CH594650A5 - Antiinflammatory (1,2)-benzothiazine derivs. prepn. - Google Patents
Antiinflammatory (1,2)-benzothiazine derivs. prepn.Info
- Publication number
- CH594650A5 CH594650A5 CH1620476A CH1620476A CH594650A5 CH 594650 A5 CH594650 A5 CH 594650A5 CH 1620476 A CH1620476 A CH 1620476A CH 1620476 A CH1620476 A CH 1620476A CH 594650 A5 CH594650 A5 CH 594650A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzothiazine
- hydroxy
- dioxide
- carboxamide
- reaction
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 3
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- -1 alkaline-earth metal salts Chemical class 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
- 239000012022 methylating agents Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000001340 alkali metals 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
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- XRXYFCIBSPQECM-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-n-pyridin-2-yl-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound N1S(=O)(=O)C2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=N1 XRXYFCIBSPQECM-UHFFFAOYSA-N 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YSMNECAIZNOYOW-UHFFFAOYSA-N 1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical class C1=CC=C2S(=O)(=O)NC(C(=O)N)=CC2=C1 YSMNECAIZNOYOW-UHFFFAOYSA-N 0.000 description 2
- GHNLJDPNIAIWOQ-UHFFFAOYSA-N 2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NC=CC2=C1 GHNLJDPNIAIWOQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 229910012375 magnesium hydride Inorganic materials 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- FKOSZDBJQBJDIV-UHFFFAOYSA-N 2h-1,2-benzothiazine-3-carboxamide Chemical class C1=CC=C2SNC(C(=O)N)=CC2=C1 FKOSZDBJQBJDIV-UHFFFAOYSA-N 0.000 description 1
- ORULADMPFOUAKH-UHFFFAOYSA-N C(C1=CC=CC=C1)N1S(C2=C(C(=C1C(=O)NC1=NC=CC=C1)O)C=CC=C2)(=O)=O Chemical compound C(C1=CC=CC=C1)N1S(C2=C(C(=C1C(=O)NC1=NC=CC=C1)O)C=CC=C2)(=O)=O ORULADMPFOUAKH-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-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
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 |
|---|---|---|---|
| US64850776A | 1976-01-12 | 1976-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH594650A5 true CH594650A5 (en) | 1978-01-13 |
Family
ID=24601065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1620476A CH594650A5 (en) | 1976-01-12 | 1976-12-22 | Antiinflammatory (1,2)-benzothiazine derivs. prepn. |
Country Status (15)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508042A1 (fr) * | 1981-06-17 | 1982-12-24 | Isom Spa | Procede pour preparer le 4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-(n-(2-pyridinyl) carboxamide)-1,1-dioxide, son ester phosphorique et l'ester phosphorique obtenu |
| EP0336200A1 (en) * | 1988-04-01 | 1989-10-11 | CHIESI FARMACEUTICI S.p.A. | Pharmaceutical compositions of piroxicam in aqueous solutions and process for their preparation |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN160683B (enrdf_load_stackoverflow) * | 1981-06-01 | 1987-07-25 | Pfizer | |
| IN159273B (enrdf_load_stackoverflow) * | 1981-10-05 | 1987-04-25 | Pfizer | |
| DE3217315C2 (de) * | 1982-05-08 | 1986-05-22 | Gödecke AG, 1000 Berlin | Arzneimittelzubereitungen mit einem Gehalt an Oxicam-Derivaten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) * | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
-
1976
- 1976-12-06 SE SE7613691A patent/SE421792B/xx not_active IP Right Cessation
- 1976-12-07 CA CA267,358A patent/CA1069894A/en not_active Expired
- 1976-12-10 AT AT915876A patent/AT349483B/de active
- 1976-12-20 NL NL7614135A patent/NL7614135A/xx not_active Application Discontinuation
- 1976-12-21 JP JP15411376A patent/JPS5293777A/ja active Pending
- 1976-12-22 CH CH1620476A patent/CH594650A5/fr not_active IP Right Cessation
- 1976-12-22 ES ES454502A patent/ES454502A1/es not_active Expired
- 1976-12-22 FI FI763680A patent/FI63231B/fi not_active Application Discontinuation
- 1976-12-22 DK DK579876A patent/DK579876A/da not_active Application Discontinuation
- 1976-12-23 LU LU76466A patent/LU76466A1/xx unknown
- 1976-12-23 AR AR265984A patent/AR210628A1/es active
- 1976-12-29 SU SU762435654A patent/SU634672A3/ru active
- 1976-12-29 HU HU76PI556A patent/HU173509B/hu not_active IP Right Cessation
- 1976-12-30 PL PL1976194854A patent/PL102554B1/pl unknown
- 1976-12-30 DD DD7600196765A patent/DD130145A5/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508042A1 (fr) * | 1981-06-17 | 1982-12-24 | Isom Spa | Procede pour preparer le 4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-(n-(2-pyridinyl) carboxamide)-1,1-dioxide, son ester phosphorique et l'ester phosphorique obtenu |
| EP0336200A1 (en) * | 1988-04-01 | 1989-10-11 | CHIESI FARMACEUTICI S.p.A. | Pharmaceutical compositions of piroxicam in aqueous solutions and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5293777A (en) | 1977-08-06 |
| AR210628A1 (es) | 1977-08-31 |
| NL7614135A (nl) | 1977-07-14 |
| ES454502A1 (es) | 1977-12-01 |
| FI63231B (fi) | 1983-01-31 |
| HU173509B (hu) | 1979-05-28 |
| PL102554B1 (pl) | 1979-04-30 |
| CA1069894A (en) | 1980-01-15 |
| SE421792B (sv) | 1982-02-01 |
| AT349483B (de) | 1979-04-10 |
| LU76466A1 (enrdf_load_stackoverflow) | 1977-07-05 |
| FI763680A7 (enrdf_load_stackoverflow) | 1977-07-13 |
| DK579876A (da) | 1977-07-13 |
| ATA915876A (de) | 1978-09-15 |
| DD130145A5 (de) | 1978-03-08 |
| SU634672A3 (ru) | 1978-11-25 |
| SE7613691L (sv) | 1977-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |