DD256701A5 - Verfahren zur herstellung neuer pyrimido (5,4-b) (1,4)-oxozin-derivate - Google Patents

Verfahren zur herstellung neuer pyrimido (5,4-b) (1,4)-oxozin-derivate Download PDF

Info

Publication number: DD256701A5
Authority: DD; German Democratic Republic
Prior art keywords: group; methyl; pyrimido; dihydro; general formula
Prior art date: 1985-12-30

Application number

DD86298832A

Other languages

German (de)

English (en)

Inventor

Kasztreiner

Rabloczky

Makk

Cseh

Kuhar

Diesler

Jaszlits

Sebestyen

Wellmann

Tegdes

Sarossy

Matyus

Varro

Szam

Vegvari

Original Assignee

��@��@��@��@��@��@��Kk��

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.)

1985-12-30

Filing date

1986-12-30

Publication date

1988-05-18

1986-12-30 Application filed by ��@��@��@��@��@��@��Kk�� filed Critical ��@��@��@��@��@��@��Kk��

1988-05-18 Publication of DD256701A5 publication Critical patent/DD256701A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 62
239000001257 hydrogen Substances 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
230000008569 process Effects 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 14
150000002431 hydrogen Chemical group 0.000 claims abstract description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 103
-1 mercapto, aminocarbonyl Chemical group 0.000 claims description 65
239000000203 mixture Substances 0.000 claims description 32
239000002253 acid Chemical group 0.000 claims description 24
239000002585 base Substances 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
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OSNITTCFBARDOQ-UHFFFAOYSA-N 6-amino-2-methyl-4-(2-morpholin-4-ylethyl)-8h-pyrimido[5,4-b][1,4]oxazin-7-one Chemical compound C=12OC(N)C(=O)NC2=NC(C)=NC=1CCN1CCOCC1 OSNITTCFBARDOQ-UHFFFAOYSA-N 0.000 claims description 2
PJDFDTWOSYLCEV-UHFFFAOYSA-N 6-amino-2-methyl-4-(3-morpholin-4-ylpropyl)-8h-pyrimido[5,4-b][1,4]oxazin-7-one Chemical compound C=12OC(N)C(=O)NC2=NC(C)=NC=1CCCN1CCOCC1 PJDFDTWOSYLCEV-UHFFFAOYSA-N 0.000 claims description 2
MBICTDJERCTOAE-UHFFFAOYSA-N 6-amino-4-(2-hydroxyethyl)-2,6-dimethyl-8-(morpholine-4-carbonyl)pyrimido[5,4-b][1,4]oxazin-7-one Chemical compound C12=NC(C)=NC(CCO)=C2OC(C)(N)C(=O)N1C(=O)N1CCOCC1 MBICTDJERCTOAE-UHFFFAOYSA-N 0.000 claims description 2
IDPLZTFGIRGNDA-UHFFFAOYSA-N 6-amino-4-(2-hydroxyethyl)-2-methyl-8-(2-oxopropyl)pyrimido[5,4-b][1,4]oxazin-7-one Chemical compound N1=C(C)N=C2N(CC(=O)C)C(=O)C(N)OC2=C1CCO IDPLZTFGIRGNDA-UHFFFAOYSA-N 0.000 claims description 2
DDMHQMXOMBWJQJ-UHFFFAOYSA-N 7h-pyrimido[4,5-b][1,4]oxazine Chemical class C1=NC=C2N=CCOC2=N1 DDMHQMXOMBWJQJ-UHFFFAOYSA-N 0.000 claims description 2
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125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005936 piperidyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
ILUNDTRLPGTHKB-UHFFFAOYSA-N 6-amino-4-[(4-benzylmorpholin-2-yl)methyl]-2-methyl-8h-pyrimido[5,4-b][1,4]oxazin-7-one Chemical compound C=12OC(N)C(=O)NC2=NC(C)=NC=1CC(OCC1)CN1CC1=CC=CC=C1 ILUNDTRLPGTHKB-UHFFFAOYSA-N 0.000 claims 1
HYJJQDSQIFRAPL-UHFFFAOYSA-N C(C1=CC=CC=C1)N1C2=C(OC(C1=O)N)C(=NC(=N2)C)CCO Chemical compound C(C1=CC=CC=C1)N1C2=C(OC(C1=O)N)C(=NC(=N2)C)CCO HYJJQDSQIFRAPL-UHFFFAOYSA-N 0.000 claims 1
UHBOQGMXEKOHEA-UHFFFAOYSA-N N1=C(C)N=C2N(C(=O)OCCCC)C(=O)C(C)(N)OC2=C1CCO Chemical compound N1=C(C)N=C2N(C(=O)OCCCC)C(=O)C(C)(N)OC2=C1CCO UHBOQGMXEKOHEA-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
YKYTWPWRNOKOBY-UHFFFAOYSA-N ethyl 2-(4-amino-2-methyl-7-oxopyrimido[5,4-b][1,4]oxazin-8-yl)acetate Chemical compound N1=C(C)N=C2N(CC(=O)OCC)C(=O)COC2=C1N YKYTWPWRNOKOBY-UHFFFAOYSA-N 0.000 claims 1
SVPDQLMHTJPXGW-UHFFFAOYSA-N ethyl 2-[6-amino-4-(2-hydroxyethyl)-2-methyl-7-oxopyrimido[5,4-b][1,4]oxazin-8-yl]acetate Chemical compound C(C)OC(=O)CN1C2=C(OC(C1=O)N)C(=NC(=N2)C)CCO SVPDQLMHTJPXGW-UHFFFAOYSA-N 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
150000004896 1,4-oxazines Chemical class 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
239000000243 solution Substances 0.000 description 46
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230000000694 effects Effects 0.000 description 38
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000003756 stirring Methods 0.000 description 24
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
239000002244 precipitate Substances 0.000 description 20
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230000009090 positive inotropic effect Effects 0.000 description 6
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RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 5
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150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005414 pirbuterol Drugs 0.000 description 1
229960004358 prenalterol Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
210000001147 pulmonary artery Anatomy 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
210000005241 right ventricle Anatomy 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
210000000518 sarcolemma Anatomy 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
XMFCOYRWYYXZMY-UHFFFAOYSA-N sulmazole Chemical compound COC1=CC(S(C)=O)=CC=C1C1=NC2=NC=CC=C2N1 XMFCOYRWYYXZMY-UHFFFAOYSA-N 0.000 description 1
229950006153 sulmazole Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

DD86298832A 1985-12-30 1986-12-30 Verfahren zur herstellung neuer pyrimido (5,4-b) (1,4)-oxozin-derivate DD256701A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU855042A HU195822B (en)	1985-12-30	1985-12-30	Process for producing new pyrimido/5,4-b//1,h/oxazine derivatives

Publications (1)

Publication Number	Publication Date
DD256701A5 true DD256701A5 (de)	1988-05-18

Family

ID=10969567

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86298832A DD256701A5 (de)	1985-12-30	1986-12-30	Verfahren zur herstellung neuer pyrimido (5,4-b) (1,4)-oxozin-derivate

Country Status (20)

Country	Link
US (1)	US4748175A (cs)
EP (1)	EP0228094B1 (cs)
JP (1)	JPS62228082A (cs)
CN (1)	CN1021734C (cs)
AT (1)	ATE66232T1 (cs)
AU (1)	AU586380B2 (cs)
CA (1)	CA1287052C (cs)
CS (1)	CS268822B2 (cs)
DD (1)	DD256701A5 (cs)
DE (1)	DE3680893D1 (cs)
DK (1)	DK630186A (cs)
ES (1)	ES2003643A6 (cs)
FI (1)	FI82469C (cs)
GR (1)	GR862962B (cs)
HU (1)	HU195822B (cs)
IL (1)	IL81117A (cs)
NO (1)	NO170935C (cs)
NZ (1)	NZ218795A (cs)
SU (2)	SU1567122A3 (cs)
YU (1)	YU46039B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5067754A (en)	1980-10-29	1991-11-26	Propietary Technology, Inc.	Swivelable quick connector assembly
CA1331178C (en) *	1988-02-05	1994-08-02	James J. Wade	Triazolo ¬1,5-c\| pyrimido ¬1,4\| azines as bronchodilators
GB2359551A (en) *	2000-02-23	2001-08-29	Astrazeneca Uk Ltd	Pharmaceutically active pyrimidine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4215216A (en) *	1979-04-18	1980-07-29	American Home Products Corporation	7,8-Dihydro-2,5,8-trisubstituted-7-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid derivatives

1985
- 1985-12-30 HU HU855042A patent/HU195822B/hu not_active IP Right Cessation
1986
- 1986-12-23 NZ NZ218795A patent/NZ218795A/xx unknown
- 1986-12-29 DK DK630186A patent/DK630186A/da not_active Application Discontinuation
- 1986-12-30 CA CA000526548A patent/CA1287052C/en not_active Expired - Lifetime
- 1986-12-30 ES ES8603622A patent/ES2003643A6/es not_active Expired
- 1986-12-30 SU SU864028913A patent/SU1567122A3/ru active
- 1986-12-30 DE DE8686118122T patent/DE3680893D1/de not_active Expired - Lifetime
- 1986-12-30 AT AT86118122T patent/ATE66232T1/de not_active IP Right Cessation
- 1986-12-30 US US06/947,700 patent/US4748175A/en not_active Expired - Fee Related
- 1986-12-30 DD DD86298832A patent/DD256701A5/de not_active IP Right Cessation
- 1986-12-30 FI FI865344A patent/FI82469C/fi not_active IP Right Cessation
- 1986-12-30 YU YU227986A patent/YU46039B/sh unknown
- 1986-12-30 CS CS8610262A patent/CS268822B2/cs unknown
- 1986-12-30 CN CN86108914A patent/CN1021734C/zh not_active Expired - Fee Related
- 1986-12-30 GR GR862962A patent/GR862962B/el unknown
- 1986-12-30 AU AU67043/86A patent/AU586380B2/en not_active Ceased
- 1986-12-30 IL IL81117A patent/IL81117A/xx not_active IP Right Cessation
- 1986-12-30 NO NO865347A patent/NO170935C/no unknown
- 1986-12-30 EP EP86118122A patent/EP0228094B1/de not_active Expired - Lifetime
1987
- 1987-01-05 JP JP62000083A patent/JPS62228082A/ja active Pending
1988
- 1988-06-14 SU SU884355907A patent/SU1567123A3/ru active

Also Published As

Publication number	Publication date
FI82469B (fi)	1990-11-30
EP0228094A3 (en)	1988-10-12
YU46039B (sh)	1992-12-21
NO170935C (no)	1992-12-30
FI865344A7 (fi)	1987-07-01
NO170935B (no)	1992-09-21
FI82469C (fi)	1991-03-11
HU195822B (en)	1988-07-28
HUT44032A (en)	1988-01-28
CN1021734C (zh)	1993-08-04
SU1567123A3 (ru)	1990-05-23
IL81117A (en)	1990-07-12
CS1026286A2 (en)	1989-08-14
JPS62228082A (ja)	1987-10-06
AU586380B2 (en)	1989-07-06
FI865344A0 (fi)	1986-12-30
CN86108914A (zh)	1987-09-30
US4748175A (en)	1988-05-31
NO865347L (no)	1987-07-01
DK630186A (da)	1987-07-01
EP0228094B1 (de)	1991-08-14
AU6704386A (en)	1987-07-02
CA1287052C (en)	1991-07-30
SU1567122A3 (ru)	1990-05-23
GR862962B (en)	1987-05-05
IL81117A0 (en)	1987-03-31
ES2003643A6 (es)	1988-11-01
CS268822B2 (en)	1990-04-11
NZ218795A (cs)	1989-02-24
DE3680893D1 (de)	1991-09-19
DK630186D0 (da)	1986-12-29
YU227986A (en)	1988-02-29
EP0228094A2 (de)	1987-07-08
ATE66232T1 (de)	1991-08-15

Legal Events

Date	Code	Title	Description
1995-12-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69824632T2 (de)	2005-06-09	Purinderivate und medikamente, welche dieselben als aktiven bestandteil enthalten
EP1040101B1 (de)	2007-04-25	Substituierte 2-aryl-4-amino-chinazoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE69107215T2 (de)	1995-05-24	(2-imidazolin-2-ylamino)chinoxalinderivate und methoden in ihrer anwendung.
EP0366061A1 (de)	1990-05-02	Die Verwendung von 4H-1-Benzopyran-4-on-Derivaten, neue 4H-1-Benzopyran-4-on-Derivate und diese enthaltende Arzneimittel
DE19836697A1 (de)	2000-02-17	Substituierte 4-Amino-2-aryl-pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE10323345A1 (de)	2004-12-16	Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren
DD139855A5 (de)	1980-01-23	Verfahren zur herstellung von xanthinderivaten
DE3685604T2 (de)	1993-01-28	1,7-naphthyridinderivate und diese enthaltende arzneimittel.
DD159071A5 (de)	1983-02-16	Verfahren zur darstellung von pyridoxinderivaten und ihre verwendung in therapeutica
DE102004057645A1 (de)	2006-06-01	Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen
DE68925270T2 (de)	1996-06-13	Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel
DE3717080C2 (de)	1996-02-08	1-(Hydroxystyryl)-5H-2,3-benzodiazepinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DD201305A5 (de)	1983-07-13	Verfahren zur herstellung von in 7-stellung substituierten benzopyranen
DE2804519C2 (cs)	1990-06-13
EP1176144A1 (de)	2002-01-30	Neue N-Triazolylmethyl-Piperazinderivate als Neurokininrezeptor-Antagonisten
EP0665228B1 (de)	1999-07-14	Neue 3-Phenylsulfonyl-3,7-diazabicyclo(3,3,1)nonan-Verbindungen enthaltende Arzneimittel
EP1678130B1 (de)	2008-08-20	Amidomethyl-substituierte 2-(4-sulfonilamino)-3-hidroxy-3,4-dihydro- 2h-chromen-6-yl-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4661484A (en)	1987-04-28	Pyridazinone derivatives and salts thereof as cardiac stimulants
DE60202969T2 (de)	2006-01-19	Substituierte alkylaminopyridazinonderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
DD256701A5 (de)	1988-05-18	Verfahren zur herstellung neuer pyrimido (5,4-b) (1,4)-oxozin-derivate
CH637391A5 (de)	1983-07-29	Therapeutisch wirksame 3-(1-piperazinyl)-1,2,4-benzotriazine und ihre n-oxide.
DE2322313A1 (de)	1973-11-22	Pyrazolderivate und verfahren zu ihrer herstellung
EP0075165B1 (de)	1986-10-29	9,10-Substituierte 2-Mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2H-pyrimido(6,1-a)isochinolin-4-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0180833B1 (de)	1989-07-19	4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel
DE69229501T2 (de)	1999-11-18	Benzopyranderivat und dieses als aktives bestandteil enthaltendes antiallergikum