PT85998B - Processo para a preparacao de derivados de quinoxalinona - Google Patents
Processo para a preparacao de derivados de quinoxalinona Download PDFInfo
- Publication number
- PT85998B PT85998B PT85998A PT8599887A PT85998B PT 85998 B PT85998 B PT 85998B PT 85998 A PT85998 A PT 85998A PT 8599887 A PT8599887 A PT 8599887A PT 85998 B PT85998 B PT 85998B
- Authority
- PT
- Portugal
- Prior art keywords
- dihydro
- quinoxalinone
- acid
- sulfonyl
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 21
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract description 3
- 125000004799 bromophenyl group Chemical group 0.000 claims abstract description 3
- 125000004188 dichlorophenyl group Chemical group 0.000 claims abstract description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims abstract description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
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- 229910052740 iodine Chemical group 0.000 claims description 2
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- 238000009833 condensation Methods 0.000 claims 2
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- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 15
- 230000001684 chronic effect Effects 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
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- 239000000047 product Substances 0.000 description 21
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- 238000004458 analytical method Methods 0.000 description 17
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- 235000003599 food sweetener Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002997 ophthalmic solution Substances 0.000 description 1
- 229940054534 ophthalmic solution Drugs 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1986/002335 WO1992005160A1 (en) | 1986-10-30 | 1986-10-30 | 4-arylsulfonyl-3,4-dihydro-2(1h)-quinoxalinone-1-alkanoic acids, esters, and salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT85998A PT85998A (en) | 1987-11-01 |
| PT85998B true PT85998B (pt) | 1990-08-31 |
Family
ID=22195697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT85998A PT85998B (pt) | 1986-10-30 | 1987-10-27 | Processo para a preparacao de derivados de quinoxalinona |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4940708A (en, 2012) |
| EP (1) | EP0266102B1 (en, 2012) |
| JP (1) | JPS63295566A (en, 2012) |
| AT (1) | ATE86985T1 (en, 2012) |
| DE (1) | DE3784835T2 (en, 2012) |
| DK (1) | DK561487A (en, 2012) |
| ES (1) | ES2046206T3 (en, 2012) |
| GR (1) | GR3007402T3 (en, 2012) |
| IE (1) | IE68851B1 (en, 2012) |
| PT (1) | PT85998B (en, 2012) |
| WO (1) | WO1992005160A1 (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992005160A1 (en) * | 1986-10-30 | 1992-04-02 | Reinhard Sarges | 4-arylsulfonyl-3,4-dihydro-2(1h)-quinoxalinone-1-alkanoic acids, esters, and salts |
| DE59209965D1 (de) * | 1991-04-15 | 2002-10-17 | Aventis Pharma Gmbh | Chinoxaline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6369057B1 (en) | 1991-04-15 | 2002-04-09 | Aventis Pharma Deutschland Gmbh | Quinoxalines, processes for their preparation and their use |
| US7351709B2 (en) | 2004-06-09 | 2008-04-01 | Wyeth | Estrogen receptor ligands |
| AU2006284403A1 (en) * | 2005-08-26 | 2007-03-01 | Methylgene Inc. | Benzodiazepine and benzopiperazine analog inhibitors of histone deacetylase |
| US8236535B2 (en) | 2008-04-30 | 2012-08-07 | Xyleco, Inc. | Processing biomass |
| US8212087B2 (en) | 2008-04-30 | 2012-07-03 | Xyleco, Inc. | Processing biomass |
| US7867358B2 (en) | 2008-04-30 | 2011-01-11 | Xyleco, Inc. | Paper products and methods and systems for manufacturing such products |
| CA2722560C (en) | 2008-04-30 | 2019-09-17 | Xyleco, Inc. | Processing biomass |
| BR122017017943B1 (pt) | 2008-10-28 | 2019-11-12 | Xyleco Inc | método de processar um material contendo carboidrato |
| US20240000806A1 (en) * | 2020-11-20 | 2024-01-04 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Methods and materials for inhibiting cb1 activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3821383A (en) * | 1972-07-10 | 1974-06-28 | Ayerst Mckenna & Harrison | Compositions for and a method of treating diabetic complications |
| US4209527A (en) * | 1979-05-16 | 1980-06-24 | Pfizer Inc. | Benzimidazolone derivatives |
| WO1992005160A1 (en) * | 1986-10-30 | 1992-04-02 | Reinhard Sarges | 4-arylsulfonyl-3,4-dihydro-2(1h)-quinoxalinone-1-alkanoic acids, esters, and salts |
-
1986
- 1986-10-30 WO PCT/US1986/002335 patent/WO1992005160A1/en unknown
- 1986-10-30 US US07/424,298 patent/US4940708A/en not_active Expired - Fee Related
-
1987
- 1987-01-27 IE IE287787A patent/IE68851B1/en not_active IP Right Cessation
- 1987-10-16 DE DE8787309160T patent/DE3784835T2/de not_active Expired - Fee Related
- 1987-10-16 EP EP87309160A patent/EP0266102B1/en not_active Expired - Lifetime
- 1987-10-16 ES ES198787309160T patent/ES2046206T3/es not_active Expired - Lifetime
- 1987-10-16 AT AT87309160T patent/ATE86985T1/de active
- 1987-10-22 JP JP62267597A patent/JPS63295566A/ja active Granted
- 1987-10-27 PT PT85998A patent/PT85998B/pt not_active IP Right Cessation
- 1987-10-27 DK DK561487A patent/DK561487A/da not_active Application Discontinuation
-
1993
- 1993-03-18 GR GR930400553T patent/GR3007402T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0536436B2 (en, 2012) | 1993-05-31 |
| WO1992005160A1 (en) | 1992-04-02 |
| ES2046206T3 (es) | 1994-02-01 |
| DE3784835D1 (de) | 1993-04-22 |
| DK561487D0 (da) | 1987-10-27 |
| DK561487A (da) | 1988-08-08 |
| US4940708A (en) | 1990-07-10 |
| DE3784835T2 (de) | 1993-06-24 |
| GR3007402T3 (en, 2012) | 1993-07-30 |
| JPS63295566A (ja) | 1988-12-01 |
| EP0266102A3 (en) | 1989-11-23 |
| IE68851B1 (en) | 1996-07-24 |
| EP0266102A2 (en) | 1988-05-04 |
| EP0266102B1 (en) | 1993-03-17 |
| ATE86985T1 (de) | 1993-04-15 |
| IE872877L (en) | 1988-04-28 |
| PT85998A (en) | 1987-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19970831 |