IE37439B1 - New pharmacologically active anilinobenzothiazoles - Google Patents
New pharmacologically active anilinobenzothiazolesInfo
- Publication number
- IE37439B1 IE37439B1 IE460/73A IE46073A IE37439B1 IE 37439 B1 IE37439 B1 IE 37439B1 IE 460/73 A IE460/73 A IE 460/73A IE 46073 A IE46073 A IE 46073A IE 37439 B1 IE37439 B1 IE 37439B1
- Authority
- IE
- Ireland
- Prior art keywords
- general formula
- ylethoxy
- pyrrolidin
- reacting
- benzothiazole
- Prior art date
Links
- QDTDFSFRIDFTCF-UHFFFAOYSA-N n-phenyl-1,3-benzothiazol-2-amine Chemical class N=1C2=CC=CC=C2SC=1NC1=CC=CC=C1 QDTDFSFRIDFTCF-UHFFFAOYSA-N 0.000 title 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- FEWZKVRASRNBOH-UHFFFAOYSA-N n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,3-benzothiazol-2-amine Chemical class C=1C=C(NC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCCC1 FEWZKVRASRNBOH-UHFFFAOYSA-N 0.000 abstract 3
- WKGAFKNWVGABDG-UHFFFAOYSA-N 1-[2-(4-isothiocyanatophenoxy)ethyl]pyrrolidine Chemical compound C1=CC(N=C=S)=CC=C1OCCN1CCCC1 WKGAFKNWVGABDG-UHFFFAOYSA-N 0.000 abstract 2
- OTYZNDKWNPQQJP-UHFFFAOYSA-N 4-(2-pyrrolidin-1-ylethoxy)aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCCC1 OTYZNDKWNPQQJP-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 2
- QUFFMFMGOVRDIM-UHFFFAOYSA-N n-(4-ethoxyphenyl)-1,3-benzothiazol-2-amine Chemical class C1=CC(OCC)=CC=C1NC1=NC2=CC=CC=C2S1 QUFFMFMGOVRDIM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- JQRJWBDPSJFJPY-UHFFFAOYSA-N 4-(2-chloroethoxy)aniline Chemical compound NC1=CC=C(OCCCl)C=C1 JQRJWBDPSJFJPY-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical class CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- -1 methylsulphonyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1501872A GB1417402A (en) | 1972-03-30 | 1972-03-30 | Pharmacologically active anilinobenzothiazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37439L IE37439L (en) | 1973-09-30 |
| IE37439B1 true IE37439B1 (en) | 1977-07-20 |
Family
ID=10051624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE460/73A IE37439B1 (en) | 1972-03-30 | 1973-03-21 | New pharmacologically active anilinobenzothiazoles |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3897443A (enExample) |
| JP (1) | JPS4924959A (enExample) |
| AR (4) | AR210050A1 (enExample) |
| AT (1) | AT323738B (enExample) |
| BE (1) | BE797623A (enExample) |
| CA (1) | CA1019747A (enExample) |
| CH (1) | CH576976A5 (enExample) |
| CS (4) | CS184324B2 (enExample) |
| DE (1) | DE2315791A1 (enExample) |
| ES (4) | ES413153A1 (enExample) |
| FR (1) | FR2182910B1 (enExample) |
| GB (1) | GB1417402A (enExample) |
| HU (1) | HU164716B (enExample) |
| IE (1) | IE37439B1 (enExample) |
| LU (1) | LU67336A1 (enExample) |
| NL (1) | NL7304353A (enExample) |
| SE (1) | SE381874B (enExample) |
| SU (3) | SU556729A3 (enExample) |
| ZA (1) | ZA731867B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU534093B2 (en) * | 1979-03-19 | 1984-01-05 | Ici Australia Limited | Thiazoles,benzthiazoles, benzoxazoles and benzimidazoles |
| SE0104140D0 (sv) * | 2001-12-07 | 2001-12-07 | Astrazeneca Ab | Novel Compounds |
| ATE398613T1 (de) | 2005-02-16 | 2008-07-15 | Astrazeneca Ab | Chemische verbindungen |
| KR20080015409A (ko) * | 2005-05-16 | 2008-02-19 | 아스트라제네카 아베 | 티로신 키나제 억제제로서 유용한 피라졸릴아미노피리미딘 유도체 |
| WO2008129255A1 (en) * | 2007-04-18 | 2008-10-30 | Astrazeneca Ab | 5-aminopyrazol-3-yl-3h-imidazo [4,5-b] pyridine derivatives and their use for the treatment of cancer |
| JP2010526048A (ja) * | 2007-05-04 | 2010-07-29 | アストラゼネカ アクチボラグ | アミノ−チアゾリル−ピリミジン誘導体、および癌の治療のための該誘導体の使用 |
| UA99459C2 (en) * | 2007-05-04 | 2012-08-27 | Астразенека Аб | 9-(pyrazol-3-yl)- 9h-purine-2-amine and 3-(pyraz0l-3-yl)-3h-imidazo[4,5-b]pyridin-5-amine derivatives and their use for the treatment of cancer |
| WO2009150462A1 (en) * | 2008-06-11 | 2009-12-17 | Astrazeneca Ab | Tricyclic 2,4-diamin0-l,3,5-triazine derivatives useful for the treatment of cancer and myeloproliferative disorders |
| WO2010038060A1 (en) * | 2008-09-30 | 2010-04-08 | Astrazeneca Ab | Heterocyclic jak kinase inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2040928A (en) * | 1936-05-19 | |||
| US2676970A (en) * | 1952-01-30 | 1954-04-27 | Hoffmann La Roche | Benzothiazole derivatives |
| GB1153648A (en) * | 1967-03-22 | 1969-05-29 | Twyford Lab Ltd | Substituted 2-Anilino Benzothiazole Basic Ethers |
-
1972
- 1972-03-30 GB GB1501872A patent/GB1417402A/en not_active Expired
-
1973
- 1973-03-16 ZA ZA731867A patent/ZA731867B/xx unknown
- 1973-03-21 US US343565A patent/US3897443A/en not_active Expired - Lifetime
- 1973-03-21 IE IE460/73A patent/IE37439B1/xx unknown
- 1973-03-21 AT AT249473A patent/AT323738B/de not_active IP Right Cessation
- 1973-03-28 AR AR247274A patent/AR210050A1/es active
- 1973-03-28 CS CS7300002264A patent/CS184324B2/cs unknown
- 1973-03-28 CS CS7600004363A patent/CS184343B2/cs unknown
- 1973-03-28 CS CS7600004362A patent/CS184342B2/cs unknown
- 1973-03-28 CS CS7600004361A patent/CS184341B2/cs unknown
- 1973-03-29 DE DE2315791A patent/DE2315791A1/de active Pending
- 1973-03-29 SE SE7304423A patent/SE381874B/xx unknown
- 1973-03-29 ES ES413153A patent/ES413153A1/es not_active Expired
- 1973-03-29 HU HUBO1422A patent/HU164716B/hu unknown
- 1973-03-29 SU SU1900400A patent/SU556729A3/ru active
- 1973-03-29 FR FR7311300A patent/FR2182910B1/fr not_active Expired
- 1973-03-29 NL NL7304353A patent/NL7304353A/xx unknown
- 1973-03-29 CH CH455873A patent/CH576976A5/xx not_active IP Right Cessation
- 1973-03-30 LU LU67336A patent/LU67336A1/xx unknown
- 1973-03-30 JP JP48036585A patent/JPS4924959A/ja active Pending
- 1973-03-30 BE BE129526A patent/BE797623A/xx unknown
- 1973-03-30 CA CA167,578A patent/CA1019747A/en not_active Expired
-
1974
- 1974-01-01 AR AR252238A patent/AR204986A1/es active
- 1974-02-07 AR AR252237A patent/AR197545A1/es active
- 1974-10-01 SU SU2063383A patent/SU555853A3/ru active
- 1974-10-01 SU SU7402063381A patent/SU584775A3/ru active
- 1974-11-16 ES ES432027A patent/ES432027A1/es not_active Expired
- 1974-11-16 ES ES432026A patent/ES432026A1/es not_active Expired
-
1975
- 1975-10-09 ES ES441616A patent/ES441616A1/es not_active Expired
-
1976
- 1976-03-31 AR AR262741A patent/AR210756A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| SU555853A3 (ru) | 1977-04-25 |
| CS184341B2 (en) | 1978-08-31 |
| AT323738B (de) | 1975-07-25 |
| FR2182910B1 (enExample) | 1976-09-03 |
| HU164716B (enExample) | 1974-04-11 |
| CS184343B2 (en) | 1978-08-31 |
| SU556729A3 (ru) | 1977-04-30 |
| AR210050A1 (es) | 1977-06-30 |
| ES432027A1 (es) | 1976-11-01 |
| SE381874B (sv) | 1975-12-22 |
| SU584775A3 (ru) | 1977-12-15 |
| CA1019747A (en) | 1977-10-25 |
| ES441616A1 (es) | 1977-04-01 |
| BE797623A (fr) | 1973-07-16 |
| IE37439L (en) | 1973-09-30 |
| ZA731867B (en) | 1973-12-19 |
| AU5357273A (en) | 1974-09-26 |
| CS184324B2 (en) | 1978-08-31 |
| AR204986A1 (es) | 1976-03-31 |
| FR2182910A1 (enExample) | 1973-12-14 |
| CH576976A5 (enExample) | 1976-06-30 |
| LU67336A1 (enExample) | 1973-06-15 |
| AR197545A1 (es) | 1974-04-15 |
| CS184342B2 (en) | 1978-08-31 |
| NL7304353A (enExample) | 1973-10-02 |
| AR210756A1 (es) | 1977-09-15 |
| ES432026A1 (es) | 1976-11-01 |
| US3897443A (en) | 1975-07-29 |
| GB1417402A (en) | 1975-12-10 |
| DE2315791A1 (de) | 1973-10-04 |
| JPS4924959A (enExample) | 1974-03-05 |
| ES413153A1 (es) | 1976-01-16 |
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