DE2323465A1 - Thiazolderivate und verfahren zu ihrer herstellung - Google Patents
Thiazolderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2323465A1 DE2323465A1 DE2323465A DE2323465A DE2323465A1 DE 2323465 A1 DE2323465 A1 DE 2323465A1 DE 2323465 A DE2323465 A DE 2323465A DE 2323465 A DE2323465 A DE 2323465A DE 2323465 A1 DE2323465 A1 DE 2323465A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- hydroxyethyl
- compound
- thiazole
- production
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000007979 thiazole derivatives Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- MCZZVJMCQWYUEI-UHFFFAOYSA-N 2-bromo-n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(=O)CBr MCZZVJMCQWYUEI-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- CBEZEZZIXCULJW-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methyl-3h-1,3-thiazole-2-thione Chemical compound CC=1NC(=S)SC=1CCO CBEZEZZIXCULJW-UHFFFAOYSA-N 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 description 1
- 101000944174 Homo sapiens Histone acetyltransferase KAT6B Proteins 0.000 description 1
- -1 N, N-diisopropyl acetamide bromide Chemical compound 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/173—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing halogen
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/36—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2156772A GB1364779A (en) | 1972-05-09 | 1972-05-09 | Thiazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2323465A1 true DE2323465A1 (de) | 1973-11-22 |
Family
ID=10165089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2323465A Pending DE2323465A1 (de) | 1972-05-09 | 1973-05-09 | Thiazolderivate und verfahren zu ihrer herstellung |
Country Status (11)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022095A3 (en) * | 1995-01-18 | 1997-02-27 | Alteon Inc | Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation endproducts |
| US6007865A (en) * | 1995-01-18 | 1999-12-28 | Alteon Inc. | Reversing the formation of advanced glycosylation endproducts |
| USRE38330E1 (en) | 1995-01-18 | 2003-11-25 | Alteon Inc. | Preventing and reversing advanced glycosylation endproducts |
| US7511036B2 (en) | 2003-04-18 | 2009-03-31 | Synvista Therapeutics, Inc. | Dihydrothiazine prodrugs of thiazolium agents |
-
1972
- 1972-05-09 GB GB2156772A patent/GB1364779A/en not_active Expired
-
1973
- 1973-04-18 ZA ZA732677A patent/ZA732677B/xx unknown
- 1973-04-18 BE BE130148A patent/BE798385A/xx unknown
- 1973-04-19 AU AU54763/73A patent/AU5476373A/en not_active Expired
- 1973-04-24 JP JP4581073A patent/JPS5314069B2/ja not_active Expired
- 1973-05-01 NL NL7306033A patent/NL7306033A/xx unknown
- 1973-05-04 FR FR7316024A patent/FR2183766B3/fr not_active Expired
- 1973-05-04 FR FR7316025A patent/FR2183767B1/fr not_active Expired
- 1973-05-08 ES ES414516A patent/ES414516A1/es not_active Expired
- 1973-05-09 AR AR247934A patent/AR196248A1/es active
- 1973-05-09 AT AT408673A patent/AT323157B/de not_active IP Right Cessation
- 1973-05-09 DE DE2323465A patent/DE2323465A1/de active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022095A3 (en) * | 1995-01-18 | 1997-02-27 | Alteon Inc | Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation endproducts |
| US5853703A (en) * | 1995-01-18 | 1998-12-29 | The Picower Institute For Medical Research | Preventing and reversing the formation of advanced glycosylation endproducts |
| US6007865A (en) * | 1995-01-18 | 1999-12-28 | Alteon Inc. | Reversing the formation of advanced glycosylation endproducts |
| US6440749B1 (en) | 1995-01-18 | 2002-08-27 | Alteon. Inc. | Method of treating certain indications associated with hyperglycemia |
| USRE38330E1 (en) | 1995-01-18 | 2003-11-25 | Alteon Inc. | Preventing and reversing advanced glycosylation endproducts |
| US7022719B2 (en) | 1995-01-18 | 2006-04-04 | Alteon, Inc. | Preventing and reversing the formation of advance glycosylation endproducts |
| US7511036B2 (en) | 2003-04-18 | 2009-03-31 | Synvista Therapeutics, Inc. | Dihydrothiazine prodrugs of thiazolium agents |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1364779A (en) | 1974-08-29 |
| FR2183766A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| AR196248A1 (es) | 1973-12-10 |
| NL7306033A (enrdf_load_stackoverflow) | 1973-11-13 |
| ZA732677B (en) | 1974-03-27 |
| AT323157B (de) | 1975-06-25 |
| BE798385A (fr) | 1973-10-18 |
| FR2183767A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| FR2183767B1 (enrdf_load_stackoverflow) | 1976-12-03 |
| ES414516A1 (es) | 1976-05-01 |
| FR2183766B3 (enrdf_load_stackoverflow) | 1976-04-23 |
| JPS4954367A (enrdf_load_stackoverflow) | 1974-05-27 |
| JPS5314069B2 (enrdf_load_stackoverflow) | 1978-05-15 |
| AU5476373A (en) | 1974-10-24 |
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