IL41374A - Process for the production of 4-(1-alkyl-4-piperidylidene)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-10(9h)-ones and intermediates therefor - Google Patents
Process for the production of 4-(1-alkyl-4-piperidylidene)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-10(9h)-ones and intermediates thereforInfo
- Publication number
- IL41374A IL41374A IL41374A IL4137473A IL41374A IL 41374 A IL41374 A IL 41374A IL 41374 A IL41374 A IL 41374A IL 4137473 A IL4137473 A IL 4137473A IL 41374 A IL41374 A IL 41374A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- process according
- benzo
- alkyl
- Prior art date
Links
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
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1422443 Benzocycloheptathiophene derivatives SANDOZ Ltd 22 Jan 1973 [24 Jan 1972] 3119/73 Heading C2C A process for the production of benzocycloheptathiophene derivatives of the formula wherein R 1 is hydrogen, chlorine, bromine or (C 1 -C 4 ) alkoxy attached in the 6- or 7-position, and R 2 is (C 1 -C 4 )alkyl, comprises dehydrating a compound of the formula the starting material may be obtained by reacting a compound of the formula wherein X is chlorine or bromine, with an alcohol of the formula : R 3 OH wherein R 3 is (C 1 -C 4 ) alkyl, to give a compound of the formula splitting off the acid HX to give a compound of the formula reacting this compound with a Grignard reagent of the formula wherein Hal is chlorine, bromine or iodine, to give a compound of the formula and hydrolysing the enol ether group.
[GB1422443A]
Claims (6)
1. 41374-2 - 17 - 100-3680 CLAIMS; 1. A compound of formula XII, 9 10 wherein is in the 6 or 7 position of the benzo- cycloheptathiophene nucleus and is hydrogen, chlorine, bromine or alkoxy of 1 to 4 carbon atoms, and is alkyl of 1 to 4 carbon atoms, and 9 10 9 10 A - B is -CH2.C0- or -CH=C(0R3)- , wherein is alkyl of 1 to 4 carbon atoms .
2. A process for the production of a compound formula I, R , - 18 - 41374/3 wherein and R2 are as defined in claim 1, comprising dehydrating a compound of formula XII, defined in claim 1, and hydrolysing any enol ether' moiety present in the compound of formula XII. ^
3. A process according to claim 2 carried out using a strong aqueous acid.
4. A process according to claim 2 or 3, wherein the compound of formula XII used as starting material is a compound of the formula VII, wherein R^, R2 and R3 are as defined in claim 1.
5. A process according to claim 4, wherein the starting material of formula VII is produced by reacting a compound of formula V, 'wherein ^ and ^ are as defined, being in the 6 or 7 position of the benzo- . cycloheptathiophene nucleus, 41374-2 ¾ - 19 - 100-3680 with a compound of formula VI, wherein R~ is as defined, and Hal is chlorine, bromine or iodine, under Grignard conditions. 5. A process according to Claim 4, v/herein the compound of formula V is produced by splitting off the acid HX, wherein X is chlorine or bromine, from a compound of formula IV, wherein R^, ^ and X are as defined, R^ being in the 6 or 7 position of the benzo- cycloheptathiophene nucleus .
6. A process according to Claim 5, wherein the compounds of formula IV are produced by reacting a compound of formula II, 41374/3 - 20 - wherein R^ and X are as defined, being in the 6 or 7 position of the bonzo- cyclohepta hiophene nucleus with a compound of . formula III, v/herein R-, is as defined. 8* A process according to Claim 7, substantial as described herein with- reference to the Examples. 9. A process for the production of a compound of formula I, as defined in claim 2, substantially as hereinbefore defined with reference to Example 1. lO . A process according to any one of claims 2 to 9, wherein R. is hydrogen and R^ is methyl. 11." " A "Compoun -o- - - ormul-a—I--w enever. by a process as claimed in any one of claims 2 to 12. A compound of formula XII defined in claim 1, wherein A-B is -CH=C(0R3)-. 13. A compound of formula XII defined in claim 1, wherein A-B is -CH9rC0-'. - 21 - 41374/3 14. A compound of any one of claims 1, 11, 12 or 13, wherein is hydrogen and 1*2 is methyl. 15. 10-Methoxy-4- (l-methyl-4-piperldyl) -4H-benzo [4,5]cyclohepta[1,2]thiophen-4-ol. For the Ap
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98572A CH568312A5 (en) | 1972-01-24 | 1972-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41374A0 IL41374A0 (en) | 1973-03-30 |
| IL41374A true IL41374A (en) | 1976-08-31 |
Family
ID=4199789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41374A IL41374A (en) | 1972-01-24 | 1973-01-23 | Process for the production of 4-(1-alkyl-4-piperidylidene)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-10(9h)-ones and intermediates therefor |
Country Status (29)
| Country | Link |
|---|---|
| JP (2) | JPS566997B2 (en) |
| KR (1) | KR780000049B1 (en) |
| AR (1) | AR202094A1 (en) |
| AT (1) | AT334897B (en) |
| AU (1) | AU477308B2 (en) |
| BE (1) | BE794370A (en) |
| CA (1) | CA1006523A (en) |
| CH (1) | CH568312A5 (en) |
| CS (1) | CS183674B2 (en) |
| DD (1) | DD104084A5 (en) |
| DE (2) | DE2302970C3 (en) |
| DK (2) | DK154296C (en) |
| ES (1) | ES410855A1 (en) |
| FI (1) | FI60396C (en) |
| FR (2) | FR2169091B1 (en) |
| GB (2) | GB1422443A (en) |
| HK (1) | HK53480A (en) |
| HU (1) | HU164966B (en) |
| IE (1) | IE38148B1 (en) |
| IL (1) | IL41374A (en) |
| LU (1) | LU66876A1 (en) |
| NL (1) | NL178970C (en) |
| NO (1) | NO136978C (en) |
| PL (1) | PL83921B1 (en) |
| RO (1) | RO63566A (en) |
| SE (1) | SE395696B (en) |
| SU (1) | SU509237A3 (en) |
| YU (1) | YU36173B (en) |
| ZA (1) | ZA73494B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8377967B2 (en) | 2008-01-30 | 2013-02-19 | Nippon Zoki Pharmaceutical Co., Ltd. | Piperidine derivative |
| TWI457341B (en) * | 2008-08-01 | 2014-10-21 | Nippon Zoki Pharmaceutical Co | Aminopropyl derivative |
| JP5083989B2 (en) * | 2008-11-20 | 2012-11-28 | 日本臓器製薬株式会社 | Medicaments containing piperidine derivatives |
| CN104817532B (en) * | 2015-03-04 | 2017-07-25 | 浙江工业大学 | A kind of preparation method of the ketone of 10 methoxyl group 4H benzos [4,5] cycloheptatriene [1,2 b] thiazole 4 |
-
1972
- 1972-01-24 CH CH98572A patent/CH568312A5/xx not_active IP Right Cessation
-
1973
- 1973-01-12 FI FI89/73A patent/FI60396C/en active
- 1973-01-15 SE SE7300504A patent/SE395696B/en unknown
- 1973-01-16 NO NO185/73A patent/NO136978C/en unknown
- 1973-01-19 NL NLAANVRAGE7300797,A patent/NL178970C/en not_active IP Right Cessation
- 1973-01-19 FR FR7301856A patent/FR2169091B1/fr not_active Expired
- 1973-01-22 IE IE90/73A patent/IE38148B1/en unknown
- 1973-01-22 GB GB311973A patent/GB1422443A/en not_active Expired
- 1973-01-22 DE DE2302970A patent/DE2302970C3/en not_active Expired
- 1973-01-22 AT AT47873*#A patent/AT334897B/en not_active IP Right Cessation
- 1973-01-22 BE BE794370D patent/BE794370A/en not_active IP Right Cessation
- 1973-01-22 DD DD168384A patent/DD104084A5/xx unknown
- 1973-01-22 DE DE2366394A patent/DE2366394C1/en not_active Expired
- 1973-01-22 PL PL1973160372A patent/PL83921B1/pl unknown
- 1973-01-22 LU LU66876A patent/LU66876A1/xx unknown
- 1973-01-22 KR KR7300110A patent/KR780000049B1/en active
- 1973-01-22 CA CA161,801A patent/CA1006523A/en not_active Expired
- 1973-01-22 RO RO7300073573A patent/RO63566A/en unknown
- 1973-01-22 HU HUSA2446A patent/HU164966B/hu unknown
- 1973-01-22 GB GB2921475A patent/GB1422444A/en not_active Expired
- 1973-01-22 ES ES410855A patent/ES410855A1/en not_active Expired
- 1973-01-23 AU AU51378/73A patent/AU477308B2/en not_active Expired
- 1973-01-23 SU SU1874878A patent/SU509237A3/en active
- 1973-01-23 CS CS7300000503A patent/CS183674B2/en unknown
- 1973-01-23 ZA ZA730494A patent/ZA73494B/en unknown
- 1973-01-23 IL IL41374A patent/IL41374A/en unknown
- 1973-01-23 JP JP922773A patent/JPS566997B2/ja not_active Expired
- 1973-01-27 AR AR246230A patent/AR202094A1/en active
- 1973-04-22 YU YU178/73A patent/YU36173B/en unknown
-
1978
- 1978-10-04 FR FR7828336A patent/FR2401153A1/en active Granted
-
1980
- 1980-02-29 JP JP2420780A patent/JPS55129282A/en active Granted
- 1980-09-25 HK HK534/80A patent/HK53480A/en unknown
- 1980-12-29 DK DK555680A patent/DK154296C/en not_active IP Right Cessation
-
1990
- 1990-10-02 DK DK238090A patent/DK161324C/en not_active IP Right Cessation
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