DK141333B - Fremgangsmåde til fremstilling af tetrahydro-thieno(3,2-c)- eller-(2,3-c)pyridinderivater. - Google Patents
Fremgangsmåde til fremstilling af tetrahydro-thieno(3,2-c)- eller-(2,3-c)pyridinderivater. Download PDFInfo
- Publication number
- DK141333B DK141333B DK297876AA DK297876A DK141333B DK 141333 B DK141333 B DK 141333B DK 297876A A DK297876A A DK 297876AA DK 297876 A DK297876 A DK 297876A DK 141333 B DK141333 B DK 141333B
- Authority
- DK
- Denmark
- Prior art keywords
- thieno
- tetrahydro
- pyridine
- formula
- hydroxy
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000013078 crystal Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- -1 6- (1-3-hydroxynaphthylmethyl) -4,5,6,7-tetrahydro-thieno- [2,3-c] pyridine Chemical compound 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- OJYDKYKQCVPTFG-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-c]pyridine Chemical class C1N=CC=C2SCCC21 OJYDKYKQCVPTFG-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- DKASUYIOUPPQSY-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[2,3-c]pyridine Chemical class C1C=NC=C2SCCC21 DKASUYIOUPPQSY-UHFFFAOYSA-N 0.000 claims 2
- FKQKBMPNBGMDEB-UHFFFAOYSA-N 2,6-dichloro-4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1CN1CC(C=CS2)=C2CC1 FKQKBMPNBGMDEB-UHFFFAOYSA-N 0.000 claims 1
- DDPDEZZCLVJUFJ-UHFFFAOYSA-N 2-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(CN2CC=3SC=CC=3CC2)=C1 DDPDEZZCLVJUFJ-UHFFFAOYSA-N 0.000 claims 1
- PHGWNHGNBZRXEA-UHFFFAOYSA-N 2-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-5-(dimethylamino)phenol Chemical compound OC1=CC(N(C)C)=CC=C1CN1CC(SC=C2)=C2CC1 PHGWNHGNBZRXEA-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920006324 polyoxymethylene Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical class C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-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
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 1
- SZTBVHSMGGKHIV-UHFFFAOYSA-N 2,3-dichloro-6-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)phenol Chemical compound C1=CC(Cl)=C(Cl)C(O)=C1CN1CC(SC=C2)=C2CC1 SZTBVHSMGGKHIV-UHFFFAOYSA-N 0.000 description 1
- OVBJBXNYOLGAHO-UHFFFAOYSA-N 2-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1CN1CC(SC=C2)=C2CC1 OVBJBXNYOLGAHO-UHFFFAOYSA-N 0.000 description 1
- XSXSHIKPBUVUIC-UHFFFAOYSA-N 2-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-6-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(CN2CC=3SC=CC=3CC2)=C1O XSXSHIKPBUVUIC-UHFFFAOYSA-N 0.000 description 1
- ARFZLYSRMCMIMR-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1CN1CC(C=CS2)=C2CC1 ARFZLYSRMCMIMR-UHFFFAOYSA-N 0.000 description 1
- NWVVVCUDMGQYTL-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-4-methoxyphenol Chemical compound COC1=CC=C(O)C(CN2CC=3C=CSC=3CC2)=C1 NWVVVCUDMGQYTL-UHFFFAOYSA-N 0.000 description 1
- SVYMFEPXGHGQNG-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1CN1CC(C=CS2)=C2CC1 SVYMFEPXGHGQNG-UHFFFAOYSA-N 0.000 description 1
- OCUQAUOYZMJSPM-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-6-methoxyphenol Chemical compound COC1=CC=CC(CN2CC=3C=CSC=3CC2)=C1O OCUQAUOYZMJSPM-UHFFFAOYSA-N 0.000 description 1
- LQKVSAZRTFKJBF-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-6-methylphenol Chemical compound CC1=CC=CC(CN2CC=3C=CSC=3CC2)=C1O LQKVSAZRTFKJBF-UHFFFAOYSA-N 0.000 description 1
- UVMIHYGDCXLPJP-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)phenol Chemical compound OC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 UVMIHYGDCXLPJP-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- DYSXAORFFOLJPL-UHFFFAOYSA-N 3-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1CN1CC(SC=C2)=C2CC1 DYSXAORFFOLJPL-UHFFFAOYSA-N 0.000 description 1
- HXNOEHIMWZDRTK-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C1NCCC2=C1SC=C2 HXNOEHIMWZDRTK-UHFFFAOYSA-N 0.000 description 1
- XBUVWBZNDZGRPM-UHFFFAOYSA-N 4-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CN2CC=3SC=CC=3CC2)=C1 XBUVWBZNDZGRPM-UHFFFAOYSA-N 0.000 description 1
- LTNBWFNJYMQXGS-UHFFFAOYSA-N 4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CN2CC=3C=CSC=3CC2)=C1 LTNBWFNJYMQXGS-UHFFFAOYSA-N 0.000 description 1
- UAKQHKZGKWIGLO-UHFFFAOYSA-N 4-chloro-2-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-ylmethyl)phenol Chemical compound OC1=CC=C(Cl)C=C1CN1CC(SC=C2)=C2CC1 UAKQHKZGKWIGLO-UHFFFAOYSA-N 0.000 description 1
- DQTUGTIPLDAVEM-UHFFFAOYSA-N 4-chloro-2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)phenol Chemical compound OC1=CC=C(Cl)C=C1CN1CC(C=CS2)=C2CC1 DQTUGTIPLDAVEM-UHFFFAOYSA-N 0.000 description 1
- MFSORRKKXZZSPE-UHFFFAOYSA-N 4-chloro-2-[(7-methyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)methyl]phenol Chemical compound C1CC=2C=CSC=2C(C)N1CC1=CC(Cl)=CC=C1O MFSORRKKXZZSPE-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010015856 Extrasystoles Diseases 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7521549A FR2317303A1 (fr) | 1975-07-09 | 1975-07-09 | Procede de preparation de derives de la tetrahydrothieno (3,2-c) et (2,3-c) pyridine |
| FR7521549 | 1975-07-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK297876A DK297876A (enrdf_load_stackoverflow) | 1977-01-10 |
| DK141333B true DK141333B (da) | 1980-02-25 |
| DK141333C DK141333C (enrdf_load_stackoverflow) | 1980-08-25 |
Family
ID=9157715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK297876AA DK141333B (da) | 1975-07-09 | 1976-07-01 | Fremgangsmåde til fremstilling af tetrahydro-thieno(3,2-c)- eller-(2,3-c)pyridinderivater. |
Country Status (26)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5665315A (en) * | 1979-11-02 | 1981-06-03 | Nec Corp | Magnetic recording and inspecting system |
| DE3736664A1 (de) * | 1987-10-29 | 1989-05-11 | Boehringer Ingelheim Kg | Tetrahydro-furo- und -thieno(2,3-c)pyridine, ihre verwendung als arzneimittel und verfahren zu ihrer herstellung |
| NZ233654A (en) * | 1989-05-18 | 1993-02-25 | Bristol Myers Squibb Co | 2-aminomethyl-5-aminophenol derivatives; hair dye compositions containing them |
-
1975
- 1975-07-09 FR FR7521549A patent/FR2317303A1/fr active Granted
-
1976
- 1976-03-31 LU LU74674A patent/LU74674A1/xx unknown
- 1976-04-01 CH CH404576A patent/CH609349A5/xx not_active IP Right Cessation
- 1976-04-21 GR GR50593A patent/GR59812B/el unknown
- 1976-04-23 YU YU1030/76A patent/YU40137B/xx unknown
- 1976-05-06 PT PT65072A patent/PT65072B/pt unknown
- 1976-05-19 NL NL7605362A patent/NL7605362A/xx not_active Application Discontinuation
- 1976-05-21 IE IE1079/76A patent/IE42821B1/en unknown
- 1976-05-24 IL IL49641A patent/IL49641A/xx unknown
- 1976-05-31 ES ES448404A patent/ES448404A1/es not_active Expired
- 1976-06-01 ZA ZA763219A patent/ZA763219B/xx unknown
- 1976-06-03 AR AR263501A patent/AR211019A1/es active
- 1976-06-09 SU SU762366005A patent/SU628819A3/ru active
- 1976-06-10 CA CA254,573A patent/CA1071634A/en not_active Expired
- 1976-06-16 MX MX000320U patent/MX3224E/es unknown
- 1976-07-01 DK DK297876AA patent/DK141333B/da not_active IP Right Cessation
- 1976-07-01 PH PH7618641A patent/PH12311A/en unknown
- 1976-07-05 AT AT489876A patent/AT348526B/de not_active IP Right Cessation
- 1976-07-06 BE BE168664A patent/BE843822A/xx not_active IP Right Cessation
- 1976-07-07 DE DE19762630474 patent/DE2630474A1/de active Pending
- 1976-07-07 DD DD193745A patent/DD125081A5/xx unknown
- 1976-07-07 SE SE7607762A patent/SE421699B/xx not_active IP Right Cessation
- 1976-07-08 PL PL1976191016A patent/PL100685B1/pl unknown
- 1976-07-08 JP JP51081441A patent/JPS5236691A/ja active Granted
- 1976-07-08 GB GB28511/76A patent/GB1544093A/en not_active Expired
- 1976-07-09 HU HU76PA00001255A patent/HU172280B/hu unknown
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