GB1173485A - New Amides of 3,4,5-Trimethoxyphenoxyacetic Acid - Google Patents
New Amides of 3,4,5-Trimethoxyphenoxyacetic AcidInfo
- Publication number
- GB1173485A GB1173485A GB07221/67A GB1722167A GB1173485A GB 1173485 A GB1173485 A GB 1173485A GB 07221/67 A GB07221/67 A GB 07221/67A GB 1722167 A GB1722167 A GB 1722167A GB 1173485 A GB1173485 A GB 1173485A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- formula
- hydroxy
- hydroxy compounds
- amino
- 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
- 150000001408 amides Chemical class 0.000 title abstract 3
- DUUIKSNOGTVREZ-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenoxy)acetic acid Chemical compound COC1=CC(OCC(O)=O)=CC(OC)=C1OC DUUIKSNOGTVREZ-UHFFFAOYSA-N 0.000 title 1
- -1 saturated heterocyclic amine Chemical group 0.000 abstract 5
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 241000223211 Curvularia lunata Species 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Chemical group 0.000 abstract 1
- 240000005384 Rhizopus oryzae Species 0.000 abstract 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 abstract 1
- 241001085826 Sporotrichum Species 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 238000010564 aerobic fermentation Methods 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- AGLSQIHENCAJLE-UHFFFAOYSA-N n-(4-hydroxyimino-1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC1(NC(=O)C)CC2C3=NO AGLSQIHENCAJLE-UHFFFAOYSA-N 0.000 abstract 1
- DNADEDKIQXROFJ-UHFFFAOYSA-N n-(4-oxo-1-adamantyl)acetamide Chemical compound C1C(C2)CC3CC1(NC(=O)C)CC2C3=O DNADEDKIQXROFJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000015097 nutrients Nutrition 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000001706 oxygenating effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,173,485. Amides. SPOFA, UNITED PHARMACEUTICAL WORKS. 14 April, 1967 [18 April, 1966], No. 17221/67. Heading C2C. Novel amides of the formula wherein R<SP>1</SP> represents hydrogen or C 1-4 alkyl, R<SP>2</SP> represents hydrogen, amino, C 1-4 alkyl, aminoalkyl, dialkylamino or aralkyl or NR<SP>1</SP>R<SP>2</SP> represents the residue of a secondary saturated heterocyclic amine with 2-5 carbon atoms which may contain a second hetero atom are prepared by reacting the corresponding C 1-4 alkyl ester with R<SP>1</SP>R<SP>2</SP>NH, wherein R<SP>1</SP> and R<SP>2</SP> have the above significance (an example also describes the preparation of a novel compound wherein R<SP>1</SP> represents hydrogen and R<SP>2</SP> represents amino by reaction of the free acid with hydrazine. Methyl 3,4,5 - trimethoxyphenoxy acetate is prepared by esterifying the free acid with dimethyl sulphate. in which Acyl is an acyl radical of a monobasic hydrocarbon carboxylic acid of from 1 to 18 carbon atoms, X is hydroxy, keto, acyloxy or tetrahydropyranyloxy and Y is hydroxy, acyloxy or tetrahydropyranyloxy, are prepared by subjecting a compound of Formula III to the oxygenating activity of Sporotrichum sulfurescens, Rhizopus arrhizus or Curvularia lunata in an aqueous nutrient medium under aerobic fermentation conditions to give hydroxy compounds of Formulµ IV and V and, if desired, acylating these hydroxy compounds to give the corresponding acyloxy derivatives, or treating the hydroxy compounds with dihydropyran to form the corresponding tetrahydropyranyl ethers, or oxidizing the hydroxy compounds of Formula IV to form the corresponding ketones. 1-Acetamidoadamantan-4-one oxime is prepared by reacting 1-acetamido-adamantan-4- one with hydroxylamine. Starting materials of Formula III are prepared by acylating 1-amino-adamantane with appropriate acylating agents. Pharmaceutical compositions having central nervous stimulant activity, for oral or parenteral administration, comprise a compound of Formula I or II together with a carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS256166 | 1966-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1173485A true GB1173485A (en) | 1969-12-10 |
Family
ID=5363081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB07221/67A Expired GB1173485A (en) | 1966-04-18 | 1967-04-14 | New Amides of 3,4,5-Trimethoxyphenoxyacetic Acid |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT268255B (en) |
| BE (1) | BE696899A (en) |
| CH (1) | CH487118A (en) |
| DE (1) | DE1618877A1 (en) |
| DK (1) | DK120184B (en) |
| FR (1) | FR6696M (en) |
| GB (1) | GB1173485A (en) |
| NL (1) | NL6705185A (en) |
| SE (1) | SE335853B (en) |
-
1967
- 1967-04-10 CH CH501667A patent/CH487118A/en not_active IP Right Cessation
- 1967-04-11 AT AT341667A patent/AT268255B/en active
- 1967-04-11 BE BE696899D patent/BE696899A/xx unknown
- 1967-04-11 DK DK198967A patent/DK120184B/en unknown
- 1967-04-12 NL NL6705185A patent/NL6705185A/xx unknown
- 1967-04-14 SE SE524267A patent/SE335853B/xx unknown
- 1967-04-14 GB GB07221/67A patent/GB1173485A/en not_active Expired
- 1967-04-15 DE DE19671618877 patent/DE1618877A1/en active Pending
- 1967-07-13 FR FR114367A patent/FR6696M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK120184B (en) | 1971-04-26 |
| NL6705185A (en) | 1967-10-19 |
| FR6696M (en) | 1969-02-10 |
| CH487118A (en) | 1970-03-15 |
| DE1618877A1 (en) | 1971-05-13 |
| AT268255B (en) | 1969-02-10 |
| BE696899A (en) | 1967-09-18 |
| SE335853B (en) | 1971-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |