JPH0748367A - Bicycloamine derivative - Google Patents
Bicycloamine derivativeInfo
- Publication number
- JPH0748367A JPH0748367A JP6079850A JP7985094A JPH0748367A JP H0748367 A JPH0748367 A JP H0748367A JP 6079850 A JP6079850 A JP 6079850A JP 7985094 A JP7985094 A JP 7985094A JP H0748367 A JPH0748367 A JP H0748367A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- azabicyclo
- formula
- acid
- salt
- 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
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- MQAXETHJRNPNOG-UHFFFAOYSA-N N-(3-azabicyclo[3.1.0]hexan-1-ylmethyl)-2,2,2-trifluoroacetamide Chemical compound C1C2C1(CNC2)CNC(=O)C(F)(F)F MQAXETHJRNPNOG-UHFFFAOYSA-N 0.000 claims 1
- WCUDPBFMWUECIV-UHFFFAOYSA-N methyl N-(3-azabicyclo[3.1.0]hexan-1-yl)carbamate Chemical compound COC(=O)NC12CC1CNC2 WCUDPBFMWUECIV-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 40
- YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical class OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 abstract description 11
- 239000003054 catalyst Substances 0.000 abstract description 8
- 125000006239 protecting group Chemical group 0.000 abstract description 7
- 238000007796 conventional method Methods 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 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 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 β-lactam compound Chemical class 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 2
- BOHSMHNKEIRAEH-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrile Chemical compound C1C2(C#N)CC2CN1CC1=CC=CC=C1 BOHSMHNKEIRAEH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZPJCNJMJYMXOHV-UHFFFAOYSA-N 2-benzyl-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole Chemical compound C1C2CCCC2CN1CC1=CC=CC=C1 ZPJCNJMJYMXOHV-UHFFFAOYSA-N 0.000 description 1
- AFPJBSVKXQEAPX-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane-1-carboxamide Chemical compound NC(=O)C12CC1CN(Cc1ccccc1)C2 AFPJBSVKXQEAPX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VXJRQGHURCVYIS-UHFFFAOYSA-N CCOC(C(C(C1=CC=CN=C11)=O)=CN1N(CC1C2)CC12NC(C(F)(F)F)=O)=O Chemical compound CCOC(C(C(C1=CC=CN=C11)=O)=CN1N(CC1C2)CC12NC(C(F)(F)F)=O)=O VXJRQGHURCVYIS-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CCTVTQAWAVQOAI-UHFFFAOYSA-N N-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-yl)-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NC1CCC2CNCC12 CCTVTQAWAVQOAI-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- RWCZOVMOKFTUAD-UHFFFAOYSA-N ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 RWCZOVMOKFTUAD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- SDAXRHHPNYTELL-UHFFFAOYSA-N heptanenitrile Chemical compound CCCCCCC#N SDAXRHHPNYTELL-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ZAGPJDOOZKONIH-UHFFFAOYSA-N methyl N-(3-benzyl-3-azabicyclo[3.1.0]hexan-1-yl)carbamate Chemical compound COC(=O)NC12CC1CN(C2)CC3=CC=CC=C3 ZAGPJDOOZKONIH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、優れた抗菌活性を有す
るピリドンカルボン酸誘導体の価値ある中間体たる新規
なビシクロアミン誘導体およびその塩に関する。TECHNICAL FIELD The present invention relates to a novel bicycloamine derivative which is a valuable intermediate of a pyridonecarboxylic acid derivative having excellent antibacterial activity and a salt thereof.
【０００２】[0002]
【従来の技術】特開昭59−67269 号公報および特開昭60
−214773号公報には、７位にジアザビシクロ環を有する
ピリドンカルボン酸誘導体が記載されているが、そこに
は本発明化合物は具体的には開示されていない。2. Description of the Related Art JP-A-59-67269 and JP-A-60
No. 214773 discloses a pyridonecarboxylic acid derivative having a diazabicyclo ring at the 7-position, but the compound of the present invention is not specifically disclosed therein.
【０００３】[0003]
【発明の目的】本発明は、優れた抗菌作用を有するピリ
ドンカルボン酸誘導体の中間体として有用な新規ビシク
ロアミン誘導体を提供するものである。OBJECT OF THE INVENTION The present invention provides a novel bicycloamine derivative useful as an intermediate of a pyridonecarboxylic acid derivative having an excellent antibacterial action.
【０００４】[0004]
【発明の構成】本発明化合物は、下記一般式〔Ｉ〕The compound of the present invention has the following general formula [I]:
【０００５】[0005]
【化２】 （式中、Ｒは水素原子，低級アルキルオキシカルボニル
基またはハロゲン原子で置換されていてもよい低級アシ
ル基を意味し、ｍは０または２を意味し、ｎは０または
１を意味する。）で表されるビシクロアミン誘導体およ
びその塩である。[Chemical 2] (In the formula, R represents a hydrogen atom, a lower alkyloxycarbonyl group or a lower acyl group optionally substituted by a halogen atom, m represents 0 or 2, and n represents 0 or 1.) Is a bicycloamine derivative and a salt thereof.
【０００６】本明細書において、ハロゲン原子として
は、フッ素，塩素等が挙げられる。低級アルキルオキシ
カルボニル基における低級アルキルとしては、例えばメ
チル，エチル，プロピル，イソプロピル，ブチル，イソ
ブチル，ｔ−ブチル，ペンチル，ネオペンチル等が挙げ
られる。置換していてもよい低級アシル基としては、ア
セチル，トリフルオロアセチル等が挙げられる。In the present specification, examples of the halogen atom include fluorine and chlorine. Examples of the lower alkyl in the lower alkyloxycarbonyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, neopentyl and the like. Examples of the lower acyl group which may be substituted include acetyl and trifluoroacetyl.
【０００７】本発明化合物の塩としては、塩酸，リン
酸，硫酸等の無機酸との塩；酢酸，乳酸，シュウ酸，コ
ハク酸，メタンスルホン酸，マレイン酸、マロン酸，グ
ルコン酸等の有機酸との塩が挙げられる。The salts of the compound of the present invention include salts with inorganic acids such as hydrochloric acid, phosphoric acid and sulfuric acid; organic acids such as acetic acid, lactic acid, oxalic acid, succinic acid, methanesulfonic acid, maleic acid, malonic acid and gluconic acid. The salt with an acid is mentioned.
【０００８】更に本発明化合物には、不斉炭素原子を有
するものが含まれ、それらは光学活性体として存在し得
る。これらの光学活性体も本発明化合物に包含される。
更にまた、本発明化合物の中には、複数個の不斉炭素原
子を有するものがあり、それらは異なる立体異性体とし
て存在し得る。これらの立体異性体もまた本発明化合物
に包含される。Further, the compounds of the present invention include those having an asymmetric carbon atom, which may exist as an optically active substance. These optically active compounds are also included in the compound of the present invention.
Furthermore, some compounds of the present invention have multiple asymmetric carbon atoms which may exist as different stereoisomers. These stereoisomers are also included in the compound of the present invention.
【０００９】次に本発明化合物の製造法について説明す
る。本発明化合物は、下記一般式Next, a method for producing the compound of the present invention will be described. The compound of the present invention has the following general formula:
【００１０】[0010]
【化３】 （Ｚは還元的に脱離し得る保護基を意味し、Ｒ，ｍおよ
びｎは前掲に同じ。）で表わされる式〔II〕の化合物を
還元し、該保護基を除去することにより製造することが
できる。[Chemical 3] (Z means a reductively removable protecting group, R, m and n are the same as those mentioned above.) The compound of the formula [II] is reduced and the protecting group is removed. You can
【００１１】本反応は、原料化合物〔II〕を溶媒中触媒
の存在下に０〜８０℃で３０分〜２４時間接触還元する
ことにより実施できる。保護基としては、反応によって
形成される本発明の化合物の構造を破壊することなく還
元的に除去しうるものであれば如何なるものでもよく、
ペプチドあるいはアミノ糖または核酸もしくはβ−ラク
タム系化合物の化学の分野で保護基として通常用いられ
ている保護基が使用される。好ましい保護基としては、
例えばベンジル基あるいはベンジルオキシカルボニル基
等が挙げられる。触媒としては、例えばパラジウム−炭
素，ラネーニッケル，酸化白金等が挙げられる。溶媒
は、原料化合物や使用する触媒により適宜選択すればよ
いが、エーテル，テトラヒドロフラン，トルエン，メタ
ノール，エタノール，酢酸，アンモニア，水等が使用さ
れる。This reaction can be carried out by catalytically reducing the starting compound [II] in a solvent in the presence of a catalyst at 0 to 80 ° C. for 30 minutes to 24 hours. The protecting group may be any as long as it can be reductively removed without destroying the structure of the compound of the present invention formed by the reaction,
A protecting group usually used as a protecting group in the field of chemistry of peptide or amino sugar or nucleic acid or β-lactam compound is used. As a preferable protecting group,
Examples thereof include a benzyl group and a benzyloxycarbonyl group. Examples of the catalyst include palladium-carbon, Raney nickel, platinum oxide and the like. The solvent may be appropriately selected depending on the raw material compound and the catalyst used, but ether, tetrahydrofuran, toluene, methanol, ethanol, acetic acid, ammonia, water or the like is used.
【００１２】本発明化合物の立体異性体は通常の方法、
例えば分別結晶，クロマトグラフィ分離等により、互い
に分離することができる。本発明化合物の光学活性体も
また、公知の方法を適用することによって、分離するこ
とが可能である。The stereoisomer of the compound of the present invention can be obtained by a conventional method,
They can be separated from each other by, for example, fractional crystallization and chromatographic separation. The optically active substance of the compound of the present invention can also be separated by applying a known method.
【００１３】なお、原料化合物〔II〕は後記実施例記載
の方法により製造できる。例えば、ｍが２である原料化
合物〔II〕は、Ｎ−ベンジルグリシン，２−シクロペン
テン−１−オンおよびパラホルムアルデヒドから誘導さ
れた３−ベンジル−３−アザビシクロ〔３．３．０〕オ
クタン−６−オンを後記実施例１の記載に従って処理す
ることにより製造できるし、ｍが０である原料化合物
〔II〕は、TetrahedronLetters, 369(1975)に記載され
ている３−ベンジル−３−アザビシクロ〔３．１．０〕
ヘキサン−１−カルボニトリルを出発物質とし、後記実
施例２または３の記載に従って処理することにより製造
できる。The starting compound [II] can be produced by the method described in Examples below. For example, the starting compound [II] in which m is 2 is 3-benzyl-3-azabicyclo [3.3.0] octane-6 derived from N-benzylglycine, 2-cyclopenten-1-one and paraformaldehyde. -One can be prepared by treating it as described in Example 1 below, and the starting compound [II] in which m is 0 is 3-benzyl-3-azabicyclo [3] described in Tetrahedron Letters, 369 (1975). .1.0]
It can be produced by using hexane-1-carbonitrile as a starting material and treating as described in Example 2 or 3 below.
【００１４】かくして得られる本発明化合物〔Ｉ〕はい
ずれも新規化合物であり、優れた抗菌活性を有するピリ
ドンカルボン酸誘導体の製造中間体として価値あるもの
である。The compounds [I] of the present invention thus obtained are all novel compounds and are valuable as intermediates for the production of pyridonecarboxylic acid derivatives having excellent antibacterial activity.
【００１５】このような抗菌剤として有用なピリドンカ
ルボン酸誘導体は、例えば後記参考例に示すように本発
明化合物〔Ｉ〕と以下に示される公知のピリドンカルボ
ン酸とを、常法に従って反応せしめることにより製造さ
れる。The pyridonecarboxylic acid derivative useful as such an antibacterial agent is obtained by reacting the compound [I] of the present invention with a known pyridonecarboxylic acid shown below, for example, as shown in the following Reference Examples according to a conventional method. Manufactured by.
【００１６】[0016]
【化４】 [Chemical 4]
【００１７】次にこのようなピリドンカルボン酸誘導体
の抗菌データを表に示す。The antibacterial data of such pyridonecarboxylic acid derivatives are shown in the table below.
【００１８】[0018]
【表１】 [Table 1]
【００１９】*1：最小発育阻止濃度（ＭＩＣ：μｇ／m
l）はChemotherapy, 29(1),76(1981)に記載の方法に準
じて測定し、その結果を上記表中に示した。 * 1 : Minimum inhibitory concentration (MIC: μg / m
l) was measured according to the method described in Chemotherapy, 29 (1), 76 (1981), and the results are shown in the above table.
【００２０】[0020]
【実施例】次に実施例を挙げて本発明化合物の製造法を
更に具体的に説明する。EXAMPLES Next, the production method of the compound of the present invention will be explained more specifically with reference to examples.
【００２１】実施例 １−− ６−トリフルオロアセチルアミノ−３−アザビシクロ
〔３．３．０〕オクタン： Example 1--6-Trifluoroacetylamino-3-azabicyclo [3.3.0] octane:
【００２２】(1) Ｎ−ベンジルグリシン５ｇ，２−シ
クロペンテン−１−オン５ml，パラホルムアルデヒド
1.8ｇ，１，２−ジクロロエタン，およびｎ−ヘキサン
の混合物を脱水しながら５時間加熱還流して、３−ベン
ジル−３−アザビシクロ〔３．３．０〕オクタン−６−
オン 3.4ｇを油状物として得た。(1) N-benzylglycine 5 g, 2-cyclopenten-1-one 5 ml, paraformaldehyde
A mixture of 1.8 g, 1,2-dichloroethane, and n-hexane was heated under reflux for 5 hours while dehydrating, and 3-benzyl-3-azabicyclo [3.3.0] octane-6-
3.4 g of on was obtained as an oil.
【００２３】(2) この化合物 3.4ｇを20％苛性ソーダ
水溶液６mlの存在下に、エタノール中でヒドロキシルア
ミン塩酸塩 2.0ｇと反応させて、３−ベンジル−３−ア
ザビシクロ〔３．３．０〕オクタン−６−オンオキシム
1.7ｇを得た。 ＩＲスペクトル（液膜）cm-1：3300，1450，1050． マス・スペクトルｍ／ｚ：230(Ｍ+ ），213, 91.(2) 3.4 g of this compound was reacted with 2.0 g of hydroxylamine hydrochloride in ethanol in the presence of 6 ml of 20% aqueous sodium hydroxide solution to give 3-benzyl-3-azabicyclo [3.3.0] octane. -6-one oxime
1.7 g was obtained. IR spectrum (liquid film) cm −1 : 3300, 1450, 1050. Mass spectrum m / z: 230 (M + ), 213, 91.
【００２４】(3) この化合物 1.7ｇを11％アンモニア
−エタノール溶液70mlに溶かし、ラネーニッケル５mlを
触媒として50℃で接触還元を行った。触媒を濾去し、濾
液を減圧で濃縮した。残渣をクロロホルムに溶かし、氷
冷下に無水トリフルオロ酢酸５mlと40分間反応させた
後、カラムクロマトグラフィで分離精製して、次の化合
物を無色油状物として得た。(3) 1.7 g of this compound was dissolved in 70 ml of an 11% ammonia-ethanol solution, and catalytic reduction was carried out at 50 ° C. using 5 ml of Raney nickel as a catalyst. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, reacted with 5 ml of trifluoroacetic anhydride under ice cooling for 40 minutes, and then separated and purified by column chromatography to obtain the following compound as a colorless oil.
【００２５】化合物Ａ：５，６−シス−３−ベンジル−
６−トリフルオロアセチルアミノ−３−アザビシクロ
〔３．３．０〕オクタン（0.5 ｇ）． ＩＲスペクトル（液膜）cm-1：3220，1715，1205，117
5，1150． マス・スペクトルｍ／ｚ：312(Ｍ+ ），235, 221, 91. ＮＭＲスペクトル（ＣＤＣｌ3 ）δ：4.26（１Ｈ，ｍ，
Ｃ6−Ｈ）Compound A: 5,6-cis-3-benzyl-
6-Trifluoroacetylamino-3-azabicyclo [3.3.0] octane (0.5 g). IR spectrum (liquid film) cm −1 : 3220, 1715, 1205, 117
5, 1150. Mass spectrum m / z: 312 (M + ), 235, 221, 91. NMR spectrum (CDCl 3 ) δ: 4.26 (1H, m,
C 6 -H)
【００２６】化合物Ｂ：５，６−トランス−３−ベンジ
ル−６−トリフルオロアセチルアミノ−３−アザビシク
ロ〔３．３．０〕オクタン（0.4 ｇ）． ＩＲスペクトル（液膜）cm-1：3300，1700，1550，121
0，1185，1160． マス・スペクトルｍ／ｚ：312(Ｍ+ ），235, 221, 91. ＮＭＲスペクトル（ＣＤＣｌ3 ）δ：4.06（１Ｈ，ｍ，
Ｃ6−Ｈ）Compound B: 5,6-trans-3-benzyl-6-trifluoroacetylamino-3-azabicyclo [3.3.0] octane (0.4 g). IR spectrum (liquid film) cm -1 : 3300, 1700, 1550, 121
0, 1185, 1160. Mass spectrum m / z: 312 (M + ), 235, 221, 91. NMR spectrum (CDCl 3 ) δ: 4.06 (1H, m,
C 6 -H)
【００２７】(4) 上記化合物Ａをエタノールに溶か
し、パラジウム−炭素を触媒として接触還元して、目的
物（シス体）を得た。同様にして、上記化合物Ｂから目
的物（トランス体）を得た。(4) The above compound A was dissolved in ethanol and catalytically reduced using palladium-carbon as a catalyst to obtain the desired product (cis form). Similarly, the target compound (trans form) was obtained from the compound B.
【００２８】実施例 ２−− １−メトキシカルボニルアミノ−３−アザビシクロ
〔３．１．０〕ヘキサン： Example 2--1-methoxycarbonylamino-3-azabicyclo [3.1.0] hexane:
【００２９】(1) 公知化合物３−ベンジル−３−アザ
ビシクロ〔３．１．０〕ヘキサン−１−カルボニトリル
〔Tetrahedron Letters, 368(1975)〕 2.0ｇと濃硫酸を
室温で５時間攪拌して、３−ベンジル−３−アザビシク
ロ〔３．１．０〕ヘキサン−１−カルボキサミド 1.6ｇ
を得た。 m.p.62〜63℃.(1) 2.0 g of the known compound 3-benzyl-3-azabicyclo [3.1.0] hexane-1-carbonitrile [Tetrahedron Letters, 368 (1975)] and concentrated sulfuric acid were stirred at room temperature for 5 hours. , 3-benzyl-3-azabicyclo [3.1.0] hexane-1-carboxamide 1.6 g
Got mp62 ~ 63 ℃.
【００３０】(2) この化合物 1.5ｇをメタノールに溶
かし、アンチホルミンで処理して、３−ベンジル−１−
メトキシカルボニルアミノ−３−アザビシクロ〔３．
１．０〕ヘキサン 0.7ｇを得た。 m.p. 102〜104 ℃. (3) この化合物を実施例１(4) と同様に処理して目的
物を得た。(2) 1.5 g of this compound was dissolved in methanol and treated with antiformin to give 3-benzyl-1-
Methoxycarbonylamino-3-azabicyclo [3.
1.0] Hexane 0.7 g was obtained. mp 102-104 ° C. (3) This compound was treated in the same manner as in Example 1 (4) to obtain the desired product.
【００３１】実施例 ３−− １−トリフルオロアセチルアミノメチル−３−アザビシ
クロ〔３．１．０〕ヘキサン： Example 3--1-Trifluoroacetylaminomethyl-3-azabicyclo [3.1.0] hexane:
【００３２】(1) 公知化合物３−ベンジル−３−アザ
ビシクロ〔３．１．０〕ヘキサン−１−カルボニトリル
を、実施例１(3) と同様に処理して、３−ベンジル−１
−トリフルオロアセチルアミノメチル−３−アザビシク
ロ〔３．１．０〕ヘキサンを得た。 (2) この化合物を実施例１(4) と同様に処理して目的
物を得た。(1) The known compound 3-benzyl-3-azabicyclo [3.1.0] hexane-1-carbonitrile was treated in the same manner as in Example 1 (3) to give 3-benzyl-1.
-Trifluoroacetylaminomethyl-3-azabicyclo [3.1.0] hexane was obtained. (2) This compound was treated in the same manner as in Example 1 (4) to obtain the desired product.
【００３３】参考例 １−− １−シクロプロピル−６，８−ジフルオロ−７−（５，
６−シス−６−アミノ−３−アザビシクロ〔３．３．
０〕オクタン−３−イル）−１，４−ジヒドロ−４−オ
キソキノリン−３−カルボン酸： Reference Example 1--1-cyclopropyl-6,8-difluoro-7- (5
6-cis-6-amino-3-azabicyclo [3.3.
0] octane-3-yl) -1,4-dihydro-4-oxoquinoline-3-carboxylic acid:
【００３４】(1) ５，６−シス−３−ベンジル−６−
トリフルオロアセチルアミノ−３−アザビシクロ〔３．
３．０〕オクタン 640mgをエタノール10mlに溶かし、５
％パラジウム−炭素 100mgを加えて水素雰囲気下60℃で
攪拌した。理論量の水素を吸収させた後、触媒を濾去
し、濾液を濃縮して、５，６−シス−６−トリフルオロ
アセチルアミノ−３−アザビシクロ〔３．３．０〕オク
タンを得た。これをアセトニトリル10mlに溶かし、トリ
エチルアミン 0.3mlおよび１−シクロプロピル−６，
７，８−トリフルオロ−１，４−ジヒドロ−４−オキソ
キノリン−３−カルボン酸 400mgを加えて、120 〜140
℃で 1.5 時間加熱還流した。氷冷後析出する結晶を濾
取し、水，エタノールおよびエーテルで洗浄して、１−
シクロプロピル−６，８−ジフルオロ−７−（５，６−
シス−６−トリフルオロアセチルアミノ−３−アザビシ
クロ〔３．３．０〕オクタン−３−イル）−１，４−シ
ヒドロ−４−オキソキノリン−３−カルボン酸0.42ｇを
淡黄色結晶として得た。 m.p.245 〜247 ℃．(1) 5,6-cis-3-benzyl-6-
Trifluoroacetylamino-3-azabicyclo [3.
3.0] Dissolve 640 mg of octane in 10 ml of ethanol, and
% Palladium-carbon (100 mg) was added, and the mixture was stirred at 60 ° C under a hydrogen atmosphere. After absorbing a theoretical amount of hydrogen, the catalyst was filtered off and the filtrate was concentrated to give 5,6-cis-6-trifluoroacetylamino-3-azabicyclo [3.3.0] octane. This was dissolved in 10 ml of acetonitrile, 0.3 ml of triethylamine and 1-cyclopropyl-6,
400 mg of 7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid was added to give 120-140
The mixture was heated at reflux at 1.5 ° C for 1.5 hours. The crystals precipitated after cooling with ice were collected by filtration, washed with water, ethanol and ether to give 1-
Cyclopropyl-6,8-difluoro-7- (5,6-
0.42 g of cis-6-trifluoroacetylamino-3-azabicyclo [3.3.0] octane-3-yl) -1,4-sihydro-4-oxoquinoline-3-carboxylic acid was obtained as pale yellow crystals. . mp245-247 ° C.
【００３５】(2) この化合物0.35ｇに５％苛性ソーダ
水溶液２mlを加え、100 ℃で２時間加熱した。冷後反応
液を酢酸で酸性とし、次いで濃アンモニア水を加えてア
ルカリ性とした。減圧で約半量まで濃縮し、室温で一夜
放置した。析出する結晶を濾取し、水，エタノール，エ
ーテルで順次洗浄して、目的物0.18ｇを白色粉末として
得た。 m.p. 240〜244 ℃（分解）.(2) To 0.35 g of this compound was added 2 ml of a 5% aqueous sodium hydroxide solution, and the mixture was heated at 100 ° C. for 2 hours. After cooling, the reaction solution was acidified with acetic acid, and then concentrated aqueous ammonia was added to make the solution alkaline. The mixture was concentrated under reduced pressure to about half volume and left at room temperature overnight. The precipitated crystals were collected by filtration and washed successively with water, ethanol and ether to give the desired product (0.18 g) as a white powder. mp 240-244 ° C (decomposition).
【００３６】参考例 ２−− １−シクロプロピル−６，８−ジフルオロ−７−（５，
６−トランス−６−アミノ−３−アザビシクロ〔３．
３．０〕オクタン−３−イル）−１，４−ジヒドロ−４
−オキソキノリン−３−カルボン酸： Reference Example 2--1-cyclopropyl-6,8-difluoro-7- (5
6-trans-6-amino-3-azabicyclo [3.
3.0] Octane-3-yl) -1,4-dihydro-4
-Oxoquinoline-3-carboxylic acid:
【００３７】(1) ５，６−トランス−３−ベンジル−
６−トリフルオロアセチルアミノ−３−アザビシクロ
〔３．３．０〕オクタンを用いることにより、参考例１
(1) と同様にして、１−シクロプロピル−６，８−ジフ
ルオロ−７−（５，６−トランス−６−トリフルオロア
セチルアミノ−３−アザビシクロ〔３．３．０〕オクタ
ン−３−イル）−１，４−ジヒドロ−４−オキソキノリ
ン−３−カルボン酸を得た。 m.p. 217〜221 ℃. (2) この化合物をを参考例１(2) と同様に処理して目
的物を得た。(1) 5,6-trans-3-benzyl-
By using 6-trifluoroacetylamino-3-azabicyclo [3.3.0] octane, Reference Example 1
In the same manner as in (1), 1-cyclopropyl-6,8-difluoro-7- (5,6-trans-6-trifluoroacetylamino-3-azabicyclo [3.3.0] octane-3-yl ) -1,4-Dihydro-4-oxoquinoline-3-carboxylic acid was obtained. mp 217-221 ° C. (2) This compound was treated in the same manner as in Reference Example 1 (2) to obtain the desired product.
【００３８】参考例 ３−− ７−（１−アミノ−３−アザビシクロ〔３．１．０〕ヘ
キサン−３−イル）−１−シクロプロピル−６，８−ジ
フルオロ−１，４−ジヒドロ−４−オキソキノリン−３
−カルボン酸： Reference Example 3--7- (1-Amino-3-azabicyclo [3.1.0] hexan-3-yl) -1-cyclopropyl-6,8-difluoro-1,4-dihydro-4 -Oxoquinoline-3
-Carboxylic acid:
【００３９】(1) ３−ベンジル−１−メトキシカルボ
ニルアミノ−３−アザビシクロ〔３．１．０〕ヘキサン
を用いることにより、参考例１(1) と同様にして１−シ
クロプロピル−６，８−ジフルオロ−７−（１−メトキ
シカルボニルアミノ−３−アザビシクロ〔３．１．０〕
ヘキサン−３−イル）−１，４−ジヒドロ−４−オキソ
キノリン−３−カルボン酸を得た。 m.p. 176〜178
℃. (2) この化合物を参考例１(2) と同様に処理して目的
物を得た。 m.p. 186〜188 ℃.(1) 1-Cyclopropyl-6,8 in the same manner as in Reference Example 1 (1) by using 3-benzyl-1-methoxycarbonylamino-3-azabicyclo [3.1.0] hexane. -Difluoro-7- (1-methoxycarbonylamino-3-azabicyclo [3.1.0]]
Hexan-3-yl) -1,4-dihydro-4-oxoquinoline-3-carboxylic acid was obtained. mp 176-178
C. (2) This compound was treated in the same manner as in Reference Example 1 (2) to obtain the desired product. mp 186-188 ° C.
【００４０】参考例 ４−− ７−（１−アミノメチル−３−アザビシクロ〔３．１．
０〕ヘキサン−３−イル）−１−シクロプロピル−６−
フルオロ−１，４−ジヒドロ−４−オキソ−１，８−ナ
フチリジン−３−カルボン酸： Reference Example 4--7- (1-Aminomethyl-3-azabicyclo [3.1.
0] hexan-3-yl) -1-cyclopropyl-6-
Fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid:
【００４１】(1) ３−ベンジル−１−トリフルオロア
セチルアミノメチル−３−アザビシクロ〔３．１．０〕
ヘキサンと、７−クロロ−１−シクロプロピル−６−フ
ルオロ−１，４−ジヒドロ−４−オキソ−１，８−ナフ
チリジン−３−カルボン酸エチルから、参考例１(1) と
同様にして １−シクロプロピル−６−フルオロ−７−
（１−トリフルオロアセチルアミノ−３−アザビシクロ
〔３．１．０〕ヘキサン−３−イル）−１，４−ジヒド
ロ−４−オキソ−１，８−ナフチリジン−３−カルボン
酸エチルを得た。 m.p. 234〜235 ℃. (2) この化合物をを参考例１(2) と同様に処理して目
的物を得た。 m.p. 245〜250 ℃（分解）．(1) 3-benzyl-1-trifluoroacetylaminomethyl-3-azabicyclo [3.1.0]
From hexane and ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, in the same manner as in Reference Example 1 (1): -Cyclopropyl-6-fluoro-7-
There was obtained ethyl (1-trifluoroacetylamino-3-azabicyclo [3.1.0] hexan-3-yl) -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate. mp 234-235 ° C. (2) This compound was treated in the same manner as in Reference Example 1 (2) to obtain the desired product. mp 245-250 ° C (decomposition).
【００４２】[0042]
【発明の効果】以上説明したように、本発明化合物であ
るビシクロアミン誘導体は、優れた抗菌力を有するピリ
ドンカルボン酸誘導体の直接の中間体として価値ある化
合物である。Industrial Applicability As described above, the compound of the present invention, the bicycloamine derivative, is a valuable compound as a direct intermediate of a pyridonecarboxylic acid derivative having excellent antibacterial activity.
Claims (6)
体およびその塩： 【化１】 （式中、Ｒは水素原子，低級アルキルオキシカルボニル
基またはハロゲン原子で置換されていてもよいアシル基
を意味し、ｍは０または２を意味し、ｎは０または１を
意味する。）1. A bicycloamine derivative represented by the following general formula and a salt thereof: (In the formula, R represents a hydrogen atom, a lower alkyloxycarbonyl group, or an acyl group optionally substituted with a halogen atom, m represents 0 or 2, and n represents 0 or 1.)
クロアミン誘導体およびその塩。2. The bicycloamine derivative and the salt thereof according to claim 1, wherein R is a hydrogen atom.
ある請求項１記載のビシクロアミン誘導体およびその
塩。 【請求項３】 Ｒがハロゲン原子で置換されていてもよ
いアシル基である請求項１記載のビシクロアミン誘導体
およびその塩。3. A bicycloamine derivative and a salt thereof according to claim 1, wherein R is a lower alkyloxycarbonyl group. 3. The bicycloamine derivative and salt thereof according to claim 1, wherein R is an acyl group which may be substituted with a halogen atom.
アザビシクロ〔３．３．０〕オクタンである請求項１記
載のビシクロアミン誘導体およびその塩。4. 6-Trifluoroacetylamino-3-
The bicycloamine derivative and salt thereof according to claim 1, which is azabicyclo [3.3.0] octane.
ザビシクロ〔３．１．０〕ヘキサンである請求項１記載
のビシクロアミン誘導体およびその塩。5. The bicycloamine derivative and a salt thereof according to claim 1, which is 1-methoxycarbonylamino-3-azabicyclo [3.1.0] hexane.
−３−アザビシクロ〔３．１．０〕ヘキサンである請求
項１記載のビシクロアミン誘導体およびその塩。6. The bicycloamine derivative and the salt thereof according to claim 1, which is 1-trifluoroacetylaminomethyl-3-azabicyclo [3.1.0] hexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6079850A JPH0780847B2 (en) | 1994-03-24 | 1994-03-24 | Bicycloamine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6079850A JPH0780847B2 (en) | 1994-03-24 | 1994-03-24 | Bicycloamine derivative |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62211808A Division JPH0676400B2 (en) | 1987-08-25 | 1987-08-25 | Novel pyridonecarboxylic acid derivative, its ester and its salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0748367A true JPH0748367A (en) | 1995-02-21 |
| JPH0780847B2 JPH0780847B2 (en) | 1995-08-30 |
Family
ID=13701680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6079850A Expired - Fee Related JPH0780847B2 (en) | 1994-03-24 | 1994-03-24 | Bicycloamine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0780847B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7868021B2 (en) | 1997-09-15 | 2011-01-11 | Warner Chilcott Company, Llc | Antimicrobial quinolones, their compositions and uses |
-
1994
- 1994-03-24 JP JP6079850A patent/JPH0780847B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7868021B2 (en) | 1997-09-15 | 2011-01-11 | Warner Chilcott Company, Llc | Antimicrobial quinolones, their compositions and uses |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0780847B2 (en) | 1995-08-30 |
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