JPS6121628B2 - - Google Patents
Info
- Publication number
- JPS6121628B2 JPS6121628B2 JP3991081A JP3991081A JPS6121628B2 JP S6121628 B2 JPS6121628 B2 JP S6121628B2 JP 3991081 A JP3991081 A JP 3991081A JP 3991081 A JP3991081 A JP 3991081A JP S6121628 B2 JPS6121628 B2 JP S6121628B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydroquinoline
- parts
- oxo
- fluoro
- bromo
- 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.)
- Expired
Links
- -1 phenyl-substituted amino group Chemical group 0.000 claims description 7
- JRAVZISMXMYFRP-UHFFFAOYSA-N N-(2,3-dihydro-1H-quinolin-4-ylidene)hydroxylamine Chemical class C1=CC=C2C(=NO)CCNC2=C1 JRAVZISMXMYFRP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- FTSMXKUXNFFCGG-UHFFFAOYSA-N 6-fluoro-2,3-dihydro-1h-quinolin-4-one Chemical compound N1CCC(=O)C2=CC(F)=CC=C21 FTSMXKUXNFFCGG-UHFFFAOYSA-N 0.000 description 6
- 208000004880 Polyuria Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002686 anti-diuretic effect Effects 0.000 description 4
- 230000003501 anti-edematous effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- XXGYFIOVPVNIOK-ZROIWOOFSA-N (4z)-6-bromo-4-hydroxyimino-n-methyl-2,3-dihydroquinoline-1-carboxamide Chemical compound BrC1=CC=C2N(C(=O)NC)CC\C(=N\O)C2=C1 XXGYFIOVPVNIOK-ZROIWOOFSA-N 0.000 description 2
- CNLSVGAHIXRIEE-UVTDQMKNSA-N (4z)-6-fluoro-4-hydroxyimino-n,n-dimethyl-2,3-dihydroquinoline-1-carboxamide Chemical compound FC1=CC=C2N(C(=O)N(C)C)CC\C(=N\O)C2=C1 CNLSVGAHIXRIEE-UVTDQMKNSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- MRQMMZRTPYMDPW-UHFFFAOYSA-N 3-(4-bromoanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=C(Br)C=C1 MRQMMZRTPYMDPW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- WAFBCQPOMZIGTJ-UHFFFAOYSA-N 6-bromo-2,3-dihydro-1h-quinolin-4-one Chemical compound N1CCC(=O)C2=CC(Br)=CC=C21 WAFBCQPOMZIGTJ-UHFFFAOYSA-N 0.000 description 2
- JZESBTRKWJANML-UHFFFAOYSA-N 6-bromo-4-oxo-2,3-dihydroquinoline-1-carbonyl chloride Chemical compound BrC1=CC=C2N(C(=O)Cl)CCC(=O)C2=C1 JZESBTRKWJANML-UHFFFAOYSA-N 0.000 description 2
- KCEKQJOLQHOQRE-UHFFFAOYSA-N 6-fluoro-4-hydroxyimino-2,3-dihydroquinoline-1-carbaldehyde Chemical compound C1=C(F)C=C2C(=NO)CCN(C=O)C2=C1 KCEKQJOLQHOQRE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 208000010643 digestive system disease Diseases 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 208000018685 gastrointestinal system disease Diseases 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YSEKTWYSDQTJBX-JLHYYAGUSA-N 1-[(4E)-6-bromo-4-hydroxyimino-2,3-dihydroquinolin-1-yl]ethanone Chemical compound CC(=O)N1CC\C(=N/O)c2cc(Br)ccc12 YSEKTWYSDQTJBX-JLHYYAGUSA-N 0.000 description 1
- FEGWEZYQHKCBKL-UVTDQMKNSA-N 1-[(4z)-6-fluoro-4-hydroxyimino-2,3-dihydroquinolin-1-yl]propan-1-one Chemical compound FC1=CC=C2N(C(=O)CC)CC\C(=N\O)C2=C1 FEGWEZYQHKCBKL-UVTDQMKNSA-N 0.000 description 1
- YUGVRNDMXFUNIP-UHFFFAOYSA-N 1-acetyl-6-bromo-2,3-dihydroquinolin-4-one Chemical compound BrC1=CC=C2N(C(=O)C)CCC(=O)C2=C1 YUGVRNDMXFUNIP-UHFFFAOYSA-N 0.000 description 1
- KRGMMKVSHXVQCM-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carbonyl chloride Chemical compound C1=CC=C2N(C(=O)Cl)CCCC2=C1 KRGMMKVSHXVQCM-UHFFFAOYSA-N 0.000 description 1
- JENOQAMUNLTFDK-UHFFFAOYSA-N 3-(4-fluoroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=C(F)C=C1 JENOQAMUNLTFDK-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- WIWOOQUJODRMTD-UHFFFAOYSA-N 6-bromo-n-methyl-4-oxo-2,3-dihydroquinoline-1-carboxamide Chemical compound BrC1=CC=C2N(C(=O)NC)CCC(=O)C2=C1 WIWOOQUJODRMTD-UHFFFAOYSA-N 0.000 description 1
- POBDZBIXGMRCDM-UHFFFAOYSA-N 6-fluoro-4-oxo-2,3-dihydroquinoline-1-carbaldehyde Chemical compound O=CN1CCC(=O)C2=CC(F)=CC=C21 POBDZBIXGMRCDM-UHFFFAOYSA-N 0.000 description 1
- JDDSAQQFCKTOJF-UHFFFAOYSA-N 6-fluoro-4-oxo-2,3-dihydroquinoline-1-carbonyl chloride Chemical compound ClC(=O)N1CCC(=O)C2=CC(F)=CC=C21 JDDSAQQFCKTOJF-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 238000011160 research Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3991081A JPS57154168A (en) | 1981-03-19 | 1981-03-19 | Novel 4-oximino-1,2,3,4-tetrahydroquinoline derivative |
| GB8120931A GB2092130B (en) | 1980-07-28 | 1981-07-07 | 4-oximino-1,2,3,4-tetrahydroquinoline derivatives |
| US06/281,243 US4421919A (en) | 1980-07-28 | 1981-07-07 | 4-Oximino-1,2,3,4-tetrahydroquinoline derivatives |
| FR8114436A FR2487346A1 (fr) | 1980-07-28 | 1981-07-24 | Derives de la 4-oximino-1,2,3,4-tetrahydroquinoleine, leur procede de preparation et leur application therapeutique |
| DE19813129718 DE3129718A1 (de) | 1980-07-28 | 1981-07-28 | 4-oximino-1,2,3,4-tetrahydrochinolinderivate und verfahren zu ihrer herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3991081A JPS57154168A (en) | 1981-03-19 | 1981-03-19 | Novel 4-oximino-1,2,3,4-tetrahydroquinoline derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57154168A JPS57154168A (en) | 1982-09-22 |
| JPS6121628B2 true JPS6121628B2 (enrdf_load_stackoverflow) | 1986-05-28 |
Family
ID=12566098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3991081A Granted JPS57154168A (en) | 1980-07-28 | 1981-03-19 | Novel 4-oximino-1,2,3,4-tetrahydroquinoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57154168A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4835546B2 (ja) * | 2007-08-24 | 2011-12-14 | 日本精機株式会社 | 表示装置 |
-
1981
- 1981-03-19 JP JP3991081A patent/JPS57154168A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57154168A (en) | 1982-09-22 |
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