BE896434A - Procede pour la preparation de 4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxydes et produits obtenus - Google Patents
Procede pour la preparation de 4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxydes et produits obtenus Download PDFInfo
- Publication number
- BE896434A BE896434A BE0/210531A BE210531A BE896434A BE 896434 A BE896434 A BE 896434A BE 0/210531 A BE0/210531 A BE 0/210531A BE 210531 A BE210531 A BE 210531A BE 896434 A BE896434 A BE 896434A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- methyl
- hydroxy
- formula
- benzothiazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- -1 5-methyl-isoxazolyl Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- RQRCJRUUPFZABV-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2C(O)=C(C(O)=O)N(C)SC2=C1 RQRCJRUUPFZABV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BBOFTHBIXOWDMA-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical class C1=CC=C2S(=O)(=O)N(C)C(C(N)=O)=C(O)C2=C1 BBOFTHBIXOWDMA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002681 magnesium compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- YGURAIHQUYQFTL-UHFFFAOYSA-M [Br-].NC1=NC=CC=C1[Mg+] Chemical compound [Br-].NC1=NC=CC=C1[Mg+] YGURAIHQUYQFTL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MMUOSHJTMPKNJN-UHFFFAOYSA-N ethyl 4-hydroxy-2-methyl-1,2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2SN(C)C(C(=O)OCC)=C(O)C2=C1 MMUOSHJTMPKNJN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- HCBYBSNVNNNJFJ-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2SN(C)C(C(=O)OC)=C(O)C2=C1 HCBYBSNVNNNJFJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES511472A ES511472A0 (es) | 1982-04-16 | 1982-04-16 | "procedimiento para la obtencion del 4-hidroxi-2-metil-n-(2-piridil)-2h-1,2-benzotiazina-3-carboxamida-1,1-dioxido". |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE896434A true BE896434A (fr) | 1983-08-01 |
Family
ID=8484012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/210531A BE896434A (fr) | 1982-04-16 | 1983-04-12 | Procede pour la preparation de 4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxydes et produits obtenus |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6044305B2 (es) |
| BE (1) | BE896434A (es) |
| ES (1) | ES511472A0 (es) |
-
1982
- 1982-04-16 ES ES511472A patent/ES511472A0/es active Granted
-
1983
- 1983-03-22 JP JP58048607A patent/JPS6044305B2/ja not_active Expired
- 1983-04-12 BE BE0/210531A patent/BE896434A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES8300760A1 (es) | 1982-12-01 |
| ES511472A0 (es) | 1982-12-01 |
| JPS58201772A (ja) | 1983-11-24 |
| JPS6044305B2 (ja) | 1985-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: MEDICHEM S.A. Effective date: 20010430 |