JPH07501812A - ４−アミノ−３−アシルキノリン誘導体およびその胃酸分泌抑制剤としての使用 - Google Patents

４−アミノ−３−アシルキノリン誘導体およびその胃酸分泌抑制剤としての使用

Info

Publication number: JPH07501812A
Authority: JP; Japan
Prior art keywords: formula; ester; compound; quinolin; methylphenylamino
Prior art date: 1991-12-12
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

JP5510627A

Other languages

English (en)

Japanese (ja)

Inventor

アイフ，ロバート・ジョン

リーチ，コリン・アンドリュー

グルントラー，ゲルハルト

ポスティウス，ステファン

ライナー，ゲオルク

リーデル、リヒャルト

シェーファー，ハルトマン

ゼン−ビルフィンガー，イェルク

ジーモン，ヴォルフガング・アレクサンダー

Original Assignee

スミスクライン・ビーチャム・インタークレディット・ベスローテン・フェンノートシャップ

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.)

1991-12-12

Filing date

1992-12-10

Publication date

1995-02-23

1992-12-10 Application filed by スミスクライン・ビーチャム・インタークレディット・ベスローテン・フェンノートシャップ filed Critical スミスクライン・ビーチャム・インタークレディット・ベスローテン・フェンノートシャップ

1995-02-23 Publication of JPH07501812A publication Critical patent/JPH07501812A/ja

Status Pending legal-status Critical Current

Links

230000027119 gastric acid secretion Effects 0.000 title claims description 5
239000003112 inhibitor Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 31
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
-1 oxytrimethylene Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
239000001384 succinic acid Substances 0.000 claims description 12
239000005977 Ethylene Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000006353 oxyethylene group Chemical group 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 claims description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
NVBFKAKHBKRUJI-UHFFFAOYSA-N 4-[2-[3-butanoyl-4-(4-fluoro-2-methylanilino)quinolin-8-yl]oxyethoxy]-4-oxobutanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=C(C=C1)F)C)OCCOC(CCC(=O)O)=O NVBFKAKHBKRUJI-UHFFFAOYSA-N 0.000 claims 1
QBQHJEFTKTXTQA-UHFFFAOYSA-N 5-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-3,3-dimethyl-5-oxopentanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=CC=C1)C)OCCOC(CC(CC(=O)O)(C)C)=O QBQHJEFTKTXTQA-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000003814 drug Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229940079593 drug Drugs 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
239000000725 suspension Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
238000010992 reflux Methods 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
230000002265 prevention Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 3
UGUBQKZSNQWWEV-UHFFFAOYSA-N 4-oxo-4-phenylmethoxybutanoic acid Chemical compound OC(=O)CCC(=O)OCC1=CC=CC=C1 UGUBQKZSNQWWEV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000004587 chromatography analysis Methods 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
239000012362 glacial acetic acid Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000001078 anti-cholinergic effect Effects 0.000 description 2
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
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238000000354 decomposition reaction Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
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235000019341 magnesium sulphate Nutrition 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
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DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FBOUIAKEJMZPQG-AWNIVKPZSA-N (1E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-AWNIVKPZSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 description 1
125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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GTOFKXZQQDSVFH-UHFFFAOYSA-N 2-benzylsuccinic acid Chemical compound OC(=O)CC(C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-UHFFFAOYSA-N 0.000 description 1
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KXOKGZVCTCOQFI-UHFFFAOYSA-N 2-quinolin-2-yloxyethanol Chemical compound C1=CC=CC2=NC(OCCO)=CC=C21 KXOKGZVCTCOQFI-UHFFFAOYSA-N 0.000 description 1
PAVNZLVXYJDFNR-UHFFFAOYSA-N 3,3-dimethyloxane-2,6-dione Chemical compound CC1(C)CCC(=O)OC1=O PAVNZLVXYJDFNR-UHFFFAOYSA-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
HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 description 1
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
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LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
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150000004645 aluminates Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
230000000026 anti-ulcerogenic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000003435 antirheumatic agent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960005242 camylofin Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229950010338 fencarbamide Drugs 0.000 description 1
239000006260 foam Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
239000000499 gel Substances 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000003292 glue Substances 0.000 description 1
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
229940037467 helicobacter pylori Drugs 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000003902 lesion Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000003589 local anesthetic agent Substances 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
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
229940098779 methanesulfonic acid Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 1
229960000210 nalidixic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 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
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
125000006410 propenylene group Chemical group 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
229960000620 ranitidine Drugs 0.000 description 1
BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
208000018556 stomach disease Diseases 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229950004351 telenzepine Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
229960002372 tetracaine Drugs 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 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
238000001665 trituration Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (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)

JP5510627A 1991-12-12 1992-12-10 ４−アミノ−３−アシルキノリン誘導体およびその胃酸分泌抑制剤としての使用 Pending JPH07501812A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB9126438.2		1991-12-12
GB919126438A GB9126438D0 (en)	1991-12-12	1991-12-12	New quinoline derivatives
PCT/EP1992/002898 WO1993012090A1 (en)	1991-12-12	1992-12-10	4-amino-3-acyl quinoline derivatives and their use as inhibitors of gastric acid secretion

Publications (1)

Publication Number	Publication Date
JPH07501812A true JPH07501812A (ja)	1995-02-23

Family

ID=10706172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5510627A Pending JPH07501812A (ja)	1991-12-12	1992-12-10	４−アミノ−３−アシルキノリン誘導体およびその胃酸分泌抑制剤としての使用

Country Status (8)

Country	Link
EP (1)	EP0642500A1 (de)
JP (1)	JPH07501812A (de)
AU (1)	AU665223B2 (de)
CA (1)	CA2125681A1 (de)
GB (1)	GB9126438D0 (de)
MX (1)	MX9207162A (de)
WO (1)	WO1993012090A1 (de)
ZA (1)	ZA929568B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IS4164A (is) *	1993-06-11	1994-12-12	Ab Astra	Efnasambönd sem hindra flæði magasýru
US5556863A (en) *	1993-06-11	1996-09-17	Astra Aktiebolag	Compound for gastric acid secretion inhibition
UA80393C2 (uk)	2000-12-07	2007-09-25	Алтана Фарма Аг	Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці
MY140561A (en)	2002-02-20	2009-12-31	Nycomed Gmbh	Dosage form containing pde 4 inhibitor as active ingredient

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8621425D0 (en) *	1986-09-05	1986-10-15	Smith Kline French Lab	Compounds
GB8804444D0 (en) *	1988-02-25	1988-03-23	Smithkline Beckman Intercredit	Compounds
GB8918265D0 (en) *	1989-08-10	1989-09-20	Smithkline Beckman Intercredit	Compounds
FI933376A0 (fi) *	1991-01-29	1993-07-28	Smithkline Beecham Intercredit	4-amino-3-acylkinolinderivater och deras anvaendning som inhibitorer avmagsyrasekretion

1991
- 1991-12-12 GB GB919126438A patent/GB9126438D0/en active Pending
1992
- 1992-12-10 EP EP93900050A patent/EP0642500A1/de not_active Withdrawn
- 1992-12-10 CA CA002125681A patent/CA2125681A1/en not_active Abandoned
- 1992-12-10 MX MX9207162A patent/MX9207162A/es unknown
- 1992-12-10 AU AU31585/93A patent/AU665223B2/en not_active Ceased
- 1992-12-10 ZA ZA929568A patent/ZA929568B/xx unknown
- 1992-12-10 JP JP5510627A patent/JPH07501812A/ja active Pending
- 1992-12-10 WO PCT/EP1992/002898 patent/WO1993012090A1/en not_active Ceased

Also Published As

Publication number	Publication date
GB9126438D0 (en)	1992-02-12
MX9207162A (es)	1994-08-31
CA2125681A1 (en)	1993-06-24
ZA929568B (en)	1994-06-10
WO1993012090A1 (en)	1993-06-24
AU665223B2 (en)	1995-12-21
EP0642500A1 (de)	1995-03-15
AU3158593A (en)	1993-07-19

Publication	Publication Date	Title
DE60221233T2 (de)	2008-04-03	Neue spirotricyclische derivate und deren verwendung als phosphodiesterase-7-inhibitoren
JP3447292B2 (ja)	2003-09-16	イミダゾピリジン及び胃腸の疾病の治療のためのその使用
EP0310950B1 (de)	1993-01-13	Chinolinzwischenprodukte für die Synthese von 1H-Imidazo[4,5-c]chinolinen und 1H-Imidazo[4,5-c]chinolin-4-aminen
KR101221864B1 (ko)	2013-01-14	4-［［(7ｒ)-8-사이클로펜틸-7-에틸-5,6,7,8-테트라하이드로-5-메틸-6-옥소-2-프테리디닐］아미노］-3-메톡시-ｎ-(1-메틸-4-피페리디닐)벤즈아미드의 수화물 및 다형체, 이들의 제조방법, 및 약제로서의 이들의 용도
JP2656101B2 (ja)	1997-09-24	新規ジアゾール
DE19963234A1 (de)	2002-01-24	Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
JPH08503228A (ja)	1996-04-09	ナフタレン誘導体
CN1042633C (zh)	1999-03-24	咪唑并(1,2－a)吡啶类的氨基甲酸烷氧基烷基酯
JP2002513793A (ja)	2002-05-14	新規ｎ−オキシド
DE19541264A1 (de)	1997-05-07	Purin-6-on-derivate
EP0187251A2 (de)	1986-07-16	1,4-Dihydropyridine, Verfahren und Zwischenverbindungen zu ihrer Herstellung und ihre Anwendung als Arzneimittel
Rivalle et al.	1983	Antitumor amino-substituted pyrido [3', 4': 4, 5] pyrrolo [2, 3-g] isoquinolines and pyrido [4, 3-b] carbazole derivatives: synthesis and evaluation of compounds resulting from new side chain and heterocycle modifications
GB1581500A (en)	1980-12-17	Pyridobenzodiazepines
RU2162470C2 (ru)	2001-01-27	2,7-замещенные производные октагидропирроло[1,2-а]пиразина, способ лечения, фармацевтическая композиция, промежуточные соединения
US5252572A (en)	1993-10-12	Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same
JP2004526712A (ja)	2004-09-02	６−フェニルベンゾナフチリジン
JPH07501812A (ja)	1995-02-23	４−アミノ−３−アシルキノリン誘導体およびその胃酸分泌抑制剤としての使用
AU604726B2 (en)	1991-01-03	Antiarrhythmic agent
US5668131A (en)	1997-09-16	Substituted aminoalkylaminopyridines
EP0785191B1 (de)	2002-10-23	Kondensierte indan-derivate und ihre salze
WO1994003432A1 (en)	1994-02-17	Polyhydroxylated naphthyl 2-carboxylate, and quinolyl and isoquinolyl 3-carboxylate derivatives as protein tyrosine kinase inhibitors
JPH0386865A (ja)	1991-04-11	置換キノリン誘導体
US5331010A (en)	1994-07-19	1-phenylalkanecarboxylic acid derivatives as anticonvulsant and neuroprotective agents
EP0367944A2 (de)	1990-05-16	Ätherderivate von 4-[3H]-Chinazolinon, Verfahren zu deren Herstellung und pharmazeutische Zusammenstellungen
EP0401779A1 (de)	1990-12-12	4,5,5a,6-Tetrahydro-3H-isoxyzolo(5,4,3-k1)acridinderivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente