GB1195729A - Azabicycloaliphatic Compounds - Google Patents
Azabicycloaliphatic CompoundsInfo
- Publication number
- GB1195729A GB1195729A GB33851/67A GB3385167A GB1195729A GB 1195729 A GB1195729 A GB 1195729A GB 33851/67 A GB33851/67 A GB 33851/67A GB 3385167 A GB3385167 A GB 3385167A GB 1195729 A GB1195729 A GB 1195729A
- Authority
- GB
- United Kingdom
- Prior art keywords
- het
- compounds
- group
- alk
- aza
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 239000000543 intermediate Substances 0.000 abstract 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 abstract 1
- ZJESVHHCOLPPSX-UHFFFAOYSA-N 4-(3-azabicyclo[3.2.2]nonan-3-yl)-3-methylbutanenitrile hydrochloride Chemical compound Cl.C(#N)CC(CN1CC2CCC(C1)CC2)C ZJESVHHCOLPPSX-UHFFFAOYSA-N 0.000 abstract 1
- ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XHGXOJSSKMNLAA-UHFFFAOYSA-N Cl.C(#N)CCCCN1CC2CCC(C1)CC2 Chemical compound Cl.C(#N)CCCCN1CC2CCC(C1)CC2 XHGXOJSSKMNLAA-UHFFFAOYSA-N 0.000 abstract 1
- XWGUKRSIZIMSLT-UHFFFAOYSA-N Cl.C(#N)CCCN1CC2CCC(C1)CC2 Chemical compound Cl.C(#N)CCCN1CC2CCC(C1)CC2 XWGUKRSIZIMSLT-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 230000002908 adrenolytic effect Effects 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 150000001455 metallic ions Chemical class 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Abstract
1,195,729. Azabicycloaliphatic compounds. CIBA Ltd. 24 July, 1967 [27 July, 1966; 6 June, 1967], No. 33851/67. Heading C2C. Novel compounds of Formula I in which Ar is a substituted or unsubstituted phenyl or a substituted or unsubstituted monocyclic monoheterocyclic group of aromatic character; X is O or a free, etherified or esterified OH together with a H atom or a hydrocarbon radical; Alk is C 1-7 alkylene which separates Het and C=X by at least 3C; and Het is a bicycloalkyleneamino group having 6-10C as ring or bridge members, which carbon atoms may be linked by one or more double bonds or substituted by C 1-7 alkyl groups, and having only one ring N atom are prepared (a) by reacting a reactive ester of Ar-C(=X)-Alk- OH with H-Het, or (b) by reacting Ar-Y with Z-Alk-Het, one of Y and Z being a positively charged metallic ion and the other a functionally modified carboxyl group capable of reacting with the metal ion and where desired converting a compound with a carbonyl group into the carbinol group followed by esterification or etherification. Intermediates isolated are 3-(3-cyanopropyl)-3- aza - bicyclo - [3,2,2] - nonane hydrochloride prepared from γ-chloro-butyronitrile and 3-azabicyclo - [3,2,2] - nonane; 3 - (4 - cyanobutyl)- 3 - aza - bicyclo - [3,2,2] - nonane hydrochloride and 3 - (3 - cyano - 2 - methyl - 1 - propyl) - 3- aza - bicyclo - [3,2,2] - nonane hydrochloride, the latter two being prepared in a similar manner to the first-named intermediate. Pharmaceutical compositions comprise a compound I in conjunction with a suitable carrier or diluent and are administered enterally and parenterally. The compounds I exhibit adrenolytic, antihypertensive, sedative-tranquillizing and anti-agressive properties.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1673568A CH486463A (en) | 1966-07-27 | 1966-07-27 | Process for the preparation of new azabicycloaliphatic compounds |
| CH1088966A CH508626A (en) | 1966-07-27 | 1966-07-27 | Process for the preparation of new azabicycloaliphatic compounds |
| CH1673468A CH507947A (en) | 1966-07-27 | 1966-07-27 | Azabicycloaliphatic cpds - trianquillisers adrenolytic and hypertensive agents |
| CH799267 | 1967-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1195729A true GB1195729A (en) | 1970-06-24 |
Family
ID=27429116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33851/67A Expired GB1195729A (en) | 1966-07-27 | 1967-07-24 | Azabicycloaliphatic Compounds |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE701861A (en) |
| CH (3) | CH507947A (en) |
| DE (1) | DE1670448B2 (en) |
| FR (2) | FR1549235A (en) |
| GB (1) | GB1195729A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007503A1 (en) * | 1988-12-23 | 1990-07-12 | Boehringer Ingelheim Kg | Substituted 3-azabicyclo[3.1.1]heptanes, their production and use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2365258A1 (en) | 1999-05-04 | 2000-11-09 | Neurosearch A/S | Heteroaryl diazabicycloalkanes, their preparation and use |
-
1966
- 1966-07-27 CH CH1673468A patent/CH507947A/en not_active IP Right Cessation
- 1966-07-27 CH CH1673568A patent/CH486463A/en not_active IP Right Cessation
- 1966-07-27 CH CH1088966A patent/CH508626A/en not_active IP Right Cessation
-
1967
- 1967-07-19 DE DE1967C0042904 patent/DE1670448B2/en active Granted
- 1967-07-20 FR FR1549235D patent/FR1549235A/fr not_active Expired
- 1967-07-24 GB GB33851/67A patent/GB1195729A/en not_active Expired
- 1967-07-26 BE BE701861D patent/BE701861A/xx unknown
- 1967-10-12 FR FR124194A patent/FR7074M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007503A1 (en) * | 1988-12-23 | 1990-07-12 | Boehringer Ingelheim Kg | Substituted 3-azabicyclo[3.1.1]heptanes, their production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| CH486463A (en) | 1970-02-28 |
| CH508626A (en) | 1971-06-15 |
| FR1549235A (en) | 1968-12-13 |
| FR7074M (en) | 1969-06-30 |
| DE1670448A1 (en) | 1971-02-11 |
| CH507947A (en) | 1971-05-31 |
| BE701861A (en) | 1968-01-26 |
| DE1670448B2 (en) | 1976-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE | Patent expired |