JPS6092300A - ソ−ヤサポゲノ−ルｂ誘導体の製法 - Google Patents
ソ−ヤサポゲノ−ルｂ誘導体の製法Info
- Publication number
- JPS6092300A JPS6092300A JP58201551A JP20155183A JPS6092300A JP S6092300 A JPS6092300 A JP S6092300A JP 58201551 A JP58201551 A JP 58201551A JP 20155183 A JP20155183 A JP 20155183A JP S6092300 A JPS6092300 A JP S6092300A
- Authority
- JP
- Japan
- Prior art keywords
- group
- soyasapogenol
- formula
- protecting group
- production
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 150000003402 soyasapogenol B derivatives Chemical class 0.000 title claims description 4
- 125000006239 protecting group Chemical group 0.000 claims abstract description 11
- URRZRRQMNMZIAP-UHFFFAOYSA-N Kudzusapogenol C Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)C(O)CC3(C)CCC21C URRZRRQMNMZIAP-UHFFFAOYSA-N 0.000 claims abstract description 10
- MADZMXIFUWFDJK-AEARDBQCSA-N soyasapogenol B Natural products CC1(C)C[C@@H](O)[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)C(=O)O)[C@](C)(CO)[C@@H]5CC[C@@]34C)[C@H]2C1 MADZMXIFUWFDJK-AEARDBQCSA-N 0.000 claims abstract description 9
- YOQAQNKGFOLRGT-UXXABWCISA-N (3beta,22beta)-olean-12-ene-3,22,24-triol Chemical compound C1C[C@H](O)[C@](C)(CO)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)[C@H](O)CC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C YOQAQNKGFOLRGT-UXXABWCISA-N 0.000 claims abstract description 8
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims abstract description 6
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229910001958 silver carbonate Inorganic materials 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- VNGUCOGHCJHFID-FLZFTVBESA-N Soyasapogenol C Chemical compound C([C@@]12C)C[C@H](O)[C@](C)(CO)[C@@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(C)(C)C=C[C@]3(C)CC[C@]21C VNGUCOGHCJHFID-FLZFTVBESA-N 0.000 claims 1
- 229930189104 soyasapogenol Natural products 0.000 claims 1
- 235000010469 Glycine max Nutrition 0.000 abstract description 7
- 244000068988 Glycine max Species 0.000 abstract description 7
- 239000000047 product Substances 0.000 abstract description 5
- 230000000295 complement effect Effects 0.000 abstract description 4
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical class OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 abstract description 3
- 235000015429 Mirabilis expansa Nutrition 0.000 abstract description 3
- 244000294411 Mirabilis expansa Species 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 235000013536 miso Nutrition 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 244000046052 Phaseolus vulgaris Species 0.000 abstract 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- GWTNLHGTLIBHHZ-SVNGYHJRSA-N methyl (2s,3s,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxane-2-carboxylate Chemical compound COC(=O)[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O GWTNLHGTLIBHHZ-SVNGYHJRSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- -1 p-bromophenacyl group Chemical group 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229930187719 Soyasaponin Natural products 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 239000012190 activator Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 239000012156 elution solvent Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- TXJTZIIDMZBTEB-UHFFFAOYSA-N (3alpha,11alpha)-3,11,23-Trihydroxy-20(29)-lupen-28-oic acid Natural products C1CC(O)C(C)(CO)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CC(O)C3C21C TXJTZIIDMZBTEB-UHFFFAOYSA-N 0.000 description 1
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229930185199 Sapogenol Natural products 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- AWSNMQUTBVZKHY-UHFFFAOYSA-N chloro-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)Cl AWSNMQUTBVZKHY-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000004332 silver Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000000915 soyasapogenol B group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 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
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58201551A JPS6092300A (ja) | 1983-10-26 | 1983-10-26 | ソ−ヤサポゲノ−ルｂ誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58201551A JPS6092300A (ja) | 1983-10-26 | 1983-10-26 | ソ−ヤサポゲノ−ルｂ誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6092300A true JPS6092300A (ja) | 1985-05-23 |
| JPH048437B2 JPH048437B2 (enrdf_load_stackoverflow) | 1992-02-17 |
Family
ID=16442921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58201551A Granted JPS6092300A (ja) | 1983-10-26 | 1983-10-26 | ソ−ヤサポゲノ−ルｂ誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6092300A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6137749A (ja) * | 1984-07-31 | 1986-02-22 | Otsuka Pharmaceut Co Ltd | トリテルペン誘導体 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170015259A (ko) * | 2015-07-31 | 2017-02-08 | 배남식 | 회전력 비교 시스템 그리고 회전력 비교 시스템 |
| KR20170015258A (ko) * | 2015-07-31 | 2017-02-08 | 배남식 | 동력 전달장치 |
Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5112513Y1 (enrdf_load_stackoverflow) * | 1967-10-28 | 1976-04-05 | ||
| JPS5365432A (en) * | 1976-11-19 | 1978-06-10 | Toray Industries | Yarn winder |
| DE2819366A1 (de) * | 1978-05-03 | 1979-11-15 | Voith Getriebe Kg | Lagerung fuer ein drehbares maschinenteil |
| JPS61273471A (ja) * | 1985-05-24 | 1986-12-03 | Mitsubishi Heavy Ind Ltd | 高速繊条巻取機 |
| JPS62211679A (ja) * | 1986-03-13 | 1987-09-17 | Toshiba Corp | 定着装置 |
| US4968624A (en) * | 1989-04-25 | 1990-11-06 | Baxter International Inc. | Large volume flexible containers |
| JPH03293262A (ja) * | 1990-04-06 | 1991-12-24 | Toray Ind Inc | 糸条の巻取装置 |
| JPH0568872U (ja) * | 1992-02-19 | 1993-09-17 | 凸版印刷株式会社 | バッグ・イン・ボックス用外箱 |
| JPH05256317A (ja) * | 1991-12-04 | 1993-10-05 | Carl Freudenberg:Fa | 軸受及びその製造方法 |
| JPH0711570U (ja) * | 1993-07-28 | 1995-02-21 | サンケミファ株式会社 | 簡易廃棄式液体容器 |
| JPH07277366A (ja) * | 1994-03-31 | 1995-10-24 | Sangyo Gijutsu Kenkyusho:Kk | 流動物の輸送方法 |
| JPH08175752A (ja) * | 1994-12-27 | 1996-07-09 | Toray Ind Inc | 糸条巻取機 |
| US6053449A (en) * | 1998-01-17 | 2000-04-25 | Barmag Ag | Yarn winding apparatus with spindle support |
| JP2003072842A (ja) * | 2001-08-27 | 2003-03-12 | Nisshin Oillio Ltd | 不定形物を収容する袋を入れる容器、該容器を作成するためのシート状部材および該容器の使用方法 |
| JP2003095249A (ja) * | 2001-09-20 | 2003-04-03 | Daiichi Radioisotope Labs Ltd | 梱包用段ボール箱 |
| JP2003285974A (ja) * | 2002-03-28 | 2003-10-07 | Tstm Co Ltd | コンタクトローラの支持方法 |
| JP2007111174A (ja) * | 2005-10-19 | 2007-05-10 | Yoshizawa:Kk | 液状飲食物用の加熱保温具 |
| JP2007522801A (ja) * | 2004-01-07 | 2007-08-16 | リーブテック，インコーポレイテッド | 一体のスパージャーとセンサー受け器を有する混合用袋 |
| JP2009030659A (ja) * | 2007-07-25 | 2009-02-12 | Asyst Technologies Japan Inc | ローラ装置 |
| JP2010126178A (ja) * | 2008-11-26 | 2010-06-10 | Kyoritsu Physical Distribution System Co Ltd | 液体もしくは粘体の排出用補助具及び排出方法 |
| JP2010222007A (ja) * | 2009-03-19 | 2010-10-07 | Rengo Co Ltd | 包装用胴枠 |
| WO2011012456A1 (de) * | 2009-07-30 | 2011-02-03 | Aktiebolaget Skf | Fest-los-lageranordnung |
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| JPS6137749A (ja) * | 1984-07-31 | 1986-02-22 | Otsuka Pharmaceut Co Ltd | トリテルペン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH048437B2 (enrdf_load_stackoverflow) | 1992-02-17 |
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