JPS6134408B2 - - Google Patents

Info

Publication number: JPS6134408B2
Authority: JP; Japan
Prior art keywords: methyl; amino alcohol; pyrrolidine; ether; mmol
Prior art date: 1979-05-09
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

Application number

JP5652479A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55149250A (en

Inventor

Mitsuaki Mukoyama

Kenzo Ai

Toshio Sato

Keisuke Suzuki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Industries Ltd

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.)

1979-05-09

Filing date

1979-05-09

Publication date

1986-08-07

1979-05-09 Application filed by Mitsubishi Chemical Industries Ltd filed Critical Mitsubishi Chemical Industries Ltd

1979-05-09 Priority to JP5652479A priority Critical patent/JPS55149250A/ja

1980-11-20 Publication of JPS55149250A publication Critical patent/JPS55149250A/ja

1986-08-07 Publication of JPS6134408B2 publication Critical patent/JPS6134408B2/ja

Status Granted legal-status Critical Current

Links

150000001414 amino alcohols Chemical class 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
-1 2-(1-hydroxy--methylethyl)-1-[(1-methylpyrrolidin-2-yl) methyl]pyrrolidine Chemical compound 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
150000001728 carbonyl compounds Chemical class 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
230000029936 alkylation Effects 0.000 description 11
238000005804 alkylation reaction Methods 0.000 description 11
239000003446 ligand Substances 0.000 description 11
239000002168 alkylating agent Substances 0.000 description 10
229940100198 alkylating agent Drugs 0.000 description 10
239000002904 solvent Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910010082 LiAlH Inorganic materials 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
229910010084 LiAlH4 Inorganic materials 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
WQFNLMMCEOJFQE-UHFFFAOYSA-N [1-(pyrrolidin-2-ylmethyl)pyrrolidin-2-yl]methanol Chemical compound OCC1CCCN1CC1NCCC1 WQFNLMMCEOJFQE-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
150000003934 aromatic aldehydes Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
QEXAABUUPZABDJ-UHFFFAOYSA-N 1-ethyl-2-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound CCN1CCCC1CN1CCCC1 QEXAABUUPZABDJ-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical group CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
RTAQCQOZRWKSTQ-UHFFFAOYSA-N CC(C)C[Mg]CC(C)C Chemical compound CC(C)C[Mg]CC(C)C RTAQCQOZRWKSTQ-UHFFFAOYSA-N 0.000 description 1
SPXDYPYJHCSREL-UHFFFAOYSA-N CCC(C)[Mg]C(C)CC Chemical compound CCC(C)[Mg]C(C)CC SPXDYPYJHCSREL-UHFFFAOYSA-N 0.000 description 1
ABXKXVWOKXSBNR-UHFFFAOYSA-N CCC[Mg]CCC Chemical compound CCC[Mg]CCC ABXKXVWOKXSBNR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
VAUQXPBOGCJNHH-UHFFFAOYSA-N [1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidin-2-yl]methanol Chemical compound CN1CCCC1CN1C(CO)CCC1 VAUQXPBOGCJNHH-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
BMFYCFSWWDXEPB-UHFFFAOYSA-N cyclohexyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1 BMFYCFSWWDXEPB-UHFFFAOYSA-N 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
KZLUHGRPVSRSHI-UHFFFAOYSA-N dimethylmagnesium Chemical compound C[Mg]C KZLUHGRPVSRSHI-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 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
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
QBZXOWQOWPHHRA-UHFFFAOYSA-N lithium;ethane Chemical compound [Li+].[CH2-]C QBZXOWQOWPHHRA-UHFFFAOYSA-N 0.000 description 1
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
RVOYYLUVELMWJF-UHFFFAOYSA-N magnesium;hexane Chemical compound [Mg+2].CCCCC[CH2-].CCCCC[CH2-] RVOYYLUVELMWJF-UHFFFAOYSA-N 0.000 description 1
DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 description 1
UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical group [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
238000000034 method Methods 0.000 description 1
KALWJAOLQCJRJQ-HOTGVXAUSA-N methyl (2S)-1-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)OCC1=CC=CC=C1 KALWJAOLQCJRJQ-HOTGVXAUSA-N 0.000 description 1
BLWYXBNNBYXPPL-YFKPBYRVSA-N methyl (2s)-pyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1 BLWYXBNNBYXPPL-YFKPBYRVSA-N 0.000 description 1
HQEIPVHJHZTMDP-JEDNCBNOSA-N methyl (2s)-pyrrolidine-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)[C@@H]1CCCN1 HQEIPVHJHZTMDP-JEDNCBNOSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 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
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 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
150000005671 trienes Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)

JP5652479A 1979-05-09 1979-05-09 Aminoalcohol derivative Granted JPS55149250A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5652479A JPS55149250A (en)	1979-05-09	1979-05-09	Aminoalcohol derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5652479A JPS55149250A (en)	1979-05-09	1979-05-09	Aminoalcohol derivative

Publications (2)

Publication Number	Publication Date
JPS55149250A JPS55149250A (en)	1980-11-20
JPS6134408B2 true JPS6134408B2 (de)	1986-08-07

Family

ID=13029494

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5652479A Granted JPS55149250A (en)	1979-05-09	1979-05-09	Aminoalcohol derivative

Country Status (1)

Country	Link
JP (1)	JPS55149250A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01145514A (ja) *	1987-12-02	1989-06-07	Kobe Steel Ltd	炉内観察測距装置

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5221676A (en) *	1992-02-06	1993-06-22	Warner-Lambert Company	7-substituted quinolones and naphthyridones as antibacterial agents

1979
- 1979-05-09 JP JP5652479A patent/JPS55149250A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01145514A (ja) *	1987-12-02	1989-06-07	Kobe Steel Ltd	炉内観察測距装置

Also Published As

Publication number	Publication date
JPS55149250A (en)	1980-11-20

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JPS6134408B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=13029494

Family Applications (1)

Country Status (1)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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