NO123720B - - Google Patents
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- Publication number
- NO123720B NO123720B NO1264/68A NO126468A NO123720B NO 123720 B NO123720 B NO 123720B NO 1264/68 A NO1264/68 A NO 1264/68A NO 126468 A NO126468 A NO 126468A NO 123720 B NO123720 B NO 123720B
- Authority
- NO
- Norway
- Prior art keywords
- chlorine
- benzyloxy
- benzamides
- radical
- mixture
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 150000003936 benzamides Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 206010002091 Anaesthesia Diseases 0.000 description 10
- -1 alkylamino radical Chemical class 0.000 description 10
- 230000037005 anaesthesia Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000003444 anaesthetic effect Effects 0.000 description 5
- 239000003589 local anesthetic agent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 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
- BELMZDGADRSOPN-UHFFFAOYSA-N 3,5-dichloro-2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1OCC1=CC=CC=C1 BELMZDGADRSOPN-UHFFFAOYSA-N 0.000 description 2
- PBBKZRNYWYWHGR-UHFFFAOYSA-N 3,5-dichloro-2-phenylmethoxybenzoyl chloride Chemical compound C(C1=CC=CC=C1)OC1=C(C(=O)Cl)C=C(C=C1Cl)Cl PBBKZRNYWYWHGR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002690 local anesthesia Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229940072358 xylocaine Drugs 0.000 description 2
- HHEKNWQXFVOUNJ-UHFFFAOYSA-N 1-(2-aminoethyl)pyrrolidin-2-one Chemical compound NCCN1CCCC1=O HHEKNWQXFVOUNJ-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- WMFCMIRCRKQLRO-UHFFFAOYSA-N 2-pyrrolidin-1-ylbutan-1-amine Chemical compound CCC(CN)N1CCCC1 WMFCMIRCRKQLRO-UHFFFAOYSA-N 0.000 description 1
- QIUMYUMHDNMHOE-UHFFFAOYSA-N 3,5-dichloro-2-[(4-chlorophenyl)methoxy]benzoyl chloride Chemical compound ClC1=CC=C(COC2=C(C(=O)Cl)C=C(C=C2Cl)Cl)C=C1 QIUMYUMHDNMHOE-UHFFFAOYSA-N 0.000 description 1
- NSHCYKGCMPCBBA-UHFFFAOYSA-N 3,5-dichloro-n-[(1-ethylpyrrolidin-2-yl)methyl]-2-phenylmethoxybenzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(Cl)=CC(Cl)=C1OCC1=CC=CC=C1 NSHCYKGCMPCBBA-UHFFFAOYSA-N 0.000 description 1
- KJBUBVMOTCYBPX-UHFFFAOYSA-N 3,5-dichloro-n-[2-(diethylamino)ethyl]-2-methoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=CC(Cl)=C1OC KJBUBVMOTCYBPX-UHFFFAOYSA-N 0.000 description 1
- BVSXVVJPFIZJAT-UHFFFAOYSA-N 3,5-dichloro-n-[2-(diethylamino)ethyl]-2-phenylmethoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=CC(Cl)=C1OCC1=CC=CC=C1 BVSXVVJPFIZJAT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000223503 Platysma Species 0.000 description 1
- 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 1
- 206010044565 Tremor Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PIQVDUKEQYOJNR-VZXSFKIWSA-N cocaine hydrochloride Chemical compound [Cl-].O([C@H]1C[C@@H]2CC[C@@H]([NH+]2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 PIQVDUKEQYOJNR-VZXSFKIWSA-N 0.000 description 1
- 229960003771 cocaine hydrochloride Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000010907 mechanical stirring Methods 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
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 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
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000000431 third toe Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR101328A FR6209M (xx) | 1967-04-03 | 1967-04-03 | |
| FR111808A FR1535586A (fr) | 1967-04-03 | 1967-06-23 | Nouveaux 2-benzyloxy benzamides et leur procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123720B true NO123720B (xx) | 1972-01-03 |
Family
ID=26175282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1264/68A NO123720B (xx) | 1967-04-03 | 1968-04-02 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3594417A (xx) |
| BE (1) | BE711602A (xx) |
| BG (1) | BG15876A3 (xx) |
| CH (1) | CH487120A (xx) |
| CS (1) | CS156416B2 (xx) |
| DE (1) | DE1695835C3 (xx) |
| DK (1) | DK124944B (xx) |
| ES (1) | ES351470A1 (xx) |
| FI (1) | FI48182C (xx) |
| FR (2) | FR6209M (xx) |
| GB (1) | GB1187514A (xx) |
| IE (1) | IE31997B1 (xx) |
| IL (1) | IL29694A (xx) |
| MC (1) | MC706A1 (xx) |
| NL (1) | NL139237B (xx) |
| NO (1) | NO123720B (xx) |
| OA (1) | OA02773A (xx) |
| SE (1) | SE372008B (xx) |
| YU (1) | YU32538B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005209A (en) * | 1974-04-01 | 1977-01-25 | Riker Laboratories, Inc. | Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides |
| US3900481A (en) * | 1974-04-01 | 1975-08-19 | Riker Laboratories Inc | Derivatives of pyrrolidine and piperidine |
| US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
| US5011992A (en) * | 1984-06-28 | 1991-04-30 | Bristol-Myers Squibb Company | Pharmacologically active substituted benzamides |
-
1967
- 1967-04-03 FR FR101328A patent/FR6209M/fr not_active Expired
- 1967-06-23 FR FR111808A patent/FR1535586A/fr not_active Expired
-
1968
- 1968-02-23 DE DE1695835A patent/DE1695835C3/de not_active Expired
- 1968-03-04 BE BE711602D patent/BE711602A/xx not_active IP Right Cessation
- 1968-03-11 ES ES351470A patent/ES351470A1/es not_active Expired
- 1968-03-12 MC MC752A patent/MC706A1/xx unknown
- 1968-03-16 OA OA53220A patent/OA02773A/xx unknown
- 1968-03-21 US US714795A patent/US3594417A/en not_active Expired - Lifetime
- 1968-03-26 IL IL29694A patent/IL29694A/xx unknown
- 1968-03-26 IE IE348/68A patent/IE31997B1/xx unknown
- 1968-03-27 YU YU0696/68A patent/YU32538B/xx unknown
- 1968-03-28 BG BG009702A patent/BG15876A3/bg unknown
- 1968-03-28 FI FI680870A patent/FI48182C/fi active
- 1968-03-29 CH CH467368A patent/CH487120A/fr not_active IP Right Cessation
- 1968-04-01 SE SE6804282A patent/SE372008B/xx unknown
- 1968-04-01 NL NL686804548A patent/NL139237B/xx not_active IP Right Cessation
- 1968-04-02 GB GB05840/68A patent/GB1187514A/en not_active Expired
- 1968-04-02 NO NO1264/68A patent/NO123720B/no unknown
- 1968-04-02 DK DK143168AA patent/DK124944B/da not_active IP Right Cessation
- 1968-04-03 CS CS249968A patent/CS156416B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1187514A (en) | 1970-04-08 |
| NL139237B (nl) | 1973-07-16 |
| FI48182C (fi) | 1974-07-10 |
| DE1695835B2 (de) | 1974-09-26 |
| DE1695835C3 (de) | 1975-05-22 |
| OA02773A (fr) | 1970-12-15 |
| ES351470A1 (es) | 1969-12-01 |
| CH487120A (fr) | 1970-03-15 |
| IE31997L (en) | 1968-10-03 |
| MC706A1 (fr) | 1968-12-17 |
| CS156416B2 (xx) | 1974-07-24 |
| US3594417A (en) | 1971-07-20 |
| IE31997B1 (en) | 1973-03-07 |
| BE711602A (xx) | 1968-09-04 |
| DK124944B (da) | 1972-12-11 |
| SE372008B (xx) | 1974-12-09 |
| YU32538B (en) | 1975-02-28 |
| FR1535586A (fr) | 1968-08-09 |
| YU69668A (en) | 1974-08-31 |
| FI48182B (xx) | 1974-04-01 |
| FR6209M (xx) | 1968-07-29 |
| IL29694A (en) | 1972-08-30 |
| NL6804548A (xx) | 1968-10-04 |
| DE1695835A1 (de) | 1972-03-09 |
| BG15876A3 (bg) | 1972-04-12 |
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