CA1051890A - Esters of theophyllinylacetic acid - Google Patents
Esters of theophyllinylacetic acidInfo
- Publication number
- CA1051890A CA1051890A CA248,568A CA248568A CA1051890A CA 1051890 A CA1051890 A CA 1051890A CA 248568 A CA248568 A CA 248568A CA 1051890 A CA1051890 A CA 1051890A
- Authority
- CA
- Canada
- Prior art keywords
- theophyllinyl
- formula
- compound
- nicotinoyloxy
- 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
- 239000002253 acid Substances 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 18
- -1 nicotinoyl Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 4
- 239000001294 propane Substances 0.000 claims 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- SVNDKURPKOXEKI-UHFFFAOYSA-N 2-hydroxypropyl pyridine-3-carboxylate Chemical compound CC(O)COC(=O)C1=CC=CN=C1 SVNDKURPKOXEKI-UHFFFAOYSA-N 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract 1
- 230000001739 rebound effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752512886 DE2512886A1 (de) | 1975-03-24 | 1975-03-24 | Neue ester der theophyllinyl-7- essigsaeure, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelpraeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051890A true CA1051890A (en) | 1979-04-03 |
Family
ID=5942253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,568A Expired CA1051890A (en) | 1975-03-24 | 1976-03-23 | Esters of theophyllinylacetic acid |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6043352B2 (en:Method) |
| AR (2) | AR211336A1 (en:Method) |
| AT (1) | AT344191B (en:Method) |
| BE (1) | BE839890A (en:Method) |
| CA (1) | CA1051890A (en:Method) |
| CH (1) | CH605950A5 (en:Method) |
| DK (1) | DK140843B (en:Method) |
| ES (2) | ES446321A1 (en:Method) |
| FI (1) | FI760755A7 (en:Method) |
| FR (1) | FR2305184A1 (en:Method) |
| GB (1) | GB1496298A (en:Method) |
| HU (1) | HU174879B (en:Method) |
| IE (1) | IE42788B1 (en:Method) |
| NL (1) | NL7603103A (en:Method) |
| SE (2) | SE419864B (en:Method) |
| ZA (1) | ZA761801B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714883A1 (de) * | 1977-04-02 | 1978-10-12 | Basf Ag | Nicht-glykosidische theophyllin- zucker-derivate |
-
1976
- 1976-03-18 GB GB10871/76A patent/GB1496298A/en not_active Expired
- 1976-03-19 FR FR7608048A patent/FR2305184A1/fr active Granted
- 1976-03-22 BE BE165447A patent/BE839890A/xx not_active IP Right Cessation
- 1976-03-22 FI FI760755A patent/FI760755A7/fi not_active Application Discontinuation
- 1976-03-22 IE IE601/76A patent/IE42788B1/en unknown
- 1976-03-22 AT AT209376A patent/AT344191B/de not_active IP Right Cessation
- 1976-03-23 SE SE7603564A patent/SE419864B/xx unknown
- 1976-03-23 CA CA248,568A patent/CA1051890A/en not_active Expired
- 1976-03-23 JP JP51031891A patent/JPS6043352B2/ja not_active Expired
- 1976-03-23 DK DK128076AA patent/DK140843B/da not_active IP Right Cessation
- 1976-03-24 ES ES446321A patent/ES446321A1/es not_active Expired
- 1976-03-24 NL NL7603103A patent/NL7603103A/xx not_active Application Discontinuation
- 1976-03-24 CH CH365876A patent/CH605950A5/xx not_active IP Right Cessation
- 1976-03-24 ZA ZA761801A patent/ZA761801B/xx unknown
- 1976-03-24 HU HU76WU24A patent/HU174879B/hu unknown
- 1976-03-26 AR AR262675A patent/AR211336A1/es active
- 1976-11-08 AR AR265378A patent/AR217246A1/es active
-
1977
- 1977-06-14 ES ES459777A patent/ES459777A1/es not_active Expired
-
1979
- 1979-03-19 SE SE7902463A patent/SE7902463L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51118794A (en) | 1976-10-18 |
| AR217246A1 (es) | 1980-03-14 |
| JPS6043352B2 (ja) | 1985-09-27 |
| ZA761801B (en) | 1977-03-30 |
| FR2305184B1 (en:Method) | 1979-09-21 |
| AR211336A1 (es) | 1977-11-30 |
| AT344191B (de) | 1978-07-10 |
| IE42788L (en) | 1976-09-24 |
| DK140843C (en:Method) | 1980-04-28 |
| DK128076A (en:Method) | 1976-09-25 |
| FI760755A7 (en:Method) | 1976-09-25 |
| ATA209376A (de) | 1977-11-15 |
| SE7902463L (sv) | 1979-03-19 |
| FR2305184A1 (fr) | 1976-10-22 |
| BE839890A (fr) | 1976-09-22 |
| SE7603564L (sv) | 1976-09-25 |
| DK140843B (da) | 1979-11-26 |
| HU174879B (hu) | 1980-03-28 |
| IE42788B1 (en) | 1980-10-22 |
| SE419864B (sv) | 1981-08-31 |
| ES459777A1 (es) | 1978-04-01 |
| CH605950A5 (en:Method) | 1978-10-13 |
| GB1496298A (en) | 1977-12-30 |
| NL7603103A (nl) | 1976-09-28 |
| ES446321A1 (es) | 1977-10-01 |
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