ES2005441A6 - 2-Guanidino thiazole deriv. prodn. - Google Patents
2-Guanidino thiazole deriv. prodn.Info
- Publication number
- ES2005441A6 ES2005441A6 ES8703223A ES8703223A ES2005441A6 ES 2005441 A6 ES2005441 A6 ES 2005441A6 ES 8703223 A ES8703223 A ES 8703223A ES 8703223 A ES8703223 A ES 8703223A ES 2005441 A6 ES2005441 A6 ES 2005441A6
- Authority
- ES
- Spain
- Prior art keywords
- cyclisation
- obtd
- thiourea
- catalyst
- formula
- 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.)
- Expired
Links
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
- C07D277/20—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
- C07D277/28—Radicals substituted by nitrogen 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
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Produced 2-guanidino- 4-amidino- thiomethyl thiazole has formula (I). Cpd. (I) is obtd. by cyclisation of amidino-thiourea of formula (II) with 1,3-dihaloacetone, in an organic solvent, followed by reacting the cyclisation prod. of formula (III) (where X is halide ion), with thiourea in the presence of water, with heating, and conversion of obtd. dihydrohalide of (I) into a free base. Cyclisation is conducted in presence of catalyst comprising alkali metal (pref. sodium) iodide, using aliphatic 3-6C ketone (pref. acetone) or aliphatic 2-4C nitrile as solvent, in which the catalyst is dissolved. The reaction temp. is 20-40 deg.C. Prod. of cyclisation (III) is reacted with thiourea directly in the reaction mixt. obtd. at cyclisation stage. Alkali metal iodide (catalyst) is taken in amt. 4-6 mol.%. The yield of (I) is 85-90% and the content of biologically active substance is up to
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU864658A HU195959B (en) | 1986-11-12 | 1986-11-12 | Process for producing 2-guanidino-thiazole derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2005441A6 true ES2005441A6 (en) | 1989-03-01 |
Family
ID=10968597
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES8703223A Expired ES2005441A6 (en) | 1986-11-12 | 1987-11-12 | 2-Guanidino thiazole deriv. prodn. |
Country Status (14)
Country | Link |
---|---|
KR (1) | KR900006556B1 (en) |
AR (1) | AR243874A1 (en) |
AT (1) | AT389510B (en) |
CA (1) | CA1323032C (en) |
CS (1) | CS268693B2 (en) |
DK (1) | DK169966B1 (en) |
ES (1) | ES2005441A6 (en) |
FI (1) | FI84912C (en) |
GR (1) | GR871696B (en) |
HU (1) | HU195959B (en) |
NO (1) | NO167387C (en) |
PT (1) | PT86113B (en) |
SU (1) | SU1678205A3 (en) |
YU (1) | YU46086B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5731442A (en) * | 1997-03-11 | 1998-03-24 | Albemarle Corporation | Synthesis of thiazole derivatives |
US5856500A (en) * | 1997-03-11 | 1999-01-05 | Albemarle Corporation | Synthesis of thiazole derivatives |
-
1986
- 1986-11-12 HU HU864658A patent/HU195959B/en unknown
-
1987
- 1987-10-20 AT AT0277087A patent/AT389510B/en not_active IP Right Cessation
- 1987-10-21 CA CA000549936A patent/CA1323032C/en not_active Expired - Fee Related
- 1987-11-04 GR GR871696A patent/GR871696B/en unknown
- 1987-11-10 AR AR87309242A patent/AR243874A1/en active
- 1987-11-10 DK DK587287A patent/DK169966B1/en not_active IP Right Cessation
- 1987-11-11 PT PT86113A patent/PT86113B/en unknown
- 1987-11-11 NO NO874698A patent/NO167387C/en not_active IP Right Cessation
- 1987-11-12 YU YU204987A patent/YU46086B/en unknown
- 1987-11-12 ES ES8703223A patent/ES2005441A6/en not_active Expired
- 1987-11-12 FI FI875003A patent/FI84912C/en not_active IP Right Cessation
- 1987-11-12 CS CS878101A patent/CS268693B2/en not_active IP Right Cessation
- 1987-11-12 SU SU874203655A patent/SU1678205A3/en active
- 1987-11-19 KR KR1019870013045A patent/KR900006556B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HU195959B (en) | 1988-08-29 |
DK587287D0 (en) | 1987-11-10 |
SU1678205A3 (en) | 1991-09-15 |
AR243874A1 (en) | 1993-09-30 |
DK169966B1 (en) | 1995-04-18 |
KR900006556B1 (en) | 1990-09-13 |
NO167387C (en) | 1991-10-30 |
CA1323032C (en) | 1993-10-12 |
GR871696B (en) | 1987-12-08 |
CS810187A2 (en) | 1989-07-12 |
FI84912B (en) | 1991-10-31 |
NO167387B (en) | 1991-07-22 |
NO874698L (en) | 1988-05-13 |
KR890008120A (en) | 1989-07-08 |
PT86113B (en) | 1990-08-31 |
DK587287A (en) | 1988-05-13 |
ATA277087A (en) | 1989-05-15 |
NO874698D0 (en) | 1987-11-11 |
PT86113A (en) | 1987-12-01 |
YU204987A (en) | 1988-10-31 |
CS268693B2 (en) | 1990-04-11 |
FI84912C (en) | 1992-02-10 |
AT389510B (en) | 1989-12-27 |
FI875003A0 (en) | 1987-11-12 |
FI875003A (en) | 1988-06-13 |
YU46086B (en) | 1992-12-21 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
SA6 | Expiration date (snapshot 920101) |
Free format text: 2007-11-12 |
|
FD1A | Patent lapsed |
Effective date: 20071113 |