NO133200B - - Google Patents

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Info

Publication number: NO133200B
Authority: NO; Norway
Prior art keywords: cis; salts; acid; solution; mol
Prior art date: 1967-10-30

Application number

NO4276/68A

Other languages

English (en)

Norwegian (no)

Other versions

NO133200C (de

Inventor

B G Christensen

W J Leanza

T R Beattie

Original Assignee

Merck & Co Inc

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.)

1967-10-30

Filing date

1968-10-29

Publication date

1975-12-15

1968-10-29 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1975-12-15 Publication of NO133200B publication Critical patent/NO133200B/no

1976-03-24 Publication of NO133200C publication Critical patent/NO133200C/no

Links

150000003839 salts Chemical class 0.000 claims description 27
XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical group C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 8
230000000844 anti-bacterial effect Effects 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
-1 monoalkylamines Chemical class 0.000 description 15
239000000243 solution Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
YYTYLIVWHBVGKW-UHFFFAOYSA-N 1-[butoxy(prop-1-ynyl)phosphoryl]oxybutane Chemical compound C(CCC)OP(OCCCC)(=O)C#CC YYTYLIVWHBVGKW-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
244000052616 bacterial pathogen Species 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
JYDBWTLMEMXTBB-UHFFFAOYSA-N 1-[butoxy-[(Z)-prop-1-enyl]phosphoryl]oxybutane Chemical compound C(CCC)OP(OCCCC)(=O)C=C/C JYDBWTLMEMXTBB-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229940046892 lead acetate Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003973 paint Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
241000607142 Salmonella Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DXMAARCZJITWJZ-UHFFFAOYSA-L [Mg+2].[Br-].[Br-].CC#C Chemical compound [Mg+2].[Br-].[Br-].CC#C DXMAARCZJITWJZ-UHFFFAOYSA-L 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
244000005700 microbiome Species 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
CQPJLZWBXXBTJA-UHFFFAOYSA-N prop-1-ynylphosphonic acid Chemical class CC#CP(O)(O)=O CQPJLZWBXXBTJA-UHFFFAOYSA-N 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
ZJEHRMYJNACSLL-UHFFFAOYSA-N 1-[butoxy(chloro)phosphoryl]oxybutane Chemical compound CCCCOP(Cl)(=O)OCCCC ZJEHRMYJNACSLL-UHFFFAOYSA-N 0.000 description 1
LDVWNVNTGFDILM-UHFFFAOYSA-N 1-di(propan-2-yloxy)phosphorylprop-1-yne Chemical compound CC#CP(=O)(OC(C)C)OC(C)C LDVWNVNTGFDILM-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
GUFGWNUUDBGEGH-UHFFFAOYSA-N 2-[chloro(propan-2-yloxy)phosphoryl]oxypropane Chemical compound CC(C)OP(Cl)(=O)OC(C)C GUFGWNUUDBGEGH-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
RHHUYYMDAHUVSI-UHFFFAOYSA-N C(C)(C)OP(OC(C)C)(=O)C=C/C Chemical compound C(C)(C)OP(OC(C)C)(=O)C=C/C RHHUYYMDAHUVSI-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
102000007327 Protamines Human genes 0.000 description 1
108010007568 Protamines Proteins 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
241000607683 Salmonella enterica subsp. enterica serovar Pullorum Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
YYYYLWPWZWOIMP-UHFFFAOYSA-L [Na+].[Na+].OP(O)=O.[O-]P([O-])=O Chemical compound [Na+].[Na+].OP(O)=O.[O-]P([O-])=O YYYYLWPWZWOIMP-UHFFFAOYSA-L 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
125000005265 dialkylamine group Chemical class 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical class C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
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229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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239000000463 material Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
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150000004706 metal oxides Chemical class 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 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
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
229940048914 protamine Drugs 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000005270 trialkylamine group Chemical class 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)

NO4276/68A 1967-10-30 1968-10-29 NO133200C (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US67920367A	1967-10-30	1967-10-30
US72942068A	1968-05-15	1968-05-15

Publications (2)

Publication Number	Publication Date
NO133200B true NO133200B (de)	1975-12-15
NO133200C NO133200C (de)	1976-03-24

Family

ID=27102173

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO4276/68A NO133200C (de)	1967-10-30	1968-10-29

Country Status (15)

Country	Link
AT (1)	AT292731B (de)
BE (1)	BE723071A (de)
CH (1)	CH531012A (de)
DK (1)	DK132585C (de)
ES (1)	ES359538A1 (de)
FI (1)	FI51357C (de)
FR (1)	FR1592151A (de)
GB (1)	GB1239988A (de)
IE (1)	IE32525B1 (de)
IL (1)	IL30902A0 (de)
LU (1)	LU57182A1 (de)
MT (1)	MTP579B (de)
NL (1)	NL6814978A (de)
NO (1)	NO133200C (de)
SE (1)	SE369910B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA774977B (en) *	1976-09-06	1978-06-28	Sab Soc Etudes Applic Biolog	Process for the preparation of 1,2-expoxypropyl-phosphonic acid derivatives
EP2270021A1 (de)	2009-06-18	2011-01-05	Centre National de la Recherche Scientifique	Phosphonatsynthone zur Synthese von Phosphonat-Derivaten mit besserer Bioverfügbarkeit

1968
- 1968-10-18 NL NL6814978A patent/NL6814978A/xx unknown
- 1968-10-20 IL IL30902A patent/IL30902A0/xx unknown
- 1968-10-21 IE IE1257/68A patent/IE32525B1/xx unknown
- 1968-10-21 CH CH1569868A patent/CH531012A/de not_active IP Right Cessation
- 1968-10-24 GB GB50636/68A patent/GB1239988A/en not_active Expired
- 1968-10-25 ES ES359538A patent/ES359538A1/es not_active Expired
- 1968-10-29 NO NO4276/68A patent/NO133200C/no unknown
- 1968-10-29 LU LU57182D patent/LU57182A1/xx unknown
- 1968-10-29 BE BE723071D patent/BE723071A/xx unknown
- 1968-10-29 DK DK521968A patent/DK132585C/da active
- 1968-10-29 SE SE14617/68A patent/SE369910B/xx unknown
- 1968-10-29 FI FI683065A patent/FI51357C/fi active
- 1968-10-30 MT MT579A patent/MTP579B/xx unknown
- 1968-10-30 FR FR1592151D patent/FR1592151A/fr not_active Expired
- 1968-10-30 AT AT1055368A patent/AT292731B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK132585C (da)	1976-05-31
DK132585B (da)	1976-01-05
ES359538A1 (es)	1970-08-16
IE32525B1 (en)	1973-09-05
SE369910B (de)	1974-09-23
IL30902A0 (en)	1969-02-27
CH531012A (de)	1972-11-30
GB1239988A (en)	1971-07-21
DE1805677A1 (de)	1969-12-11
NO133200C (de)	1976-03-24
LU57182A1 (de)	1969-05-16
AT292731B (de)	1971-09-10
FI51357B (de)	1976-08-31
MTP579B (en)	1969-10-13
IE32525L (en)	1969-04-30
FI51357C (fi)	1976-12-10
NL6814978A (de)	1969-05-02
BE723071A (de)	1969-04-29
FR1592151A (de)	1970-05-11

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DE1924085A1 (de)	1970-01-15	Verfahren zum Zerlegen von Enantiomerengemischen von (cis-1,2-Epoxypropyl)-phosphonsaeurederivaten
NO141090B (no)	1979-10-01	N-fosfonmetylglyciner for anvendelse som herbicid og/eller fytotoksisk middel
IL24464A (en)	1969-09-25	Benzimidazole compounds,their preparation,and physiologically active compositions containing them
JPS5823672A (ja)	1983-02-12	新規なイミダゾリル誘導体およびその塩の製法
DE1468341A1 (de)	1969-05-22	Dibenzocycloheptan- und -hepten-Verbindungen und Verfahren zu ihrer Herstellung
DD156369A5 (de)	1982-08-18	Herstellung von rechtsdrehenden 5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3b]-indolen
CA1102329A (en)	1981-06-02	Process for the preparation of new therapeutically useful isoquinoline and quinazoline derivatives
NO133200B (de)	1975-12-15
US2645594A (en)	1953-07-14	Antiseptic acridane compounds
EP0371406B1 (de)	1993-08-04	Oxyalkylierte quaternäre Ammoniumverbindungen, Verfahren zu deren Herstellung und diese enthaltende Pflanzenwachstumsregulatoren
FR2694558A1 (fr)	1994-02-11	Monohydrate du sel disodique de l'acide 4-chlorophénylthiométhylène bisphosphonique, sa préparation, les compositions pharmaceutiques en contenant.
EP0112939B1 (de)	1986-09-17	Pentacycloundecan Derivate, Verfahren zu ihrer Herstellung, und diese enthaltende pharmazeutische Zusammensetzungen
SU506296A3 (ru)	1976-03-05	Способ получени 2-формил-3-карбонамидохиноксалин-ди- -окисей
US3929840A (en)	1975-12-30	Labile esters of ({31 )(cis-1,2-epoxypropyl)phosphonic
US3849482A (en)	1974-11-19	Amine salts of cis-propenylphosphonic acid
SU1456017A3 (ru)	1989-01-30	Способ получени двухъ дерных пиразолидинонов
WO1983002610A1 (en)	1983-08-04	Derivatives of 3,3-dialkyl-indolin and of 3,3-alkylene-indolin, method for producing them and pharmaceutical preparations containing them
US3189429A (en)	1965-06-15	Method of controlling plant growth
US3597451A (en)	1971-08-03	Process for the preparation of (+) cis-1,2-epoxypropyl)-phosphonic acid and derivatives
SU1450727A3 (ru)	1989-01-07	Способ регулировани роста зерновых культур
US2757196A (en)	1956-07-31	L-3-(2-propynylthio) alanine
DE1005058B (de)	1957-03-28	Verfahren zur Herstellung von O, O-Dialkylthiol- bzw. -thiolthionophosphorsaeureestern
DE1924104A1 (de)	1970-01-15	Verfahren zur Herstellung substituierter Propylphosphonsaeureester
US2844596A (en)	1958-07-22	Diphthalides