GB1464695A - Dibenzo-b,c-pyrans and pharmaceutical compositions thereof - Google Patents
Dibenzo-b,c-pyrans and pharmaceutical compositions thereofInfo
- Publication number
- GB1464695A GB1464695A GB2606775A GB2606775A GB1464695A GB 1464695 A GB1464695 A GB 1464695A GB 2606775 A GB2606775 A GB 2606775A GB 2606775 A GB2606775 A GB 2606775A GB 1464695 A GB1464695 A GB 1464695A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- methyl
- ring
- alkyl
- ethyl
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 13
- 239000001257 hydrogen Substances 0.000 abstract 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 abstract 2
- PFDJPXDSJBDMCC-UHFFFAOYSA-N 2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CCCCC1=O PFDJPXDSJBDMCC-UHFFFAOYSA-N 0.000 abstract 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N resorcinol dimethyl ether Natural products COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 abstract 2
- -1 1,2 - Dimethyl - decyl Chemical group 0.000 abstract 1
- DNZBUOKXNWFRGN-UHFFFAOYSA-N 2-acetyl-5-ethylcyclohexan-1-one Chemical compound CCC1CCC(C(C)=O)C(=O)C1 DNZBUOKXNWFRGN-UHFFFAOYSA-N 0.000 abstract 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 abstract 1
- IEVRHAUJJJBXFH-UHFFFAOYSA-N 3-ethylcyclohexan-1-one Chemical compound CCC1CCCC(=O)C1 IEVRHAUJJJBXFH-UHFFFAOYSA-N 0.000 abstract 1
- PHHCCRIXTCENGL-UHFFFAOYSA-N 5-(3-methylundecan-2-yl)benzene-1,3-diol Chemical compound CCCCCCCCC(C)C(C)C1=CC(O)=CC(O)=C1 PHHCCRIXTCENGL-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- ICBRWQKLAOCTLD-UHFFFAOYSA-N bis(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)C=2C=C(OC)C=C(OC)C=2)=C1 ICBRWQKLAOCTLD-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 230000001335 demethylating effect Effects 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- FFVHHWOJYFCNJP-UHFFFAOYSA-N ethyl 4-methyl-2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(C)CC1=O FFVHHWOJYFCNJP-UHFFFAOYSA-N 0.000 abstract 1
- 230000027119 gastric acid secretion Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000004880 oxines Chemical class 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 238000009738 saturating Methods 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1464695 Dibenzo[b,d]pyrans and pharmaceutical compositions thereof SMITHKLINE CORP 19 June 1975 [24 June 1974] 26067/75 Heading C2C Novel compounds of the Formula I wherein ring A is a benzene ring, a cyclohexane ring or a cyclohexene ring with the double bond at position 6a-10a; R 1 is hydrogen, methyl or ethyl; R 2 is hydrogen or C 2-5 alkanoyl; R 3 is hydrogen, methyl or ethyl and R 4 and R 5 are hydrogen or methyl, at least one of R 3 , R 4 and R 5 being other than hydrogen; R 6 is C 4-3 alkyl and R 7 is hydrogen, methyl or ethyl, may be prepared (1) when A is a cyclohexene ring R 2 is hydrogen and R 7 is methyl or ethyl, by acid condensation of 2-acetyl or propionylcyclohexanone with a 5-alkyl resorcinol followed by reduction and acetylation to yield a compound I in which R 2 is acetyl optionally followed by hydrolysis to H at R 2 , (2) when A is a cyclohexene, R 2 is hydrogen and R 7 is hydrogen, by reduction of the corresponding pyrone and cyclizing the resulting 3<SP>1</SP>,4<SP>1</SP>,5<SP>1</SP>,6<SP>1</SP>-tetrahydro-2,6- dihydroxy - 2<SP>1 </SP>- hydroxymethyl - biphenyl; (3) when A is a benzene ring and R 2 is hydrogen by dehydrogenation of the corresponding cyclohexene ring; (4) when A is a benzene ring R 2 is hydrogen and R 7 is methyl or ethyl, heating the condensation product of 2-acetyl or propionyl cyclohexanone with a 5-alkyl resorcinol; (5) when A is cyclohexane and R 2 is hydrogen, reduction of the corresponding compound where A is cyclohexene; (6) when R 2 is alkanoyl esterifying the corresponding compound where R 2 is hydrogen. Various 5-alkyl resorcinols are prepared by reacting a 3,5-dimethoxyphenylketone or 3,5- dimethoxybenzaldehyde with an alkyl magnesium halide dehydrating the carbinol formed to yield a 5-alkenyl resorcinol dimethyl ether or a mixture of two such compounds, saturating the double bond to yield a 5-alkyl resorcinol dimethyl ether and demethylating the ether groups. 3 - (1,2 - Dimethyl - decyl) - 1 - hydroxy- 7,8,9,10 - tetrahydro - 9 - methyl - 6H - dibenzo- [b,d]pyrone is prepared by reacting 5-(1,2- dimethyldecyl) resorcinol and 5-methyl-2-carbethoxycyclohexanone in the presence of phosphorus oxychloride. 2 - Acetyl - 5 - ethylcyclohexanone is prepared by reacting 3-ethylcyclohexanone and acetylchloride in the presence of base. Pharmaceutical compositions of the compounds I with the usual excipients show depressant, sedative and tranquilizing activity and also analgesic, gastric acid secretion inhibitory and anti-inflammatory activity when administered internally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48253174A | 1974-06-24 | 1974-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1464695A true GB1464695A (en) | 1977-02-16 |
Family
ID=23916449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2606775A Expired GB1464695A (en) | 1974-06-24 | 1975-06-19 | Dibenzo-b,c-pyrans and pharmaceutical compositions thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1464695A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3141387A1 (en) * | 1980-10-20 | 1982-08-12 | Farmitalia Carlo Erba S.p.A., 20159 Milano | 6-SUBSTITUTED 6H-DIBENZO (B, D) PYRANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME |
| EP0048572A3 (en) * | 1980-09-19 | 1982-12-08 | Pfizer Inc. | Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof |
| EP0765160A4 (en) * | 1994-02-07 | 1997-04-09 |
-
1975
- 1975-06-19 GB GB2606775A patent/GB1464695A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0048572A3 (en) * | 1980-09-19 | 1982-12-08 | Pfizer Inc. | Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof |
| DE3141387A1 (en) * | 1980-10-20 | 1982-08-12 | Farmitalia Carlo Erba S.p.A., 20159 Milano | 6-SUBSTITUTED 6H-DIBENZO (B, D) PYRANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME |
| EP0765160A4 (en) * | 1994-02-07 | 1997-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |