CA1082201A - Indazolyl-(4)-oxypropanolamines and the preparation thereof - Google Patents
Indazolyl-(4)-oxypropanolamines and the preparation thereofInfo
- Publication number
- CA1082201A CA1082201A CA277,405A CA277405A CA1082201A CA 1082201 A CA1082201 A CA 1082201A CA 277405 A CA277405 A CA 277405A CA 1082201 A CA1082201 A CA 1082201A
- Authority
- CA
- Canada
- Prior art keywords
- indazolyl
- methyl
- oxy
- group
- process according
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 alkyl radical Chemical class 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 230000001681 protective effect Effects 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 11
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- QCUPEVKVINNRGY-UHFFFAOYSA-N 6-methyl-4-(oxiran-2-ylmethoxy)-1h-indazole Chemical compound C=12C=NNC2=CC(C)=CC=1OCC1CO1 QCUPEVKVINNRGY-UHFFFAOYSA-N 0.000 claims description 5
- YILIWPRHODZCMA-UHFFFAOYSA-N 1-[4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound C1=CC=C2N(C(=O)C)N=CC2=C1OCC1CO1 YILIWPRHODZCMA-UHFFFAOYSA-N 0.000 claims description 4
- GTVBWMSRYWPEKN-UHFFFAOYSA-N 1-[6-methyl-4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound C1=C(C)C=C2N(C(=O)C)N=CC2=C1OCC1CO1 GTVBWMSRYWPEKN-UHFFFAOYSA-N 0.000 claims description 4
- MPFDHICUUKUXLG-UHFFFAOYSA-N 1H-indazol-4-ol Chemical compound OC1=CC=CC2=C1C=NN2 MPFDHICUUKUXLG-UHFFFAOYSA-N 0.000 claims description 4
- URDSHYOWFGTOCY-UHFFFAOYSA-N n-methylsulfanylpropan-2-amine Chemical compound CSNC(C)C URDSHYOWFGTOCY-UHFFFAOYSA-N 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- IVKZYPSZIUYYPC-UHFFFAOYSA-N 1-chloro-3-[(6-methyl-1h-indazol-4-yl)oxy]propan-2-ol Chemical compound CC1=CC(OCC(O)CCl)=C2C=NNC2=C1 IVKZYPSZIUYYPC-UHFFFAOYSA-N 0.000 claims description 3
- GGHVECOXMJTFAC-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indazole Chemical compound C=1C=CC=2NN=CC=2C=1OCC1CO1 GGHVECOXMJTFAC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- 150000007524 organic acids Chemical class 0.000 claims description 3
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- QOBAXXQQFJJPAA-UHFFFAOYSA-N 1-(butylamino)propan-2-ol Chemical compound CCCCNCC(C)O QOBAXXQQFJJPAA-UHFFFAOYSA-N 0.000 claims description 2
- FPAAJJSECSZIAD-UHFFFAOYSA-N 1-[7-methyl-4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound C1=CC(C)=C2N(C(=O)C)N=CC2=C1OCC1CO1 FPAAJJSECSZIAD-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
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- 239000001301 oxygen Substances 0.000 claims description 2
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- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 4
- IDVYDIGMVKRDGK-UHFFFAOYSA-N 1-[5-methyl-4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound CC1=CC=C2N(C(=O)C)N=CC2=C1OCC1CO1 IDVYDIGMVKRDGK-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- FETIXXANSNSUPJ-UHFFFAOYSA-N 1-[5-ethyl-4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound CCC1=CC=C2N(C(C)=O)N=CC2=C1OCC1CO1 FETIXXANSNSUPJ-UHFFFAOYSA-N 0.000 claims 1
- NMCDWHSFYFNCJO-UHFFFAOYSA-N 1-[6-ethyl-4-(oxiran-2-ylmethoxy)indazol-1-yl]ethanone Chemical compound C=12C=NN(C(C)=O)C2=CC(CC)=CC=1OCC1CO1 NMCDWHSFYFNCJO-UHFFFAOYSA-N 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 7
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- GRSTVVGJSKHCCS-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanone Chemical compound N=1C=CNC=1C(=O)C1=NC=CN1 GRSTVVGJSKHCCS-UHFFFAOYSA-N 0.000 description 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NOQXXYIGRPAZJC-UHFFFAOYSA-N oxiran-2-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC1 NOQXXYIGRPAZJC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2619164.0 | 1976-04-30 | ||
| DE2619164A DE2619164C2 (de) | 1976-04-30 | 1976-04-30 | Indazolyl-(4)-oxy-propanolamine, Verfahren zu ihrer Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082201A true CA1082201A (en) | 1980-07-22 |
Family
ID=5976768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,405A Expired CA1082201A (en) | 1976-04-30 | 1977-04-29 | Indazolyl-(4)-oxypropanolamines and the preparation thereof |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4143149A (en, 2012) |
| JP (1) | JPS52133982A (en, 2012) |
| AR (1) | AR213114A1 (en, 2012) |
| AT (1) | AT350560B (en, 2012) |
| AU (1) | AU508791B2 (en, 2012) |
| BE (1) | BE853949A (en, 2012) |
| CA (1) | CA1082201A (en, 2012) |
| CH (1) | CH626351A5 (en, 2012) |
| CS (1) | CS195332B2 (en, 2012) |
| DD (1) | DD129443A5 (en, 2012) |
| DE (1) | DE2619164C2 (en, 2012) |
| DK (1) | DK137956C (en, 2012) |
| ES (1) | ES458176A1 (en, 2012) |
| FI (1) | FI771308A7 (en, 2012) |
| FR (1) | FR2349576A1 (en, 2012) |
| GB (1) | GB1518630A (en, 2012) |
| HU (1) | HU174675B (en, 2012) |
| IE (1) | IE44742B1 (en, 2012) |
| LU (1) | LU77227A1 (en, 2012) |
| NL (1) | NL7704530A (en, 2012) |
| PL (1) | PL103682B1 (en, 2012) |
| SE (1) | SE7704829L (en, 2012) |
| SU (1) | SU679138A3 (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314943A (en) * | 1977-07-13 | 1982-02-09 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| US4495352A (en) * | 1979-02-13 | 1985-01-22 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| DE2905877A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CA1156661A (en) * | 1980-02-25 | 1983-11-08 | Hoffmann-La Roche Limited | Phenoxy-aminopropanol derivatives |
| DE3023369A1 (de) | 1980-06-23 | 1982-01-14 | Boehringer Mannheim Gmbh, 6800 Mannheim | Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3131146A1 (de) * | 1981-08-06 | 1983-02-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue heteroaryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JP2001163854A (ja) * | 1999-09-28 | 2001-06-19 | Nippon Nohyaku Co Ltd | チオアルキルアミン誘導体及びその製造方法 |
| JP2002105046A (ja) * | 2000-09-25 | 2002-04-10 | Nippon Nohyaku Co Ltd | チオアルキルアミン−ｓ−酸化体及びその塩類 |
| WO2002100833A1 (fr) * | 2001-06-12 | 2002-12-19 | Sumitomo Pharmaceuticals Company, Limited | Inhibiteurs de rho kinase |
| US11173144B2 (en) * | 2016-05-13 | 2021-11-16 | The Board Of Trustees Of The Leland Stanford Junior University | Adrenergic receptor modulating compounds and methods of using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843678A (en) * | 1971-03-15 | 1974-10-22 | Tenneco Chem | Process for the production of substituted indazoles |
| CA1001161A (en) * | 1972-05-05 | 1976-12-07 | Burton K. Wasson | 5-(3-substituted amino-2-hydroxypropoxy)1,3-disubstituted pyrazoles and method of preparation |
| GB1435943A (en) * | 1973-02-07 | 1976-05-19 | Delmar Chem | Indazole-derived tertiary amines |
-
1976
- 1976-04-30 DE DE2619164A patent/DE2619164C2/de not_active Expired
-
1977
- 1977-04-16 ES ES458176A patent/ES458176A1/es not_active Expired
- 1977-04-25 SU SU772473627A patent/SU679138A3/ru active
- 1977-04-25 FI FI771308A patent/FI771308A7/fi not_active Application Discontinuation
- 1977-04-25 US US05/790,648 patent/US4143149A/en not_active Expired - Lifetime
- 1977-04-25 AR AR267336A patent/AR213114A1/es active
- 1977-04-25 DD DD7700198591A patent/DD129443A5/xx unknown
- 1977-04-26 JP JP4835077A patent/JPS52133982A/ja active Pending
- 1977-04-26 BE BE177010A patent/BE853949A/xx unknown
- 1977-04-26 AU AU24593/77A patent/AU508791B2/en not_active Expired
- 1977-04-26 NL NL7704530A patent/NL7704530A/xx not_active Application Discontinuation
- 1977-04-27 SE SE7704829A patent/SE7704829L/ unknown
- 1977-04-27 CH CH524177A patent/CH626351A5/de not_active IP Right Cessation
- 1977-04-27 DK DK184377A patent/DK137956C/da active
- 1977-04-28 IE IE854/77A patent/IE44742B1/en unknown
- 1977-04-28 FR FR7712887A patent/FR2349576A1/fr active Granted
- 1977-04-28 LU LU77227A patent/LU77227A1/xx unknown
- 1977-04-28 AT AT303477A patent/AT350560B/de not_active IP Right Cessation
- 1977-04-28 PL PL1977197704A patent/PL103682B1/pl unknown
- 1977-04-29 CA CA277,405A patent/CA1082201A/en not_active Expired
- 1977-04-29 GB GB17995/77A patent/GB1518630A/en not_active Expired
- 1977-04-29 CS CS772839A patent/CS195332B2/cs unknown
- 1977-04-29 HU HU77BO1664A patent/HU174675B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2349576A1 (fr) | 1977-11-25 |
| DK184377A (da) | 1977-10-31 |
| FI771308A7 (en, 2012) | 1977-10-31 |
| DK137956C (da) | 1978-11-06 |
| AU508791B2 (en) | 1980-04-03 |
| US4143149A (en) | 1979-03-06 |
| DE2619164A1 (de) | 1977-11-17 |
| ES458176A1 (es) | 1978-04-01 |
| IE44742B1 (en) | 1982-03-10 |
| DE2619164C2 (de) | 1985-07-11 |
| AT350560B (de) | 1979-06-11 |
| PL197704A1 (pl) | 1978-04-24 |
| ATA303477A (de) | 1978-11-15 |
| IE44742L (en) | 1977-10-30 |
| GB1518630A (en) | 1978-07-19 |
| DD129443A5 (de) | 1978-01-18 |
| NL7704530A (nl) | 1977-11-01 |
| CS195332B2 (en) | 1980-01-31 |
| FR2349576B1 (en, 2012) | 1980-03-21 |
| CH626351A5 (en, 2012) | 1981-11-13 |
| SU679138A3 (ru) | 1979-08-05 |
| AR213114A1 (es) | 1978-12-15 |
| BE853949A (fr) | 1977-10-26 |
| LU77227A1 (en, 2012) | 1978-06-01 |
| SE7704829L (sv) | 1977-10-31 |
| DK137956B (da) | 1978-06-12 |
| JPS52133982A (en) | 1977-11-09 |
| PL103682B1 (pl) | 1979-07-31 |
| HU174675B (hu) | 1980-03-28 |
| AU2459377A (en) | 1978-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |