GB1263035A - 0,4-methano and 1,4-ethano-tetrahydronaphthyloxypropanols - Google Patents
0,4-methano and 1,4-ethano-tetrahydronaphthyloxypropanolsInfo
- Publication number
- GB1263035A GB1263035A GB3555070A GB3555070A GB1263035A GB 1263035 A GB1263035 A GB 1263035A GB 3555070 A GB3555070 A GB 3555070A GB 3555070 A GB3555070 A GB 3555070A GB 1263035 A GB1263035 A GB 1263035A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- reacting
- hydrogen
- alkyl
- compounds
- 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
- UQSQJBFGRYKKQF-UHFFFAOYSA-N 1-(9-tricyclo[6.2.2.02,7]dodeca-2,4,6-trienyloxy)propan-1-ol Chemical class C12C(CC(C3=CC=CC=C13)CC2)OC(CC)O UQSQJBFGRYKKQF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- SKXPKKSFZJLRBT-UHFFFAOYSA-N 1-(1-tricyclo[6.2.2.02,7]dodeca-2,4,6-trienyloxy)propan-1-ol Chemical class C12(CCC(C3=CC=CC=C13)CC2)OC(CC)O SKXPKKSFZJLRBT-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000002924 oxiranes Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,263,035. 1,4-Methano and 1,4-ethano- 1,2,3,4-tetrahydronaphthyloxypropanols. CARLO ERBA S.p.A. 22 July, 1970 [30 July, 1969; 4 Feb., 1970], No. 35550/70. Heading C2C. Novel compounds of the general Formula I wherein each of the groups R and R<SP>1</SP>, which may be the same or different is a hydrogen or halogen atom or a C 1-4 alkyl, C 1-4 alkoxy, nitro, substituted or unsubstituted amino, C 1-6 alkanesulphonamido, C 1-6 -alkylthio, C 1-6 alkylsulphinyl or C 1-6 alkylsulphonyl group or R<SP>4</SP>R<SP>5</SP>NSO 2 wherein R<SP>4</SP> and R<SP>5</SP> which may be the same or different is a hydrogen or C 1-6 alkyl, or CH 3 (CH 2 ) n CONR<SP>6</SP>- wherein n is 0-6 and R<SP>6</SP> is a hydrogen or methyl; x is 1 or 2; R<SP>2</SP> is hydrogen, C 1-4 -alkyl or a benzyl group; R<SP>3</SP> is hydrogen, C 1-10 alkyl or a benzyl group, and pharmaceutically acceptable salts thereof may be prepared by (a) reacting a compound of the formula II or III where X is a halogen, with an amine HNR 2 R 3 ; (b) reacting a compound of the Formula IV with a compound XCH 2 CHOHCH 2 NR<SP>2</SP>R<SP>3</SP>; (d) catalytically reducing a compound I wherein R<SP>1</SP> is a nitro group to an amino group and optionally acylating to give a Compound I wherein R<SP>1</SP> is alkanesulphonamido or CH 3 (CH 2 ) n CONR<SP>6</SP>-; (e) reacting Compound I wherein R<SP>1</SP> is amino under reductive conditions with formaldehyde to give I wherein R<SP>1</SP> is -NHCH 3 ; (f) reacting a compound of the Formula VI with an amine HNR<SP>2</SP>R<SP>3</SP> and then reducing the reaction product; and optionally (g) reacting Compound I with an appropriate acid to give a pharmaceutically acceptable salt. Compounds II may be prepared by reacting a corresponding hydroxy compound IV with epichlorohydrin to introduce the epoxide side chain, which may in turn be hydrolysed to Compound III. Compounds VI may be prepared by reacting a sodium salt of IV with a 1,3-dihaloacetone. Substituents R 1 may be introduced into Compounds IV by nitration of IV where R 1 is H. Pharmaceutical compositions of Compound I with a carrier or diluent show #-adrenergic receptor blocking activity when administered parenterally.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2027869 | 1969-07-30 | ||
| IT2019370 | 1970-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1263035A true GB1263035A (en) | 1972-02-09 |
Family
ID=26327437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3555070A Expired GB1263035A (en) | 1969-07-30 | 1970-07-22 | 0,4-methano and 1,4-ethano-tetrahydronaphthyloxypropanols |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5010591B1 (en) |
| AT (1) | AT303700B (en) |
| BE (1) | BE753917A (en) |
| CH (1) | CH539017A (en) |
| CS (1) | CS163218B2 (en) |
| DE (1) | DE2037319C3 (en) |
| ES (1) | ES382297A1 (en) |
| FR (1) | FR2059580B1 (en) |
| GB (1) | GB1263035A (en) |
| IE (1) | IE34394B1 (en) |
| NL (1) | NL7011244A (en) |
| NO (1) | NO129042B (en) |
| SE (1) | SE368820B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436860A (en) * | 1972-12-18 | 1976-05-26 | Syntex Inc | 5,8-dihydro-5,8-methanonaphthalene cardiovascular agents |
-
1970
- 1970-07-17 IE IE93470A patent/IE34394B1/en unknown
- 1970-07-22 GB GB3555070A patent/GB1263035A/en not_active Expired
- 1970-07-24 BE BE753917D patent/BE753917A/en unknown
- 1970-07-27 AT AT685570A patent/AT303700B/en not_active IP Right Cessation
- 1970-07-28 DE DE19702037319 patent/DE2037319C3/en not_active Expired
- 1970-07-29 NO NO294470A patent/NO129042B/no unknown
- 1970-07-29 SE SE1040070A patent/SE368820B/xx unknown
- 1970-07-29 NL NL7011244A patent/NL7011244A/xx unknown
- 1970-07-29 ES ES382297A patent/ES382297A1/en not_active Expired
- 1970-07-30 CH CH1153170A patent/CH539017A/en not_active IP Right Cessation
- 1970-07-30 JP JP6646970A patent/JPS5010591B1/ja active Pending
- 1970-07-30 CS CS534870A patent/CS163218B2/cs unknown
- 1970-07-30 FR FR7028201A patent/FR2059580B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE34394L (en) | 1971-01-30 |
| DE2037319B2 (en) | 1973-04-26 |
| FR2059580A1 (en) | 1971-06-04 |
| DE2037319C3 (en) | 1973-11-22 |
| NL7011244A (en) | 1971-02-02 |
| CS163218B2 (en) | 1975-08-29 |
| IE34394B1 (en) | 1975-04-30 |
| DE2037319A1 (en) | 1971-02-11 |
| AT303700B (en) | 1972-12-11 |
| FR2059580B1 (en) | 1973-12-21 |
| BE753917A (en) | 1971-01-25 |
| NO129042B (en) | 1974-02-18 |
| JPS5010591B1 (en) | 1975-04-22 |
| SE368820B (en) | 1974-07-22 |
| ES382297A1 (en) | 1973-04-16 |
| CH539017A (en) | 1973-07-15 |
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