NO121875B - - Google Patents

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Publication number: NO121875B
Authority: NO; Norway
Prior art keywords: chloroform; amino; morpholine; acid; solution
Prior art date: 1965-08-11

Application number

NO164160A

Other languages

English (en)

Norwegian (no)

Inventor

J Birchall

Original Assignee

Ici Ltd

Priority date (The priority date 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 date listed.)

1965-08-11

Filing date

1966-08-03

Publication date

1971-04-19

1966-08-03 Application filed by Ici Ltd filed Critical Ici Ltd

1971-04-19 Publication of NO121875B publication Critical patent/NO121875B/no

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)

NO164160A 1965-08-11 1966-08-03 NO121875B (ru)

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 (ru)	1971-04-19

Family

ID=10364857

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO164160A NO121875B (ru)	1965-08-11	1966-08-03

Country Status (10)

Country	Link
US (1)	US3484372A (ru)
AT (1)	AT267332B (ru)
BE (1)	BE685425A (ru)
CH (1)	CH479315A (ru)
DE (1)	DE1546503B1 (ru)
FI (1)	FI51282C (ru)
GB (1)	GB1118215A (ru)
NL (1)	NL6611243A (ru)
NO (1)	NO121875B (ru)
SE (1)	SE344881B (ru)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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 (ru) *	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
CA1303300C (en) *	1986-10-25	1992-06-16	Derek A. Thacker	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
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
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
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE345535C (ru) *
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 (ru) *	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 CH CH1161966A patent/CH479315A/de not_active IP Right Cessation
- 1966-08-11 DE DE19661546503 patent/DE1546503B1/de not_active Withdrawn
- 1966-08-11 FI FI662095A patent/FI51282C/fi active
- 1966-08-11 BE BE685425D patent/BE685425A/xx unknown

Also Published As

Publication number	Publication date
BE685425A (ru)	1967-02-13
NL6611243A (ru)	1967-02-13
FI51282B (ru)	1976-08-31
FI51282C (fi)	1976-12-10
US3484372A (en)	1969-12-16
DE1546503B1 (de)	1970-07-09
GB1118215A (en)	1968-06-26
CH479315A (de)	1969-10-15
SE344881B (ru)	1972-05-08
AT267332B (de)	1968-12-27

Publication	Publication Date	Title
NO121875B (ru)	1971-04-19
NO155805B (no)	1987-02-23	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter.
US4289772A (en)	1981-09-15	1-Piperidinophthalazines as cardiac stimulants
PT100352B (pt)	1999-06-30	Aminas heterociclicas nomeadamente derivadas de piperazina, uteis na terapia da asma e das inflamacoes do tract0 respiratorio
US2870145A (en)	1959-01-20	Therapeutic agents
KR20080066925A (ko)	2008-07-17	항말라리아 제제로서 피페라진 유도체
US3706750A (en)	1972-12-19	Pyrrylaminoketone derivatives
US2861072A (en)	1958-11-18	Preparation of piperazine derivatives
CS228910B2 (en)	1984-05-14	Method of preparing new substituted alkyleneiminophenylalkyl amides of phenylalkane carboxylic acids
US2826578A (en)	1958-03-11	Therapeutic agents
NO169961B (no)	1992-05-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive piperaziner
Howard et al.	1953	Piperazines. II. 1-Heterocyclicpiperazines and 1-Hetero-Cyclic-4-Carbethoxypiperazines
NO124430B (ru)	1972-04-17
US2555353A (en)	1951-06-05	3-tertiaryaminoalkyl-2-pyrrolidones and process for preparing same and related products
US3562276A (en)	1971-02-09	Diarylcyclopropane piperazides possessing enhanced antihistaminic,antiserotoninic and antiexudative activity
US2679501A (en)	1954-05-25	Amino derivatives of 2-substituted-4-tert. butylphenol ethers
AU682428B2 (en)	1997-10-02	New substituted sulphonamides, a process for their preparation and pharmaceutical compositions containing them
US4166852A (en)	1979-09-04	Piperazino-pyrimidines and their use as spasmolytic agents
US2822391A (en)	1958-02-04	Conhj
NO793473L (no)	1976-07-21	Fremgangsmaate til fremstilling av terapeutisk virksomme fenylalkylaminer
US2555354A (en)	1951-06-05	1-aliphatic-3, 3-diphenyl-2-pyrrolidones and process for preparing same and related products
US2793212A (en)	1957-05-21	Substituted benzamidopiperidinopropanes
US3712893A (en)	1973-01-23	Butyl-piperazine derivatives
DK169328B1 (da)	1994-10-10	Indolcarboxamidderivater, deres fremstilling samt farmaceutiske præparater med indhold deraf
SK3962001A3 (en)	2001-10-08	Benzoylguanidine derivatives with advantageous properties, method for producing them and their use in the production of medicaments