KR850001883B1 - 결정성 벤조티아진 디옥시드 염류의 제조방법 - Google Patents
결정성 벤조티아진 디옥시드 염류의 제조방법Info
- Publication number
- KR850001883B1 KR850001883B1 KR8202425A KR820002425A KR850001883B1 KR 850001883 B1 KR850001883 B1 KR 850001883B1 KR 8202425 A KR8202425 A KR 8202425A KR 820002425 A KR820002425 A KR 820002425A KR 850001883 B1 KR850001883 B1 KR 850001883B1
- Authority
- KR
- South Korea
- Prior art keywords
- benzothiazine
- pyridyl
- hydroxy
- carboxamide
- methyl
- 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 description 8
- GHNLJDPNIAIWOQ-UHFFFAOYSA-N 2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NC=CC2=C1 GHNLJDPNIAIWOQ-UHFFFAOYSA-N 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 8
- 150000002169 ethanolamines Chemical class 0.000 claims description 8
- PGBYMPJXTSIZEC-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-pyridin-2-yl-1,2-benzothiazine-3-carboxamide Chemical compound CN1SC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=N1 PGBYMPJXTSIZEC-UHFFFAOYSA-N 0.000 claims description 7
- -1 amine salt Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- AKVQFPCEGISSHM-UHFFFAOYSA-N 2-hydroxy-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamide Chemical compound ON1S(C2=C(C=C1C(=O)N)C=CC=C2)(=O)=O AKVQFPCEGISSHM-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
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- 239000004480 active ingredient Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 239000000679 carrageenan Substances 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 229940113118 carrageenan Drugs 0.000 description 6
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
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- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 241000700159 Rattus Species 0.000 description 3
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- 239000002260 anti-inflammatory agent Substances 0.000 description 3
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- 239000001506 calcium phosphate Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
- 229940038472 dicalcium phosphate Drugs 0.000 description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- YSMNECAIZNOYOW-UHFFFAOYSA-N 1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)NC(C(=O)N)=CC2=C1 YSMNECAIZNOYOW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 102000009123 Fibrin Human genes 0.000 description 2
- 108010073385 Fibrin Proteins 0.000 description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010030124 Oedema peripheral Diseases 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 229950003499 fibrin Drugs 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 201000003068 rheumatic fever Diseases 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BBOFTHBIXOWDMA-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(N)=O)=C(O)C2=C1 BBOFTHBIXOWDMA-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010015943 Eye inflammation Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
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- 239000003246 corticosteroid Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000002538 magnesium citrate Nutrition 0.000 description 1
- 239000004337 magnesium citrate Substances 0.000 description 1
- 229960005336 magnesium citrate Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26898081A | 1981-06-01 | 1981-06-01 | |
| US268.980 | 1981-06-01 | ||
| US268,980 | 1981-06-01 | ||
| US367,067 | 1982-04-13 | ||
| US06/367,067 US4434164A (en) | 1981-06-01 | 1982-04-13 | Crystalline benzothiazine dioxide salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830010108A KR830010108A (ko) | 1983-12-26 |
| KR850001883B1 true KR850001883B1 (ko) | 1985-12-28 |
Family
ID=26953436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8202425A Expired KR850001883B1 (ko) | 1981-06-01 | 1982-05-31 | 결정성 벤조티아진 디옥시드 염류의 제조방법 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4434164A (enExample) |
| EP (1) | EP0066459B1 (enExample) |
| KR (1) | KR850001883B1 (enExample) |
| AU (1) | AU529386B2 (enExample) |
| BG (1) | BG37377A3 (enExample) |
| CA (1) | CA1209571A (enExample) |
| DD (1) | DD211560A5 (enExample) |
| DE (1) | DE3260718D1 (enExample) |
| DK (1) | DK149024C (enExample) |
| EG (1) | EG15811A (enExample) |
| ES (1) | ES512723A0 (enExample) |
| FI (1) | FI74705C (enExample) |
| GB (1) | GB2101589A (enExample) |
| GR (1) | GR75476B (enExample) |
| HK (1) | HK65386A (enExample) |
| HU (1) | HU189586B (enExample) |
| IE (1) | IE53160B1 (enExample) |
| IL (1) | IL65917A (enExample) |
| MX (1) | MX6984E (enExample) |
| MY (1) | MY8700126A (enExample) |
| NO (1) | NO157979C (enExample) |
| NZ (1) | NZ200801A (enExample) |
| OA (1) | OA07114A (enExample) |
| PH (1) | PH17906A (enExample) |
| PT (1) | PT74977B (enExample) |
| RO (1) | RO84698B (enExample) |
| YU (1) | YU42767B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5913714A (ja) * | 1982-07-13 | 1984-01-24 | Taito Pfizer Kk | 外用消炎鎮痛剤 |
| RO88420A (ro) * | 1983-04-25 | 1986-01-30 | Pfizer Inc,Us | Procedeu pentru prepararea unor saruri bazice de piroxican depuse pe suporturi farmaceutice |
| DE3431588A1 (de) * | 1983-09-12 | 1985-04-04 | Pfizer, Inc., New York, N.Y. | Kristalline benzothiazindioxid-salze und diese enthaltende pharmazeutische zusammensetzungen |
| DE3346526C2 (de) * | 1983-12-22 | 1986-12-11 | A. Nattermann & Cie GmbH, 5000 Köln | Pharmazeutisches Präparat zur therapeutischen Behandlung von rheumatischen Erkrankungen |
| IT1196307B (it) * | 1984-10-22 | 1988-11-16 | Chiesi Farma Spa | Formulazioni farmaceutiche acquose di piroxicam monoidrato |
| US4582831A (en) | 1984-11-16 | 1986-04-15 | Pfizer Inc. | Anti-inflammatory polymorphic monoethanolamine salt of N-(2-pyridyl)-2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide compound, composition, and method of use therefor |
| US4559326A (en) * | 1985-01-31 | 1985-12-17 | Pfizer Inc. | Antiinflammatory compositions and methods |
| US4623486A (en) * | 1985-05-29 | 1986-11-18 | Pfizer Inc. | [4-substituted benzoyloxy]-N-substituted-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides having anti-arthritic activity |
| US4610982A (en) * | 1985-06-03 | 1986-09-09 | Pfizer Inc. | Anti-inflammatory benzo- and thieno-1,2-thiazine-3-carboxamide 1,1-dioxide derivatives, compositions, and method of use therefor |
| KR890001236B1 (ko) * | 1985-10-02 | 1989-04-28 | 화이자 인코포레이티드 | 소염제 조성물의 제조방법 |
| HU200926B (en) * | 1988-10-28 | 1990-09-28 | Egyt Gyogyszervegyeszeti Gyar | Pharmaceutical composition comprising piroxicam and lactose for use in making tablets or capsules |
| IT1247492B (it) * | 1991-04-18 | 1994-12-17 | Francia Farma | Sali ad attivita' antiinfiammatoria, antisettica, detergente e composizioni farmaceutiche |
| IT1283252B1 (it) * | 1996-03-15 | 1998-04-16 | Pulitzer Italiana | Soluzioni di piroxicam iniettabili per via parenterale |
| GB0031107D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| FR2818641B1 (fr) * | 2000-12-21 | 2004-03-05 | Servier Lab | Nouveaux derives de 1,1-dioxo-2h-1,2-benzothiazine 3-carboxamides, leur procede de preparation et les compositions pharmaceutiques que les contiennent |
| KR100446829B1 (ko) * | 2002-02-20 | 2004-09-04 | 한국유나이티드제약 주식회사 | 가용화된 피록시캄을 함유한 확산형 정제의 조성물 및그의 제조방법 |
| ES2622471T5 (es) | 2003-05-22 | 2020-07-23 | United Therapeutics Corp | Compuestos y procedimientos para la administración de análogos de prostaciclina |
| US20050176809A1 (en) * | 2004-02-05 | 2005-08-11 | Rodlen Laboratories, Inc. | Method and compositions for treatment of painful disorders |
| EP1893190A4 (en) * | 2005-04-28 | 2010-07-28 | Theraquest Biosciences Llc | METHODS AND COMPOSITIONS FOR TREATING PAIN |
| US8747897B2 (en) | 2006-04-27 | 2014-06-10 | Supernus Pharmaceuticals, Inc. | Osmotic drug delivery system |
| JP5851691B2 (ja) | 2007-12-17 | 2016-02-03 | ユナイテッド セラピューティクス コーポレーション | リモジュリンの活性成分であるトレプロスチニルを製造する改良方法 |
| US9593061B2 (en) | 2014-10-20 | 2017-03-14 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3591584A (en) | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| US4074048A (en) | 1976-05-10 | 1978-02-14 | Warner-Lambert Company | Process for the preparation of 4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides |
| US4100347A (en) | 1976-06-10 | 1978-07-11 | Pfizer Inc. | 3,4-Dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid-1,1-dioxide |
| DE2756113A1 (de) | 1977-12-16 | 1979-06-21 | Thomae Gmbh Dr K | Neue 4-hydroxy-2h-1,2-benzothiazin- 3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4289879A (en) | 1980-09-29 | 1981-09-15 | Pfizer Inc. | Synthetic method and intermediate for piroxicam |
-
1982
- 1982-04-13 US US06/367,067 patent/US4434164A/en not_active Expired - Lifetime
- 1982-05-26 BG BG056786A patent/BG37377A3/xx unknown
- 1982-05-27 NO NO821767A patent/NO157979C/no not_active IP Right Cessation
- 1982-05-27 HU HU821721A patent/HU189586B/hu unknown
- 1982-05-27 EP EP82302729A patent/EP0066459B1/en not_active Expired
- 1982-05-27 RO RO107688A patent/RO84698B/ro unknown
- 1982-05-27 DE DE8282302729T patent/DE3260718D1/de not_active Expired
- 1982-05-28 IE IE1286/82A patent/IE53160B1/en not_active IP Right Cessation
- 1982-05-28 YU YU1137/82A patent/YU42767B/xx unknown
- 1982-05-28 DK DK241682A patent/DK149024C/da not_active IP Right Cessation
- 1982-05-28 CA CA000403957A patent/CA1209571A/en not_active Expired
- 1982-05-28 OA OA57703A patent/OA07114A/xx unknown
- 1982-05-28 DD DD82240299A patent/DD211560A5/de not_active IP Right Cessation
- 1982-05-30 EG EG304/82A patent/EG15811A/xx active
- 1982-05-31 MX MX8210098U patent/MX6984E/es unknown
- 1982-05-31 AU AU84322/82A patent/AU529386B2/en not_active Expired
- 1982-05-31 KR KR8202425A patent/KR850001883B1/ko not_active Expired
- 1982-05-31 NZ NZ200801A patent/NZ200801A/en unknown
- 1982-05-31 ES ES512723A patent/ES512723A0/es active Granted
- 1982-05-31 PT PT74977A patent/PT74977B/pt unknown
- 1982-05-31 IL IL65917A patent/IL65917A/xx unknown
- 1982-05-31 GR GR68300A patent/GR75476B/el unknown
- 1982-05-31 FI FI821918A patent/FI74705C/fi not_active IP Right Cessation
- 1982-06-01 GB GB08215966A patent/GB2101589A/en not_active Withdrawn
- 1982-06-01 PH PH27387A patent/PH17906A/en unknown
-
1986
- 1986-09-04 HK HK653/86A patent/HK65386A/en not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY126/87A patent/MY8700126A/xx unknown
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