NO854574L - Fremgangsmaate for fremstilling av en ny krystallinsk form av et benzotiazin-dioksyd-salt. - Google Patents

Fremgangsmaate for fremstilling av en ny krystallinsk form av et benzotiazin-dioksyd-salt.

Info

Publication number: NO854574L
Authority: NO; Norway
Prior art keywords: polymorph; solvent; carboxamide; hydroxy; methyl
Prior art date: 1984-11-16

Application number

NO854574A

Other languages

English (en)

Norwegian (no)

Inventor

Robert Lee Robertson

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1984-11-16

Filing date

1985-11-15

Publication date

1986-05-20

1985-11-15 Application filed by Pfizer filed Critical Pfizer

1986-05-20 Publication of NO854574L publication Critical patent/NO854574L/no

Links

238000000034 method Methods 0.000 title claims abstract description 29
150000003839 salts Chemical class 0.000 title description 14
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 abstract description 45
150000002169 ethanolamines Chemical class 0.000 claims abstract description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
239000000047 product Substances 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
238000000862 absorption spectrum Methods 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 7
238000000634 powder X-ray diffraction Methods 0.000 claims description 4
239000003586 protic polar solvent Substances 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
238000010521 absorption reaction Methods 0.000 claims description 3
238000000354 decomposition reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 1
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239000000463 material Substances 0.000 abstract description 7
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239000003435 antirheumatic agent Substances 0.000 abstract description 4
238000002560 therapeutic procedure Methods 0.000 abstract description 2
239000000243 solution Substances 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000003826 tablet Substances 0.000 description 10
239000003814 drug Substances 0.000 description 9
239000004480 active ingredient Substances 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
239000002002 slurry Substances 0.000 description 8
239000000126 substance Substances 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 6
239000000679 carrageenan Substances 0.000 description 6
235000010418 carrageenan Nutrition 0.000 description 6
229920001525 carrageenan Polymers 0.000 description 6
229940113118 carrageenan Drugs 0.000 description 6
239000002178 crystalline material Substances 0.000 description 6
238000004455 differential thermal analysis Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 6
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
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238000004458 analytical method Methods 0.000 description 4
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239000013078 crystal Substances 0.000 description 4
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239000011541 reaction mixture Substances 0.000 description 4
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238000012360 testing method Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
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230000008018 melting Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
206010039073 rheumatoid arthritis Diseases 0.000 description 3
235000019333 sodium laurylsulphate Nutrition 0.000 description 3
238000003860 storage Methods 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
KIRHSGGIMMTVPT-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical class C1=CC=C2S(=O)(=O)NC(C(=O)N)=C(O)C2=C1 KIRHSGGIMMTVPT-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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
229920000881 Modified starch Polymers 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
210000002683 foot Anatomy 0.000 description 2
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238000004128 high performance liquid chromatography Methods 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
238000011835 investigation Methods 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
235000015110 jellies Nutrition 0.000 description 2
239000008274 jelly Substances 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
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239000004570 mortar (masonry) Substances 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000008188 pellet 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
239000003880 polar aprotic solvent Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000007916 tablet composition Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000007704 transition 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
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 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
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
238000004566 IR spectroscopy Methods 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
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
244000062730 Melissa officinalis Species 0.000 description 1
235000010654 Melissa officinalis Nutrition 0.000 description 1
206010030124 Oedema peripheral Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 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
239000001506 calcium phosphate Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
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238000012512 characterization method Methods 0.000 description 1
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238000011109 contamination Methods 0.000 description 1
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229910052802 copper Inorganic materials 0.000 description 1
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235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
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
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
229940102223 injectable solution Drugs 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
239000008101 lactose Substances 0.000 description 1
239000000865 liniment Substances 0.000 description 1
239000007788 liquid 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
239000012528 membrane Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000008183 oral pharmaceutical preparation Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
238000010422 painting Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 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
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 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
230000008961 swelling Effects 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
230000000699 topical effect Effects 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
239000003981 vehicle 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
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L57/00—Protection of pipes or objects of similar shape against external or internal damage or wear
- 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Engineering & Computer Science (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Mechanical Engineering (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Rheumatology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Cosmetics (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)
Steroid Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Crystals, And After-Treatments Of Crystals (AREA)
Saccharide Compounds (AREA)

NO854574A 1984-11-16 1985-11-15 Fremgangsmaate for fremstilling av en ny krystallinsk form av et benzotiazin-dioksyd-salt. NO854574L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/672,028 US4582831A (en)	1984-11-16	1984-11-16	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

Publications (1)

Publication Number	Publication Date
NO854574L true NO854574L (no)	1986-05-20

Family

ID=24696846

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO854574A NO854574L (no)	1984-11-16	1985-11-15	Fremgangsmaate for fremstilling av en ny krystallinsk form av et benzotiazin-dioksyd-salt.

Country Status (28)

Country	Link
US (1)	US4582831A (sv)
EP (1)	EP0182572B1 (sv)
JP (1)	JPS61122284A (sv)
KR (1)	KR870000291B1 (sv)
CN (1)	CN1004001B (sv)
AT (1)	ATE50257T1 (sv)
AU (1)	AU556378B2 (sv)
CA (1)	CA1209572A (sv)
DD (1)	DD242405A5 (sv)
DE (1)	DE3575925D1 (sv)
DK (1)	DK171726B1 (sv)
EG (1)	EG17621A (sv)
ES (1)	ES8701712A1 (sv)
FI (1)	FI82045C (sv)
GR (1)	GR852772B (sv)
HU (1)	HU197899B (sv)
IE (1)	IE58288B1 (sv)
IL (1)	IL77051A (sv)
IN (1)	IN164207B (sv)
MY (1)	MY101984A (sv)
NO (1)	NO854574L (sv)
NZ (1)	NZ214201A (sv)
PH (1)	PH21322A (sv)
PL (1)	PL149466B1 (sv)
PT (1)	PT81490B (sv)
SU (1)	SU1491339A3 (sv)
YU (1)	YU44019B (sv)
ZA (1)	ZA858773B (sv)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5436241A (en) *	1994-01-14	1995-07-25	Bristol-Myers Squibb Company	Topical anti-inflammatory compositions containing piroxicam
US20030068829A1 (en) *	2001-06-25	2003-04-10	Symyx Technologies, Inc.	High throughput crystallographic screening of materials
MY142390A (en)	2002-05-22	2010-11-30	Glaxosmithkline Llc	3' - [(2z)-[1-(3,4-dimethylphenyl)-1,5- dihydro-3- methyl-5-0xo-4h-pyrazol-4- ylidene]hydrazino]-2' -hydroxy -[1,1' -biphenyl]-3-carboxylic acid bis-(monoethanolamine)
ECSP077628A (es) *	2007-05-03	2008-12-30	Smithkline Beechman Corp	Nueva composición farmacéutica
ES2782898T3 (es)	2009-05-29	2020-09-16	Novartis Ag	Métodos de administración de compuestos agonistas de la trombopoyetina
CN102470136B (zh) *	2009-07-29	2013-12-25	内尔维阿诺医学科学有限公司	Plk 抑制剂的盐类
GB0914287D0 (en) *	2009-08-14	2009-09-30	Pci Biotech As	Compositions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3591584A (en) *	1968-08-27	1971-07-06	Pfizer	Benzothiazine dioxides
US4434164A (en) *	1981-06-01	1984-02-28	Pfizer Inc.	Crystalline benzothiazine dioxide salts
IN160683B (sv) *	1981-06-01	1987-07-25	Pfizer
RO88420A (ro) *	1983-04-25	1986-01-30	Pfizer Inc,Us	Procedeu pentru prepararea unor saruri bazice de piroxican depuse pe suporturi farmaceutice

1984
- 1984-11-16 US US06/672,028 patent/US4582831A/en not_active Expired - Lifetime
1985
- 1985-10-16 IN IN866/DEL/85A patent/IN164207B/en unknown
- 1985-11-11 EP EP85308190A patent/EP0182572B1/en not_active Expired - Lifetime
- 1985-11-11 DE DE8585308190T patent/DE3575925D1/de not_active Expired - Fee Related
- 1985-11-11 AT AT85308190T patent/ATE50257T1/de not_active IP Right Cessation
- 1985-11-14 YU YU1785/85A patent/YU44019B/xx unknown
- 1985-11-14 IL IL77051A patent/IL77051A/xx not_active IP Right Cessation
- 1985-11-14 DD DD85282869A patent/DD242405A5/de not_active IP Right Cessation
- 1985-11-14 NZ NZ214201A patent/NZ214201A/xx unknown
- 1985-11-14 CN CN85108245.9A patent/CN1004001B/zh not_active Expired
- 1985-11-14 ES ES548878A patent/ES8701712A1/es not_active Expired
- 1985-11-14 PT PT81490A patent/PT81490B/pt not_active IP Right Cessation
- 1985-11-14 CA CA000495317A patent/CA1209572A/en not_active Expired
- 1985-11-14 PL PL1985256259A patent/PL149466B1/pl unknown
- 1985-11-15 JP JP60256495A patent/JPS61122284A/ja active Granted
- 1985-11-15 IE IE285285A patent/IE58288B1/en not_active IP Right Cessation
- 1985-11-15 SU SU853982430A patent/SU1491339A3/ru active
- 1985-11-15 NO NO854574A patent/NO854574L/no unknown
- 1985-11-15 PH PH33058A patent/PH21322A/en unknown
- 1985-11-15 DK DK527585A patent/DK171726B1/da not_active IP Right Cessation
- 1985-11-15 GR GR852772A patent/GR852772B/el unknown
- 1985-11-15 AU AU49950/85A patent/AU556378B2/en not_active Ceased
- 1985-11-15 ZA ZA858773A patent/ZA858773B/xx unknown
- 1985-11-15 FI FI854512A patent/FI82045C/sv not_active IP Right Cessation
- 1985-11-15 HU HU854374A patent/HU197899B/hu not_active IP Right Cessation
- 1985-11-16 KR KR1019850008577A patent/KR870000291B1/ko not_active IP Right Cessation
- 1985-11-17 EG EG730/85A patent/EG17621A/xx active
1987
- 1987-08-14 MY MYPI87001339A patent/MY101984A/en unknown

Also Published As

Publication number	Publication date
EG17621A (en)	1991-08-30
YU178585A (en)	1987-12-31
MY101984A (en)	1992-02-29
PT81490B (pt)	1988-03-03
ZA858773B (en)	1987-06-24
DK171726B1 (da)	1997-04-14
YU44019B (en)	1990-02-28
IL77051A0 (en)	1986-04-29
PL149466B1 (en)	1990-02-28
PT81490A (en)	1985-12-01
DE3575925D1 (de)	1990-03-15
IE58288B1 (en)	1993-08-25
PL256259A1 (en)	1986-10-07
FI854512A (fi)	1986-05-17
HUT40116A (en)	1986-11-28
ES8701712A1 (es)	1986-12-01
ES548878A0 (es)	1986-12-01
JPS61122284A (ja)	1986-06-10
US4582831A (en)	1986-04-15
KR860004038A (ko)	1986-06-16
SU1491339A3 (ru)	1989-06-30
FI82045C (sv)	1991-01-10
EP0182572B1 (en)	1990-02-07
IE852852L (en)	1986-05-16
CN1004001B (zh)	1989-04-26
NZ214201A (en)	1988-07-28
ATE50257T1 (de)	1990-02-15
GR852772B (sv)	1986-03-14
EP0182572A1 (en)	1986-05-28
CN85108245A (zh)	1986-09-03
JPH0425957B2 (sv)	1992-05-06
FI854512A0 (fi)	1985-11-15
AU556378B2 (en)	1986-10-30
DK527585D0 (da)	1985-11-15
DD242405A5 (de)	1987-01-28
IN164207B (sv)	1989-01-28
IL77051A (en)	1989-03-31
DK527585A (da)	1986-05-17
FI82045B (fi)	1990-09-28
PH21322A (en)	1987-09-28
HU197899B (en)	1989-06-28
CA1209572A (en)	1986-08-12
AU4995085A (en)	1986-05-22
KR870000291B1 (ko)	1987-02-25

Publication	Publication Date	Title
US4434164A (en)	1984-02-28	Crystalline benzothiazine dioxide salts
BRPI0617477A2 (pt)	2011-07-26	mistura de partÍculas cristalinas de laquinimod sàdica, composiÇço, processo de cristalizaÇço de laquinimod sàdica, laquinimod sàdica, e, processo para produzir uma composiÇço farmacÊutica
NO862750L (no)	1987-01-12	Fremgangsmaate for fremstilling av farmakologisk aktive oksindol-derivater.
CN111148729A (zh)	2020-05-12	苯烯莫德的晶型及其用途与制备方法
NZ200800A (en)	1984-12-14	Lysine and arginine salts of piroxicam
EP0173520B1 (en)	1990-01-03	Tricyclic oxindole antiinflammatory agents
NO854574L (no)	1986-05-20	Fremgangsmaate for fremstilling av en ny krystallinsk form av et benzotiazin-dioksyd-salt.
US6703410B1 (en)	2004-03-09	Crystal forms of 3-(2,4-dichlorobenzyl)-2-methyl-n-(pentylsulfonyl)-3h-benzimidazole-5-carboxamide
JPS5951260A (ja)	1984-03-24	Ｎ−フエニルアミジンの製法
US4461768A (en)	1984-07-24	Anti-inflammatory 1,2-benzothiazines
KR19980064287A (ko)	1998-10-07	다형태를 갖는 독사조신 메실레이트의 새로운 형태(제 ii 형)
US4256753A (en)	1981-03-17	4-(2-Pyridylamino)phenylacetic acid derivatives
AU594686B2 (en)	1990-03-15	Process for the preparation of 2-halonicergoline derivatives and their acid addition salts and new 2-halonicergolines
EP0003286A2 (de)	1979-08-08	Ergopeptidalkaloid-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
CZ267092A3 (en)	1993-03-17	Physical form of (r)-3-methoxy-4-\|1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl) indol -3- ylmethyl¨-n-(2-methylphenylsulfonyl)benzamide
US3583983A (en)	1971-06-08	N-benzenesulfonyl-iso-indole carboxamides
DE69225381T2 (de)	1998-09-03	Nootrope Wirkstoffe
NZ199228A (en)	1984-05-31	Imidazolecarboxamide derivatives and pharmaceutical compositions
DD149072A5 (de)	1981-06-24	Verfahren zur herstellung einer neuen rechtsdrehenden bicyclischen thia-diaza-verbindung
NZ209502A (en)	1987-01-23	Benzothiazine dioxide salts
NO151283B (no)	1984-12-03	Analogifremgangsmaate ved fremstilling av terapeutisk aktive nye 5-jod-3-nitro-4-hydroxybenzonitrilsalter