SK73693A3 - Thiazinone derivatives, process for their preparing and their pharmaceutical compositions - Google Patents

Thiazinone derivatives, process for their preparing and their pharmaceutical compositions Download PDF

Info

Publication number: SK73693A3
Authority: SK; Slovakia
Prior art keywords: dihydro; tetrahydroquinolin; formula; dimethyl; ethyl
Prior art date: 1992-07-17

Application number

SK736-93A

Other languages

English (en)

Slovak (sk)

Inventor

Rochus Jonas

Ingeborg Lues

Klaus-Otto Minck

Michael Klockow

Original Assignee

Merck Patent 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.)

1992-07-17

Filing date

1993-07-13

Publication date

1994-04-06

1993-07-13 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1994-04-06 Publication of SK73693A3 publication Critical patent/SK73693A3/sk

Links

238000000034 method Methods 0.000 title claims description 18
230000008569 process Effects 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
HRHFUHGNTSSIFS-UHFFFAOYSA-N 2h-thiazine 1-oxide Chemical class O=S1NC=CC=C1 HRHFUHGNTSSIFS-UHFFFAOYSA-N 0.000 title 1
-1 N-ethyl-4-methoxybenzimidoyl Chemical group 0.000 claims description 137
150000001875 compounds Chemical class 0.000 claims description 75
239000002253 acid Substances 0.000 claims description 37
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GOWMBYUZXIZENX-CAUSLRQDSA-N 1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hexadecylamino)pyrimidin-2-one Chemical compound O=C1N=C(NCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 GOWMBYUZXIZENX-CAUSLRQDSA-N 0.000 claims description 2
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TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
210000001758 mesenteric vein Anatomy 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
ZJUCLOKQDMHWBS-UHFFFAOYSA-N methyl 2-oxo-5-(1,2,3,4-tetrahydroquinolin-6-yl)-6h-1,3,4-thiadiazine-3-carboxylate Chemical compound C1SC(=O)N(C(=O)OC)N=C1C1=CC=C(NCCC2)C2=C1 ZJUCLOKQDMHWBS-UHFFFAOYSA-N 0.000 description 1
WBMXIXVLRHQGPI-UHFFFAOYSA-N methyl 6,6-dimethyl-2-oxo-5-(1,2,3,4-tetrahydroquinolin-6-yl)-1,3,4-thiadiazine-3-carboxylate Chemical compound CC1(C)SC(=O)N(C(=O)OC)N=C1C1=CC=C(NCCC2)C2=C1 WBMXIXVLRHQGPI-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
244000309715 mini pig Species 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
FKJIPSKKDMKKSS-UHFFFAOYSA-N n-[4-(methanesulfonamido)phenyl]-3,4-dimethoxybenzenecarboximidoyl chloride Chemical compound C1=C(OC)C(OC)=CC=C1C(Cl)=NC1=CC=C(NS(C)(=O)=O)C=C1 FKJIPSKKDMKKSS-UHFFFAOYSA-N 0.000 description 1
JMMNLVOIKXIPSP-UHFFFAOYSA-N n-ethyl-2,4-dimethoxybenzenecarboximidoyl chloride Chemical compound CCN=C(Cl)C1=CC=C(OC)C=C1OC JMMNLVOIKXIPSP-UHFFFAOYSA-N 0.000 description 1
QLVSZHXNIBTGAX-UHFFFAOYSA-N n-ethyl-2-methoxybenzenecarboximidoyl chloride Chemical compound CCN=C(Cl)C1=CC=CC=C1OC QLVSZHXNIBTGAX-UHFFFAOYSA-N 0.000 description 1
RZHREWGTKUEFOO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxybenzamide Chemical compound CCNC(=O)C1=CC=C(OC)C(OC)=C1 RZHREWGTKUEFOO-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LTYGNZSVLXJALQ-UHFFFAOYSA-N o-ethyl n-aminocarbamothioate Chemical compound CCOC(=S)NN LTYGNZSVLXJALQ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000010653 organometallic reaction Methods 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- 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
- C07D417/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Quinoline Compounds (AREA)

SK736-93A 1992-07-17 1993-07-13 Thiazinone derivatives, process for their preparing and their pharmaceutical compositions SK73693A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4223537A DE4223537A1 (de)	1992-07-17	1992-07-17	Thiadiazinone

Publications (1)

Publication Number	Publication Date
SK73693A3 true SK73693A3 (en)	1994-04-06

Family

ID=6463436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK736-93A SK73693A3 (en)	1992-07-17	1993-07-13	Thiazinone derivatives, process for their preparing and their pharmaceutical compositions

Country Status (15)

Country	Link
US (1)	US5378702A (fr)
EP (1)	EP0579077A3 (fr)
JP (1)	JPH06179672A (fr)
KR (1)	KR950003291A (fr)
CN (1)	CN1084172A (fr)
AU (1)	AU4194393A (fr)
CA (1)	CA2100622A1 (fr)
CZ (1)	CZ142693A3 (fr)
DE (1)	DE4223537A1 (fr)
HU (1)	HUT66181A (fr)
MX (1)	MX9304283A (fr)
NO (1)	NO932590L (fr)
PL (1)	PL299689A1 (fr)
SK (1)	SK73693A3 (fr)
ZA (1)	ZA935177B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19500558A1 (de) *	1995-01-11	1996-07-18	Merck Patent Gmbh	3-Alkoxycarbonyl-thiadiazinone
KR100480350B1 (ko) *	1999-12-22	2005-04-06	주식회사 포스코	열간직송압연에 의한 고연성 열연강판의 제조방법

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU614965B2 (en) *	1987-06-06	1991-09-19	Merck Patent Gesellschaft Mit Beschrankter Haftung	Thiadiazinones
DE4041074A1 (de) *	1990-12-21	1992-06-25	Merck Patent Gmbh	Thiadiazinonderivate

1992
- 1992-07-17 DE DE4223537A patent/DE4223537A1/de not_active Withdrawn
1993
- 1993-07-05 EP EP19930110698 patent/EP0579077A3/de not_active Withdrawn
- 1993-07-13 SK SK736-93A patent/SK73693A3/sk unknown
- 1993-07-14 AU AU41943/93A patent/AU4194393A/en not_active Abandoned
- 1993-07-15 MX MX9304283A patent/MX9304283A/es unknown
- 1993-07-15 CA CA002100622A patent/CA2100622A1/fr not_active Abandoned
- 1993-07-15 PL PL93299689A patent/PL299689A1/xx unknown
- 1993-07-16 US US08/089,485 patent/US5378702A/en not_active Expired - Fee Related
- 1993-07-16 CZ CZ931426A patent/CZ142693A3/cs unknown
- 1993-07-16 JP JP5176792A patent/JPH06179672A/ja active Pending
- 1993-07-16 NO NO932590A patent/NO932590L/no unknown
- 1993-07-16 ZA ZA935177A patent/ZA935177B/xx unknown
- 1993-07-16 KR KR1019930013505A patent/KR950003291A/ko not_active Withdrawn
- 1993-07-16 HU HU9302058A patent/HUT66181A/hu unknown
- 1993-07-17 CN CN93108544A patent/CN1084172A/zh active Pending

Also Published As

Publication number	Publication date
PL299689A1 (en)	1994-04-05
NO932590L (no)	1994-01-18
NO932590D0 (no)	1993-07-16
US5378702A (en)	1995-01-03
EP0579077A3 (en)	1994-05-18
CA2100622A1 (fr)	1994-01-18
KR950003291A (ko)	1995-02-16
AU4194393A (en)	1994-01-20
JPH06179672A (ja)	1994-06-28
HU9302058D0 (en)	1993-10-28
HUT66181A (en)	1994-09-28
ZA935177B (en)	1994-03-02
CN1084172A (zh)	1994-03-23
CZ142693A3 (en)	1994-02-16
DE4223537A1 (de)	1994-01-20
MX9304283A (es)	1994-02-28
EP0579077A2 (fr)	1994-01-19

Publication	Publication Date	Title
KR930011486B1 (ko)	1993-12-08	제약상 유효한 2-티오메틸-치환-1,4-디히드로피리딘
JP2694535B2 (ja)	1997-12-24	チアジアジノン化合物
US4883800A (en)	1989-11-28	Quinazoline derivatives and process for their production
CZ286567B6 (cs)	2000-05-17	Derivát arylalkyldiazinonu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
US4746664A (en)	1988-05-24	Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent
US5171851A (en)	1992-12-15	Imidazole substituted benzoxazine or benzothiazine derivatives
IE63502B1 (en)	1995-05-03	Aminopyrimidine derivatives useful for treating cardiovascular disorders
US4695567A (en)	1987-09-22	Pyrrolobenzimidazoles, pharmaceutical compositions containing them and method of using them to treat certain heart and circulatory diseases
AU607731B2 (en)	1991-03-14	5-benzoxazinyl-and 6-benzothiazinyl-2,3,4,5 tetrahydropyridazin-3-ones
JP2581556B2 (ja)	1997-02-12	新規なドパミンベ−タヒドロキシラ−ゼ抑制剤
HU193275B (en)	1987-09-28	Process for production of derivatives of dihydripirizin and medical preparatives containing thereof
EP0456835A1 (fr)	1991-11-21	Derive de l'acide quinazoline-3-alcanoique, sels derives de ce compose et sa production
US4766118A (en)	1988-08-23	6-benzoxazinyl- and 6-benzothiazinyl-2,3,4,5-tetrahydropyridazin-3-ones and pharmaceutical use
JPS62240668A (ja)	1987-10-21	１，２，３，４−テトラヒドロ−６−置換−４−アリ−ル（またはヘテロシクロ）−３−置換−２−チオキソ（またはオキソ）−５−ピリミジンカルボン酸類およびエステル類
JPH0641464B2 (ja)	1994-06-01	ジヒドロピリジン類
SK73693A3 (en)	1994-04-06	Thiazinone derivatives, process for their preparing and their pharmaceutical compositions
SK279095B6 (sk)	1998-06-03	Deriváty chrómanu samy osebe a na liečenie chorôb,
US5137885A (en)	1992-08-11	Thiadiazinones
HU201059B (en)	1990-09-28	Process for producing 6-oxo-pyridazine derivatives and pharmaceutical compositions containing them
JPH0196180A (ja)	1989-04-14	ベンゾイミダゾール化合物、その製造法およびこれらの化合物を含有する心機能不全治療用組成物
CA1173831A (fr)	1984-09-04	Methode d'obtention de nouveaux composes polyazaheterocycliques
CA1138870A (fr)	1983-01-04	Obtention et emploi de derives de la 1,2,4-triazine
CZ292094B6 (cs)	2003-07-16	Derivát 3-alkoxykarbonylthiadiazinonu, způsob jeho přípravy jeho použití a farmaceutický prostředek, který ho obsahuje
JPH06157483A (ja)	1994-06-03	１，３，４−ベンゾトリアゼピン−５（４ｈ）−オン誘導体およびその製造法
EP0254064B1 (fr)	1992-06-17	2-(Aminoalkylthio)méthyl-1,4-dihydropyridines, leur procédé de préparation et compositions pharmaceutiques qui les contiennent