GB585362A - New heterocyclic compounds - Google Patents
New heterocyclic compoundsInfo
- Publication number
- GB585362A GB585362A GB1044044A GB1044044A GB585362A GB 585362 A GB585362 A GB 585362A GB 1044044 A GB1044044 A GB 1044044A GB 1044044 A GB1044044 A GB 1044044A GB 585362 A GB585362 A GB 585362A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetic acid
- dichloro
- chloroaniline
- naphthylamine
- quinoline
- 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
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 24
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 6
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- ISJBQSJDQZLCSF-UHFFFAOYSA-N (4-chlorophenyl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C(Cl)C=C1 ISJBQSJDQZLCSF-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- UBLKHAWYJFEPDX-UHFFFAOYSA-N 6-bromonaphthalen-2-amine Chemical compound C1=C(Br)C=CC2=CC(N)=CC=C21 UBLKHAWYJFEPDX-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- JQXCGCPMGZBMLE-UHFFFAOYSA-N benzo[f]isoquinoline Chemical compound N1=CC=C2C3=CC=CC=C3C=CC2=C1 JQXCGCPMGZBMLE-UHFFFAOYSA-N 0.000 abstract 1
- VQAZCUCWHIIFGE-UHFFFAOYSA-N diethyl 2-ethylpropanedioate Chemical compound CCOC(=O)C(CC)C(=O)OCC VQAZCUCWHIIFGE-UHFFFAOYSA-N 0.000 abstract 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
Abstract
4-Halogenoquinolines carrying in the 2-position an arylamino group free from acidic substituents, are obtained by the interaction of an appropriate arylamine with a 2 : 4-dihalogenoquinoline, optionally in the presence of a solvent or diluent. Examples relate to the interaction of 2 : 4-dichloroquinoline with (1) p-chloroaniline in acetic acid, (2) p-chloroaniline in chlorobenzene, (3) aniline in acetic acid, (4) p-anisidine in acetic acid, (5) p-toluidine in acetic acid, and (6) b -naphthylamine in acetic acid; (7) of 2 : 4-dichloro-7 : 8-benzquinoline with p-chloraniline in b -ethoxyethanol in the presence of p-chloroaniline hydrochloride; of 2 : 4-dichloro-quinoline with (8) 6-bromo-2-naphthylamine in acetic acid, and (9) p-nitroaniline in acetic acid; and of p-chloroaniline in acetic acid with (10) 2 : 4-dichloro - 3 - methyl - quinoline and (11) 2 : 4 - dichloro - 3 - ethyl - quinoline. Specification 585,363 is referred to. 7 : 8 - Benzo-, 3 - methyl - and 3 - ethyl - 2 : 4 - dichloroquinolines are obtained by treating with phosphorus oxychloride the products of reaction of a -naphthylamine with diethyl malonate, aniline with diethyl methyl malonate and aniline with diethyl ethyl malonate respectively.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1044044A GB585362A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1044044A GB585362A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB585362A true GB585362A (en) | 1947-02-05 |
Family
ID=9967905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1044044A Expired GB585362A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB585362A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150307478A1 (en) * | 2009-06-12 | 2015-10-29 | Abivax | Compounds useful for treating aids |
| US9827237B2 (en) | 2013-07-05 | 2017-11-28 | Abivax | Compounds useful for treating diseases caused by retroviruses |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| US11441181B2 (en) | 2013-01-17 | 2022-09-13 | Abivax | miRNA-124 as a biomarker |
| US11649211B2 (en) | 2014-07-17 | 2023-05-16 | Abivax | Use of quinoline derivatives for the treatment of inflammatory diseases |
| US11992499B2 (en) | 2018-12-20 | 2024-05-28 | Abivax | Quinoline derivatives for use in the treatment of inflammation diseases |
-
1944
- 1944-08-31 GB GB1044044A patent/GB585362A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10683284B2 (en) | 2009-06-12 | 2020-06-16 | Abivax | Compounds for preventing, inhibiting, or treating cancer, aids and/or premature aging |
| US20150307478A1 (en) * | 2009-06-12 | 2015-10-29 | Abivax | Compounds useful for treating aids |
| US9908869B2 (en) | 2009-06-12 | 2018-03-06 | Abivax | Compounds useful for treating aids |
| US10017498B2 (en) * | 2009-06-12 | 2018-07-10 | Abivax | Compounds useful for treating AIDS |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| US11014918B2 (en) | 2009-06-12 | 2021-05-25 | Abivax | Compounds and pharmaceutical compositions containing at least one of the compounds |
| US10975063B2 (en) | 2009-06-12 | 2021-04-13 | Abivax | Compound, and production method thereof, and methods of treatment using the compound |
| US9637475B2 (en) | 2009-06-12 | 2017-05-02 | Abivax | Compounds for treating cancer |
| US11441181B2 (en) | 2013-01-17 | 2022-09-13 | Abivax | miRNA-124 as a biomarker |
| US9827237B2 (en) | 2013-07-05 | 2017-11-28 | Abivax | Compounds useful for treating diseases caused by retroviruses |
| US11649211B2 (en) | 2014-07-17 | 2023-05-16 | Abivax | Use of quinoline derivatives for the treatment of inflammatory diseases |
| US11649210B2 (en) | 2014-07-17 | 2023-05-16 | Abivax | Use of quinoline derivatives for the treatment of inflammatory diseases |
| US12202804B2 (en) | 2014-07-17 | 2025-01-21 | Abivax | In vitro or ex vivo methods for screening a quinoline derivative |
| US11992499B2 (en) | 2018-12-20 | 2024-05-28 | Abivax | Quinoline derivatives for use in the treatment of inflammation diseases |
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