GB1354538A - 6,11-dihydrodibenzo-b,e-thiepine derivatives - Google Patents
6,11-dihydrodibenzo-b,e-thiepine derivativesInfo
- Publication number
- GB1354538A GB1354538A GB3285171A GB3285171A GB1354538A GB 1354538 A GB1354538 A GB 1354538A GB 3285171 A GB3285171 A GB 3285171A GB 3285171 A GB3285171 A GB 3285171A GB 1354538 A GB1354538 A GB 1354538A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- july
- methyl
- metal salt
- prepared
- 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- KTBOWZRPDZLHQT-UHFFFAOYSA-N 5-oxo-6,11-dihydrobenzo[c][1]benzothiepin-11-ol Chemical compound C1S(=O)C2=CC=CC=C2C(O)C2=CC=CC=C21 KTBOWZRPDZLHQT-UHFFFAOYSA-N 0.000 abstract 1
- JLRRONOEUGUFFI-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzothiepin-11-ol Chemical compound C1SC2=CC=CC=C2C(O)C2=CC=CC=C21 JLRRONOEUGUFFI-UHFFFAOYSA-N 0.000 abstract 1
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical class C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 208000007107 Stomach Ulcer Diseases 0.000 abstract 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 abstract 1
- 229960004373 acetylcholine Drugs 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229960001340 histamine Drugs 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 231100000820 toxicity test Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
1354538 Tropanyloxy - dibenzothiepine derivatives SANDOZ Ltd 13 July 1971 [15 July 1970 (4)] 32851/71 Heading C2C Novel compounds of the general Formula I wherein R is C 1-4 alkyl and n is 1 or 2 or where R is other than methyl, is 0, may be prepared by (a) condensing an R substituted nortropane with a compound II wherein X is an acid radical of a reactive ester, (b) treatment of a compound I wherein n is 0 in neutral or weakly acid solution with an alkali metal salt or alkaline earth metal salt of periodic acid, or with the stiochiometric amount of an organic peracid or with the stiochiometric amount of hydrogen peroxide to obtain I in which n is 1, (c) oxidizing a compound I in which n is 0 or 1 with hydrogen peroxide or an organic peracid to I in which n is 2. The intermediate II (wherein X is chlorine) may be formed by treatment of the compound II wherein X is hydroxyl with hydrogen chloride or thionyl chloride. The intermediate I wherein n is zero and R is methyl may be formed by process (a) above. 6,11 - Dihydro - 11 - hydroxy - dibenzo[b,e]- thiepine - 5 - oxide may be prepared from 6,11 - dihydrodibenzo[b,e]thiepin - 11 - ol by process (b) above. Pharmaceutical compositions of compounds I with the usual excipients show activity in acetylcholine and histamine toxicity tests and against gastric ulcers.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1073870A CH529785A (en) | 1970-07-15 | 1970-07-15 | 11-(8-alkyl-3-nortropanyloxy)-6,11-dihydro-dibenzo(b,3) thiepin - derivs - used for treatment of stomach ulcers |
| CH1073670A CH529783A (en) | 1970-07-15 | 1970-07-15 | 11-(8-alkyl-3-nortropanyloxy)-6,11-dihydro-dibenzo(b,3) thiepin - derivs - used for treatment of stomach ulcers |
| CH1073770A CH529784A (en) | 1970-07-15 | 1970-07-15 | 11-(8-alkyl-3-nortropanyloxy)-6,11-dihydro-dibenzo(b,3) thiepin - derivs - used for treatment of stomach ulcers |
| CH1073570A CH528538A (en) | 1970-07-15 | 1970-07-15 | 11-(8-alkyl-3-nortropanyloxy)-6,11-dihydro-dibenzo(b,3) thiepin - derivs - used for treatment of stomach ulcers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1354538A true GB1354538A (en) | 1974-06-05 |
Family
ID=27429316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3285171A Expired GB1354538A (en) | 1970-07-15 | 1971-07-13 | 6,11-dihydrodibenzo-b,e-thiepine derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3716544A (en) |
| AU (1) | AU3116571A (en) |
| BE (1) | BE769968A (en) |
| DE (1) | DE2134820A1 (en) |
| FR (1) | FR2100908B1 (en) |
| GB (1) | GB1354538A (en) |
| HU (1) | HU163777B (en) |
| NL (1) | NL7109301A (en) |
| SE (1) | SE368955B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558107A (en) * | 1968-07-29 | 1971-01-26 | William Thomas Williams | Foaming agent mixer and method |
| CH582699A5 (en) * | 1973-03-26 | 1976-12-15 | Sandoz Ag | |
| CA1307790C (en) * | 1987-08-04 | 1992-09-22 | Ian Anthony Cliffe | Ethers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234235A (en) * | 1962-01-19 | 1966-02-08 | American Home Prod | Heterocyclic carbinols |
| CH476015A (en) * | 1965-06-28 | 1969-07-31 | Sandoz Ag | Process for the production of new tropane ethers |
| US3519633A (en) * | 1967-08-02 | 1970-07-07 | Mead Johnson & Co | Certain substituted 5,11-dihydro-10,10-dioxo - dibenz(c,f)(1,2)thiazepin - 5 - yloxyamines |
-
1971
- 1971-07-06 NL NL7109301A patent/NL7109301A/xx unknown
- 1971-07-13 FR FR7125570A patent/FR2100908B1/fr not_active Expired
- 1971-07-13 HU HUSA2220A patent/HU163777B/hu unknown
- 1971-07-13 GB GB3285171A patent/GB1354538A/en not_active Expired
- 1971-07-13 AU AU31165/71A patent/AU3116571A/en not_active Expired
- 1971-07-13 US US00162290A patent/US3716544A/en not_active Expired - Lifetime
- 1971-07-13 DE DE19712134820 patent/DE2134820A1/en active Pending
- 1971-07-13 BE BE769968A patent/BE769968A/en unknown
- 1971-07-14 SE SE09119/71A patent/SE368955B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3716544A (en) | 1973-02-13 |
| BE769968A (en) | 1972-01-13 |
| FR2100908B1 (en) | 1975-02-07 |
| NL7109301A (en) | 1972-01-18 |
| DE2134820A1 (en) | 1972-01-20 |
| HU163777B (en) | 1973-10-27 |
| SE368955B (en) | 1974-07-29 |
| FR2100908A1 (en) | 1972-03-24 |
| AU3116571A (en) | 1973-01-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES8704925A1 (en) | Benzothiazole and benzothiophene derivatives. | |
| ES8103743A1 (en) | Phthalimidine derivatives and pharmaceutical compositions containing them. | |
| GB1511463A (en) | 1-acylamino methyl-1,2,3,4-tetrahydroisoquinolines | |
| JPS54121127A (en) | Photographic processing composition | |
| GB1354538A (en) | 6,11-dihydrodibenzo-b,e-thiepine derivatives | |
| JPS55137529A (en) | Bleaching composition for photographic treatment | |
| GB1345052A (en) | ||
| ES8504815A1 (en) | Penem derivatives, and composition containing them | |
| GB999388A (en) | Improvements in or relating to 2-benzyloxy-malonic acid derivatives | |
| FR2377408A1 (en) | AMINO-SPIRO (OXA (OR THIA) CYCLOALCANE-PENAM) -CARBOXYLIC ACIDS | |
| KR850000026A (en) | Method and composition for preparing bicyclo (3.2.1) -octane carboxylic acid | |
| GB1473981A (en) | Hydrazino-cephalosporanic acid derivatives | |
| FR2380277A1 (en) | Antibacterial beta-lactam antibiotic - desacetyl-di:hydro-890A9 prepd. by enzymatic de:acetylation of di:hydro-890A9 and used e.g. as pharmaceutical or feed additive (NL 15.8.78) | |
| GB1219387A (en) | Bicyclo[2.2.2]oct-2-ene-amino acid compounds | |
| GB1163921A (en) | Azadibenzocycloheptene Derivatives | |
| GB1430188A (en) | Diaza-oxa-bicyclodecane derivatives | |
| GB1200981A (en) | Novel bis-p-chlorophenoxy-acetic acid esters, the preparation thereof and compositions containing the same | |
| GB1357027A (en) | Pleiadene and dibenzoheptalene derivatives | |
| GB833807A (en) | Benzhydryl ethers | |
| GB1265866A (en) | ||
| GB1258967A (en) | ||
| GB1289132A (en) | ||
| GB1347643A (en) | Chloro compounds | |
| GB1302494A (en) | ||
| GB1489784A (en) | Pharmaceutically active substituted keto-acid derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |