GB1447032A - Tricyclic sulphones and pharmaceutical compositions containing them - Google Patents
Tricyclic sulphones and pharmaceutical compositions containing themInfo
- Publication number
- GB1447032A GB1447032A GB1955276A GB1955276A GB1447032A GB 1447032 A GB1447032 A GB 1447032A GB 1955276 A GB1955276 A GB 1955276A GB 1955276 A GB1955276 A GB 1955276A GB 1447032 A GB1447032 A GB 1447032A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dioxide
- prep
- acid
- formula
- compound
- 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 2
- 125000001174 sulfone group Chemical group 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 12
- 239000002253 acid Substances 0.000 abstract 6
- -1 carboxylate salt Chemical class 0.000 abstract 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 5
- KTMTUGYSHWKLNN-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 KTMTUGYSHWKLNN-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- UPLKJVHYACNBJJ-UHFFFAOYSA-N 2-nitrobenzene-1,4-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC=C1C#N UPLKJVHYACNBJJ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- KZJDSILKHOJSFN-UHFFFAOYSA-N 1-(8-acetylphenoxathiin-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=C2SC3=CC(C(=O)C)=CC=C3OC2=C1 KZJDSILKHOJSFN-UHFFFAOYSA-N 0.000 abstract 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 abstract 1
- NTHRMQKFNGUJPH-UHFFFAOYSA-N 1-dibenzothiophen-2-ylethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3SC2=C1 NTHRMQKFNGUJPH-UHFFFAOYSA-N 0.000 abstract 1
- QZKVUSSYPPWURQ-UHFFFAOYSA-N 1-methylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C QZKVUSSYPPWURQ-UHFFFAOYSA-N 0.000 abstract 1
- NQDUNKLNHWXHTK-UHFFFAOYSA-N 10,10-dioxo-9h-thioxanthene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3CC2=C1 NQDUNKLNHWXHTK-UHFFFAOYSA-N 0.000 abstract 1
- QHUAUSFRANDNBC-UHFFFAOYSA-N 10,10-dioxophenoxathiine-2,8-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 QHUAUSFRANDNBC-UHFFFAOYSA-N 0.000 abstract 1
- ITTPKTWJMJMKEW-UHFFFAOYSA-N 10,10-dioxothianthrene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3SC2=C1 ITTPKTWJMJMKEW-UHFFFAOYSA-N 0.000 abstract 1
- FNLBYUMDLZWDPC-UHFFFAOYSA-N 2,8-dimethylphenoxathiine Chemical compound C1=C(C)C=C2SC3=CC(C)=CC=C3OC2=C1 FNLBYUMDLZWDPC-UHFFFAOYSA-N 0.000 abstract 1
- LJUNPOOBVPLELA-UHFFFAOYSA-N 2,8-dimethylphenoxathiine 10,10-dioxide Chemical compound C1=C(C)C=C2S(=O)(=O)C3=CC(C)=CC=C3OC2=C1 LJUNPOOBVPLELA-UHFFFAOYSA-N 0.000 abstract 1
- KRUGNXCISKYWRU-UHFFFAOYSA-N 2-(4-tert-butylphenyl)sulfanylterephthalic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1SC1=CC(C(O)=O)=CC=C1C(O)=O KRUGNXCISKYWRU-UHFFFAOYSA-N 0.000 abstract 1
- WOTFCARJUHUAST-UHFFFAOYSA-N 2-(benzenesulfonyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(S(=O)(=O)C=2C=CC=CC=2)=C1 WOTFCARJUHUAST-UHFFFAOYSA-N 0.000 abstract 1
- FGZVMJXJXIZLHA-UHFFFAOYSA-N 2-(benzenesulfonyl)-4-chlorocyclohexa-1,5-diene-1,4-dicarboxylic acid Chemical compound C1C(Cl)(C(O)=O)C=CC(C(=O)O)=C1S(=O)(=O)C1=CC=CC=C1 FGZVMJXJXIZLHA-UHFFFAOYSA-N 0.000 abstract 1
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-UHFFFAOYSA-N 0.000 abstract 1
- NOYRFDHEJYWIHG-UHFFFAOYSA-N 2-methoxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(OC)=CC=C3SC2=C1 NOYRFDHEJYWIHG-UHFFFAOYSA-N 0.000 abstract 1
- LFCIPFQOPWQEPF-UHFFFAOYSA-N 2-tert-butylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3SC2=C1 LFCIPFQOPWQEPF-UHFFFAOYSA-N 0.000 abstract 1
- YPRJLDUOGDQQAK-UHFFFAOYSA-N 3-nitrodibenzothiophene 5,5-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 YPRJLDUOGDQQAK-UHFFFAOYSA-N 0.000 abstract 1
- ZIYILGYCQDBDIZ-UHFFFAOYSA-N 4-chloro-2-phenylsulfanylcyclohexa-1,5-diene-1,4-dicarbonitrile Chemical compound C1=CC(Cl)(C#N)CC(SC=2C=CC=CC=2)=C1C#N ZIYILGYCQDBDIZ-UHFFFAOYSA-N 0.000 abstract 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 abstract 1
- WWQQPHUHTAZWDH-UHFFFAOYSA-N 4-ethylbenzenethiol Chemical compound CCC1=CC=C(S)C=C1 WWQQPHUHTAZWDH-UHFFFAOYSA-N 0.000 abstract 1
- HFVXBJQSKOPSEL-UHFFFAOYSA-N 4-nitro-2-thiophen-2-yloxycyclohexa-1,5-diene-1,4-dicarboxylic acid Chemical compound C1C([N+]([O-])=O)(C(O)=O)C=CC(C(=O)O)=C1OC1=CC=CS1 HFVXBJQSKOPSEL-UHFFFAOYSA-N 0.000 abstract 1
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 abstract 1
- HGDUVWDPTRPPGD-UHFFFAOYSA-N 5,10,10-trioxothianthrene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)C3=CC=C(C(=O)O)C=C3S(=O)(=O)C2=C1 HGDUVWDPTRPPGD-UHFFFAOYSA-N 0.000 abstract 1
- RHWPUKCISLOMRK-UHFFFAOYSA-N 5,5-dioxodibenzothiophen-3-amine Chemical compound C1=CC=C2S(=O)(=O)C3=CC(N)=CC=C3C2=C1 RHWPUKCISLOMRK-UHFFFAOYSA-N 0.000 abstract 1
- MBJFRYCYPNBYRB-UHFFFAOYSA-N 5,5-dioxodibenzothiophene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C2=C1 MBJFRYCYPNBYRB-UHFFFAOYSA-N 0.000 abstract 1
- NVPMSGXNAYNXQC-UHFFFAOYSA-N 5,5-dioxodibenzothiophene-3-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3C2=C1 NVPMSGXNAYNXQC-UHFFFAOYSA-N 0.000 abstract 1
- URUXPTBGYCJMMI-UHFFFAOYSA-N 7-nitro-9,10,10-trioxothioxanthene-2-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 URUXPTBGYCJMMI-UHFFFAOYSA-N 0.000 abstract 1
- NLLBEEJQCHRDQG-UHFFFAOYSA-N 8-chloro-10,10-dioxophenoxathiine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2S(=O)(=O)C3=CC(C(=O)O)=CC=C3OC2=C1 NLLBEEJQCHRDQG-UHFFFAOYSA-N 0.000 abstract 1
- BQXZQHUGENFMLF-UHFFFAOYSA-N 8-chloro-9,10,10-trioxothioxanthene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1Cl BQXZQHUGENFMLF-UHFFFAOYSA-N 0.000 abstract 1
- AZKLTHCOALUMOK-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2S(=O)(=O)C2=C1C(C(=O)O)=CC=C2 AZKLTHCOALUMOK-UHFFFAOYSA-N 0.000 abstract 1
- GPJLGGQFRRGOKR-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-2,5-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 GPJLGGQFRRGOKR-UHFFFAOYSA-N 0.000 abstract 1
- LZYYESNDLYVKKM-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 LZYYESNDLYVKKM-UHFFFAOYSA-N 0.000 abstract 1
- JBXXCFWIACSCEI-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-2,7-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 JBXXCFWIACSCEI-UHFFFAOYSA-N 0.000 abstract 1
- FATBSHSMRFRICI-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-2-carboxylic acid Chemical compound C1=CC=C2S(=O)(=O)C3=CC=C(C(=O)O)C=C3C(=O)C2=C1 FATBSHSMRFRICI-UHFFFAOYSA-N 0.000 abstract 1
- BAVYPOYYZZGSSK-UHFFFAOYSA-N 9,10,10-trioxothioxanthene-4,5-dicarboxylic acid Chemical compound O=C1C2=CC=CC(C(O)=O)=C2S(=O)(=O)C2=C1C=CC=C2C(=O)O BAVYPOYYZZGSSK-UHFFFAOYSA-N 0.000 abstract 1
- AJLLKBKSHTWSHL-UHFFFAOYSA-N 9-nitro-10,10-dioxophenoxathiine-4-carboxylic acid Chemical compound O1C2=CC=CC([N+]([O-])=O)=C2S(=O)(=O)C2=C1C(C(=O)O)=CC=C2 AJLLKBKSHTWSHL-UHFFFAOYSA-N 0.000 abstract 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 abstract 1
- 206010010741 Conjunctivitis Diseases 0.000 abstract 1
- 201000004624 Dermatitis Diseases 0.000 abstract 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 208000024780 Urticaria Diseases 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 208000010668 atopic eczema Diseases 0.000 abstract 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 abstract 1
- FESBZBHBDLEBID-UHFFFAOYSA-N dibenzothiophene-2-carboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)=CC=C3SC2=C1 FESBZBHBDLEBID-UHFFFAOYSA-N 0.000 abstract 1
- UYJXVMONIAGLRR-UHFFFAOYSA-L disodium;5,5-dioxodibenzothiophene-4,6-dicarboxylate Chemical compound [Na+].[Na+].C12=CC=CC(C([O-])=O)=C2S(=O)(=O)C2=C1C=CC=C2C(=O)[O-] UYJXVMONIAGLRR-UHFFFAOYSA-L 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- VBCDCZWIKNMFMI-UHFFFAOYSA-N methyl 9,10,10-trioxothioxanthene-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)C3=CC(C(=O)OC)=CC=C3C(=O)C2=C1 VBCDCZWIKNMFMI-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- SKXSSXKAWAWWHE-UHFFFAOYSA-M sodium;4-nitrobenzenethiolate Chemical compound [Na+].[O-][N+](=O)C1=CC=C([S-])C=C1 SKXSSXKAWAWWHE-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/382—Heterocyclic compounds having sulfur as a ring hetero atom having six-membered rings, e.g. thioxanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/12—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- 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
- 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
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/263—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings the aromatic rings being non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1447032 Tricyclic sulphones WELLCOME FOUNDATION Ltd 17 Aug 1973 [19 May 1972 6 Sept 1972 4 May 1973] 19552/76 and 19553/76 Divided out of 1447031 Heading C2C The invention comprises compounds of the formula wherein Z<SP>1</SP> is carboxyl, a carboxylate salt a (C 1 -C 6 ) -alkylcarboxylate or a carboxamide optionally substituted by (C 1 -C 6 )-alkyl, Z<SP>3</SP> is a bond, -CO-, -O-, -S-, -SO-, or -CH 2 - and Z<SP>2</SP> is H, a carboxylate salt, (C 1 - C 6 )-alkylsulphonyl, alkylsulphinyl, alkylthio, alkyl or alkoxy, (C 2 -C 7 )-alkanoyl or alkanoylamino, amino, NO 2 , CN or halogen, with the proviso that (1) when Z<SP>2</SP> is H or a carboxylate salt then Z<SP>1</SP> is a carboxylate salt, and (2) when Z<SP>3</SP> is -CO- and Z<SP>1</SP> is in the 2-position then Z<SP>2</SP> when in the 5-, 6- or 7-position, is other than halogen, alkanoyl, alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl; and except for 7 - nitro - 2 - carboxythioxanthone - 10,10- dioxide and its amide, 9-nitro-4-carboxyphenoxathiin - 10,10 - dioxide, 8 - chloro - 2 - carboxyphenoxathiin - 10,10 - dioxide and its methyl ester, 4,6-dicarboxydibenzothiophene- 5,5-dioxide disodium salt, and 8-chloro-2- carboxythioxanthone-10,10-dioxide. They may be obtained by (a) when Z<SP>1</SP> is carboxyl or a carboxylate salt, or both Z<SP>1</SP> and Z<SP>2</SP> are carboxylate salts, hydrolysing a compound of the formula wherein Y<SP>1</SP> is a carboxyl group precursor or is the same as Z<SP>1</SP> and Y<SP>2</SP> is carboxyl group precursor or is the same as Z<SP>2</SP>, with a base or with a dilute aqueous mineral acid optionally in the presence of an organic acid; (b) oxidizing a compound of the formula wherein Y<SP>5</SP> is alkyl, alkanoyl or is the same as Z<SP>1</SP>, Y<SP>3</SP> is the same as Z<SP>3</SP>, Y<SP>4</SP> is -S-, -SO-, or -SO 2 -, and Y<SP>6</SP> is alkyl, alkanoyl or is the same as Z<SP>2</SP>, provided that when Y<SP>5</SP> is the same as Z<SP>1</SP> and Y<SP>6</SP> is the same as Z<SP>2</SP> then at least Y<SP>4</SP> is - or Y<SP>3</SP> is -CH 2 - or -S-,-S-or-SO with an appropriate oxidizing agent; (c) when Z<SP>3</SP> is -O- or -S-, cyclizing a compound of the formula wherein one of R<SP>2</SP> and R<SP>3</SP> is SH, OH or an ester thereof and the other is a leaving group, with a base; (d) cyclizing a compound of the formula using a Lewis acid; (e) cyclizing a compound of the formula with C1SO 3 H; (f) when Z<SP>3</SP> is -S- or -CH 2 -, reducing the corresponding compound of Formula I wherein Z<SP>3</SP> is -SO- or -CO-, with an appropriate reducing agent; (g) when Z<SP>3</SP> is -S-, reacting a compound of the formula wherein R<SP>5</SP> and R<SP>6</SP> are each leaving groups, with sodium sulphide; or (h) when Z<SP>3</SP> is -CO-, cyclizing a compound of the formula wherein R<SP>1</SP> is -COOH or a derivative thereof or is -CHO, in the presence of a Lewis or protonic acid; and when a salt, an amide or an alkyl ester is required converting the products obtained above by appropriate reactions. Pharmaceutical compositions comprise the compounds of Formula I and in addition the compounds excluded by proviso (1) and those compounds specifically named, in association with an acceptable carrier. They are useful as inhibitors of allergic reactions associated with asthma, hay fever, conjunctivitis, urticaria and eczema and may be applied orally, rectally, ophthalmically, pulmonarily, nasally, dermally, topically or parenterally. The preparation of the following intermediates and other products is described: Prep. (1) 2-carboxydibenzothiophene-5,5-dioxide from dibenzothiophene via 2-acetyldibenzothiophene and dibenzothiophene-2-carboxylic acid; Prep. (2) 2,8-dicarboxyphenoxathiin-10,10-dioxide from 2,8-diacetylphenoxathiin via its 10,10-dioxide; Prep. (3) 2-methoxycarbonylphenoxathiin-1.0,10-dioxide from the corresponding free acid; Prep. (4) 3-carboxythioxanthone- 10,10-dioxide from benzene sulphonyl chloride and p-xylene via 2,5-dimethyldiphenyl sulphone and diphenyl sulphone-2,5-dicarboxylic acid; Prep. (5) 2-carbozyphenozathiin-10,10-dioxide by a route analogous to prep. (1); Preps. (6) and (7) 2-carboxythioxanthone-10,10-dioxide by a route analogous to prep. (4) or from toluene and omercaptobenzoic acid via methylthioxanthone and its 10,10-dioxide; Prep. (9) 3-carboxythioxanthone-10,10-dioxide from 3-carboxy-thioxanthone-10,10-dioxide; Prep. (10) 2,6-dicarboxythioxanthone - 10,10 - dioxide from diphenylsulphone 2,4<SP>1</SP>,5- tricarboxylic acid; Prep. (11) 2,7 - dicarboxythioxanthone - 10,10 - dioxide by a route analogous to prep. (4); Prep. (12) 3- methoxycarbonylthioxanthone - 10,10 - dioxide from the corresponding free acid; Example (1) 7 - ethylthioxanthone - 3 - carboxylic acid from ethylbenzene via p-ethylthiophenol, and 2-(pethylphenylthio) terephthalic acid; Example (2) 7 - t - butylthioxanthone - 3 - carboxylic acid from p - t - butylthiophenol and nitroterephthalonitrile via 2 - (p - t - butylphenylthio) terephthalic acid; Example (3) 2,8 - dimethylphenoxathiin - 10,10 - dioxide from p - bromotoluene and p-cresol via 4,4<SP>1</SP>-dimethyldiphenyl ether and 2,8-dimethylphenoxathiin; Example (4) p - chlorophenylsulphonyl terephthalic acid from p-chlorothiophenol and nitroterephthalonitrile via p-chlorophenylthioterephthalonitrile and the corresponding free acid; Example (5) 7 - methoxythioxanthone - 3 - carboxylic acid by a route analogous to Example (2); Prep. (15) 3- carboxydibenzothiophene - 5,5 - dioxide from dibenzothiophene - 5,5 - dioxide via 3 - nitro- and 3 - amino - dibenzothiophene - 5,5 - dioxide; Prep. (16) 3-carboxythioxanthene-10,10-dioxide from 3 - carboxythioxanthone - 10,10 - dioxide; Example (6) 7-methylthioxanthone-3-carboxylic acid by a route analogous to Example (2); Example (10) 7-Nitrothioxanthone- 3-carboxylic acid from sodium 4-nitrothiophenoxide and 2,5- dicyanonitrobenzene via 2,5-dicyano- 4<SP>1</SP>-nitrodiphenylsulphide and p - nitrothiophenoxy terephthalic acid; Prep. (17) 2,5-dicarboxythioxanthone-10,10-dioxide from thioxanthone-2,5-dicarboxylic acid which is itself obtained by a route analogous to Example (10); Prep. (18) 1-carboxythioxanthone-10,10-dioxide by a route analogous to Prep. (17); Prep. (19) 3-carboxythianthrene-5,5,10-trioxide from 3-carboxythianthrene-5,5-dioxide; and Prep. (20) 4,5-dicarboxythioxanthone-10,10-dioxide by a route analogous to Prep. (17). Other intermediates are described in Specification 1,447,031.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1955276A GB1447032A (en) | 1972-05-19 | 1972-05-19 | Tricyclic sulphones and pharmaceutical compositions containing them |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1955276A GB1447032A (en) | 1972-05-19 | 1972-05-19 | Tricyclic sulphones and pharmaceutical compositions containing them |
GB2380572 | 1972-05-19 | ||
GB1955376 | 1972-09-06 | ||
GB4142972 | 1972-09-06 | ||
GB1955476 | 1973-05-04 | ||
GB2117473*[A GB1447031A (en) | 1972-05-19 | 1973-05-04 | Tricyclic sulphones and pharmaceutical compositions containing them |
Publications (1)
Publication Number | Publication Date |
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GB1447032A true GB1447032A (en) | 1976-08-25 |
Family
ID=27546683
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1955276A Expired GB1447032A (en) | 1972-05-19 | 1972-05-19 | Tricyclic sulphones and pharmaceutical compositions containing them |
Country Status (1)
Country | Link |
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GB (1) | GB1447032A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0004257A1 (en) * | 1978-03-09 | 1979-09-19 | Sanofi S.A. | Benzonitrile derivative, process for its preparation and its application |
US4506083A (en) * | 1979-05-18 | 1985-03-19 | Ciba-Geigy Corporation | Thioxanthonecarboxylic acid esters, thioesters and amides |
EP0419157A2 (en) * | 1989-09-18 | 1991-03-27 | The Wellcome Foundation Limited | Pharmacologically active compound., preparation and use |
WO1992004897A1 (en) * | 1990-09-17 | 1992-04-02 | The Wellcome Foundation Limited | 1-substituted phenoxathiin derivatives as antidepressants |
EP1380580A1 (en) * | 2002-07-13 | 2004-01-14 | Great Lakes (UK) Limited | An improved process for the production of subsituted thioxanthones |
WO2008151719A2 (en) * | 2007-06-11 | 2008-12-18 | Bayer Cropscience Ag | 3-cyclopropyl-4-(3-thiobenzoyl)pyrazoles and their use as herbicides |
-
1972
- 1972-05-19 GB GB1955276A patent/GB1447032A/en not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0004257A1 (en) * | 1978-03-09 | 1979-09-19 | Sanofi S.A. | Benzonitrile derivative, process for its preparation and its application |
US4506083A (en) * | 1979-05-18 | 1985-03-19 | Ciba-Geigy Corporation | Thioxanthonecarboxylic acid esters, thioesters and amides |
US4505794A (en) * | 1979-05-18 | 1985-03-19 | Ciba-Geigy Corporation | Thioxanthonecarboxylic acid esters, thioesters and amides |
EP0419157A2 (en) * | 1989-09-18 | 1991-03-27 | The Wellcome Foundation Limited | Pharmacologically active compound., preparation and use |
EP0419157A3 (en) * | 1989-09-18 | 1991-08-28 | The Wellcome Foundation Limited | Pharmacologically active compound., preparation and use |
WO1992004897A1 (en) * | 1990-09-17 | 1992-04-02 | The Wellcome Foundation Limited | 1-substituted phenoxathiin derivatives as antidepressants |
EP1380580A1 (en) * | 2002-07-13 | 2004-01-14 | Great Lakes (UK) Limited | An improved process for the production of subsituted thioxanthones |
US6960668B2 (en) | 2002-07-13 | 2005-11-01 | Great Lakes (Uk) Limited | Process for the production of substituted thioxanthones |
WO2008151719A2 (en) * | 2007-06-11 | 2008-12-18 | Bayer Cropscience Ag | 3-cyclopropyl-4-(3-thiobenzoyl)pyrazoles and their use as herbicides |
WO2008151719A3 (en) * | 2007-06-11 | 2009-08-06 | Bayer Cropscience Ag | 3-cyclopropyl-4-(3-thiobenzoyl)pyrazoles and their use as herbicides |
US7943551B2 (en) | 2007-06-11 | 2011-05-17 | Bayer Cropscience Ag | 3-cyclopropyl-4-(3-thiobenzoyl) pyrazoles and their use as herbicides |
CN101679285B (en) * | 2007-06-11 | 2013-07-24 | 拜尔农作物科学股份公司 | 3-cyclopropyl-4-(3-thiobenzoyl)pyrazoles and their use as herbicides |
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