GB1120735A - Improvements in or relating to thieno-benzothiazine derivatives - Google Patents
Improvements in or relating to thieno-benzothiazine derivativesInfo
- Publication number
- GB1120735A GB1120735A GB41479/65A GB4147965A GB1120735A GB 1120735 A GB1120735 A GB 1120735A GB 41479/65 A GB41479/65 A GB 41479/65A GB 4147965 A GB4147965 A GB 4147965A GB 1120735 A GB1120735 A GB 1120735A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- prepared
- compounds
- reacting
- 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
- UGKCYGNTLYESRY-UHFFFAOYSA-N 2H-thieno[2,3-h][1,2]benzothiazine Chemical class S1NC=CC2=C1C1=C(C=C2)SC=C1 UGKCYGNTLYESRY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 15
- -1 1-piperazinyl radical Chemical class 0.000 abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 abstract 1
- ITCHTIHSVATQQI-UHFFFAOYSA-N 1-bromo-3-iodopropane Chemical compound BrCCCI ITCHTIHSVATQQI-UHFFFAOYSA-N 0.000 abstract 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 abstract 1
- JXMZUNPWVXQADG-UHFFFAOYSA-N 1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1I JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 abstract 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 abstract 1
- UYIHKIRPUMUUJX-UHFFFAOYSA-N 3-bromo-2-nitrothiophene Chemical compound [O-][N+](=O)C=1SC=CC=1Br UYIHKIRPUMUUJX-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1316564A CH452531A (de) | 1964-10-09 | 1964-10-09 | Verfahren zur Herstellung von neuen Thieno-benzothiazin-Derivaten |
| CH1402164 | 1964-10-29 | ||
| CH1663264 | 1964-12-23 | ||
| CH449865 | 1965-04-01 | ||
| CH1169965 | 1965-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1120735A true GB1120735A (en) | 1968-07-24 |
Family
ID=27509201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41479/65A Expired GB1120735A (en) | 1964-10-09 | 1965-09-30 | Improvements in or relating to thieno-benzothiazine derivatives |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754641A (fr) * | 1969-08-11 | 1971-02-10 | Geigy Ag J R | Derives de l'imidazolidinone et medicaments contenant de tels derives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635096A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-07-19 | |||
| US3306897A (en) * | 1964-06-08 | 1967-02-28 | Sandoz Ltd | Thieno-benzothiopyran derivatives |
| CH467802A (de) * | 1964-10-01 | 1969-01-31 | Sandoz Ag | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
-
1964
- 1964-10-09 CH CH1316564A patent/CH452531A/de unknown
-
1965
- 1965-09-28 OA OA52200A patent/OA01827A/xx unknown
- 1965-09-29 BE BE670314A patent/BE670314A/xx unknown
- 1965-09-30 GB GB41479/65A patent/GB1120735A/en not_active Expired
- 1965-10-05 DE DE1620309A patent/DE1620309C3/de not_active Expired
- 1965-10-07 FI FI652385A patent/FI45661C/fi active
- 1965-10-07 NO NO159988A patent/NO115213B/no unknown
- 1965-10-07 AT AT907465A patent/AT251573B/de active
- 1965-10-08 NL NL6513059A patent/NL6513059A/xx unknown
- 1965-10-08 BR BR173883/65A patent/BR6573883D0/pt unknown
- 1965-10-08 SE SE13072/65A patent/SE346793B/xx unknown
- 1965-10-08 IL IL24433A patent/IL24433A/en unknown
- 1965-12-27 FR FR43798A patent/FR4912M/fr not_active Expired
-
1967
- 1967-10-18 US US676087A patent/US3478022A/en not_active Expired - Lifetime
-
1971
- 1971-04-29 CY CY58771A patent/CY587A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620309A1 (de) | 1970-03-12 |
| US3478022A (en) | 1969-11-11 |
| CH452531A (de) | 1968-03-15 |
| OA01827A (fr) | 1970-01-14 |
| SE346793B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-17 |
| NL6513059A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-04-12 |
| FI45661B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-05-02 |
| NO115213B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-09-02 |
| DE1620309C3 (de) | 1975-03-06 |
| BE670314A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-03-29 |
| BR6573883D0 (pt) | 1973-08-02 |
| CY587A (en) | 1971-04-29 |
| IL24433A (en) | 1969-04-30 |
| FR4912M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-13 |
| FI45661C (fi) | 1972-08-10 |
| AT251573B (de) | 1967-01-10 |
| DE1620309B2 (de) | 1974-07-18 |
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