DE1286004B - Substituierte 3, 5-Dimethoxybenzoesaeureamide und Verfahren zu deren Herstellung - Google Patents
Substituierte 3, 5-Dimethoxybenzoesaeureamide und Verfahren zu deren HerstellungInfo
- Publication number
- DE1286004B DE1286004B DE1966E0031502 DEE0031502A DE1286004B DE 1286004 B DE1286004 B DE 1286004B DE 1966E0031502 DE1966E0031502 DE 1966E0031502 DE E0031502 A DEE0031502 A DE E0031502A DE 1286004 B DE1286004 B DE 1286004B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dimethoxybenzoic acid
- dimethoxybenzoic
- ecm
- amide
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- YTLRWVNYANKXOW-UHFFFAOYSA-N 3,5-dimethoxybenzamide Chemical class COC1=CC(OC)=CC(C(N)=O)=C1 YTLRWVNYANKXOW-UHFFFAOYSA-N 0.000 title claims description 4
- 230000009435 amidation Effects 0.000 claims description 9
- 238000007112 amidation reaction Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- -1 arylmethyl halide Chemical class 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 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 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000001773 anti-convulsant effect Effects 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 125000005002 aryl methyl group Chemical group 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CKPGDDSCDZFMIN-UHFFFAOYSA-N 3,5-dimethoxy-4-phenylmethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OCC1=CC=CC=C1 CKPGDDSCDZFMIN-UHFFFAOYSA-N 0.000 description 2
- OVCCGNWMGBKDIZ-UHFFFAOYSA-N 3,5-dimethoxy-4-phenylmethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OCC1=CC=CC=C1 OVCCGNWMGBKDIZ-UHFFFAOYSA-N 0.000 description 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,5-dimethoxybenzoic acid Chemical compound COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
- QNEQDTLNDBGFSC-UHFFFAOYSA-N 4-benzoyloxy-3,5-dimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC(=O)C1=CC=CC=C1 QNEQDTLNDBGFSC-UHFFFAOYSA-N 0.000 description 2
- XWMSEZHMHBQVLE-UHFFFAOYSA-N 4-hydroxy-3,5-dimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1O XWMSEZHMHBQVLE-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- REYUZOLYIOQRIG-UHFFFAOYSA-N decimemide Chemical compound CCCCCCCCCCOC1=C(OC)C=C(C(N)=O)C=C1OC REYUZOLYIOQRIG-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- REUWVCLQNTYSLY-UHFFFAOYSA-N 1-bromodecane;1-bromoundecane Chemical compound CCCCCCCCCCBr.CCCCCCCCCCCBr REUWVCLQNTYSLY-UHFFFAOYSA-N 0.000 description 1
- YXYHRDMVSILCER-UHFFFAOYSA-N 2,3,5-trimethoxybenzamide Chemical class COC1=C(C(=O)N)C=C(C=C1OC)OC YXYHRDMVSILCER-UHFFFAOYSA-N 0.000 description 1
- SDYIZAANGZBOSO-UHFFFAOYSA-N 2,3-dimethoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1OC SDYIZAANGZBOSO-UHFFFAOYSA-N 0.000 description 1
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical class COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 description 1
- HZFKKOUPDNWXPX-UHFFFAOYSA-N 3,5-dimethoxy-4-phenylmethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OCC1=CC=CC=C1 HZFKKOUPDNWXPX-UHFFFAOYSA-N 0.000 description 1
- APZBGWLAWCGETP-UHFFFAOYSA-N 4-butoxy-3,5-dimethoxybenzamide Chemical compound CCCCOC1=C(OC)C=C(C(N)=O)C=C1OC APZBGWLAWCGETP-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO000951 | 1965-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1286004B true DE1286004B (de) | 1969-01-02 |
Family
ID=10996653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966E0031502 Pending DE1286004B (de) | 1965-04-22 | 1966-04-22 | Substituierte 3, 5-Dimethoxybenzoesaeureamide und Verfahren zu deren Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3432549A (enrdf_load_stackoverflow) |
| AT (1) | AT264503B (enrdf_load_stackoverflow) |
| CH (1) | CH484061A (enrdf_load_stackoverflow) |
| DE (1) | DE1286004B (enrdf_load_stackoverflow) |
| DK (1) | DK122760B (enrdf_load_stackoverflow) |
| FR (1) | FR5442M (enrdf_load_stackoverflow) |
| NL (1) | NL142149B (enrdf_load_stackoverflow) |
| SE (1) | SE347963B (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862138A (en) * | 1970-07-31 | 1975-01-21 | Isf Spa | Heterocyclic thioamides of 4-substituted syringic acid and their preparation |
| IT1043955B (it) * | 1970-07-31 | 1980-02-29 | Isf Spa | Tioamidi dell acido siringo 4 sostituito e loro preparazione |
| WO2008044045A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2013055985A1 (en) | 2011-10-12 | 2013-04-18 | Children's Medical Center Corporation | Combinatorial compositions and methods of treating hemoglobinopathies |
| US20170349540A1 (en) * | 2014-07-28 | 2017-12-07 | The General Hospital Corporation | Histone deacetylase inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152403B (de) * | 1960-07-04 | 1963-08-08 | D Analyses Et De Rech S Biolog | Verfahren zur Herstellung von beruhigend wirkenden Benzoesaeure-amiden |
-
1966
- 1966-04-19 US US543547A patent/US3432549A/en not_active Expired - Lifetime
- 1966-04-20 CH CH568066A patent/CH484061A/de not_active IP Right Cessation
- 1966-04-20 AT AT369966A patent/AT264503B/de active
- 1966-04-22 SE SE05502/66A patent/SE347963B/xx unknown
- 1966-04-22 DK DK205966AA patent/DK122760B/da unknown
- 1966-04-22 NL NL666605460A patent/NL142149B/xx not_active IP Right Cessation
- 1966-04-22 FR FR58573A patent/FR5442M/fr not_active Expired
- 1966-04-22 DE DE1966E0031502 patent/DE1286004B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152403B (de) * | 1960-07-04 | 1963-08-08 | D Analyses Et De Rech S Biolog | Verfahren zur Herstellung von beruhigend wirkenden Benzoesaeure-amiden |
Also Published As
| Publication number | Publication date |
|---|---|
| AT264503B (de) | 1968-09-10 |
| DK122760B (da) | 1972-04-10 |
| SE347963B (enrdf_load_stackoverflow) | 1972-08-21 |
| CH484061A (de) | 1970-01-15 |
| FR5442M (enrdf_load_stackoverflow) | 1967-10-09 |
| NL6605460A (enrdf_load_stackoverflow) | 1966-10-24 |
| NL142149B (nl) | 1974-05-15 |
| US3432549A (en) | 1969-03-11 |
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