GB1307645A - Benzopyran-5-ols and coumarin intermediates therefor - Google Patents
Benzopyran-5-ols and coumarin intermediates thereforInfo
- Publication number
- GB1307645A GB1307645A GB4668270A GB4668270A GB1307645A GB 1307645 A GB1307645 A GB 1307645A GB 4668270 A GB4668270 A GB 4668270A GB 4668270 A GB4668270 A GB 4668270A GB 1307645 A GB1307645 A GB 1307645A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- group
- piperidinyl
- oct
- pharmaceutically acceptable
- 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
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title abstract 3
- 229960000956 coumarin Drugs 0.000 title abstract 2
- 235000001671 coumarin Nutrition 0.000 title abstract 2
- UNVNVCMGCFNMQD-UHFFFAOYSA-N 2h-chromen-5-ol Chemical class O1CC=CC2=C1C=CC=C2O UNVNVCMGCFNMQD-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001204 N-oxides Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- IRMPFYJSHJGOPE-UHFFFAOYSA-N olivetol Chemical compound CCCCCC1=CC(O)=CC(O)=C1 IRMPFYJSHJGOPE-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- RSIRDUFVJCRFBP-UHFFFAOYSA-N 1-(2H-chromen-2-yl)piperidine Chemical class N1(CCCCC1)C1OC2=C(C=C1)C=CC=C2 RSIRDUFVJCRFBP-UHFFFAOYSA-N 0.000 abstract 1
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1307645 Piperidinyl-benzopyran derivatives BEECHAM GROUP Ltd 1 Oct 1970 [31 Oct 1969] 46682/70 Heading C2C Novel compounds of Formula (I): wherein R 1 is a C 1-6 alkyl group, R 2 is a C 1-20 aliphatic hydrocarbon group, R 3 is H, a C 1-12 hydrocarbon or an acyl-group COR 4 , where R 4 is a C 1-12 hydrocarbon group, and pharmaceutically acceptable salts, N-oxides, esters and ethers, may be obtained by reacting a chromanone (II): with a Grignard reagent R 1 MgY, where Y is Br, Cl, or I, to yield a compound (Ia), and optionally converting to other products of Formula (I) by acylation or hydrocarbonylation, or forming an N-oxide, ester, ether or salt. An intermediate, 4-(1-benzoyl-4-piperidinyl) - 5 - hydroxy - 7 - pentyl coumarin is obtained by reaction of ethyl #-oxo-4-piperidine-N- benzoyl propionate and olivetol with cone sulphuric acid and phosphorus oxychloride. Pharmaceutical compositions, useful as antidepressants, anti-anxiety agents, hypotensives and analgesics, comprise compounds of Formula (I) together with a pharmaceutically acceptable carrier in forms suitable for. oral or parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87307969A | 1969-10-31 | 1969-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1307645A true GB1307645A (en) | 1973-02-21 |
Family
ID=25360940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4668270A Expired GB1307645A (en) | 1969-10-31 | 1970-10-01 | Benzopyran-5-ols and coumarin intermediates therefor |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE758328A (en) |
| DE (1) | DE2053405A1 (en) |
| FR (1) | FR2070183B1 (en) |
| GB (1) | GB1307645A (en) |
| ZA (1) | ZA706818B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794630A (en) * | 1972-01-26 | 1973-07-26 | Beecham Group Ltd | ANTI-HYPERTENSIVE POLYCYCLIC COMPOUNDS |
| FR2189027B1 (en) * | 1972-06-21 | 1976-03-05 | Leurquin Laboratoires Fr |
-
0
- BE BE758328D patent/BE758328A/en unknown
-
1970
- 1970-10-01 GB GB4668270A patent/GB1307645A/en not_active Expired
- 1970-10-07 ZA ZA706818A patent/ZA706818B/en unknown
- 1970-10-30 FR FR7039170A patent/FR2070183B1/fr not_active Expired
- 1970-10-30 DE DE19702053405 patent/DE2053405A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2070183A1 (en) | 1971-09-10 |
| ZA706818B (en) | 1971-07-28 |
| BE758328A (en) | 1971-04-30 |
| DE2053405A1 (en) | 1971-05-06 |
| FR2070183B1 (en) | 1974-10-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |