GB943603A - Dibenzocycloheptane derivatives - Google Patents
Dibenzocycloheptane derivativesInfo
- Publication number
- GB943603A GB943603A GB11549/60A GB1154960A GB943603A GB 943603 A GB943603 A GB 943603A GB 11549/60 A GB11549/60 A GB 11549/60A GB 1154960 A GB1154960 A GB 1154960A GB 943603 A GB943603 A GB 943603A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- chloride
- nr3r4
- carbon atoms
- saturated
- 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
- 150000007654 dibenzocycloheptanes Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0943603/C2/1> (wherein X is ethylene or vinylene, R1 and R2 are hydrogen or halogen atoms or alkyl groups of at most 4 carbon atoms, Y is a straight or branched, saturated alkylene chain of at most 6 carbon atoms, which may be interrupted by an oxygen atom, and R3 and R4 are alkyl groups of at most 6 carbon atoms or together with the nitrogen atom represent a saturated, mononuclear 5- or 6-membered heterocyclic group which may include a second hetero atom, or R3 is an alkyl group and R4 an alkylene group linked to Y to form therewith, or part thereof, a saturated 5- or 6-membered heterocyclic group, or the grouping -Y-NR3R4 is a tropanyl radical) and acid-addition and quaternary ammonium salts thereof; and their preparation by reacting a compound of the formula: <FORM:0943603/C2/2> with a compound B-Y-NR3R4 (wherein one of A and B is a halogen atom and the other is -O-metal, or A is a halogen and B is a hydroxyl group) in the presence or absence of a solvent; or by heating a compound of the above general formula wherein A is hydroxyl with the compound HO-Y-NR3R4 in the presence of a dehydrating agent. Detailed examples are given. Dibenzo-(a,d)-1, 4-cycloheptadienyl-5-chloride is prepared from the 5-ol and hydrogen chloride or thionyl chloride. 3-Chloro-dibenzo-(a,d)-1, 4-cycloheptadien-5-chloride is prepared similarly. The dibenzocycloheptane derivatives of the invention, which are stated to have antihistaminic and similar actioities, may be made up into pharmaceutical compositions with suitable carriers. Specification 943,604 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL237664 | 1959-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB943603A true GB943603A (en) | 1963-12-04 |
Family
ID=19751644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11549/60A Expired GB943603A (en) | 1959-04-01 | 1960-04-01 | Dibenzocycloheptane derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3227716A (en) |
| CH (1) | CH417574A (en) |
| ES (1) | ES256994A1 (en) |
| GB (1) | GB943603A (en) |
| NL (1) | NL237664A (en) |
| OA (1) | OA00466A (en) |
| SE (2) | SE300617B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0350309A1 (en) * | 1988-07-08 | 1990-01-10 | Pfizer Limited | Piperidine derivatives |
| US5231104A (en) * | 1988-07-08 | 1993-07-27 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3369044A (en) * | 1962-07-23 | 1968-02-13 | Geigy Chem Corp | 5-carboxylic acid halide derivatives of 10, 11-dihydro-5h-dibenzo[a, d]cycloheptene |
| BE664608A (en) * | 1964-05-29 | |||
| GB1091910A (en) * | 1964-08-18 | 1967-11-22 | Koninklijke Pharma Fab Nv | New dibenzocycloheptenylamines |
| US3350405A (en) * | 1964-10-16 | 1967-10-31 | Sterling Drug Inc | Amino-lower-alkoxy-dibenzo [a, d] cyclohepten-5-ones and 10, 11-dihydro derivatives thereof |
| US3627832A (en) * | 1964-10-16 | 1971-12-14 | Sterling Drug Inc | AMINO-LOWER-ALKOXY-DIBENZO{8 a,d{9 CYCLOHEPTENES AND 5-ALKYL and -ARALKYL DERIVATIVES |
| FR176F (en) * | 1965-05-19 | |||
| US3317547A (en) * | 1965-06-24 | 1967-05-02 | Colgate Palmolive Co | Quinuclidyl ethers of dibenzocycloheptadiene |
| US3466291A (en) * | 1966-02-16 | 1969-09-09 | Sandoz Ag | 4(2-dialkylaminoethoxy or 2-piperidinoethoxy) - 9,10 - dihydro benzo(4,5)cyclohepta(1,2-b)thiophene derivatives |
| US4792551A (en) * | 1983-07-15 | 1988-12-20 | Syntex (U.S.A.) Inc. | 9-anthryloxyaminoalkanes and related compounds as anti-inflammatory and analgetic agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948732A (en) * | 1960-08-09 | N-heterocyclic compounds | ||
| US3014911A (en) * | 1958-09-29 | 1961-12-26 | Merck & Co Inc | Derivatives of dibenzo[a, e]cycloheptatriene |
-
0
- NL NL237664D patent/NL237664A/xx unknown
-
1960
- 1960-03-25 SE SE3012/60A patent/SE300617B/xx unknown
- 1960-03-29 CH CH351260A patent/CH417574A/en unknown
- 1960-03-31 ES ES0256994A patent/ES256994A1/en not_active Expired
- 1960-04-01 GB GB11549/60A patent/GB943603A/en not_active Expired
-
1963
- 1963-04-30 US US277014A patent/US3227716A/en not_active Expired - Lifetime
- 1963-08-05 SE SE2381/63A patent/SE307940B/xx unknown
-
1964
- 1964-11-03 OA OA50544A patent/OA00466A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0350309A1 (en) * | 1988-07-08 | 1990-01-10 | Pfizer Limited | Piperidine derivatives |
| US5089505A (en) * | 1988-07-08 | 1992-02-18 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
| US5231104A (en) * | 1988-07-08 | 1993-07-27 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
| US5410046A (en) * | 1988-07-08 | 1995-04-25 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
| US5534626A (en) * | 1988-07-08 | 1996-07-09 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
Also Published As
| Publication number | Publication date |
|---|---|
| OA00466A (en) | 1966-07-15 |
| ES256994A1 (en) | 1960-10-01 |
| US3227716A (en) | 1966-01-04 |
| SE300617B (en) | 1968-05-06 |
| NL237664A (en) | |
| CH417574A (en) | 1966-07-31 |
| SE307940B (en) | 1969-01-27 |
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