NO762170L - - Google Patents

Info

Publication number: NO762170L
Authority: NO; Norway
Prior art keywords: alkoxy; compounds; azide; methoxy; compound
Prior art date: 1975-07-10

Application number

NO762170A

Other languages

English (en)

Norwegian (no)

Inventor

J S Bindra

Original Assignee

Pfizer

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.)

1975-07-10

Filing date

1976-06-23

Publication date

1977-01-11

1976-06-23 Application filed by Pfizer filed Critical Pfizer

1977-01-11 Publication of NO762170L publication Critical patent/NO762170L/no

Links

150000001875 compounds Chemical class 0.000 claims description 45
238000000034 method Methods 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
-1 benzyloxy, hydroxy Chemical group 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 6
150000001540 azides Chemical class 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
238000005658 halogenation reaction Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 description 27
238000012360 testing method Methods 0.000 description 18
208000003455 anaphylaxis Diseases 0.000 description 17
239000000243 solution Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
241001465754 Metazoa Species 0.000 description 16
241000700159 Rattus Species 0.000 description 16
239000004480 active ingredient Substances 0.000 description 16
230000000694 effects Effects 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
206010002198 Anaphylactic reaction Diseases 0.000 description 15
230000036783 anaphylactic response Effects 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
229940079593 drug Drugs 0.000 description 10
239000003814 drug Substances 0.000 description 10
210000002784 stomach Anatomy 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002775 capsule Substances 0.000 description 9
238000011282 treatment Methods 0.000 description 9
206010020751 Hypersensitivity Diseases 0.000 description 8
239000007787 solid Substances 0.000 description 8
229940027941 immunoglobulin g Drugs 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
CNGRGEDXKHIFIL-UHFFFAOYSA-N 2-chloro-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(Cl)=NC(=O)C2=C1 CNGRGEDXKHIFIL-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
108060003951 Immunoglobulin Proteins 0.000 description 5
208000008469 Peptic Ulcer Diseases 0.000 description 5
230000000172 allergic effect Effects 0.000 description 5
239000000427 antigen Substances 0.000 description 5
102000036639 antigens Human genes 0.000 description 5
108091007433 antigens Proteins 0.000 description 5
208000010668 atopic eczema Diseases 0.000 description 5
239000002585 base Substances 0.000 description 5
102000018358 immunoglobulin Human genes 0.000 description 5
230000001404 mediated effect Effects 0.000 description 5
241000282412 Homo Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
208000026935 allergic disease Diseases 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
230000037396 body weight Effects 0.000 description 4
229940124630 bronchodilator Drugs 0.000 description 4
230000004856 capillary permeability Effects 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-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
RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 3
206010017865 Gastritis erosive Diseases 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
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 3
108010058846 Ovalbumin Proteins 0.000 description 3
208000025865 Ulcer Diseases 0.000 description 3
210000001015 abdomen Anatomy 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
230000007815 allergy Effects 0.000 description 3
239000003699 antiulcer agent Substances 0.000 description 3
229960000530 carbenoxolone Drugs 0.000 description 3
229960002252 carbenoxolone sodium Drugs 0.000 description 3
230000008602 contraction Effects 0.000 description 3
229960000265 cromoglicic acid Drugs 0.000 description 3
VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
239000000975 dye Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000006199 nebulizer Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000000069 prophylactic effect Effects 0.000 description 3
239000000376 reactant Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
231100000397 ulcer Toxicity 0.000 description 3
MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 2
XRXQKKAWSWPYET-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-7-propoxyquinazoline Chemical compound ClC1=NC(Cl)=C2C=C(OC)C(OCCC)=CC2=N1 XRXQKKAWSWPYET-UHFFFAOYSA-N 0.000 description 2
YBFCRZQWPDJGHL-UHFFFAOYSA-N 6-methoxy-7-propoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=C(OCCC)C(OC)=C2 YBFCRZQWPDJGHL-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
208000007107 Stomach Ulcer Diseases 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
201000009961 allergic asthma Diseases 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
239000000168 bronchodilator agent Substances 0.000 description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
208000000718 duodenal ulcer Diseases 0.000 description 2
210000003238 esophagus Anatomy 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
230000027119 gastric acid secretion Effects 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
208000021760 high fever Diseases 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000000521 hyperimmunizing effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
239000003380 propellant Substances 0.000 description 2
210000001187 pylorus Anatomy 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 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
238000005303 weighing Methods 0.000 description 2
WNAJXPYVTFYEST-UHFFFAOYSA-N 2-Amino-3-methylbenzoate Chemical compound CC1=CC=CC(C(O)=O)=C1N WNAJXPYVTFYEST-UHFFFAOYSA-N 0.000 description 1
CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
LZEUVRRBTRQDSB-UHFFFAOYSA-N 2-amino-4-methoxy-3-propoxybenzoic acid Chemical compound CCCOC1=C(N)C(C(O)=O)=CC=C1OC LZEUVRRBTRQDSB-UHFFFAOYSA-N 0.000 description 1
SMINANAUHAQEJM-UHFFFAOYSA-N 2-chloro-6-methoxy-7-propoxy-1h-quinazolin-4-one Chemical compound N1=C(Cl)NC(=O)C2=C1C=C(OCCC)C(OC)=C2 SMINANAUHAQEJM-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
CPIAGPJMSBBTDR-UHFFFAOYSA-N 8,9-dimethoxy-6H-tetrazolo[1,5-c]quinazolin-5-one Chemical compound N1C(=O)N2N=NN=C2C2=C1C=C(OC)C(OC)=C2 CPIAGPJMSBBTDR-UHFFFAOYSA-N 0.000 description 1
WFDHXKXFTSQIMG-UHFFFAOYSA-N 8-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C(C)=CC=C2 WFDHXKXFTSQIMG-UHFFFAOYSA-N 0.000 description 1
FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002199 Anaphylactic shock Diseases 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
208000014181 Bronchial disease 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
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000700198 Cavia Species 0.000 description 1
WFZKRNIMSVDNBU-UHFFFAOYSA-N Creatinine sulfate mixture with serotonin Chemical compound [O-]S([O-])(=O)=O.C[NH+]1CC(=O)N=C1N.C1=C(O)C=C2C(CC[NH3+])=CNC2=C1 WFZKRNIMSVDNBU-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
238000000585 Mann–Whitney U test Methods 0.000 description 1
206010028735 Nasal congestion Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
208000036071 Rhinorrhea Diseases 0.000 description 1
206010039101 Rhinorrhoea Diseases 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000000150 Sympathomimetic Substances 0.000 description 1
241000906446 Theraps Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
206010045240 Type I hypersensitivity Diseases 0.000 description 1
206010047924 Wheezing Diseases 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
208000030961 allergic reaction Diseases 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
230000002686 anti-diuretic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
229940124538 antidiuretic agent Drugs 0.000 description 1
239000003160 antidiuretic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
208000027744 congestion Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 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
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
229960003720 enoxolone Drugs 0.000 description 1
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000000762 glandular Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000035876 healing Effects 0.000 description 1
229960004931 histamine dihydrochloride Drugs 0.000 description 1
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
230000035874 hyperreactivity Effects 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
230000000984 immunochemical effect Effects 0.000 description 1
230000002163 immunogen Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
239000006187 pill Substances 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
239000004926 polymethyl methacrylate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
150000008515 quinazolinediones Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
206010041232 sneezing Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WZODLFCLKIXWGA-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)C)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] WZODLFCLKIXWGA-UHFFFAOYSA-N 0.000 description 1
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
235000010378 sodium ascorbate Nutrition 0.000 description 1
229960005055 sodium ascorbate Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems

Landscapes

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

NO762170A 1975-07-10 1976-06-23 NO762170L (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US59476575A	1975-07-10	1975-07-10
US65325076A	1976-01-28	1976-01-28

Publications (1)

Publication Number	Publication Date
NO762170L true NO762170L (es)	1977-01-11

Family

ID=27082077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO762170A NO762170L (es)	1975-07-10	1976-06-23

Country Status (20)

Country	Link
JP (1)	JPS5210297A (es)
AR (1)	AR211272A1 (es)
AU (1)	AU1515776A (es)
DD (1)	DD126326A5 (es)
DE (1)	DE2630053C3 (es)
DK (1)	DK143704C (es)
ES (1)	ES449570A1 (es)
FI (1)	FI762013A (es)
FR (1)	FR2316952A1 (es)
GB (1)	GB1499255A (es)
GR (1)	GR60543B (es)
IE (1)	IE43466B1 (es)
IL (1)	IL49850A0 (es)
LU (1)	LU75342A1 (es)
NL (1)	NL166024C (es)
NO (1)	NO762170L (es)
PH (1)	PH15280A (es)
PT (1)	PT65337B (es)
RO (1)	RO71662B (es)
SE (1)	SE7606762L (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2007261982A (ja) *	2006-03-28	2007-10-11	Mitsubishi Gas Chem Co Inc	キナゾリン−２，４−ジオン誘導体の製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1519765A (en) *	1974-09-05	1978-08-02	Ici Ltd	Pesticidal dihydrotetrazolo(1,5a) quinazolines compositions and processes

1976
- 1976-04-21 IE IE836/76A patent/IE43466B1/en unknown
- 1976-06-14 SE SE7606762A patent/SE7606762L/xx unknown
- 1976-06-19 GR GR51048A patent/GR60543B/el unknown
- 1976-06-21 IL IL49850A patent/IL49850A0/xx unknown
- 1976-06-23 AU AU15157/76A patent/AU1515776A/en not_active Expired
- 1976-06-23 NO NO762170A patent/NO762170L/no unknown
- 1976-06-28 PH PH18616A patent/PH15280A/en unknown
- 1976-07-01 GB GB27543/76A patent/GB1499255A/en not_active Expired
- 1976-07-02 NL NL7607315.A patent/NL166024C/xx not_active IP Right Cessation
- 1976-07-03 DE DE2630053A patent/DE2630053C3/de not_active Expired
- 1976-07-05 ES ES449570A patent/ES449570A1/es not_active Expired
- 1976-07-08 AR AR263896A patent/AR211272A1/es active
- 1976-07-08 JP JP51081449A patent/JPS5210297A/ja active Granted
- 1976-07-08 PT PT65337A patent/PT65337B/pt unknown
- 1976-07-09 FR FR7621100A patent/FR2316952A1/fr active Granted
- 1976-07-09 LU LU75342A patent/LU75342A1/xx unknown
- 1976-07-09 DD DD193778A patent/DD126326A5/xx unknown
- 1976-07-09 FI FI762013A patent/FI762013A/fi not_active Application Discontinuation
- 1976-07-09 DK DK310876A patent/DK143704C/da not_active IP Right Cessation
- 1976-07-09 RO RO86909A patent/RO71662B/ro unknown

Also Published As

Publication number	Publication date
AR211272A1 (es)	1977-11-15
FR2316952B1 (es)	1979-07-20
GR60543B (en)	1978-06-14
RO71662B (ro)	1983-04-30
DK143704B (da)	1981-09-28
DD126326A5 (es)	1977-07-06
RO71662A (ro)	1983-04-29
JPS5210297A (en)	1977-01-26
IL49850A0 (en)	1976-08-31
FR2316952A1 (fr)	1977-02-04
DK310876A (da)	1977-01-11
DE2630053B2 (de)	1980-09-11
ES449570A1 (es)	1977-12-01
NL7607315A (nl)	1977-01-12
JPS5432798B2 (es)	1979-10-16
LU75342A1 (es)	1977-04-01
DK143704C (da)	1982-03-15
PT65337A (en)	1976-08-01
GB1499255A (en)	1978-01-25
AU1515776A (en)	1978-01-05
DE2630053C3 (de)	1981-05-21
FI762013A (es)	1977-01-11
DE2630053A1 (de)	1977-01-13
NL166024B (nl)	1981-01-15
IE43466L (en)	1977-01-10
PT65337B (en)	1978-01-06
NL166024C (nl)	1981-06-15
SE7606762L (sv)	1977-01-11
PH15280A (en)	1982-11-02
IE43466B1 (en)	1981-03-11

Publication	Publication Date	Title
EP0322133A1 (en)	1989-06-28	Quinazoline derivatives
US4616025A (en)	1986-10-07	Thiazolidine derivatives, process for the preparation and pharmaceutical compositions thereof
US4041163A (en)	1977-08-09	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents
IE45744B1 (en)	1982-11-17	Anti-allergenic 5-alkoxyimidazo (1,2-a)-quinoline-2-carboxylic acids and derivatives thereof
US4017625A (en)	1977-04-12	Anti-allergic N-(5-tetrazolyl)-1-oxo-1H-6-alkoxypyrimido-[1,2-a]quinoline-2-carboxamides and intermediates therefor
US4066766A (en)	1978-01-03	1-Oxo-6-substituted pyrimido [1,2-a]quinoline-2-carboxylic acids and derivatives thereof and their use as antiallergy agents
NO762170L (es)	1977-01-11
US3962445A (en)	1976-06-08	Anti-allergenic carbostyril derivatives
CA1269103A (en)	1990-05-15	Pyrido[1,2-a]pyrimidine derivatives
US4085213A (en)	1978-04-18	Tetrazolo[A]quinazol-5-ones antiallergy and antiulcer agents
US4419357A (en)	1983-12-06	3-(1H-Tetrazol-5-yl)-4(3H)-quinazolinones
US4141979A (en)	1979-02-27	Tetrazolo[a]quinazol-5-ones antiallergy and antiulcer agents
IE43028B1 (en)	1980-12-03	Substituted pyrimido-quinoline derivatives and pharmaceutical compositions containing them
US4065457A (en)	1977-12-27	4-Hydroxy-3-nitro-carbostyril compounds
US4297355A (en)	1981-10-27	(1H,3H,5H)-(1)-Benzopyrano-(2,3-d)-pyrimidine-4-one-2-thiones and their use as anti-allergy agents
US4423048A (en)	1983-12-27	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
DE3043979A1 (de)	1981-09-03	Antiallergische und geschwuerwidrige 1-oxo-1h-thiazolo-(3,2-a) pyrimidin-2-carboxamide und deren zwischenstufen
US4014881A (en)	1977-03-29	1-Oxo-1H-6-piperidinopyrimido[1,2-a]quinoline-2-carboxylic acids and esters
BE843951A (fr)	1977-01-10	Tetrazolo (a) quinazol-5-ones utiles comme agents anti-ulceres et anti-allergiques
US4414388A (en)	1983-11-08	1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
KR790001315B1 (ko)	1979-09-24	N-테트라졸릴-1-옥소-1H-6-(R₃-치환) 피리미도[1,2-a] 퀴놀린-2-카복스아미드류의 제조방법.
US3941889A (en)	1976-03-02	5-(Substituted phenoxy)-4-amino pyrimidines as anti-ulcer agents
US3886164A (en)	1975-05-27	Quinolyl oxamic acids
NZ210870A (en)	1985-09-13	Substituted 2-amino-n-(1h-tetrazol-5-yl)benzamide derivatives