DE2413966A1 - Oxamidsaeure-derivate - Google Patents
Oxamidsaeure-derivateInfo
- Publication number
- DE2413966A1 DE2413966A1 DE2413966A DE2413966A DE2413966A1 DE 2413966 A1 DE2413966 A1 DE 2413966A1 DE 2413966 A DE2413966 A DE 2413966A DE 2413966 A DE2413966 A DE 2413966A DE 2413966 A1 DE2413966 A1 DE 2413966A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkoxy
- pyridyl
- acid
- nitro
- ester
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 title claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 102
- -1 2-cyanophenyl Chemical group 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 57
- 125000004494 ethyl ester group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical class ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- RLKPJTQKNVERIB-UHFFFAOYSA-N n-phenyl-2h-tetrazole-5-carboxamide Chemical compound N=1N=NNC=1C(=O)NC1=CC=CC=C1 RLKPJTQKNVERIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 3
- GGLRYZACPLNCKB-UHFFFAOYSA-N ethyl 2-(2-carbamoyl-3-methoxyanilino)-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=CC(OC)=C1C(N)=O GGLRYZACPLNCKB-UHFFFAOYSA-N 0.000 claims description 3
- YDGAUBHNAKCSKF-UHFFFAOYSA-N ethyl 2-anilino-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=CC=C1 YDGAUBHNAKCSKF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- IDMMJHZAWXBGBL-UHFFFAOYSA-N butan-2-yl 2-amino-2-oxoacetate Chemical compound CCC(C)OC(=O)C(N)=O IDMMJHZAWXBGBL-UHFFFAOYSA-N 0.000 claims description 2
- JQOLMUGUXNNIOR-UHFFFAOYSA-N butyl 2-amino-2-oxoacetate Chemical compound CCCCOC(=O)C(N)=O JQOLMUGUXNNIOR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- AEVHVVDLIHWAGR-UHFFFAOYSA-N methyl 2-amino-2-oxoacetate Chemical compound COC(=O)C(N)=O AEVHVVDLIHWAGR-UHFFFAOYSA-N 0.000 claims description 2
- RJCRYURSHNAGKB-UHFFFAOYSA-N methyl 2-anilino-2-oxoacetate Chemical compound COC(=O)C(=O)NC1=CC=CC=C1 RJCRYURSHNAGKB-UHFFFAOYSA-N 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XJUSRAJAEPIPIY-UHFFFAOYSA-N propyl 2-amino-2-oxoacetate Chemical compound CCCOC(=O)C(N)=O XJUSRAJAEPIPIY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 8
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 claims 1
- YRGCKBHUZNQXEL-UHFFFAOYSA-N 2-chloro-6-methoxybenzonitrile Chemical compound COC1=CC=CC(Cl)=C1C#N YRGCKBHUZNQXEL-UHFFFAOYSA-N 0.000 claims 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 claims 1
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 claims 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000012445 acidic reagent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- GYFAUGCHIXCGOJ-UHFFFAOYSA-N cyclohexyl 2-amino-2-oxoacetate Chemical compound NC(=O)C(=O)OC1CCCCC1 GYFAUGCHIXCGOJ-UHFFFAOYSA-N 0.000 claims 1
- QDDMLBBXHFMAJZ-UHFFFAOYSA-N ethyl 2-(4-methoxyanilino)-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=C(OC)C=C1 QDDMLBBXHFMAJZ-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- PSYJOBOWPNKDLG-UHFFFAOYSA-N n'-(2-carbamoyl-3-methoxyphenyl)oxamide Chemical compound COC1=CC=CC(NC(=O)C(N)=O)=C1C(N)=O PSYJOBOWPNKDLG-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- MJPLPRYORYZQEN-UHFFFAOYSA-N propan-2-yl 2-anilino-2-oxoacetate Chemical compound CC(C)OC(=O)C(=O)NC1=CC=CC=C1 MJPLPRYORYZQEN-UHFFFAOYSA-N 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 235000019441 ethanol Nutrition 0.000 description 37
- 238000002425 crystallisation Methods 0.000 description 28
- 230000008025 crystallization Effects 0.000 description 28
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 17
- 230000000694 effects Effects 0.000 description 13
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- AQAHTARDEJNYPN-UHFFFAOYSA-N 2-amino-6-methoxybenzamide Chemical compound COC1=CC=CC(N)=C1C(N)=O AQAHTARDEJNYPN-UHFFFAOYSA-N 0.000 description 7
- 239000000427 antigen Substances 0.000 description 7
- 102000036639 antigens Human genes 0.000 description 7
- 108091007433 antigens Proteins 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 239000000043 antiallergic agent Substances 0.000 description 6
- 208000010668 atopic eczema Diseases 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 208000024780 Urticaria Diseases 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010003645 Atopy Diseases 0.000 description 3
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229960000265 cromoglicic acid Drugs 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
- 210000003630 histaminocyte Anatomy 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 102400000967 Bradykinin Human genes 0.000 description 2
- 101800004538 Bradykinin Proteins 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 208000030961 allergic reaction Diseases 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000002124 endocrine Effects 0.000 description 2
- XEKONFTWUGSZSC-UHFFFAOYSA-N ethyl 2-(naphthalen-1-ylamino)-2-oxoacetate Chemical compound C1=CC=C2C(NC(=O)C(=O)OCC)=CC=CC2=C1 XEKONFTWUGSZSC-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002912 oxalic acid derivatives Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- OSEGRQQAWQNJBR-UHFFFAOYSA-N 1-nitro-4-(trifluoromethyl)cyclohexa-2,4-dien-1-amine Chemical compound NC1(CC=C(C=C1)C(F)(F)F)[N+](=O)[O-] OSEGRQQAWQNJBR-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- ZYDGHQSJZAFMLU-UHFFFAOYSA-N 2,6-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1C#N ZYDGHQSJZAFMLU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34446673A | 1973-03-23 | 1973-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2413966A1 true DE2413966A1 (de) | 1974-09-26 |
Family
ID=23350656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2413966A Ceased DE2413966A1 (de) | 1973-03-23 | 1974-03-22 | Oxamidsaeure-derivate |
Country Status (14)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2627784A1 (de) * | 1975-07-07 | 1977-01-27 | Upjohn Co | Oxalsaeureamidderivate und diese enthaltende arzneimittel |
| US4407810A (en) | 1980-07-19 | 1983-10-04 | Basf Aktiengesellschaft | Thiazol-2-yl-oxamic acid derivatives, and therapeutic agents containing these compounds |
| EP0044443B1 (de) * | 1980-07-19 | 1984-02-01 | BASF Aktiengesellschaft | Cycloalkano-thiazolyloxamidsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel |
| US4517196A (en) * | 1981-09-05 | 1985-05-14 | Basf Aktiengesellschaft | Tricyclic thiazolyloxamic acids and their derivatives, their preparation, and therapeutic agents containing these compounds |
| WO1999046236A1 (en) * | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| US6225329B1 (en) | 1998-03-12 | 2001-05-01 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPases) |
| EP2033688A2 (de) | 2007-08-20 | 2009-03-11 | Symrise GmbH & Co. KG | Oxalsäurederivate und deren Verwendung als physiologische Kühlwirkstoffe |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172147A (en) * | 1976-11-17 | 1979-10-23 | The Upjohn Company | 3,5-Dinitro oxanilic acid ester compounds, compositions and methods |
| US4119783A (en) * | 1977-02-18 | 1978-10-10 | The Upjohn Company | 3'Lower alkylcarbonyl oxanilic acid esters |
| NL7810634A (nl) * | 1977-10-28 | 1979-05-02 | May & Baker Ltd | Tetrazool-derivaten. |
| FR2546885B1 (fr) * | 1983-06-06 | 1986-02-07 | Fabre Sa Pierre | Oxamates d'anthranilates fonctionnalises utiles comme medicaments dans le traitement des dermatoses inflammatoires |
| JPS6112268U (ja) * | 1984-06-25 | 1986-01-24 | 松下電工株式会社 | プリント配線基板 |
| JPH072697B2 (ja) * | 1985-05-24 | 1995-01-18 | 久光製薬株式会社 | 新規なオキサニル酸誘導体 |
-
1974
- 1974-01-01 AR AR252822A patent/AR207563A1/es active
- 1974-01-30 ZA ZA00740635A patent/ZA74635B/xx unknown
- 1974-03-04 PH PH15573A patent/PH14870A/en unknown
- 1974-03-06 FI FI662/74A patent/FI61688C/fi active
- 1974-03-20 EG EG86/74A patent/EG11281A/xx active
- 1974-03-21 NL NL7403843A patent/NL7403843A/xx not_active Application Discontinuation
- 1974-03-22 CA CA195,729A patent/CA1034118A/en not_active Expired
- 1974-03-22 SE SE7403941A patent/SE411898B/xx unknown
- 1974-03-22 FR FR7409903A patent/FR2222097B1/fr not_active Expired
- 1974-03-22 CH CH405374A patent/CH612914A5/xx not_active IP Right Cessation
- 1974-03-22 ES ES424514A patent/ES424514A1/es not_active Expired
- 1974-03-22 DE DE2413966A patent/DE2413966A1/de not_active Ceased
- 1974-03-22 BE BE142383A patent/BE812743A/xx not_active IP Right Cessation
- 1974-03-23 JP JP49033104A patent/JPS5920664B2/ja not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2627784A1 (de) * | 1975-07-07 | 1977-01-27 | Upjohn Co | Oxalsaeureamidderivate und diese enthaltende arzneimittel |
| US4407810A (en) | 1980-07-19 | 1983-10-04 | Basf Aktiengesellschaft | Thiazol-2-yl-oxamic acid derivatives, and therapeutic agents containing these compounds |
| EP0044443B1 (de) * | 1980-07-19 | 1984-02-01 | BASF Aktiengesellschaft | Cycloalkano-thiazolyloxamidsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel |
| US4517196A (en) * | 1981-09-05 | 1985-05-14 | Basf Aktiengesellschaft | Tricyclic thiazolyloxamic acids and their derivatives, their preparation, and therapeutic agents containing these compounds |
| WO1999046236A1 (en) * | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| US6225329B1 (en) | 1998-03-12 | 2001-05-01 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (PTPases) |
| EP2033688A2 (de) | 2007-08-20 | 2009-03-11 | Symrise GmbH & Co. KG | Oxalsäurederivate und deren Verwendung als physiologische Kühlwirkstoffe |
| US8344025B2 (en) | 2007-08-20 | 2013-01-01 | Symrise Ag | Oxalic acid derivatives and use thereof as physiological cooling active ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| ES424514A1 (es) | 1976-06-16 |
| JPS5920664B2 (ja) | 1984-05-15 |
| NL7403843A (enrdf_load_stackoverflow) | 1974-09-25 |
| AU6575374A (en) | 1975-08-21 |
| JPS49135929A (enrdf_load_stackoverflow) | 1974-12-27 |
| CA1034118A (en) | 1978-07-04 |
| FI61688B (fi) | 1982-05-31 |
| ZA74635B (en) | 1975-09-24 |
| EG11281A (en) | 1977-05-31 |
| CH612914A5 (en) | 1979-08-31 |
| FR2222097A1 (enrdf_load_stackoverflow) | 1974-10-18 |
| FI61688C (fi) | 1982-09-10 |
| AR207563A1 (es) | 1976-10-15 |
| BE812743A (fr) | 1974-09-23 |
| FR2222097B1 (enrdf_load_stackoverflow) | 1978-06-30 |
| SE411898B (sv) | 1980-02-11 |
| PH14870A (en) | 1982-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |