JPS5817756B2 - ４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法 - Google Patents

４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法

Info

Publication number: JPS5817756B2
Authority: JP; Japan
Prior art keywords: formula; benzo; compound; cyclohepta; halogen
Prior art date: 1972-01-24
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

Application number

JP55175690A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57112390A (en

Inventor

ジヤン・ピエ−ル・ブ−ルクイン

グスタフ・シユワルブ

エルヴイン・ワルトフオ−ゲル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

Priority date (The priority date 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 date listed.)

1972-01-24

Filing date

1980-12-11

Publication date

1983-04-09

1980-12-11 Application filed by Sandoz AG filed Critical Sandoz AG

1982-07-13 Publication of JPS57112390A publication Critical patent/JPS57112390A/ja

1983-04-09 Publication of JPS5817756B2 publication Critical patent/JPS5817756B2/ja

Status Expired legal-status Critical Current

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
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 22
229910052736 halogen Chemical group 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000739 antihistaminic agent Substances 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
230000001387 anti-histamine Effects 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
231100000820 toxicity test Toxicity 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000001078 anti-cholinergic effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010040108 Serotonin syndrome Diseases 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D409/08—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 linked by a carbon chain containing alicyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

JP55175690A 1972-01-24 1980-12-11 ４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法 Expired JPS5817756B2 (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
CH98672A CH569012A5 (en)	1972-01-24	1972-01-24	4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors
CH992/72		1972-01-24
CH986/72		1972-01-24
CH990/72		1972-01-24
CH988/72		1972-01-24

Publications (2)

Publication Number	Publication Date
JPS57112390A JPS57112390A (en)	1982-07-13
JPS5817756B2 true JPS5817756B2 (ja)	1983-04-09

Family

ID=4199812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP55175690A Expired JPS5817756B2 (ja)	1972-01-24	1980-12-11	４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法

Country Status (6)

Country	Link
JP (1)	JPS5817756B2 (cs)
CH (1)	CH569012A5 (cs)
CS (1)	CS179977B2 (cs)
ES (1)	ES438598A1 (cs)
SE (1)	SE423712B (cs)
SU (1)	SU520914A3 (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS649343U (cs) *	1987-07-07	1989-01-19

1972
- 1972-01-24 CH CH98672A patent/CH569012A5/de not_active IP Right Cessation
1973
- 1973-01-23 CS CS7300000504A patent/CS179977B2/cs unknown
1974
- 1974-04-23 SU SU2017993A patent/SU520914A3/ru active
1975
- 1975-06-16 ES ES438598A patent/ES438598A1/es not_active Expired
1976
- 1976-01-13 SE SE7600275A patent/SE423712B/xx unknown
1980
- 1980-12-11 JP JP55175690A patent/JPS5817756B2/ja not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS649343U (cs) *	1987-07-07	1989-01-19

Also Published As

Publication number	Publication date
SU520914A3 (ru)	1976-07-05
AU5137773A (en)	1974-07-25
SE423712B (sv)	1982-05-24
JPS57112390A (en)	1982-07-13
CH569012A5 (en)	1975-11-14
SE7600275L (sv)	1976-01-13
ES438598A1 (es)	1977-05-16
CS179977B2 (en)	1977-12-30

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JPS5817756B2 - ４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (5)

Publications (2)

Family

ID=4199812

Family Applications (1)

Country Status (6)

Cited By (1)

Cited By (1)

Also Published As

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