ES332985A2 - Improvements in or relating to 4h-benzo(4,5)cyclohepta (1,2-b) thiophene derivatives - Google Patents
Improvements in or relating to 4h-benzo(4,5)cyclohepta (1,2-b) thiophene derivativesInfo
- Publication number
- ES332985A2 ES332985A2 ES332985A ES332985A ES332985A2 ES 332985 A2 ES332985 A2 ES 332985A2 ES 332985 A ES332985 A ES 332985A ES 332985 A ES332985 A ES 332985A ES 332985 A2 ES332985 A2 ES 332985A2
- Authority
- ES
- Spain
- Prior art keywords
- formula
- cyclohepta
- benzo
- acid
- thiophen
- 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
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 2
- -1 chloroformic acid ester Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- BYSDXOIAAYZTBJ-UHFFFAOYSA-N 2-(2-thiophen-2-ylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CS1 BYSDXOIAAYZTBJ-UHFFFAOYSA-N 0.000 abstract 1
- ISSJZCAENPGUEW-BQYQJAHWSA-N 2-[(e)-2-thiophen-2-ylethenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1\C=C\C1=CC=CS1 ISSJZCAENPGUEW-BQYQJAHWSA-N 0.000 abstract 1
- JAGBUENUSNSSFW-UHFFFAOYSA-N 4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=C1SC=C2 JAGBUENUSNSSFW-UHFFFAOYSA-N 0.000 abstract 1
- XBSHFWJFRSEMTE-UHFFFAOYSA-N 6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ol Chemical class S1C2=C(C=C1)C(C1=C(C=C2)C=CC=C1)O XBSHFWJFRSEMTE-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AZLFZBHRVLSJRH-UHFFFAOYSA-N N,N-dimethyl-3-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ylidene)propan-1-amine Chemical compound CN(CCC=C1C2=C(C=CC=3SC=CC31)C=CC=C2)C AZLFZBHRVLSJRH-UHFFFAOYSA-N 0.000 abstract 1
- 206010029333 Neurosis Diseases 0.000 abstract 1
- 208000012545 Psychophysiologic disease Diseases 0.000 abstract 1
- 208000028017 Psychotic disease Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- AKYJPOPHGMQXHH-UHFFFAOYSA-N benzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=C1SC=C2 AKYJPOPHGMQXHH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 208000015238 neurotic disease Diseases 0.000 abstract 1
- JKNKNWJNCOJPLI-UHFFFAOYSA-N o-phthalaldehydic acid Chemical compound C1=CC=C2C(O)OC(=O)C2=C1 JKNKNWJNCOJPLI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 150000003673 urethanes Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel compounds of Formula I <FORM:1089483/C2/1> in which R1 signifies a hydrogen, chlorine or bromine atom, and Z signifies -CH = CH- or -CH2CH2-, and their acid addition salts, are prepared by hydrolysing a compound of Formula IV <FORM:1089483/C2/2> and, if required, reacting the resulting compound with an organic or inorganic acid. The urethanes of Formula IV are made by reacting a 4 - (3 - dimethylaminopropylidene) - 4H - benzo - [4,5] - cyclohepta[1,2-b]thiophene of Formula II <FORM:1089483/C2/3> with a chloroformic acid ester ClCOOR2. Compounds of Formula II can be made by condensing 2-thenyl-diethylphosphonate with an o-phthalaldehydic acid, reducing the resulting 2 - [2 - (2 - thienyl) - vinyl] - benzoic acid, and subjecting the 2 - [2 - (2 - thienyl) - ethyl] - benzoic acid obtained to an intramolecular ring closure to give a 9,10-dihydro-4H -benzo[4,5]cyclohepta-[1,2-b]thiophen-4-one which may be dehydrogenated, the 4H-benzo[4,5]cyclohepta[1,2-b]-thiophen-4-one of Formula V <FORM:1089483/C2/4> reacted with a 3-dimethylaminopropyl-magnesium halide and the resulting 4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol derivative treated with an agent for removing water. Therapeutic compositions useful in the treatment of neurotic, psychotic and psychosomatic disorders, and which may be administered enterally or parenterally comprise as active ingredient a compound of Formula I above and/or and acid addition salt thereof.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH127564A CH440321A (en) | 1964-02-04 | 1964-02-04 | Process for the preparation of new heterocyclic compounds |
| CH1324664 | 1964-10-13 | ||
| CH806165A CH473138A (en) | 1964-02-04 | 1965-06-09 | Process for the preparation of new 9,10-dihydro-4H-benzo (4,5) cyclohepta (1,2-b) thiophene derivatives |
| CH1519165A CH473146A (en) | 1964-02-04 | 1965-11-03 | Process for the preparation of new 4H-Benzo (4,5) cyclohepta (1,2-b) thiophene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES332985A2 true ES332985A2 (en) | 1968-03-16 |
Family
ID=27428140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES332985A Expired ES332985A2 (en) | 1964-02-04 | 1966-11-02 | Improvements in or relating to 4h-benzo(4,5)cyclohepta (1,2-b) thiophene derivatives |
Country Status (12)
| Country | Link |
|---|---|
| BE (2) | BE659178A (en) |
| BR (2) | BR6566936D0 (en) |
| CH (2) | CH473138A (en) |
| DE (2) | DE1238040B (en) |
| ES (1) | ES332985A2 (en) |
| FI (1) | FI42216B (en) |
| FR (4) | FR1441486A (en) |
| GB (2) | GB1089483A (en) |
| IL (1) | IL22905A (en) |
| NL (2) | NL125442C (en) |
| OA (1) | OA01524A (en) |
| SE (1) | SE306323B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195800B (en) * | 1983-10-13 | 1988-07-28 | Sandoz Ltd | Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them |
| PL353586A1 (en) | 1999-09-13 | 2003-12-01 | Bridge Pharma, Inc.Bridge Pharma, Inc. | Optically active isomers of ketotifen and therapeutically active metabolites thereof |
-
1965
- 1965-01-26 GB GB3355/65A patent/GB1089483A/en not_active Expired
- 1965-01-28 OA OA51413A patent/OA01524A/en unknown
- 1965-01-29 NL NL6501154A patent/NL125442C/xx active
- 1965-02-01 DE DES95277A patent/DE1238040B/en active Pending
- 1965-02-02 BE BE659178A patent/BE659178A/xx unknown
- 1965-02-02 FI FI0244/65A patent/FI42216B/fi active
- 1965-02-02 FR FR4164A patent/FR1441486A/en not_active Expired
- 1965-02-03 IL IL22905A patent/IL22905A/en unknown
- 1965-02-03 SE SE1405/65A patent/SE306323B/xx unknown
- 1965-02-04 BR BR166936/65A patent/BR6566936D0/en unknown
- 1965-04-30 FR FR15304A patent/FR4369M/fr not_active Expired
- 1965-06-09 CH CH806165A patent/CH473138A/en unknown
- 1965-08-09 BE BE668052A patent/BE668052A/xx unknown
- 1965-08-09 NL NL6510326A patent/NL6510326A/xx unknown
- 1965-08-10 FR FR27925A patent/FR91208E/en not_active Expired
- 1965-11-03 CH CH1519165A patent/CH473146A/en unknown
-
1966
- 1966-10-21 GB GB47266/66A patent/GB1159480A/en not_active Expired
- 1966-10-28 DE DE19661620420 patent/DE1620420A1/en active Pending
- 1966-10-31 BR BR184229/66A patent/BR6684229D0/en unknown
- 1966-11-02 ES ES332985A patent/ES332985A2/en not_active Expired
- 1966-11-02 FR FR82202A patent/FR92121E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE659178A (en) | 1965-08-02 |
| FR1441486A (en) | 1966-06-10 |
| CH473138A (en) | 1969-05-31 |
| NL125442C (en) | 1968-06-17 |
| IL22905A (en) | 1969-01-29 |
| BE668052A (en) | 1966-02-09 |
| SE306323B (en) | 1968-11-25 |
| GB1089483A (en) | 1967-11-01 |
| FR4369M (en) | 1966-08-22 |
| DE1238040B (en) | 1967-04-06 |
| GB1159480A (en) | 1969-07-23 |
| FI42216B (en) | 1970-03-02 |
| BR6684229D0 (en) | 1973-12-26 |
| FR91208E (en) | 1968-05-03 |
| DE1620420A1 (en) | 1970-03-12 |
| OA01524A (en) | 1969-07-21 |
| NL6510326A (en) | 1966-12-12 |
| NL6501154A (en) | 1965-08-05 |
| BR6566936D0 (en) | 1973-08-14 |
| FR92121E (en) | 1968-09-27 |
| CH473146A (en) | 1969-05-31 |
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