GB1195752A - Xanthene and Thioxanthene Derivatives - Google Patents
Xanthene and Thioxanthene DerivativesInfo
- Publication number
- GB1195752A GB1195752A GB133868A GB133868A GB1195752A GB 1195752 A GB1195752 A GB 1195752A GB 133868 A GB133868 A GB 133868A GB 133868 A GB133868 A GB 133868A GB 1195752 A GB1195752 A GB 1195752A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- thiaxanthenone
- compounds
- alkyl
- acid
- 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
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 title 1
- 229940054058 antipsychotic thioxanthene derivative Drugs 0.000 title 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 title 1
- 150000005075 thioxanthenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- BNLRKUSVMCIOGU-UHFFFAOYSA-N 1-hydroxyxanthen-9-one Chemical compound O1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BNLRKUSVMCIOGU-UHFFFAOYSA-N 0.000 abstract 2
- GSISQERZCQNSAJ-UHFFFAOYSA-N 10-oxophenoxathiin-3-ol Chemical compound OC=1C=CC=2S(C3=CC=CC=C3OC2C1)=O GSISQERZCQNSAJ-UHFFFAOYSA-N 0.000 abstract 2
- -1 3- Hydroxy - 9 - thiaxanthenone - 10,10 - dioxide Chemical compound 0.000 abstract 2
- NRWDFTLUVMRZLW-UHFFFAOYSA-N 3-methoxyphenoxathiine 10-oxide Chemical compound COC=1C=CC=2S(C3=CC=CC=C3OC2C1)=O NRWDFTLUVMRZLW-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 229910005965 SO 2 Inorganic materials 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 abstract 2
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 abstract 1
- YHLRNFKMGIVVMP-UHFFFAOYSA-N 10-benzyl-10-hydroxy-3-methoxyphenoxathiine Chemical compound COC=1C=CC=2S(C3=CC=CC=C3OC2C1)(O)CC1=CC=CC=C1 YHLRNFKMGIVVMP-UHFFFAOYSA-N 0.000 abstract 1
- ZSSSTYPBCWPUNP-UHFFFAOYSA-N 10-benzylthiopyrano[3,2-b]chromen-3-ol Chemical compound OC1=CSC2=C(C3=CC=CC=C3OC2=C1)CC1=CC=CC=C1 ZSSSTYPBCWPUNP-UHFFFAOYSA-N 0.000 abstract 1
- XVWFRODMSLQQLR-UHFFFAOYSA-N 10-oxophenoxathiin-2-ol Chemical compound OC1=CC=2S(C3=CC=CC=C3OC2C=C1)=O XVWFRODMSLQQLR-UHFFFAOYSA-N 0.000 abstract 1
- XWKUKQISOJLWCY-UHFFFAOYSA-N 3-(4-chlorobutoxy)phenoxathiine 10-oxide Chemical group ClCCCCOC=1C=CC=2S(C3=CC=CC=C3OC2C1)=O XWKUKQISOJLWCY-UHFFFAOYSA-N 0.000 abstract 1
- LNTAOTZQZXBKRN-UHFFFAOYSA-N 9-benzyl-9H-xanthen-1-ol Chemical compound OC1=CC=CC=2OC3=CC=CC=C3C(C12)CC1=CC=CC=C1 LNTAOTZQZXBKRN-UHFFFAOYSA-N 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient 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
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 229940127219 anticoagulant drug Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- 239000003218 coronary vasodilator agent Substances 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 abstract 1
- 229960002456 hexobarbital Drugs 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 150000003732 xanthenes Chemical class 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
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- 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
- C07D311/82—Xanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61505867A | 1967-02-10 | 1967-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1195752A true GB1195752A (en) | 1970-06-24 |
Family
ID=24463820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB133868A Expired GB1195752A (en) | 1967-02-10 | 1968-01-09 | Xanthene and Thioxanthene Derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE710423A (enrdf_load_stackoverflow) |
| CH (2) | CH546757A (enrdf_load_stackoverflow) |
| DE (1) | DE1668974A1 (enrdf_load_stackoverflow) |
| FR (1) | FR8379M (enrdf_load_stackoverflow) |
| GB (1) | GB1195752A (enrdf_load_stackoverflow) |
| NL (2) | NL6801093A (enrdf_load_stackoverflow) |
| SE (1) | SE352355B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106810532A (zh) * | 2016-12-20 | 2017-06-09 | 四川大学 | 一类胺烷氧基噻吨酮类化合物、其制备方法和用途 |
-
1968
- 1968-01-09 GB GB133868A patent/GB1195752A/en not_active Expired
- 1968-01-24 FR FR137212A patent/FR8379M/fr not_active Expired
- 1968-01-24 NL NL6801093A patent/NL6801093A/xx unknown
- 1968-02-05 SE SE147468A patent/SE352355B/xx unknown
- 1968-02-05 CH CH182871A patent/CH546757A/xx not_active IP Right Cessation
- 1968-02-05 DE DE19681668974 patent/DE1668974A1/de active Pending
- 1968-02-05 CH CH165168A patent/CH513151A/de not_active IP Right Cessation
- 1968-02-07 BE BE710423D patent/BE710423A/xx unknown
-
1972
- 1972-03-10 NL NL7203258A patent/NL7203258A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106810532A (zh) * | 2016-12-20 | 2017-06-09 | 四川大学 | 一类胺烷氧基噻吨酮类化合物、其制备方法和用途 |
| CN106810532B (zh) * | 2016-12-20 | 2019-03-15 | 四川大学 | 一类胺烷氧基噻吨酮类化合物、其制备方法和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6801093A (enrdf_load_stackoverflow) | 1968-08-12 |
| SE352355B (enrdf_load_stackoverflow) | 1972-12-27 |
| DE1668974A1 (de) | 1971-09-23 |
| NL7203258A (enrdf_load_stackoverflow) | 1972-06-26 |
| CH546757A (de) | 1974-03-15 |
| CH513151A (de) | 1971-09-30 |
| BE710423A (enrdf_load_stackoverflow) | 1968-08-07 |
| FR8379M (enrdf_load_stackoverflow) | 1971-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |