREID-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VESLFCBOKMWCRG-UHFFFAOYSA-N 2-(methanesulfonamido)benzoic acid Chemical compound CS(=O)(=O)NC1=CC=CC=C1C(O)=O VESLFCBOKMWCRG-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
- SHQLDMYDWWQOTE-UHFFFAOYSA-N 2-amino-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=CC=C1N SHQLDMYDWWQOTE-UHFFFAOYSA-N 0.000 description 1
- WOUHOYPYLXMUBX-UHFFFAOYSA-N 2-methoxy-4-methyl-5-nitro-n-(oxolan-2-ylmethyl)benzamide Chemical compound COC1=CC(C)=C([N+]([O-])=O)C=C1C(=O)NCC1OCCC1 WOUHOYPYLXMUBX-UHFFFAOYSA-N 0.000 description 1
- NCLYYORBPCUMMU-UHFFFAOYSA-N 2-methoxy-4-methyl-5-nitrobenzoyl chloride Chemical compound COC1=CC(C)=C([N+]([O-])=O)C=C1C(Cl)=O NCLYYORBPCUMMU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- ICKSVMFXUYDIHY-UHFFFAOYSA-N 4-chloro-5-(methanesulfonamido)-2-methoxy-n-(oxolan-2-ylmethyl)benzamide Chemical compound COC1=CC(Cl)=C(NS(C)(=O)=O)C=C1C(=O)NCC1OCCC1 ICKSVMFXUYDIHY-UHFFFAOYSA-N 0.000 description 1
- LADDWJQJDLVDDQ-UHFFFAOYSA-N 4-chloro-5-(methanesulfonamido)-2-methoxybenzamide Chemical compound COC1=C(C(=O)N)C=C(C(=C1)Cl)NS(=O)(=O)C LADDWJQJDLVDDQ-UHFFFAOYSA-N 0.000 description 1
- PFOCWZPYPDJLDD-UHFFFAOYSA-N 4-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-nitrobenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC([N+]([O-])=O)=C(Cl)C=C1OC PFOCWZPYPDJLDD-UHFFFAOYSA-N 0.000 description 1
- KFSRRMLGVKUHBX-UHFFFAOYSA-N 5-(dimethylsulfamoylamino)-2-methoxy-4-methylbenzamide Chemical compound COC1=C(C(=O)N)C=C(C(=C1)C)NS(=O)(=O)N(C)C KFSRRMLGVKUHBX-UHFFFAOYSA-N 0.000 description 1
- HUOHHUJXRCEBQL-UHFFFAOYSA-N 5-(methanesulfonamido)-2-methoxy-4-methylbenzoic acid Chemical compound COC1=CC(C)=C(NS(C)(=O)=O)C=C1C(O)=O HUOHHUJXRCEBQL-UHFFFAOYSA-N 0.000 description 1
- NNTFWYNGJHNGAG-UHFFFAOYSA-N 5-amino-2-methoxy-4-methyl-n-(oxolan-2-ylmethyl)benzamide Chemical compound COC1=CC(C)=C(N)C=C1C(=O)NCC1OCCC1 NNTFWYNGJHNGAG-UHFFFAOYSA-N 0.000 description 1
- MHVXZVUZIMIXGR-UHFFFAOYSA-N 5-amino-4-chloro-2-methoxy-n-(oxolan-2-ylmethyl)benzamide Chemical compound COC1=CC(Cl)=C(N)C=C1C(=O)NCC1OCCC1 MHVXZVUZIMIXGR-UHFFFAOYSA-N 0.000 description 1
- PTRQVDVQOWYCES-UHFFFAOYSA-N 5-amino-4-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(N)=C(Cl)C=C1OC PTRQVDVQOWYCES-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 230000008485 antagonism Effects 0.000 description 1
- 230000003354 anti-apomorphinic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 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
- FVWDBVACVTXVJN-UHFFFAOYSA-L dipotassium;propan-2-one;carbonate Chemical compound [K+].[K+].CC(C)=O.[O-]C([O-])=O FVWDBVACVTXVJN-UHFFFAOYSA-L 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- CEALXSHFPPCRNM-UHFFFAOYSA-L disodium;carboxylato carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OC([O-])=O CEALXSHFPPCRNM-UHFFFAOYSA-L 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 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
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 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
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- JHPQEXUCADZGGU-UHFFFAOYSA-N methylsulfonyl 2-aminobenzoate Chemical compound CS(=O)(=O)OC(=O)C1=CC=CC=C1N JHPQEXUCADZGGU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- MMVCVPRWHIYIDW-UHFFFAOYSA-N n-(2,5-dichloropentyl)-5-(dimethylsulfamoylamino)-2-methoxy-4-methylbenzamide Chemical compound COC1=CC(C)=C(NS(=O)(=O)N(C)C)C=C1C(=O)NCC(Cl)CCCCl MMVCVPRWHIYIDW-UHFFFAOYSA-N 0.000 description 1
- UJJUEJRWNWVHCM-UHFFFAOYSA-N n-methylsulfamoyl chloride Chemical compound CNS(Cl)(=O)=O UJJUEJRWNWVHCM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52008443A JPS5920667B2 (ja) | 1977-01-27 | 1977-01-27 | スルホンアミド系ベンズアミド誘導体 |
| JP52094884A JPS5822110B2 (ja) | 1977-08-08 | 1977-08-08 | ベンズアミド誘導体の合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2803651A1 DE2803651A1 (de) | 1978-08-03 |
| DE2803651C2 true DE2803651C2 (en, 2012) | 1988-10-20 |
Family
ID=26342958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782803651 Granted DE2803651A1 (de) | 1977-01-27 | 1978-01-27 | M-sulfonamidobenzamid-derivate |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US4351770A (en, 2012) |
| AR (1) | AR225881A1 (en, 2012) |
| AU (1) | AU512057B2 (en, 2012) |
| CA (1) | CA1085411A (en, 2012) |
| CH (1) | CH642945A5 (en, 2012) |
| DE (1) | DE2803651A1 (en, 2012) |
| DK (1) | DK154137C (en, 2012) |
| ES (1) | ES466366A1 (en, 2012) |
| FR (1) | FR2378758A1 (en, 2012) |
| GB (1) | GB1557019A (en, 2012) |
| GR (1) | GR70058B (en, 2012) |
| HU (1) | HU176613B (en, 2012) |
| IE (1) | IE46497B1 (en, 2012) |
| IL (1) | IL53881A (en, 2012) |
| NL (1) | NL7801005A (en, 2012) |
| NZ (1) | NZ186175A (en, 2012) |
| PH (1) | PH12853A (en, 2012) |
| SE (1) | SE426485B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| FR2485526A1 (fr) * | 1980-06-24 | 1981-12-31 | Shionogi & Co | Procede de preparation de derives de n-(diethylaminoethyl)-2 - alcoxybenzamide, nouveaux produits ainsi obtenus et leurs utilisations comme produits pharmaceutiques antiemetiques ou pour guerir les troubles gastriques |
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| PT77219B (fr) * | 1982-08-24 | 1986-02-04 | May & Baker Ltd | Procede de preparation des derives de la benzamide |
| SE8205135D0 (sv) * | 1982-09-09 | 1982-09-09 | Astra Laekemedel Ab | Benzamido-derivatives |
| FR2550447B1 (fr) * | 1983-08-10 | 1986-01-17 | Ile De France | Application du n-(ally-2-pyrrolidinylmethyl) 2-methoxy 4-amino 5-methylsulfamoyl benzamide comme antiagregant plaquettaire |
| DE3445377A1 (de) * | 1983-12-23 | 1985-07-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen |
| AU567140B2 (en) * | 1984-01-06 | 1987-11-12 | Shionogi & Co., Ltd. | Sulphonamido-benzamide derivatives |
| US4544654A (en) * | 1984-03-20 | 1985-10-01 | Schering A.G. | Substituted sulfonamidobenzamides, antiarrhythmic agents and compositions thereof |
| CA2057324A1 (en) * | 1990-12-18 | 1992-06-19 | Lora Louise Fitch | Benzamide and sulfonamide hypoglycemic agents |
| CA2350903A1 (en) * | 1998-11-20 | 2000-06-02 | F. Hoffmann-La Roche Ag | Pyrrolidine derivatives-ccr-3 receptor antagonists |
| WO2009111279A1 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Pyrazole [3, 4-b] pyridine raf inhibitors |
| US20110003809A1 (en) * | 2008-02-29 | 2011-01-06 | Array Biopharma Inc. | Imidazo [4,5-b] pyridine derivatives used as raf inhibitors |
| WO2009111280A1 (en) | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | N- (6-aminopyridin-3-yl) -3- (sulfonamido) benzamide derivatives as b-raf inhibitors for the treatment of cancer |
| JP2011513330A (ja) | 2008-02-29 | 2011-04-28 | アレイ バイオファーマ、インコーポレイテッド | Ｒａｆ阻害化合物およびその使用方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2334186A (en) * | 1938-12-20 | 1943-11-16 | Du Pont | Organic sulphonamides and their preparation |
| GB993584A (en, 2012) * | 1962-01-24 | |||
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| US3210370A (en) * | 1964-06-22 | 1965-10-05 | Upjohn Co | Process for preparing 2, 2'-methylene-bisareneimiazoles |
| FR5916M (en, 2012) * | 1966-01-21 | 1968-05-06 | ||
| FR2313935A1 (fr) * | 1975-06-10 | 1977-01-07 | Ile De France | Nouveaux benzamides substitues, leurs derives et leur procede de preparation |
| CH547797A (de) * | 1971-08-20 | 1974-04-11 | Fratmann Ag | Verfahren zur herstellung von n - ((1-aethyl-pyrrolidinyl2)-methyl) -2-methoxy-5-sulfamoyl-benzamid. |
| US4021229A (en) * | 1972-09-05 | 1977-05-03 | Stauffer Chemical Company | Sulfonamide herbicide antidote compositions and method of use |
| CH605793A5 (fr) * | 1974-03-05 | 1978-10-13 | Soc Et Scient Et Ind | Procédé de préparation de nouveaux N-(1benzylpyrrollidinil 2-alkyl) benzamides substitués |
| IL46696A (en) * | 1974-03-05 | 1978-07-31 | Soc Et Scient Et Ind | Substituted n-(2-pyrrolidinylalkyl)benzamides, their preparation and pharmaceutical compositions containing them |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
-
1978
- 1978-01-09 NZ NZ186175A patent/NZ186175A/xx unknown
- 1978-01-19 CA CA295,322A patent/CA1085411A/en not_active Expired
- 1978-01-19 GB GB2296/78A patent/GB1557019A/en not_active Expired
- 1978-01-21 GR GR55228A patent/GR70058B/el unknown
- 1978-01-23 IE IE145/78A patent/IE46497B1/en unknown
- 1978-01-24 AU AU32687/78A patent/AU512057B2/en not_active Expired
- 1978-01-24 IL IL53881A patent/IL53881A/xx unknown
- 1978-01-25 DK DK037278A patent/DK154137C/da not_active IP Right Cessation
- 1978-01-26 HU HU78SI1614A patent/HU176613B/hu not_active IP Right Cessation
- 1978-01-26 SE SE7800982A patent/SE426485B/sv not_active IP Right Cessation
- 1978-01-26 FR FR7802210A patent/FR2378758A1/fr active Granted
- 1978-01-26 AR AR270868A patent/AR225881A1/es active
- 1978-01-26 PH PH20712A patent/PH12853A/en unknown
- 1978-01-26 CH CH86678A patent/CH642945A5/de not_active IP Right Cessation
- 1978-01-26 ES ES466366A patent/ES466366A1/es not_active Expired
- 1978-01-27 NL NL7801005A patent/NL7801005A/xx not_active Application Discontinuation
- 1978-01-27 DE DE19782803651 patent/DE2803651A1/de active Granted
- 1978-12-06 US US05/967,011 patent/US4351770A/en not_active Expired - Lifetime
-
1980
- 1980-02-26 US US06/124,728 patent/US4328344A/en not_active Expired - Lifetime
- 1980-02-26 US US06/124,726 patent/US4350635A/en not_active Expired - Lifetime
- 1980-02-26 US US06/124,727 patent/US4328155A/en not_active Expired - Lifetime
- 1980-06-25 US US06/162,793 patent/US4330472A/en not_active Expired - Lifetime
-
1982
- 1982-07-15 US US06/398,702 patent/US4431663A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4328155A (en) | 1982-05-04 |
| SE7800982L (sv) | 1978-07-28 |
| HU176613B (en) | 1981-03-28 |
| DK37278A (da) | 1978-07-28 |
| DK154137C (da) | 1989-04-10 |
| ES466366A1 (es) | 1978-10-01 |
| NZ186175A (en) | 1980-03-05 |
| IL53881A (en) | 1981-05-20 |
| US4330472A (en) | 1982-05-18 |
| PH12853A (en) | 1979-09-12 |
| AU512057B2 (en) | 1980-09-18 |
| DK154137B (da) | 1988-10-17 |
| FR2378758A1 (fr) | 1978-08-25 |
| FR2378758B1 (en, 2012) | 1981-02-06 |
| GR70058B (en, 2012) | 1982-07-26 |
| IL53881A0 (en) | 1978-04-30 |
| SE426485B (sv) | 1983-01-24 |
| CH642945A5 (de) | 1984-05-15 |
| IE780145L (en) | 1978-07-27 |
| GB1557019A (en) | 1979-12-05 |
| US4351770A (en) | 1982-09-28 |
| IE46497B1 (en) | 1983-06-29 |
| DE2803651A1 (de) | 1978-08-03 |
| US4328344A (en) | 1982-05-04 |
| AU3268778A (en) | 1979-08-02 |
| US4431663A (en) | 1984-02-14 |
| NL7801005A (nl) | 1978-07-31 |
| AR225881A1 (es) | 1982-05-14 |
| CA1085411A (en) | 1980-09-09 |
| US4350635A (en) | 1982-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2803651C2 (en, 2012) | ||
| DE2047658A1 (en, 2012) | ||
| AT368130B (de) | Verfahren zur herstellung von neuen 9-aminoalkyl- fluorenen und von deren salzen | |
| DE2426149B2 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE2314639A1 (de) | Pharmakodynamisch aktive aminoalkyloximaether | |
| DE2323956A1 (de) | Substituierte naphthylanthranilsaeure | |
| DE1668550C (en, 2012) | ||
| DE2540552A1 (de) | Cycloalkylderivate von 1-aryloxy-3- amino-2-propanolen | |
| DE1620325C3 (de) | Disubstituierte Isoxazolverbindungen | |
| CH643843A5 (de) | Phenthiazin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. | |
| EP0299277A2 (de) | Verfahren zur Herstellung von substituierten Pyridylalkylketonen | |
| DE2943809A1 (de) | 1-mercaptoacylpiperazin-2-carbonsaeure-verbindungen und ihre salze, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von hypertonie | |
| DE1445800C (de) | Verfahren zur Herstellung von Diben zoazepinen | |
| AT208870B (de) | Verfahren zur Herstellung von neuen N-substituierten Azepinen bzw. Dihydroazepinen | |
| AT371445B (de) | Verfahren zur herstellung von neuen cis-4a-phenyl-isochinolinderivaten und ihren saeureadditionssalzen | |
| AT219048B (de) | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen | |
| AT332864B (de) | Verfahren zur herstellung von neuen diphenylmethoxyathylaminen und deren additionssalzen | |
| AT330779B (de) | Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen | |
| CH638490A5 (de) | Anilide mit hustenhemmender wirkung und verfahren zur herstellung derselben. | |
| AT360992B (de) | Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen | |
| AT334338B (de) | Verfahren zur herstellung von neuen alpha- (1-bis-arylalkylaminoalkyl) -aralkoxybenzylalkoholen | |
| DE1768402C2 (de) | Aminderivate des 5H-Dibenzo [a,d] cycloheptens und deren Verwendung bei der Bekämpfung von Gemütsdepressionen | |
| AT208869B (de) | Verfahren zur Herstellung von neuen N-substituierten Azepinen | |
| AT257578B (de) | Verfahren zur Herstellung von neuen Phenyl-α-aminoalkyl-ketonen und deren Säureadditionssalzen | |
| AT360991B (de) | Verfahren zur herstellung neuer 1-alkyl-4- phenylpiperidinderivate und von deren salzen und optisch aktiven verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D., DIPL.-PHYS. DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |