CH431553A - Verfahren zur Herstellung von Benzyloxyaminen und deren Säureanlagerungssalzen - Google Patents

Verfahren zur Herstellung von Benzyloxyaminen und deren Säureanlagerungssalzen

Info

Publication number: CH431553A
Authority: CH; Switzerland
Prior art keywords: benzyl; hydrogen; preparation; formula; group
Prior art date: 1961-01-23

Application number

CH77362A

Other languages

German (de)

English (en)

Inventor

John Ludwig Bernard

Milan Berger Frank

Original Assignee

Carter Prod 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.)

1961-01-23

Filing date

1962-01-23

Publication date

1967-03-15

1962-01-23 Application filed by Carter Prod Inc filed Critical Carter Prod Inc

1967-03-15 Publication of CH431553A publication Critical patent/CH431553A/de

Links

238000000034 method Methods 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 25
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical class NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 title claims description 13
239000002253 acid Substances 0.000 title claims description 11
150000003839 salts Chemical class 0.000 title claims description 11
-1 benzyl compound Chemical class 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
VGEWEGHHYWGXGG-UHFFFAOYSA-N ethyl n-hydroxycarbamate Chemical compound CCOC(=O)NO VGEWEGHHYWGXGG-UHFFFAOYSA-N 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 7
XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000003254 radicals Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
WUUIYHZKEXDJKH-UHFFFAOYSA-N 1-phenyl-n-phenylmethoxymethanamine Chemical class C=1C=CC=CC=1CNOCC1=CC=CC=C1 WUUIYHZKEXDJKH-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
125000003435 aroyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
150000002443 hydroxylamines Chemical class 0.000 claims description 3
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 claims description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
229940073608 benzyl chloride Drugs 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
230000007062 hydrolysis Effects 0.000 claims 2
238000006460 hydrolysis reaction Methods 0.000 claims 2
231100000252 nontoxic Toxicity 0.000 claims 2
230000003000 nontoxic effect Effects 0.000 claims 2
239000007858 starting material Substances 0.000 claims 2
LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 claims 1
101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 claims 1
239000012948 isocyanate Substances 0.000 claims 1
150000002513 isocyanates Chemical class 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
CMKJWNXXUNBWJC-UHFFFAOYSA-N o-[(3-methylphenyl)methyl]hydroxylamine Chemical compound CC1=CC=CC(CON)=C1 CMKJWNXXUNBWJC-UHFFFAOYSA-N 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 28
239000000203 mixture Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 19
239000004480 active ingredient Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
235000012000 cholesterol Nutrition 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
210000004369 blood Anatomy 0.000 description 12
239000008280 blood Substances 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
238000001816 cooling Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
241001465754 Metazoa Species 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
239000002244 precipitate Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000013641 positive control Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000002904 solvent Substances 0.000 description 4
GJSJEIZRIATZFM-UHFFFAOYSA-N 1-(4-methylphenyl)-N-[(4-methylphenyl)methoxy]methanamine Chemical compound CC1=CC=C(CNOCC2=CC=C(C)C=C2)C=C1 GJSJEIZRIATZFM-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
MYYYZNVAUZVXBO-UHFFFAOYSA-N 1-(bromomethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(CBr)=C1 MYYYZNVAUZVXBO-UHFFFAOYSA-N 0.000 description 2
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
244000208874 Althaea officinalis Species 0.000 description 2
235000006576 Althaea officinalis Nutrition 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000005574 benzylation reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
235000021050 feed intake Nutrition 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000013642 negative control Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
RNVSTHULZRDHTR-UHFFFAOYSA-N 1-(2-methylphenyl)-n-phenylmethoxymethanamine Chemical compound CC1=CC=CC=C1CNOCC1=CC=CC=C1 RNVSTHULZRDHTR-UHFFFAOYSA-N 0.000 description 1
PNWCJLFRYRHCFB-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n-[(4-methoxyphenyl)methoxy]methanamine Chemical compound C1=CC(OC)=CC=C1CNOCC1=CC=C(OC)C=C1 PNWCJLFRYRHCFB-UHFFFAOYSA-N 0.000 description 1
MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 1
WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 1
FWLWTILKTABGKQ-UHFFFAOYSA-N 1-(bromomethyl)-3-methylbenzene Chemical group CC1=CC=CC(CBr)=C1 FWLWTILKTABGKQ-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
WDDGAVMTDOWENK-UHFFFAOYSA-N 1-benzyl-1-phenylmethoxyurea Chemical compound C=1C=CC=CC=1CON(C(=O)N)CC1=CC=CC=C1 WDDGAVMTDOWENK-UHFFFAOYSA-N 0.000 description 1
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
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NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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YDWPOGYTJVQQIL-UHFFFAOYSA-N methyl 2-(4-aminophenoxy)acetate Chemical compound COC(=O)COC1=CC=C(N)C=C1 YDWPOGYTJVQQIL-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
NNMXAXRLGAZPLD-UHFFFAOYSA-N n-benzyl-n-phenylmethoxybenzamide Chemical compound C=1C=CC=CC=1C(=O)N(OCC=1C=CC=CC=1)CC1=CC=CC=C1 NNMXAXRLGAZPLD-UHFFFAOYSA-N 0.000 description 1
HNNYXMYQJHGSTI-UHFFFAOYSA-N n-hydroxy-2-methyl-3-phenylpropanamide Chemical compound ONC(=O)C(C)CC1=CC=CC=C1 HNNYXMYQJHGSTI-UHFFFAOYSA-N 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
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HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
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235000020075 ouzo Nutrition 0.000 description 1
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AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
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239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
CMDGQTVYVAKDNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrate Chemical compound O.OCC(O)CO CMDGQTVYVAKDNA-UHFFFAOYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
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238000012453 sprague-dawley rat model Methods 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
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231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH77362A 1961-01-23 1962-01-23 Verfahren zur Herstellung von Benzyloxyaminen und deren Säureanlagerungssalzen CH431553A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8395461A	1961-01-23	1961-01-23
US16485662A	1962-01-09	1962-01-09

Publications (1)

Publication Number	Publication Date
CH431553A true CH431553A (de)	1967-03-15

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CH77362A CH431553A (de)	1961-01-23	1962-01-23	Verfahren zur Herstellung von Benzyloxyaminen und deren Säureanlagerungssalzen

Country Status (8)

Country	Link
AT (1)	AT248415B (fr)
CH (1)	CH431553A (fr)
DE (1)	DE1693189B1 (fr)
DK (1)	DK118189B (fr)
ES (1)	ES273978A1 (fr)
FI (1)	FI40633B (fr)
FR (1)	FR2693M (fr)
LU (1)	LU41137A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4696964A (en) *	1986-04-11	1987-09-29	Ciba-Geigy Corporation	Compositions stabilized with ethers of di- and tri-substituted hydroxylamines
FR2754254B1 (fr) *	1996-10-09	1998-10-30	Rhone Poulenc Agrochimie	Fongicides a groupes hydroximiques et hydrazoniques

1962
- 1962-01-19 DK DK25362AA patent/DK118189B/da unknown
- 1962-01-20 DE DE19621693189 patent/DE1693189B1/de active Pending
- 1962-01-22 FI FI0114/62A patent/FI40633B/fi active
- 1962-01-23 LU LU41137D patent/LU41137A1/xx unknown
- 1962-01-23 AT AT55262A patent/AT248415B/de active
- 1962-01-23 CH CH77362A patent/CH431553A/de unknown
- 1962-01-23 ES ES0273978A patent/ES273978A1/es not_active Expired
- 1962-04-18 FR FR894964A patent/FR2693M/fr not_active Expired

Also Published As

Publication number	Publication date
AT248415B (de)	1966-07-25
ES273978A1 (es)	1962-07-01
DE1693189B1 (de)	1972-12-07
LU41137A1 (fr)	1962-03-23
DK118189B (da)	1970-07-20
FR2693M (fr)	1964-08-03
FI40633B (fr)	1968-12-31

Publication	Publication Date	Title
DE1493955B2 (de)	1976-11-18	Sulfonanilide und verfahren zu ihrer herstellung
DE2928485A1 (de)	1981-01-29	Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen
CH630881A5 (de)	1982-07-15	Verfahren zur herstellung neuer substituierter fluoracylresorcine.
DD201781A5 (de)	1983-08-10	Verfahren zur herstellung von brenztraubensaeureoximen
DE1445186B2 (de)	1974-03-28	3,3'-Di-2-imidazolin-2-yl-carbanilid
EP0054872A1 (fr)	1982-06-30	Oxadiazole-1,2,5 oxydes-2 bis-substitués en position 3 et 4, leur procédé de préparation, et compositions pharmaceutiques les contenant
DE2221758A1 (de)	1972-11-23	Yohimbinderivate,Verfahren zu ihrer Herstellung und ihre Verwendung
CH431553A (de)	1967-03-15	Verfahren zur Herstellung von Benzyloxyaminen und deren Säureanlagerungssalzen
US3245878A (en)	1966-04-12	Methods for lowering blood cholesterol
DE2157272B2 (de)	1978-07-06	Verwendung von bis-(p-Chlorphenoxy)acetylharnstoff
DD141023A5 (de)	1980-04-09	Verfahren zur herstellung eines 2,3-dihydrobenzofuranderivats
DE2725245A1 (de)	1977-12-15	Methylaminderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische oder veterinaermedizinische zusammensetzungen
DD275689A5 (de)	1990-01-31	Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid
DE2522218A1 (de)	1975-12-04	Therapeutische zusammensetzung, methylaminderivate und verfahren zu deren herstellung
DE2113489C3 (de)	1980-05-08	2-Nitro-benzofuranderivate, ein Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
CH409996A (de)	1966-03-31	Verfahren zur Herstellung von substituierten Hydrazinen
DE2917890C2 (fr)	1987-10-29
DE1620466C3 (de)	1976-01-02	2,3,5,6-Tetrahydroindolderivate und Verfahren zu ihrer Herstellung
DE2414084A1 (de)	1974-10-03	Dinitroanilinderivate
DE69528984T2 (de)	2003-09-04	Hemmung der leukotrienbiosynthese mittels harnstoffderivaten
DE1026301B (de)	1958-03-20	Verfahren zur Herstellung von antimykotisch wirksamen 4-Halogensalicylsaeureamiden
DE3220185A1 (de)	1982-12-23	4-amino-benzylamin-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als pharmazeutica
DE1937759A1 (de)	1970-09-24	Benzolsulfonylsemicarbazide und Verfahren zu ihrer Herstellung
AT233310B (de)	1964-05-11	Coccidiostatische Zubereitungen
DE1695501A1 (de)	1971-04-15	Neue 1,2,4-Oxdiazolidine