JPH0138784B2 - - Google Patents
Info
- Publication number
- JPH0138784B2 JPH0138784B2 JP11340180A JP11340180A JPH0138784B2 JP H0138784 B2 JPH0138784 B2 JP H0138784B2 JP 11340180 A JP11340180 A JP 11340180A JP 11340180 A JP11340180 A JP 11340180A JP H0138784 B2 JPH0138784 B2 JP H0138784B2
- Authority
- JP
- Japan
- Prior art keywords
- quinazolinesulfonamide
- compound according
- piperidino
- aminobutyl
- acid
- 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 31
- MFOTXKJGYBDQKF-UHFFFAOYSA-N n-(4-aminobutyl)-4-piperidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCCCN)=CC=C2N=CN=C1N1CCCCC1 MFOTXKJGYBDQKF-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- IYISRCJPKBYIFY-UHFFFAOYSA-N n-(4-aminobutyl)-4-(dimethylamino)quinazoline-6-sulfonamide Chemical compound C1=C(S(=O)(=O)NCCCCN)C=C2C(N(C)C)=NC=NC2=C1 IYISRCJPKBYIFY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003246 quinazolines Chemical class 0.000 claims description 4
- CENJQDNLZXPXSZ-UHFFFAOYSA-N n-(10-aminodecyl)-4-piperidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCCCCCCCCCN)=CC=C2N=CN=C1N1CCCCC1 CENJQDNLZXPXSZ-UHFFFAOYSA-N 0.000 claims description 3
- LQLSLGRAHCOMPF-UHFFFAOYSA-N n-(3-aminopropyl)-4-piperidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCCN)=CC=C2N=CN=C1N1CCCCC1 LQLSLGRAHCOMPF-UHFFFAOYSA-N 0.000 claims description 3
- BUKVQANYOJDQAM-UHFFFAOYSA-N n-(4-aminobutyl)-4-(dibutylamino)quinazoline-6-sulfonamide Chemical compound C1=C(S(=O)(=O)NCCCCN)C=C2C(N(CCCC)CCCC)=NC=NC2=C1 BUKVQANYOJDQAM-UHFFFAOYSA-N 0.000 claims description 3
- ZRHNSGKXNDTMBA-UHFFFAOYSA-N n-(4-aminobutyl)-4-(diethylamino)quinazoline-6-sulfonamide Chemical compound C1=C(S(=O)(=O)NCCCCN)C=C2C(N(CC)CC)=NC=NC2=C1 ZRHNSGKXNDTMBA-UHFFFAOYSA-N 0.000 claims description 3
- AHJBHKTZBNAQDR-UHFFFAOYSA-N quinazoline-6-sulfonamide Chemical compound N1=CN=CC2=CC(S(=O)(=O)N)=CC=C21 AHJBHKTZBNAQDR-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XTPYKKYPZAFVPV-UHFFFAOYSA-N n-(4-aminobutyl)-4-pyrrolidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCCCN)=CC=C2N=CN=C1N1CCCC1 XTPYKKYPZAFVPV-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- -1 dimethylamino, diethylamino, di-n-propylamino Chemical group 0.000 description 21
- 230000000694 effects Effects 0.000 description 11
- 230000017531 blood circulation Effects 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 210000001105 femoral artery Anatomy 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PEQYDITZCGOZNV-UHFFFAOYSA-N 4-piperidin-1-ylquinazoline-6-sulfonyl chloride Chemical compound C12=CC(S(=O)(=O)Cl)=CC=C2N=CN=C1N1CCCCC1 PEQYDITZCGOZNV-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000005700 Putrescine Substances 0.000 description 5
- 230000008602 contraction Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 210000002385 vertebral artery Anatomy 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 229940079919 digestives enzyme preparation Drugs 0.000 description 4
- 230000002040 relaxant effect Effects 0.000 description 4
- 210000002460 smooth muscle Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 210000001363 mesenteric artery superior Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SAGBMEONGUEIJF-UHFFFAOYSA-N n-(2-aminoethyl)-4-piperidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCN)=CC=C2N=CN=C1N1CCCCC1 SAGBMEONGUEIJF-UHFFFAOYSA-N 0.000 description 3
- 229960002275 pentobarbital sodium Drugs 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000283977 Oryctolagus Species 0.000 description 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000003218 coronary vasodilator agent Substances 0.000 description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- CFTBZXNFXHGMOR-UHFFFAOYSA-N n-(6-aminohexyl)-4-piperidin-1-ylquinazoline-6-sulfonamide Chemical compound C12=CC(S(=O)(=O)NCCCCCCN)=CC=C2N=CN=C1N1CCCCC1 CFTBZXNFXHGMOR-UHFFFAOYSA-N 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 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
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VIMMTIWARBDYNN-UHFFFAOYSA-N 4-piperidin-1-ylquinazoline Chemical compound C1CCCCN1C1=NC=NC2=CC=CC=C12 VIMMTIWARBDYNN-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris 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
- 102000005701 Calcium-Binding Proteins Human genes 0.000 description 1
- 108010045403 Calcium-Binding Proteins Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 230000009460 calcium influx Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 239000007788 liquid Substances 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
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- BKNGFMYHEGMARQ-UHFFFAOYSA-N n-(4-aminobutyl)-4-(dihexylamino)quinazoline-6-sulfonamide Chemical compound C1=C(S(=O)(=O)NCCCCN)C=C2C(N(CCCCCC)CCCCCC)=NC=NC2=C1 BKNGFMYHEGMARQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960001476 pentoxifylline Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11340180A JPS5738775A (en) | 1980-08-20 | 1980-08-20 | Quinazoline derivative |
| US06/293,192 US4510307A (en) | 1980-08-20 | 1981-08-17 | 6-Quinazolinesulfonyl derivatives and process for preparation thereof |
| DE8181106461T DE3166969D1 (en) | 1980-08-20 | 1981-08-19 | 6-quinazolinesulfonyl derivatives and process for preparation thereof |
| EP81106461A EP0046572B1 (en) | 1980-08-20 | 1981-08-19 | 6-quinazolinesulfonyl derivatives and process for preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11340180A JPS5738775A (en) | 1980-08-20 | 1980-08-20 | Quinazoline derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5738775A JPS5738775A (en) | 1982-03-03 |
| JPH0138784B2 true JPH0138784B2 (cs) | 1989-08-16 |
Family
ID=14611355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11340180A Granted JPS5738775A (en) | 1980-08-20 | 1980-08-20 | Quinazoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5738775A (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6036556U (ja) * | 1983-08-22 | 1985-03-13 | スズキ株式会社 | 気化器のチョ−ク装置 |
| JPH0557342U (ja) * | 1991-12-26 | 1993-07-30 | テイケイ気化器株式会社 | 気化器の自動始動装置 |
-
1980
- 1980-08-20 JP JP11340180A patent/JPS5738775A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5738775A (en) | 1982-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3335362B2 (ja) | キノレイン−２（１ｈ）−オン誘導体セロトニンアンタゴニスト | |
| US4209623A (en) | Pyrimidine-5-N-(1H-tetrazol-5-yl)-carboxamides | |
| JP4316794B2 (ja) | イソキノリン誘導体及び医薬 | |
| RU2114620C1 (ru) | Ингибитор атеросклеротического утолщения внутренней оболочки сосудов | |
| CN1794987B (zh) | 具有提高的抗炎、抗血栓形成和抗血小板活性的作为降胆固醇药的氟伐他汀、普伐他汀、西立伐他汀、阿托伐他汀和罗苏伐他汀的硝基氧基衍生物 | |
| JP6615207B2 (ja) | 複素環式化合物及びその使用 | |
| CN104053439A (zh) | 1-(5,6-二氯-1h-苯并[d]咪唑-2-基)-1h-吡唑-4-羧酸的葡甲胺盐制剂 | |
| JPH10182583A (ja) | 新規ヒドロキサム酸誘導体 | |
| ES2224134T3 (es) | Compuestos de pirazolo(3,4-g)quinoxalina que inhiben la proteina tirosina-quinasa del receptor de pdgf. | |
| JP2021512075A (ja) | 一過性受容体電位ａ１イオンチャネルの阻害 | |
| KR0137766B1 (ko) | 피롤로[3,2-e] 피라졸로[1,5-a] 피리미딘 유도체 및 이를 함유하는 약제 | |
| US6077841A (en) | 5-heterocyclyl pyrazolo[4,3-d]pyrimidin-7-ones for the treatment of male erectile dysfunction | |
| JPS61227581A (ja) | 血管拡張剤 | |
| JP2004521964A5 (cs) | ||
| EP0373663B1 (en) | Castanospermine esters in the inhibition of tumor metastasis | |
| US20080139607A1 (en) | New Compounds | |
| JPS58194859A (ja) | １−カルボキシアルカノイルインドリン−２−カルボン酸エステル及びその製造方法、並びに該エステルを含有する医薬 | |
| JPH07133224A (ja) | 動脈硬化治療薬 | |
| CZ403592A3 (en) | Arylcarbonylaminoalkyldihydrooxopyridines, process of their preparation and their use | |
| JPH0138784B2 (cs) | ||
| JPH062741B2 (ja) | ２級のイソキノリンスルホンアミド誘導体 | |
| US5753667A (en) | 1-oxo-2- (phenylsulphonylamino) pentylpiperidine derivatives, their preparation and their therapeutic application | |
| JP2980749B2 (ja) | フラン誘導体 | |
| Ferrarini et al. | Synthesis of 1, 8-naphthyridine derivatives: Potential antihypertensive agents–Part VIII | |
| JPH0959245A (ja) | Ｎ−（２−プロペノイル）グアニジン誘導体 |