IL27933A - Pyrillary aminoalkyl ketones, their preparation and pharmaceutical preparations containing them - Google Patents
Pyrillary aminoalkyl ketones, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL27933A IL27933A IL27933A IL2793367A IL27933A IL 27933 A IL27933 A IL 27933A IL 27933 A IL27933 A IL 27933A IL 2793367 A IL2793367 A IL 2793367A IL 27933 A IL27933 A IL 27933A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- hydrogen
- hydrogen atom
- atom
- olaim
- Prior art date
Links
- -1 aminoalkyl ketones Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005283 haloketone group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 150000001350 alkyl halides Chemical class 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- XEKJUHXNZQPCHP-UHFFFAOYSA-N 1H-pyrrol-1-ium dichloride Chemical compound C1=C[NH2+]C=C1.C1=C[NH2+]C=C1.[Cl-].[Cl-] XEKJUHXNZQPCHP-UHFFFAOYSA-N 0.000 description 1
- IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21777/66A GB1154742A (en) | 1966-05-17 | 1966-05-17 | Pyrrylamino Ketones |
| GB53844/68A GB1154745A (en) | 1966-05-17 | 1966-05-17 | Haloketones |
| GB21778/66A GB1154743A (en) | 1966-05-17 | 1966-05-17 | Aminoethanols |
| GB21779/66A GB1154744A (en) | 1966-05-17 | 1966-05-17 | Disubstituted Aminoethanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27933A true IL27933A (en) | 1971-10-20 |
Family
ID=27448540
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27933A IL27933A (en) | 1966-05-17 | 1967-05-08 | Pyrillary aminoalkyl ketones, their preparation and pharmaceutical preparations containing them |
| IL27934A IL27934A (en) | 1966-05-17 | 1967-05-08 | 1-pyrryl-2-aminoethanols,their preparation and pharmaceutical compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27934A IL27934A (en) | 1966-05-17 | 1967-05-08 | 1-pyrryl-2-aminoethanols,their preparation and pharmaceutical compositions containing them |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US3558652A (en, 2012) |
| AT (1) | AT278770B (en, 2012) |
| BE (2) | BE698568A (en, 2012) |
| BR (1) | BR6789534D0 (en, 2012) |
| CH (2) | CH484108A (en, 2012) |
| CY (1) | CY634A (en, 2012) |
| DE (4) | DE1720018B2 (en, 2012) |
| DK (2) | DK133943B (en, 2012) |
| ES (1) | ES340591A1 (en, 2012) |
| FI (2) | FI48349C (en, 2012) |
| FR (3) | FR6769M (en, 2012) |
| GB (4) | GB1154743A (en, 2012) |
| IL (2) | IL27933A (en, 2012) |
| LU (1) | LU53619A1 (en, 2012) |
| NL (3) | NL141087B (en, 2012) |
| NO (2) | NO121950B (en, 2012) |
| SE (2) | SE313565B (en, 2012) |
| YU (2) | YU32531B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345872A (en) * | 1970-09-03 | 1974-02-06 | Wyeth John & Brother Ltd | Amino-and acylamino-pyridine and hydropyridine derivatives |
| JPS5549575B2 (en, 2012) * | 1971-10-30 | 1980-12-12 | ||
| BE790747A (fr) * | 1971-10-30 | 1973-02-15 | Whitefin Holding Sa | Stereo-isomeres du 1-(1'-(0-chloro-benzyl)-pyrrol-2'-yl) -2-dibutyl sec.-amino-ethanol et procede pour leur preparation |
| US3972925A (en) * | 1974-10-29 | 1976-08-03 | Eli Lilly And Company | N-perfluoroacyl-amino acids and derivatives thereof |
| US4029672A (en) * | 1976-02-26 | 1977-06-14 | American Hoechst Corporation | Aminoalkylpyrrolobenzoxazalkanes |
| DE2615117B2 (de) * | 1976-04-07 | 1978-07-20 | Siemens Ag, 1000 Berlin Und 8000 Muenchen | Mit einer Überspannungsschutzanordnung versehener konstantspannungsgeregelter bürstenloser Synchrongenerator |
| BE848465A (fr) | 1976-11-18 | 1977-03-16 | Stereo-isomeres de 1-(1'-benzyl-2' pyrryl)-2-disec.butylaminoethanols a activite analgesique et preparations pharmaceutiques qui les contiennent | |
| US4560770A (en) * | 1983-02-09 | 1985-12-24 | Ciba-Geigy Corporation | Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds |
| US4667039A (en) * | 1983-11-07 | 1987-05-19 | Hoechst-Roussel Pharmaceuticals Inc. | 11-substituted 5H,11H-pyrrolo(2,1-C) (1,4)benzoxazepines as antipsychotic and analgesic agents |
| US5360811A (en) * | 1990-03-13 | 1994-11-01 | Hoechst-Roussel Pharmaceuticals Incorporated | 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols and related compounds as anti-inflammatory agents |
| DE4020851A1 (de) * | 1990-06-29 | 1992-01-02 | Cassella Ag | 2-(aminoalkyl)-pyrrolaldehyde, verfahren zu ihrer herstellung und ihre verwendung |
| US20050142489A1 (en) * | 2002-03-19 | 2005-06-30 | Horst Berneth | Squarylium dyes as light-absorbing compound in the information layer of optical data carriers |
| GB0711776D0 (en) * | 2007-06-18 | 2007-07-25 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| JP7551087B2 (ja) * | 2018-06-27 | 2024-09-17 | キネタ， インコーポレイテッド | プロテアソーム活性増強化合物 |
| JP7561632B2 (ja) | 2018-06-27 | 2024-10-04 | キネタ， インコーポレイテッド | プロテアソーム活性増強化合物 |
-
1966
- 1966-05-17 GB GB21778/66A patent/GB1154743A/en not_active Expired
- 1966-05-17 GB GB53844/68A patent/GB1154745A/en not_active Expired
- 1966-05-17 GB GB21777/66A patent/GB1154742A/en not_active Expired
- 1966-05-17 GB GB21779/66A patent/GB1154744A/en not_active Expired
-
1967
- 1967-05-08 US US636625A patent/US3558652A/en not_active Expired - Lifetime
- 1967-05-08 IL IL27933A patent/IL27933A/en unknown
- 1967-05-08 IL IL27934A patent/IL27934A/xx unknown
- 1967-05-08 US US636649A patent/US3539589A/en not_active Expired - Lifetime
- 1967-05-08 LU LU53619D patent/LU53619A1/xx unknown
- 1967-05-11 DE DE19671720018 patent/DE1720018B2/de active Granted
- 1967-05-12 AT AT448267A patent/AT278770B/de not_active IP Right Cessation
- 1967-05-12 DE DE1720020A patent/DE1720020B2/de active Granted
- 1967-05-12 NO NO168123A patent/NO121950B/no unknown
- 1967-05-12 DE DE1795841A patent/DE1795841C3/de not_active Expired
- 1967-05-12 DE DE1720019A patent/DE1720019C3/de not_active Expired
- 1967-05-12 NO NO168124A patent/NO123034B/no unknown
- 1967-05-16 DK DK254767AA patent/DK133943B/da unknown
- 1967-05-16 DK DK254867A patent/DK132411C/da active
- 1967-05-16 YU YU0973/67A patent/YU32531B/xx unknown
- 1967-05-16 ES ES340591A patent/ES340591A1/es not_active Expired
- 1967-05-17 BR BR189534/67A patent/BR6789534D0/pt unknown
- 1967-05-17 NL NL676706839A patent/NL141087B/xx not_active IP Right Cessation
- 1967-05-17 BE BE698568D patent/BE698568A/xx unknown
- 1967-05-17 FR FR106669A patent/FR6769M/fr not_active Expired
- 1967-05-17 FR FR106670A patent/FR6770M/fr not_active Expired
- 1967-05-17 FI FI671408A patent/FI48349C/fi active
- 1967-05-17 FR FR106668A patent/FR6663M/fr not_active Expired
- 1967-05-17 SE SE6867/67A patent/SE313565B/xx unknown
- 1967-05-17 SE SE6866/67A patent/SE313564B/xx unknown
- 1967-05-17 CH CH694267A patent/CH484108A/de not_active IP Right Cessation
- 1967-05-17 NL NL6706840.A patent/NL156394B/xx not_active IP Right Cessation
- 1967-05-17 FI FI671407A patent/FI48348C/fi active
- 1967-05-17 CH CH694067A patent/CH484107A/de not_active IP Right Cessation
- 1967-05-17 NL NL676706841A patent/NL149375B/xx not_active IP Right Cessation
- 1967-05-17 BE BE698567D patent/BE698567A/xx unknown
-
1970
- 1970-10-05 US US78262A patent/US3706750A/en not_active Expired - Lifetime
-
1972
- 1972-02-23 CY CY63472A patent/CY634A/xx unknown
-
1973
- 1973-09-04 YU YU2345/73A patent/YU36700B/xx unknown
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