CA1041100A - Acide pyridine-diyldioxamique - Google Patents

Acide pyridine-diyldioxamique

Info

Publication number: CA1041100A
Authority: CA; Canada
Prior art keywords: group; hydrogen; pyridine; carbon atoms; accordance
Prior art date: 1973-10-04
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.): Expired

Application number

CA207,416A

Other languages

English (en)

Other versions

CA207416S (en

Inventor

Herbert G. Johnson

Charles M. Hall

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn 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.)

1973-10-04

Filing date

1974-08-20

Publication date

1978-10-24

1974-08-20 Application filed by Upjohn Co filed Critical Upjohn Co

1978-10-24 Application granted granted Critical

1978-10-24 Publication of CA1041100A publication Critical patent/CA1041100A/fr

Status Expired legal-status Critical Current

Links

OSKLWPPLCZZGOI-UHFFFAOYSA-N 2-[[2-(oxaloamino)pyridin-3-yl]amino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CN=C1NC(=O)C(O)=O OSKLWPPLCZZGOI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 61
238000000034 method Methods 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
-1 amine cation Chemical class 0.000 claims description 22
229910052751 metal Inorganic materials 0.000 claims description 22
239000002184 metal Substances 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 11
OWCAKKIRPJUQFO-UHFFFAOYSA-N (2-methyl-2-nonyl-1,3-dioxolan-4-yl)methyl carbamate Chemical compound CCCCCCCCCC1(C)OCC(COC(N)=O)O1 OWCAKKIRPJUQFO-UHFFFAOYSA-N 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
229950001656 dioxamate Drugs 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
ZGBIXLDBKKUPQJ-UHFFFAOYSA-N 2-[[6-(oxaloamino)pyridin-2-yl]amino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC(NC(=O)C(O)=O)=N1 ZGBIXLDBKKUPQJ-UHFFFAOYSA-N 0.000 claims description 6
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
RBUSDTTZLFXFQJ-UHFFFAOYSA-N 2-[[6-(oxaloamino)pyridin-3-yl]amino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=C(NC(=O)C(O)=O)N=C1 RBUSDTTZLFXFQJ-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical group OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
WHKIQFYYHZPIBH-UHFFFAOYSA-N 2,6-dimethoxypyridine-3,5-diamine;hydron;dichloride Chemical compound Cl.Cl.COC1=NC(OC)=C(N)C=C1N WHKIQFYYHZPIBH-UHFFFAOYSA-N 0.000 claims description 2
LIHUFKFFORDAGE-UHFFFAOYSA-N 2-[[2,6-dimethoxy-5-(oxaloamino)pyridin-3-yl]amino]-2-oxoacetic acid Chemical compound COC1=NC(OC)=C(NC(=O)C(O)=O)C=C1NC(=O)C(O)=O LIHUFKFFORDAGE-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
239000000376 reactant Substances 0.000 claims 6
238000004519 manufacturing process Methods 0.000 claims 4
MEIIXFWYZQKEJV-UHFFFAOYSA-N ethyl 2-[[6-[(2-ethoxy-2-oxoacetyl)amino]pyridin-3-yl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=C(NC(=O)C(=O)OCC)N=C1 MEIIXFWYZQKEJV-UHFFFAOYSA-N 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
LRENAQITCKXATB-UHFFFAOYSA-N ethyl 2-[[5-[(2-ethoxy-2-oxoacetyl)amino]-2,6-dimethoxypyridin-3-yl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC(NC(=O)C(=O)OCC)=C(OC)N=C1OC LRENAQITCKXATB-UHFFFAOYSA-N 0.000 claims 1
KGLTVRLEAZBEOY-UHFFFAOYSA-N ethyl 2-[[6-[(2-ethoxy-2-oxoacetyl)amino]pyridin-2-yl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=CC(NC(=O)C(=O)OCC)=N1 KGLTVRLEAZBEOY-UHFFFAOYSA-N 0.000 claims 1
MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 11
206010020751 Hypersensitivity Diseases 0.000 abstract description 8
238000011321 prophylaxis Methods 0.000 abstract description 8
208000026935 allergic disease Diseases 0.000 abstract description 7
230000007815 allergy Effects 0.000 abstract description 7
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 abstract description 5
239000003937 drug carrier Substances 0.000 abstract description 4
230000002052 anaphylactic effect Effects 0.000 abstract description 3
230000001404 mediated effect Effects 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
239000002552 dosage form Substances 0.000 description 8
239000004615 ingredient Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000000047 product Substances 0.000 description 8
239000003380 propellant Substances 0.000 description 8
241000700159 Rattus Species 0.000 description 7
208000006673 asthma Diseases 0.000 description 7
239000007858 starting material Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
239000002585 base Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
206010002198 Anaphylactic reaction Diseases 0.000 description 5
238000007792 addition Methods 0.000 description 5
208000003455 anaphylaxis Diseases 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000036783 anaphylactic response Effects 0.000 description 4
238000003556 assay Methods 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
239000008101 lactose Substances 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
229940057948 magnesium stearate Drugs 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229920000609 methyl cellulose Polymers 0.000 description 4
239000001923 methylcellulose Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
230000002265 prevention Effects 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
229940033134 talc Drugs 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
235000019739 Dicalciumphosphate Nutrition 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000011149 active material Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
229940038472 dicalcium phosphate Drugs 0.000 description 3
238000011049 filling Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
229940092253 ovalbumin Drugs 0.000 description 3
239000008024 pharmaceutical diluent Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000004262 Food Hypersensitivity Diseases 0.000 description 2
206010016946 Food allergy Diseases 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
108010058846 Ovalbumin Proteins 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-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
229910052799 carbon Inorganic materials 0.000 description 2
AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
235000020932 food allergy Nutrition 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
229940090044 injection Drugs 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000006215 rectal suppository Substances 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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 1
101000941450 Lasioglossum laticeps Lasioglossin-1 Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
208000030961 allergic reaction Diseases 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
150000003927 aminopyridines Chemical class 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000001465 calcium Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229960005069 calcium Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
239000012971 dimethylpiperazine Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 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
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D213/73—Unsubstituted amino or imino radicals
- 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
- 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
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA207,416A 1973-10-04 1974-08-20 Acide pyridine-diyldioxamique Expired CA1041100A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US40367773A	1973-10-04	1973-10-04

Publications (1)

Publication Number	Publication Date
CA1041100A true CA1041100A (fr)	1978-10-24

Family

ID=23596609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA207,416A Expired CA1041100A (fr)	1973-10-04	1974-08-20	Acide pyridine-diyldioxamique

Country Status (9)

Country	Link
JP (1)	JPS603060B2 (fr)
BE (1)	BE820723A (fr)
CA (1)	CA1041100A (fr)
CH (1)	CH605767A5 (fr)
DE (1)	DE2445002C2 (fr)
FR (1)	FR2247237B1 (fr)
GB (1)	GB1436304A (fr)
NL (1)	NL179110C (fr)
ZA (1)	ZA745754B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3132885A1 (de) *	1981-08-20	1983-03-03	Wella Ag	Mittel und verfahren zur faerbung von haaren
DE3229539A1 (de) *	1982-08-07	1984-02-09	Basf Ag, 6700 Ludwigshafen	Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel
US5082467A (en) *	1990-02-08	1992-01-21	Kao Corporation	Dye composition for keratinous fibers
WO1996019454A1 (fr) *	1994-12-20	1996-06-27	Terumo Kabushiki Kaisha	Derives de pyridylalkyle-phenyl-sulfone et preparation medicinale les contenant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH531000A (de) *	1970-03-11	1972-11-30	Sandoz Ag	Verfahren zur Herstellung neuer Benzocycloheptathiophene
BE789822A (fr) *	1971-10-08	1973-04-06	Allen & Hanburys Ltd	Nouveaux composes heterocycliques

1974
- 1974-08-20 CA CA207,416A patent/CA1041100A/fr not_active Expired
- 1974-08-28 GB GB3753374A patent/GB1436304A/en not_active Expired
- 1974-09-10 ZA ZA00745754A patent/ZA745754B/xx unknown
- 1974-09-20 DE DE2445002A patent/DE2445002C2/de not_active Expired
- 1974-09-23 CH CH1282474A patent/CH605767A5/xx not_active IP Right Cessation
- 1974-10-03 FR FR7433394A patent/FR2247237B1/fr not_active Expired
- 1974-10-03 NL NLAANVRAGE7413053,A patent/NL179110C/xx not_active IP Right Cessation
- 1974-10-04 BE BE149229A patent/BE820723A/fr not_active IP Right Cessation
- 1974-10-04 JP JP49114632A patent/JPS603060B2/ja not_active Expired

Also Published As

Publication number	Publication date
GB1436304A (en)	1976-05-19
CH605767A5 (fr)	1978-10-13
NL7413053A (nl)	1975-04-08
NL179110C (nl)	1986-07-16
BE820723A (fr)	1975-04-04
FR2247237A1 (fr)	1975-05-09
JPS603060B2 (ja)	1985-01-25
ZA745754B (en)	1975-10-29
FR2247237B1 (fr)	1978-07-21
JPS5062979A (fr)	1975-05-29
DE2445002A1 (de)	1975-04-10
DE2445002C2 (de)	1984-11-22
NL179110B (nl)	1986-02-17

Publication	Publication Date	Title
US3993679A (en)	1976-11-23	Cyano phenylene dioxamic molecules
US2910488A (en)	1959-10-27	Aniline derivatives
Santilli et al.	1987	2-Oxo-1, 8-naphthyridine-3-carboxylic acid derivatives with potent gastric antisecretory properties
PL111422B1 (en)	1980-08-30	Process for the preparation of novel derivatives of quinazolone
US3953468A (en)	1976-04-27	3-Cyano thiophen-2-yl oxamic acid and derivatives
US4207327A (en)	1980-06-10	N-(4-Pyrazolidinyl)benzamides and their amino precursors
US3465001A (en)	1969-09-02	Maleimido aryloxy alkanoic acids,alkyl esters and amides thereof
US4128570A (en)	1978-12-05	Anti-allergic oxanil compounds
US4095028A (en)	1978-06-13	Substituted dioxamic acid esters
CA1041100A (fr)	1978-10-24	Acide pyridine-diyldioxamique
US4091011A (en)	1978-05-23	3-Cyano-oxanilic acid derivatives
US4147694A (en)	1979-04-03	8-(1H-Tetrazol-5-yl-carbamoyl)quinoline compounds
CA1118781A (fr)	1982-02-23	Acides 2-benzothiazolyl-oxamiques et leurs esters
US3982006A (en)	1976-09-21	M-Phenylene dioxamic acid derivatives
US3963660A (en)	1976-06-15	Pyridine dioxamic acids and esters
US4119783A (en)	1978-10-10	3'Lower alkylcarbonyl oxanilic acid esters
US3972911A (en)	1976-08-03	N,N'(Cyano-phenylene)dioxamic acids and esters
US4159278A (en)	1979-06-26	Dioxamic acids and salts
KR960016123B1 (ko)	1996-12-04	디-t-부틸페닐 알킬 및 벤질 에테르류
US4017538A (en)	1977-04-12	Alkyl thio sulfinyl and sulfonyl oxamic compounds, compositions and methods of use
US4067995A (en)	1978-01-10	Compounds, compositions and methods of use
US4792547A (en)	1988-12-20	Pyrazine-2-carboxamide derivatives useful in treating allergic disease
US4038398A (en)	1977-07-26	Compounds, compositions and methods of use
US4011337A (en)	1977-03-08	Oxamide-oxamic compounds, compositions and methods of use
US4169153A (en)	1979-09-25	Anti-allergic oxanilates