CA1323032C - Process for preparing 2-guanidinothiazole derivatives - Google Patents
Process for preparing 2-guanidinothiazole derivativesInfo
- Publication number
- CA1323032C CA1323032C CA000549936A CA549936A CA1323032C CA 1323032 C CA1323032 C CA 1323032C CA 000549936 A CA000549936 A CA 000549936A CA 549936 A CA549936 A CA 549936A CA 1323032 C CA1323032 C CA 1323032C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- compound
- iii
- solvent
- 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 - Fee Related
Links
- 150000008327 2-guanidinothiazoles Chemical class 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 19
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 claims abstract description 17
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000002955 isolation Methods 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 36
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract description 24
- 235000009518 sodium iodide Nutrition 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 5
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 7
- -1 chloromethyl compound Chemical class 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000003918 potentiometric titration Methods 0.000 description 3
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 2
- 229960001596 famotidine Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- FSKYYRZENXOYAP-UHFFFAOYSA-N 2-[4-(2-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CSCCC#N)=CS1 FSKYYRZENXOYAP-UHFFFAOYSA-N 0.000 description 1
- NMAKJOWVEDTHOA-UHFFFAOYSA-N 4-(chloromethyl)-1,3-thiazol-2-amine;hydron;chloride Chemical compound Cl.NC1=NC(CCl)=CS1 NMAKJOWVEDTHOA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XXFFVVWAHDVWFQ-UHFFFAOYSA-N O.Cl.Cl.N(C(=N)N)C=1SC=C(N1)CSC(N)=N Chemical compound O.Cl.Cl.N(C(=N)N)C=1SC=C(N1)CSC(N)=N XXFFVVWAHDVWFQ-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- C07D277/20—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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU864658A HU195959B (en) | 1986-11-12 | 1986-11-12 | Process for producing 2-guanidino-thiazole derivatives |
| HU4658/86 | 1986-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1323032C true CA1323032C (en) | 1993-10-12 |
Family
ID=10968597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000549936A Expired - Fee Related CA1323032C (en) | 1986-11-12 | 1987-10-21 | Process for preparing 2-guanidinothiazole derivatives |
Country Status (14)
| Country | Link |
|---|---|
| KR (1) | KR900006556B1 (cs) |
| AR (1) | AR243874A1 (cs) |
| AT (1) | AT389510B (cs) |
| CA (1) | CA1323032C (cs) |
| CS (1) | CS268693B2 (cs) |
| DK (1) | DK169966B1 (cs) |
| ES (1) | ES2005441A6 (cs) |
| FI (1) | FI84912C (cs) |
| GR (1) | GR871696B (cs) |
| HU (1) | HU195959B (cs) |
| NO (1) | NO167387C (cs) |
| PT (1) | PT86113B (cs) |
| SU (1) | SU1678205A3 (cs) |
| YU (1) | YU46086B (cs) |
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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6160673A (ja) * | 1984-08-30 | 1986-03-28 | Yamanouchi Pharmaceut Co Ltd | グアニジノチアゾ−ル誘導体の製造法 |
| ES8606309A1 (es) * | 1985-07-02 | 1986-04-01 | Lasa Lab | Procedimiento de obtencion de un derivado de la guanidina deintereses terapeutico |
-
1986
- 1986-11-12 HU HU864658A patent/HU195959B/hu unknown
-
1987
- 1987-10-20 AT AT0277087A patent/AT389510B/de 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/el unknown
- 1987-11-10 AR AR87309242A patent/AR243874A1/es active
- 1987-11-10 DK DK587287A patent/DK169966B1/da not_active IP Right Cessation
- 1987-11-11 NO NO874698A patent/NO167387C/no not_active IP Right Cessation
- 1987-11-11 PT PT86113A patent/PT86113B/pt unknown
- 1987-11-12 CS CS878101A patent/CS268693B2/cs not_active IP Right Cessation
- 1987-11-12 ES ES8703223A patent/ES2005441A6/es not_active Expired
- 1987-11-12 SU SU874203655A patent/SU1678205A3/ru active
- 1987-11-12 YU YU204987A patent/YU46086B/sh unknown
- 1987-11-12 FI FI875003A patent/FI84912C/fi not_active IP Right Cessation
- 1987-11-19 KR KR1019870013045A patent/KR900006556B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU1678205A3 (ru) | 1991-09-15 |
| AR243874A1 (es) | 1993-09-30 |
| DK169966B1 (da) | 1995-04-18 |
| YU204987A (en) | 1988-10-31 |
| PT86113A (en) | 1987-12-01 |
| ES2005441A6 (es) | 1989-03-01 |
| FI875003A0 (fi) | 1987-11-12 |
| FI84912B (fi) | 1991-10-31 |
| FI84912C (fi) | 1992-02-10 |
| DK587287D0 (da) | 1987-11-10 |
| HU195959B (en) | 1988-08-29 |
| NO167387B (no) | 1991-07-22 |
| NO874698L (no) | 1988-05-13 |
| AT389510B (de) | 1989-12-27 |
| YU46086B (sh) | 1992-12-21 |
| FI875003A7 (fi) | 1988-06-13 |
| DK587287A (da) | 1988-05-13 |
| PT86113B (pt) | 1990-08-31 |
| KR890008120A (ko) | 1989-07-08 |
| CS810187A2 (en) | 1989-07-12 |
| GR871696B (en) | 1987-12-08 |
| CS268693B2 (en) | 1990-04-11 |
| ATA277087A (de) | 1989-05-15 |
| NO874698D0 (no) | 1987-11-11 |
| NO167387C (no) | 1991-10-30 |
| KR900006556B1 (ko) | 1990-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |