JPS58194888A - 置換されたピリド〔１．２−ａ〕ピリミジンの縮合環状脂肪族誘導体 - Google Patents

置換されたピリド〔１．２−ａ〕ピリミジンの縮合環状脂肪族誘導体

Info

Publication number: JPS58194888A
Authority: JP; Japan
Prior art keywords: tetrahydro; pyrido; benzylidene; carboxylic acid; oxo
Prior art date: 1982-04-29
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.): Pending

Application number

JP58072294A

Other languages

English (en)

Japanese (ja)

Inventor

ジヤンフエデリコ・ドリア

カルロ・パツサロツテイ

ピエ−ル・パオロ・ロヴイツソロ

アダ・ブツテイノ−ニ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Carlo Erba SpA

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.)

1982-04-29

Filing date

1983-04-26

Publication date

1983-11-12

1983-04-26 Application filed by Carlo Erba SpA filed Critical Carlo Erba SpA

1983-11-12 Publication of JPS58194888A publication Critical patent/JPS58194888A/ja

Status Pending legal-status Critical Current

Links

VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical class C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 title description 2
125000004122 cyclic group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 108
UPGZAERNNNZSPM-UHFFFAOYSA-N quinazoline-8-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CC=CC2=C1 UPGZAERNNNZSPM-UHFFFAOYSA-N 0.000 claims description 62
-1 hydroxy, formyloxy Chemical group 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 9
239000000460 chlorine Chemical group 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000005973 Carvone Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
FLESJLOTERFIMR-UHFFFAOYSA-N 4-[(2,3-dimethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(N4C=C(C=CC4=N3)C(O)=O)=O)CCC2)=C1OC FLESJLOTERFIMR-UHFFFAOYSA-N 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
239000011737 fluorine Chemical group 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
FIBWTOCNGZCBQN-UHFFFAOYSA-N 2-(diethylamino)ethyl 4-benzylidene-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1CCC=2C(=O)N3C=C(C(=O)OCCN(CC)CC)C=CC3=NC=2C1=CC1=CC=CC=C1 FIBWTOCNGZCBQN-UHFFFAOYSA-N 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
LFQHFJNMSCYEPD-UHFFFAOYSA-N 4-[(3-chlorophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC(Cl)=C1 LFQHFJNMSCYEPD-UHFFFAOYSA-N 0.000 claims description 2
KXHUNPZLNBSDEW-UHFFFAOYSA-N 4-[(4-methylphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(C)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 KXHUNPZLNBSDEW-UHFFFAOYSA-N 0.000 claims description 2
235000021513 Cinchona Nutrition 0.000 claims description 2
241000157855 Cinchona Species 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
MTQPILPPIDNQQX-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethylidene)-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=C2OCOC2=CC(C=C2C=3N=C4C=CC(=CN4C(=O)C=3CCC2)C(=O)O)=C1 MTQPILPPIDNQQX-UHFFFAOYSA-N 0.000 claims 1
YPMRRQPOABVGQI-UHFFFAOYSA-N 4-[(4-ethoxyphenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C=C1C(N=C2N(C=C(C=C2)C(O)=O)C2=O)=C2CCC1 YPMRRQPOABVGQI-UHFFFAOYSA-N 0.000 claims 1
125000004980 cyclopropylene group Chemical group 0.000 claims 1
238000002844 melting Methods 0.000 description 74
230000008018 melting Effects 0.000 description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
239000002244 precipitate Substances 0.000 description 28
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
238000011282 treatment Methods 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000007935 neutral effect Effects 0.000 description 12
238000010992 reflux Methods 0.000 description 12
241000700159 Rattus Species 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000000843 powder Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000005457 ice water Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
LBMGFLVZIOZDHZ-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1C=CN=C2C=CC(C(=O)O)=CN21 LBMGFLVZIOZDHZ-UHFFFAOYSA-N 0.000 description 8
229920002472 Starch Polymers 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000008107 starch Substances 0.000 description 8
229940032147 starch Drugs 0.000 description 8
235000019698 starch Nutrition 0.000 description 8
239000003826 tablet Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
AQVWMIXYCJXOCN-UHFFFAOYSA-N 1H-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1C2=CN3C(=NC2=CC=C1)C=CC(=C3)C(=O)O AQVWMIXYCJXOCN-UHFFFAOYSA-N 0.000 description 7
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 7
238000001816 cooling Methods 0.000 description 7
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000008569 process Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
OZEAYXLITJGKGL-UHFFFAOYSA-N 11h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1C2=CC=CC=C2N=C2N1C=C(C(=O)O)C=C2 OZEAYXLITJGKGL-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
206010002198 Anaphylactic reaction Diseases 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
YFTCWIUMBCWDJW-UHFFFAOYSA-M N1=CN=CC2=CC=CC(=C12)C(=O)[O-].[Na+] Chemical compound N1=CN=CC2=CC=CC(=C12)C(=O)[O-].[Na+] YFTCWIUMBCWDJW-UHFFFAOYSA-M 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
230000036783 anaphylactic response Effects 0.000 description 4
208000003455 anaphylaxis Diseases 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000008101 lactose Substances 0.000 description 4
DORROBMBVJXJHA-UHFFFAOYSA-N methyl quinazoline-8-carboxylate Chemical compound N1=CN=C2C(C(=O)OC)=CC=CC2=C1 DORROBMBVJXJHA-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
230000002265 prevention Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
244000291564 Allium cepa Species 0.000 description 3
235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
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 3
241000700199 Cavia porcellus Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000001262 anti-secretory effect Effects 0.000 description 3
239000000427 antigen Substances 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
108091007433 antigens Proteins 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 3
TYIFOIUTIBJJDB-UHFFFAOYSA-N 2-(diethylamino)ethyl quinazoline-8-carboxylate Chemical compound CCN(CC)CCOC(=O)C1=C2N=CN=CC2=CC=C1 TYIFOIUTIBJJDB-UHFFFAOYSA-N 0.000 description 2
QHRQUMBXAYKEMS-UHFFFAOYSA-N 4-benzylidene-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylic acid Chemical compound C1CCC=2C(=O)N3C=C(C(=O)O)C=CC3=NC=2C1=CC1=CC=CC=C1 QHRQUMBXAYKEMS-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-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
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000000767 anti-ulcer Effects 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000007865 diluting Methods 0.000 description 2
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
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239000000787 lecithin Substances 0.000 description 2
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230000003137 locomotive effect Effects 0.000 description 2
239000006210 lotion Substances 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003380 propellant Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000012222 talc Nutrition 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
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238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000002555 ionophore Substances 0.000 description 1
230000000236 ionophoric effect Effects 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
230000003902 lesion Effects 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
210000003622 mature neutrocyte Anatomy 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
ZKQZJMVQJMMAFG-UHFFFAOYSA-N methanolate thorium(4+) Chemical compound [Th+4].C[O-].C[O-].C[O-].C[O-] ZKQZJMVQJMMAFG-UHFFFAOYSA-N 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
JZOYDIZTOZFWQA-UHFFFAOYSA-N methyl 4-[(4-aminophenyl)methylidene]-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1CCC=2C(=O)N3C=C(C(=O)OC)C=CC3=NC=2C1=CC1=CC=C(N)C=C1 JZOYDIZTOZFWQA-UHFFFAOYSA-N 0.000 description 1
UYKXTMISRZAQRC-UHFFFAOYSA-N methyl 4-benzylidene-11-oxo-2,3-dihydro-1h-pyrido[2,1-b]quinazoline-8-carboxylate Chemical compound C1CCC=2C(=O)N3C=C(C(=O)OC)C=CC3=NC=2C1=CC1=CC=CC=C1 UYKXTMISRZAQRC-UHFFFAOYSA-N 0.000 description 1
KSEAHCGXXNZUKX-UHFFFAOYSA-N methyl 4H-pyrido[1,2-a]pyrimidine-7-carboxylate Chemical compound COC(=O)C=1C=CC=2N(CC=CN2)C1 KSEAHCGXXNZUKX-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical compound Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
MONJTOUXCWKOFS-UHFFFAOYSA-N pyrido[2,1-b]quinazolin-11-one Chemical compound C1=CC=CN2C(=O)C3=CC=CC=C3N=C21 MONJTOUXCWKOFS-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
239000002966 varnish Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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

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

JP58072294A 1982-04-29 1983-04-26 置換されたピリド〔１．２−ａ〕ピリミジンの縮合環状脂肪族誘導体 Pending JPS58194888A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8212429		1982-04-29
GB8212429		1982-04-29
GB8309259		1983-04-06

Publications (1)

Publication Number	Publication Date
JPS58194888A true JPS58194888A (ja)	1983-11-12

Family

ID=10530061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58072294A Pending JPS58194888A (ja)	1982-04-29	1983-04-26	置換されたピリド〔１．２−ａ〕ピリミジンの縮合環状脂肪族誘導体

Country Status (4)

Country	Link
JP (1)	JPS58194888A (fr)
KR (1)	KR840004427A (fr)
BE (1)	BE896592A (fr)
ZA (1)	ZA833007B (fr)

1983
- 1983-04-26 JP JP58072294A patent/JPS58194888A/ja active Pending
- 1983-04-28 BE BE0/210647A patent/BE896592A/fr not_active IP Right Cessation
- 1983-04-28 KR KR1019830001809A patent/KR840004427A/ko not_active Ceased
- 1983-04-28 ZA ZA833007A patent/ZA833007B/xx unknown

Also Published As

Publication number	Publication date
ZA833007B (en)	1984-01-25
KR840004427A (ko)	1984-10-15
BE896592A (fr)	1983-10-28

Publication	Publication Date	Title
JPH0327380A (ja)	1991-02-05	１ｈ―イミダゾ〔４，５―ｃ〕キノリン―４―アミン類
DE2854115C2 (fr)	1988-07-28
NO134212B (fr)	1976-05-24
JPH06763B2 (ja)	1994-01-05	ベンゾ〔ｈ〕シンノリン誘導体
US3843663A (en)	1974-10-22	1,8-naphthyridine compounds
US4912104A (en)	1990-03-27	Tricyclic fused pryimidine derivatives, and their use as pharmaceuticals
US4053600A (en)	1977-10-11	Tricyclic 1,2,4-triazolo-quinazolines
US4816459A (en)	1989-03-28	Tetrazolyl-substituted pyrido[1,2-a]pyrimidines and use as SRS-A antagonists
GB2050353A (en)	1981-01-07	Substituted pyrido(1,2-a) pyrimidines
CH653036A5 (de)	1985-12-13	Substituierte thiazolo-(3,2-a)-pyrimidine.
JPS58194888A (ja)	1983-11-12	置換されたピリド〔１．２−ａ〕ピリミジンの縮合環状脂肪族誘導体
JPS6140285A (ja)	1986-02-26	環縮合ピラゾロ〔３，４−ｄ〕−ピリジン−３−オン誘導体
US3842087A (en)	1974-10-15	1,8-naphthyridine compounds
JPS588082A (ja)	1983-01-18	置換されたピロロ〔２，１−ｂ〕キナゾリンおよびピリド〔２，１−ｂ〕キナゾリンおよびそれらの製造法
EP0638570A1 (fr)	1995-02-15	Compose tricyclique dote d'un effet antiallergique
US4521419A (en)	1985-06-04	Condensed cycloaliphatic derivatives of substituted pyrido[1,2-a]pyrimidines and methods of treating allergic conditions, peptic ulcers and inhibiting gastric acid secretion with them
US3567716A (en)	1971-03-02	1,8-naphthyridine derivatives and intermediates thereof
US4547501A (en)	1985-10-15	Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents
JPH02200685A (ja)	1990-08-08	新規なインドール誘導体
JPS61227584A (ja)	1986-10-09	ポリアザ複素環誘導体
JPS63132885A (ja)	1988-06-04	キノリン−３−カルボン酸誘導体
HU190945B (en)	1986-12-28	Process for preparing substituted thiazolo/3,2-a/pyrimidine-carb oxylic acid derivatives
JPH04502475A (ja)	1992-05-07	１，２―ジヒドロ―２―オキソキノキサリンの新規誘導体、その製造および治療への該化合物の適用
JPS63295577A (ja)	1988-12-01	トリアゾロピリダジン誘導体
JPH10505330A (ja)	1998-05-26	ハロゲンイミダゾピリジン