NO771770L - Fremgangsm}te til fremstilling av fosfonsyre - Google Patents

Fremgangsm}te til fremstilling av fosfonsyre

Info

Publication number: NO771770L
Authority: NO; Norway
Prior art keywords: acid; amino; hydrogen; general formula; group
Prior art date: 1976-05-21

Application number

NO771770A

Other languages

English (en)

Norwegian (no)

Inventor

John Grey Dingwall

Eric Keith Baylis

Colin Dennis Campbell

Original Assignee

Ciba Geigy Ag

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.)

1976-05-21

Filing date

1977-05-20

Publication date

1977-11-22

1977-05-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-11-22 Publication of NO771770L publication Critical patent/NO771770L/no

Links

238000000034 method Methods 0.000 title claims description 93
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 2
239000002253 acid Substances 0.000 claims description 113
150000001875 compounds Chemical class 0.000 claims description 53
-1 polymethylene chain Polymers 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 20
239000002585 base Substances 0.000 claims description 20
238000003776 cleavage reaction Methods 0.000 claims description 18
230000007017 scission Effects 0.000 claims description 18
150000007513 acids Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
230000003287 optical effect Effects 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 12
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
229910052805 deuterium Inorganic materials 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
DGSLPJDIFKVSIB-UHFFFAOYSA-N (1-azaniumyl-2-methylpropyl)-hydroxyphosphinate Chemical compound CC(C)C(N)P(O)(O)=O DGSLPJDIFKVSIB-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 claims description 5
UIQSKEDQPSEGAU-UHFFFAOYSA-N 1-Aminoethylphosphonic Acid Chemical compound CC(N)P(O)(O)=O UIQSKEDQPSEGAU-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
239000002262 Schiff base Substances 0.000 claims description 3
150000004753 Schiff bases Chemical class 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000005840 aryl radicals Chemical class 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
VMSRCTIIPRWCGJ-UHFFFAOYSA-N (1-aminocyclohexyl)phosphonic acid Chemical compound OP(=O)(O)C1(N)CCCCC1 VMSRCTIIPRWCGJ-UHFFFAOYSA-N 0.000 claims description 2
FBXFXDVQDQRPCE-UHFFFAOYSA-N (1-aminocyclopentyl)phosphonic acid Chemical compound OP(=O)(O)C1(N)CCCC1 FBXFXDVQDQRPCE-UHFFFAOYSA-N 0.000 claims description 2
GJYJYFHBOBUTBY-UHFFFAOYSA-N alpha-camphorene Chemical compound CC(C)=CCCC(=C)C1CCC(CCC=C(C)C)=CC1 GJYJYFHBOBUTBY-UHFFFAOYSA-N 0.000 claims description 2
150000003934 aromatic aldehydes Chemical class 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
159000000000 sodium salts Chemical class 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims 2
RVUUAGQILBTWHJ-UHFFFAOYSA-N (1-amino-2-hydroxyethyl)phosphonic acid Chemical compound OCC(N)P(O)(O)=O RVUUAGQILBTWHJ-UHFFFAOYSA-N 0.000 claims 1
NOQKPEWLSMCOFU-UHFFFAOYSA-N (1-amino-2-methylbutyl)phosphonic acid Chemical compound CCC(C)C(N)P(O)(O)=O NOQKPEWLSMCOFU-UHFFFAOYSA-N 0.000 claims 1
LWUPGGUBUSYFTG-UHFFFAOYSA-N (1-aminocyclohexa-2,4-dien-1-yl)methylphosphonic acid Chemical compound OP(=O)(O)CC1(N)CC=CC=C1 LWUPGGUBUSYFTG-UHFFFAOYSA-N 0.000 claims 1
FQCNOURLMNHAQN-UHFFFAOYSA-N (1-azaniumyl-2-phenylethyl)-hydroxyphosphinate Chemical compound OP(=O)(O)C(N)CC1=CC=CC=C1 FQCNOURLMNHAQN-UHFFFAOYSA-N 0.000 claims 1
HGCAUCAWEADMPM-UHFFFAOYSA-N (1-azaniumyl-3-methylbutyl)-hydroxyphosphinate Chemical compound CC(C)CC(N)P(O)(O)=O HGCAUCAWEADMPM-UHFFFAOYSA-N 0.000 claims 1
NANISUSRVMESCE-UHFFFAOYSA-N (2-amino-3-methylbutan-2-yl)phosphonic acid Chemical compound CC(C)C(C)(N)P(O)(O)=O NANISUSRVMESCE-UHFFFAOYSA-N 0.000 claims 1
UAEPDDGDPAPPHZ-UHFFFAOYSA-N 1-aminobutylphosphonic acid Chemical compound CCCC(N)P(O)(O)=O UAEPDDGDPAPPHZ-UHFFFAOYSA-N 0.000 claims 1
ICKNPJHUQGEMTH-UHFFFAOYSA-N 1-aminoheptylphosphonic acid Chemical compound CCCCCCC(N)P(O)(O)=O ICKNPJHUQGEMTH-UHFFFAOYSA-N 0.000 claims 1
NXTPDFMZKSLVRK-UHFFFAOYSA-N 1-aminopentylphosphonic acid Chemical compound CCCCC(N)P(O)(O)=O NXTPDFMZKSLVRK-UHFFFAOYSA-N 0.000 claims 1
DYGRPJWAYXRMQZ-UHFFFAOYSA-N 2-aminopropan-2-ylphosphonic acid Chemical compound CC(C)(N)P(O)(O)=O DYGRPJWAYXRMQZ-UHFFFAOYSA-N 0.000 claims 1
SODXFOVXZATGPJ-UHFFFAOYSA-N 4-amino-4-phosphonobutanoic acid Chemical compound OP(=O)(O)C(N)CCC(O)=O SODXFOVXZATGPJ-UHFFFAOYSA-N 0.000 claims 1
YREQAXDEXVNRIT-UHFFFAOYSA-N NC(CCC)P(O)(=S)O Chemical compound NC(CCC)P(O)(=S)O YREQAXDEXVNRIT-UHFFFAOYSA-N 0.000 claims 1
ZUEMQUDNGYLGGA-UHFFFAOYSA-N [1-amino-2-(1h-indol-3-yl)ethyl]phosphonic acid Chemical compound C1=CC=C2C(CC(N)P(O)(O)=O)=CNC2=C1 ZUEMQUDNGYLGGA-UHFFFAOYSA-N 0.000 claims 1
IKXXVDZMRIWEMJ-UHFFFAOYSA-N [1-amino-2-(3,4-dihydroxyphenyl)ethyl]phosphonic acid Chemical compound OP(=O)(O)C(N)CC1=CC=C(O)C(O)=C1 IKXXVDZMRIWEMJ-UHFFFAOYSA-N 0.000 claims 1
KKZFIJSLXCDYKY-UHFFFAOYSA-N [1-amino-2-(4-hydroxyphenyl)ethyl]phosphonic acid Chemical compound OP(=O)(O)C(N)CC1=CC=C(O)C=C1 KKZFIJSLXCDYKY-UHFFFAOYSA-N 0.000 claims 1
KQSZRFWCLKFQNU-UHFFFAOYSA-N [amino(1h-indol-3-yl)methyl]phosphonic acid Chemical compound C1=CC=C2C(C(N)P(O)(O)=O)=CNC2=C1 KQSZRFWCLKFQNU-UHFFFAOYSA-N 0.000 claims 1
OOGDWWCJEPHBDQ-UHFFFAOYSA-N [amino(cyclohexyl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)C1CCCCC1 OOGDWWCJEPHBDQ-UHFFFAOYSA-N 0.000 claims 1
AMJUOJFMVXAEDD-UHFFFAOYSA-N [amino(furan-2-yl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)C1=CC=CO1 AMJUOJFMVXAEDD-UHFFFAOYSA-N 0.000 claims 1
RWSKQIVCZOCSLL-UHFFFAOYSA-N [amino(thiophen-2-yl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)C1=CC=CS1 RWSKQIVCZOCSLL-UHFFFAOYSA-N 0.000 claims 1
QXOFDXPCBBHAHP-UHFFFAOYSA-N [amino-(2,4-dichlorophenyl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)C1=CC=C(Cl)C=C1Cl QXOFDXPCBBHAHP-UHFFFAOYSA-N 0.000 claims 1
FTESIVGLKQSQDC-UHFFFAOYSA-N [amino-(4-aminophenyl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)C1=CC=C(N)C=C1 FTESIVGLKQSQDC-UHFFFAOYSA-N 0.000 claims 1
UMXOHXMGOUBRHV-UHFFFAOYSA-N [amino-(4-methylphenyl)methyl]phosphonic acid Chemical compound CC1=CC=C(C(N)P(O)(O)=O)C=C1 UMXOHXMGOUBRHV-UHFFFAOYSA-N 0.000 claims 1
ZJZJSZIPEGOHEG-UHFFFAOYSA-N [amino-[4-(dimethylamino)phenyl]methyl]phosphonic acid Chemical compound CN(C)C1=CC=C(C(N)P(O)(O)=O)C=C1 ZJZJSZIPEGOHEG-UHFFFAOYSA-N 0.000 claims 1
239000002552 dosage form Substances 0.000 claims 1
238000002844 melting Methods 0.000 description 62
230000008018 melting Effects 0.000 description 62
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 56
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000007858 starting material Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000007787 solid Substances 0.000 description 21
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 19
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
239000013543 active substance Substances 0.000 description 12
NOYUXBZUSVICGL-UHFFFAOYSA-N n-benzhydryl-2-methylpropan-1-imine Chemical compound C=1C=CC=CC=1C(N=CC(C)C)C1=CC=CC=C1 NOYUXBZUSVICGL-UHFFFAOYSA-N 0.000 description 11
NRIVMXXOUOBRAG-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1 NRIVMXXOUOBRAG-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000008298 dragée Substances 0.000 description 7
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000003826 tablet Substances 0.000 description 6
OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
239000000969 carrier Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000000463 material Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000249 desinfective effect Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
239000001893 (2R)-2-methylbutanal Substances 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
LPCWMYHBLXLJJQ-UHFFFAOYSA-N 3-hexen-2-one Chemical compound CCC=CC(C)=O LPCWMYHBLXLJJQ-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
XUZICJHIIJCKQQ-ZDUSSCGKSA-N eclitasertib Chemical compound C(C1=CC=CC=C1)C=1NC(=NN=1)C(=O)N[C@@H]1C(N(C2=C(OC1)C=CC=N2)C)=O XUZICJHIIJCKQQ-ZDUSSCGKSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
BNNHGIVAWFZFIU-UHFFFAOYSA-N n-benzhydryl-2-methylbutan-1-imine Chemical compound C=1C=CC=CC=1C(N=CC(C)CC)C1=CC=CC=C1 BNNHGIVAWFZFIU-UHFFFAOYSA-N 0.000 description 1
RBDNYMZMECTVGV-UHFFFAOYSA-N n-benzyl-2-methylpropan-1-imine Chemical compound CC(C)C=NCC1=CC=CC=C1 RBDNYMZMECTVGV-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940100595 phenylacetaldehyde Drugs 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940081310 piperonal Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229960001462 sodium cyclamate Drugs 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
239000004758 synthetic textile Substances 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
239000002966 varnish Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO771770A 1976-05-21 1977-05-20 Fremgangsm}te til fremstilling av fosfonsyre NO771770L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB21000/76A GB1542938A (en)	1976-05-21	1976-05-21	Aminophosphonous acids and processes for their preparation

Publications (1)

Publication Number	Publication Date
NO771770L true NO771770L (no)	1977-11-22

Family

ID=10155485

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO771770A NO771770L (no)	1976-05-21	1977-05-20	Fremgangsm}te til fremstilling av fosfonsyre

Country Status (29)

Country	Link
US (1)	US4147780A (es)
JP (1)	JPS52151128A (es)
AR (2)	AR219077A1 (es)
AT (1)	AT350585B (es)
AU (1)	AU516592B2 (es)
BE (1)	BE854843A (es)
BG (2)	BG27905A3 (es)
CA (1)	CA1081241A (es)
CS (1)	CS202066B2 (es)
DD (1)	DD131751A5 (es)
DE (1)	DE2722162A1 (es)
DK (1)	DK221477A (es)
EG (1)	EG12688A (es)
ES (1)	ES458931A1 (es)
FI (1)	FI771602A (es)
FR (1)	FR2360601A1 (es)
GB (1)	GB1542938A (es)
IE (1)	IE44904B1 (es)
IL (1)	IL52127A0 (es)
NL (1)	NL7705602A (es)
NO (1)	NO771770L (es)
NZ (1)	NZ184166A (es)
OA (1)	OA05666A (es)
PH (1)	PH14170A (es)
PL (2)	PL106608B1 (es)
PT (1)	PT66581B (es)
SE (1)	SE7705886L (es)
SU (2)	SU805948A3 (es)
ZA (1)	ZA773017B (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2861609D1 (en) *	1977-11-19	1982-03-11	Ciba Geigy Ag	Methods of inhibiting plant and combating weeds using alpha-aminoalkanephosphonous acids
EP0002039A1 (en) *	1977-11-19	1979-05-30	Ciba-Geigy Ag	Phosphonous acid derivatives, processes for their preparation and their use in combating microorganisms
IL61985A0 (en) *	1980-02-01	1981-02-27	Sparamedica Ag	Phosphinic and phosphonic acid derivatives,their manufacture and pharmaceutical compositions containing them
US4473561A (en) *	1981-04-17	1984-09-25	Sumitomo Chemical Company, Limited	Fungicidal composition comprising alpha-substituted ethylphosphinic acids or their salts
US4466913A (en) *	1981-06-30	1984-08-21	Maiji Seika Kaisha Ltd.	Phosphorus-containing compounds and process for producing the same
US4477391A (en) *	1981-08-14	1984-10-16	Collins James F	Amino acid isomers, their production and their medicinal use
SE455259B (sv) *	1984-01-30	1988-07-04	Kenogard Ab	Anvendning av vissa aminoalkanfosfonsyror for bekempning av svampsjukdomar hos vexter
US5189030A (en) *	1985-06-11	1993-02-23	Ciba-Geigy Corporation	1-amino-2-phenylethanephosphonic acids as microbiocides
US5099063A (en) *	1986-11-05	1992-03-24	Merck & Co., Inc.	Certain phosphinic acid derivatives having antibacterial activity
US5143908A (en) *	1986-11-05	1992-09-01	Merck & Co., Inc.	Antibacterial agents and potentiators of carbapenem antibiotics
US4761405A (en) *	1987-03-04	1988-08-02	Nova Pharmaceutical Corporation	Antagonists of specific excitatory amino acid neurotransmitter receptors having increased potency
US5041644A (en) *	1987-07-06	1991-08-20	Merck & Co., Inc.	Peptide derivatives of β-chloro-L(Z)-dehydro-glutamic acid
JPS6413097A (en) *	1987-07-06	1989-01-17	Mitsubishi Chem Ind	Phosphonic acid derivative
US5030732A (en) *	1988-03-03	1991-07-09	Merck & Co., Inc.	Aminoethylphosphinic acid derivatives
US4962097A (en) *	1988-10-28	1990-10-09	Merck & Co., Inc.	Method of treating bacterial infection with phosphorus containing DHP enzyme inhibitors
US5147867A (en) *	1988-10-28	1992-09-15	Merck & Co., Inc.	Phosphorus containing enzyme inhibitors
US5145990A (en) *	1988-10-28	1992-09-08	Merck & Co., Inc.	Phosphorous containing dhp enzyme inhibitors
US5179173A (en) *	1991-04-10	1993-01-12	Nalco Chemical Company	Aminoalkylphosphinates and phosphinic acid-containing polymers therefrom
FI963390A (fi) *	1996-08-30	1998-03-01	Khomutov Radii M	Kasvinsuojeluaineet
IT201600098005A1 (it) *	2016-09-29	2018-03-29	Univ Degli Studi Roma La Sapienza	Analoghi e derivati di amminoacidi dicarbossilici come antibatterici

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3160632A (en) *	1961-01-30	1964-12-08	Stauffer Chemical Co	Aminomethylenephosphinic acids, salts thereof, and process for their production
CH475287A (de) *	1965-10-27	1969-07-15	Monsanto Co	Verfahren zur Herstellung von substituierten Aminomethylphosphinsäuren
US3424788A (en) *	1967-07-24	1969-01-28	Armour & Co	Aminophosphinic acids and salts useful as bacteriostats

1976
- 1976-05-21 GB GB21000/76A patent/GB1542938A/en not_active Expired
1977
- 1977-05-14 EG EG293/77A patent/EG12688A/xx active
- 1977-05-17 DE DE19772722162 patent/DE2722162A1/de not_active Withdrawn
- 1977-05-18 FR FR7715324A patent/FR2360601A1/fr active Granted
- 1977-05-18 SE SE7705886A patent/SE7705886L/xx unknown
- 1977-05-19 CA CA278,750A patent/CA1081241A/en not_active Expired
- 1977-05-19 PH PH19791A patent/PH14170A/en unknown
- 1977-05-19 BG BG7736361A patent/BG27905A3/xx unknown
- 1977-05-19 BG BG7737259A patent/BG28070A4/xx unknown
- 1977-05-19 ES ES458931A patent/ES458931A1/es not_active Expired
- 1977-05-19 DD DD7700199017A patent/DD131751A5/xx unknown
- 1977-05-19 FI FI771602A patent/FI771602A/fi not_active Application Discontinuation
- 1977-05-19 IL IL52127A patent/IL52127A0/xx unknown
- 1977-05-20 PL PL1977209221A patent/PL106608B1/pl unknown
- 1977-05-20 CS CS773353A patent/CS202066B2/cs unknown
- 1977-05-20 DK DK221477A patent/DK221477A/da unknown
- 1977-05-20 AT AT361777A patent/AT350585B/de not_active IP Right Cessation
- 1977-05-20 IE IE1036/77A patent/IE44904B1/en unknown
- 1977-05-20 PT PT66581A patent/PT66581B/pt unknown
- 1977-05-20 BE BE177743A patent/BE854843A/xx not_active IP Right Cessation
- 1977-05-20 NZ NZ184166A patent/NZ184166A/xx unknown
- 1977-05-20 ZA ZA00773017A patent/ZA773017B/xx unknown
- 1977-05-20 NO NO771770A patent/NO771770L/no unknown
- 1977-05-20 NL NL7705602A patent/NL7705602A/xx not_active Application Discontinuation
- 1977-05-20 AU AU25319/77A patent/AU516592B2/en not_active Expired
- 1977-05-20 PL PL1977198267A patent/PL110527B1/pl not_active IP Right Cessation
- 1977-05-20 SU SU772484356A patent/SU805948A3/ru active
- 1977-05-21 JP JP5823477A patent/JPS52151128A/ja active Pending
- 1977-05-23 US US05/799,428 patent/US4147780A/en not_active Expired - Lifetime
- 1977-05-23 OA OA56174A patent/OA05666A/xx unknown
- 1977-05-23 AR AR267742A patent/AR219077A1/es active
1978
- 1978-04-17 AR AR271804A patent/AR222464A1/es active
- 1978-06-09 SU SU782623755A patent/SU795484A3/ru active

Also Published As

Publication number	Publication date
ES458931A1 (es)	1978-03-01
EG12688A (en)	1979-06-30
PL106608B1 (pl)	1980-01-31
ATA361777A (de)	1978-11-15
BE854843A (fr)	1977-11-21
OA05666A (fr)	1981-05-31
AT350585B (de)	1979-06-11
CS202066B2 (en)	1980-12-31
JPS52151128A (en)	1977-12-15
PT66581A (en)	1977-06-01
SE7705886L (sv)	1977-11-22
SU795484A3 (ru)	1981-01-07
SU805948A3 (ru)	1981-02-15
PH14170A (en)	1981-03-19
FI771602A (es)	1977-11-22
DK221477A (da)	1977-11-22
DD131751A5 (de)	1978-07-19
NZ184166A (en)	1980-03-05
AR222464A1 (es)	1981-05-29
PT66581B (en)	1978-10-20
BG27905A3 (en)	1980-01-15
FR2360601B1 (es)	1979-09-07
AR219077A1 (es)	1980-07-31
CA1081241A (en)	1980-07-08
PL110527B1 (en)	1980-07-31
IE44904B1 (en)	1982-05-05
AU2531977A (en)	1978-11-23
BG28070A4 (en)	1980-02-25
AU516592B2 (en)	1981-06-11
ZA773017B (en)	1978-04-26
DE2722162A1 (de)	1977-12-01
IE44904L (en)	1977-11-21
FR2360601A1 (fr)	1978-03-03
PL198267A1 (pl)	1978-03-13
GB1542938A (en)	1979-03-28
IL52127A0 (en)	1977-07-31
NL7705602A (nl)	1977-11-23
US4147780A (en)	1979-04-03

Publication	Publication Date	Title
NO771770L (no)	1977-11-22	Fremgangsm}te til fremstilling av fosfonsyre
FI63754B (fi)	1983-04-29	Foerfarande foer framstaellning av en terapeutiskt anvaendbar ftalan
FI71126C (fi)	1986-11-24	Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider
EP1611129B1 (en)	2009-09-30	Cyclic sulfamides for inhibition of gamma-secretase
US7173033B2 (en)	2007-02-06	Nitrogen-containing heterocyclic compound
US6410582B1 (en)	2002-06-25	Thienylazolylalcoxyethanamines, their preparation and their application as medicaments
KR880001539B1 (ko)	1988-08-20	2-하이드록시-3-(치환된아미노)-프로폭시벤젠유도체 및 이의 제조방법
US4299838A (en)	1981-11-10	Tryptophan derivatives having an increased effect on the central nervous system
US20100216855A1 (en)	2010-08-26	Imidazaolone derivatives,preparation thereof and biological use of same
US4391821A (en)	1983-07-05	7-Substituted benzopyranes and process for the preparation thereof
NZ239267A (en)	1994-05-26	3-substituted piperidine derivatives and pharmaceutical compositions
NO155880B (no)	1987-03-09	Analogifremgangsmaate til fremstilling av terapeutisk aktivt 2-(2'hydroksy-3'-(1,1-dimetylpropylamino)-propoksy)-beta-fenylpropionfenon.
HU182884B (en)	1984-03-28	Process for preparing 4-phenyl-1,3-benzodiazepine derivatives and pharmaceutically acceptable salts and optical antipodes thereof further pharmaceutical compositions containing these compounds as active substances
NO140348B (no)	1979-05-07	Analogifremgangsmaate til fremstilling av nye terapeutisk aktive 3-(amino-2-hydroksypropoksy)-isoindolin-1-on-forbindelser
NZ210762A (en)	1988-02-29	Quinoline derivatives and pharmaceutical compositions
US5077290A (en)	1991-12-31	Morpholine derivatives compositions and use
US6939887B2 (en)	2005-09-06	Benzimidazolidinone derivatives
JPS58188879A (ja)	1983-11-04	シプロヘプタジン−３−カルボン酸及び構造的に関連した化合物のエステル
US4183858A (en)	1980-01-15	α-Vinyl tryptophanes
JPS61126082A (ja)	1986-06-13	アミノピロリジン誘導体、そのエステルおよびその塩
HU178147B (en)	1982-03-28	Process for producing hexahydro-1,4-oxazepines
HU202222B (en)	1991-02-28	Process for producing thiophene derivatives and pharmaceutical compositions comprising same as active ingredient
JPS5935387B2 (ja)	1984-08-28	３−アミノ−２−ヒドロキシプロパンのジ−置換フエノ−ルエ−テル類、その製法ならびに医薬用途
SU816402A3 (ru)	1981-03-23	Способ получени аминопроизводных2-МЕТил-5-(2-ОКСиСТиРил)-1,3,4-ТиА-диАзОлА или иХ СОлЕй
US3382260A (en)	1968-05-07	Novel sulfonamide compounds and processes