GB1312470A - Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same - Google Patents
Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing sameInfo
- Publication number
- GB1312470A GB1312470A GB5494670A GB5494670A GB1312470A GB 1312470 A GB1312470 A GB 1312470A GB 5494670 A GB5494670 A GB 5494670A GB 5494670 A GB5494670 A GB 5494670A GB 1312470 A GB1312470 A GB 1312470A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- reacting
- compound
- prepared
- carboxylic 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title abstract 4
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical class C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- -1 dichloromethyl alkyl ether Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 2
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 abstract 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 abstract 1
- LQWJCKLAJRCTRP-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-sulfanylprop-2-enoic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C=C(C(=O)O)S LQWJCKLAJRCTRP-UHFFFAOYSA-N 0.000 abstract 1
- DUTNBAQMMZPIKM-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound ClC1=CC(Cl)=CC=C1C=C1C(=O)NC(=S)S1 DUTNBAQMMZPIKM-UHFFFAOYSA-N 0.000 abstract 1
- ZQWOLTVJEJDOFX-UHFFFAOYSA-N 6,7-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1C ZQWOLTVJEJDOFX-UHFFFAOYSA-N 0.000 abstract 1
- AVAGKGZNBMZOLD-UHFFFAOYSA-N 6-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(C(=O)O)=CC2=C1 AVAGKGZNBMZOLD-UHFFFAOYSA-N 0.000 abstract 1
- CDZHZOSUCIBINM-UHFFFAOYSA-N 6-chloro-2,3-dihydro-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(C(=O)O)CC2=C1 CDZHZOSUCIBINM-UHFFFAOYSA-N 0.000 abstract 1
- QXBQJXVMLMPNHS-UHFFFAOYSA-N 7,8-dimethylchromen-2-one Chemical compound C1=CC(=O)OC2=C(C)C(C)=CC=C21 QXBQJXVMLMPNHS-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1727369A CH523236A (de) | 1969-11-20 | 1969-11-20 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1312470A true GB1312470A (en) | 1973-04-04 |
Family
ID=4424112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5494670A Expired GB1312470A (en) | 1969-11-20 | 1970-11-19 | Benzofuran and benzothiophene carboxylic acids processes for their production and medicaments containing same |
Country Status (15)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH510007A (de) * | 1968-05-30 | 1971-07-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
-
0
- BE BE759138D patent/BE759138A/xx unknown
-
1969
- 1969-11-20 CH CH644672A patent/CH523237A/de not_active IP Right Cessation
- 1969-11-20 CH CH1727369A patent/CH523236A/de not_active IP Right Cessation
-
1970
- 1970-11-13 SE SE7015345A patent/SE375531B/xx unknown
- 1970-11-13 DK DK576570AA patent/DK126038B/da unknown
- 1970-11-13 NL NL7016683A patent/NL7016683A/xx unknown
- 1970-11-19 ES ES385701A patent/ES385701A1/es not_active Expired
- 1970-11-19 BG BG016099A patent/BG18182A3/xx unknown
- 1970-11-19 IL IL35693A patent/IL35693A/en unknown
- 1970-11-19 AT AT1042970A patent/AT299937B/de not_active IP Right Cessation
- 1970-11-19 FR FR707041566A patent/FR2073396B1/fr not_active Expired
- 1970-11-19 GB GB5494670A patent/GB1312470A/en not_active Expired
- 1970-11-19 ES ES385702A patent/ES385702A1/es not_active Expired
- 1970-11-19 ZA ZA707819A patent/ZA707819B/xx unknown
- 1970-11-19 DE DE19702056935 patent/DE2056935A1/de active Pending
- 1970-11-19 AT AT726471A patent/AT305275B/de not_active IP Right Cessation
- 1970-11-19 SU SU1494507A patent/SU366609A3/ru active
- 1970-11-19 CA CA098,563A patent/CA963016A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT305275B (de) | 1973-02-26 |
| NL7016683A (enrdf_load_stackoverflow) | 1971-05-24 |
| DK126038B (da) | 1973-06-04 |
| IL35693A0 (en) | 1971-01-28 |
| CH523236A (de) | 1972-05-31 |
| FR2073396B1 (enrdf_load_stackoverflow) | 1974-02-22 |
| ES385702A1 (es) | 1973-04-01 |
| AT299937B (de) | 1972-07-10 |
| BE759138A (fr) | 1971-05-19 |
| ES385701A1 (es) | 1973-10-01 |
| CA963016A (en) | 1975-02-18 |
| BG18182A3 (bg) | 1974-09-02 |
| IL35693A (en) | 1973-06-29 |
| FR2073396A1 (enrdf_load_stackoverflow) | 1971-10-01 |
| CH523237A (de) | 1972-05-31 |
| SU366609A3 (enrdf_load_stackoverflow) | 1973-01-16 |
| SE375531B (enrdf_load_stackoverflow) | 1975-04-21 |
| DE2056935A1 (de) | 1971-05-27 |
| ZA707819B (en) | 1971-08-25 |
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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 |