GB1460071A - Tetrahydronaphthyloxy-amines and related compounds - Google Patents
Tetrahydronaphthyloxy-amines and related compoundsInfo
- Publication number
- GB1460071A GB1460071A GB14974A GB14974A GB1460071A GB 1460071 A GB1460071 A GB 1460071A GB 14974 A GB14974 A GB 14974A GB 14974 A GB14974 A GB 14974A GB 1460071 A GB1460071 A GB 1460071A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydro
- naphthalene
- prepared
- naphthol
- phenoxyalkylamino
- 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 2
- CINNDRAMISOFMJ-UHFFFAOYSA-N o-(1,2,3,4-tetrahydronaphthalen-1-yl)hydroxylamine Chemical class C1=CC=C2C(ON)CCCC2=C1 CINNDRAMISOFMJ-UHFFFAOYSA-N 0.000 title 1
- VTIDEKZJKFOSDI-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)-1,2,3,4-tetrahydronaphthalene-2,3-diol Chemical compound O1C(COC2C(C(CC3=CC=CC=C23)O)O)C1 VTIDEKZJKFOSDI-UHFFFAOYSA-N 0.000 abstract 4
- OAHLLHJOPUWLKW-UHFFFAOYSA-N 5,8-dihydronaphthalen-1-ol Chemical compound C1C=CCC2=C1C=CC=C2O OAHLLHJOPUWLKW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- AUKZSCHMOAPNEN-NXEZZACHSA-N (6r,7r)-5,6,7,8-tetrahydronaphthalene-1,6,7-triol Chemical compound C1=CC(O)=C2C[C@@H](O)[C@H](O)CC2=C1 AUKZSCHMOAPNEN-NXEZZACHSA-N 0.000 abstract 1
- ZVYMFLOOXKNBBC-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1,2,3-triol Chemical compound C1(C(C(CC2=CC=CC=C12)O)O)O ZVYMFLOOXKNBBC-UHFFFAOYSA-N 0.000 abstract 1
- PBXHQVCPIWPYOZ-UHFFFAOYSA-N 1a,2,7,7a-tetrahydronaphtho[6,7-b]oxiren-3-ol Chemical compound C1C2OC2CC2=C1C=CC=C2O PBXHQVCPIWPYOZ-UHFFFAOYSA-N 0.000 abstract 1
- 206010012373 Depressed level of consciousness Diseases 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal alkoxide Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003839 salts 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
- C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/22—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one naphthalene or hydrogenated naphthalene ring system
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)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
Abstract
1460071 (3 - Phenoxyalkylamino - 2 - hydroxypropoxy) - 1,2,3,4 - tetrahydro - 2,3- naphthalene-diols E R SQUIBB & SONS Inc 2 Jan 1974 [11 Jan 1973] 00149/74 Heading C2C Novel (3-phenoxyalkylamino-2-hydroxypropoxy) - 1,2,3,4 - tetrahydro - 2,3 - naphthalenediols of the general Formula I and stereoisomers and acid addition and quaternary ammonium salts thereof, wherein each of R 11 and R 12 is a hydrogen or halogen atom or a C 1-8 alkyl, C 3-8 alkenyl, hydroxy, C 1-8 alkoxy, nitro, acyl, amino, acylamino, alkylamino or dialkylamino group and X is a straight or branched alkylene group having up to 6 carbon atoms in the linking chain, are prepared by reacting a (2,3 - epoxypropoxy) - 1,2,3,4 - tetrahydro - 2,3 - naphthalene - diol of the Formula II with a phenoxyalkylamine of the general Formula III followed optionally by salification of the product. (2,3 - Epoxypropoxy) - 1,2,3,4 - tetrahydro- 2,3 - naphthalene - diols (II) are prepared by reacting the corresponding hydroxy - 1,2,3,4- tetrahydro-2,3-naphthalene-diol with an alkali metal alkoxide and epichlorohydrin or epibromohydrin. cis - 5,6,7,8 - Tetrahydro - 1,6,7 - naphthalenetriol is prepared by hydroxylation of 5,8-dihydro-1-naphthol. trans - 5,6,7,8 - Tetrahydro - 1,6,7 - naphthalenetriol is prepared by epoxidation of 5,8- dihydro-1-naphthol, followed by treatment of the resulting 5,6,7,8 - tetrahydro - 6,7 - epoxy- 1-naphthol with perchloric acid. Pharmaceutical compositions, useful in treating CNS depression and hypertension and as antifibrillatory agents, comprise, as active ingredient, a compound (I) or physiologically acceptable acid addition salt thereof, together with a carrier therefor.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32283673A | 1973-01-11 | 1973-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1460071A true GB1460071A (en) | 1976-12-31 |
Family
ID=23256646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14974A Expired GB1460071A (en) | 1973-01-11 | 1974-01-02 | Tetrahydronaphthyloxy-amines and related compounds |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS49100069A (en) |
| CA (1) | CA994351A (en) |
| DE (1) | DE2401374A1 (en) |
| FR (1) | FR2213770A1 (en) |
| GB (1) | GB1460071A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029783A (en) * | 1973-08-03 | 1977-06-14 | Boehringer Mannheim G.M.B.H. | N-substituted 1-amino-3-phenoxy-propan-2-ol compounds and therapeutic compositions containing them |
| DE2962112D1 (en) * | 1978-02-08 | 1982-03-25 | Ici Plc | Alkanolamine derivatives, process for their preparation and pharmaceutical compositions containing them |
| US5254595A (en) * | 1988-12-23 | 1993-10-19 | Elf Sanofi | Aryloxypropanolaminotetralins, a process for their preparation and pharmaceutical compositions containing them |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5591776A (en) | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US6025361A (en) * | 1994-12-13 | 2000-02-15 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| CA2206287C (en) | 1994-12-13 | 2001-03-20 | Mark Chasin | Aryl thioxanthines |
| ATE247655T1 (en) | 1994-12-13 | 2003-09-15 | Euro Celtique Sa | TRIPLE SUBSTITUTED THIOXANTHINS |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| US6075016A (en) | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
-
1973
- 1973-12-27 CA CA188,991A patent/CA994351A/en not_active Expired
-
1974
- 1974-01-02 GB GB14974A patent/GB1460071A/en not_active Expired
- 1974-01-11 DE DE19742401374 patent/DE2401374A1/en active Pending
- 1974-01-11 FR FR7401042A patent/FR2213770A1/fr not_active Withdrawn
- 1974-01-11 JP JP49006959A patent/JPS49100069A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49100069A (en) | 1974-09-20 |
| CA994351A (en) | 1976-08-03 |
| DE2401374A1 (en) | 1974-07-18 |
| FR2213770A1 (en) | 1974-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |