GB1042634A - Diazepine and thiazepine compounds - Google Patents
Diazepine and thiazepine compoundsInfo
- Publication number
- GB1042634A GB1042634A GB20908/63A GB2090863A GB1042634A GB 1042634 A GB1042634 A GB 1042634A GB 20908/63 A GB20908/63 A GB 20908/63A GB 2090863 A GB2090863 A GB 2090863A GB 1042634 A GB1042634 A GB 1042634A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- groups
- hydrogen
- atoms
- group
- 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
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 title 1
- 150000004912 thiazepines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/14—[b, e]-condensed
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Compounds (some of which are novel) of the general formula <FORM:1042634/C2/1> (wherein -Z- represents -S-, -SO- or -(N-R6)-, R6 being hydrogen, a C1-5 alkyl or C2- 5 alkenyl group, R2 and R3, which may be the same or different, represent hydrogen atoms, C1- 5 alkyl, C2- 5 alkenyl or amino groups, mono-or di-alkylamino or mono- or di-alkylaminoalkyl groups in which the alkyl groups each contain 1-3 carbon atoms, or monocyclic aryl or aralkyl groups optionally substituted with halogen atoms or OH, CF3 or C1- 3 alkyl, alkoxy or alkymercapto groups, or R2 and R3 together with the adjacent nitrogen atom form a monocyclic alkyleneimino radical optionally containing further O-, S- or N-hetero-atoms, the last of which carries a hydrogen atom or an alkyl, hydroxyalkyl or alkoxyalkyl group of up to 3 carbon atoms, and R4 and R5, which may be the same or different, represent hydrogen or halogen atoms or OH, CF3 or C1- 3 alkyl, alkoxy or alkylmercapto groups) are prepared by (a) treating a reaction mixture containing nitrilium or imonium cations of the general formulae <FORM:1042634/C2/2> (wherein -Z- represents -S-, -SO- or -(N-R6)-, R6 being hydrogen, a C1- 5 alkyl or C2- 5 alkenyl group or a protecting group) with ammonia or an amine (R2NHR3), or (b) cyclizing an amide or thioamide of the general formula <FORM:1042634/C2/3> (wherein R represents S or O, and Z has the same meaning as Z1 in (a)), and in either case subsequently removing the protecting group R6 if present. When R2 and/or R3 in the products are hydrogen, they may be replaced by other R2/R3 values by the action of reactive esters of compounds R2OH or R3OH. Similarly an -NH- group as -Z- may be reacted with a reactive ester of R1OH. When -Z- is -S- it may be oxidized to -SO-. The bases obtained may be converted to acid addition salts or, when tertiary, to quaternary ammonium derivatives. Amides and thioamides of the last general formula above are prepared by reducing the corresponding nitro compounds.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH635062A CH416633A (en) | 1962-05-25 | 1962-05-25 | Process for the preparation of amidines |
| CH692162A CH476753A (en) | 1962-06-08 | 1962-06-08 | Process for the preparation of 11-basic substituted dibenzo (b, f) (1,4) thiazepines |
| CH1425162 | 1962-12-05 | ||
| CH1425362 | 1962-12-05 | ||
| CH190263 | 1963-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1042634A true GB1042634A (en) | 1966-09-14 |
Family
ID=27509014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20908/63A Expired GB1042634A (en) | 1962-05-25 | 1963-05-24 | Diazepine and thiazepine compounds |
Country Status (3)
| Country | Link |
|---|---|
| DE (4) | DE1470416A1 (en) |
| GB (1) | GB1042634A (en) |
| NL (1) | NL147426B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191760A (en) * | 1977-02-23 | 1980-03-04 | Abbott Laboratories | Dibenzodiazepines |
| AU2004308955B2 (en) * | 2003-12-22 | 2011-08-04 | Acadia Pharmaceuticals Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| RU2441867C2 (en) * | 2010-05-13 | 2012-02-10 | Общество С Ограниченной Ответственностью "Валентек" | DERIVATIVES OF 5H-DIBENZO[b, e][1, 4]DIAZEPINE AND ITS APPLICATION |
| US8158618B2 (en) | 2008-06-20 | 2012-04-17 | Astrazeneca Ab | Dibenzothiazepine derivatives and uses thereof—424 |
| WO2013070107A1 (en) * | 2011-11-09 | 2013-05-16 | Общество С Ограниченной Ответственностью "Валентек" | 5h-dibenzo[b,e][1,4]diazepine derivatives and use thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4341987C1 (en) * | 1993-12-09 | 1995-02-16 | Dresden Arzneimittel | Process for the preparation of clozapine |
| DE102004010830A1 (en) * | 2004-02-27 | 2005-09-15 | Bioagency Ag | Novel 1,4-benzooxazepane or 1,4-benzothiazepanes and derivatives |
| WO2007062336A2 (en) * | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Salt forms |
-
1963
- 1963-05-15 DE DE19631470416 patent/DE1470416A1/en active Pending
- 1963-05-15 DE DE19631620713 patent/DE1620713A1/en active Pending
- 1963-05-15 DE DE19631620712 patent/DE1620712A1/en active Pending
- 1963-05-15 DE DE19631620711 patent/DE1620711A1/en active Pending
- 1963-05-24 NL NL63293201A patent/NL147426B/en not_active IP Right Cessation
- 1963-05-24 GB GB20908/63A patent/GB1042634A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191760A (en) * | 1977-02-23 | 1980-03-04 | Abbott Laboratories | Dibenzodiazepines |
| AU2004308955B2 (en) * | 2003-12-22 | 2011-08-04 | Acadia Pharmaceuticals Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US8158618B2 (en) | 2008-06-20 | 2012-04-17 | Astrazeneca Ab | Dibenzothiazepine derivatives and uses thereof—424 |
| US8653257B2 (en) | 2008-06-20 | 2014-02-18 | Astrazeneca Ab | Dibenzothiazepine derivatives and uses thereof—424 |
| RU2441867C2 (en) * | 2010-05-13 | 2012-02-10 | Общество С Ограниченной Ответственностью "Валентек" | DERIVATIVES OF 5H-DIBENZO[b, e][1, 4]DIAZEPINE AND ITS APPLICATION |
| WO2013070107A1 (en) * | 2011-11-09 | 2013-05-16 | Общество С Ограниченной Ответственностью "Валентек" | 5h-dibenzo[b,e][1,4]diazepine derivatives and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620713A1 (en) | 1970-07-02 |
| DE1620711A1 (en) | 1970-06-04 |
| DE1470416A1 (en) | 1969-05-14 |
| NL147426B (en) | 1975-10-15 |
| DE1620712A1 (en) | 1970-06-04 |
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