JPH0468911B2 - - Google Patents
Info
- Publication number
- JPH0468911B2 JPH0468911B2 JP60084779A JP8477985A JPH0468911B2 JP H0468911 B2 JPH0468911 B2 JP H0468911B2 JP 60084779 A JP60084779 A JP 60084779A JP 8477985 A JP8477985 A JP 8477985A JP H0468911 B2 JPH0468911 B2 JP H0468911B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ether
- reaction
- lactam
- add
- 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 - Lifetime
Links
- 241000186000 Bifidobacterium Species 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 12
- 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 10
- 241000894006 Bacteria Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000003951 lactams Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ZAKWRGNVJHPXOW-UHFFFAOYSA-N 1-[3-(4-hydroxyphenyl)propanoyl]piperidin-2-one Chemical compound C1=CC(O)=CC=C1CCC(=O)N1C(=O)CCCC1 ZAKWRGNVJHPXOW-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 230000001902 propagating effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DCOVBLCOKIORBG-UHFFFAOYSA-N 1-[3-(4-phenylmethoxyphenyl)propanoyl]piperidin-2-one Chemical compound C1CCCC(=O)N1C(=O)CCC(C=C1)=CC=C1OCC1=CC=CC=C1 DCOVBLCOKIORBG-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical class OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000015140 cultured milk Nutrition 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 description 1
- 229960000511 lactulose Drugs 0.000 description 1
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- WCYAALZQFZMMOM-UHFFFAOYSA-N methanol;sulfuric acid Chemical compound OC.OS(O)(=O)=O WCYAALZQFZMMOM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Dairy Products (AREA)
- Confectionery (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60084779A JPS61242573A (ja) | 1985-04-19 | 1985-04-19 | ビフィドバクテリウム属細菌の増殖剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60084779A JPS61242573A (ja) | 1985-04-19 | 1985-04-19 | ビフィドバクテリウム属細菌の増殖剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61242573A JPS61242573A (ja) | 1986-10-28 |
| JPH0468911B2 true JPH0468911B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-04 |
Family
ID=13840172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60084779A Granted JPS61242573A (ja) | 1985-04-19 | 1985-04-19 | ビフィドバクテリウム属細菌の増殖剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61242573A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63270661A (ja) * | 1987-04-28 | 1988-11-08 | Taki Chem Co Ltd | １−〔２−（４−ヒドロキシベンゾイル）エタノイル〕−２−ピペリドン及びその製造法並びにそれを有効成分とするアルコ−ル発酵促進剤 |
| JPH11269142A (ja) * | 1998-03-18 | 1999-10-05 | Toa Yakuhin Kogyo Kk | アゼチジン誘導体、それを有効成分とするビフィズス菌分裂促進組成物およびその製造方法 |
-
1985
- 1985-04-19 JP JP60084779A patent/JPS61242573A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61242573A (ja) | 1986-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU988190A3 (ru) | Способ получени гидантоина | |
| US4522839A (en) | 3-Substituted 2,4,6-trihalogenated benzamides as sweetening agents | |
| EP0473308B1 (en) | Aldose reductase inhibitor | |
| JPS5933296A (ja) | ムラミルペプチド及びその製造方法 | |
| JPH0468911B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| WO1993002185A1 (en) | Acat inhibitor | |
| JP3933244B2 (ja) | アルキレンジアミン誘導体及び抗潰瘍剤、抗菌剤 | |
| JPS6239564A (ja) | α−ベンジリデン−γ−ブチロラクトンまたはγ−ブチロラクタム誘導体 | |
| JPH0898677A (ja) | ビフィズス菌増殖促進組成物 | |
| JPH0468910B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS6316118B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JP3265193B2 (ja) | ２−アミノ−３−カルボキシ−１，４−ナフトキノンの製造法 | |
| Tsou et al. | Preparation of alkyl 2-naphthyl carbonates as chromogenic substrates for esterases1 | |
| US2915532A (en) | Synthesis of 3, 5-dihydroxy-3 methylpentanoic acid and the delta-lactone thereof | |
| AU593084B2 (en) | A pharmaceutical formulation containing indomethacin | |
| TW408103B (en) | Guanidinomethyl hexane carboxylic acid ester derivatives | |
| US2891091A (en) | Derivatives of para-aminosalicylic acid | |
| EP0184853A2 (en) | Diarylhydroxy alkanones and alkanones antiallergy agents | |
| US3904670A (en) | Butacaine pamoate | |
| JPS6379586A (ja) | ビフイドバクテリウム属細菌の増殖剤 | |
| US2915531A (en) | Preparation of 3-methyl-3, 5-dihydroxypentanoic acid and the delta-lactone thereof | |
| GB1410275A (en) | Phenoxycarboxylic acid derivatives their preparation and compositions containing them | |
| JPH0228398B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JP2710052B2 (ja) | コードファクター関連化合物及びその製造法並びに該化合物を含有する免疫増強剤 | |
| DE2827657A1 (de) | Amino- oder guanidino-phenylpropionsaeurederivate, verfahren zu deren herstellung und arzneimittel |