JPS6139947B2 - - Google Patents
Info
- Publication number
- JPS6139947B2 JPS6139947B2 JP52014335A JP1433577A JPS6139947B2 JP S6139947 B2 JPS6139947 B2 JP S6139947B2 JP 52014335 A JP52014335 A JP 52014335A JP 1433577 A JP1433577 A JP 1433577A JP S6139947 B2 JPS6139947 B2 JP S6139947B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- dihydro
- oxo
- melting point
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 133
- -1 cyclopropylalkyloxy Chemical group 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 89
- 238000004519 manufacturing process Methods 0.000 claims description 58
- 238000010992 reflux Methods 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 235000019270 ammonium chloride Nutrition 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005336 allyloxy group Chemical group 0.000 claims description 9
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 150000002169 ethanolamines Chemical class 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 159
- 238000002844 melting Methods 0.000 description 130
- 230000008018 melting Effects 0.000 description 130
- 239000000203 mixture Substances 0.000 description 119
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 71
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 37
- 238000003756 stirring Methods 0.000 description 36
- 239000007787 solid Substances 0.000 description 33
- 239000005457 ice water Substances 0.000 description 32
- 239000007788 liquid Substances 0.000 description 31
- 229960000583 acetic acid Drugs 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 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 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000000427 antigen Substances 0.000 description 12
- 102000036639 antigens Human genes 0.000 description 12
- 108091007433 antigens Proteins 0.000 description 12
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
- 238000010790 dilution Methods 0.000 description 11
- 239000012895 dilution Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 210000002966 serum Anatomy 0.000 description 11
- 150000003937 benzamidines Chemical class 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 9
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 description 8
- 238000007429 general method Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 208000006673 asthma Diseases 0.000 description 6
- NHBDYNVEEOSTIH-UHFFFAOYSA-N chembl14922 Chemical compound CCCOC1=CC=CC=C1C(NC1=O)=NC=C1C1=NN=NN1 NHBDYNVEEOSTIH-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- AHRQYOSAXZQCIG-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=C=NC=N[CH]1 AHRQYOSAXZQCIG-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NGMHLSBQVIXGNZ-UHFFFAOYSA-N (2-ethoxybenzenecarboximidoyl)azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1C(N)=N NGMHLSBQVIXGNZ-UHFFFAOYSA-N 0.000 description 5
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 5
- ARRHAFFWXFQZSR-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound CCOC1=CC=CC=C1C1=NC=C(C#N)C(=O)N1 ARRHAFFWXFQZSR-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 108010058846 Ovalbumin Proteins 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- NTOYIGNATVNWOU-UHFFFAOYSA-N ethyl 2-(2-ethoxyphenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1OCC NTOYIGNATVNWOU-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- HNTRYPFDBNXKOS-UHFFFAOYSA-N 2-(2-methylpropoxy)benzenecarboximidamide Chemical compound CC(C)COC1=CC=CC=C1C(N)=N HNTRYPFDBNXKOS-UHFFFAOYSA-N 0.000 description 4
- NWELOPILLFFSFZ-UHFFFAOYSA-N 2-(cyclopropylmethoxy)benzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC=C1OCC1CC1 NWELOPILLFFSFZ-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- OIEYSUXLJYFFPI-UHFFFAOYSA-N 2-ethoxybenzenecarboximidamide;sulfurofluoridic acid Chemical compound OS(F)(=O)=O.CCOC1=CC=CC=C1C(N)=N OIEYSUXLJYFFPI-UHFFFAOYSA-N 0.000 description 4
- KNOPIPOLVBCPEN-UHFFFAOYSA-N 2-ethylsulfanylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CCSC1=CC=CC=C1C(N)=N KNOPIPOLVBCPEN-UHFFFAOYSA-N 0.000 description 4
- JQCXHLMDSPVRLE-UHFFFAOYSA-N 5-methoxy-2-propoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CCCOC1=CC=C(OC)C=C1C(N)=N JQCXHLMDSPVRLE-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 241000700647 Variola virus Species 0.000 description 4
- XZHKVYYQQVEUBZ-UHFFFAOYSA-N [amino-(2-propoxyphenyl)methylidene]azanium;chloride Chemical compound Cl.CCCOC1=CC=CC=C1C(N)=N XZHKVYYQQVEUBZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000538 analytical sample Substances 0.000 description 4
- 239000001045 blue dye Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 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 4
- IVBFHLYXRBKTMG-UHFFFAOYSA-N ethyl 6-oxo-2-(2-propoxyphenyl)-1h-pyrimidine-5-carboxylate Chemical compound CCCOC1=CC=CC=C1C1=NC=C(C(=O)OCC)C(=O)N1 IVBFHLYXRBKTMG-UHFFFAOYSA-N 0.000 description 4
- 230000003053 immunization Effects 0.000 description 4
- 238000002649 immunization Methods 0.000 description 4
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- YNJQOVDUKUWUQT-UHFFFAOYSA-N 2-butoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CCCCOC1=CC=CC=C1C(N)=N YNJQOVDUKUWUQT-UHFFFAOYSA-N 0.000 description 3
- JNYOMPUIZRNERF-UHFFFAOYSA-N 2-ethoxy-5-methoxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CCOC1=CC=C(OC)C=C1C(N)=N JNYOMPUIZRNERF-UHFFFAOYSA-N 0.000 description 3
- GOSDGLKRVHPJEV-UHFFFAOYSA-N 2-ethoxybenzenecarboximidamide Chemical compound CCOC1=CC=CC=C1C(N)=N GOSDGLKRVHPJEV-UHFFFAOYSA-N 0.000 description 3
- IOJAQFYHZXUYDH-UHFFFAOYSA-N 2-propan-2-yloxybenzenecarboximidamide;hydrochloride Chemical compound Cl.CC(C)OC1=CC=CC=C1C(N)=N IOJAQFYHZXUYDH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- KHLKWMAHIJEMOS-UHFFFAOYSA-N ethyl 2-[2-(2-methylpropoxy)phenyl]-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1OCC(C)C KHLKWMAHIJEMOS-UHFFFAOYSA-N 0.000 description 3
- JSIHCFJCICVJHJ-UHFFFAOYSA-N ethyl 6-oxo-2-phenyl-1h-pyrimidine-5-carboxylate Chemical class N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1 JSIHCFJCICVJHJ-UHFFFAOYSA-N 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- 229960001340 histamine Drugs 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical class [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- VQGDVXIMWWGBNY-UHFFFAOYSA-N methyl 2-carbamimidoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(N)=N VQGDVXIMWWGBNY-UHFFFAOYSA-N 0.000 description 1
- NZCNQOPLKTYKQB-UHFFFAOYSA-N methyl 2-ethoxy-5-methoxybenzenecarboximidate;sulfurofluoridic acid Chemical compound OS(F)(=O)=O.CCOC1=CC=C(OC)C=C1C(=N)OC NZCNQOPLKTYKQB-UHFFFAOYSA-N 0.000 description 1
- YXOZOCRLGICTPN-UHFFFAOYSA-N methyl 2-ethoxybenzenecarboximidate;methyl hydrogen sulfate Chemical compound COS(O)(=O)=O.CCOC1=CC=CC=C1C(=N)OC YXOZOCRLGICTPN-UHFFFAOYSA-N 0.000 description 1
- KBVGDNOKQIRHSD-UHFFFAOYSA-N methyl 3-carbamimidoyl-4-ethoxybenzoate Chemical compound C(=O)(OC)C=1C=CC(=C(C(=N)N)C1)OCC.C(=O)(OC)C=1C=CC(=C(C(=N)N)C1)OCC KBVGDNOKQIRHSD-UHFFFAOYSA-N 0.000 description 1
- WYTKHSAZZPUCPK-UHFFFAOYSA-N methyl 3-carbamimidoyl-4-ethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1C(N)=N WYTKHSAZZPUCPK-UHFFFAOYSA-N 0.000 description 1
- OHSWRVNWUHUSSN-UHFFFAOYSA-N methyl 3-carbamoyl-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(C(N)=O)=C1 OHSWRVNWUHUSSN-UHFFFAOYSA-N 0.000 description 1
- BLHOGOSXQVNCCS-UHFFFAOYSA-N methyl 5-methoxy-2-propoxybenzenecarboximidate;sulfurofluoridic acid Chemical compound OS(F)(=O)=O.CCCOC1=CC=C(OC)C=C1C(=N)OC BLHOGOSXQVNCCS-UHFFFAOYSA-N 0.000 description 1
- FGFLVXMKWVVLRQ-UHFFFAOYSA-N methyl hydrogen sulfate;methyl 2-propoxybenzenecarboximidate Chemical compound COS(O)(=O)=O.CCCOC1=CC=CC=C1C(=N)OC FGFLVXMKWVVLRQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 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
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229960001005 tuberculin Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65778776A | 1976-02-13 | 1976-02-13 | |
| US05/748,851 US4082751A (en) | 1976-02-13 | 1976-12-08 | Therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52118481A JPS52118481A (en) | 1977-10-04 |
| JPS6139947B2 true JPS6139947B2 (fr) | 1986-09-06 |
Family
ID=27097492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1433577A Granted JPS52118481A (en) | 1976-02-13 | 1977-02-14 | Therapeutic agents |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS52118481A (fr) |
| AU (1) | AU508970B2 (fr) |
| CA (1) | CA1083152A (fr) |
| CH (1) | CH635339A5 (fr) |
| DE (1) | DE2705609A1 (fr) |
| DK (1) | DK149044C (fr) |
| FI (1) | FI62533C (fr) |
| FR (1) | FR2340943A1 (fr) |
| GB (1) | GB1541351A (fr) |
| IE (1) | IE44603B1 (fr) |
| LU (1) | LU76722A1 (fr) |
| NL (1) | NL173055C (fr) |
| SE (1) | SE433494B (fr) |
| YU (1) | YU41567B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419357A (en) * | 1982-01-18 | 1983-12-06 | The Dow Chemical Company | 3-(1H-Tetrazol-5-yl)-4(3H)-quinazolinones |
| CN101747282A (zh) * | 2008-12-10 | 2010-06-23 | 上海特化医药科技有限公司 | 一类含有嘧啶酮苯基的化合物、其药物组合物及其制备方法和用途 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883653A (en) * | 1972-10-24 | 1975-05-13 | Pfizer | Method of preventing asthmatic symptoms |
-
1977
- 1977-02-03 AU AU21895/77A patent/AU508970B2/en not_active Expired
- 1977-02-08 LU LU76722A patent/LU76722A1/xx unknown
- 1977-02-09 FR FR7703650A patent/FR2340943A1/fr active Granted
- 1977-02-09 FI FI770427A patent/FI62533C/fi not_active IP Right Cessation
- 1977-02-09 CA CA271,406A patent/CA1083152A/fr not_active Expired
- 1977-02-09 GB GB5437/77A patent/GB1541351A/en not_active Expired
- 1977-02-10 DE DE19772705609 patent/DE2705609A1/de active Granted
- 1977-02-10 DK DK57377A patent/DK149044C/da not_active IP Right Cessation
- 1977-02-11 SE SE7701552A patent/SE433494B/xx not_active IP Right Cessation
- 1977-02-11 CH CH173477A patent/CH635339A5/de not_active IP Right Cessation
- 1977-02-11 YU YU354/77A patent/YU41567B/xx unknown
- 1977-02-11 NL NLAANVRAGE7701483,A patent/NL173055C/xx not_active IP Right Cessation
- 1977-02-11 IE IE297/77A patent/IE44603B1/en unknown
- 1977-02-14 JP JP1433577A patent/JPS52118481A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52118481A (en) | 1977-10-04 |
| FI62533C (fi) | 1983-01-10 |
| FR2340943A1 (fr) | 1977-09-09 |
| NL173055C (nl) | 1983-12-01 |
| DE2705609A1 (de) | 1977-08-25 |
| FI62533B (fi) | 1982-09-30 |
| AU508970B2 (en) | 1980-04-17 |
| IE44603B1 (en) | 1982-01-27 |
| FI770427A (fr) | 1977-08-14 |
| YU35477A (en) | 1982-10-31 |
| AU2189577A (en) | 1978-08-10 |
| YU41567B (en) | 1987-10-31 |
| DE2705609C2 (fr) | 1988-12-15 |
| LU76722A1 (fr) | 1977-08-18 |
| DK57377A (da) | 1977-08-14 |
| FR2340943B1 (fr) | 1981-01-09 |
| NL7701483A (nl) | 1977-08-16 |
| DK149044B (da) | 1985-12-30 |
| CA1083152A (fr) | 1980-08-05 |
| IE44603L (en) | 1977-08-13 |
| NL173055B (nl) | 1983-07-01 |
| SE7701552L (sv) | 1977-09-23 |
| SE433494B (sv) | 1984-05-28 |
| GB1541351A (en) | 1979-02-28 |
| DK149044C (da) | 1986-06-02 |
| CH635339A5 (en) | 1983-03-31 |
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