NO121875B - - Google Patents
Download PDFInfo
- Publication number
- NO121875B NO121875B NO164160A NO16416066A NO121875B NO 121875 B NO121875 B NO 121875B NO 164160 A NO164160 A NO 164160A NO 16416066 A NO16416066 A NO 16416066A NO 121875 B NO121875 B NO 121875B
- Authority
- NO
- Norway
- Prior art keywords
- chloroform
- amino
- morpholine
- acid
- solution
- Prior art date
Links
- -1 3,4,5-trimethoxybenzoyl halide Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 3
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 claims description 2
- AWABQFFPMULPED-UHFFFAOYSA-N 1-n-benzyl-2-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1NCC1=CC=CC=C1 AWABQFFPMULPED-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- BWQFDXJPBCPENW-UHFFFAOYSA-N n-benzyl-4-piperidin-1-ylaniline Chemical compound C=1C=CC=CC=1CNC(C=C1)=CC=C1N1CCCCC1 BWQFDXJPBCPENW-UHFFFAOYSA-N 0.000 claims description 2
- LCPCCZIHDCGBGU-UHFFFAOYSA-N n-methyl-4-morpholin-4-ylaniline Chemical compound C1=CC(NC)=CC=C1N1CCOCC1 LCPCCZIHDCGBGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 2
- AJZPMIZIBQXAOS-UHFFFAOYSA-N 2-(4-benzylmorpholin-3-yl)ethanamine Chemical compound NCCC1COCCN1CC1=CC=CC=C1 AJZPMIZIBQXAOS-UHFFFAOYSA-N 0.000 claims 1
- PXYUJKLVETYYJO-UHFFFAOYSA-N 2-(4-methylmorpholin-3-yl)ethanamine Chemical compound CN1CCOCC1CCN PXYUJKLVETYYJO-UHFFFAOYSA-N 0.000 claims 1
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 5
- CVWQXKSBPHOMGQ-UHFFFAOYSA-N Cl.COC=1C=C(C(=O)NC2=CC=C(N(C)C)C=C2)C=C(C1OC)OC Chemical compound Cl.COC=1C=C(C(=O)NC2=CC=C(N(C)C)C=C2)C=C(C1OC)OC CVWQXKSBPHOMGQ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- GGNMTJKRHHLJHH-UHFFFAOYSA-N Trimethylaethergallussaeure-amid Natural products COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229940125723 sedative agent Drugs 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WJSSEQZVGHKBLX-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(3-morpholin-4-ylpropyl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCCCN2CCOCC2)=C1 WJSSEQZVGHKBLX-UHFFFAOYSA-N 0.000 description 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- AVFGUWZHRCOPMQ-UHFFFAOYSA-N N-[4-(dimethylamino)phenyl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=CC(=CC=2)N(C)C)=C1 AVFGUWZHRCOPMQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 2
- 229960002456 hexobarbital Drugs 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ISAXYRXEJSEHRF-UHFFFAOYSA-N n-[5-(diethylamino)pentan-2-yl]-3,4,5-trimethoxybenzamide Chemical compound CCN(CC)CCCC(C)NC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ISAXYRXEJSEHRF-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 1
- GAZNVVBKELWTBC-UHFFFAOYSA-N 2,3,4-trimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1OC GAZNVVBKELWTBC-UHFFFAOYSA-N 0.000 description 1
- GLOJLKCUVTZRFO-UHFFFAOYSA-N 2-(2,6-dimethylmorpholin-4-yl)ethanamine Chemical compound CC1CN(CCN)CC(C)O1 GLOJLKCUVTZRFO-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- AIQNHPWJWHVNQU-UHFFFAOYSA-N 3,4,5-triethoxybenzamide Chemical class CCOC1=CC(C(N)=O)=CC(OCC)=C1OCC AIQNHPWJWHVNQU-UHFFFAOYSA-N 0.000 description 1
- JUICNMLFNLOFMZ-UHFFFAOYSA-N 3,4,5-triethoxybenzoyl chloride Chemical compound CCOC1=CC(C(Cl)=O)=CC(OCC)=C1OCC JUICNMLFNLOFMZ-UHFFFAOYSA-N 0.000 description 1
- LCXRLQAEXIFYPE-UHFFFAOYSA-N 3,4,5-trihexoxybenzoyl chloride Chemical compound CCCCCCOC1=CC(C(Cl)=O)=CC(OCCCCCC)=C1OCCCCCC LCXRLQAEXIFYPE-UHFFFAOYSA-N 0.000 description 1
- SLSYXAIGCIBUIJ-UHFFFAOYSA-N 3,4,5-trimethoxy-N-(4-morpholin-4-ium-4-ylphenyl)benzamide chloride Chemical compound Cl.O1CCN(CC1)C1=CC=C(NC(C2=CC(=C(C(=C2)OC)OC)OC)=O)C=C1 SLSYXAIGCIBUIJ-UHFFFAOYSA-N 0.000 description 1
- HCTBOZOAFWFRDH-UHFFFAOYSA-N 3-morpholin-4-ylpropan-1-amine;hydrochloride Chemical compound Cl.NCCCN1CCOCC1 HCTBOZOAFWFRDH-UHFFFAOYSA-N 0.000 description 1
- NXKRSMDVDRFSBV-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)butan-1-amine Chemical compound CN1CCN(CCCCN)CC1 NXKRSMDVDRFSBV-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- KTCOBQQVDFMACK-UHFFFAOYSA-N C(CCCCC)N(CCCCCCNCC)CCCCCC Chemical compound C(CCCCC)N(CCCCCCNCC)CCCCCC KTCOBQQVDFMACK-UHFFFAOYSA-N 0.000 description 1
- IPJHICAFFNWIDS-UHFFFAOYSA-N C(CCCCC)OC=1C=C(C(=O)N)C=C(C=1OCCCCCC)OCCCCCC Chemical class C(CCCCC)OC=1C=C(C(=O)N)C=C(C=1OCCCCCC)OCCCCCC IPJHICAFFNWIDS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- KTWNIUBGGFBRKH-UHFFFAOYSA-N [4-(dimethylamino)phenyl]azanium;chloride Chemical compound Cl.CN(C)C1=CC=C(N)C=C1 KTWNIUBGGFBRKH-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 229960004543 anhydrous citric acid Drugs 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UVWQYWHKTZABSO-ILADVTTDSA-N de voachalotinol Chemical compound CN1C2=CC=CC=C2C(C[C@H]2[C@@H]3CO)=C1[C@H]1N2C/C(=C/C)[C@@H]3C1 UVWQYWHKTZABSO-ILADVTTDSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004970 emotional disturbance Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GDLKYSDWWYFIMQ-UHFFFAOYSA-N n',n'-dihexylethane-1,2-diamine Chemical compound CCCCCCN(CCN)CCCCCC GDLKYSDWWYFIMQ-UHFFFAOYSA-N 0.000 description 1
- DUEYZRNFSPONAG-UHFFFAOYSA-N n',n'-dipropylpentane-1,5-diamine Chemical compound CCCN(CCC)CCCCCN DUEYZRNFSPONAG-UHFFFAOYSA-N 0.000 description 1
- HUQLOABSMDKQBW-UHFFFAOYSA-N n'-benzyl-n-methylethane-1,2-diamine Chemical compound CNCCNCC1=CC=CC=C1 HUQLOABSMDKQBW-UHFFFAOYSA-N 0.000 description 1
- KKVWZMSIFJYBPO-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylethyl)butan-1-amine Chemical compound CCCCNCCN1CCCC1 KKVWZMSIFJYBPO-UHFFFAOYSA-N 0.000 description 1
- MSFAUJOUPQMLNF-UHFFFAOYSA-N n-benzyl-2-morpholin-4-ylethanamine Chemical compound C=1C=CC=CC=1CNCCN1CCOCC1 MSFAUJOUPQMLNF-UHFFFAOYSA-N 0.000 description 1
- WWXPJKGWWPWBTB-UHFFFAOYSA-N n-methyl-2-morpholin-4-ylethanamine Chemical compound CNCCN1CCOCC1 WWXPJKGWWPWBTB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0007—Solid extinguishing substances
- A62D1/0014—Powders; Granules
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Fireproofing Substances (AREA)
- Fire-Extinguishing Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34374/65A GB1118215A (en) | 1965-08-11 | 1965-08-11 | Fire-extinguishing compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121875B true NO121875B (de) | 1971-04-19 |
Family
ID=10364857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO164160A NO121875B (de) | 1965-08-11 | 1966-08-03 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3484372A (de) |
| AT (1) | AT267332B (de) |
| BE (1) | BE685425A (de) |
| CH (1) | CH479315A (de) |
| DE (1) | DE1546503B1 (de) |
| FI (1) | FI51282C (de) |
| GB (1) | GB1118215A (de) |
| NL (1) | NL6611243A (de) |
| NO (1) | NO121875B (de) |
| SE (1) | SE344881B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536620A (en) * | 1966-11-03 | 1970-10-27 | Ici Ltd | Fire-extinguishing compositions comprising the reaction products of urea and a bicarbonate,carbonate or hydroxide of sodium or potassium |
| GB1229021A (de) * | 1968-02-16 | 1971-04-21 | ||
| US3608641A (en) * | 1968-03-01 | 1971-09-28 | Ici Ltd | Preparation of fire-extinguishing material by heating dicyandiamide with alkali metal carbonates or bicarbonates |
| GB1495199A (en) * | 1975-11-14 | 1977-12-14 | Ici Ltd | Process for producing fire-extinguishing compositions |
| US4908160A (en) * | 1986-10-25 | 1990-03-13 | Tag Investments, Inc. | Fire retardant composition |
| US4842611A (en) * | 1987-12-01 | 1989-06-27 | Huffman Daniel D | Flame retardant compositions and process |
| US4888136A (en) * | 1988-05-02 | 1989-12-19 | Witco Corporation | New flame retardant compositions of matter and cellulosic products containing same |
| US5820776A (en) * | 1997-05-16 | 1998-10-13 | Ansul, Incorporated | Combination of a novel fire extinguishing composition employing a eutectic salt mixture and water and a method of using same to extinguish fires |
| DE102006056661A1 (de) * | 2006-11-29 | 2008-06-05 | Union Marketing Gmbh | Flammhemmende Ausrüstung, ihre Herstellung, Aufbringung auf brennbare Produkte und Verwendung |
| DE102009053186A1 (de) | 2009-11-08 | 2011-05-12 | Caldic Deutschland Chemie Bv | Feuerlöschmittel, insbesondere Trockenpulvermischungen, Verfahren zur deren Herstellung und Verwendung |
| US11395931B2 (en) | 2017-12-02 | 2022-07-26 | Mighty Fire Breaker Llc | Method of and system network for managing the application of fire and smoke inhibiting compositions on ground surfaces before the incidence of wild-fires, and also thereafter, upon smoldering ambers and ashes to reduce smoke and suppress fire re-ignition |
| US10653904B2 (en) | 2017-12-02 | 2020-05-19 | M-Fire Holdings, Llc | Methods of suppressing wild fires raging across regions of land in the direction of prevailing winds by forming anti-fire (AF) chemical fire-breaking systems using environmentally clean anti-fire (AF) liquid spray applied using GPS-tracking techniques |
| US11865390B2 (en) | 2017-12-03 | 2024-01-09 | Mighty Fire Breaker Llc | Environmentally-clean water-based fire inhibiting biochemical compositions, and methods of and apparatus for applying the same to protect property against wildfire |
| US11865394B2 (en) | 2017-12-03 | 2024-01-09 | Mighty Fire Breaker Llc | Environmentally-clean biodegradable water-based concentrates for producing fire inhibiting and fire extinguishing liquids for fighting class A and class B fires |
| US11826592B2 (en) | 2018-01-09 | 2023-11-28 | Mighty Fire Breaker Llc | Process of forming strategic chemical-type wildfire breaks on ground surfaces to proactively prevent fire ignition and flame spread, and reduce the production of smoke in the presence of a wild fire |
| US11911643B2 (en) | 2021-02-04 | 2024-02-27 | Mighty Fire Breaker Llc | Environmentally-clean fire inhibiting and extinguishing compositions and products for sorbing flammable liquids while inhibiting ignition and extinguishing fire |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE345535C (de) * | ||||
| DE485400C (de) * | 1925-07-31 | 1929-10-31 | Edgar Fuchs Dr | Verfahren zur Herstellung von Trockenloeschmitteln |
| US1895692A (en) * | 1928-02-27 | 1933-01-31 | Fyr Fyter Co | Fire extinguishing composition |
| FR838638A (fr) * | 1937-11-19 | 1939-03-10 | D App De Prot Soc Ind | Procédé de préparation de solutions aqueuses à bas point de congélation |
| DE1130705B (de) * | 1957-02-09 | 1962-05-30 | Total Foerstner & Co | Trockenloeschpulver |
| NL98618C (de) * | 1958-01-22 | |||
| US2935471A (en) * | 1958-09-10 | 1960-05-03 | Du Pont | Flame retardant composition |
-
1965
- 1965-08-11 GB GB34374/65A patent/GB1118215A/en not_active Expired
-
1966
- 1966-07-11 SE SE10892/66*A patent/SE344881B/xx unknown
- 1966-08-01 US US569046A patent/US3484372A/en not_active Expired - Lifetime
- 1966-08-03 NO NO164160A patent/NO121875B/no unknown
- 1966-08-10 NL NL6611243A patent/NL6611243A/xx unknown
- 1966-08-11 AT AT768866A patent/AT267332B/de active
- 1966-08-11 DE DE19661546503 patent/DE1546503B1/de not_active Withdrawn
- 1966-08-11 BE BE685425D patent/BE685425A/xx unknown
- 1966-08-11 FI FI662095A patent/FI51282C/fi active
- 1966-08-11 CH CH1161966A patent/CH479315A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1118215A (en) | 1968-06-26 |
| AT267332B (de) | 1968-12-27 |
| FI51282C (fi) | 1976-12-10 |
| BE685425A (de) | 1967-02-13 |
| FI51282B (de) | 1976-08-31 |
| DE1546503B1 (de) | 1970-07-09 |
| US3484372A (en) | 1969-12-16 |
| SE344881B (de) | 1972-05-08 |
| NL6611243A (de) | 1967-02-13 |
| CH479315A (de) | 1969-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO121875B (de) | ||
| NO155805B (no) | Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter. | |
| US4289772A (en) | 1-Piperidinophthalazines as cardiac stimulants | |
| PT100352B (pt) | Aminas heterociclicas nomeadamente derivadas de piperazina, uteis na terapia da asma e das inflamacoes do tract0 respiratorio | |
| NO144262B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk virksomme n-substituerte benzamidderivater | |
| NO122814B (de) | ||
| US2870145A (en) | Therapeutic agents | |
| KR20080066925A (ko) | 항말라리아 제제로서 피페라진 유도체 | |
| US3706750A (en) | Pyrrylaminoketone derivatives | |
| SK282751B6 (sk) | Benzoylguanidínové deriváty, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie | |
| US2826578A (en) | Therapeutic agents | |
| Howard et al. | Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines | |
| NO124430B (de) | ||
| US2555353A (en) | 3-tertiaryaminoalkyl-2-pyrrolidones and process for preparing same and related products | |
| US3562276A (en) | Diarylcyclopropane piperazides possessing enhanced antihistaminic,antiserotoninic and antiexudative activity | |
| US2679501A (en) | Amino derivatives of 2-substituted-4-tert. butylphenol ethers | |
| AU682428B2 (en) | New substituted sulphonamides, a process for their preparation and pharmaceutical compositions containing them | |
| US4166852A (en) | Piperazino-pyrimidines and their use as spasmolytic agents | |
| US2822391A (en) | Conhj | |
| NO793473L (no) | Fremgangsmaate til fremstilling av terapeutisk virksomme fenylalkylaminer | |
| US2555354A (en) | 1-aliphatic-3, 3-diphenyl-2-pyrrolidones and process for preparing same and related products | |
| US2793212A (en) | Substituted benzamidopiperidinopropanes | |
| JPS598260B2 (ja) | １０−アミノ−９、１０−ジヒドロフエナントレン誘導体およびその製造法 | |
| US3712893A (en) | Butyl-piperazine derivatives | |
| DK169328B1 (da) | Indolcarboxamidderivater, deres fremstilling samt farmaceutiske præparater med indhold deraf |