JPH036143B2 - - Google Patents
Info
- Publication number
- JPH036143B2 JPH036143B2 JP3535282A JP3535282A JPH036143B2 JP H036143 B2 JPH036143 B2 JP H036143B2 JP 3535282 A JP3535282 A JP 3535282A JP 3535282 A JP3535282 A JP 3535282A JP H036143 B2 JPH036143 B2 JP H036143B2
- Authority
- JP
- Japan
- Prior art keywords
- yield
- mol
- irνcm
- cdcl
- nmr
- 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
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- -1 organic acid salts Chemical class 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 37
- 239000012230 colorless oil Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 238000000921 elemental analysis Methods 0.000 description 26
- 239000013078 crystal Substances 0.000 description 25
- 238000004519 manufacturing process Methods 0.000 description 21
- SPRIJFSYERPPCB-UHFFFAOYSA-N 2-hexylthiomorpholine Chemical compound CCCCCCC1CNCCS1 SPRIJFSYERPPCB-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 208000025865 Ulcer Diseases 0.000 description 9
- 231100000397 ulcer Toxicity 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 210000002784 stomach Anatomy 0.000 description 7
- XPBRQULQNAAEDL-UHFFFAOYSA-N 2-dodecylthiomorpholine Chemical compound CCCCCCCCCCCCC1CNCCS1 XPBRQULQNAAEDL-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HXZKGBRIQVZZII-UHFFFAOYSA-N 2-decylthiomorpholine Chemical compound CCCCCCCCCCC1CNCCS1 HXZKGBRIQVZZII-UHFFFAOYSA-N 0.000 description 4
- LGCYWCUWQBYGDP-UHFFFAOYSA-N 2-octylthiomorpholine Chemical compound CCCCCCCCC1CNCCS1 LGCYWCUWQBYGDP-UHFFFAOYSA-N 0.000 description 4
- SRCXETHSPBDKQD-UHFFFAOYSA-N 2-pentadecylthiomorpholine Chemical compound CCCCCCCCCCCCCCCC1CNCCS1 SRCXETHSPBDKQD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ANCSCGAGTWCCJY-UHFFFAOYSA-N 2-nonylthiomorpholine Chemical compound CCCCCCCCCC1CNCCS1 ANCSCGAGTWCCJY-UHFFFAOYSA-N 0.000 description 3
- PTOWQSPVNITXIN-UHFFFAOYSA-N 2-tridecylthiomorpholine Chemical compound CCCCCCCCCCCCCC1CNCCS1 PTOWQSPVNITXIN-UHFFFAOYSA-N 0.000 description 3
- SCPABRAAUUPLDH-UHFFFAOYSA-N 2-undecylthiomorpholine Chemical compound CCCCCCCCCCCC1CNCCS1 SCPABRAAUUPLDH-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000002467 anti-pepsin effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- UOTMYNBWXDUBNX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolin-2-ium;chloride Chemical group Cl.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 UOTMYNBWXDUBNX-UHFFFAOYSA-N 0.000 description 2
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 2
- IHAASKVYTDOONZ-UHFFFAOYSA-N 2-butylthiomorpholin-3-one Chemical compound CCCCC1SCCNC1=O IHAASKVYTDOONZ-UHFFFAOYSA-N 0.000 description 2
- RVRJFUUCVPPSGQ-UHFFFAOYSA-N 2-butylthiomorpholine Chemical compound CCCCC1CNCCS1 RVRJFUUCVPPSGQ-UHFFFAOYSA-N 0.000 description 2
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 2
- QKFCTAFQXHWNMT-UHFFFAOYSA-N 2-decylthiomorpholin-3-one Chemical compound CCCCCCCCCCC1SCCNC1=O QKFCTAFQXHWNMT-UHFFFAOYSA-N 0.000 description 2
- WUMYMILYRWEMEX-UHFFFAOYSA-N 2-heptadecylthiomorpholine Chemical compound CCCCCCCCCCCCCCCCCC1CNCCS1 WUMYMILYRWEMEX-UHFFFAOYSA-N 0.000 description 2
- JWSAVCBWTLHZAL-UHFFFAOYSA-N 2-heptylthiomorpholin-3-one Chemical compound CCCCCCCC1SCCNC1=O JWSAVCBWTLHZAL-UHFFFAOYSA-N 0.000 description 2
- TYPBSYYDJRIIML-UHFFFAOYSA-N 2-heptylthiomorpholine Chemical compound CCCCCCCC1CNCCS1 TYPBSYYDJRIIML-UHFFFAOYSA-N 0.000 description 2
- OCEOJMQRLOGSQI-UHFFFAOYSA-N 2-octylthiomorpholin-3-one Chemical compound CCCCCCCCC1SCCNC1=O OCEOJMQRLOGSQI-UHFFFAOYSA-N 0.000 description 2
- JEKVCZXRNRIODG-UHFFFAOYSA-N 2-tridecylthiomorpholin-3-one Chemical compound CCCCCCCCCCCCCC1SCCNC1=O JEKVCZXRNRIODG-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 230000004520 agglutination Effects 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 2
- 230000000762 glandular Effects 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- 229960003207 papaverine hydrochloride Drugs 0.000 description 2
- 208000011906 peptic ulcer disease Diseases 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- WYOGMVFABMEFBV-UHFFFAOYSA-N 2-dodecylthiomorpholin-3-one Chemical compound CCCCCCCCCCCCC1SCCNC1=O WYOGMVFABMEFBV-UHFFFAOYSA-N 0.000 description 1
- DDKAGKSWPJCQPN-UHFFFAOYSA-N 2-hexylthiomorpholin-3-one Chemical compound CCCCCCC1SCCNC1=O DDKAGKSWPJCQPN-UHFFFAOYSA-N 0.000 description 1
- YKZVQXSMNYXNKA-UHFFFAOYSA-N 2-nonylthiomorpholin-3-one Chemical compound CCCCCCCCCC1SCCNC1=O YKZVQXSMNYXNKA-UHFFFAOYSA-N 0.000 description 1
- YCBNKFXWQMRMES-UHFFFAOYSA-N 2-pentadecylthiomorpholin-3-one Chemical compound CCCCCCCCCCCCCCCC1SCCNC1=O YCBNKFXWQMRMES-UHFFFAOYSA-N 0.000 description 1
- UZLTUBYPNJANAM-UHFFFAOYSA-N 2-tetradecylthiomorpholin-3-one Chemical compound CCCCCCCCCCCCCCC1SCCNC1=O UZLTUBYPNJANAM-UHFFFAOYSA-N 0.000 description 1
- CDMMGYLNHIJELR-UHFFFAOYSA-N 2-undecylthiomorpholin-3-one Chemical compound CCCCCCCCCCCC1SCCNC1=O CDMMGYLNHIJELR-UHFFFAOYSA-N 0.000 description 1
- TVKYKXAPUMUAML-UHFFFAOYSA-N 4-dodecylthiomorpholine Chemical compound CCCCCCCCCCCCN1CCSCC1 TVKYKXAPUMUAML-UHFFFAOYSA-N 0.000 description 1
- YEQQTKZGAYOSGG-UHFFFAOYSA-N 4-hexylthiomorpholine Chemical compound CCCCCCN1CCSCC1 YEQQTKZGAYOSGG-UHFFFAOYSA-N 0.000 description 1
- XGNAIIIIJBIFFI-UHFFFAOYSA-N 4-nonylthiomorpholine Chemical compound CCCCCCCCCN1CCSCC1 XGNAIIIIJBIFFI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 239000000463 material Substances 0.000 description 1
- IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-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
- 238000002834 transmittance Methods 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 210000002417 xiphoid bone Anatomy 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3535282A JPS58152875A (ja) | 1982-03-06 | 1982-03-06 | ２−アルキル−４−（２−アミノエチル）チオモルホリン化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3535282A JPS58152875A (ja) | 1982-03-06 | 1982-03-06 | ２−アルキル−４−（２−アミノエチル）チオモルホリン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58152875A JPS58152875A (ja) | 1983-09-10 |
| JPH036143B2 true JPH036143B2 (enrdf_load_html_response) | 1991-01-29 |
Family
ID=12439467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3535282A Granted JPS58152875A (ja) | 1982-03-06 | 1982-03-06 | ２−アルキル−４−（２−アミノエチル）チオモルホリン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58152875A (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006137335A1 (ja) * | 2005-06-20 | 2006-12-28 | Otsuka Pharmaceutical Co., Ltd. | ピペラジン誘導体の製造方法 |
-
1982
- 1982-03-06 JP JP3535282A patent/JPS58152875A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58152875A (ja) | 1983-09-10 |
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