GB1489486A - Esters of thienobenzopyrans and thiopyrano benzopyrans - Google Patents
Esters of thienobenzopyrans and thiopyrano benzopyransInfo
- Publication number
- GB1489486A GB1489486A GB9212/75A GB921275A GB1489486A GB 1489486 A GB1489486 A GB 1489486A GB 9212/75 A GB9212/75 A GB 9212/75A GB 921275 A GB921275 A GB 921275A GB 1489486 A GB1489486 A GB 1489486A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- alkyl
- prepared
- ethyl
- carboxylate
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- 150000001562 benzopyrans Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 abstract 1
- QLIWGYUAFYGLHL-UHFFFAOYSA-N 2,2-dimethyl-4-piperidin-1-ylbutanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(C)(C)CCN1CCCCC1 QLIWGYUAFYGLHL-UHFFFAOYSA-N 0.000 abstract 1
- QSSIMUKDLXLOMB-UHFFFAOYSA-N 2-methyl-4-piperidin-1-ylbutanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(C)CCN1CCCCC1 QSSIMUKDLXLOMB-UHFFFAOYSA-N 0.000 abstract 1
- KJWTZUBBBRWVLN-UHFFFAOYSA-N 2h-thieno[2,3-h]chromene Chemical compound C1=CCOC2=C1C=CC1=C2C=CS1 KJWTZUBBBRWVLN-UHFFFAOYSA-N 0.000 abstract 1
- UPVAIJPDWVTFKT-UHFFFAOYSA-N 3,3-dimethyloxolan-2-one Chemical compound CC1(C)CCOC1=O UPVAIJPDWVTFKT-UHFFFAOYSA-N 0.000 abstract 1
- GHIWHMXQYRIHIA-UHFFFAOYSA-N 3-oxothiane-2-carboxylic acid Chemical class OC(=O)C1SCCCC1=O GHIWHMXQYRIHIA-UHFFFAOYSA-N 0.000 abstract 1
- VPODRFQIKWFWJW-UHFFFAOYSA-N 3-oxothiolane-2-carboxylic acid Chemical class OC(=O)C1SCCC1=O VPODRFQIKWFWJW-UHFFFAOYSA-N 0.000 abstract 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 abstract 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000000049 anti-anxiety effect Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000000561 anti-psychotic effect Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 150000007942 carboxylates Chemical group 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- ITGFPAPRIJHPRD-UHFFFAOYSA-N ethyl 2,2-dimethyl-4-piperidin-1-ylbutanoate Chemical compound CCOC(=O)C(C)(C)CCN1CCCCC1 ITGFPAPRIJHPRD-UHFFFAOYSA-N 0.000 abstract 1
- BATCSNGUUOOSBY-UHFFFAOYSA-N ethyl 2-methyl-4-piperidin-1-ylbutanoate Chemical compound CCOC(=O)C(C)CCN1CCCCC1 BATCSNGUUOOSBY-UHFFFAOYSA-N 0.000 abstract 1
- RAFZDWOTKJPFNY-UHFFFAOYSA-N ethyl 4-bromo-2,2-dimethylbutanoate Chemical compound CCOC(=O)C(C)(C)CCBr RAFZDWOTKJPFNY-UHFFFAOYSA-N 0.000 abstract 1
- DVSXBIBNHUXLRW-UHFFFAOYSA-N ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylate Chemical compound CCOC(=O)C1SC(C)(C)CC1=O DVSXBIBNHUXLRW-UHFFFAOYSA-N 0.000 abstract 1
- VPHHCVUUKHWFPW-UHFFFAOYSA-N ethyl 5-methyl-3-oxothiolane-2-carboxylate Chemical compound CCOC(=O)C1SC(C)CC1=O VPHHCVUUKHWFPW-UHFFFAOYSA-N 0.000 abstract 1
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 abstract 1
- PVFTYUXVJKUISC-UHFFFAOYSA-N methyl 4-bromo-2-methylbutanoate Chemical compound COC(=O)C(C)CCBr PVFTYUXVJKUISC-UHFFFAOYSA-N 0.000 abstract 1
- JVQSWTRSPLEMBB-UHFFFAOYSA-N methyl 4-methyl-3-oxothiane-2-carboxylate Chemical compound COC(=O)C1SCCC(C)C1=O JVQSWTRSPLEMBB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- -1 tranquillizing Substances 0.000 abstract 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/448,401 US3960871A (en) | 1971-12-27 | 1974-03-05 | Esters of thienobenzopyrans and thiopyranobenzopyrans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1489486A true GB1489486A (en) | 1977-10-19 |
Family
ID=23780170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9212/75A Expired GB1489486A (en) | 1974-03-05 | 1975-03-05 | Esters of thienobenzopyrans and thiopyrano benzopyrans |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2509562A1 (enExample) |
| FR (1) | FR2262980B2 (enExample) |
| GB (1) | GB1489486A (enExample) |
| SE (1) | SE422687B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2143234A (en) * | 1983-07-06 | 1985-02-06 | Shinogi Seiyaku Kabushiki Kais | (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives |
-
1975
- 1975-03-04 SE SE7502409A patent/SE422687B/xx unknown
- 1975-03-04 FR FR7506752A patent/FR2262980B2/fr not_active Expired
- 1975-03-05 DE DE19752509562 patent/DE2509562A1/de not_active Ceased
- 1975-03-05 GB GB9212/75A patent/GB1489486A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2143234A (en) * | 1983-07-06 | 1985-02-06 | Shinogi Seiyaku Kabushiki Kais | (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| SE422687B (sv) | 1982-03-22 |
| SE7502409L (enExample) | 1975-09-08 |
| DE2509562A1 (de) | 1975-09-11 |
| FR2262980B2 (enExample) | 1982-07-16 |
| FR2262980A2 (enExample) | 1975-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |