CA1246066A - Method for the preparation of a pharmaceutically usable benzothiazine dioxide, and an intermediate for use in the method - Google Patents
Method for the preparation of a pharmaceutically usable benzothiazine dioxide, and an intermediate for use in the methodInfo
- Publication number
- CA1246066A CA1246066A CA000464861A CA464861A CA1246066A CA 1246066 A CA1246066 A CA 1246066A CA 000464861 A CA000464861 A CA 000464861A CA 464861 A CA464861 A CA 464861A CA 1246066 A CA1246066 A CA 1246066A
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- dioxide
- methyl
- benzothiazine
- dimethylacetamide
- 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
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- GHNLJDPNIAIWOQ-UHFFFAOYSA-N 2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NC=CC2=C1 GHNLJDPNIAIWOQ-UHFFFAOYSA-N 0.000 title description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims abstract description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012442 inert solvent Substances 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical group CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims 3
- 230000009435 amidation Effects 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
- JAPXKBYCCYOVDH-UHFFFAOYSA-N 2-methyl-1,1-dioxo-1$l^{6},2-benzothiazin-4-ol Chemical compound C1=CC=C2S(=O)(=O)N(C)C=C(O)C2=C1 JAPXKBYCCYOVDH-UHFFFAOYSA-N 0.000 abstract 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 10
- 229960002702 piroxicam Drugs 0.000 description 10
- 238000009835 boiling Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 235000015250 liver sausages Nutrition 0.000 description 2
- -1 methoxyethyl ester Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- YBRHODCMROOROS-UHFFFAOYSA-N 2h-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2SNC(C(=O)O)=CC2=C1 YBRHODCMROOROS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NOCSAAHHSOQRCI-UHFFFAOYSA-N n-pyridin-2-ylformamide Chemical compound O=CNC1=CC=CC=N1 NOCSAAHHSOQRCI-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI833628A FI72317C (fi) | 1983-10-06 | 1983-10-06 | Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-metyl-4-hydroxi-2h-1,2-benzotiazin-1,1-dioxid -3-(n-2-pyridyl)-karboxamid och i foerfarandet anvaendbar mellanprodukt. |
| FI833628 | 1983-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1246066A true CA1246066A (en) | 1988-12-06 |
Family
ID=8517867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000464861A Expired CA1246066A (en) | 1983-10-06 | 1984-10-05 | Method for the preparation of a pharmaceutically usable benzothiazine dioxide, and an intermediate for use in the method |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT387775B (de) |
| BE (1) | BE900758A (de) |
| CA (1) | CA1246066A (de) |
| CS (1) | CS253593B2 (de) |
| DD (1) | DD224594A5 (de) |
| DK (1) | DK154504C (de) |
| ES (1) | ES8505937A1 (de) |
| FI (1) | FI72317C (de) |
| HU (2) | HU195493B (de) |
| IT (1) | IT1218850B (de) |
| NO (1) | NO159275C (de) |
| PL (1) | PL143957B1 (de) |
| PT (1) | PT79326B (de) |
| SE (2) | SE460789B (de) |
| SU (1) | SU1405703A3 (de) |
| YU (2) | YU43381B (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289879A (en) * | 1980-09-29 | 1981-09-15 | Pfizer Inc. | Synthetic method and intermediate for piroxicam |
| JPH08270888A (ja) * | 1995-03-30 | 1996-10-15 | Nec Eng Ltd | 断熱締結機構 |
-
1983
- 1983-10-06 FI FI833628A patent/FI72317C/fi not_active IP Right Cessation
-
1984
- 1984-10-01 NO NO843949A patent/NO159275C/no not_active IP Right Cessation
- 1984-10-02 DK DK471284A patent/DK154504C/da not_active IP Right Cessation
- 1984-10-03 CS CS847493A patent/CS253593B2/cs unknown
- 1984-10-03 HU HU844649A patent/HU195493B/hu unknown
- 1984-10-03 HU HU843746A patent/HU194559B/hu unknown
- 1984-10-04 YU YU1708/84A patent/YU43381B/xx unknown
- 1984-10-04 PT PT79326A patent/PT79326B/pt not_active IP Right Cessation
- 1984-10-04 IT IT22981/84A patent/IT1218850B/it active
- 1984-10-05 CA CA000464861A patent/CA1246066A/en not_active Expired
- 1984-10-05 AT AT0316384A patent/AT387775B/de active
- 1984-10-05 SU SU843805901A patent/SU1405703A3/ru active
- 1984-10-05 ES ES536544A patent/ES8505937A1/es not_active Expired
- 1984-10-05 BE BE0/213782A patent/BE900758A/fr not_active IP Right Cessation
- 1984-10-05 DD DD84268074A patent/DD224594A5/de not_active IP Right Cessation
- 1984-10-05 SE SE8405002A patent/SE460789B/sv not_active IP Right Cessation
- 1984-10-05 PL PL1984249918A patent/PL143957B1/pl unknown
-
1986
- 1986-08-27 YU YU1496/86A patent/YU43603B/xx unknown
-
1989
- 1989-01-24 SE SE8900248A patent/SE464411B/sv not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |