ES390707A1 - Bis basic ketones of dibenzothiophene - Google Patents
Bis basic ketones of dibenzothiopheneInfo
- Publication number
- ES390707A1 ES390707A1 ES390707A ES390707A ES390707A1 ES 390707 A1 ES390707 A1 ES 390707A1 ES 390707 A ES390707 A ES 390707A ES 390707 A ES390707 A ES 390707A ES 390707 A1 ES390707 A1 ES 390707A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- see formula
- group
- carbon atoms
- 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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 title abstract 5
- 150000002576 ketones Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- -1 dibenzothiophene ketones Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Procedure for preparing bis-basic dibenzothiophene ketones of the formula of: **(See formula)** where each A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is an elected member of the group consisting of (A) the group: **(See formula)** where R1 and R2 are individually hydrogen, lower alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkenyl having 3 to 6 carbon atoms and having vinyl unsaturation at a position other than that of position 1 of the alkenyl group; or (B) the group: **(See formula)** where n is an integer from 4 to 6 and R3 is hydrogen, lower alkyl having from 1 to about 4 carbon, phenyl or benzyl atoms, and can be linked to any one of the carbon atoms of the heterocyclic group; or (C) the group: **(See formula)** where X is oxygen or NR4, and R4 is hydrogen or lower alkyl having from 1 to about 4 carbon atoms; or (D) the group: **(See formula)** where p is an integer of 2 or 3 and m is an integer of 1 or 2, or (E) the group: **(See formula)** where q is an integer from 1 or 2 and r is an integer from 1 to 3, provided that when r equals 3, q is 1; or a pharmaceutically acceptable acid addition salt, of said base, characterized in that it is chosen between (I) to react a compound of the formula: **(See formula)** with an amine, Y-N, in which A and Y have the same meanings defined above, and hal is chosen from chlorine, bromine or iodine; (II) when A is an alkylene chain of 3 to 6 carbon atoms, react a dinitrile dibenzothiophene of the formula: **(See formula)** with a Grignard reagent of the formula: XMg (CH2) ZY so as to produce a compound of the formula: **(See formula)** where X is bromine or chlorine, z is 3 to 6 and Y may be as defined above, with the exception of those groups that contain a hydrogen attached to the nitrogen atom; (III) when A is -CH2CH2- and each Y is a secondary amine as defined above, a compound of the formula is reacted: **(See formula)** with formaldehyde and a compound of the formula Y-H so as to produce a compound of the formula: **(See formula)** where Y is a secondary amine as defined above; (IV) When the pharmaceutically acceptable acid addition salt is desired, the base compound of the formula is reacted: **(See formula)** with a pharmaceutically acceptable acid, where A and Y are as defined above. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3390270A | 1970-05-01 | 1970-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES390707A1 true ES390707A1 (en) | 1973-06-16 |
Family
ID=21873118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES390707A Expired ES390707A1 (en) | 1970-05-01 | 1971-04-29 | 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 CH CH626371A patent/CH560212A5/xx not_active IP Right Cessation
- 1971-04-28 SE SE7105505A patent/SE387346B/en unknown
- 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 BE BE766577A patent/BE766577A/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 CS CS7100003179A patent/CS180573B2/en unknown
- 1971-04-30 IE IE539/71A patent/IE35180B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2120996A1 (en) | 1971-11-18 |
| CA950456A (en) | 1974-07-02 |
| FR2092120A1 (en) | 1972-01-21 |
| DE2120996B2 (en) | 1979-08-02 |
| IE35180B1 (en) | 1975-12-10 |
| GB1292567A (en) | 1972-10-11 |
| IL36644A0 (en) | 1971-06-23 |
| NO131836B (en) | 1975-05-05 |
| ZA712219B (en) | 1972-01-26 |
| HU165245B (en) | 1974-07-27 |
| CS180573B2 (en) | 1978-01-31 |
| AT302290B (en) | 1972-10-10 |
| IL36644A (en) | 1974-12-31 |
| NO131836C (en) | 1975-08-13 |
| SE387346B (en) | 1976-09-06 |
| CH560212A5 (en) | 1975-03-27 |
| JPS553352B1 (en) | 1980-01-24 |
| FR2092120B1 (en) | 1974-08-23 |
| DE2120996C3 (en) | 1980-04-17 |
| BE766577A (en) | 1971-09-16 |
| IE35180L (en) | 1971-11-01 |
| PH9507A (en) | 1976-01-09 |
| NL7105854A (en) | 1971-11-03 |
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