CH593921A5 - 3,5-Bis-(salicylamido)-benzoic acid derivs - which inhibit immuno-reactions and have sedative, anti-pyretic, anti-inflammatory and anti-allergic activity - Google Patents

3,5-Bis-(salicylamido)-benzoic acid derivs - which inhibit immuno-reactions and have sedative, anti-pyretic, anti-inflammatory and anti-allergic activity

Info

Publication number: CH593921A5
Authority: CH; Switzerland
Prior art keywords: sep; acid; formula; bis; compound
Prior art date: 1973-03-27

Application number

CH423274A

Other languages

German (de)

English (en)

Original Assignee

Chugai Pharmaceutical Co Ltd

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.)

1973-03-27

Filing date

1974-03-27

Publication date

1977-12-30

1974-03-27 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1977-12-30 Publication of CH593921A5 publication Critical patent/CH593921A5/de

Links

XQQBEHSIRQMAIT-UHFFFAOYSA-N 3,5-bis[(2-hydroxybenzoyl)amino]benzoic acid Chemical compound C=1C(NC(=O)C=2C(=CC=CC=2)O)=CC(C(=O)O)=CC=1NC(=O)C1=CC=CC=C1O XQQBEHSIRQMAIT-UHFFFAOYSA-N 0.000 title description 3
230000003266 anti-allergic effect Effects 0.000 title description 2
230000003110 anti-inflammatory effect Effects 0.000 title description 2
230000001754 anti-pyretic effect Effects 0.000 title description 2
239000002221 antipyretic Substances 0.000 title description 2
230000036046 immunoreaction Effects 0.000 title 1
239000000932 sedative agent Substances 0.000 title 1
230000001624 sedative effect Effects 0.000 title 1
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
235000011056 potassium acetate Nutrition 0.000 claims description 5
229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
239000001632 sodium acetate Substances 0.000 claims description 4
235000017281 sodium acetate Nutrition 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 2
239000001639 calcium acetate Substances 0.000 claims description 2
235000011092 calcium acetate Nutrition 0.000 claims description 2
229960005147 calcium acetate Drugs 0.000 claims description 2
229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
235000010216 calcium carbonate Nutrition 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
235000011181 potassium carbonates Nutrition 0.000 claims description 2
235000017550 sodium carbonate Nutrition 0.000 claims description 2
235000011121 sodium hydroxide Nutrition 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 11
230000010933 acylation Effects 0.000 abstract description 2
238000005917 acylation reaction Methods 0.000 abstract description 2
125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 abstract 1
125000002252 acyl group Chemical group 0.000 abstract 1
230000007062 hydrolysis Effects 0.000 abstract 1
238000006460 hydrolysis reaction Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 30
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
230000005764 inhibitory process Effects 0.000 description 19
239000013078 crystal Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
206010018910 Haemolysis Diseases 0.000 description 12
230000008588 hemolysis Effects 0.000 description 12
239000000725 suspension Substances 0.000 description 11
LDQMZKBIBRAZEA-UHFFFAOYSA-N 2,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 10
DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 8
150000004702 methyl esters Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
229940086542 triethylamine Drugs 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
230000000295 complement effect Effects 0.000 description 6
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
229960004889 salicylic acid Drugs 0.000 description 5
239000000523 sample Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
210000003743 erythrocyte Anatomy 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
FWJFNQHPFXHOAC-UHFFFAOYSA-N methyl 2,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1N FWJFNQHPFXHOAC-UHFFFAOYSA-N 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
JJMMIBYSZFGSEB-UHFFFAOYSA-N 2,4-bis[(2-acetyloxybenzoyl)amino]benzoic acid Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=CC=C(C(O)=O)C(NC(=O)C=2C(=CC=CC=2)OC(C)=O)=C1 JJMMIBYSZFGSEB-UHFFFAOYSA-N 0.000 description 3
XEWSQYFENCJRBH-UHFFFAOYSA-N 2,4-bis[(2-hydroxybenzoyl)amino]benzoic acid Chemical compound C1=C(NC(=O)C=2C(=CC=CC=2)O)C(C(=O)O)=CC=C1NC(=O)C1=CC=CC=C1O XEWSQYFENCJRBH-UHFFFAOYSA-N 0.000 description 3
RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 3
RSCMSACQRPYYRN-UHFFFAOYSA-N 3,5-diaminobenzamide Chemical compound NC(=O)C1=CC(N)=CC(N)=C1 RSCMSACQRPYYRN-UHFFFAOYSA-N 0.000 description 3
UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
MYHGMWDKFGQECW-UHFFFAOYSA-N ethyl 2,4-diaminobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1N MYHGMWDKFGQECW-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
VBPWYDATKAEZSI-UHFFFAOYSA-N 2,4-diaminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1N VBPWYDATKAEZSI-UHFFFAOYSA-N 0.000 description 2
TZOAXDSPIBONLW-UHFFFAOYSA-N 2,5-bis[(2-acetyloxybenzoyl)amino]benzoic acid Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC2=CC(=C(C=C2)NC(=O)C3=CC=CC=C3OC(=O)C)C(=O)O TZOAXDSPIBONLW-UHFFFAOYSA-N 0.000 description 2
WURCAQBIEYOSIZ-UHFFFAOYSA-N 2,5-bis[(2-hydroxybenzoyl)amino]benzoic acid Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)O)C(C(=O)O)=CC=1NC(=O)C1=CC=CC=C1O WURCAQBIEYOSIZ-UHFFFAOYSA-N 0.000 description 2
MDKAAWDKKBFSTK-UHFFFAOYSA-N 2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=CC=C1C(Cl)=O MDKAAWDKKBFSTK-UHFFFAOYSA-N 0.000 description 2
HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241001494479 Pecora Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QTTMJOLTEHSNRK-UHFFFAOYSA-N [2-[[3-[(2-acetyloxybenzoyl)amino]-5-carbamoylphenyl]carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=CC(NC(=O)C=2C(=CC=CC=2)OC(C)=O)=CC(C(N)=O)=C1 QTTMJOLTEHSNRK-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 2
229960003464 mefenamic acid Drugs 0.000 description 2
HMRIHHGEDFBARU-UHFFFAOYSA-N methyl 2,4-bis[(2-methoxybenzoyl)amino]benzoate Chemical compound C1=C(NC(=O)C=2C(=CC=CC=2)OC)C(C(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1OC HMRIHHGEDFBARU-UHFFFAOYSA-N 0.000 description 2
HRZXQRHIENGYTL-UHFFFAOYSA-N methyl 2,5-diaminobenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1N HRZXQRHIENGYTL-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229960002895 phenylbutazone Drugs 0.000 description 2
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000012085 test solution Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
XXSHHUIMCUKAQT-UHFFFAOYSA-N 2,3-dibenzamidobenzoic acid Chemical class C=1C=CC=CC=1C(=O)NC=1C(C(=O)O)=CC=CC=1NC(=O)C1=CC=CC=C1 XXSHHUIMCUKAQT-UHFFFAOYSA-N 0.000 description 1
MGVSMWAKNOOSKA-UHFFFAOYSA-N 2,4-bis[(2-ethoxybenzoyl)amino]benzoic acid Chemical compound CCOC1=CC=CC=C1C(=O)NC1=CC=C(C(O)=O)C(NC(=O)C=2C(=CC=CC=2)OCC)=C1 MGVSMWAKNOOSKA-UHFFFAOYSA-N 0.000 description 1
HGBGKOXLUTYONU-UHFFFAOYSA-N 2,4-bis[(2-methoxybenzoyl)amino]benzoic acid Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(C(O)=O)C(NC(=O)C=2C(=CC=CC=2)OC)=C1 HGBGKOXLUTYONU-UHFFFAOYSA-N 0.000 description 1
UONVFNLDGRWLKF-UHFFFAOYSA-N 2,5-diaminobenzoic acid Chemical compound NC1=CC=C(N)C(C(O)=O)=C1 UONVFNLDGRWLKF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
BDPARNTXGNJTCC-UHFFFAOYSA-N 2-butoxybenzoyl chloride Chemical compound CCCCOC1=CC=CC=C1C(Cl)=O BDPARNTXGNJTCC-UHFFFAOYSA-N 0.000 description 1
XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
NOAMGDCYWBSEKH-UHFFFAOYSA-N 3,4-bis[(2-hydroxybenzoyl)amino]benzoic acid Chemical compound C=1C=CC=C(O)C=1C(=O)NC1=CC(C(=O)O)=CC=C1NC(=O)C1=CC=CC=C1O NOAMGDCYWBSEKH-UHFFFAOYSA-N 0.000 description 1
CJTDHFCGKYZUJK-UHFFFAOYSA-N 3,5-bis[(2-acetyloxybenzoyl)amino]benzoic acid Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=CC(NC(=O)C=2C(=CC=CC=2)OC(C)=O)=CC(C(O)=O)=C1 CJTDHFCGKYZUJK-UHFFFAOYSA-N 0.000 description 1
SPQQJSDIHMRLJX-UHFFFAOYSA-N 3,5-bis[(2-methoxybenzoyl)amino]benzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC(NC(=O)C=2C(=CC=CC=2)OC)=CC(C(N)=O)=C1 SPQQJSDIHMRLJX-UHFFFAOYSA-N 0.000 description 1
BIQJZLNDWWJJIP-UHFFFAOYSA-N 3,5-bis[(2-methoxybenzoyl)amino]benzoic acid Chemical compound COC1=CC=CC=C1C(=O)NC1=CC(NC(=O)C=2C(=CC=CC=2)OC)=CC(C(O)=O)=C1 BIQJZLNDWWJJIP-UHFFFAOYSA-N 0.000 description 1
MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
QCESOQYTNNRNNY-UHFFFAOYSA-N 4-bromo-3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC(F)=C1Br QCESOQYTNNRNNY-UHFFFAOYSA-N 0.000 description 1
SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
ZYMPZCXBHDRBCT-UHFFFAOYSA-N [(2-acetyloxybenzoyl)amino] benzoate Chemical compound C(C1=CC=CC=C1)(=O)ONC(C1=C(C=CC=C1)OC(C)=O)=O ZYMPZCXBHDRBCT-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229960000333 benzydamine Drugs 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000012490 blank solution Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
VZRKXVWDZNNCII-UHFFFAOYSA-N butyl 2,4-bis[(2-acetyloxybenzoyl)amino]benzoate Chemical compound C1=C(NC(=O)C=2C(=CC=CC=2)OC(C)=O)C(C(=O)OCCCC)=CC=C1NC(=O)C1=CC=CC=C1OC(C)=O VZRKXVWDZNNCII-UHFFFAOYSA-N 0.000 description 1
UAXFJPLDVYZPJV-UHFFFAOYSA-N butyl 2,4-diaminobenzoate Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1N UAXFJPLDVYZPJV-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 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
LQPGGJRYWJOKPE-UHFFFAOYSA-N ethyl 2,4-bis[(2-butoxybenzoyl)amino]benzoate Chemical compound CCCCOC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)OCC)C(NC(=O)C=2C(=CC=CC=2)OCCCC)=C1 LQPGGJRYWJOKPE-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
PPEOZGFXFVZDOW-UHFFFAOYSA-N methyl 2,4-bis[(2-acetyloxybenzoyl)amino]benzoate Chemical compound C1=C(NC(=O)C=2C(=CC=CC=2)OC(C)=O)C(C(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1OC(C)=O PPEOZGFXFVZDOW-UHFFFAOYSA-N 0.000 description 1
TZJWLTPLXUVJED-UHFFFAOYSA-N methyl 2,5-bis[(2-acetyloxybenzoyl)amino]benzoate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)OC(C)=O)C(C(=O)OC)=CC=1NC(=O)C1=CC=CC=C1OC(C)=O TZJWLTPLXUVJED-UHFFFAOYSA-N 0.000 description 1
ITARYZCWWXCXLL-UHFFFAOYSA-N methyl 2,5-bis[(2-hydroxybenzoyl)amino]benzoate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)O)C(C(=O)OC)=CC=1NC(=O)C1=CC=CC=C1O ITARYZCWWXCXLL-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
YIVBGQCRICXGCH-UHFFFAOYSA-N n'-benzoyl-2-methoxybenzohydrazide Chemical compound COC1=CC=CC=C1C(=O)NNC(=O)C1=CC=CC=C1 YIVBGQCRICXGCH-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
230000012177 negative regulation of immune response Effects 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000013074 reference sample Substances 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH423274A 1973-03-27 1974-03-27 3,5-Bis-(salicylamido)-benzoic acid derivs - which inhibit immuno-reactions and have sedative, anti-pyretic, anti-inflammatory and anti-allergic activity CH593921A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3415273A JPS5715585B2 (fr)	1973-03-27	1973-03-27

Publications (1)

Publication Number	Publication Date
CH593921A5 true CH593921A5 (en)	1977-12-30

Family

ID=12406215

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH423274A CH593921A5 (en)	1973-03-27	1974-03-27	3,5-Bis-(salicylamido)-benzoic acid derivs - which inhibit immuno-reactions and have sedative, anti-pyretic, anti-inflammatory and anti-allergic activity

Country Status (12)

Country	Link
JP (1)	JPS5715585B2 (fr)
AR (1)	AR206399A1 (fr)
BE (1)	BE812869A (fr)
CH (1)	CH593921A5 (fr)
CS (1)	CS168472B2 (fr)
DK (1)	DK142543B (fr)
ES (1)	ES424668A1 (fr)
HU (1)	HU167255B (fr)
MX (1)	MX3089E (fr)
NL (1)	NL7404022A (fr)
SE (1)	SE406463B (fr)
SU (1)	SU560530A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006098308A1 (fr) *	2005-03-16	2006-09-21	Toyama Chemical Co., Ltd.	Nouveau dérivé de l'acide anthranilique ou sel de celui-ci

1973
- 1973-03-27 JP JP3415273A patent/JPS5715585B2/ja not_active Expired
1974
- 1974-01-01 AR AR252926A patent/AR206399A1/es active
- 1974-03-25 HU HUCU143A patent/HU167255B/hu unknown
- 1974-03-26 SU SU2008059A patent/SU560530A3/ru active
- 1974-03-26 SE SE747404081A patent/SE406463B/xx unknown
- 1974-03-26 CS CS2174*BA patent/CS168472B2/cs unknown
- 1974-03-26 NL NL7404022A patent/NL7404022A/xx unknown
- 1974-03-26 DK DK166774AA patent/DK142543B/da unknown
- 1974-03-26 ES ES424668A patent/ES424668A1/es not_active Expired
- 1974-03-27 MX MX001923U patent/MX3089E/es unknown
- 1974-03-27 CH CH423274A patent/CH593921A5/de not_active IP Right Cessation
- 1974-03-27 BE BE2053507A patent/BE812869A/fr unknown

Also Published As

Publication number	Publication date
NL7404022A (fr)	1974-10-01
SE406463B (sv)	1979-02-12
AR206399A1 (es)	1976-07-23
JPS49117442A (fr)	1974-11-09
BE812869A (fr)	1974-07-15
DK142543C (fr)	1981-07-20
ES424668A1 (es)	1976-06-01
SU560530A3 (ru)	1977-05-30
CS168472B2 (fr)	1976-06-29
MX3089E (es)	1980-03-31
HU167255B (fr)	1975-09-27
DK142543B (da)	1980-11-17
JPS5715585B2 (fr)	1982-03-31

Legal Events

Date	Code	Title	Description
1982-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2611690C2 (fr)	1992-01-16
CH615152A5 (en)	1980-01-15	Process for the preparation of carboxylic acid amides and the carboxylic acid amides thus prepared
EP0019726B1 (fr)	1984-09-26	N-Azidosulfonylaryl-maléimides et leur utilisation
DE2541342A1 (de)	1977-03-31	Neue phenoxyalkylcarbonsaeuren und verfahren zur herstellung derselben
CH621780A5 (fr)	1981-02-27
DD289526A5 (de)	1991-05-02	Neue chemische prozesse
CH635065A5 (de)	1983-03-15	Verfahren zum trennen von gemischen aus 3- und 4-nitrophthalsaeure.
DE2535930C3 (de)	1978-09-21	Abietinsaureamidderivate und Verfahren zu ihrer Herstellung
CH593921A5 (en)	1977-12-30	3,5-Bis-(salicylamido)-benzoic acid derivs - which inhibit immuno-reactions and have sedative, anti-pyretic, anti-inflammatory and anti-allergic activity
DE657526C (de)	1938-03-07	Verfahren zur Herstellung von Estern der 9-Oxyfluorencarbonsaeure-(9)
AT209895B (de)	1960-06-25	Verfahren zur Herstellung von 3-Amino-2,4,6-trijodbenzoylverbindungen
DE2521040C3 (de)	1982-02-04	p-Iobutylhydratropasäure-(4-acetamidophenyl)-ester und Verfarhen zu dessen Herstellung
CH630342A5 (en)	1982-06-15	Process for the preparation of novel cyanoacetic acid anilide derivatives.
CH498135A (de)	1970-10-31	Verfahren zur Herstellung von neuen Furazanderivaten
DE2814974A1 (de)	1978-10-19	Neue n hoch 2 -t-butyl-11a-halo-6-demethyl-6-desoxy-6-methylen-tetracycline und verfahren zu ihrer herstellung
DE936747C (de)	1955-12-22	Verfahren zur Herstellung von neuen Pyrimidinderivaten und deren Salzen
DE2414799A1 (de)	1974-10-10	Bis-(benzamido)-benzoesaeure-derivate, verfahren zu ihrer herstellung und arzneimittel
CH345016A (de)	1960-03-15	Verfahren zur Herstellung von p-Oxy-phenylamiden
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon
AT204047B (de)	1959-06-25	Verfahren zur Herstellung neuer Triazine
AT371457B (de)	1983-06-27	Verfahren zur herstellung von neuen 6-substituierten pyranon-verbindungen
DE960538C (de)	1957-03-21	Verfahren zur Herstellung von 5-Benzyloxy-ª, 2-dinitrostyrolen
DE1900948C (de)	1971-09-23	Cis- und trans-2-Methyl-5-(3, 4, S-trimethoxybenzamidoJ-decahydroisochinolin
AT209007B (de)	1960-05-10	Verfahren zur Herstellung von 9 α-Halogen-4-pregnen-16 α, 17 α,21-triol-3, 11, 20-trionen und ihren Estern
DE2302671A1 (de)	1973-07-26	5-acylpyrrole, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln