DE3011490A1 - 4-amino-3-chinolincarbonsaeure und derivate davon, verfahren zur herstellung dieser verbindungen und ihreverwendung - Google Patents
4-amino-3-chinolincarbonsaeure und derivate davon, verfahren zur herstellung dieser verbindungen und ihreverwendungInfo
- Publication number
- DE3011490A1 DE3011490A1 DE19803011490 DE3011490A DE3011490A1 DE 3011490 A1 DE3011490 A1 DE 3011490A1 DE 19803011490 DE19803011490 DE 19803011490 DE 3011490 A DE3011490 A DE 3011490A DE 3011490 A1 DE3011490 A1 DE 3011490A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- amino
- compound
- quinolinecarboxylate
- methoxy
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims description 85
- 238000004519 manufacturing process Methods 0.000 title description 47
- 238000000034 method Methods 0.000 title description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 69
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
- 238000002360 preparation method Methods 0.000 claims description 59
- -1 cyano, hydroxy, carbamoyl Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 11
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 11
- 230000028327 secretion Effects 0.000 claims description 9
- 230000002496 gastric effect Effects 0.000 claims description 8
- 201000005917 gastric ulcer Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- ULHHZGBLUSMTHM-UHFFFAOYSA-N ethyl 8-(dimethylamino)-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(N(C)C)=CC=CC2=C1NC1=CC=CC=C1C ULHHZGBLUSMTHM-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- MCODIFYTJFMYQG-UHFFFAOYSA-N 8-methoxyquinoline-3-carboxylic acid Chemical compound OC(=O)C1=CN=C2C(OC)=CC=CC2=C1 MCODIFYTJFMYQG-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- LPVOFRWOKFQKMW-UHFFFAOYSA-N ethyl 4-(2-methoxyanilino)-8-methylquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C)=CC=CC2=C1NC1=CC=CC=C1OC LPVOFRWOKFQKMW-UHFFFAOYSA-N 0.000 claims 1
- LTPVJDPFDLGLRT-UHFFFAOYSA-N ethyl 8-ethoxy-4-(2-methoxyanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OCC)=CC=CC2=C1NC1=CC=CC=C1OC LTPVJDPFDLGLRT-UHFFFAOYSA-N 0.000 claims 1
- KRIDZTDGIKDFGO-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methoxyanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1OC KRIDZTDGIKDFGO-UHFFFAOYSA-N 0.000 claims 1
- 230000027119 gastric acid secretion Effects 0.000 claims 1
- 101150032584 oxy-4 gene Proteins 0.000 claims 1
- ZJZQDAVJNWMOTI-UHFFFAOYSA-N propan-2-yl 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CC(C)OC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C ZJZQDAVJNWMOTI-UHFFFAOYSA-N 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 32
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 29
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 26
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UEFKMJWKPVAVND-UHFFFAOYSA-N 4-aminoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=NC2=C1 UEFKMJWKPVAVND-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WBRPQQSADOCKCH-UHFFFAOYSA-N 2-methylsulfanylaniline Chemical compound CSC1=CC=CC=C1N WBRPQQSADOCKCH-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 210000004211 gastric acid Anatomy 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010012944 Tetragastrin Proteins 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000010407 ammonium alginate Nutrition 0.000 description 3
- 239000000728 ammonium alginate Substances 0.000 description 3
- KPGABFJTMYCRHJ-YZOKENDUSA-N ammonium alginate Chemical compound [NH4+].[NH4+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O KPGABFJTMYCRHJ-YZOKENDUSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 235000010410 calcium alginate Nutrition 0.000 description 3
- 239000000648 calcium alginate Substances 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical class C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 3
- CRJUJZNGVQRIJL-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C CRJUJZNGVQRIJL-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 3
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- IETBAKGCCBATLU-UHFFFAOYSA-N 4-anilinoquinoline-3-carboxylic acid Chemical class OC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1 IETBAKGCCBATLU-UHFFFAOYSA-N 0.000 description 2
- HJSCQRDGGJZGJH-UHFFFAOYSA-N 4-chloroquinoline-3-carboxylic acid Chemical class C1=CC=CC2=C(Cl)C(C(=O)O)=CN=C21 HJSCQRDGGJZGJH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000001262 anti-secretory effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- 230000003247 decreasing effect Effects 0.000 description 2
- YBEOYBKKSWUSBR-UHFFFAOYSA-N ethyl 4-oxo-1h-quinoline-3-carboxylate Chemical class C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 YBEOYBKKSWUSBR-UHFFFAOYSA-N 0.000 description 2
- ZLEIPGHLPPITMX-UHFFFAOYSA-N ethyl 8-methoxy-4-(2-nitroanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1[N+]([O-])=O ZLEIPGHLPPITMX-UHFFFAOYSA-N 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- AKNCZQFOJXLRDU-UHFFFAOYSA-N 2-[(3-ethoxycarbonyl-8-phenylquinolin-4-yl)amino]benzoic acid Chemical compound CCOC(=O)C1=CN=C2C(C=3C=CC=CC=3)=CC=CC2=C1NC1=CC=CC=C1C(O)=O AKNCZQFOJXLRDU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- SBRYFUVVWOMLLP-UHFFFAOYSA-N 2-azaniumyl-4-methoxy-4-oxobutanoate Chemical compound COC(=O)CC(N)C(O)=O SBRYFUVVWOMLLP-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- RQRMTSCQUFXYNI-UHFFFAOYSA-N 2-ethyl-4-methoxyaniline Chemical compound CCC1=CC(OC)=CC=C1N RQRMTSCQUFXYNI-UHFFFAOYSA-N 0.000 description 1
- OXFMPJRLJLBBRQ-UHFFFAOYSA-N 2-ethylsulfanylaniline Chemical compound CCSC1=CC=CC=C1N OXFMPJRLJLBBRQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DASZTFGYDXJWBT-UHFFFAOYSA-N quinoline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(C(=O)O)=CC=C21 DASZTFGYDXJWBT-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2398179A | 1979-03-26 | 1979-03-26 | |
| US06/127,153 US4343804A (en) | 1979-03-26 | 1980-03-04 | 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3011490A1 true DE3011490A1 (de) | 1981-03-12 |
| DE3011490C2 DE3011490C2 (enExample) | 1988-12-22 |
Family
ID=26697875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803011490 Granted DE3011490A1 (de) | 1979-03-26 | 1980-03-25 | 4-amino-3-chinolincarbonsaeure und derivate davon, verfahren zur herstellung dieser verbindungen und ihreverwendung |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4343804A (enExample) |
| JP (1) | JPH02117663A (enExample) |
| AR (1) | AR230268A1 (enExample) |
| AT (1) | AT372373B (enExample) |
| AU (1) | AU528388B2 (enExample) |
| BR (1) | BR8001779A (enExample) |
| CA (1) | CA1147338A (enExample) |
| CH (1) | CH644105A5 (enExample) |
| DE (1) | DE3011490A1 (enExample) |
| DK (1) | DK156056C (enExample) |
| EG (1) | EG15009A (enExample) |
| ES (1) | ES8103048A1 (enExample) |
| FI (1) | FI77452C (enExample) |
| FR (1) | FR2452485B1 (enExample) |
| GB (1) | GB2047244B (enExample) |
| GR (1) | GR68006B (enExample) |
| HK (1) | HK67983A (enExample) |
| IE (1) | IE49577B1 (enExample) |
| IL (1) | IL59628A (enExample) |
| IN (1) | IN151446B (enExample) |
| IT (1) | IT1133079B (enExample) |
| MX (1) | MX6264E (enExample) |
| NL (1) | NL8001752A (enExample) |
| NO (1) | NO153927C (enExample) |
| NZ (1) | NZ193252A (enExample) |
| PH (1) | PH16416A (enExample) |
| PL (1) | PL125030B1 (enExample) |
| PT (1) | PT71008B (enExample) |
| SE (1) | SE435837B (enExample) |
| SG (1) | SG33683G (enExample) |
| YU (1) | YU41702B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7175854B2 (en) | 2000-12-07 | 2007-02-13 | Altana Pharma Ag | Pharmaceutical preparation comprising an active dispersed on a matrix |
| US7951397B2 (en) | 2002-02-20 | 2011-05-31 | Nycomed Gmbh | Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8610981D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Quinoline amides |
| GB8621425D0 (en) * | 1986-09-05 | 1986-10-15 | Smith Kline French Lab | Compounds |
| GB8804445D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804443D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804446D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804448D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804447D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804444D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| US5432182A (en) * | 1989-02-23 | 1995-07-11 | Smithkline Beecham Intercredit B.V. | Compounds substituted quinoline derivatives |
| CA2011086A1 (en) * | 1989-03-17 | 1990-09-17 | Karl-Heinz Geiss | 2-alkyl-4-arylmethylaminoquinolines, the use thereof and drugs prepared therefrom |
| DE3917233A1 (de) * | 1989-05-26 | 1990-11-29 | Basf Ag | 8-substituierte 4-(heterocyclylmethylamino)-chinoline, ihre verwendung und daraus hergestellte arzneimittel |
| GB8918265D0 (en) * | 1989-08-10 | 1989-09-20 | Smithkline Beckman Intercredit | Compounds |
| US5362743A (en) * | 1993-03-09 | 1994-11-08 | Pfizer Inc. | Aminoquinoline derivatives |
| 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 |
| AU682051B2 (en) * | 1993-08-10 | 1997-09-18 | James Black Foundation Limited | Gastrin and CCK receptor ligands |
| US5650415A (en) * | 1995-06-07 | 1997-07-22 | Sugen, Inc. | Quinoline compounds |
| KR0169813B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 4-아미노-3-아실나프티리딘 유도체 |
| US5760041A (en) * | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| US6875769B2 (en) * | 1996-05-23 | 2005-04-05 | Pfizer Inc. | Substituted6,6-hetero-bicyclicderivatives |
| US5929080A (en) * | 1997-05-06 | 1999-07-27 | American Cyanamid Company | Method of treating polycystic kidney disease |
| US6251912B1 (en) | 1997-08-01 | 2001-06-26 | American Cyanamid Company | Substituted quinazoline derivatives |
| US6323209B1 (en) | 1997-11-06 | 2001-11-27 | American Cyanamid Company | Method of treating or inhibiting colonic polyps |
| DK2253620T3 (da) | 1998-09-29 | 2014-03-31 | Wyeth Holdings Llc | Substituerede 3-cyanoquinoliner som protein-tyrosinkinase-inhibitorer |
| CA2395772C (en) * | 1999-12-28 | 2010-09-28 | Eisai Co., Ltd. | Sulfonamide-containing heterocyclic compounds |
| US6521618B2 (en) | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| US6576644B2 (en) * | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| PT1599468E (pt) | 2003-01-14 | 2008-01-14 | Arena Pharm Inc | Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia |
| MXPA04008070A (es) | 2003-03-10 | 2004-11-26 | Altana Pharma Ag | Novedoso proceso para la preparacion de roflumilasto. |
| EP2287165A3 (en) * | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| US8663694B2 (en) * | 2005-03-16 | 2014-03-04 | Takeda Gmbh | Taste masked dosage form containing roflumilast |
| WO2011022216A1 (en) * | 2009-08-17 | 2011-02-24 | High Point Pharmaceuticals, Llc | Substituted pyridine derivatives, pharmaceutical compositions, and methods of use to treat oxidative stress |
| JP5856980B2 (ja) | 2010-01-27 | 2016-02-10 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｇｐｒ１１９レセプターのモジュレーターおよびそれに関連する障害の処置 |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| DK3310760T3 (da) | 2015-06-22 | 2022-10-24 | Arena Pharm Inc | Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser |
| EP3538512B1 (en) * | 2016-11-11 | 2021-06-16 | Bayer Animal Health GmbH | New anthelmintic quinoline-3-carboxamide derivatives |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| WO2019084271A1 (en) * | 2017-10-25 | 2019-05-02 | Children's Medical Center Corporation | PAPD5 INHIBITORS AND METHODS OF USE |
| AU2019266511B2 (en) | 2018-05-09 | 2022-12-08 | Elanco Animal Health Gmbh | New quinoline derivatives |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| CN113993848A (zh) | 2019-04-24 | 2022-01-28 | 儿童医学中心公司 | Papd5抑制剂及其使用方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3470186A (en) * | 1967-06-02 | 1969-09-30 | American Cyanamid Co | Substituted 4-anilino-3-quinolinecarboxylic acids and esters |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4838712A (enExample) * | 1971-09-18 | 1973-06-07 |
-
1980
- 1980-03-04 US US06/127,153 patent/US4343804A/en not_active Expired - Lifetime
- 1980-03-14 IL IL59628A patent/IL59628A/xx unknown
- 1980-03-22 GR GR61513A patent/GR68006B/el unknown
- 1980-03-24 FR FR8006516A patent/FR2452485B1/fr not_active Expired
- 1980-03-24 FI FI800910A patent/FI77452C/fi not_active IP Right Cessation
- 1980-03-24 IE IE605/80A patent/IE49577B1/en unknown
- 1980-03-24 MX MX808722U patent/MX6264E/es unknown
- 1980-03-24 AT AT0156480A patent/AT372373B/de not_active IP Right Cessation
- 1980-03-25 PL PL1980222993A patent/PL125030B1/pl unknown
- 1980-03-25 DK DK128380A patent/DK156056C/da not_active IP Right Cessation
- 1980-03-25 NO NO800858A patent/NO153927C/no unknown
- 1980-03-25 IN IN345/CAL/80A patent/IN151446B/en unknown
- 1980-03-25 CH CH234080A patent/CH644105A5/fr not_active IP Right Cessation
- 1980-03-25 NL NL8001752A patent/NL8001752A/nl not_active Application Discontinuation
- 1980-03-25 GB GB8009991A patent/GB2047244B/en not_active Expired
- 1980-03-25 SE SE8002292A patent/SE435837B/sv not_active IP Right Cessation
- 1980-03-25 PH PH23804A patent/PH16416A/en unknown
- 1980-03-25 NZ NZ193252A patent/NZ193252A/en unknown
- 1980-03-25 ES ES489887A patent/ES8103048A1/es not_active Expired
- 1980-03-25 BR BR8001779A patent/BR8001779A/pt unknown
- 1980-03-25 PT PT71008A patent/PT71008B/pt unknown
- 1980-03-25 EG EG80174A patent/EG15009A/xx active
- 1980-03-25 DE DE19803011490 patent/DE3011490A1/de active Granted
- 1980-03-26 IT IT67465/80A patent/IT1133079B/it active
- 1980-03-26 AU AU56848/80A patent/AU528388B2/en not_active Ceased
- 1980-03-26 CA CA000348417A patent/CA1147338A/en not_active Expired
- 1980-03-26 YU YU844/80A patent/YU41702B/xx unknown
- 1980-03-26 AR AR280455A patent/AR230268A1/es active
-
1983
- 1983-06-13 SG SG336/83A patent/SG33683G/en unknown
- 1983-12-15 HK HK679/83A patent/HK67983A/xx unknown
-
1989
- 1989-09-26 JP JP1250369A patent/JPH02117663A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3470186A (en) * | 1967-06-02 | 1969-09-30 | American Cyanamid Co | Substituted 4-anilino-3-quinolinecarboxylic acids and esters |
Non-Patent Citations (4)
| Title |
|---|
| J. Chem. Soc., 1951, S.1389-1392 * |
| J. Indian Chem. Soc. 34, 906-908, 1957 * |
| J. Med. Chem., 1969, 12 (6), S.1096-1097 * |
| J. Med. Pharm. Chem. 5, 546-558, 1962 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7175854B2 (en) | 2000-12-07 | 2007-02-13 | Altana Pharma Ag | Pharmaceutical preparation comprising an active dispersed on a matrix |
| US7951398B2 (en) | 2000-12-07 | 2011-05-31 | Nycomed Gmbh | Pharmaceutical preparation comprising an active dispersed on a matrix |
| US7951397B2 (en) | 2002-02-20 | 2011-05-31 | Nycomed Gmbh | Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient |
| US8431154B2 (en) | 2002-02-20 | 2013-04-30 | Takeda Gmbh | Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidone as excipient |
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