IE35180L - Bis-basic ketones of dibenzothiophene. - Google Patents
Bis-basic ketones of dibenzothiophene.Info
- Publication number
- IE35180L IE35180L IE710539A IE53971A IE35180L IE 35180 L IE35180 L IE 35180L IE 710539 A IE710539 A IE 710539A IE 53971 A IE53971 A IE 53971A IE 35180 L IE35180 L IE 35180L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- dibenzothiophene
- group
- prepared
- reacted
- Prior art date
Links
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 title abstract 6
- 150000002576 ketones Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- JCXDSGPLPSOIDP-UHFFFAOYSA-N 1-(1-acetyldibenzothiophen-2-yl)ethanone Chemical compound C(C)(=O)C1=C(C2=C(SC3=C2C=CC=C3)C=C1)C(C)=O JCXDSGPLPSOIDP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000000840 anti-viral effect Effects 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
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- UXCPYODAKZNZAD-UHFFFAOYSA-N dibenzothiophene-1,2-dicarbonitrile Chemical compound C1=CC=C2C3=C(C#N)C(C#N)=CC=C3SC2=C1 UXCPYODAKZNZAD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 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
- C07D333/76—Dibenzothiophenes
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)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1292567 Bis basic ketones of dibenzothiophene RICHARDSON-MERRELL Inc 30 April 1971 [1 May 1970] 12495/71 Heading C2C Novel compounds of Formula Ia wherein Y is a group of Formula A wherein R 1 and R 2 are each H, C 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 alkenyl in which the vinyl unsaturation is not in the 1-position; or a group of Formula B wherein n is 4, 5 or 6 and R<SP>3</SP> is H, C 1-4 alkyl, phenyl or benzyl; or a group of Formula C wherein X is -O- or R 4 N where R 4 is H or C 1-4 alkyl; or a group of Formula D wherein m is 1 or 2 and p is 2 or 3 ; or a group of Formula E wherein q is or 2 and r is 1 or 2 or also 3 if q is 1; and A is a C 1-6 straight or branched-chain alkylene radical are prepared by one of the following methods (a) a compound of formula HY is reacted with a compound of Formula F wherein Hal is halogen or (b) a dicyano dibenzothiophene is reacted with a Grignard reagent of formula HalMgAY or (c) formaldehyde and a secondary amine HY is reacted with a diacetyldibenzothiophene. Compounds of Formula F above are prepared either by a Friedel-Crafts reaction on dibenzothiophene using a reagent or where A is CH 2 by halogenation of the methyl groups of the diacetyl dibenzothiophene which may be prepared by the above reaction using a reactive ester or anhydride of acetic acid. Compounds of Formula III are prepared either by dehydration of the diamide of the corresponding dicarboxylic acid or by diazatization of the corresponding diamine followed by reaction with cuprous cyanide. Pharmaceutical compositions having antiviral activity and being in conventional forms for oral, topical, bucal, internasal or parenteral administration comprise an above novel compound or salt and a non-toxic pharmaceutical carrier.
[GB1292567A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3390270A | 1970-05-01 | 1970-05-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35180L true IE35180L (en) | 1971-11-01 |
| IE35180B1 IE35180B1 (en) | 1975-12-10 |
Family
ID=21873118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE539/71A IE35180B1 (en) | 1970-05-01 | 1971-04-30 | Bis-basic ketones of dibenzothiophene |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS553352B1 (en) |
| AT (1) | AT302290B (en) |
| BE (1) | BE766577A (en) |
| CA (1) | CA950456A (en) |
| CH (1) | CH560212A5 (en) |
| CS (1) | CS180573B2 (en) |
| DE (1) | DE2120996C3 (en) |
| ES (1) | ES390707A1 (en) |
| FR (1) | FR2092120B1 (en) |
| GB (1) | GB1292567A (en) |
| HU (1) | HU165245B (en) |
| IE (1) | IE35180B1 (en) |
| IL (1) | IL36644A (en) |
| NL (1) | NL7105854A (en) |
| NO (1) | NO131836C (en) |
| PH (1) | PH9507A (en) |
| SE (1) | SE387346B (en) |
| ZA (1) | ZA712219B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3083201A (en) * | 1961-02-13 | 1963-03-26 | Smith Kline French Lab | Glyoxal derivatives of dibenzofuran and dibenzothiophene |
| US3867409A (en) * | 1969-06-16 | 1975-02-18 | Richardson Merrell Inc | Bis-basic esters of dibenzofuran |
-
1971
- 1971-04-06 CA CA109,720,A patent/CA950456A/en not_active Expired
- 1971-04-07 ZA ZA712219A patent/ZA712219B/en unknown
- 1971-04-16 PH PH12372*UA patent/PH9507A/en unknown
- 1971-04-18 IL IL36644A patent/IL36644A/en unknown
- 1971-04-21 JP JP2533371A patent/JPS553352B1/ja active Pending
- 1971-04-26 NO NO1543/71A patent/NO131836C/no unknown
- 1971-04-27 AT AT362971A patent/AT302290B/en not_active IP Right Cessation
- 1971-04-28 HU HURI428A patent/HU165245B/hu unknown
- 1971-04-28 SE SE7105505A patent/SE387346B/en unknown
- 1971-04-28 CH CH626371A patent/CH560212A5/xx not_active IP Right Cessation
- 1971-04-29 NL NL7105854A patent/NL7105854A/xx unknown
- 1971-04-29 DE DE2120996A patent/DE2120996C3/en not_active Expired
- 1971-04-29 ES ES390707A patent/ES390707A1/en not_active Expired
- 1971-04-30 IE IE539/71A patent/IE35180B1/en unknown
- 1971-04-30 GB GB02495/71A patent/GB1292567A/en not_active Expired
- 1971-04-30 FR FR7115646A patent/FR2092120B1/fr not_active Expired
- 1971-04-30 BE BE766577A patent/BE766577A/en unknown
- 1971-04-30 CS CS7100003179A patent/CS180573B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE387346B (en) | 1976-09-06 |
| BE766577A (en) | 1971-09-16 |
| FR2092120A1 (en) | 1972-01-21 |
| DE2120996C3 (en) | 1980-04-17 |
| ES390707A1 (en) | 1973-06-16 |
| NO131836C (en) | 1975-08-13 |
| JPS553352B1 (en) | 1980-01-24 |
| ZA712219B (en) | 1972-01-26 |
| CS180573B2 (en) | 1978-01-31 |
| HU165245B (en) | 1974-07-27 |
| GB1292567A (en) | 1972-10-11 |
| AT302290B (en) | 1972-10-10 |
| IL36644A (en) | 1974-12-31 |
| NL7105854A (en) | 1971-11-03 |
| FR2092120B1 (en) | 1974-08-23 |
| DE2120996A1 (en) | 1971-11-18 |
| IL36644A0 (en) | 1971-06-23 |
| IE35180B1 (en) | 1975-12-10 |
| NO131836B (en) | 1975-05-05 |
| DE2120996B2 (en) | 1979-08-02 |
| CH560212A5 (en) | 1975-03-27 |
| CA950456A (en) | 1974-07-02 |
| PH9507A (en) | 1976-01-09 |
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