CA1039743A - M-phenylene dioxamates - Google Patents
M-phenylene dioxamatesInfo
- Publication number
- CA1039743A CA1039743A CA226,801A CA226801A CA1039743A CA 1039743 A CA1039743 A CA 1039743A CA 226801 A CA226801 A CA 226801A CA 1039743 A CA1039743 A CA 1039743A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- phenylene
- cyano
- dioxamate
- phenyl
- 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.)
- Expired
Links
- LLYLFRMAWHTFRY-UHFFFAOYSA-N (3-oxamoyloxyphenyl) 2-amino-2-oxoacetate Chemical class NC(=O)C(=O)OC1=CC=CC(OC(=O)C(N)=O)=C1 LLYLFRMAWHTFRY-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims description 73
- -1 oxalyl halide Chemical class 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229950001656 dioxamate Drugs 0.000 claims description 26
- 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 25
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- AJYCIEHSLYUBEI-UHFFFAOYSA-N 3,5-diamino-4-chlorobenzonitrile Chemical compound NC1=CC(C#N)=CC(N)=C1Cl AJYCIEHSLYUBEI-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 5
- RVGLGHVJXCETIO-UHFFFAOYSA-N lodoxamide Chemical compound OC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(O)=O)=C1Cl RVGLGHVJXCETIO-UHFFFAOYSA-N 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- YOZSRQSUXWJLEU-UHFFFAOYSA-N benzyl 2-chloro-2-oxoacetate Chemical compound ClC(=O)C(=O)OCC1=CC=CC=C1 YOZSRQSUXWJLEU-UHFFFAOYSA-N 0.000 claims description 3
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims description 2
- BVBOCMOAHOFXRH-UHFFFAOYSA-N benzyl 2-[2-chloro-5-cyano-3-[(2-oxo-2-phenylmethoxyacetyl)amino]anilino]-2-oxoacetate Chemical compound C1=C(C#N)C=C(NC(=O)C(=O)OCC=2C=CC=CC=2)C(Cl)=C1NC(=O)C(=O)OCC1=CC=CC=C1 BVBOCMOAHOFXRH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- KCRAPMZHZAQFQQ-UHFFFAOYSA-N hexyl 2-[2-chloro-5-cyano-3-[(2-hexoxy-2-oxoacetyl)amino]anilino]-2-oxoacetate Chemical compound CCCCCCOC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(=O)OCCCCCC)=C1Cl KCRAPMZHZAQFQQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 150000001768 cations Chemical class 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 150000004986 phenylenediamines Chemical class 0.000 claims 3
- ZJHIOQXMVPYQRS-UHFFFAOYSA-N 2-[2-chloro-5-cyano-3-[(2-hexoxy-2-oxoacetyl)amino]anilino]-2-oxoacetic acid Chemical compound CCCCCCOC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(O)=O)=C1Cl ZJHIOQXMVPYQRS-UHFFFAOYSA-N 0.000 claims 2
- PMWTVXDADWGXFH-UHFFFAOYSA-N 2-[2-chloro-5-cyano-3-[(2-oxo-2-phenylmethoxyacetyl)amino]anilino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(=O)OCC=2C=CC=CC=2)=C1Cl PMWTVXDADWGXFH-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OKICDJDUMRLDED-UHFFFAOYSA-N 2-chloro-5-phenylbenzene-1,3-diamine Chemical compound NC1=C(Cl)C(N)=CC(C=2C=CC=CC=2)=C1 OKICDJDUMRLDED-UHFFFAOYSA-N 0.000 claims 1
- FVBSALGAUYNXPW-UHFFFAOYSA-N butyl 2-[3-[(2-butoxy-2-oxoacetyl)amino]-2-chloro-5-cyanoanilino]-2-oxoacetate Chemical compound CCCCOC(=O)C(=O)NC1=CC(C#N)=CC(NC(=O)C(=O)OCCCC)=C1Cl FVBSALGAUYNXPW-UHFFFAOYSA-N 0.000 claims 1
- MDDCGNNWRJQKLY-UHFFFAOYSA-N ethyl 2-[2-chloro-3-[(2-ethoxy-2-oxoacetyl)amino]-5-phenylanilino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=C(Cl)C(NC(=O)C(=O)OCC)=CC(C=2C=CC=CC=2)=C1 MDDCGNNWRJQKLY-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 239000000446 fuel Substances 0.000 abstract 2
- 230000000153 supplemental effect Effects 0.000 abstract 2
- 235000009421 Myristica fragrans Nutrition 0.000 abstract 1
- 241000605112 Scapanulus oweni Species 0.000 abstract 1
- 239000008246 gaseous mixture Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000001115 mace Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 18
- 239000000843 powder Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 229960004756 ethanol Drugs 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000003380 propellant Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 241000700159 Rattus Species 0.000 description 6
- 208000006673 asthma Diseases 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 229940008126 aerosol Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 206010002198 Anaphylactic reaction Diseases 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- 208000026935 allergic disease Diseases 0.000 description 4
- 230000007815 allergy Effects 0.000 description 4
- 208000003455 anaphylaxis Diseases 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- 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 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 2
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 2
- VYLDBYOSHBXGNF-UHFFFAOYSA-N 2-oxo-2-phenylmethoxyacetic acid Chemical compound OC(=O)C(=O)OCC1=CC=CC=C1 VYLDBYOSHBXGNF-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 208000004262 Food Hypersensitivity Diseases 0.000 description 2
- 206010016946 Food allergy Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
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- 150000001408 amides Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
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- 108091007433 antigens Proteins 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 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
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 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
- 238000001816 cooling Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000020932 food allergy Nutrition 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000008024 pharmaceutical diluent Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000006215 rectal suppository Substances 0.000 description 2
- 206010039083 rhinitis Diseases 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/477,816 US3972911A (en) | 1973-07-26 | 1974-06-10 | N,N'(Cyano-phenylene)dioxamic acids and esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1039743A true CA1039743A (en) | 1978-10-03 |
Family
ID=23897482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,801A Expired CA1039743A (en) | 1974-06-10 | 1975-05-13 | M-phenylene dioxamates |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5929066B2 (en:Method) |
| BE (1) | BE830071A (en:Method) |
| CA (1) | CA1039743A (en:Method) |
| CH (1) | CH618420A5 (en:Method) |
| DE (1) | DE2525164C2 (en:Method) |
| FR (1) | FR2273524A1 (en:Method) |
| GB (1) | GB1489702A (en:Method) |
| ZA (1) | ZA753106B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1181070A (en) * | 1979-11-28 | 1985-01-15 | Kiyoshi Murase | Process of producing 2-hydroxyoxanilic acid derivatives |
| DE3229539A1 (de) * | 1982-08-07 | 1984-02-09 | Basf Ag, 6700 Ludwigshafen | Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH500260A (de) * | 1967-05-16 | 1971-01-29 | Ciba Geigy Ag | Verwendung von Bis-oxalsäure-esteramiden als Stabilisierungsmittel ausserhalb der Textilindustrie |
-
1975
- 1975-05-13 CA CA226,801A patent/CA1039743A/en not_active Expired
- 1975-05-14 ZA ZA00753106A patent/ZA753106B/xx unknown
- 1975-06-02 GB GB23817/75A patent/GB1489702A/en not_active Expired
- 1975-06-06 DE DE2525164A patent/DE2525164C2/de not_active Expired
- 1975-06-09 FR FR7517978A patent/FR2273524A1/fr active Granted
- 1975-06-10 BE BE157193A patent/BE830071A/xx not_active IP Right Cessation
- 1975-06-10 JP JP50070087A patent/JPS5929066B2/ja not_active Expired
- 1975-06-10 CH CH748575A patent/CH618420A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2525164C2 (de) | 1986-10-16 |
| JPS518225A (en:Method) | 1976-01-23 |
| FR2273524B1 (en:Method) | 1979-08-10 |
| DE2525164A1 (de) | 1975-12-18 |
| BE830071A (fr) | 1975-12-10 |
| AU8128575A (en) | 1976-11-25 |
| JPS5929066B2 (ja) | 1984-07-18 |
| ZA753106B (en) | 1976-04-28 |
| CH618420A5 (en) | 1980-07-31 |
| GB1489702A (en) | 1977-10-26 |
| FR2273524A1 (fr) | 1976-01-02 |
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