DD202013A5 - Verfahren zur herstellung basisch substituierter pyridazine - Google Patents

Verfahren zur herstellung basisch substituierter pyridazine Download PDF

Info

Publication number: DD202013A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; atoms; general formula; formula; compound
Prior art date: 1980-12-22

Application number

DD81235901A

Other languages

German (de)

English (en)

Inventor

Thomas Raabe

Helmut Bohn

Piero A Martorana

Rolf-Eberhard Nitz

Original Assignee

Cassella Ag

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.)

1980-12-22

Filing date

1981-12-17

Publication date

1983-08-24

1981-12-17 Application filed by Cassella Ag filed Critical Cassella Ag

1983-08-24 Publication of DD202013A5 publication Critical patent/DD202013A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000004519 manufacturing process Methods 0.000 title description 3
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title description 2
-1 morpholino, piperidino Chemical group 0.000 claims abstract description 96
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 42
239000000460 chlorine Substances 0.000 claims abstract description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052794 bromium Inorganic materials 0.000 claims abstract description 16
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
150000004892 pyridazines Chemical class 0.000 claims abstract description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 6
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
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239000002253 acid Substances 0.000 claims description 28
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239000007858 starting material Substances 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
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238000002360 preparation method Methods 0.000 claims description 8
238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
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125000001424 substituent group Chemical group 0.000 claims description 6
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125000004429 atom Chemical group 0.000 claims description 3
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
235000015320 potassium carbonate Nutrition 0.000 description 6
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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150000004985 diamines Chemical class 0.000 description 4
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125000005263 alkylenediamine group Chemical group 0.000 description 3
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 2
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TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
229940097320 beta blocking agent Drugs 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004301 calcium benzoate Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000003943 catecholamines Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
229960002155 chlorothiazide Drugs 0.000 description 1
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229960001076 chlorpromazine Drugs 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
230000003205 diastolic effect Effects 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
229960003602 guanethidine Drugs 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000009249 intrinsic sympathomimetic activity Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000000936 membranestabilizing effect Effects 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
239000008267 milk Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 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
229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000036316 preload Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-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
229960001404 quinidine Drugs 0.000 description 1
229940080360 rauwolfia alkaloid Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
150000003512 tertiary amines Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940099259 vaseline 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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
General Health & Medical Sciences (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

DD81235901A 1980-12-22 1981-12-17 Verfahren zur herstellung basisch substituierter pyridazine DD202013A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19803048487 DE3048487A1 (de)	1980-12-22	1980-12-22	Basisch substituierte pyridazine, ihre herstellung und ihre verwendung

Publications (1)

Publication Number	Publication Date
DD202013A5 true DD202013A5 (de)	1983-08-24

Family

ID=6119960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81235901A DD202013A5 (de)	1980-12-22	1981-12-17	Verfahren zur herstellung basisch substituierter pyridazine

Country Status (26)

Country	Link
US (1)	US4532239A (fr)
EP (1)	EP0054946B1 (fr)
JP (1)	JPS57128677A (fr)
KR (1)	KR880002233B1 (fr)
AT (1)	ATE8991T1 (fr)
AU (1)	AU544386B2 (fr)
CA (1)	CA1173033A (fr)
CS (1)	CS236665B2 (fr)
DD (1)	DD202013A5 (fr)
DE (2)	DE3048487A1 (fr)
DK (1)	DK149810C (fr)
ES (3)	ES8304941A1 (fr)
FI (1)	FI73418C (fr)
GR (1)	GR81382B (fr)
HK (1)	HK51485A (fr)
IE (1)	IE51985B1 (fr)
IL (1)	IL64605A (fr)
NO (1)	NO814182L (fr)
NZ (1)	NZ198919A (fr)
PH (1)	PH17529A (fr)
PL (3)	PL137150B1 (fr)
PT (1)	PT74185B (fr)
RO (3)	RO88190B (fr)
SG (1)	SG7585G (fr)
SU (2)	SU1170970A3 (fr)
ZA (1)	ZA818806B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3023369A1 (de) *	1980-06-23	1982-01-14	Boehringer Mannheim Gmbh, 6800 Mannheim	Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPH0641454B2 (ja) *	1985-02-27	1994-06-01	日産化学工業株式会社	ピリダジノン誘導体
EP0201765B1 (fr) *	1985-04-27	1991-09-18	Nissan Chemical Industries Ltd.	3 (2H) Pyridazinones, procédé de préparation et agents antiallergiques les contenant
JPS61282194A (ja) *	1985-06-06	1986-12-12	Yukio Nakamura	ジエツト推進式舟艇の推進軸とその製造法
JPH0629254B2 (ja) *	1986-09-08	1994-04-20	帝国臓器製薬株式会社	ピリダジノン誘導体
DE3902316A1 (de) *	1989-01-26	1990-08-02	Lentia Gmbh	Neue piperazinylalkyl-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung als blutdrucksenkende mittel
NZ234087A (en) *	1989-06-19	1991-08-27	Teikoku Hormone Mfg Co Ltd	2-(3-aryloxy(2-hydroxy-propylamino))-2-methylpropyl- aminophenyl pyridazine derivatives
US5221674A (en) *	1989-06-19	1993-06-22	Teikoku Hormone Mfg. Co., Ltd.	Pyridazinone derivatives
HU214320B (hu) *	1991-12-20	1998-03-02	EGIS Gyógyszergyár Rt.	Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására
SK18492000A3 (sk)	1998-06-05	2001-06-11	Egis Gy�Gyszergy�R Rt.	Spôsob prípravy 3(2h)-pyridazinón-4-substituovaných amino-5-chlórderivátov
CN101730692A (zh) *	2007-03-15	2010-06-09	先灵公司	用作葡聚糖合成酶抑制剂的哒嗪酮衍生物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES373606A1 (es) *	1968-11-18	1972-06-01	Pfizer	Un procedimiento para la preparacion de nuevos derivados depropanolamina.
GB1421999A (en) *	1973-02-08	1976-01-21	Smith Kline French Lab	Heterocyclic containing sulphoxides
US4115575A (en) *	1973-02-20	1978-09-19	Ciba-Geigy Corporation	2-(3-Amino-2-hydroxy-propoxy)-pyrazines
GB1488330A (en) *	1973-12-19	1977-10-12	Smith Kline French Lab	Dihydropyridazinones
US4088764A (en) *	1973-12-27	1978-05-09	Cassella Farbwerke Mainkur Aktiengesellschaft	Pharmaceutically active derivatives of 1-phenoxy-3-amino-propan-2-ol
CH594626A5 (fr) *	1974-05-14	1978-01-13	Ciba Geigy Ag
LU77339A1 (fr) *	1977-05-16	1979-01-19
DD146749A3 (de) *	1977-12-01	1981-03-04	Dieter Lehmann	Verfahren zur herstellung von phenoxyalkanolamin-derivaten
DE3023369A1 (de) *	1980-06-23	1982-01-14	Boehringer Mannheim Gmbh, 6800 Mannheim	Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1980
- 1980-12-22 DE DE19803048487 patent/DE3048487A1/de not_active Withdrawn
1981
- 1981-11-10 NZ NZ198919A patent/NZ198919A/xx unknown
- 1981-12-07 CA CA000391595A patent/CA1173033A/fr not_active Expired
- 1981-12-08 FI FI813941A patent/FI73418C/fi not_active IP Right Cessation
- 1981-12-08 NO NO814182A patent/NO814182L/no unknown
- 1981-12-08 DK DK542881A patent/DK149810C/da not_active IP Right Cessation
- 1981-12-17 CS CS819455A patent/CS236665B2/cs unknown
- 1981-12-17 DD DD81235901A patent/DD202013A5/de unknown
- 1981-12-18 PL PL1981238537A patent/PL137150B1/pl unknown
- 1981-12-18 PL PL1981234312A patent/PL136127B1/pl unknown
- 1981-12-18 PL PL1981238538A patent/PL137106B1/pl unknown
- 1981-12-19 EP EP81110620A patent/EP0054946B1/fr not_active Expired
- 1981-12-19 DE DE8181110620T patent/DE3165595D1/de not_active Expired
- 1981-12-19 AT AT81110620T patent/ATE8991T1/de not_active IP Right Cessation
- 1981-12-21 IE IE3014/81A patent/IE51985B1/en unknown
- 1981-12-21 RO RO113111A patent/RO88190B/ro unknown
- 1981-12-21 GR GR66860A patent/GR81382B/el unknown
- 1981-12-21 RO RO106060A patent/RO84277B/ro unknown
- 1981-12-21 IL IL64605A patent/IL64605A/xx unknown
- 1981-12-21 ZA ZA818806A patent/ZA818806B/xx unknown
- 1981-12-21 JP JP56205363A patent/JPS57128677A/ja active Pending
- 1981-12-21 KR KR1019810005043A patent/KR880002233B1/ko not_active Expired
- 1981-12-21 AU AU78704/81A patent/AU544386B2/en not_active Ceased
- 1981-12-21 SU SU813367148A patent/SU1170970A3/ru active
- 1981-12-21 RO RO113112A patent/RO88201B/ro unknown
- 1981-12-21 PH PH26659A patent/PH17529A/en unknown
- 1981-12-22 PT PT74185A patent/PT74185B/pt unknown
- 1981-12-22 ES ES508274A patent/ES8304941A1/es not_active Expired
1982
- 1982-08-20 SU SU823478901A patent/SU1151204A3/ru active
- 1982-12-13 ES ES518138A patent/ES8400096A1/es not_active Expired
- 1982-12-13 ES ES518139A patent/ES8308859A1/es not_active Expired
1983
- 1983-12-20 US US06/563,538 patent/US4532239A/en not_active Expired - Fee Related
1985
- 1985-01-26 SG SG75/85A patent/SG7585G/en unknown
- 1985-07-04 HK HK514/85A patent/HK51485A/xx unknown

Also Published As

Publication number	Publication date
HK51485A (en)	1985-07-12
EP0054946A1 (fr)	1982-06-30
DE3048487A1 (de)	1982-07-29
FI813941L (fi)	1982-06-23
RO88190B (ro)	1985-12-31
NZ198919A (en)	1985-05-31
AU7870481A (en)	1982-07-01
NO814182L (no)	1982-06-23
SU1151204A3 (ru)	1985-04-15
ES518138A0 (es)	1983-10-16
JPS57128677A (en)	1982-08-10
PL234312A1 (en)	1983-02-14
PT74185A (de)	1982-01-01
PL238538A1 (en)	1983-04-25
RO84277B (ro)	1984-07-30
PL136127B1 (en)	1986-01-31
IE51985B1 (en)	1987-05-13
ES518139A0 (es)	1983-10-01
KR880002233B1 (ko)	1988-10-20
ZA818806B (en)	1982-11-24
CA1173033A (fr)	1984-08-21
ES8400096A1 (es)	1983-10-16
PT74185B (de)	1987-03-24
IL64605A (en)	1985-11-29
PL238537A1 (en)	1983-06-20
AU544386B2 (en)	1985-05-23
GR81382B (fr)	1984-12-11
RO84277A (fr)	1984-05-23
FI73418C (fi)	1987-10-09
SU1170970A3 (ru)	1985-07-30
ES508274A0 (es)	1983-03-16
US4532239A (en)	1985-07-30
DE3165595D1 (en)	1984-09-20
SG7585G (en)	1985-08-08
IL64605A0 (en)	1982-03-31
RO88190A (fr)	1985-12-30
IE813014L (en)	1982-06-22
CS236665B2 (en)	1985-05-15
PL137150B1 (en)	1986-05-31
ATE8991T1 (de)	1984-09-15
RO88201B (ro)	1985-12-31
ES8308859A1 (es)	1983-10-01
FI73418B (fi)	1987-06-30
RO88201A (fr)	1985-12-30
ES8304941A1 (es)	1983-03-16
DK542881A (da)	1982-06-23
PL137106B1 (en)	1986-04-30
KR830007577A (ko)	1983-11-04
DK149810B (da)	1986-10-06
PH17529A (en)	1984-09-13
DK149810C (da)	1987-03-23
EP0054946B1 (fr)	1984-08-15

Publication	Publication Date	Title
EP0253327B1 (fr)	1992-05-06	Dérivés de la diphénylpropylamine, leur préparation et leur utilisation pharmaceutique
DE1957706B2 (de)	1977-11-03	Kernsubstituierte 3-phenoxy-l-phenoxyalkylamino-propan-2-ole und arzneimittel auf deren basis
DE2644833A1 (de)	1978-04-20	Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung
EP0014951A2 (fr)	1980-09-03	Dérivés hétérocycliques d'oxypropanolamine, procédé pour leur préparation et médicaments contenant ces composés
DE2639718C2 (de)	1987-03-05	1-[6,7-Dimethoxy-3,4-dihydro-2H-isochinolin-1-on-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-äthyl)-amino]-propan, dessen physiologisch verträgliche Säureadditionssalze und diese Verbindungen enthaltende Arzneimittel
EP0054946B1 (fr)	1984-08-15	Pyridazines substituées basiques, leur préparation et leur utilisation
AT403282B (de)	1997-12-29	3(2h)-pyridazinon-derivate und verfahren zu ihrer herstellung
DD201305A5 (de)	1983-07-13	Verfahren zur herstellung von in 7-stellung substituierten benzopyranen
DE3230209C2 (de)	1985-08-22	Carbostyrilderivate, Verfahren zu deren Herstellung und diese enthaltende kardiotonische Mittel
DE2830884C2 (fr)	1990-01-11
CH640227A5 (de)	1983-12-30	Aminoalkoxyphenyl-derivate.
EP0025864B1 (fr)	1983-05-18	Dérivés de la tétrahydroquinoléine, procédés pour leur préparation, leur utilisation et compositions pharmaceutiques les contenant
EP0018360A1 (fr)	1980-11-12	N-(5-méthoxybenzofuran-2-ylcarbonyl)-N'-benzylpipérazine et procédé pour sa préparation.
DE3688450T2 (de)	1993-09-09	3(2h)-pyridazinonderivate, verfahren und zwischenprodukte zu deren herstellung und diese und/oder andere 3(2h)-pyridazinonderivate enthaltende heilmittel.
EP0027928B1 (fr)	1983-03-09	Dérivés pipéridiniques d'esters de l'acide 4,5-dialkyle-3-hydroxy-pyrrol-2-carboxylique, leur préparation et compositions pharmaceutiques les contenant
DE2923817C2 (de)	1981-07-09	(3-Alkylamino-2-hydroxyproposy)-furan-2-carbonsäureanilide und deren physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen
DE2300018C2 (de)	1983-01-20	1-[N-Methyl-N-(&beta;-phenyläthyl)-3-aminopropyl]- benzimidazol-Abkömmlinge
EP0303920A1 (fr)	1989-02-22	Dérivés de benzofuranne et agents thérapeutiques les contenant
DD146749A3 (de)	1981-03-04	Verfahren zur herstellung von phenoxyalkanolamin-derivaten
EP0008108B1 (fr)	1982-05-05	Dérivés aminopropanolés de 2-(o-hydroxyphényl)-pyrroles, procédé de préparation et compositions pharmaceutiques les contenant
DE2825861A1 (de)	1979-01-04	Pyridazinylhydrazone, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben
DD157796A5 (de)	1982-12-08	Verfahren zur herstellung neuer derivate des 2-amino-aethanols
EP0078989B1 (fr)	1985-05-08	Pyridazinones imines et leurs sels d'addition acide physiologiquement tolérables, procédé pour leur préparation et agents thérapeutiques contenant ces composés
DD202548A5 (de)	1983-09-21	Verfahren zur herstellung von neuen heteroaryloxypropanolaminen
DE3404481A1 (de)	1984-08-09	Basische cycloalkanonoximaether, verfahren zur herstellung derselben und ihre verwendung