SK695188A3 - Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent - Google Patents

Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent Download PDF

Info

Publication number: SK695188A3
Authority: SK; Slovakia
Prior art keywords: pyridyl; methyl; carboxylic acid; chloro; dioxo
Prior art date: 1987-10-29

Application number

SK6951-88A

Other languages

English (en)

Slovak (sk)

Other versions

SK278141B6 (en

Inventor

Dieter Binder

Franz Rovenszky

Hubert P Ferber

Original Assignee

Chem Pharm Forsch Gmbh

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

1988-10-20

Publication date

1996-02-07

1988-10-20 Application filed by Chem Pharm Forsch Gmbh filed Critical Chem Pharm Forsch Gmbh

1996-02-07 Publication of SK278141B6 publication Critical patent/SK278141B6/sk

1996-02-07 Publication of SK695188A3 publication Critical patent/SK695188A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 14
-1 Enolether amide Chemical class 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title description 5
239000008177 pharmaceutical agent Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 22
150000002084 enol ethers Chemical class 0.000 claims abstract description 14
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 16
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
239000002585 base Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 7
235000009518 sodium iodide Nutrition 0.000 claims description 7
229940100198 alkylating agent Drugs 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000007810 chemical reaction solvent Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000008041 alkali metal carbonates Chemical class 0.000 claims 1
239000003880 polar aprotic solvent Substances 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
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
229960002702 piroxicam Drugs 0.000 description 11
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 9
239000000243 solution Substances 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
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
239000000203 mixture Substances 0.000 description 7
238000012360 testing method Methods 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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
206010061218 Inflammation Diseases 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
230000004054 inflammatory process Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000126 substance Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
239000000499 gel Substances 0.000 description 3
210000000548 hind-foot Anatomy 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
238000000967 suction filtration Methods 0.000 description 3
230000008961 swelling Effects 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
BNNNRTHFDVJELR-UHFFFAOYSA-N 2h-thiazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CSN1 BNNNRTHFDVJELR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 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
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
HIHUVROYMLDGIT-UHFFFAOYSA-N 2H-thieno[2,3-e]thiazine-3-carboxylic acid Chemical compound S1NC(=CC2=C1C=CS2)C(=O)O HIHUVROYMLDGIT-UHFFFAOYSA-N 0.000 description 1
YBRHODCMROOROS-UHFFFAOYSA-N 2h-1,2-benzothiazine-3-carboxylic acid Chemical compound C1=CC=C2SNC(C(=O)O)=CC2=C1 YBRHODCMROOROS-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000002775 capsule Substances 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
150000001768 cations Chemical class 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
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
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
238000010874 in vitro model Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000000116 mitigating effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 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
238000012545 processing Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium 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
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
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 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
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010626 work up procedure Methods 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)

SK6951-88A 1987-10-29 1988-10-20 Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent SK695188A3 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
SK278141B6 SK278141B6 (en)	1996-02-07
SK695188A3 true SK695188A3 (en)	1996-02-07

Family

ID=3541372

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK6951-88A SK695188A3 (en)	1987-10-29	1988-10-20	Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent

Country Status (25)

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

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
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
DD275689A5 (de)	1990-01-31
ZA887731B (en)	1989-07-26

Publication	Publication Date	Title
SU1375127A3 (ru)	1988-02-15	Способ получени производных 1,2-диаминоциклобутен-3,4-диона или их хлоргидратов
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AT392790B (de)	1991-06-10	Verfahren zur herstellung von neuen 2,3-dihydro-2-oxo-1h-imidazo-(4,5-b)-chinolinyletherderivaten und den pharmazeutisch vertraeglichen salzen davon
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DE69716904T2 (de)	2003-07-24	Neue verbindungen
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DE3222779C2 (da)	1991-01-03
JPS6350355B2 (da)	1988-10-07
CS221527B2 (en)	1983-04-29	Method of preparation of n-/1-methyl-2-pyrrolidinylmethyl/2,3-dimethoxy-5-methylsulphamoylbenzamide
US4156009A (en)	1979-05-22	Diazepine derivatives
SU1001855A3 (ru)	1983-02-28	Способ получени 2-замещенных-1н-фенантро[9,10- @ ]имидазолов или их солей
DE68907893T2 (de)	1993-12-23	Neue 1,3,4,-thiadiazolderivate und antigeschwulstmittel, die diese enthalten.
EP0158083A2 (de)	1985-10-16	Arzneimittel
JPS6125035B2 (da)	1986-06-13
JPS58170779A (ja)	1983-10-07	ピリジン誘導体
HRP940826A2 (en)	1997-04-30	PROCESS FOR THE PREPARATION OF ENOLETHERS OF 6-CHLORO-4-HYDROXY-2-METHYL-N-(2-PYRIDYL)-2H-THIENO(2,3-e)-1,2-thiazin-3-CARBOXYLIC ACID AMIDE-1,1-DIOXIDE