GB1593568A - 5-acetyl-4-hydroxy-3-(1-phenylaminoethylidene)-2h-pyran-2,6(3h)-diones - Google Patents
5-acetyl-4-hydroxy-3-(1-phenylaminoethylidene)-2h-pyran-2,6(3h)-diones Download PDFInfo
- Publication number
- GB1593568A GB1593568A GB17031/78A GB1703178A GB1593568A GB 1593568 A GB1593568 A GB 1593568A GB 17031/78 A GB17031/78 A GB 17031/78A GB 1703178 A GB1703178 A GB 1703178A GB 1593568 A GB1593568 A GB 1593568A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glyceramoyl
- pharmaceutical composition
- compound according
- composition according
- pyran
- 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
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- BIFDLOHPLATVEX-UHFFFAOYSA-N 3-acetyl-5-(1-anilinoethylidene)-4-hydroxypyran-2,6-dione Chemical class O=C1OC(=O)C(C(=O)C)=C(O)C1=C(C)NC1=CC=CC=C1 BIFDLOHPLATVEX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- -1 ketomalonamoyl Chemical group 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- ISDVKWGLGFGXJD-UHFFFAOYSA-N chembl3248291 Chemical compound CC(=O)C1=C(O)OC(=O)C(C(C)=O)=C1O ISDVKWGLGFGXJD-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
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- 239000003937 drug carrier Substances 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YREGFSKHUMGRCE-UHFFFAOYSA-N 3-(3-nitroanilino)-2,3-dioxopropanoic acid Chemical compound OC(=O)C(=O)C(=O)NC1=CC=CC([N+]([O-])=O)=C1 YREGFSKHUMGRCE-UHFFFAOYSA-N 0.000 description 4
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- SYYMTEQCCWYXDU-UHFFFAOYSA-N 2,3-dihydroxy-n-(3-nitrophenyl)propanamide Chemical compound OCC(O)C(=O)NC1=CC=CC([N+]([O-])=O)=C1 SYYMTEQCCWYXDU-UHFFFAOYSA-N 0.000 description 3
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 3
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- 229930006000 Sucrose Natural products 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
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- 239000005720 sucrose Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical class O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 2
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 2
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- UCWGBQUWEHTDJA-UHFFFAOYSA-N n-(3-amino-5-nitrophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide Chemical compound O1C(C)(C)OCC1C(=O)NC1=CC(N)=CC([N+]([O-])=O)=C1 UCWGBQUWEHTDJA-UHFFFAOYSA-N 0.000 description 2
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- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79215177A | 1977-04-29 | 1977-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1593568A true GB1593568A (en) | 1981-07-22 |
Family
ID=25155958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17031/78A Expired GB1593568A (en) | 1977-04-29 | 1978-04-28 | 5-acetyl-4-hydroxy-3-(1-phenylaminoethylidene)-2h-pyran-2,6(3h)-diones |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS53135982A (enrdf_load_stackoverflow) |
| DE (1) | DE2818984A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2388808A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1593568A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62188846U (enrdf_load_stackoverflow) * | 1986-05-22 | 1987-12-01 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1064509A (en) * | 1974-07-29 | 1979-10-16 | Smith Kline And French Canada Ltd. | Substituted 2h-pyran-2,6(3h)-dione derivatives |
-
1978
- 1978-04-24 FR FR7812038A patent/FR2388808A1/fr active Granted
- 1978-04-28 JP JP5326078A patent/JPS53135982A/ja active Granted
- 1978-04-28 GB GB17031/78A patent/GB1593568A/en not_active Expired
- 1978-04-28 DE DE19782818984 patent/DE2818984A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2388808B1 (enrdf_load_stackoverflow) | 1982-05-28 |
| JPS53135982A (en) | 1978-11-28 |
| DE2818984A1 (de) | 1978-11-02 |
| FR2388808A1 (fr) | 1978-11-24 |
| JPS6244550B2 (enrdf_load_stackoverflow) | 1987-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed |