NO132835B - - Google Patents
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- Publication number
- NO132835B NO132835B NO3632/71A NO363271A NO132835B NO 132835 B NO132835 B NO 132835B NO 3632/71 A NO3632/71 A NO 3632/71A NO 363271 A NO363271 A NO 363271A NO 132835 B NO132835 B NO 132835B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- meaning
- compound
- group
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- -1 cyano, ethynyl Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 3
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GPKDFTKUEQUSCC-UHFFFAOYSA-N Cl.C(#N)C1=C(OC(C(CC(CO)(C)C)O)N)C=CC=C1 Chemical compound Cl.C(#N)C1=C(OC(C(CC(CO)(C)C)O)N)C=CC=C1 GPKDFTKUEQUSCC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000007098 aminolysis reaction Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- OCDHRUIARWXIBR-UHFFFAOYSA-N 2-[(2-prop-2-ynoxyphenoxy)methyl]oxirane Chemical compound C#CCOC1=CC=CC=C1OCC1OC1 OCDHRUIARWXIBR-UHFFFAOYSA-N 0.000 description 2
- NYIAPPUULRVFQP-UHFFFAOYSA-N C(#N)C1=C(OC=CC)C=CC=C1 Chemical group C(#N)C1=C(OC=CC)C=CC=C1 NYIAPPUULRVFQP-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LTIZQAANULHFEW-UHFFFAOYSA-N 1-nitro-2-prop-1-enoxybenzene Chemical group CC=COC1=CC=CC=C1[N+]([O-])=O LTIZQAANULHFEW-UHFFFAOYSA-N 0.000 description 1
- BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 description 1
- QLWSYRNMJMYSBE-UHFFFAOYSA-N 2-[(2-ethynylphenoxy)methyl]oxirane Chemical compound C#CC1=CC=CC=C1OCC1OC1 QLWSYRNMJMYSBE-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- RVUYFVDARIQGFE-UHFFFAOYSA-N C(#C)C1=C(OC=CC)C=CC=C1 Chemical group C(#C)C1=C(OC=CC)C=CC=C1 RVUYFVDARIQGFE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LZMATGARSSLFMQ-UHFFFAOYSA-N N-isopropylurea Natural products CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MQAYFGXOFCEZRW-UHFFFAOYSA-N oxane-2-carboxylic acid Chemical compound OC(=O)C1CCCCO1 MQAYFGXOFCEZRW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702048838 DE2048838A1 (de) | 1970-10-05 | 1970-10-05 | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132835B true NO132835B (nl) | 1975-10-06 |
| NO132835C NO132835C (nl) | 1976-01-14 |
Family
ID=5784228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3632/71A NO132835C (nl) | 1970-10-05 | 1971-10-04 |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5710097B1 (nl) |
| AT (10) | AT318564B (nl) |
| AU (1) | AU469119B2 (nl) |
| BE (1) | BE773472A (nl) |
| BG (8) | BG20100A3 (nl) |
| CA (1) | CA1008866A (nl) |
| CH (11) | CH583685A5 (nl) |
| CS (2) | CS172932B2 (nl) |
| DE (1) | DE2048838A1 (nl) |
| DK (1) | DK130958B (nl) |
| ES (8) | ES395671A1 (nl) |
| FI (1) | FI55491C (nl) |
| FR (1) | FR2110230B1 (nl) |
| GB (1) | GB1364280A (nl) |
| HU (1) | HU163226B (nl) |
| IE (1) | IE35693B1 (nl) |
| IL (1) | IL37830A (nl) |
| NL (1) | NL174249C (nl) |
| NO (1) | NO132835C (nl) |
| PH (1) | PH9959A (nl) |
| PL (10) | PL84225B1 (nl) |
| RO (8) | RO62357A (nl) |
| SE (1) | SE383631B (nl) |
| SU (2) | SU419024A3 (nl) |
| YU (2) | YU35576B (nl) |
| ZA (1) | ZA716643B (nl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055658A (en) * | 1976-05-17 | 1977-10-25 | Mead Johnson & Company | Cyanomethylphenethanolamines |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3248835A1 (de) * | 1981-06-23 | 1983-06-30 | American Hospital Supply Corp | Zusammensetzungen fuer die behandlung von glaukom |
| US4652584A (en) * | 1984-07-13 | 1987-03-24 | Mcneilab, Inc. | Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension |
| DE4422707A1 (de) * | 1994-06-29 | 1996-01-04 | Hoechst Ag | Verfahren zum Färben aminierter Cellulose-/Polyester-Mischgewebe mit faserreaktiven Dispersionsfarbstoffen |
| JP4934287B2 (ja) * | 2005-04-05 | 2012-05-16 | 花王株式会社 | 美白剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD45360A (nl) * | ||||
| CA945172A (en) * | 1969-02-21 | 1974-04-09 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
-
1970
- 1970-10-05 DE DE19702048838 patent/DE2048838A1/de not_active Withdrawn
-
1971
- 1971-04-10 SE SE7112536*A patent/SE383631B/xx unknown
- 1971-09-30 SU SU1700834A patent/SU419024A3/ru active
- 1971-10-01 CH CH423975A patent/CH583685A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424275A patent/CH583687A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH1430971A patent/CH564507A5/xx not_active IP Right Cessation
- 1971-10-01 IL IL37830A patent/IL37830A/xx unknown
- 1971-10-01 CH CH424675A patent/CH564516A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH423875A patent/CH587223A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424075A patent/CH583686A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424175A patent/CH584185A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424375A patent/CH563341A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424575A patent/CH563342A5/xx not_active IP Right Cessation
- 1971-10-04 PL PL1971174906A patent/PL84225B1/pl unknown
- 1971-10-04 JP JP7778571A patent/JPS5710097B1/ja active Pending
- 1971-10-04 BE BE773472A patent/BE773472A/xx not_active IP Right Cessation
- 1971-10-04 BG BG020287A patent/BG20100A3/xx unknown
- 1971-10-04 BG BG020288A patent/BG18858A3/xx unknown
- 1971-10-04 FI FI2769/71A patent/FI55491C/fi active
- 1971-10-04 PL PL1971174910A patent/PL84396B1/pl unknown
- 1971-10-04 BG BG020290A patent/BG19793A3/xx unknown
- 1971-10-04 PL PL1971174905A patent/PL84226B1/pl unknown
- 1971-10-04 PL PL1971174909A patent/PL84267B1/pl unknown
- 1971-10-04 BG BG020291A patent/BG18859A3/xx unknown
- 1971-10-04 BG BG20289A patent/BG19134A3/xx unknown
- 1971-10-04 BG BG020285A patent/BG19133A3/xx unknown
- 1971-10-04 GB GB4610371A patent/GB1364280A/en not_active Expired
- 1971-10-04 PL PL1971150902A patent/PL82037B1/pl unknown
- 1971-10-04 NO NO3632/71A patent/NO132835C/no unknown
- 1971-10-04 PL PL1971174907A patent/PL84224B1/pl unknown
- 1971-10-04 NL NLAANVRAGE7113581,A patent/NL174249C/nl not_active IP Right Cessation
- 1971-10-04 DK DK481671AA patent/DK130958B/da not_active IP Right Cessation
- 1971-10-04 CA CA124,290A patent/CA1008866A/en not_active Expired
- 1971-10-04 BG BG018670A patent/BG20338A3/xx unknown
- 1971-10-04 PL PL1971174908A patent/PL84223B1/pl unknown
- 1971-10-04 ZA ZA716643A patent/ZA716643B/xx unknown
- 1971-10-04 PH PH12895A patent/PH9959A/en unknown
- 1971-10-04 BG BG020286A patent/BG18857A3/xx unknown
- 1971-10-04 YU YU2505/71A patent/YU35576B/xx unknown
- 1971-10-04 PL PL1971174911A patent/PL84227B1/pl unknown
- 1971-10-04 PL PL1971174903A patent/PL84212B1/pl unknown
- 1971-10-04 PL PL1971174912A patent/PL84276B1/pl unknown
- 1971-10-04 ES ES395671A patent/ES395671A1/es not_active Expired
- 1971-10-05 RO RO7100073335A patent/RO62357A/ro unknown
- 1971-10-05 RO RO73336A patent/RO62313A/ro unknown
- 1971-10-05 AT AT734773A patent/AT318564B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073333A patent/RO62355A/ro unknown
- 1971-10-05 AT AT735573A patent/AT318572B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073339A patent/RO62359A/ro unknown
- 1971-10-05 IE IE1246/71A patent/IE35693B1/xx unknown
- 1971-10-05 AT AT735173A patent/AT318568B/de not_active IP Right Cessation
- 1971-10-05 AT AT735473A patent/AT318571B/de not_active IP Right Cessation
- 1971-10-05 FR FR7135823A patent/FR2110230B1/fr not_active Expired
- 1971-10-05 AT AT735373A patent/AT318570B/de not_active IP Right Cessation
- 1971-10-05 RO RO68372A patent/RO61540A/ro unknown
- 1971-10-05 AT AT734873A patent/AT318565B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073338A patent/RO62358A/ro unknown
- 1971-10-05 RO RO73334A patent/RO62356A/ro unknown
- 1971-10-05 AT AT735273A patent/AT318569B/de not_active IP Right Cessation
- 1971-10-05 HU HUBO1319A patent/HU163226B/hu unknown
- 1971-10-05 AT AT735073A patent/AT318567B/de not_active IP Right Cessation
- 1971-10-05 CS CS7034A patent/CS172932B2/cs unknown
- 1971-10-05 CS CS4618A patent/CS172950B2/cs unknown
- 1971-10-05 RO RO7100073337A patent/RO62267A/ro unknown
- 1971-10-05 AU AU34182/71A patent/AU469119B2/en not_active Expired
- 1971-10-05 AT AT734973A patent/AT318566B/de not_active IP Right Cessation
- 1971-10-05 AT AT859371A patent/AT318561B/de not_active IP Right Cessation
-
1972
- 1972-02-17 ES ES399873A patent/ES399873A1/es not_active Expired
- 1972-02-17 ES ES399874A patent/ES399874A1/es not_active Expired
- 1972-02-17 ES ES399872A patent/ES399872A1/es not_active Expired
- 1972-02-17 ES ES399869A patent/ES399869A1/es not_active Expired
- 1972-02-17 ES ES399868A patent/ES399868A1/es not_active Expired
- 1972-02-17 ES ES399870A patent/ES399870A1/es not_active Expired
- 1972-02-17 ES ES399871A patent/ES399871A1/es not_active Expired
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1973
- 1973-02-28 SU SU731888527A patent/SU677649A3/ru active
-
1975
- 1975-04-03 CH CH414475A patent/CH564515A5/xx not_active IP Right Cessation
-
1976
- 1976-12-06 CH CH1430971A patent/CH587227A5/xx not_active IP Right Cessation
-
1979
- 1979-02-02 YU YU236/79A patent/YU35577B/xx unknown
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