GB1086530A - 4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-amines - Google Patents
4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-aminesInfo
- Publication number
- GB1086530A GB1086530A GB2031565A GB2031565A GB1086530A GB 1086530 A GB1086530 A GB 1086530A GB 2031565 A GB2031565 A GB 2031565A GB 2031565 A GB2031565 A GB 2031565A GB 1086530 A GB1086530 A GB 1086530A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- bicyclo
- group
- octane
- amino
- 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
- -1 4-substituted phenyl bicyclo[2,2,2]octane-amines Chemical class 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- JXMVQBDHMBOHDH-UHFFFAOYSA-N exp-561 Chemical class C1CC(N)(CC2)CCC12C1=CC=CC=C1 JXMVQBDHMBOHDH-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- SJNOATVEVRKMBU-UHFFFAOYSA-N 1-hydroxy-4-phenylbicyclo[2.2.2]octan-3-one Chemical compound C1CC(O)(CC2=O)CCC12C1=CC=CC=C1 SJNOATVEVRKMBU-UHFFFAOYSA-N 0.000 abstract 1
- KKATZNUAUKDUIL-UHFFFAOYSA-N 1-phenylbicyclo[2.2.2]octan-4-ol Chemical compound C1CC(O)(CC2)CCC12C1=CC=CC=C1 KKATZNUAUKDUIL-UHFFFAOYSA-N 0.000 abstract 1
- SQHNZAVLCQLHKE-UHFFFAOYSA-N 1-phenylbicyclo[2.2.2]octane-4-carboxylic acid Chemical class C1CC(C(=O)O)(CC2)CCC12C1=CC=CC=C1 SQHNZAVLCQLHKE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- PVMFVLQZOMJUES-UHFFFAOYSA-N 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylic acid Chemical class C1(=CC=CC=C1)C12C=CC(CC1)(CC2)C(=O)O PVMFVLQZOMJUES-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 abstract 1
- 238000006105 Hofmann reaction Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006085 Schmidt reaction Methods 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 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
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR27260A FR5400M (enrdf_load_stackoverflow) | 1965-08-04 | 1965-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1086530A true GB1086530A (en) | 1967-10-11 |
Family
ID=8586041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2031565A Expired GB1086530A (en) | 1965-08-04 | 1965-05-13 | 4-phenyl and 4-substituted phenyl bicyclo[2,2,2]octane-amines |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR5400M (enrdf_load_stackoverflow) |
| GB (1) | GB1086530A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015077611A1 (en) | 2013-11-21 | 2015-05-28 | Marquette University | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
-
1965
- 1965-05-13 GB GB2031565A patent/GB1086530A/en not_active Expired
- 1965-08-04 FR FR27260A patent/FR5400M/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015077611A1 (en) | 2013-11-21 | 2015-05-28 | Marquette University | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
| JP2017504567A (ja) * | 2013-11-21 | 2017-02-09 | マーケット ユニバーシティー | エストロゲン受容体ベータアイソフォームの選択的アゴニストとしての置換（４’−ヒドロキシフェニル）シクロアルカン化合物およびその使用 |
| AU2014352830B2 (en) * | 2013-11-21 | 2018-12-13 | Concordia University, Inc. | Substituted (4'-hydroxyphenyl)cycloalkane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
| US10570077B2 (en) | 2013-11-21 | 2020-02-25 | Marquette University | Substituted (4'-hydroxyphenyl)cyclohexane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform |
Also Published As
| Publication number | Publication date |
|---|---|
| FR5400M (enrdf_load_stackoverflow) | 1967-09-25 |
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