IE33125B1 - New heterocyclic carboxylic acids their preparation and use - Google Patents
New heterocyclic carboxylic acids their preparation and useInfo
- Publication number
- IE33125B1 IE33125B1 IE732/69A IE73269A IE33125B1 IE 33125 B1 IE33125 B1 IE 33125B1 IE 732/69 A IE732/69 A IE 732/69A IE 73269 A IE73269 A IE 73269A IE 33125 B1 IE33125 B1 IE 33125B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- compounds
- prepared
- bromomethyl
- halo
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- LUUIRSXAWQZPKD-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)butanoyl chloride Chemical compound CCC(Br)(CBr)C(Cl)=O LUUIRSXAWQZPKD-UHFFFAOYSA-N 0.000 abstract 1
- KHRWKDIDZURTCQ-UHFFFAOYSA-N 5-[2-bromo-2-(bromomethyl)butanoyl]-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound BrC(C(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C)(CC)CBr KHRWKDIDZURTCQ-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000004802 benzothiophens Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 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
- C07D333/60—Radicals substituted by 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
1,266,766. Benzofuran and benzothiophen derivatives. J. R. GEIGY A.G. 29 May, 1969 [30 May, 1968], No. 27282/69. Heading C2C. Novel compounds I in which R is a C 1-6 alkyl group; X is O or S; Y 1 and Y 2 are H or CH 3 ; and Z 1 and Z 2 are H, F, Cl, Br, CH 3 , C 2 H 5 , CH 3 O or C 2 H 5 O, and their salts with bases are prepared (a) by splitting off H-Am from a compound II in which Am is a secondary amino radical (b) by reacting the appropriate 5-unsubstituted compound with an acid halide where Cl is halo or an anhydride or (c) by dehalogenating a compound III where Cl is halo, followed if desired by salt formation. Intermediates isolated are the compounds II, prepared by reaction of the appropriate compounds which compounds are described in Specification 1,265,882 with formaldehyde or paraformaldehyde and H-Am; and 2,3-dihydro- 5 ( 2 - bromo - 2 - bromomethyl - butyryl) - 6 - methylbenzofuran-2-carboxylic acid, prepared from the 5-unsubstituted compound and 2-bromo-2- bromomethyl-butyryl chloride. Pharmaceutical compositions comprise a compound I in association with a suitable carrier, are administered orally and have diuretic and saluretic activity.
[GB1266766A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH803268A CH510007A (en) | 1968-05-30 | 1968-05-30 | Process for the preparation of new heterocyclic carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33125L IE33125L (en) | 1969-11-30 |
| IE33125B1 true IE33125B1 (en) | 1974-03-20 |
Family
ID=4334103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE732/69A IE33125B1 (en) | 1968-05-30 | 1969-05-29 | New heterocyclic carboxylic acids their preparation and use |
Country Status (19)
| Country | Link |
|---|---|
| AT (3) | AT286285B (en) |
| BE (1) | BE733769A (en) |
| BG (3) | BG15576A3 (en) |
| BR (1) | BR6909330D0 (en) |
| CH (3) | CH510008A (en) |
| CS (3) | CS158645B2 (en) |
| DE (1) | DE1927452C3 (en) |
| DK (1) | DK122607B (en) |
| ES (3) | ES367839A1 (en) |
| FI (1) | FI49417C (en) |
| FR (1) | FR2009653A1 (en) |
| GB (1) | GB1266766A (en) |
| IE (1) | IE33125B1 (en) |
| IL (1) | IL32311A (en) |
| NL (1) | NL6907974A (en) |
| NO (1) | NO122754B (en) |
| SE (1) | SE360859B (en) |
| SU (1) | SU402220A3 (en) |
| YU (1) | YU34041B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756105A (en) * | 1969-09-15 | 1971-03-15 | Geigy Ag J R | NEW HETEROCYCLIC CARBOXYLIC ACIDS AND MEDICINES CONTAINING SUCH ACIDS |
| BE759138A (en) * | 1969-11-20 | 1971-05-19 | Geigy Ag J R | BENZOFURAN AND BENZOTHIOPHENE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING SUCH SUBSTANCES |
| BE759137R (en) * | 1969-11-20 | 1971-05-19 | Geigy Ag J R | HETEROCYCLIC CARBOXYLIC ACIDS AND MEDICINAL PRODUCTS CONTAINING SUCH |
| JPS61158976A (en) * | 1984-12-28 | 1986-07-18 | Shionogi & Co Ltd | Benzofuran and benzothiophene derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL285498A (en) * | 1961-11-14 |
-
1968
- 1968-05-30 CH CH820371A patent/CH510008A/en not_active IP Right Cessation
- 1968-05-30 CH CH803268A patent/CH510007A/en not_active IP Right Cessation
- 1968-05-30 CH CH820471A patent/CH510009A/en not_active IP Right Cessation
-
1969
- 1969-05-23 DK DK283269AA patent/DK122607B/en unknown
- 1969-05-23 FI FI691565A patent/FI49417C/en active
- 1969-05-23 NL NL6907974A patent/NL6907974A/xx not_active Application Discontinuation
- 1969-05-23 NO NO2126/69A patent/NO122754B/no unknown
- 1969-05-23 SE SE07337/69A patent/SE360859B/xx unknown
- 1969-05-28 SU SU1334348A patent/SU402220A3/ru active
- 1969-05-29 BG BG012334A patent/BG15576A3/en unknown
- 1969-05-29 GB GB1266766D patent/GB1266766A/en not_active Expired
- 1969-05-29 BR BR209330/69A patent/BR6909330D0/en unknown
- 1969-05-29 AT AT511869A patent/AT286285B/en not_active IP Right Cessation
- 1969-05-29 YU YU1335/69A patent/YU34041B/en unknown
- 1969-05-29 CS CS563772*1A patent/CS158645B2/cs unknown
- 1969-05-29 ES ES367839A patent/ES367839A1/en not_active Expired
- 1969-05-29 ES ES367838A patent/ES367838A1/en not_active Expired
- 1969-05-29 IL IL32311A patent/IL32311A/en unknown
- 1969-05-29 ES ES367840A patent/ES367840A1/en not_active Expired
- 1969-05-29 FR FR6917585A patent/FR2009653A1/fr not_active Withdrawn
- 1969-05-29 BE BE733769D patent/BE733769A/xx unknown
- 1969-05-29 IE IE732/69A patent/IE33125B1/en unknown
- 1969-05-29 CS CS383369A patent/CS158643B2/cs unknown
- 1969-05-29 AT AT142770A patent/AT289783B/en not_active IP Right Cessation
- 1969-05-29 CS CS563672*1A patent/CS158644B2/cs unknown
- 1969-05-29 DE DE1927452A patent/DE1927452C3/en not_active Expired
- 1969-05-29 AT AT142670A patent/AT289782B/en active
- 1969-10-13 BG BG013176A patent/BG16178A3/en unknown
- 1969-10-18 BG BG013175A patent/BG15224A3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6909330D0 (en) | 1973-02-08 |
| CS158645B2 (en) | 1974-11-25 |
| AT289783B (en) | 1971-05-10 |
| CH510007A (en) | 1971-07-15 |
| NL6907974A (en) | 1969-12-02 |
| AT289782B (en) | 1971-05-10 |
| BE733769A (en) | 1969-12-01 |
| DE1927452A1 (en) | 1969-12-04 |
| ES367839A1 (en) | 1971-04-16 |
| CS158644B2 (en) | 1974-11-25 |
| SU402220A3 (en) | 1973-10-12 |
| BG16178A3 (en) | 1972-07-20 |
| SE360859B (en) | 1973-10-08 |
| CH510009A (en) | 1971-07-15 |
| BG15576A3 (en) | 1972-05-20 |
| YU133569A (en) | 1978-05-15 |
| FI49417C (en) | 1975-06-10 |
| ES367838A1 (en) | 1971-04-16 |
| IL32311A (en) | 1972-09-28 |
| CS158643B2 (en) | 1974-11-25 |
| DE1927452B2 (en) | 1978-02-02 |
| IL32311A0 (en) | 1969-07-30 |
| GB1266766A (en) | 1972-03-15 |
| BG15224A3 (en) | 1975-11-21 |
| FR2009653A1 (en) | 1970-02-06 |
| NO122754B (en) | 1971-08-09 |
| AT286285B (en) | 1970-12-10 |
| CH510008A (en) | 1971-07-15 |
| YU34041B (en) | 1978-10-31 |
| DK122607B (en) | 1972-03-20 |
| ES367840A1 (en) | 1971-04-16 |
| DE1927452C3 (en) | 1978-10-12 |
| IE33125L (en) | 1969-11-30 |
| FI49417B (en) | 1975-02-28 |
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