KR910004571A - 질소 화합물 - Google Patents
질소 화합물 Download PDFInfo
- Publication number
- KR910004571A KR910004571A KR1019900012389A KR900012389A KR910004571A KR 910004571 A KR910004571 A KR 910004571A KR 1019900012389 A KR1019900012389 A KR 1019900012389A KR 900012389 A KR900012389 A KR 900012389A KR 910004571 A KR910004571 A KR 910004571A
- Authority
- KR
- South Korea
- Prior art keywords
- ethyl
- quinoline
- methoxy
- tetrazol
- alkyl
- Prior art date
Links
- 229910017464 nitrogen compound Inorganic materials 0.000 title 1
- 150000002830 nitrogen compounds Chemical class 0.000 title 1
- -1 3-methoxycarbonylquinolin-4-yloxy Chemical group 0.000 claims 43
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 231100000252 nontoxic Toxicity 0.000 claims 7
- 230000003000 nontoxic effect Effects 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- FSJCYXPMWQPVOS-UHFFFAOYSA-N 2-ethyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=CC=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 FSJCYXPMWQPVOS-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- QDJMXUYLLXTIHJ-UHFFFAOYSA-N 2-methyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=CC=CC2=NC(C)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 QDJMXUYLLXTIHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 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 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- NXHLTRRJYMDMHC-UHFFFAOYSA-N (2-ethylquinolin-6-yl)methanamine Chemical compound C1=C(CN)C=CC2=NC(CC)=CC=C21 NXHLTRRJYMDMHC-UHFFFAOYSA-N 0.000 claims 1
- XUBKQWYBWKSYNC-UHFFFAOYSA-N (2-ethylquinolin-7-yl)methanol Chemical compound C1=CC(CO)=CC2=NC(CC)=CC=C21 XUBKQWYBWKSYNC-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- IGGLDYAOSSEPJI-UHFFFAOYSA-N 2-ethyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline-6-carbonitrile Chemical compound C=12C=C(C#N)C=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 IGGLDYAOSSEPJI-UHFFFAOYSA-N 0.000 claims 1
- UFMAOAQSWIMXPH-UHFFFAOYSA-N 2-ethyl-5,6,7-trimethoxyquinoline Chemical compound COC1=C(OC)C(OC)=CC2=NC(CC)=CC=C21 UFMAOAQSWIMXPH-UHFFFAOYSA-N 0.000 claims 1
- VAHCQIPIEIFFLV-UHFFFAOYSA-N 2-ethyl-6,7-dimethoxyquinoline Chemical compound C1=C(OC)C(OC)=CC2=NC(CC)=CC=C21 VAHCQIPIEIFFLV-UHFFFAOYSA-N 0.000 claims 1
- ALVFJERTMZQZLM-UHFFFAOYSA-N 2-ethyl-6-fluoro-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=C(F)C=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 ALVFJERTMZQZLM-UHFFFAOYSA-N 0.000 claims 1
- MJLRQHITGCIWMF-UHFFFAOYSA-N 2-ethyl-6-fluoroquinoline Chemical compound C1=C(F)C=CC2=NC(CC)=CC=C21 MJLRQHITGCIWMF-UHFFFAOYSA-N 0.000 claims 1
- RVOVQMXVIYSHDX-UHFFFAOYSA-N 2-ethyl-6-methylsulfanyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=C(SC)C=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 RVOVQMXVIYSHDX-UHFFFAOYSA-N 0.000 claims 1
- DSSYCNGGYDHPMB-UHFFFAOYSA-N 2-ethyl-6-methylsulfanylquinoline Chemical compound C1=C(SC)C=CC2=NC(CC)=CC=C21 DSSYCNGGYDHPMB-UHFFFAOYSA-N 0.000 claims 1
- WKPMEBRCZJUODK-UHFFFAOYSA-N 2-ethyl-6-propan-2-yloxy-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinoline Chemical compound C=12C=C(OC(C)C)C=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 WKPMEBRCZJUODK-UHFFFAOYSA-N 0.000 claims 1
- MSCYXPWZCOHWQV-UHFFFAOYSA-N 2-ethyl-6-propan-2-yloxyquinoline Chemical compound C1=C(OC(C)C)C=CC2=NC(CC)=CC=C21 MSCYXPWZCOHWQV-UHFFFAOYSA-N 0.000 claims 1
- MIHWHMRWXQEAGH-UHFFFAOYSA-N 2-ethylquinolin-6-ol Chemical compound C1=C(O)C=CC2=NC(CC)=CC=C21 MIHWHMRWXQEAGH-UHFFFAOYSA-N 0.000 claims 1
- XCIZVKSCLVSDHN-UHFFFAOYSA-N 2-ethylquinoline Chemical compound C1=CC=CC2=NC(CC)=CC=C21 XCIZVKSCLVSDHN-UHFFFAOYSA-N 0.000 claims 1
- JAGWFYGPTIYWTR-UHFFFAOYSA-N 6-(2-fluoroethoxy)-2-methylquinoline Chemical compound FCCOC=1C=C2C=CC(=NC2=CC=1)C JAGWFYGPTIYWTR-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- VEUWFLRDJJOYHX-UHFFFAOYSA-N [2-ethyl-4-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methoxy]quinolin-6-yl]methanamine Chemical compound C=12C=C(CN)C=CC2=NC(CC)=CC=1OCC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 VEUWFLRDJJOYHX-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- ASVSDYXTSKFHNN-UHFFFAOYSA-N bromo-chloro-ethoxy-fluoro-methoxy-lambda5-iodane Chemical compound COI(Br)(Cl)(F)OCC ASVSDYXTSKFHNN-UHFFFAOYSA-N 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 claims 1
- 150000007660 quinolones Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 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
- C07D215/20—Oxygen atoms
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
내용 없음.
Description
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Claims (13)
- 일반식 I의 퀴놀린 유도체, 또는 메틸 2-[(3-메톡시카보닐퀴놀린-4-일옥시)메틸]벤조에이트를 제외한 그것의 비독성 염.식 중, R1은 수소, (1-8C)알킬, (3-8C) 사이클로알킬, 페닐 또는 하나 그 이상의 플루오로 치환체를 포함하거나 또는 (3-8C) 사이클로알킬, 하이드록시, (1-4C)알콕시 또는 페닐 치환체를 가지는 치환된 (1-4C)알킬; R2는 수소, (1-8C)알킬, (3-8C) 사이클로알킬, (3-8C)사이클로알킬-(1-4C)알킬, 카복시, (1-4C)알콕시카보닐, 시아노, 니트로, 페닐 또는 페닐(1-4C) 알킬; R3및 R4는 수소, (1-4C)알킬, (1-4C)알콕시, 플루오로 (1-4C)알콕시, 할로게노, 하이드록시, 트리플루오로메틸, 시아노, 니트로, 아미노, (1-4C)알카노일아미노, 6C 까지의 알킬아미노 및 디알킬아미노, 디알킬아미노-(3-8C)알킬, (1-4C)알카노일, 카바모일, 7C 까지의 N-알킬카바모일 및 디-(N-알킬) 카보모일, 카복시, (1-4C)알콕시카보닐, (1-6C) 알킬티오, (1-6C)알킬설피닐, (1-6C)알킬설포닐 및 아미노, 하이드록시 또는 (1-4C)알콕시 치환체를 가지는 치환된 (1-4C)알킬에서 독립적으로 선택; 또는 R3및 R4는 일반식 I 벤젠 부분의 근접 탄소 원자에 부착되어 함께 (1-4C)알킬렌디옥시를 형성; Ra 및 R5는 수소, (1-4C)알킬, (1-4C)알콕시, 할로게노, 트리플루오로메틸, 시아노 및 니트로에서 독립적으로 선택; A는 메틸렌; X는 (1-4C)알킬, (1-4C)알콕시, 할로게노, 트리플루오로메틸, 시아노 및 니트로에서 선택된 치환체를 임의로 가지는 페닐렌, 또는 근접 페닐 그룹과 A 부분 사이의 직접 결합; Z는 1H-테트라졸-5-일, -CO·NH(1H-테트라졸-5-일) 또는 -CO·OR6또는 -CO·NH·SO2·R7R6은 수소 또는 생리학적으로 허용 가능한 알콜 또는 페닐의 비독성이고 생물학적으로 분해가능한 잔사, 및 R7은 (1-6C)알킬, (3-8C)사이클로알킬 또는 페닐; 및 혹종의 상기 페닐 부분은 치환되지 않았거나 또는 (1-4C)알콕시, (1-4C)알콕시, 할로게노, 시아노 및 트리플루오로메틸에서 독립적으로 선택된 하나 또는 두 치환체를 가짐.
- 제1항에 있어서, R′이 수소, 메틸, 에틸, 프로필, 부틸, 이소부틸, 2차-부틸, 펜틸, 헥실, 사이클로프로필, 사이클로펜틸, 사이클로헥실, 페닐, 플루오로메틸, 트리플루오로메틸, 2,2,2-트리플루오로에틸, 펜타플루오로에틸, 하이드록시에틸, 1-하이드록시에틸, 2-하이드록시에틸, 사이클로프로필메틸, 사이클로펜틸메틸, 사이클로헥실메틸, 2-메톡시에틸, 2-에톡시에틸, 벤질, 1-페닐에틸 또는 2-페닐에틸이고; R2가 수소, 메틸, 에틸, 프로필, 부틸, 이소부틸, 2차-부틸, 펜틸, 헥실, 하이클프로필, 사이클로펜틸, 사이클로헥실, 사이클로프로필메틸, 사이클로펜틸메틸, 사이클로헥실메틸, 2-사이클로펜틸-에틸, 카복시, 메톡시카보닐, 에톡시카보닐, 프로폭시카보닐, 시아노, 니트로, 페닐, 벤질, 1-페닐에틸 또는 2-페닐에틸이고; R3및 R4가 수소, 메틸, 에틸, 메톡시, 에톡시, 트리플루오로메톡시, 2-플루오로에톡시, 2,2,2-트리플루오로에톡시, 3,3,3-트리플루오로프로폭시, 플루오로, 클로로, 브로모, 요델, 하이드록시, 트리플루오로메틸, 시아노, 니트로, 아미노, 포름아미노, 아세트아미도, 프로판아미도, 메틸아미도, 에틸아미노, 부틸아미노, 디메틸아미노, 디에틸아미노, 디프로필아미노, 디메틸아미노메틸, 2-(디메틸아미노)에틸, 2-(디에틸아미노)에틸, 3-(디에틸아미노) 프로필, 포밀, 아세틸, 부티릴, 카바모일, N-메틸카바모일, N-에틸카바모일, N,N-디메틸카바모일, N,N-디에틸카바모일, 카복시, 메톡시카보닐, 에톡시카보닐, 프로폭시카보닐, 메틸티오, 에틸티오, 부틸티오, 메틸설피닐, 에틸설피닐, 부틸설피닐, 메틸설포닐, 에틸설포닐, 부틸설포닐, 하이드록시메틸, 1-하이드록시에틸, 2-하이드록시에틸, 아미노메틸, 2-아미노에틸, 2-메톡시에틸 및 2-에톡시에틸에서 독립적으로 선택되거나, 또는 R3및 R4는 일반식 I 벤젠 부분의 근접 탄소 원자에 부착되어 함께 메틸렌디옥시 또는 에틸렌옥시를 형성하고; Ra 및 R5는 수소, 메틸, 에틸, 메톡시, 에톡시, 플루오로, 클로로, 브로모, 요오드, 트리플루오로메틸, 시아노 및 니트로에서 독립적으로 선택되고; X는 메틸, 에틸, 메톡시, 에톡시, 플루오로, 클로로, 브로모, 요오도, 트리플루오로메틸, 시아노 및 니트로에서 선택된 치환체를 임의로 가지는 페닐렌이거나, 또는 X는 근접 페닐 그룹 및 AQNQNS 사이의 직접 결합이고; R6은 수소 또는 (1-6C)알칸올, 또는 페놀 또는 글리세롤으로부터 유도된 잔사이고; R7은 메틸, 에틸프로필, 이소프로필, 부틸, 펜틸, 사이클로부틸, 사이클로펜틸, 사이클로헥실 또는 페닐이고, 상기 혹종의 페닐 부분은 치환되지 않았거나 또는 메틸, 에틸, 메톡시, 에톡시, 플루오로, 클로로, 브로모, 시아노 및 트리플루오로메틸에서 독립적으로 선택된 하나 또는 두 치환체를 가지는 화합물.
- 제1항에 있어서, R1이 수소, (1-8C)알킬, (3-8C)사이클로알킬, (3-8C)사이클로알킬-(1-4C)알킬, 페닐 또는 페닐이고, R3, R4및 R5가 수소, (1-4C)알킬, (1-4C)알콕시, 할로게노, 트리플루오로메틸, 시아노 및 니트로에서 독립적으로 선택되고 Ra가 수소인 화합물.
- 제1항에 있어서, R3, R4가 수소, (1-4C)알킬, (1-4C)알콕시, 플루오로(1-4C)알콕시, 할로게노, 트리플루오로메틸, 시아노, 니트로, 아미노, (1-4C)알카노일아미노, 6C 까지의 알킬아미노, 디알킬아미노-(3-8C)의 알킬, (1-4C)알카노일, 카바모일, 7C 까지의 N-알킬카바모일 및 디-(N-알킬)카바모일, 카복시, (1-4C)알콕시카보닐, (1-6C)알킬티오, (1-6C)알킬설포닐, (1-6C)알킬설포닐 및 아미노, 하이드록시 또는 (1-4C)알콕시 치환체를 가지는 치환된 (1-4C)알킬에서 독립적으로 선택되거나; 또는 R3및 R4는 일반식 I 벤젠 부분의 근접 탄소 원자에 부착된 (1-4C)알킬렌디옥시를 형성하고; Ra가 수소인 화합물.
- 일반식 Ia이 화합물과 그것의 비독성 염.식중 R1, R2, R3및 R4는 제1항에서 제4항까지의 정의 중 어느 하나이고, R5는 수소이고, Z1은 카복시 또는 1H-테트라졸-5-일.
- 제1항, 제2항 또는 제5항중 어느 한 항에 있어서, 부착된 치환체 R1, R2, R3및 R4존재하면 Ra와 함께 퀴놀린 부분이 2-메틸퀴놀린, 2-에틸퀴놀린, 2-에틸-6-메톡시퀴놀린, 6,7-디메톡시-2-에틸퀴놀린, 2-에틸-5,6,7-트리메톡시퀴놀린, 2-에틸-6-하이드록시퀴놀린, 2-에틸-6-메틸티오퀴놀린, 2-에틸-7-하이드록시메틸퀴놀린, 2-메틸-6-(2-플루오로에톡시)퀴놀린, 2-에틸-6-(2,2,2-트리플루오로에톡시)퀴놀린, 2-에틸-6-카복-스아미드퀴놀린, 2-에틸-6-플루오로퀴놀린, 2-에틸-6-이소프로폭시퀴놀린 및 6-아미노메틸-2-에틸퀴놀린에서 선택되고; 치환체 O, A, X-가 퀴놀린 환의 4-위치에 부착된 화합물.
- 2-메틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 6-8-디메틸-2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-6-메틸티오-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 6-에틸-7-하이드록시메틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-6-(2-트리플루오로에톡시)-4-[2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-6-(2,2,2-트리플루오로에톡시)-4-[2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 6-카복스아미도-2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 6 - 시아노-2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-6-플루오로-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-6-이소프로폭시-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 및 6-아미노메틸-2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린으로 부터 선택된 일반식 I의 화합물 및 그것의 비독성 염.
- 2-메틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 2-에틸-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린; 및 2-에틸-6-이스프로폭시-4-[(2′-(1H-테트라졸-5-일)바이페닐-4-일)메톡시]퀴놀린으로 부터 선택된 일반식 I의 화합물; 및 그것의 비독성 염.
- 전기한 항의 어느 한 항에 있어서, 생리학적으로 허용 가능한 음이온을 형성하는 산과의 염, 일반식 I 화합물이 산성일 때, 알카리 금속, 알카리 토금속, 알루미늄 및 암모늄염 및 생리학적으로 허용가능한 음이온을 제공하는 유기 염기와의 염으로부터 선택된 염.
- (a) Z가 카복시인 화합물을 제조하기 위해, 일반식 II의 카복실산 유도체를식 중, Q는 (1-6C)알콕시카보닐, 페녹시카보닐, 벤질옥시카보닐 및 카바모일에서 선택된 보호된 카복시 그룹 카복시로 전환시키거나; (b) Z가 테트라졸일인 일반식 I 화합물을 제조하기 위해, 일반식 III의 화합물을식 중, L은 테트라졸일 부분의 질소에 고정된 적당한 보호 그룹 탈보호하거나; (c) 일반식 I의 퀴놀론을식중 R1은 수소가 아님. 일반식 V의 화합물로 알킬화하거나; 또는식 중, Hal은 적당한 이탈 그룹(d) 일반식 VII의 할로게노퀴놀린을식중 Y1은 할로게노 그룹 일반식 VIII의 알콜과 반응시키고 ;식중 R1, R2, R3및 R4, R5, R6, R7, Ra, A, X, 및 X는 다른 언급이 없는 한 제1항에서 제6항까지의 어느 한 항에 따르는 의미를 가짐 그후에 Z가 1H-테트라졸-5-일인 일반식 I 화합물이 필요할 때, Z가 -CO.OR1인 일반식 I의 화합물을 표준 조건하에 당해 니트릴로 전환시키고, 다음에 니트릴을 아지드와 반응시키고; Z가 -CO, NH, SO2, R7또는 -CO, OR6(R6은 수소가 아임)인 일반식 I 화합물이 필요할 때, Z가 카복시(또는 그 산의 반응성 유도체)인 일반식 I의 카복실산을 NH2·SO2R7의 설폰아미드 또는 HO.R6의 하이드록시 화합물 또는 그것의 염과 반응시키고; 일반식 I의 화합물의 비독성 염이 필요할 때, 적당한 산 또는 염기를 제공하는 생리학적으로 허용가능한 이온과 반응시키거나 또는 기타 통상적인 염 형성 과정에 의해 얻고; 일반식 I 화합물의 광학적 활성 형태가 필요할 때, 상기 방법(a)-(d)중 하나를 광학적 활성인 출발 물질로 수행하거나, 또는 Z가 산성 그룹인 일반식 I 화합물의 라세미 형태는 적당한 유기 염기의 광학 활성 형태와 반응시키고 형성된 염의 디아스테레오 아이소머 혼합물을 분리하고 통상적인 처리방법에 의해 산으로 일반식 I 화합물의 필요한 광학 활성 형태를 유리시킴에 의해 분리하는 것을 특징으로하는 제1항, 제5항, 제7항 또는 제8항의 일반식 I 화합물 또는 그것의 비독성 염을 제조하는 방법.
- 제1항에서 제9항까지의 일반식 I 또는 Ia 화합물, 또는 그것의 비독성 염과 함께 제약학적으로 허용가능한 희석제 또는 담체로 구성되는 제약학적 조성물.
- R1, R2, R3및 R4, R5, R6, R7, Ra, A 및 X가 제1항에서 제6항까지의 어느 한 항의 의미를 가지고 Q가 (1-6C)알콕시카보닐, 페녹시카보닐, 벤질옥시카보닐 및 카바모일에서 선택된 보호된 카복시 그룹인 일반식 II 의 화합물.
- R1, R2, R3, R4, R5, Ra, A 및 X가 제1항에서 제6항까지의 어느 한 항의 정의를 가지고, L이 보호 그룹인 일반식 III의 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898918402A GB8918402D0 (en) | 1989-08-11 | 1989-08-11 | Nitrogen compounds |
| GB8918402.2 | 1989-08-11 | ||
| GB9003187.3 | 1990-02-13 | ||
| GB909003187A GB9003187D0 (en) | 1990-02-13 | 1990-02-13 | Nitrogen compounds |
Publications (1)
| Publication Number | Publication Date |
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| KR910004571A true KR910004571A (ko) | 1991-03-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900012389A KR910004571A (ko) | 1989-08-11 | 1990-08-11 | 질소 화합물 |
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| US (1) | US5444071A (ko) |
| EP (1) | EP0412848B1 (ko) |
| JP (1) | JP3010056B2 (ko) |
| KR (1) | KR910004571A (ko) |
| CN (1) | CN1050187A (ko) |
| AP (1) | AP161A (ko) |
| AT (1) | ATE117294T1 (ko) |
| AU (1) | AU623546B2 (ko) |
| BG (1) | BG92674A (ko) |
| DE (1) | DE69016125T2 (ko) |
| FI (1) | FI903966A0 (ko) |
| HU (1) | HUT54991A (ko) |
| IE (1) | IE902909A1 (ko) |
| NO (1) | NO903525L (ko) |
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| PL (1) | PL286445A1 (ko) |
| PT (1) | PT94960A (ko) |
| YU (1) | YU155290A (ko) |
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- 1990-08-10 HU HU904961A patent/HUT54991A/hu unknown
- 1990-08-10 EP EP90308855A patent/EP0412848B1/en not_active Expired - Lifetime
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- 1990-08-10 NZ NZ234854A patent/NZ234854A/xx unknown
- 1990-08-10 NO NO90903525A patent/NO903525L/no unknown
- 1990-08-10 PT PT94960A patent/PT94960A/pt not_active Application Discontinuation
- 1990-08-10 YU YU155290A patent/YU155290A/sh unknown
- 1990-08-10 PL PL28644590A patent/PL286445A1/xx unknown
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- 1990-08-10 FI FI903966A patent/FI903966A0/fi not_active Application Discontinuation
- 1990-08-10 AP APAP/P/1990/000197A patent/AP161A/en active
- 1990-08-11 CN CN90106923A patent/CN1050187A/zh active Pending
- 1990-08-11 KR KR1019900012389A patent/KR910004571A/ko not_active Application Discontinuation
- 1990-08-13 JP JP2214223A patent/JP3010056B2/ja not_active Expired - Lifetime
-
1993
- 1993-05-04 US US08/058,825 patent/US5444071A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BG92674A (bg) | 1993-12-24 |
| AU623546B2 (en) | 1992-05-14 |
| EP0412848A2 (en) | 1991-02-13 |
| YU155290A (sh) | 1993-05-28 |
| DE69016125T2 (de) | 1995-06-01 |
| ATE117294T1 (de) | 1995-02-15 |
| NZ234854A (en) | 1993-02-25 |
| JPH03169863A (ja) | 1991-07-23 |
| EP0412848A3 (en) | 1991-04-10 |
| NO903525L (no) | 1991-02-12 |
| NO903525D0 (no) | 1990-08-10 |
| FI903966A0 (fi) | 1990-08-10 |
| US5444071A (en) | 1995-08-22 |
| AP161A (en) | 1991-12-20 |
| HUT54991A (en) | 1991-04-29 |
| DE69016125D1 (de) | 1995-03-02 |
| JP3010056B2 (ja) | 2000-02-14 |
| CN1050187A (zh) | 1991-03-27 |
| PT94960A (pt) | 1991-04-18 |
| AP9000197A0 (en) | 1990-10-31 |
| IE902909A1 (en) | 1991-02-27 |
| EP0412848B1 (en) | 1995-01-18 |
| HU904961D0 (en) | 1991-01-28 |
| AU6095590A (en) | 1991-02-14 |
| PL286445A1 (en) | 1991-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19900811 |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |