CA1262913A - Process for preparing a basic thioether and the salt thereof - Google Patents
Process for preparing a basic thioether and the salt thereofInfo
- Publication number
- CA1262913A CA1262913A CA000499391A CA499391A CA1262913A CA 1262913 A CA1262913 A CA 1262913A CA 000499391 A CA000499391 A CA 000499391A CA 499391 A CA499391 A CA 499391A CA 1262913 A CA1262913 A CA 1262913A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- furylmethylthio
- dimethylaminomethyl
- hydrochloride
- base
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 150000003839 salts Chemical class 0.000 title description 6
- 150000003568 thioethers Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 30
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 26
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 238000011065 in-situ storage Methods 0.000 claims abstract description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 32
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 235000013350 formula milk Nutrition 0.000 abstract description 58
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
- 230000001131 transforming effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229960000620 ranitidine Drugs 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ILRSPKULGBJLBZ-UHFFFAOYSA-N 2-nitroethenimine Chemical compound [O-][N+](=O)C=C=N ILRSPKULGBJLBZ-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZUKSLMGYYPZZJD-UHFFFAOYSA-N ethenimine Chemical compound C=C=N ZUKSLMGYYPZZJD-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 235000015250 liver sausages Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QURRWEMWCKISRF-UHFFFAOYSA-N 2-nitroethenone Chemical compound [O-][N+](=O)C=C=O QURRWEMWCKISRF-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000007836 Chlorogalum pomeridianum Nutrition 0.000 description 1
- 240000006670 Chlorogalum pomeridianum Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- -1 alipha-tic alcohols Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000009895 amole Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU85104A HU196979B (en) | 1985-01-11 | 1985-01-11 | Process for producing basic thioether and salt |
| HU104/85 | 1985-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1262913A true CA1262913A (en) | 1989-11-14 |
Family
ID=10947932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000499391A Expired CA1262913A (en) | 1985-01-11 | 1986-01-10 | Process for preparing a basic thioether and the salt thereof |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR920010926B1 (cs) |
| CN (1) | CN1005630B (cs) |
| AR (1) | AR242200A1 (cs) |
| AT (1) | AT391470B (cs) |
| CA (1) | CA1262913A (cs) |
| CS (1) | CS261232B2 (cs) |
| DK (1) | DK10486A (cs) |
| ES (1) | ES8703864A1 (cs) |
| FI (1) | FI90419C (cs) |
| GB (1) | GB2169600B (cs) |
| GR (1) | GR860058B (cs) |
| HU (1) | HU196979B (cs) |
| IT (1) | IT1203727B (cs) |
| NO (1) | NO170542C (cs) |
| PT (1) | PT81824B (cs) |
| SU (1) | SU1419519A3 (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU210849B (en) * | 1990-11-09 | 1995-08-28 | Richter Gedeon Vegyeszet | Process for preparing furil derivatives |
| HU207308B (en) * | 1990-11-09 | 1993-03-29 | Richter Gedeon Vegyeszet | Process for producing 1- /2-/5-/dimethyl-amino-methyl/-2-/furyl-methyl-thio/-ethyl//- -amino-1-/methyl-amino-2-nitro-ethylene |
| CN1048984C (zh) * | 1991-12-20 | 2000-02-02 | 多坎化学有限公司 | 晶形1呋喃硝胺氢氯化物的制备 |
| CN102010388B (zh) * | 2009-09-04 | 2012-09-05 | 江苏汉斯通药业有限公司 | 雷尼替丁的制备方法 |
| CN102010389B (zh) * | 2009-09-04 | 2012-11-14 | 江苏汉斯通药业有限公司 | 一种制备盐酸雷尼替丁的方法 |
| CN110590717B (zh) * | 2019-09-18 | 2022-08-26 | 上海大学 | 多取代烯酮亚胺及其合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| GB2014561B (en) * | 1977-12-23 | 1982-11-03 | Glaxo Group Ltd | Amine derivatives their preparation and pharmaceutical compositions containing them |
| US4203909A (en) * | 1978-09-26 | 1980-05-20 | Bristol-Myers Company | Furan compounds |
| ES497514A0 (es) * | 1980-12-05 | 1981-10-16 | Liade Sa Lab | Procedimiento de obtencion de un derivado de amina primaria heterociclica |
| EP0057981A3 (en) * | 1981-02-09 | 1982-08-25 | Beecham Group Plc | Aromatic compounds, processes for their preparation and their use |
| ES501845A0 (es) * | 1981-05-02 | 1982-11-01 | Especialidades Farmaco Terape | Procedimiento para la obtencion de un compuesto derivado delaminometilfurano |
| ES8206506A1 (es) * | 1981-11-16 | 1982-08-16 | Pharmedical Sa Lab | Procedimiento de preparacion de amino alcosi furanos o tio- fenos. |
| PT76557B (en) * | 1982-04-16 | 1986-01-21 | Inke Sa | Process for preparing furan derivatives and addition salts thereof and of pharmaceutical compositions containing the same |
-
1985
- 1985-01-11 HU HU85104A patent/HU196979B/hu not_active IP Right Cessation
-
1986
- 1986-01-10 ES ES550809A patent/ES8703864A1/es not_active Expired
- 1986-01-10 CN CN86100111.7A patent/CN1005630B/zh not_active Expired
- 1986-01-10 DK DK10486A patent/DK10486A/da not_active Application Discontinuation
- 1986-01-10 CA CA000499391A patent/CA1262913A/en not_active Expired
- 1986-01-10 KR KR1019860000116A patent/KR920010926B1/ko not_active Expired
- 1986-01-10 SU SU864009783A patent/SU1419519A3/ru active
- 1986-01-10 CS CS86230A patent/CS261232B2/cs unknown
- 1986-01-10 GB GB08600530A patent/GB2169600B/en not_active Expired
- 1986-01-10 GR GR860058A patent/GR860058B/el unknown
- 1986-01-10 PT PT81824A patent/PT81824B/pt not_active IP Right Cessation
- 1986-01-10 NO NO860071A patent/NO170542C/no unknown
- 1986-01-10 IT IT47517/86A patent/IT1203727B/it active
- 1986-01-10 FI FI860123A patent/FI90419C/fi not_active IP Right Cessation
- 1986-01-10 AR AR86302826A patent/AR242200A1/es active
- 1986-01-10 AT AT0003486A patent/AT391470B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN86100111A (zh) | 1986-11-26 |
| SU1419519A3 (ru) | 1988-08-23 |
| FI860123A7 (fi) | 1986-07-12 |
| NO170542C (no) | 1992-10-28 |
| GR860058B (en) | 1986-05-13 |
| IT1203727B (it) | 1989-02-23 |
| NO170542B (no) | 1992-07-20 |
| GB2169600B (en) | 1988-04-20 |
| PT81824A (en) | 1986-02-01 |
| ATA3486A (de) | 1990-04-15 |
| KR860005802A (ko) | 1986-08-13 |
| HU196979B (en) | 1989-02-28 |
| AR242200A1 (es) | 1993-03-31 |
| AT391470B (de) | 1990-10-10 |
| ES550809A0 (es) | 1987-03-01 |
| FI90419C (fi) | 1994-02-10 |
| DK10486A (da) | 1986-07-12 |
| GB2169600A (en) | 1986-07-16 |
| IT8647517A0 (it) | 1986-01-10 |
| PT81824B (pt) | 1987-11-30 |
| HUT38922A (en) | 1986-07-28 |
| CS261232B2 (en) | 1989-01-12 |
| CN1005630B (zh) | 1989-11-01 |
| ES8703864A1 (es) | 1987-03-01 |
| KR920010926B1 (ko) | 1992-12-24 |
| FI860123A0 (fi) | 1986-01-10 |
| NO860071L (no) | 1986-07-14 |
| FI90419B (fi) | 1993-10-29 |
| DK10486D0 (da) | 1986-01-10 |
| GB8600530D0 (en) | 1986-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |