DD157256A5 - Verfahren zur herstellung einer neuen kristallinen form von n-2-(6-methoxy)benzothiazolyl-n'-phenyl-harnstoff - Google Patents
Verfahren zur herstellung einer neuen kristallinen form von n-2-(6-methoxy)benzothiazolyl-n'-phenyl-harnstoff Download PDFInfo
- Publication number
- DD157256A5 DD157256A5 DD80218922A DD21892280A DD157256A5 DD 157256 A5 DD157256 A5 DD 157256A5 DD 80218922 A DD80218922 A DD 80218922A DD 21892280 A DD21892280 A DD 21892280A DD 157256 A5 DD157256 A5 DD 157256A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methoxy
- benzothiazolyl
- crystalline
- anhydrate
- urea
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000004682 monohydrates Chemical group 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- JHBWYQRKOUBPCA-UHFFFAOYSA-N 1-(6-methoxy-1,3-benzothiazol-2-yl)-3-phenylurea Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)NC1=CC=CC=C1 JHBWYQRKOUBPCA-UHFFFAOYSA-N 0.000 abstract description 10
- 229950008364 frentizole Drugs 0.000 abstract description 9
- 231100000219 mutagenic Toxicity 0.000 abstract description 5
- 230000003505 mutagenic effect Effects 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 1
- -1 Frentizol monohydrate Chemical class 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/010,553 US4223153A (en) | 1979-02-09 | 1979-02-09 | Crystalline forms of N-2-(6-methoxy)benzothiazolyl N'-phenyl urea |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD157256A5 true DD157256A5 (de) | 1982-10-27 |
Family
ID=21746293
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80218922A DD157256A5 (de) | 1979-02-09 | 1980-02-06 | Verfahren zur herstellung einer neuen kristallinen form von n-2-(6-methoxy)benzothiazolyl-n'-phenyl-harnstoff |
| DD80218923A DD149068A5 (de) | 1979-02-09 | 1980-02-06 | Verfahren zur herstellung von n-2-(6-methoxy)benzothiazolyl-n'-phenyl-harnstoff |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80218923A DD149068A5 (de) | 1979-02-09 | 1980-02-06 | Verfahren zur herstellung von n-2-(6-methoxy)benzothiazolyl-n'-phenyl-harnstoff |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4223153A (enFirst) |
| EP (1) | EP0014590A1 (enFirst) |
| JP (1) | JPS55105675A (enFirst) |
| AR (1) | AR225303A1 (enFirst) |
| AU (1) | AU5524080A (enFirst) |
| BE (1) | BE881563A (enFirst) |
| CA (2) | CA1131645A (enFirst) |
| DD (2) | DD157256A5 (enFirst) |
| DK (2) | DK52880A (enFirst) |
| ES (2) | ES488424A0 (enFirst) |
| FI (2) | FI800379A7 (enFirst) |
| FR (1) | FR2448538A1 (enFirst) |
| GB (1) | GB2042538A (enFirst) |
| GR (2) | GR70305B (enFirst) |
| IE (1) | IE800232L (enFirst) |
| IL (1) | IL59326A0 (enFirst) |
| IT (1) | IT1193918B (enFirst) |
| LU (1) | LU82141A1 (enFirst) |
| PH (1) | PH15154A (enFirst) |
| PL (2) | PL221872A1 (enFirst) |
| PT (2) | PT70779A (enFirst) |
| SU (2) | SU893132A3 (enFirst) |
| YU (1) | YU29680A (enFirst) |
| ZA (1) | ZA80668B (enFirst) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN182496B (enFirst) * | 1996-02-20 | 1999-04-17 | Reddy Research Foundation | |
| IN191496B (enFirst) | 1999-07-30 | 2003-12-06 | Ranbaxy Lab Ltd | |
| AR062927A1 (es) | 2006-10-11 | 2008-12-17 | Bayer Healthcare Ag | 4- [4-( [ [ 4- cloro-3-( trifluorometil) fenil) carbamoil] amino] -3- fluorofenoxi) -n- metilpiridin-2- carboxamida monohidratada |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088768A (en) * | 1975-05-06 | 1978-05-09 | Eli Lilly And Company | N-heterocyclic ureas as immune regulants |
-
1979
- 1979-02-09 US US06/010,553 patent/US4223153A/en not_active Expired - Lifetime
-
1980
- 1980-02-05 YU YU00296/80A patent/YU29680A/xx unknown
- 1980-02-05 ZA ZA00800668A patent/ZA80668B/xx unknown
- 1980-02-05 CA CA345,060A patent/CA1131645A/en not_active Expired
- 1980-02-05 AU AU55240/80A patent/AU5524080A/en not_active Abandoned
- 1980-02-05 PT PT70779A patent/PT70779A/pt unknown
- 1980-02-05 PT PT70780A patent/PT70780A/pt unknown
- 1980-02-05 FR FR8002503A patent/FR2448538A1/fr not_active Withdrawn
- 1980-02-06 JP JP1348280A patent/JPS55105675A/ja active Pending
- 1980-02-06 GR GR61138A patent/GR70305B/el unknown
- 1980-02-06 IL IL8059326A patent/IL59326A0/xx unknown
- 1980-02-06 BE BE1/9711A patent/BE881563A/fr unknown
- 1980-02-06 DD DD80218922A patent/DD157256A5/de unknown
- 1980-02-06 LU LU82141A patent/LU82141A1/fr unknown
- 1980-02-06 GR GR61139A patent/GR70306B/el unknown
- 1980-02-06 PH PH23605A patent/PH15154A/en unknown
- 1980-02-06 DD DD80218923A patent/DD149068A5/de unknown
- 1980-02-07 DK DK52880A patent/DK52880A/da unknown
- 1980-02-07 DK DK52980A patent/DK52980A/da unknown
- 1980-02-07 FI FI800379A patent/FI800379A7/fi not_active Application Discontinuation
- 1980-02-07 IE IE800232A patent/IE800232L/xx unknown
- 1980-02-07 PL PL22187280A patent/PL221872A1/xx unknown
- 1980-02-07 EP EP80300368A patent/EP0014590A1/en not_active Withdrawn
- 1980-02-07 PL PL22187380A patent/PL221873A1/xx unknown
- 1980-02-07 IT IT19771/80A patent/IT1193918B/it active
- 1980-02-07 GB GB8004139A patent/GB2042538A/en not_active Withdrawn
- 1980-02-07 FI FI800378A patent/FI800378A7/fi not_active Application Discontinuation
- 1980-02-08 SU SU802877707A patent/SU893132A3/ru active
- 1980-02-08 ES ES488424A patent/ES488424A0/es active Granted
- 1980-02-08 AR AR279909A patent/AR225303A1/es active
- 1980-02-08 SU SU802877902A patent/SU900811A3/ru active
- 1980-02-08 ES ES488425A patent/ES488425A0/es active Granted
-
1982
- 1982-04-23 CA CA000401603A patent/CA1144932A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD149068A5 (de) | 1981-06-24 |
| ES8101570A1 (es) | 1980-12-16 |
| YU29680A (en) | 1983-10-31 |
| ES8101571A1 (es) | 1980-12-16 |
| DK52980A (da) | 1980-08-10 |
| IL59326A0 (en) | 1980-05-30 |
| AR225303A1 (es) | 1982-03-15 |
| ZA80668B (en) | 1981-09-30 |
| GR70306B (enFirst) | 1982-09-07 |
| EP0014590A1 (en) | 1980-08-20 |
| FI800378A7 (fi) | 1981-01-01 |
| IT1193918B (it) | 1988-08-31 |
| ES488424A0 (es) | 1980-12-16 |
| PL221872A1 (enFirst) | 1980-12-15 |
| DK52880A (da) | 1980-08-10 |
| PH15154A (en) | 1982-08-24 |
| JPS55105675A (en) | 1980-08-13 |
| PT70780A (en) | 1980-03-01 |
| LU82141A1 (fr) | 1980-05-07 |
| PL221873A1 (enFirst) | 1980-10-20 |
| GR70305B (enFirst) | 1982-09-07 |
| SU900811A3 (ru) | 1982-01-23 |
| US4223153A (en) | 1980-09-16 |
| CA1131645A (en) | 1982-09-14 |
| AU5524080A (en) | 1980-08-14 |
| ES488425A0 (es) | 1980-12-16 |
| SU893132A3 (ru) | 1981-12-23 |
| PT70779A (en) | 1980-03-01 |
| FI800379A7 (fi) | 1981-01-01 |
| BE881563A (fr) | 1980-08-06 |
| IT8019771A0 (it) | 1980-02-07 |
| IE800232L (en) | 1980-08-09 |
| CA1144932A (en) | 1983-04-19 |
| GB2042538A (en) | 1980-09-24 |
| FR2448538A1 (fr) | 1980-09-05 |
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