DD275689A5 - Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid - Google Patents

Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid Download PDF

Info

Publication number: DD275689A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; reaction; methyl; chloro; dioxide
Prior art date: 1987-10-29

Application number

DD88321145A

Other languages

German (de)

English (en)

Inventor

Dieter Binder

Franz Rovenszky

Hubert P Ferber

Original Assignee

��@��@��k��

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.)

1987-10-29

Filing date

1988-10-27

Publication date

1990-01-31

1988-10-27 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1990-01-31 Publication of DD275689A5 publication Critical patent/DD275689A5/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 6
150000002084 enol ethers Chemical class 0.000 title abstract description 15
-1 2-PYRIDYL Chemical class 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
150000001342 alkaline earth metals Chemical class 0.000 claims abstract 2
125000005843 halogen group Chemical group 0.000 claims abstract 2
238000006243 chemical reaction Methods 0.000 claims description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
239000002585 base Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
235000009518 sodium iodide Nutrition 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
230000001133 acceleration Effects 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
229960002202 lornoxicam Drugs 0.000 abstract description 13
OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 abstract description 11
230000003110 anti-inflammatory effect Effects 0.000 abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
229910052740 iodine Inorganic materials 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
125000005207 tetraalkylammonium group Chemical group 0.000 abstract description 2
WLHQHAUOOXYABV-UHFFFAOYSA-N lornoxicam Chemical compound OC=1C=2SC(Cl)=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 WLHQHAUOOXYABV-UHFFFAOYSA-N 0.000 abstract 1
239000003960 organic solvent Substances 0.000 abstract 1
239000000126 substance Substances 0.000 description 11
239000000243 solution Substances 0.000 description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
239000000679 carrageenan Substances 0.000 description 8
235000010418 carrageenan Nutrition 0.000 description 8
229920001525 carrageenan Polymers 0.000 description 8
229940113118 carrageenan Drugs 0.000 description 8
229960002702 piroxicam Drugs 0.000 description 8
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 8
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 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
206010061218 Inflammation Diseases 0.000 description 4
239000000203 mixture Substances 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101710164760 Chlorotoxin Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 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
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 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
QPAKKWCQMHUHNI-GQIQPHNSSA-N chlorotoxin Chemical compound C([C@H]1C(=O)NCC(=O)N2CCC[C@H]2C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H]4CSSC[C@@H](C(N[C@@H](CCSC)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)CNC(=O)CNC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CC(C)C)NC2=O)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC4=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N3)=O)NC(=O)[C@@H](N)CCSC)C1=CC=C(O)C=C1 QPAKKWCQMHUHNI-GQIQPHNSSA-N 0.000 description 1
229960005534 chlorotoxin Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000003304 gavage Methods 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
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000010874 in vitro model Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Epoxy Compounds (AREA)

DD88321145A 1987-10-29 1988-10-27 Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid DD275689A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT285587		1987-10-29

Publications (1)

Publication Number	Publication Date
DD275689A5 true DD275689A5 (de)	1990-01-31

Family

ID=3541372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88321145A DD275689A5 (de)	1987-10-29	1988-10-27	Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid

Country Status (25)

Country	Link
US (1)	US4927821A (ja)
EP (1)	EP0313935B1 (ja)
JP (1)	JP2588598B2 (ja)
KR (1)	KR970011395B1 (ja)
CN (1)	CN1019577B (ja)
AT (1)	ATE109152T1 (ja)
AU (1)	AU613416B2 (ja)
CA (1)	CA1314883C (ja)
CZ (1)	CZ278281B6 (ja)
DD (1)	DD275689A5 (ja)
DE (1)	DE3850845D1 (ja)
DK (1)	DK168384B1 (ja)
ES (1)	ES2056868T3 (ja)
FI (1)	FI86855C (ja)
HU (1)	HU201082B (ja)
IL (1)	IL87951A (ja)
MY (1)	MY103782A (ja)
NO (1)	NO174928C (ja)
NZ (1)	NZ226477A (ja)
PL (1)	PL150950B1 (ja)
SK (1)	SK695188A3 (ja)
SU (1)	SU1591813A3 (ja)
UA (1)	UA5916A1 (ja)
YU (1)	YU48037B (ja)
ZA (1)	ZA887731B (ja)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT399880B (de) *	1992-07-03	1995-08-25	Chem Pharm Forsch Gmbh	Neue thienothiazinderivate, verfahren zu ihrer herstellung und ihre verwendung
EP0658559A1 (de) *	1993-12-14	1995-06-21	Chemisch Pharmazeutische Forschungsgesellschaft m.b.H.	Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als 5-dipoxygenase und Cyclooxygenaseinhibitoren
DE4400867A1 (de) *	1994-01-14	1995-07-20	Nycomed Arzneimittel Gmbh	Neue Thienothiazinderivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung
US5538966A (en) *	1994-01-21	1996-07-23	Alcon Laboratories, Inc.	Carbonic anhydrase inhibitors
US6254057B1 (en) *	1998-10-22	2001-07-03	Integra Dynamics Inc.	Valve control system
AT413944B (de)	2003-05-27	2006-07-15	Binder Eva Dkfm	Verwendung von oxicam-verbindungen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU518216B2 (en) *	1977-09-06	1981-09-17	Hafslund Nycomed Pharma Aktiengesellschaft	Thienothiazine derivatives
DE3371082D1 (de) *	1982-09-09	1987-05-27	Hoffmann La Roche	Thieno(2,3-e)-1,2-thiazine derivatives
US4551452A (en) *	1983-12-21	1985-11-05	Pfizer Inc.	Anti-inflammatory 2-methyl-2H-1,2-benzo-(or -thieno-)thiazine-3-carboxamide 1,1-dioxide derivatives, compositions, and method of use therefor

1988
- 1988-10-06 IL IL87951A patent/IL87951A/xx not_active IP Right Cessation
- 1988-10-06 NZ NZ226477A patent/NZ226477A/xx unknown
- 1988-10-12 MY MYPI88001131A patent/MY103782A/en unknown
- 1988-10-12 NO NO884543A patent/NO174928C/no unknown
- 1988-10-13 CA CA000580051A patent/CA1314883C/en not_active Expired - Fee Related
- 1988-10-14 EP EP88117090A patent/EP0313935B1/de not_active Expired - Lifetime
- 1988-10-14 AT AT88117090T patent/ATE109152T1/de not_active IP Right Cessation
- 1988-10-14 DE DE3850845T patent/DE3850845D1/de not_active Expired - Fee Related
- 1988-10-14 ES ES88117090T patent/ES2056868T3/es not_active Expired - Lifetime
- 1988-10-17 ZA ZA887731A patent/ZA887731B/xx unknown
- 1988-10-18 US US07/262,499 patent/US4927821A/en not_active Expired - Fee Related
- 1988-10-20 CZ CS886951A patent/CZ278281B6/cs unknown
- 1988-10-20 SK SK6951-88A patent/SK695188A3/sk unknown
- 1988-10-25 YU YU199288A patent/YU48037B/sh unknown
- 1988-10-27 DD DD88321145A patent/DD275689A5/de not_active IP Right Cessation
- 1988-10-27 KR KR1019880014013A patent/KR970011395B1/ko not_active Expired - Lifetime
- 1988-10-27 CN CN88107381A patent/CN1019577B/zh not_active Expired
- 1988-10-27 AU AU24403/88A patent/AU613416B2/en not_active Ceased
- 1988-10-27 PL PL1988275523A patent/PL150950B1/pl unknown
- 1988-10-28 FI FI884976A patent/FI86855C/fi not_active IP Right Cessation
- 1988-10-28 HU HU885638A patent/HU201082B/hu not_active IP Right Cessation
- 1988-10-28 SU SU884356752A patent/SU1591813A3/ru active
- 1988-10-28 JP JP63271064A patent/JP2588598B2/ja not_active Expired - Lifetime
- 1988-10-28 DK DK600188A patent/DK168384B1/da not_active Application Discontinuation
- 1988-10-28 UA UA4356752A patent/UA5916A1/uk unknown

Also Published As

Publication number	Publication date
HU201082B (en)	1990-09-28
CN1019577B (zh)	1992-12-23
HUT50837A (en)	1990-03-28
AU613416B2 (en)	1991-08-01
YU199288A (en)	1989-12-31
FI884976L (fi)	1989-04-30
CZ278281B6 (en)	1993-11-17
YU48037B (sh)	1996-10-18
PL150950B1 (en)	1990-07-31
PL275523A1 (en)	1989-06-12
DE3850845D1 (de)	1994-09-01
SK278141B6 (en)	1996-02-07
NO174928C (no)	1994-08-03
MY103782A (en)	1993-09-30
ES2056868T3 (es)	1994-10-16
ATE109152T1 (de)	1994-08-15
FI86855B (fi)	1992-07-15
DK600188A (da)	1989-04-30
EP0313935A3 (en)	1990-10-31
IL87951A (en)	1992-03-29
JPH01149792A (ja)	1989-06-12
CZ695188A3 (en)	1993-07-14
EP0313935B1 (de)	1994-07-27
UA5916A1 (uk)	1994-12-29
NO884543L (no)	1989-05-02
NO884543D0 (no)	1988-10-12
FI86855C (fi)	1992-10-26
SK695188A3 (en)	1996-02-07
FI884976A0 (fi)	1988-10-28
JP2588598B2 (ja)	1997-03-05
NZ226477A (en)	1990-07-26
NO174928B (no)	1994-04-25
DK168384B1 (da)	1994-03-21
EP0313935A2 (de)	1989-05-03
DK600188D0 (da)	1988-10-28
IL87951A0 (en)	1989-03-31
CA1314883C (en)	1993-03-23
US4927821A (en)	1990-05-22
KR970011395B1 (ko)	1997-07-10
SU1591813A3 (ru)	1990-09-07
AU2440388A (en)	1989-05-04
CN1033809A (zh)	1989-07-12
KR890006657A (ko)	1989-06-15
ZA887731B (en)	1989-07-26

Legal Events

Date	Code	Title	Description
1997-08-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2928485A1 (de)	1981-01-29	Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen
EP0114270B1 (de)	1987-04-01	Acylderivate von 1,4:3,6-Dianhydro-hexiten, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0041215A2 (de)	1981-12-09	Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
EP0374095A2 (de)	1990-06-20	Piperidinderivate
DE69718968T2 (de)	2003-10-09	3-(bis-substituierte-phenylmethylen)oxindol-derivate
DE2523103A1 (de)	1976-12-09	Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
DE2362754C2 (de)	1985-11-21	Cyclopropylalkylaminoreste enthaltende Oxazolinverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DD275689A5 (de)	1990-01-31	Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid
EP0087655A1 (de)	1983-09-07	Verfahren zur Herstellung von Acemetacin
DE2242454A1 (de)	1974-03-07	1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2749584A1 (de)	1978-05-18	Ueberbrueckte geminale diphenylpiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0301428A2 (de)	1989-02-01	Benzyldiaminopyrimidin-Derivate und deren Verwendung als Arzneimittel
CH634839A5 (de)	1983-02-28	Pyranochromonderivate und ihre verwendung in arzneimitteln zur behandlung von allergien.
DE2427272C3 (de)	1981-10-01	1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum
DE3925477A1 (de)	1990-02-08	Neue verbindungen der 3-isoxazolidinon-, 2h-1,2-oxazin-3-(4h)-on- und 3-isoxazepinon-serien
DE2917890C2 (ja)	1987-10-29
DE2004301A1 (de)	1970-09-03	Phenylserinderivate
DE2607570A1 (de)	1976-11-11	Triazolobenzocycloalkylthiadiazin- derivate, verfahren zu ihrer herstellung und dieselben enthaltende pharmazeutische praeparate
DE69219588T2 (de)	1998-01-02	Oxaza substituierte phosphine
DE1670539C3 (de)	1975-10-09	Diacylthiamine und Verfahren zu deren Herstellung
DE2831332A1 (de)	1979-02-08	Vinyloxyimino-derivate der 7-aminothiazolyl-acetamidocephalosporansaeure, ihre herstellung und pharmazeutische zusammensetzungen
EP0036992B1 (de)	1982-12-22	Verwendung von S-Benzyl-3-benzylthiopropionthioat in Arzneimitteln
EP0111205B1 (de)	1987-04-01	Acridanon-Derivate
DE68907893T2 (de)	1993-12-23	Neue 1,3,4,-thiadiazolderivate und antigeschwulstmittel, die diese enthalten.
CH638817A5 (de)	1983-10-14	Nicht-glykosidische theophyllin-zucker-derivate und verfahren zu ihrer herstellung.