SU607550A3 - Способ получени производных простагландина - Google Patents
Способ получени производных простагландинаInfo
- Publication number
- SU607550A3 SU607550A3 SU762311606A SU2311606A SU607550A3 SU 607550 A3 SU607550 A3 SU 607550A3 SU 762311606 A SU762311606 A SU 762311606A SU 2311606 A SU2311606 A SU 2311606A SU 607550 A3 SU607550 A3 SU 607550A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- mixture
- observed
- acid
- following
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
- 239000012279 sodium borohydride Substances 0.000 claims description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 description 53
- 239000000047 product Substances 0.000 description 47
- 239000000203 mixture Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
- 238000010521 absorption reaction Methods 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 150000004702 methyl esters Chemical class 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 239000003921 oil Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000002329 infrared spectrum Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- -1 4-phenylbenzoyloxy Chemical group 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 5
- 238000012746 preparative thin layer chromatography Methods 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- PAEUNQGMXOCJBQ-UHFFFAOYSA-N (2-oxo-3-phenoxyheptyl)phosphonic acid Chemical compound O(C1=CC=CC=C1)C(C(CP(O)(O)=O)=O)CCCC PAEUNQGMXOCJBQ-UHFFFAOYSA-N 0.000 description 1
- URDOZEQDWGVQJP-UHFFFAOYSA-N (3-methoxy-3-methyl-2-oxoheptyl)phosphonic acid Chemical compound CCCCC(C)(OC)C(=O)CP(O)(O)=O URDOZEQDWGVQJP-UHFFFAOYSA-N 0.000 description 1
- NDFKTBCGKNOHPJ-AATRIKPKSA-N (E)-hept-2-enal Chemical compound CCCC\C=C\C=O NDFKTBCGKNOHPJ-AATRIKPKSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- 102100026882 Alpha-synuclein Human genes 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 241001553178 Arachis glabrata Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 239000012027 Collins reagent Substances 0.000 description 1
- 241000006479 Cyme Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 101000834898 Homo sapiens Alpha-synuclein Proteins 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 208000037062 Polyps Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NDFKTBCGKNOHPJ-UHFFFAOYSA-N hept-2-enal Chemical compound CCCCC=CC=O NDFKTBCGKNOHPJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3248/75A GB1538871A (en) | 1975-01-24 | 1975-01-24 | Prostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU607550A3 true SU607550A3 (ru) | 1978-05-15 |
Family
ID=9754749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762311606A SU607550A3 (ru) | 1975-01-24 | 1976-01-23 | Способ получени производных простагландина |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6024098B2 (fi) |
| AR (1) | AR212328A1 (fi) |
| AT (1) | AT351186B (fi) |
| BE (1) | BE837865A (fi) |
| CA (1) | CA1076569A (fi) |
| CH (1) | CH609682A5 (fi) |
| CS (1) | CS187333B2 (fi) |
| DD (1) | DD122517A5 (fi) |
| DE (1) | DE2601646A1 (fi) |
| DK (1) | DK27376A (fi) |
| FI (1) | FI64578C (fi) |
| FR (1) | FR2298322A1 (fi) |
| GB (1) | GB1538871A (fi) |
| GR (1) | GR58537B (fi) |
| HU (1) | HU174185B (fi) |
| IE (1) | IE43821B1 (fi) |
| IL (1) | IL48870A (fi) |
| LU (1) | LU74240A1 (fi) |
| NL (1) | NL185203C (fi) |
| NO (1) | NO147714C (fi) |
| NZ (1) | NZ179816A (fi) |
| PH (1) | PH14040A (fi) |
| PT (1) | PT64737B (fi) |
| RO (1) | RO71901A (fi) |
| SE (1) | SE446726B (fi) |
| SU (1) | SU607550A3 (fi) |
| YU (1) | YU40805B (fi) |
| ZA (1) | ZA7681B (fi) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4064350A (en) * | 1976-11-22 | 1977-12-20 | G. D. Searle & Co. | 15,16-Dihydroxyprostaglandins |
| US4194055A (en) * | 1976-03-03 | 1980-03-18 | American Cyanamid Company | 15,16-dioxy prostenoic acids and esters |
| IT1162731B (it) * | 1979-04-10 | 1987-04-01 | Lepetit Spa | 16-metil-16-metossi-5,6-diidro-prosta-glandine della serie e1 ad attivita'antisecretoria |
| JPS56162014A (en) * | 1980-05-16 | 1981-12-12 | Nippon Denso Co Ltd | Measuring device for flow rate of gas |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1392716A (en) * | 1971-05-11 | 1975-04-30 | Ici Ltd | Moulding |
| US4304907A (en) * | 1972-05-10 | 1981-12-08 | The Upjohn Company | Bicyclo lactone intermediates for prostaglandin analogs |
-
1975
- 1975-01-24 GB GB3248/75A patent/GB1538871A/en not_active Expired
-
1976
- 1976-01-05 FI FI760002A patent/FI64578C/fi not_active IP Right Cessation
- 1976-01-07 ZA ZA00760081A patent/ZA7681B/xx unknown
- 1976-01-09 GR GR49742A patent/GR58537B/el unknown
- 1976-01-15 YU YU111/76A patent/YU40805B/xx unknown
- 1976-01-16 CS CS76305A patent/CS187333B2/cs unknown
- 1976-01-17 DE DE19762601646 patent/DE2601646A1/de active Granted
- 1976-01-19 IL IL48870A patent/IL48870A/xx unknown
- 1976-01-21 AT AT36776A patent/AT351186B/de not_active IP Right Cessation
- 1976-01-21 RO RO7684563A patent/RO71901A/ro unknown
- 1976-01-22 DD DD190915A patent/DD122517A5/xx unknown
- 1976-01-22 PH PH18006A patent/PH14040A/en unknown
- 1976-01-22 IE IE120/76A patent/IE43821B1/en unknown
- 1976-01-22 FR FR7601707A patent/FR2298322A1/fr active Granted
- 1976-01-23 SU SU762311606A patent/SU607550A3/ru active
- 1976-01-23 NO NO760214A patent/NO147714C/no unknown
- 1976-01-23 CA CA244,132A patent/CA1076569A/en not_active Expired
- 1976-01-23 LU LU74240A patent/LU74240A1/xx unknown
- 1976-01-23 CH CH83176A patent/CH609682A5/xx not_active IP Right Cessation
- 1976-01-23 NZ NZ179816A patent/NZ179816A/xx unknown
- 1976-01-23 HU HU76LE788A patent/HU174185B/hu not_active IP Right Cessation
- 1976-01-23 JP JP51006567A patent/JPS6024098B2/ja not_active Expired
- 1976-01-23 AR AR262009A patent/AR212328A1/es active
- 1976-01-23 DK DK27376*#A patent/DK27376A/da not_active Application Discontinuation
- 1976-01-23 SE SE7600729A patent/SE446726B/xx not_active IP Right Cessation
- 1976-01-23 NL NLAANVRAGE7600696,A patent/NL185203C/xx not_active IP Right Cessation
- 1976-01-23 BE BE163765A patent/BE837865A/xx not_active IP Right Cessation
- 1976-01-23 PT PT64737A patent/PT64737B/pt unknown
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