DD202013A5 - Verfahren zur herstellung basisch substituierter pyridazine - Google Patents
Verfahren zur herstellung basisch substituierter pyridazine Download PDFInfo
- Publication number
- DD202013A5 DD202013A5 DD81235901A DD23590181A DD202013A5 DD 202013 A5 DD202013 A5 DD 202013A5 DD 81235901 A DD81235901 A DD 81235901A DD 23590181 A DD23590181 A DD 23590181A DD 202013 A5 DD202013 A5 DD 202013A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydrogen
- atoms
- general formula
- formula
- compound
- Prior art date
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- 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
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- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- 239000000026 Pentaerythritol tetranitrate Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
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- 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
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- 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
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- 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
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- 239000004301 calcium benzoate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 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
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- 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
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- 239000002612 dispersion medium Substances 0.000 description 1
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- 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)
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 (cs) |
| EP (1) | EP0054946B1 (cs) |
| JP (1) | JPS57128677A (cs) |
| KR (1) | KR880002233B1 (cs) |
| AT (1) | ATE8991T1 (cs) |
| AU (1) | AU544386B2 (cs) |
| CA (1) | CA1173033A (cs) |
| CS (1) | CS236665B2 (cs) |
| DD (1) | DD202013A5 (cs) |
| DE (2) | DE3048487A1 (cs) |
| DK (1) | DK149810C (cs) |
| ES (3) | ES8304941A1 (cs) |
| FI (1) | FI73418C (cs) |
| GR (1) | GR81382B (cs) |
| HK (1) | HK51485A (cs) |
| IE (1) | IE51985B1 (cs) |
| IL (1) | IL64605A (cs) |
| NO (1) | NO814182L (cs) |
| NZ (1) | NZ198919A (cs) |
| PH (1) | PH17529A (cs) |
| PL (3) | PL136127B1 (cs) |
| PT (1) | PT74185B (cs) |
| RO (3) | RO88201B (cs) |
| SG (1) | SG7585G (cs) |
| SU (2) | SU1170970A3 (cs) |
| ZA (1) | ZA818806B (cs) |
Families Citing this family (11)
| 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 (en) * | 1985-04-27 | 1991-09-18 | Nissan Chemical Industries Ltd. | 3(2h)pyridazinone, process for its preparation and anti-allergic agent containing it |
| 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 |
| US5221674A (en) * | 1989-06-19 | 1993-06-22 | Teikoku Hormone Mfg. Co., Ltd. | Pyridazinone derivatives |
| NZ234087A (en) * | 1989-06-19 | 1991-08-27 | Teikoku Hormone Mfg Co Ltd | 2-(3-aryloxy(2-hydroxy-propylamino))-2-methylpropyl- aminophenyl pyridazine derivatives |
| HU214320B (hu) * | 1991-12-20 | 1998-03-02 | EGIS Gyógyszergyár Rt. | Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására |
| CA2334220A1 (en) | 1998-06-05 | 1999-12-16 | Egis Gyogyszergyar Rt. | Process for the preparation of a 3(2h)-pyridazinone- 4-substituted amino- 5-chloro- derivative |
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741762A (cs) * | 1968-11-18 | 1970-05-19 | ||
| 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 |
| CH591448A5 (cs) * | 1974-05-14 | 1977-09-15 | Ciba Geigy Ag | |
| LU77339A1 (cs) * | 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/en not_active Expired
- 1981-12-08 DK DK542881A patent/DK149810C/da not_active IP Right Cessation
- 1981-12-08 FI FI813941A patent/FI73418C/fi not_active IP Right Cessation
- 1981-12-08 NO NO814182A patent/NO814182L/no unknown
- 1981-12-17 DD DD81235901A patent/DD202013A5/de unknown
- 1981-12-17 CS CS819455A patent/CS236665B2/cs unknown
- 1981-12-18 PL PL1981234312A patent/PL136127B1/pl unknown
- 1981-12-18 PL PL1981238537A patent/PL137150B1/pl unknown
- 1981-12-18 PL PL1981238538A patent/PL137106B1/pl unknown
- 1981-12-19 EP EP81110620A patent/EP0054946B1/de 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 RO113112A patent/RO88201B/ro unknown
- 1981-12-21 PH PH26659A patent/PH17529A/en unknown
- 1981-12-21 KR KR1019810005043A patent/KR880002233B1/ko not_active Expired
- 1981-12-21 RO RO113111A patent/RO88190B/ro unknown
- 1981-12-21 RO RO106060A patent/RO84277B/ro unknown
- 1981-12-21 SU SU813367148A patent/SU1170970A3/ru active
- 1981-12-21 ZA ZA818806A patent/ZA818806B/xx unknown
- 1981-12-21 JP JP56205363A patent/JPS57128677A/ja active Pending
- 1981-12-21 AU AU78704/81A patent/AU544386B2/en not_active Ceased
- 1981-12-21 GR GR66860A patent/GR81382B/el unknown
- 1981-12-21 IL IL64605A patent/IL64605A/xx unknown
- 1981-12-22 ES ES508274A patent/ES8304941A1/es not_active Expired
- 1981-12-22 PT PT74185A patent/PT74185B/pt unknown
-
1982
- 1982-08-20 SU SU823478901A patent/SU1151204A3/ru active
- 1982-12-13 ES ES518139A patent/ES8308859A1/es not_active Expired
- 1982-12-13 ES ES518138A patent/ES8400096A1/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
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