FI62313C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 2,3-dihydroimidazo(2,1-b)tiazolderivat - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 2,3-dihydroimidazo(2,1-b)tiazolderivat Download PDFInfo
- Publication number
- FI62313C FI62313C FI770759A FI770759A FI62313C FI 62313 C FI62313 C FI 62313C FI 770759 A FI770759 A FI 770759A FI 770759 A FI770759 A FI 770759A FI 62313 C FI62313 C FI 62313C
- Authority
- FI
- Finland
- Prior art keywords
- therapeutic
- methyl
- methoxyphenyl
- solution
- chloroform
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- LCCQUAVRRQQTLG-UHFFFAOYSA-N 2,3-dihydroimidazo[2,1-b][1,3]thiazole Chemical class C1=CN=C2SCCN21 LCCQUAVRRQQTLG-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- -1 triethylamine salts Chemical class 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 4
- 229940113118 carrageenan Drugs 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 239000000679 carrageenan Substances 0.000 description 4
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 4
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QWPKJGJJMQHNPQ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.NC1=NCCS1 QWPKJGJJMQHNPQ-UHFFFAOYSA-N 0.000 description 1
- IGXCFRMBNYEWED-UHFFFAOYSA-N 5,6-bis(4-methoxyphenyl)-2,3-dimethyl-2,3-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N2C(C)C(C)SC2=N1 IGXCFRMBNYEWED-UHFFFAOYSA-N 0.000 description 1
- OQGKVQSMTMVSGK-UHFFFAOYSA-N CC1=CCN(N1Cl)N Chemical compound CC1=CCN(N1Cl)N OQGKVQSMTMVSGK-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- XMFKCGOPTAQVJJ-UHFFFAOYSA-N Cl.CC1CSC(N)=N1 Chemical compound Cl.CC1CSC(N)=N1 XMFKCGOPTAQVJJ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9517/76A GB1541321A (en) | 1976-03-10 | 1976-03-10 | 2,3-dihydroimidazo(2,1-b)thiazole derivatives and process for their preparation |
| GB951776 | 1976-03-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI770759A7 FI770759A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-09-11 |
| FI62313B FI62313B (fi) | 1982-08-31 |
| FI62313C true FI62313C (fi) | 1982-12-10 |
Family
ID=9873507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI770759A FI62313C (fi) | 1976-03-10 | 1977-03-09 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 2,3-dihydroimidazo(2,1-b)tiazolderivat |
Country Status (28)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204067A (en) * | 1976-09-24 | 1980-05-20 | Adhikary Parimal K | Derivatives of imidazo[2,1-b] thiazole |
| US4263311A (en) * | 1976-09-27 | 1981-04-21 | Smithkline Corporation | 5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles |
| LU77703A1 (de) * | 1977-07-07 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
| US4153706A (en) | 1978-02-13 | 1979-05-08 | Smithkline Corporation | 6-Hydroxy-5,6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazoles |
| US4175127A (en) * | 1978-09-27 | 1979-11-20 | Smithkline Corporation | Pyridyl substituted 2,3-dihydroimidazo[2,1-b]thiazoles |
| PL221188A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1979-01-05 | 1980-12-01 | Ciba Geigy Ag | |
| US4364942A (en) * | 1979-06-21 | 1982-12-21 | Janssen Pharmaceutica N.V. | 2,3-Dihydro-imidazo (2,1-b)benzothiazoles compositions useful as anti-parkinsonism agents |
| FR2463774A1 (fr) * | 1979-08-21 | 1981-02-27 | Yamanouchi Pharma Co Ltd | Derives du 2-phenylimidazo(2,1-b)benzothiazole |
| FR2479831A1 (fr) * | 1980-04-08 | 1981-10-09 | Synthelabo | Derives de thiazole, leur preparation et leur application en therapeutique |
| US4327221A (en) * | 1980-10-15 | 1982-04-27 | American Home Products Corporation | 2-Substituted-3-hydroxythiazolo(2,3-8)-thiazolium salts and mesoionic didehydro derivatives thereof |
| US4719218A (en) * | 1985-12-12 | 1988-01-12 | Smithkline Beckman Corporation | Pyrrolo[1,2-a]imidazole and pyrrolo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitor |
| ZW24186A1 (en) * | 1985-12-12 | 1987-07-08 | Smithkline Beckman Corp | Inhibition of the 5-lipoxygenase pathway |
| US4751310A (en) * | 1985-12-12 | 1988-06-14 | Smithkline Beckman Corporation | Inhibition of the 5-lipoxygenase pathway |
| US5145858A (en) * | 1985-12-12 | 1992-09-08 | Smithkline Beecham Corp. | Pyrrolo [1,2-a] imidazole and imidazo [1,2a] pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| US5002941A (en) * | 1985-12-12 | 1991-03-26 | Smithkline Beecham Corporation | Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
| US5134150A (en) * | 1985-12-12 | 1992-07-28 | Smithkline Beecham Corporation | Inhibition of the 5-lipoxygenase pathway |
| US4794114A (en) * | 1986-08-19 | 1988-12-27 | Smithkline Beckman Corporation | Inhibition of interleukin-1 production by monocytes and/or macrophages |
| US5630014A (en) * | 1993-10-27 | 1997-05-13 | Nec Corporation | Gain controller with automatic adjustment using integration energy values |
| US6127387A (en) * | 1996-12-10 | 2000-10-03 | Thomas Jefferson University | Use of CD4-binding small molecules to inhibit immune responses |
| WO2007034282A2 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Diaryl-imidazole compounds condensed with a heterocycle as c3a receptor antagonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131034C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-05-11 | |||
| US3455924A (en) * | 1967-02-08 | 1969-07-15 | Upjohn Co | Dianisylimidazoles |
| NL164285C (nl) * | 1968-01-09 | 1980-12-15 | Rhone Poulenc Sa | Werkwijze ter bereiding van een farmaceutisch preparaat, dat een imidazoÿ2.1-bÿthiazoolderivaat bevat, de gevormde farmaceutische preparaten, alsmede werkwijze voor het bereiden van dit imidazoÿ2.1-bÿthiazoolderivaat. |
-
1976
- 1976-03-10 GB GB9517/76A patent/GB1541321A/en not_active Expired
-
1977
- 1977-03-02 IL IL51581A patent/IL51581A/xx unknown
- 1977-03-02 CH CH259777A patent/CH598267A5/xx not_active IP Right Cessation
- 1977-03-02 LU LU76879A patent/LU76879A1/xx unknown
- 1977-03-03 IE IE467/77A patent/IE44280B1/en unknown
- 1977-03-04 CA CA273,239A patent/CA1074324A/en not_active Expired
- 1977-03-04 FR FR7706434A patent/FR2343748A1/fr active Granted
- 1977-03-04 US US05/774,497 patent/US4110460A/en not_active Expired - Lifetime
- 1977-03-04 ZA ZA00771303A patent/ZA771303B/xx unknown
- 1977-03-05 DE DE19772709639 patent/DE2709639A1/de not_active Withdrawn
- 1977-03-07 ES ES456575A patent/ES456575A1/es not_active Expired
- 1977-03-07 NL NL7702446A patent/NL7702446A/xx not_active Application Discontinuation
- 1977-03-07 SE SE7702503A patent/SE431653B/xx unknown
- 1977-03-08 PT PT66278A patent/PT66278B/pt unknown
- 1977-03-08 BG BG035610A patent/BG28262A3/xx unknown
- 1977-03-08 YU YU00619/77A patent/YU61977A/xx unknown
- 1977-03-09 CS CS771589A patent/CS190341B2/cs unknown
- 1977-03-09 PL PL1977196539A patent/PL102603B1/pl unknown
- 1977-03-09 BE BE175621A patent/BE852259A/xx not_active IP Right Cessation
- 1977-03-09 HU HU77ME00002049A patent/HU172685B/hu unknown
- 1977-03-09 RO RO7789635A patent/RO71301A/ro unknown
- 1977-03-09 DK DK104677A patent/DK144702C/da not_active IP Right Cessation
- 1977-03-09 FI FI770759A patent/FI62313C/fi not_active IP Right Cessation
- 1977-03-09 NO NO770841A patent/NO150884C/no unknown
- 1977-03-10 AU AU23156/77A patent/AU503912B2/en not_active Expired
- 1977-03-10 JP JP52026581A patent/JPS5927357B2/ja not_active Expired
- 1977-03-10 AT AT164477A patent/AT352716B/de not_active IP Right Cessation
- 1977-03-10 SU SU772459651A patent/SU629882A3/ru active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI62313C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 2,3-dihydroimidazo(2,1-b)tiazolderivat | |
| DE69322033T2 (de) | Kondensierte Pyridin Derivate als Hemmer von Effekten freier Radikaler | |
| CA1150253A (en) | Dibenzoimidazoazepines, -oxazepines and -thiazepines and pharmaceutical compositions containing them | |
| DE1954584A1 (de) | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen | |
| US4088647A (en) | Pyrazino (1,2,3-ab)-β-carboline derivatives and salts thereof and method of preparing same | |
| US4163785A (en) | Benzothiazepine compounds and compositions | |
| DK164551B (da) | Analogifremgangsmaade til fremstilling af cyclohexylthienyleddikesyreamider eller fysiologisk taalelige syreadditionssalte deraf | |
| US4242348A (en) | Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters | |
| US3853872A (en) | 2,3,4,5-substituted thiazoles | |
| FI81788C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara fenotiazinfoereningar. | |
| NO824331L (no) | Fremgangsmaate ved fremstilling av 2-fenylimidazo(2,1-b)benzothiazolforbindelser | |
| US3708490A (en) | Imidazothiazolium compounds,preparation and method of use | |
| Leonard et al. | 2-Thenyl substituted diamines with antihistaminic activity | |
| PT87426B (pt) | Processo para a preparacao de derivados de imidazol | |
| JPS5849548B2 (ja) | ピリミジン化合物誘導体の製造法 | |
| FI74456C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva cystinderivat. | |
| FI70574C (fi) | Foerfarande foer framstaellning av nya farmaceutiskt anvaendbara derivat av 2-7(4-kinolinyl)-amino/-5-fluorbensoesyra | |
| GB2054593A (en) | 6-Alkyl-7-phenyl-1,6-naphthyridine- 5(6H)-one derivatives | |
| SU1205771A3 (ru) | Способ получени производных хиназолина или их солей с основани ми | |
| SU1544191A3 (ru) | Способ получени производных пиримидо/2,1- @ /бензотиазола | |
| US5098919A (en) | Pyrrolo(2,1-b)thiazole derivatives | |
| KR800001630B1 (ko) | 벤질아민의 제조방법 | |
| JPS62169782A (ja) | １−（アシルアミノメチル）イミダゾ〔１，２−ａ〕キノリン誘導体、その製造法および医薬への応用 | |
| US4044023A (en) | Novel basic substituted-alkylidenamino-oxylalkylcarboxylic-acid esters | |
| AU614690B2 (en) | Tricyclic triazolopyrimidine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: METABIO-JOULLIE |