GB1331203A - Substituted methoxyamine derivatives - Google Patents
Substituted methoxyamine derivativesInfo
- Publication number
- GB1331203A GB1331203A GB553172A GB553172A GB1331203A GB 1331203 A GB1331203 A GB 1331203A GB 553172 A GB553172 A GB 553172A GB 553172 A GB553172 A GB 553172A GB 1331203 A GB1331203 A GB 1331203A
- Authority
- GB
- United Kingdom
- Prior art keywords
- base
- salt
- general formula
- phthalimide
- prepared
- 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
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical class CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002585 base Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- -1 methoxy amines Chemical class 0.000 abstract 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NATYGMIGYVNKCZ-UHFFFAOYSA-N O-(1-pyridin-3-ylethyl)hydroxylamine Chemical compound CC(ON)C1=CC=CN=C1 NATYGMIGYVNKCZ-UHFFFAOYSA-N 0.000 abstract 1
- RZINCIDRGNGHEK-UHFFFAOYSA-N O-[(3,5-dimethoxy-4-octoxyphenyl)methyl]hydroxylamine Chemical compound C(CCCCCCC)OC1=C(C=C(CON)C=C1OC)OC RZINCIDRGNGHEK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000005543 phthalimide group Chemical class 0.000 abstract 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
1331203 Methoxyamine derivatives GYOGYSZERKUTATO INTEZET 7 Feb 1972 [15 Feb 1971] 5531/72 Heading C2C A process for the preparation of substituted methoxy amines of general formula in which R 1 represents an aliphatic, aromatic or heterocyclic radical and R 2 is a hydrogen atom or a saturated or unsaturated, straight-chained or branched, C 1-4 alkyl group and salts thereof, comprises reacting a compound of general formula R 1 -CH(R 2 )ON=A in which A is a substituted or unsubstituted phthaloyl group with a base of general formula R 3 -NH 2 or a salt thereof in which R 3 is hydrogen or an aliphatic, aromatic, araliphatic, alicyclic or heterocyclic radical and, if desired, transforming a base into a salt using an acid or forming a free base from a salt using a strong base. The reaction is carried out using equimolar amounts of phthalimide and primary amine and by reflux in C 1-3 aliphatic alcohol or in the absence of a solvent with the phthalimide and amine being fused at the boiling point of the amine. Novel compounds prepared by the process are crotyloxyamine, 4 - n - octyloxy - 3,5 - dimethoxybenzyloxyamine, and 1-(pyrid-3-yl)ethyloxyamine. The phthalimides from which the above compounds are prepared, are novel and are prepared by reacting N-hydroxy phthalimide with the appropriate halide in the presence of a base.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001155 HU162578B (en) | 1971-02-15 | 1971-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1331203A true GB1331203A (en) | 1973-09-26 |
Family
ID=10996690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB553172A Expired GB1331203A (en) | 1971-02-15 | 1972-02-07 | Substituted methoxyamine derivatives |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT316511B (en) |
| CA (1) | CA989394A (en) |
| CH (1) | CH566961A5 (en) |
| DE (1) | DE2206890A1 (en) |
| DK (1) | DK142027B (en) |
| FR (1) | FR2131350A5 (en) |
| GB (1) | GB1331203A (en) |
| HU (1) | HU162578B (en) |
| NL (1) | NL7201784A (en) |
| SE (1) | SE387936B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2651083A1 (en) * | 1976-11-09 | 1978-05-18 | Hoechst Ag | NEW O-ALKYLATED HYDROXYLAMINE, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| US5120849A (en) * | 1986-05-07 | 1992-06-09 | Basf Aktiengesellschaft | Preparation of o-substituted hydroxylamines |
| GB2296715A (en) * | 1994-10-28 | 1996-07-10 | Commw Scient Ind Res Org | Allyloxyimides |
| AU705642B2 (en) * | 1994-10-28 | 1999-05-27 | Commonwealth Scientific And Industrial Research Organisation | Bisallyloxyimides |
| US7312200B2 (en) | 2003-01-17 | 2007-12-25 | Bayer Cropscience Ag | 9-ketospinosyn derivatives |
| US20130289083A1 (en) * | 2007-11-30 | 2013-10-31 | Newlink Genetics Corporation | IDO Inhibitors |
-
1971
- 1971-02-15 HU HUGO001155 patent/HU162578B/hu unknown
-
1972
- 1972-02-07 GB GB553172A patent/GB1331203A/en not_active Expired
- 1972-02-10 CA CA134,406A patent/CA989394A/en not_active Expired
- 1972-02-11 NL NL7201784A patent/NL7201784A/xx not_active Application Discontinuation
- 1972-02-14 DE DE19722206890 patent/DE2206890A1/en active Pending
- 1972-02-14 DK DK66872A patent/DK142027B/en unknown
- 1972-02-14 SE SE173272A patent/SE387936B/en unknown
- 1972-02-15 AT AT120172A patent/AT316511B/en not_active IP Right Cessation
- 1972-02-15 FR FR7204947A patent/FR2131350A5/fr not_active Expired
- 1972-02-15 CH CH214772A patent/CH566961A5/xx not_active IP Right Cessation
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2651083A1 (en) * | 1976-11-09 | 1978-05-18 | Hoechst Ag | NEW O-ALKYLATED HYDROXYLAMINE, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| US5120849A (en) * | 1986-05-07 | 1992-06-09 | Basf Aktiengesellschaft | Preparation of o-substituted hydroxylamines |
| GB2296715A (en) * | 1994-10-28 | 1996-07-10 | Commw Scient Ind Res Org | Allyloxyimides |
| US5760165A (en) * | 1994-10-28 | 1998-06-02 | Commonwealth Scientific And Industrial Research Organization (Csiro) | Bisallyloxyimides |
| GB2296715B (en) * | 1994-10-28 | 1998-09-16 | Commw Scient Ind Res Org | Bisallyloxyimides |
| AU705642B2 (en) * | 1994-10-28 | 1999-05-27 | Commonwealth Scientific And Industrial Research Organisation | Bisallyloxyimides |
| US7312200B2 (en) | 2003-01-17 | 2007-12-25 | Bayer Cropscience Ag | 9-ketospinosyn derivatives |
| US20130289083A1 (en) * | 2007-11-30 | 2013-10-31 | Newlink Genetics Corporation | IDO Inhibitors |
| US10047066B2 (en) | 2007-11-30 | 2018-08-14 | Newlink Genetics Corporation | IDO inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| SE387936B (en) | 1976-09-20 |
| NL7201784A (en) | 1972-08-17 |
| AT316511B (en) | 1974-07-10 |
| CA989394A (en) | 1976-05-18 |
| HU162578B (en) | 1973-03-28 |
| DK142027C (en) | 1981-02-16 |
| CH566961A5 (en) | 1975-09-30 |
| DE2206890A1 (en) | 1972-08-31 |
| FR2131350A5 (en) | 1972-11-10 |
| DK142027B (en) | 1980-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |