CA1131645A - Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl urea - Google Patents
Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl ureaInfo
- Publication number
- CA1131645A CA1131645A CA345,060A CA345060A CA1131645A CA 1131645 A CA1131645 A CA 1131645A CA 345060 A CA345060 A CA 345060A CA 1131645 A CA1131645 A CA 1131645A
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- benzothiazolyl
- phenylurea
- anhydrate
- frentizole
- 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
- -1 benzothiazolyl n'-phenyl urea Chemical compound 0.000 title description 5
- LUBJCRLGQSPQNN-UHFFFAOYSA-N Z-phenylurea Natural products NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title 1
- 150000004682 monohydrates Chemical group 0.000 claims abstract description 9
- LDFWEBWORFXBQN-UHFFFAOYSA-N 1-(1,3-benzothiazol-2-yl)-3-phenylurea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)NC1=CC=CC=C1 LDFWEBWORFXBQN-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229950008364 frentizole Drugs 0.000 abstract description 15
- 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 13
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000003505 mutagenic effect Effects 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- 231100000219 mutagenic Toxicity 0.000 abstract description 3
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 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
- 238000011835 investigation Methods 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
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 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
- 101100162169 Xenopus laevis adrm1-a gene Proteins 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
- 239000000356 contaminant Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000401603A CA1144932A (en) | 1979-02-09 | 1982-04-23 | Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl urea |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10,553 | 1979-02-09 | ||
| 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 |
|---|---|
| CA1131645A true CA1131645A (en) | 1982-09-14 |
Family
ID=21746293
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,060A Expired CA1131645A (en) | 1979-02-09 | 1980-02-05 | Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl urea |
| CA000401603A Expired CA1144932A (en) | 1979-02-09 | 1982-04-23 | Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl urea |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000401603A Expired CA1144932A (en) | 1979-02-09 | 1982-04-23 | Crystalline forms of n-2-(6-methoxy) benzothiazolyl n'-phenyl urea |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4223153A (OSRAM) |
| EP (1) | EP0014590A1 (OSRAM) |
| JP (1) | JPS55105675A (OSRAM) |
| AR (1) | AR225303A1 (OSRAM) |
| AU (1) | AU5524080A (OSRAM) |
| BE (1) | BE881563A (OSRAM) |
| CA (2) | CA1131645A (OSRAM) |
| DD (2) | DD149068A5 (OSRAM) |
| DK (2) | DK52980A (OSRAM) |
| ES (2) | ES488424A0 (OSRAM) |
| FI (2) | FI800378A7 (OSRAM) |
| FR (1) | FR2448538A1 (OSRAM) |
| GB (1) | GB2042538A (OSRAM) |
| GR (2) | GR70305B (OSRAM) |
| IE (1) | IE800232L (OSRAM) |
| IL (1) | IL59326A0 (OSRAM) |
| IT (1) | IT1193918B (OSRAM) |
| LU (1) | LU82141A1 (OSRAM) |
| PH (1) | PH15154A (OSRAM) |
| PL (2) | PL221872A1 (OSRAM) |
| PT (2) | PT70779A (OSRAM) |
| SU (2) | SU893132A3 (OSRAM) |
| YU (1) | YU29680A (OSRAM) |
| ZA (1) | ZA80668B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN182496B (OSRAM) * | 1996-02-20 | 1999-04-17 | Reddy Research Foundation | |
| IN191496B (OSRAM) | 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 PT PT70779A patent/PT70779A/pt unknown
- 1980-02-05 AU AU55240/80A patent/AU5524080A/en not_active Abandoned
- 1980-02-05 CA CA345,060A patent/CA1131645A/en not_active Expired
- 1980-02-05 PT PT70780A patent/PT70780A/pt unknown
- 1980-02-05 FR FR8002503A patent/FR2448538A1/fr not_active Withdrawn
- 1980-02-05 ZA ZA00800668A patent/ZA80668B/xx unknown
- 1980-02-05 YU YU00296/80A patent/YU29680A/xx unknown
- 1980-02-06 JP JP1348280A patent/JPS55105675A/ja active Pending
- 1980-02-06 DD DD80218923A patent/DD149068A5/de unknown
- 1980-02-06 IL IL8059326A patent/IL59326A0/xx unknown
- 1980-02-06 BE BE1/9711A patent/BE881563A/fr unknown
- 1980-02-06 GR GR61138A patent/GR70305B/el unknown
- 1980-02-06 PH PH23605A patent/PH15154A/en unknown
- 1980-02-06 LU LU82141A patent/LU82141A1/fr unknown
- 1980-02-06 DD DD80218922A patent/DD157256A5/de unknown
- 1980-02-06 GR GR61139A patent/GR70306B/el unknown
- 1980-02-07 IE IE800232A patent/IE800232L/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 DK DK52980A patent/DK52980A/da unknown
- 1980-02-07 EP EP80300368A patent/EP0014590A1/en not_active Withdrawn
- 1980-02-07 PL PL22187280A patent/PL221872A1/xx unknown
- 1980-02-07 PL PL22187380A patent/PL221873A1/xx unknown
- 1980-02-07 FI FI800378A patent/FI800378A7/fi not_active Application Discontinuation
- 1980-02-07 DK DK52880A patent/DK52880A/da unknown
- 1980-02-07 FI FI800379A patent/FI800379A7/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 ES ES488425A patent/ES488425A0/es active Granted
- 1980-02-08 SU SU802877902A patent/SU900811A3/ru active
-
1982
- 1982-04-23 CA CA000401603A patent/CA1144932A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1193918B (it) | 1988-08-31 |
| GR70305B (OSRAM) | 1982-09-07 |
| AR225303A1 (es) | 1982-03-15 |
| AU5524080A (en) | 1980-08-14 |
| DD157256A5 (de) | 1982-10-27 |
| LU82141A1 (fr) | 1980-05-07 |
| ES8101570A1 (es) | 1980-12-16 |
| FR2448538A1 (fr) | 1980-09-05 |
| IT8019771A0 (it) | 1980-02-07 |
| EP0014590A1 (en) | 1980-08-20 |
| DK52980A (da) | 1980-08-10 |
| US4223153A (en) | 1980-09-16 |
| CA1144932A (en) | 1983-04-19 |
| FI800378A7 (fi) | 1981-01-01 |
| PH15154A (en) | 1982-08-24 |
| PL221873A1 (OSRAM) | 1980-10-20 |
| PT70779A (en) | 1980-03-01 |
| IE800232L (en) | 1980-08-09 |
| ES8101571A1 (es) | 1980-12-16 |
| JPS55105675A (en) | 1980-08-13 |
| FI800379A7 (fi) | 1981-01-01 |
| ES488425A0 (es) | 1980-12-16 |
| GB2042538A (en) | 1980-09-24 |
| DD149068A5 (de) | 1981-06-24 |
| PL221872A1 (OSRAM) | 1980-12-15 |
| DK52880A (da) | 1980-08-10 |
| SU893132A3 (ru) | 1981-12-23 |
| ZA80668B (en) | 1981-09-30 |
| BE881563A (fr) | 1980-08-06 |
| PT70780A (en) | 1980-03-01 |
| SU900811A3 (ru) | 1982-01-23 |
| GR70306B (OSRAM) | 1982-09-07 |
| ES488424A0 (es) | 1980-12-16 |
| YU29680A (en) | 1983-10-31 |
| IL59326A0 (en) | 1980-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |