DEC0010600MA - - Google Patents
Info
- Publication number
- DEC0010600MA DEC0010600MA DEC0010600MA DE C0010600M A DEC0010600M A DE C0010600MA DE C0010600M A DEC0010600M A DE C0010600MA
- Authority
- DE
- Germany
- Prior art keywords
- cyclopentyl
- mol
- acid
- ether
- compounds
- 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.)
- Active
Links
- -1 bromine-substituted cyclopentyl acetic acid amides Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000001624 sedative effect Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KVESMOYKDNWRSD-UHFFFAOYSA-N 2-bromo-n-cyclopentylacetamide Chemical class BrCC(=O)NC1CCCC1 KVESMOYKDNWRSD-UHFFFAOYSA-N 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- NLFYPILXYRGBFK-UHFFFAOYSA-N 2-bromo-2-cyclopentylacetyl chloride Chemical compound ClC(=O)C(Br)C1CCCC1 NLFYPILXYRGBFK-UHFFFAOYSA-N 0.000 description 5
- KHMVXSQLPUNRCF-UHFFFAOYSA-N DL-Adalin Natural products C1CCC2CC(=O)CC1(CCCCC)N2 KHMVXSQLPUNRCF-UHFFFAOYSA-N 0.000 description 5
- OPNPQXLQERQBBV-UHFFFAOYSA-N carbromal Chemical compound CCC(Br)(CC)C(=O)NC(N)=O OPNPQXLQERQBBV-UHFFFAOYSA-N 0.000 description 5
- 239000000932 sedative agent Substances 0.000 description 5
- MUPJNXOZPQMJNR-UHFFFAOYSA-N 2-bromo-2-cyclopentylacetic acid Chemical compound OC(=O)C(Br)C1CCCC1 MUPJNXOZPQMJNR-UHFFFAOYSA-N 0.000 description 4
- QPCJKGBLHHHSDE-UHFFFAOYSA-N C1(CCCC1)C(C(=O)N)(Br)CCCC Chemical compound C1(CCCC1)C(C(=O)N)(Br)CCCC QPCJKGBLHHHSDE-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- YVOKPFHLJAJQAD-UHFFFAOYSA-N C1(CCCC1)C(C(=O)Cl)(Br)CCCC Chemical compound C1(CCCC1)C(C(=O)Cl)(Br)CCCC YVOKPFHLJAJQAD-UHFFFAOYSA-N 0.000 description 2
- BQAVURAVRZIGCG-UHFFFAOYSA-N C1(CCCC1)C(C(=O)O)(Br)CCCC Chemical compound C1(CCCC1)C(C(=O)O)(Br)CCCC BQAVURAVRZIGCG-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 229960005015 local anesthetics Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
- QGBAGJFSWPOCAT-UHFFFAOYSA-N 2-bromo-2-cyclopentylacetamide Chemical compound C1(CCCC1)C(C(=O)N)Br QGBAGJFSWPOCAT-UHFFFAOYSA-N 0.000 description 1
- LRAVOQZFSQRPTM-UHFFFAOYSA-N 2-cyclopentylhexanoic acid Chemical compound CCCCC(C(O)=O)C1CCCC1 LRAVOQZFSQRPTM-UHFFFAOYSA-N 0.000 description 1
- HWGYTXCOYRMFCM-UHFFFAOYSA-N C1(CCCC1)C(C(=O)N)(Br)CCC Chemical compound C1(CCCC1)C(C(=O)N)(Br)CCC HWGYTXCOYRMFCM-UHFFFAOYSA-N 0.000 description 1
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KKLWKXIAGLMYJV-UHFFFAOYSA-N N-butylbutan-1-amine hypochlorous acid Chemical compound OCl.CCCCNCCCC KKLWKXIAGLMYJV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GXRZIMHKGDIBEW-UHFFFAOYSA-N ethinamate Chemical compound NC(=O)OC1(C#C)CCCCC1 GXRZIMHKGDIBEW-UHFFFAOYSA-N 0.000 description 1
- 229960002209 ethinamate Drugs 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2700091C2 (enrdf_load_stackoverflow) | ||
| DE2203373B2 (de) | Neue 2- eckige klammer auf (2- alkylbenzofuran-3-yl)-methyl eckige klammer zu -delta hoch 2 -imidazoline | |
| DE2160148C2 (de) | Arzneimittel und bestimmte Sulfoxide als solche | |
| DE2047658B2 (de) | 2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| EP0104423B1 (de) | 2-Nitro-1,1-ethendiamine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE2006978B2 (de) | N- [H3-Trifluormethyl-phenyl)-propyl-(2)] -glycinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1445186C3 (de) | 3,3'-Di-2-imidazolin-2-yl-carbanilid | |
| DE965324C (de) | Verfahren zur Herstellung von bromsubstituierten Cyclopentylessigsaeureamiden | |
| EP0081748A2 (de) | Verfahren zur Herstellung von (-)-2-(1-(2,6-Dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en | |
| DEC0010600MA (enrdf_load_stackoverflow) | ||
| DE2462966C2 (de) | Derivate des 3-Amino-4-acetyl-5-methylpyrrols und diese enthaltende pharmazeutische Zubereitungen | |
| DE2313020A1 (de) | Antibakteriell wirksame hexamethylenbis-biguanide | |
| CH516593A (de) | Verfahren zur Herstellung von neuen Estern von a-Aminobenzyl-penicillin | |
| DE1177633B (de) | Verfahren zur Herstellung aminoalkylierter 9,10-Dihydroanthracene | |
| CH658653A5 (de) | Verfahren zur herstellung von pyrimidintrionderivaten. | |
| DE2609574B2 (de) | 1-(4-fluor-3-trifluormethylthio- phenyl)-piperazin, dessen salze, verfahren zu dessen herstellung und arzneimittel | |
| DE2304764A1 (de) | Benzoylphenylguanidine, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2031360A1 (de) | Neue cyclische Verbindungen und Ver fahren zu ihrer Herstellung | |
| DE1543859C3 (de) | N-Methyl- eckige Klammer auf beta-(m-trifluormethyl-phenyl) beta-methoxy eckige Klammer zu -äthylamin, dessen Säureadditionssalze und Verfahren zur Herstellung derselben sowie diese enthaltende Arzneimittel | |
| CH468979A (de) | Verfahren zur Herstellung von Benzolsulfonylharnstoffen | |
| DE2448602C3 (de) | N-Benzyl-2-[(m-trifluormethylthio) phenyl] -2-methoxy-äthylamin, Verfahren zu dessen Herstellung und diese Verbindung enthaltende Arzneimittel | |
| DE2538593C3 (de) | m-Trifluormethylthio-phenäthylaminderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1493902C3 (de) | N-(N-AcylaminoacyOaminoacetonitrile, Verfahren zu ihrer Herstellung und diese enthaltende Mittel | |
| DE2511645A1 (de) | Pyrrol- eckige klammer auf 3,4-d eckige klammer zu -pyrimidine und verfahren zu ihrer herstellung | |
| DE1518004C3 (de) | N-Carboxymethyl-2-(4-chlorphenoxy)· 2-methylpropionamid, Verfahren zu dessen Herstellung, und Arzneimittel, die diese Verbindung enthalten |