DD238384A5 - Verfahren zur herstellung von neuen 2-pyridin-thiol-derivaten - Google Patents
Verfahren zur herstellung von neuen 2-pyridin-thiol-derivaten Download PDFInfo
- Publication number
- DD238384A5 DD238384A5 DD85281464A DD28146485A DD238384A5 DD 238384 A5 DD238384 A5 DD 238384A5 DD 85281464 A DD85281464 A DD 85281464A DD 28146485 A DD28146485 A DD 28146485A DD 238384 A5 DD238384 A5 DD 238384A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- pyridine
- carbon atoms
- meaning
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- -1 thiol compound Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- LVWFHYWRBSIXMC-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-phenylmethanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 LVWFHYWRBSIXMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 claims description 3
- ZBIDSILWMPPVTM-UHFFFAOYSA-N n-acetyl-n-[2-(3-benzoylpyridin-2-yl)sulfanylethyl]acetamide Chemical compound CC(=O)N(C(C)=O)CCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 ZBIDSILWMPPVTM-UHFFFAOYSA-N 0.000 claims description 3
- 150000005749 2-halopyridines Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 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 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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- KYYDUQIIPZUYPO-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=NC=CC=2)SCCN)=C1 KYYDUQIIPZUYPO-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CVIGZBUHEDENIJ-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(4-chlorophenyl)methanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=C(Cl)C=C1 CVIGZBUHEDENIJ-UHFFFAOYSA-N 0.000 description 3
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- 241000700157 Rattus norvegicus Species 0.000 description 2
- HPNCVUBDPCPUDK-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)-6-propylpyridin-4-yl]-phenylmethanone Chemical group NCCSC1=NC(CCC)=CC(C(=O)C=2C=CC=CC=2)=C1 HPNCVUBDPCPUDK-UHFFFAOYSA-N 0.000 description 2
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- OGLIEZKGUPAGHK-UHFFFAOYSA-N phenyl-(2-sulfanylidene-1h-pyridin-3-yl)methanone Chemical compound C=1C=CNC(=S)C=1C(=O)C1=CC=CC=C1 OGLIEZKGUPAGHK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD238384A5 true DD238384A5 (de) | 1986-08-20 |
Family
ID=10965437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85281464A DD238384A5 (de) | 1984-10-05 | 1985-10-04 | Verfahren zur herstellung von neuen 2-pyridin-thiol-derivaten |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4713388A (enExample) |
| EP (1) | EP0177907B1 (enExample) |
| JP (1) | JPS6191172A (enExample) |
| KR (1) | KR860003212A (enExample) |
| CN (1) | CN85107284A (enExample) |
| AT (1) | ATE34739T1 (enExample) |
| AU (1) | AU579665B2 (enExample) |
| DD (1) | DD238384A5 (enExample) |
| DE (1) | DE3563048D1 (enExample) |
| DK (1) | DK455285A (enExample) |
| ES (1) | ES8704460A1 (enExample) |
| FI (1) | FI853866A7 (enExample) |
| GR (1) | GR852409B (enExample) |
| HU (1) | HU192875B (enExample) |
| IL (1) | IL76577A0 (enExample) |
| IN (1) | IN162570B (enExample) |
| NO (1) | NO853935L (enExample) |
| PH (1) | PH21435A (enExample) |
| PL (1) | PL146371B1 (enExample) |
| PT (1) | PT81255B (enExample) |
| SU (1) | SU1346042A3 (enExample) |
| YU (1) | YU158385A (enExample) |
| ZA (1) | ZA857676B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1339423C (en) * | 1988-09-14 | 1997-09-02 | Yuji Ono | Pyridine compounds and pharmaceutical use thereof |
| DE69209576T4 (de) * | 1991-05-10 | 1997-01-30 | Takeda Chemical Industries Ltd | Pyridinderivate, deren Herstellung und Anwendung |
| JP4608140B2 (ja) * | 2000-07-05 | 2011-01-05 | 石原産業株式会社 | ベンゾイルピリジン誘導体またはその塩、それらを有効成分として含有する殺菌剤、それらの製造方法ならびにそれらを製造するための中間体 |
| AR029289A1 (es) | 2000-07-05 | 2003-06-18 | Ishihara Sangyo Kaisha | Derivado de benzoilpiridina o su sal, fungicida que lo contiene como un ingrediente activo, su proceso de produccion e intermediario para producirlo |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| JP4886511B2 (ja) | 2003-07-30 | 2012-02-29 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
| US7585883B2 (en) * | 2004-10-29 | 2009-09-08 | Rigel Pharmaceuticals, Inc. | Substituted pyridines and their uses |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT238200B (de) * | 1962-03-27 | 1965-01-25 | Degussa | Verfahren zur Herstellung von neuen Pyridinderivaten |
| JPS552920A (en) * | 1978-06-23 | 1980-01-10 | Natl Res Inst For Metals | Method of detecting surface dfect of non-magnetic material |
| US4304781A (en) * | 1978-11-30 | 1981-12-08 | John Wyeth & Brother Limited | Treatment of ulcers and hypertension |
| HU194830B (en) * | 1984-10-05 | 1988-03-28 | Richter Gedeon Vegyeszet | Process for the production of derivatives of piridine |
-
1984
- 1984-10-05 HU HU843775A patent/HU192875B/hu not_active IP Right Cessation
-
1985
- 1985-09-24 PH PH32832A patent/PH21435A/en unknown
- 1985-10-03 US US06/783,875 patent/US4713388A/en not_active Expired - Fee Related
- 1985-10-04 ES ES547604A patent/ES8704460A1/es not_active Expired
- 1985-10-04 AT AT85112599T patent/ATE34739T1/de not_active IP Right Cessation
- 1985-10-04 IN IN778/MAS/85A patent/IN162570B/en unknown
- 1985-10-04 PL PL1985255643A patent/PL146371B1/pl unknown
- 1985-10-04 SU SU853959903A patent/SU1346042A3/ru active
- 1985-10-04 EP EP85112599A patent/EP0177907B1/de not_active Expired
- 1985-10-04 IL IL76577A patent/IL76577A0/xx unknown
- 1985-10-04 PT PT81255A patent/PT81255B/pt unknown
- 1985-10-04 ZA ZA857676A patent/ZA857676B/xx unknown
- 1985-10-04 YU YU01583/85A patent/YU158385A/xx unknown
- 1985-10-04 NO NO853935A patent/NO853935L/no unknown
- 1985-10-04 CN CN198585107284A patent/CN85107284A/zh active Pending
- 1985-10-04 DE DE8585112599T patent/DE3563048D1/de not_active Expired
- 1985-10-04 JP JP60221714A patent/JPS6191172A/ja active Pending
- 1985-10-04 GR GR852409A patent/GR852409B/el unknown
- 1985-10-04 AU AU48328/85A patent/AU579665B2/en not_active Expired - Fee Related
- 1985-10-04 DK DK455285A patent/DK455285A/da not_active Application Discontinuation
- 1985-10-04 DD DD85281464A patent/DD238384A5/de unknown
- 1985-10-04 FI FI853866A patent/FI853866A7/fi not_active Application Discontinuation
- 1985-10-05 KR KR1019850007352A patent/KR860003212A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE3563048D1 (en) | 1988-07-07 |
| KR860003212A (ko) | 1986-05-21 |
| ES547604A0 (es) | 1987-04-01 |
| ES8704460A1 (es) | 1987-04-01 |
| PT81255A (en) | 1985-11-01 |
| US4713388A (en) | 1987-12-15 |
| PT81255B (en) | 1987-03-23 |
| AU4832885A (en) | 1986-04-10 |
| ATE34739T1 (de) | 1988-06-15 |
| ZA857676B (en) | 1986-06-25 |
| PH21435A (en) | 1987-10-15 |
| DK455285A (da) | 1986-04-06 |
| EP0177907A1 (de) | 1986-04-16 |
| IL76577A0 (en) | 1986-02-28 |
| GR852409B (enExample) | 1986-02-04 |
| PL255643A1 (en) | 1987-01-12 |
| HUT38907A (en) | 1986-07-28 |
| NO853935L (no) | 1986-04-07 |
| FI853866L (fi) | 1986-04-06 |
| FI853866A0 (fi) | 1985-10-04 |
| AU579665B2 (en) | 1988-12-01 |
| DK455285D0 (da) | 1985-10-04 |
| SU1346042A3 (ru) | 1987-10-15 |
| PL146371B1 (en) | 1989-01-31 |
| FI853866A7 (fi) | 1986-04-06 |
| IN162570B (enExample) | 1988-06-11 |
| JPS6191172A (ja) | 1986-05-09 |
| HU192875B (en) | 1987-07-28 |
| YU158385A (en) | 1988-04-30 |
| CN85107284A (zh) | 1986-06-10 |
| EP0177907B1 (de) | 1988-06-01 |
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