JPH0696578B2 - 三還式化合物 - Google Patents

三還式化合物

Info

Publication number: JPH0696578B2
Authority: JP; Japan
Prior art keywords: compound; group; methyl; salt; oxo
Prior art date: 1986-09-12
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.): Expired - Fee Related

Application number

JP62227579A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63132891A (ja

Inventor

一輝横瀬

信夫新間

みや子鎌田

雅弘青木

達男大塚

Original Assignee

エフ・ホフマン―ラロシユアーゲー

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.)

1986-09-12

Filing date

1987-09-12

Publication date

1994-11-30

1987-09-12 Application filed by エフ・ホフマン―ラロシユアーゲー filed Critical エフ・ホフマン―ラロシユアーゲー

1988-06-04 Publication of JPS63132891A publication Critical patent/JPS63132891A/ja

1994-11-30 Publication of JPH0696578B2 publication Critical patent/JPH0696578B2/ja

2009-11-30 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 339
-1 benzyloxycarbonylamino group Chemical group 0.000 claims description 308
150000003839 salts Chemical class 0.000 claims description 196
239000012453 solvate Substances 0.000 claims description 108
125000000217 alkyl group Chemical group 0.000 claims description 76
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
125000003277 amino group Chemical group 0.000 claims description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 25
238000000034 method Methods 0.000 claims description 25
125000003282 alkyl amino group Chemical group 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
WYFAFWRMEXHKPN-UHFFFAOYSA-N 2h-1,2,3-benzoxadiazine-6-carboxylic acid Chemical compound O1NN=CC2=CC(C(=O)O)=CC=C21 WYFAFWRMEXHKPN-UHFFFAOYSA-N 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
BBKSHHFYIULIKT-UHFFFAOYSA-N 3H-4,1,2-benzoxadiazine-6-carboxylic acid Chemical compound N1=NCOC2=CC(C(=O)O)=CC=C21 BBKSHHFYIULIKT-UHFFFAOYSA-N 0.000 claims description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
150000001241 acetals Chemical class 0.000 claims description 6
150000001728 carbonyl compounds Chemical class 0.000 claims description 6
150000002084 enol ethers Chemical class 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229920000642 polymer Polymers 0.000 claims description 6
YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
208000015181 infectious disease Diseases 0.000 claims description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
150000003948 formamides Chemical class 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000003814 drug Substances 0.000 claims 5
125000003341 7 membered heterocyclic group Chemical group 0.000 claims 3
239000000825 pharmaceutical preparation Substances 0.000 claims 3
150000001735 carboxylic acids Chemical class 0.000 claims 2
RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 claims 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
230000003449 preventive effect Effects 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 44
238000003786 synthesis reaction Methods 0.000 description 43
239000002904 solvent Substances 0.000 description 42
238000002844 melting Methods 0.000 description 40
230000008018 melting Effects 0.000 description 40
239000000203 mixture Substances 0.000 description 40
230000015572 biosynthetic process Effects 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
238000001914 filtration Methods 0.000 description 19
239000002244 precipitate Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
239000012046 mixed solvent Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
239000002585 base Substances 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
239000012299 nitrogen atmosphere Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
230000000844 anti-bacterial effect Effects 0.000 description 8
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000007327 hydrogenolysis reaction Methods 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
GORYSGPURSAYCZ-UHFFFAOYSA-N 6,7-difluoro-8-hydroxy-1-(methylamino)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(O)=C2N(NC)C=C(C(O)=O)C(=O)C2=C1 GORYSGPURSAYCZ-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000010446 mirabilite Substances 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
125000004193 piperazinyl group Chemical group 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
JLGCBXBYXNVQMY-UHFFFAOYSA-N 6,7-difluoro-4-oxo-8-phenylmethoxy-1H-quinoline-3-carboxylic acid Chemical compound C1=CC=C(C=C1)COC2=C3C(=CC(=C2F)F)C(=O)C(=CN3)C(=O)O JLGCBXBYXNVQMY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
229910000085 borane Inorganic materials 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
125000006317 cyclopropyl amino group Chemical group 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
244000005700 microbiome Species 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000047 product Substances 0.000 description 4
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000204031 Mycoplasma Species 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
DSOICHFMGRBFCM-UHFFFAOYSA-N benzyl n-pyrrolidin-3-ylcarbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1 DSOICHFMGRBFCM-UHFFFAOYSA-N 0.000 description 3
150000007942 carboxylates Chemical class 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
238000001816 cooling Methods 0.000 description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 3
239000012156 elution solvent Substances 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 2
DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 description 2
HWALAYKNOBYNBD-UHFFFAOYSA-N 1-(methylamino)-4-oxoquinoline-3-carboxylic acid Chemical compound CNN1C=C(C(C2=CC=CC=C12)=O)C(=O)O HWALAYKNOBYNBD-UHFFFAOYSA-N 0.000 description 2
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
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238000007912 intraperitoneal administration Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
ZOBHKNDSXINZGQ-UHFFFAOYSA-N n'-ethyl-n,n,n'-trimethylethane-1,2-diamine Chemical compound CCN(C)CCN(C)C ZOBHKNDSXINZGQ-UHFFFAOYSA-N 0.000 description 1
DDROADVTQNAKPF-UHFFFAOYSA-N n,n-dimethyl-1-pyrrolidin-3-ylmethanamine Chemical compound CN(C)CC1CCNC1 DDROADVTQNAKPF-UHFFFAOYSA-N 0.000 description 1
QTHJLIPBZCTYNL-UHFFFAOYSA-N n,n-dimethyl-n'-pyrrolidin-3-ylmethanimidamide Chemical compound CN(C)C=NC1CCNC1 QTHJLIPBZCTYNL-UHFFFAOYSA-N 0.000 description 1
BQGLWXRYJXNTCV-UHFFFAOYSA-N n-(2-iodoethyl)acetamide Chemical compound CC(=O)NCCI BQGLWXRYJXNTCV-UHFFFAOYSA-N 0.000 description 1
RJASJOJQSLXLNG-UHFFFAOYSA-N n-(piperidin-4-ylmethyl)ethanamine Chemical compound CCNCC1CCNCC1 RJASJOJQSLXLNG-UHFFFAOYSA-N 0.000 description 1
BEAWFOYVSBYVCD-UHFFFAOYSA-N n-(pyrrolidin-3-ylmethyl)acetamide Chemical compound CC(=O)NCC1CCNC1 BEAWFOYVSBYVCD-UHFFFAOYSA-N 0.000 description 1
BUQMHUKZYMREQT-UHFFFAOYSA-N n-(pyrrolidin-3-ylmethyl)ethanamine Chemical compound CCNCC1CCNC1 BUQMHUKZYMREQT-UHFFFAOYSA-N 0.000 description 1
ZAHSSMDTFVJWHQ-UHFFFAOYSA-N n-[(4-hydroxypyrrolidin-3-yl)methyl]acetamide Chemical compound CC(=O)NCC1CNCC1O ZAHSSMDTFVJWHQ-UHFFFAOYSA-N 0.000 description 1
QJFOBFBLCAKSEE-UHFFFAOYSA-N n-[(4-methylpyrrolidin-3-yl)methyl]ethanamine Chemical compound CCNCC1CNCC1C QJFOBFBLCAKSEE-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
SNWZNERLHBKKCE-UHFFFAOYSA-N n-ethyl-4-methoxypyrrolidin-3-amine Chemical compound CCNC1CNCC1OC SNWZNERLHBKKCE-UHFFFAOYSA-N 0.000 description 1
VARJMVYCDHQKCG-UHFFFAOYSA-N n-ethylpiperidin-4-amine Chemical compound CCNC1CCNCC1 VARJMVYCDHQKCG-UHFFFAOYSA-N 0.000 description 1
OPCPWFHLFKAUEA-UHFFFAOYSA-N n-ethylpyrrolidin-3-amine Chemical compound CCNC1CCNC1 OPCPWFHLFKAUEA-UHFFFAOYSA-N 0.000 description 1
QUKPMCFHCLEPOV-UHFFFAOYSA-N n-methyl-1-(3-methylpyrrolidin-3-yl)methanamine Chemical compound CNCC1(C)CCNC1 QUKPMCFHCLEPOV-UHFFFAOYSA-N 0.000 description 1
WVPCDSLZKFKUSR-UHFFFAOYSA-N n-methyl-1-(4-methylpyrrolidin-3-yl)methanamine Chemical compound CNCC1CNCC1C WVPCDSLZKFKUSR-UHFFFAOYSA-N 0.000 description 1
NISMDRPTXMAGKX-UHFFFAOYSA-N n-methyl-1-(4-phenylpyrrolidin-3-yl)methanamine Chemical compound CNCC1CNCC1C1=CC=CC=C1 NISMDRPTXMAGKX-UHFFFAOYSA-N 0.000 description 1
RNUCZCMDLWNCFD-UHFFFAOYSA-N n-methyl-1-piperidin-4-ylmethanamine Chemical compound CNCC1CCNCC1 RNUCZCMDLWNCFD-UHFFFAOYSA-N 0.000 description 1
JVODWNWKCOVKTO-UHFFFAOYSA-N n-methyl-1-pyrrolidin-3-ylmethanamine Chemical compound CNCC1CCNC1 JVODWNWKCOVKTO-UHFFFAOYSA-N 0.000 description 1
QWVOIUJSOWUXNE-UHFFFAOYSA-N n-methyl-n-(pyrrolidin-3-ylmethyl)ethanamine Chemical compound CCN(C)CC1CCNC1 QWVOIUJSOWUXNE-UHFFFAOYSA-N 0.000 description 1
FHTGZDVYPCEHFQ-UHFFFAOYSA-N n-methylpiperidin-4-amine Chemical compound CNC1CCNCC1 FHTGZDVYPCEHFQ-UHFFFAOYSA-N 0.000 description 1
NGZYRKGJWYJGRS-UHFFFAOYSA-N n-methylpyrrolidin-3-amine Chemical compound CNC1CCNC1 NGZYRKGJWYJGRS-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
229960003868 paraldehyde Drugs 0.000 description 1
239000006072 paste Substances 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
150000004976 peroxydisulfates Chemical class 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 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
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-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
229960004889 salicylic acid Drugs 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 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
125000001425 triazolyl group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
UAIFZYSPVVBOPN-UHFFFAOYSA-N trimethyl(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(C)C UAIFZYSPVVBOPN-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP62227579A 1986-09-12 1987-09-12 三還式化合物 Expired - Fee Related JPH0696578B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP86112619		1986-09-12
EP86112619.1		1986-09-12

Related Child Applications (2)

Application Number	Title	Priority Date	Filing Date
JP6133894A Division JPH0826030B2 (ja)	1986-09-12	1994-05-25	ピリドベンゾオキサジアジン誘導体
JP6133905A Division JPH0819120B2 (ja)	1986-09-12	1994-05-25	キノリン誘導体

Publications (2)

Publication Number	Publication Date
JPS63132891A JPS63132891A (ja)	1988-06-04
JPH0696578B2 true JPH0696578B2 (ja)	1994-11-30

Family

ID=8195410

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
JP62227579A Expired - Fee Related JPH0696578B2 (ja)	1986-09-12	1987-09-12	三還式化合物
JP6133894A Expired - Lifetime JPH0826030B2 (ja)	1986-09-12	1994-05-25	ピリドベンゾオキサジアジン誘導体
JP6133905A Expired - Lifetime JPH0819120B2 (ja)	1986-09-12	1994-05-25	キノリン誘導体

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
JP6133894A Expired - Lifetime JPH0826030B2 (ja)	1986-09-12	1994-05-25	ピリドベンゾオキサジアジン誘導体
JP6133905A Expired - Lifetime JPH0819120B2 (ja)	1986-09-12	1994-05-25	キノリン誘導体

Country Status (22)

Country	Link
JP (3)	JPH0696578B2 (cs)
KR (1)	KR960002857B1 (cs)
CN (1)	CN1017800B (cs)
AT (1)	AT389119B (cs)
AU (1)	AU602534B2 (cs)
CA (1)	CA1336905C (cs)
CZ (1)	CZ281195B6 (cs)
DK (1)	DK173330B1 (cs)
DZ (1)	DZ1124A1 (cs)
FI (1)	FI86428C (cs)
HU (1)	HU199481B (cs)
IE (1)	IE61624B1 (cs)
IL (1)	IL83814A (cs)
MC (1)	MC1850A1 (cs)
MX (1)	MX8302A (cs)
NO (1)	NO169125C (cs)
NZ (1)	NZ221681A (cs)
PH (1)	PH23930A (cs)
PT (1)	PT85686B (cs)
SK (1)	SK278990B6 (cs)
ZA (1)	ZA876636B (cs)
ZW (1)	ZW16387A1 (cs)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZW16387A1 (en) *	1986-09-12	1988-05-25	Hoffmann La Roche	Tricyclic compounds
US7977327B2 (en)	2004-05-13	2011-07-12	Daiichi Sankyo Company, Limited	Substituted pyrrolidine derivative
US7563805B2 (en) *	2005-05-19	2009-07-21	Daiichi Pharmaceutical Co., Ltd.	Tri-, tetra-substituted-3-aminopyrrolidine derivative
SI2383271T1 (sl)	2006-03-13	2013-10-30	Kyorin Pharmaceutical Co., Ltd.	Aminokinoloni kot inhibitorji gsk-3
BRPI0816798A2 (pt)	2007-09-11	2016-10-11	Activx Biosciences Inc	composto, composição farmacêutica, métodos para inibir a ação do glicogênio sintase cinase-3, e para tratar, prevenir ou melhorar uma doença, uso de um composto, e, artigo de fabricação
CA2699152C (en)	2007-09-12	2015-11-24	Activx Biosciences, Inc.	Spirocyclic aminoquinolones as gsk-3 inhibitors
FR2928150A1 (fr) *	2008-02-29	2009-09-04	Vetoquinol Sa Sa	Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens
EP2145891A1 (en) *	2008-07-09	2010-01-20	Vetoquinol S.A.	9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials
EP2406266B1 (en)	2009-03-11	2013-12-25	Kyorin Pharmaceutical Co., Ltd.	7-cycloalkylaminoquinolones as gsk-3 inhibitors
CN107522718B (zh) *	2017-09-14	2019-11-08	浙江国邦药业有限公司	一种马波沙星的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZW16387A1 (en) *	1986-09-12	1988-05-25	Hoffmann La Roche	Tricyclic compounds

1987
- 1987-08-28 ZW ZW163/87A patent/ZW16387A1/xx unknown
- 1987-09-04 NZ NZ221681A patent/NZ221681A/en unknown
- 1987-09-04 ZA ZA876636A patent/ZA876636B/xx unknown
- 1987-09-07 IL IL83814A patent/IL83814A/xx not_active IP Right Cessation
- 1987-09-07 AU AU78114/87A patent/AU602534B2/en not_active Expired
- 1987-09-09 HU HU874007A patent/HU199481B/hu unknown
- 1987-09-09 DZ DZ870149A patent/DZ1124A1/fr active
- 1987-09-10 MC MC871911A patent/MC1850A1/xx unknown
- 1987-09-11 PH PH35800A patent/PH23930A/en unknown
- 1987-09-11 FI FI873940A patent/FI86428C/fi not_active IP Right Cessation
- 1987-09-11 KR KR1019870010082A patent/KR960002857B1/ko not_active Expired - Lifetime
- 1987-09-11 PT PT85686A patent/PT85686B/pt unknown
- 1987-09-11 CZ CS876604A patent/CZ281195B6/cs not_active IP Right Cessation
- 1987-09-11 SK SK6604-87A patent/SK278990B6/sk unknown
- 1987-09-11 IE IE244487A patent/IE61624B1/en not_active IP Right Cessation
- 1987-09-11 CA CA000546674A patent/CA1336905C/en not_active Expired - Lifetime
- 1987-09-11 NO NO873816A patent/NO169125C/no unknown
- 1987-09-11 DK DK198704772A patent/DK173330B1/da not_active IP Right Cessation
- 1987-09-12 JP JP62227579A patent/JPH0696578B2/ja not_active Expired - Fee Related
- 1987-09-12 CN CN87106838A patent/CN1017800B/zh not_active Expired
- 1987-09-14 MX MX830287A patent/MX8302A/es unknown
- 1987-10-08 AT AT0263887A patent/AT389119B/de not_active IP Right Cessation
1994
- 1994-05-25 JP JP6133894A patent/JPH0826030B2/ja not_active Expired - Lifetime
- 1994-05-25 JP JP6133905A patent/JPH0819120B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ATA263887A (de)	1989-03-15
JPS63132891A (ja)	1988-06-04
CZ660487A3 (en)	1996-04-17
IE872444L (en)	1988-03-12
ZA876636B (en)	1988-07-27
NO169125C (no)	1992-05-13
CZ281195B6 (cs)	1996-07-17
FI86428B (fi)	1992-05-15
PT85686A (en)	1987-10-01
AT389119B (de)	1989-10-25
SK660487A3 (en)	1998-05-06
DZ1124A1 (fr)	2004-09-13
CN87106838A (zh)	1988-05-11
NZ221681A (en)	1990-12-21
AU602534B2 (en)	1990-10-18
DK477287A (da)	1988-03-13
DK173330B1 (da)	2000-07-24
MC1850A1 (fr)	1988-09-30
JPH0826030B2 (ja)	1996-03-13
NO873816L (no)	1988-03-14
IL83814A (en)	1991-09-16
KR960002857B1 (ko)	1996-02-27
PT85686B (pt)	1990-05-31
JPH07138262A (ja)	1995-05-30
FI873940A7 (fi)	1988-03-13
FI873940A0 (fi)	1987-09-11
HUT47294A (en)	1989-02-28
JPH0819120B2 (ja)	1996-02-28
HU199481B (en)	1990-02-28
NO169125B (no)	1992-02-03
NO873816D0 (no)	1987-09-11
KR880003954A (ko)	1988-06-01
AU7811487A (en)	1988-03-17
PH23930A (en)	1990-01-23
MX8302A (es)	1993-12-01
IE61624B1 (en)	1994-11-16
SK278990B6 (sk)	1998-05-06
FI86428C (fi)	1992-08-25
CN1017800B (zh)	1992-08-12
DK477287D0 (da)	1987-09-11
CA1336905C (en)	1995-09-05
JPH07138256A (ja)	1995-05-30
ZW16387A1 (en)	1988-05-25

Publication	Publication Date	Title
US4801584A (en)	1989-01-31	Pyrido(3,2,1-IJ)-1,3,4 benzoxadiazine derivatives
CN102341394B (zh)	2015-04-15	聚(adp-核糖)聚合酶(parp)抑制剂
AU617735B2 (en)	1991-12-05	Derivatives of 7-(1-azetidinyl)-1,4-dihydro-4-oxo-3- guinolinecarboxylic acids, their preparation and application as medicines
US4705788A (en)	1987-11-10	Novel antibacterial 7-amino-1(substituted cyclopropyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
JP3046035B2 (ja)	2000-05-29	５―アルキルキノロンカルボン酸類
PT724583E (pt)	2001-03-30	Compostos de piridazino quinolina
HU179927B (en)	1983-01-28	Process for preparing naphthyridine derivatives
IE892293L (en)	1990-01-15	Pyrrolidinyl-3-quinolone and naphthyridone- carboxylic acid¹derivatives
US4843070A (en)	1989-06-27	Substituted thiazetoquinoline-3-carboxylic acids and pharmaceutically acceptable salts thereof
JPS63258855A (ja)	1988-10-26	５−置換キノロン−及びナフチリドンカルボン酸誘導体
JPH0696578B2 (ja)	1994-11-30	三還式化合物
JPH01211587A (ja)	1989-08-24	複素環置換されたキノリン―カルボン酸
IE860062L (en)	1986-07-10	Naphthyridines and pyridines
JPS62169789A (ja)	1987-07-25	７−（アザビシクロアルキル）−キノロンカルボン酸及び−ナフチリドンカルボン酸誘導体
TW201300386A (zh)	2013-01-01	２－胺基－３－（咪唑－２－基）－吡啶－４－酮衍生物、其製備方法及其治療用途
US4864023A (en)	1989-09-05	Pyrido(3,2,1-IJ)-1,3,4-benzoxadiazine derivatives
US4616019A (en)	1986-10-07	Naphthyridine antibacterial compounds
US4533663A (en)	1985-08-06	Quino-benzothiazine antibacterial compounds
US6114351A (en)	2000-09-05	N-oxides as antibacterial agents
CA2447675A1 (en)	2002-11-28	Novel pyridylmethylaminopyrimidines
Leysen	1994	Synthesis and biological evaluation of new quinolones as potential antibacterial agents
JPH0413355B2 (cs)	1992-03-09
CS235545B2 (cs)	1985-05-15	Způsob přípravy derivátů 1-ethyl nebo vinyl-6-halogen-1,4-dihydro-4- oxo-7-/1 -piperazinyl/-!,8-nafthyridinu
HU203100B (en)	1991-05-28	Process for producing quinoline-carboxylic acids substituted with heterocyclic group
CS270245B2 (en)	1990-06-13	Method of new acyl derivatives production

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