NO118325B - - Google Patents

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Publication number: NO118325B
Authority: NO; Norway
Prior art keywords: atom; mol; solution; melting point; residue
Prior art date: 1965-04-12

Application number

NO162525A

Other languages

English (en)

Norwegian (no)

Inventor

P Juby

Original Assignee

Bristol Myers Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-04-12

Filing date

1966-04-06

Publication date

1969-12-15

1966-04-06 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1969-12-15 Publication of NO118325B publication Critical patent/NO118325B/no

Links

-1 2-(5-tetrazolyl)-N-substituted phenylanilines Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 3
UZEFHQIOSJWWSB-UHFFFAOYSA-N 4-azidobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=[N+]=[N-])C=C1 UZEFHQIOSJWWSB-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
239000013078 crystal Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000000460 chlorine Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
239000003610 charcoal Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
206010030113 Oedema Diseases 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
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 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OVFJZEDBZAIHBE-UHFFFAOYSA-N 2-(2,3-dimethylanilino)benzamide Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(N)=O)=C1C OVFJZEDBZAIHBE-UHFFFAOYSA-N 0.000 description 3
ZWADFWPVXXWOEY-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(NC=2C(=CC=CC=2)C#N)=C1 ZWADFWPVXXWOEY-UHFFFAOYSA-N 0.000 description 3
QAPPKIJGVCMOCB-UHFFFAOYSA-N 3,5-dichloro-4-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(Cl)C(O)=C(Cl)C=C1C(O)=O QAPPKIJGVCMOCB-UHFFFAOYSA-N 0.000 description 3
IAMNVCJECQWBLZ-UHFFFAOYSA-N 4-hydroxy-2-methylacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1C IAMNVCJECQWBLZ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 2
XGVSZZUMOBLJPI-UHFFFAOYSA-N 2,4-bis(2,6-dichloro-3-methylphenoxy)quinazoline Chemical compound ClC1=C(OC2=NC3=CC=CC=C3C(=N2)OC2=C(C(=CC=C2Cl)C)Cl)C(=CC=C1C)Cl XGVSZZUMOBLJPI-UHFFFAOYSA-N 0.000 description 2
SXHLRMKATYCFRY-UHFFFAOYSA-N 2,6-dichloro-3-methylphenol Chemical compound CC1=CC=C(Cl)C(O)=C1Cl SXHLRMKATYCFRY-UHFFFAOYSA-N 0.000 description 2
KMDLUTSCRNPJDP-UHFFFAOYSA-N 2-(2,6-dichloro-3-methylanilino)benzonitrile Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C#N)=C1Cl KMDLUTSCRNPJDP-UHFFFAOYSA-N 0.000 description 2
YOOQXVNSJQLHRB-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]benzamide Chemical compound NC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 YOOQXVNSJQLHRB-UHFFFAOYSA-N 0.000 description 2
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
239000005751 Copper oxide Substances 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 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
229910021529 ammonia Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910000431 copper oxide Inorganic materials 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
TVEMHVZQZUEHRZ-UHFFFAOYSA-N ethyl 2-[3-(trifluoromethyl)anilino]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 TVEMHVZQZUEHRZ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
LCCVYZLUEHOBDC-UHFFFAOYSA-N methyl 2-(2,3-dimethylanilino)benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=CC=CC(C)=C1C LCCVYZLUEHOBDC-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
OVBXTQJLKUWIBW-UHFFFAOYSA-N 2,6-dichloro-3-methyl-N-[2-(2H-tetrazol-5-yl)phenyl]aniline Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C=2NN=NN=2)=C1Cl OVBXTQJLKUWIBW-UHFFFAOYSA-N 0.000 description 1
KYGRLTPJZMZRJS-UHFFFAOYSA-N 2-(2,6-dichloro-3-methylanilino)benzamide Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(N)=O)=C1Cl KYGRLTPJZMZRJS-UHFFFAOYSA-N 0.000 description 1
JPEXITLSZOMSFC-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)-n-[3-(trifluoromethyl)phenyl]aniline Chemical compound FC(F)(F)C1=CC=CC(NC=2C(=CC=CC=2)C2=NNN=N2)=C1 JPEXITLSZOMSFC-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
238000006816 Chapman rearrangement reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
231100000229 OECD 452 Chronic Toxicity Study Toxicity 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
YDPLDMLRERBXAV-UHFFFAOYSA-N aluminum;triazide Chemical compound [Al+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] YDPLDMLRERBXAV-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical compound Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
OTGAHJPFNKQGAE-UHFFFAOYSA-N cresatin Chemical compound CC(=O)OC1=CC=CC(C)=C1 OTGAHJPFNKQGAE-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
230000007170 pathology Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 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
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
SUBUUGVBEKEFGW-UHFFFAOYSA-N tetramethylazanium;azide Chemical compound [N-]=[N+]=[N-].C[N+](C)(C)C SUBUUGVBEKEFGW-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO162525A 1965-04-12 1966-04-06 NO118325B (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US44751765A	1965-04-12	1965-04-12
US546546A US3294813A (en)	1965-04-12	1966-05-02	2-(5-tetrazolyl)-nu-(substituted-phenyl) anilines and salts thereof

Publications (1)

Publication Number	Publication Date
NO118325B true NO118325B (nl)	1969-12-15

Family

ID=27034999

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO162525A NO118325B (nl)	1965-04-12	1966-04-06

Country Status (8)

Country	Link
US (1)	US3294813A (nl)
BE (1)	BE679245A (nl)
CH (1)	CH479599A (nl)
FR (1)	FR5638M (nl)
GB (1)	GB1121447A (nl)
NL (1)	NL6604860A (nl)
NO (1)	NO118325B (nl)
SE (1)	SE311523B (nl)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH499527A (de) *	1968-07-18	1970-11-30	Ciba Geigy Ag	Verfahren zur Herstellung von neuen Tetrazolderivaten
US4029815A (en) *	1975-04-30	1977-06-14	Schering Corporation	Anti-diarrheal anthranilic acids
JPS6344570A (ja) *	1986-08-12	1988-02-25	Wakamoto Pharmaceut Co Ltd	３−（１ｈ−テトラゾ−ル−５−イル）オキサニリツクアシツド及びその製造法
FI902771A0 (fi) *	1989-06-09	1990-06-04	Warner Lambert Co	Foerfarande foer framstaellning av antiinflammatoriska 1,3,4-tiadiazoler och 1,3,4-oxadiazoler.
JP2002528499A (ja) *	1998-10-29	2002-09-03	ブリストル−マイヤーズスクイブカンパニー	Ｉｍｐｄｈ酵素のインヒビターであるアミノ核誘導化合物
NZ513432A (en)	1999-01-13	2004-02-27	Warner Lambert Co	1-heterocycle substituted diarylamines
EA200901551A1 (ru) *	2007-05-22	2010-06-30	Новартис Аг	Бензамиды, применимые в качестве модуляторов рецептора s1p

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3123615A (en) *		1964-03-03		Oxyphenyl
US2977372A (en) *	1958-04-09	1961-03-28	William G Finnegan	Process for preparing substituted tetrazoles
US3138636A (en) *	1960-06-23	1964-06-23	Parke Davis & Co	Anthranilic acid derivatives
US3155666A (en) *	1963-07-18	1964-11-03	Searle & Co	1-dialkylaminoalkyl-5-diphenylmethyl-1h-tetrazoles and related compounds

1966
- 1966-04-04 CH CH486966A patent/CH479599A/de not_active IP Right Cessation
- 1966-04-06 NO NO162525A patent/NO118325B/no unknown
- 1966-04-07 BE BE679245D patent/BE679245A/xx unknown
- 1966-04-12 SE SE4958/66A patent/SE311523B/xx unknown
- 1966-04-12 NL NL6604860A patent/NL6604860A/xx unknown
- 1966-04-12 GB GB16022/66A patent/GB1121447A/en not_active Expired
- 1966-05-02 US US546546A patent/US3294813A/en not_active Expired - Lifetime
- 1966-07-07 FR FR68619A patent/FR5638M/fr not_active Expired

Also Published As

Publication number	Publication date
NL6604860A (nl)	1966-10-13
FR5638M (nl)	1967-12-18
GB1121447A (en)	1968-07-24
US3294813A (en)	1966-12-27
CH479599A (de)	1969-10-15
BE679245A (nl)	1966-10-07
SE311523B (nl)	1969-06-16

Publication	Publication Date	Title
Finnegan et al.	1953	Preparation and isomerization of 5-alkylaminotetrazoles
EP0004279B1 (de)	1982-12-29	Verfahren zur Herstellung von 4-Pyridon-3-carbonsäuren, 1-Cyclopropyl-4-Pyridon-3-Carbonsäurederivate und diese enthaltende Arzneimittel
DE2524929A1 (de)	1976-12-16	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
NO164476B (no)	1990-07-02	Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner.
US3313848A (en)	1967-04-11	Anthranilic acids and derivatives
NO118325B (nl)	1969-12-15
EP0021207B1 (de)	1985-08-07	Alphacarbamoyl-pyrrolpropionitrile, Verfahren zu ihrer Herstellung, sowie pharmazeutische Präparate die diese Verbindungen enthalten
US3475427A (en)	1969-10-28	Phenoxazines
US2924599A (en)	1960-02-09	Derivatives of 1:3:5-triazanaphthalene
PL76889B1 (nl)	1975-02-28
Musser et al.	1989	N-[(arylmethoxy) phenyl] and N-[(arylmethoxy) naphthyl] sulfonamides: Potent orally active leukotriene D4 antagonists of novel structure
Freed	1946	New Compounds. Preparation and Reactions of 2, 4-Dichlorophenoxyacetyl Chloride
US3390172A (en)	1968-06-25	Nu-(3-trifluoromethylphenyl)-anthranilic acids
LEONARD et al.	1946	SOME NOVEL REACTIONS OF 4-QUINAZOLONE1, 2
CS216205B2 (en)	1982-10-29	Method of making the derivatives of the 1,4-diphenylpyrazole
US4254118A (en)	1981-03-03	1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters
EP1791814B1 (de)	2011-06-29	Ortho-substituierte pentafluorsulfanyl-benzole, verfahren zu ihrer herstellung sowie ihre verwendung als synthese-zwischenstufen
Tomisek et al.	1946	Syntheses of Certain 8-Nitroquinolines1
US3132019A (en)	1964-05-05	Method of eliminating weed grasses
CH498856A (de)	1970-11-15	Verfahren zur Herstellung von neuen Furazanderivaten
US3983126A (en)	1976-09-28	Aryloxy pyridine carboxylic-4-acids
US3972926A (en)	1976-08-03	Substituted trifluoromethanesulfonanilides
US3324173A (en)	1967-06-06	(2-methylenealkanoyl)benzoic acids
Leonard et al.	1946	New Compounds. 6-Bromo-1, 2, 3, 4-tetrahydroquinaldine Hydrobromide
CH546742A (de)	1974-03-15	Verfahren zur herstellung von methoxyamin-derivaten und ihren salzen.