CS255884B2 - Process for preparing derivatives of substituted 3-phenyliminothiazolidine - Google Patents
Process for preparing derivatives of substituted 3-phenyliminothiazolidine Download PDFInfo
- Publication number
- CS255884B2 CS255884B2 CS853049A CS304985A CS255884B2 CS 255884 B2 CS255884 B2 CS 255884B2 CS 853049 A CS853049 A CS 853049A CS 304985 A CS304985 A CS 304985A CS 255884 B2 CS255884 B2 CS 255884B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- amino
- pharmaceutically acceptable
- acid addition
- thiazolidine
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- -1 nitro, amino, hydroxy Chemical group 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 150000002540 isothiocyanates Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 150000003548 thiazolidines Chemical class 0.000 claims 1
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KMMOAXMICGWZKX-UHFFFAOYSA-N methyl 3-amino-4-(2-imino-1,3-thiazolidin-3-yl)benzoate;dihydrochloride Chemical compound Cl.Cl.NC1=CC(C(=O)OC)=CC=C1N1C(=N)SCC1 KMMOAXMICGWZKX-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960004453 trimethadione Drugs 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863927A CS255873B2 (cs) | 1984-04-25 | 1986-05-29 | Způsob výroby derivátů substituovaného 3~fenyliminothiazolidinu |
| CS863928A CS255874B2 (cs) | 1984-04-25 | 1986-05-29 | Způsob výroby derivátů substituovaného 3-fenyliminothiazolidinu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU841581A HU191408B (en) | 1984-04-25 | 1984-04-25 | Process for preparing new imino-thiazolidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS304985A2 CS304985A2 (en) | 1987-07-16 |
| CS255884B2 true CS255884B2 (en) | 1988-03-15 |
Family
ID=10955127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS853049A CS255884B2 (en) | 1984-04-25 | 1985-04-25 | Process for preparing derivatives of substituted 3-phenyliminothiazolidine |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4665083A (en]) |
| JP (1) | JPS6127974A (en]) |
| AT (1) | AT394555B (en]) |
| BE (1) | BE902249A (en]) |
| CA (1) | CA1246086A (en]) |
| CH (1) | CH664564A5 (en]) |
| CS (1) | CS255884B2 (en]) |
| DD (1) | DD231790A5 (en]) |
| DE (1) | DE3514843A1 (en]) |
| DK (1) | DK183585A (en]) |
| ES (3) | ES8608499A1 (en]) |
| FI (1) | FI82454C (en]) |
| FR (1) | FR2563519B1 (en]) |
| GB (1) | GB2159814B (en]) |
| GR (1) | GR851006B (en]) |
| HU (1) | HU191408B (en]) |
| IT (1) | IT1208532B (en]) |
| NL (1) | NL8501184A (en]) |
| NO (1) | NO164417C (en]) |
| PH (1) | PH20995A (en]) |
| PL (3) | PL145084B1 (en]) |
| PT (1) | PT80336B (en]) |
| SE (1) | SE464813B (en]) |
| SU (3) | SU1366058A3 (en]) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3442757A1 (de) * | 1984-11-23 | 1986-05-28 | Wella Ag, 6100 Darmstadt | Verwendung von 2-nitroanilinderivaten in haarfaerbemitteln und neue 2-nitroanilinderivate |
| US4867782A (en) * | 1988-07-01 | 1989-09-19 | Ici Americas Inc. | Novel herbicidal 2-sulfonyliminothiazolidines |
| US5266701A (en) * | 1988-07-01 | 1993-11-30 | Ici Americas Inc. | Process for production of 2-iminothiazolidines and oxazolidines |
| US5240918A (en) * | 1992-03-24 | 1993-08-31 | Egis Gyogyszergyar | 2-(substituted imino)-thiazolidines and process for the preparation thereof |
| US5463069A (en) * | 1992-12-04 | 1995-10-31 | Sumitomo Chemical Company, Limited | Process of producing 2-iminothiazoline derivatives and process of producing their intermediates |
| JP2009501775A (ja) * | 2005-07-21 | 2009-01-22 | ベタゲノン・エイビー | 癌治療におけるチアゾール誘導体およびアナログの使用 |
| WO2010086613A1 (en) | 2009-01-30 | 2010-08-05 | Betagenon Ab | Compounds useful as inhibitors as ampk |
| JP2016526538A (ja) | 2013-06-20 | 2016-09-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺ダニ剤及び殺虫剤としてのアリールスルフィド誘導体及びアリールスルホキシド誘導体 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB690238A (en) * | 1949-08-23 | 1953-04-15 | Knoll Ag | Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine |
| DE841149C (de) * | 1949-11-01 | 1952-06-13 | Knoll Ag | Verfahren zur Herstellung von 3, 4-Dimethyl-5-phenyl-2-iminothiazolidin |
| DE910650C (de) * | 1951-09-14 | 1954-05-03 | Knoll Ag | Verfahren zur Herstellung von 2-Amino-í¸ -thiazolinen bzw. Thiazolidon-(2)-imiden undderen Salzen |
| US3297708A (en) * | 1965-10-06 | 1967-01-10 | American Cyanamid Co | Method of preparing thiazolidines |
| FR1510014A (fr) * | 1966-12-05 | 1968-01-19 | Aquitaine Petrole | Préparation de dithiolannes |
| SU465792A3 (ru) * | 1968-11-06 | 1975-03-30 | Хиноин Гиогисцер-Ес Вегиесцети Термекек Гиара Рт (Фирма) | Способ получени гетероциклических соединений |
| US3671537A (en) * | 1969-06-05 | 1972-06-20 | Gyogyszerkutato Intezet | Certain 3-(2,6-dichlorophenyl)-2-iminothiazolidines |
| US3898340A (en) * | 1970-04-15 | 1975-08-05 | Bayer Ag | Aryliminothiazolidine compositions and methods |
| CH533420A (de) * | 1970-06-23 | 1973-02-15 | Agripat Sa | Mittel zur Regulierung des Pflanzenwachstums und zur Erhöhung des Zuckergehaltes in Zuckerrohr |
| US4029803A (en) * | 1976-05-03 | 1977-06-14 | Merck & Co., Inc. | Method of treatment with 2-iminothiazolidines and thiazolines |
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| HU180240B (en) * | 1978-04-21 | 1983-02-28 | Gyogyszerkutato Intezet | Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines |
| US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
| JPS59227870A (ja) * | 1983-06-07 | 1984-12-21 | Yamanouchi Pharmaceut Co Ltd | 新規２−グアニジノチアゾリン誘導体ならびにその製造法 |
-
1984
- 1984-04-25 HU HU841581A patent/HU191408B/hu not_active IP Right Cessation
-
1985
- 1985-04-22 BE BE1/011242A patent/BE902249A/fr not_active IP Right Cessation
- 1985-04-23 CH CH1736/85A patent/CH664564A5/de not_active IP Right Cessation
- 1985-04-23 ES ES542469A patent/ES8608499A1/es not_active Expired
- 1985-04-23 PT PT80336A patent/PT80336B/pt not_active IP Right Cessation
- 1985-04-23 FI FI851606A patent/FI82454C/fi not_active IP Right Cessation
- 1985-04-24 DD DD85275516A patent/DD231790A5/de not_active IP Right Cessation
- 1985-04-24 FR FR8506223A patent/FR2563519B1/fr not_active Expired
- 1985-04-24 IT IT8520482A patent/IT1208532B/it active
- 1985-04-24 DE DE19853514843 patent/DE3514843A1/de active Granted
- 1985-04-24 NL NL8501184A patent/NL8501184A/nl not_active Application Discontinuation
- 1985-04-24 PH PH32179A patent/PH20995A/en unknown
- 1985-04-24 GB GB08510457A patent/GB2159814B/en not_active Expired
- 1985-04-24 CA CA000480005A patent/CA1246086A/en not_active Expired
- 1985-04-24 JP JP8660885A patent/JPS6127974A/ja active Granted
- 1985-04-24 DK DK183585A patent/DK183585A/da not_active Application Discontinuation
- 1985-04-24 NO NO851638A patent/NO164417C/no unknown
- 1985-04-24 SE SE8501988A patent/SE464813B/sv not_active IP Right Cessation
- 1985-04-25 PL PL1985257822A patent/PL145084B1/pl unknown
- 1985-04-25 US US06/726,867 patent/US4665083A/en not_active Expired - Fee Related
- 1985-04-25 GR GR851006A patent/GR851006B/el unknown
- 1985-04-25 AT AT0124285A patent/AT394555B/de not_active IP Right Cessation
- 1985-04-25 SU SU853884105A patent/SU1366058A3/ru active
- 1985-04-25 CS CS853049A patent/CS255884B2/cs unknown
- 1985-04-25 PL PL1985257821A patent/PL144860B1/pl unknown
- 1985-04-25 PL PL1985253089A patent/PL144821B1/pl unknown
-
1986
- 1986-01-31 ES ES551481A patent/ES8701741A1/es not_active Expired
- 1986-01-31 ES ES551480A patent/ES8702391A1/es not_active Expired
- 1986-03-05 SU SU864027048A patent/SU1549480A3/ru active
- 1986-03-05 SU SU864027053A patent/SU1375132A3/ru active
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