BG60459B1 - МЕТОД ЗА ПОЛУЧАВАНЕ НА β-КАРБОНИЛ-КАРБОКСИАМИДИ НА 1,3-ТИАЗО- ЛИДИНИ - Google Patents
МЕТОД ЗА ПОЛУЧАВАНЕ НА β-КАРБОНИЛ-КАРБОКСИАМИДИ НА 1,3-ТИАЗО- ЛИДИНИ Download PDFInfo
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- BG60459B1 BG60459B1 BG92842A BG9284290A BG60459B1 BG 60459 B1 BG60459 B1 BG 60459B1 BG 92842 A BG92842 A BG 92842A BG 9284290 A BG9284290 A BG 9284290A BG 60459 B1 BG60459 B1 BG 60459B1
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- Prior art keywords
- formula
- thiazolidine
- group
- compounds
- compound
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- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 3
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- 239000011593 sulfur Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
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- -1 X is O Chemical group 0.000 abstract description 47
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
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- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000006165 cyclic alkyl group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
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- 239000012074 organic phase Substances 0.000 description 16
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 15
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- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 11
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- 239000000126 substance Substances 0.000 description 10
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- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 5
- 230000009610 hypersensitivity Effects 0.000 description 5
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GVOZKQGYCKWOJP-UHFFFAOYSA-N 3-[2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl]-3-oxopropanoic acid Chemical compound COC1=CC=CC=C1OCC1N(C(=O)CC(O)=O)CCS1 GVOZKQGYCKWOJP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
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- QVKXPWQMMKEVSI-UHFFFAOYSA-N 3-oxo-3-(1,3-thiazolidin-3-yl)propanoic acid Chemical compound OC(=O)CC(=O)N1CCSC1 QVKXPWQMMKEVSI-UHFFFAOYSA-N 0.000 description 2
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 231100000915 pathological change Toxicity 0.000 description 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Carbon And Carbon Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8819813A IT1216119B (it) | 1988-03-17 | 1988-03-17 | Beta_carbonil_carbossiamidi di 1,3_tiazolidine. |
| PCT/EP1989/000205 WO1989008648A1 (en) | 1988-03-17 | 1989-03-02 | beta-CARBONYL-CARBOXYAMIDES OF 1,3-THIAZOLIDINES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60459B1 true BG60459B1 (bg) | 1995-04-28 |
Family
ID=11161493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG92842A BG60459B1 (bg) | 1988-03-17 | 1990-09-14 | МЕТОД ЗА ПОЛУЧАВАНЕ НА β-КАРБОНИЛ-КАРБОКСИАМИДИ НА 1,3-ТИАЗО- ЛИДИНИ |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5206254A (sv) |
| EP (2) | EP0407403A1 (sv) |
| JP (1) | JPH0688987B2 (sv) |
| KR (1) | KR960011381B1 (sv) |
| AT (1) | ATE95814T1 (sv) |
| AU (1) | AU624124B2 (sv) |
| BG (1) | BG60459B1 (sv) |
| CA (1) | CA1325632C (sv) |
| DE (1) | DE68909815T2 (sv) |
| DK (1) | DK168486B1 (sv) |
| ES (1) | ES2059595T3 (sv) |
| FI (1) | FI95247C (sv) |
| HU (1) | HU205920B (sv) |
| IT (1) | IT1216119B (sv) |
| NO (1) | NO179370C (sv) |
| RO (1) | RO107656B1 (sv) |
| RU (1) | RU1833378C (sv) |
| WO (1) | WO1989008648A1 (sv) |
| ZA (1) | ZA892014B (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1245712B (it) * | 1991-04-09 | 1994-10-14 | Boehringer Mannheim Italia | Ammine eterocicliche utili terapia dell'asma e dell'infiammazione delle vie aeree |
| IT1270594B (it) * | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| US6586466B2 (en) | 1995-10-30 | 2003-07-01 | Smithkline Beecham Corporation | Carbohydrazide-protease inhibitors |
| US6083964A (en) * | 1998-02-18 | 2000-07-04 | K And K Biosciences, Inc. | Optical resolution of racemic aminoalkylpyridine anticonvulsants and (+) aminoalkylpyridine enantiomers as highly potent orally effective anticonvulsant drugs and excitatory amino acid antagonists |
| WO2000030446A1 (en) | 1998-11-23 | 2000-06-02 | Bonnie Davis | Dosage formulations for acetylcholinesterase inhibitors |
| CN1319955C (zh) * | 2003-06-10 | 2007-06-06 | 浙江海正药业股份有限公司 | 莫吉斯坦晶型 |
| WO2008144956A1 (fr) * | 2007-05-28 | 2008-12-04 | Tianjin Institute Of Pharmaceutical Research | Nouveaux composés ambroxol, leurs procédés de préparation et leurs utilisations |
| EP2070915A1 (en) * | 2007-12-03 | 2009-06-17 | A.M.S.A. ANONIMA MATERIE SINTETICHE E AFFINI S.p.A. | New process for the synthesis of moguisteine |
| CN102653527A (zh) * | 2011-12-22 | 2012-09-05 | 东莞达信生物技术有限公司 | 一种莫吉司坦合成工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195492B (en) * | 1984-07-27 | 1988-05-30 | Boehringer Biochemia Srl | Process for producing 2-substituted thiazolidine derivatives with antitussive and mucus regulating action and pharmaceuticals comprising these compounds as active ingredient |
| GB2164333B (en) * | 1984-07-27 | 1988-11-16 | Boehringer Biochemia Srl | Antitussive and mucus regulating 2-substituted thiazolidines |
| IT1201489B (it) * | 1985-11-13 | 1989-02-02 | Chiesi Farma Spa | Derivati di tiazolidina,loro procedimento di preparazione e formulazioni farmaceutiche |
| IT1228251B (it) * | 1987-07-02 | 1991-06-05 | Boehringer Biochemia Srl | Amidi di amino-tioacetali ciclici, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
-
1988
- 1988-03-17 IT IT8819813A patent/IT1216119B/it active
-
1989
- 1989-03-02 JP JP1502573A patent/JPH0688987B2/ja not_active Expired - Lifetime
- 1989-03-02 EP EP89902780A patent/EP0407403A1/en not_active Ceased
- 1989-03-02 HU HU891559A patent/HU205920B/hu unknown
- 1989-03-02 US US07/549,011 patent/US5206254A/en not_active Expired - Lifetime
- 1989-03-02 AU AU31892/89A patent/AU624124B2/en not_active Expired
- 1989-03-02 RO RO145944A patent/RO107656B1/ro unknown
- 1989-03-02 KR KR1019890702146A patent/KR960011381B1/ko not_active IP Right Cessation
- 1989-03-02 WO PCT/EP1989/000205 patent/WO1989008648A1/en active IP Right Grant
- 1989-03-11 DE DE89104349T patent/DE68909815T2/de not_active Expired - Lifetime
- 1989-03-11 ES ES89104349T patent/ES2059595T3/es not_active Expired - Lifetime
- 1989-03-11 EP EP89104349A patent/EP0333080B1/en not_active Expired - Lifetime
- 1989-03-11 AT AT89104349T patent/ATE95814T1/de not_active IP Right Cessation
- 1989-03-16 ZA ZA892014A patent/ZA892014B/xx unknown
- 1989-03-16 CA CA000593895A patent/CA1325632C/en not_active Expired - Lifetime
-
1990
- 1990-09-13 FI FI904512A patent/FI95247C/sv not_active IP Right Cessation
- 1990-09-14 DK DK221490A patent/DK168486B1/da not_active IP Right Cessation
- 1990-09-14 BG BG92842A patent/BG60459B1/bg unknown
- 1990-09-14 NO NO904031A patent/NO179370C/no not_active IP Right Cessation
- 1990-09-14 RU SU90A patent/RU1833378C/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| NO179370C (no) | 1996-09-25 |
| ES2059595T3 (es) | 1994-11-16 |
| IT1216119B (it) | 1990-02-22 |
| DK168486B1 (da) | 1994-04-05 |
| DK221490D0 (da) | 1990-09-14 |
| EP0407403A1 (en) | 1991-01-16 |
| KR960011381B1 (ko) | 1996-08-22 |
| DK221490A (da) | 1990-09-14 |
| EP0333080A1 (en) | 1989-09-20 |
| AU3189289A (en) | 1989-10-05 |
| HU205920B (en) | 1992-07-28 |
| RO107656B1 (ro) | 1993-12-30 |
| WO1989008648A1 (en) | 1989-09-21 |
| ATE95814T1 (de) | 1993-10-15 |
| AU624124B2 (en) | 1992-06-04 |
| JPH0688987B2 (ja) | 1994-11-09 |
| HU891559D0 (en) | 1991-06-28 |
| RU1833378C (en) | 1993-08-07 |
| FI95247B (sv) | 1995-09-29 |
| CA1325632C (en) | 1993-12-28 |
| NO904031D0 (no) | 1990-09-14 |
| IT8819813A0 (it) | 1988-03-17 |
| JPH03504123A (ja) | 1991-09-12 |
| FI904512A0 (sv) | 1990-09-13 |
| ZA892014B (en) | 1989-11-29 |
| US5206254A (en) | 1993-04-27 |
| FI95247C (sv) | 1996-01-10 |
| DE68909815D1 (de) | 1993-11-18 |
| DE68909815T2 (de) | 1994-03-24 |
| EP0333080B1 (en) | 1993-10-13 |
| HUT56355A (en) | 1991-08-28 |
| NO904031L (no) | 1990-11-16 |
| KR900700470A (ko) | 1990-08-13 |
| NO179370B (no) | 1996-06-17 |
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