CH528531A - Verfahren zur Herstellung neuer heterocyclischer Verbindungen aromatischen Charakters - Google Patents
Verfahren zur Herstellung neuer heterocyclischer Verbindungen aromatischen CharaktersInfo
- Publication number
- CH528531A CH528531A CH1606467A CH1606467A CH528531A CH 528531 A CH528531 A CH 528531A CH 1606467 A CH1606467 A CH 1606467A CH 1606467 A CH1606467 A CH 1606467A CH 528531 A CH528531 A CH 528531A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- acid
- carboxyl group
- group
- compound
- Prior art date
Links
- 150000003557 thiazoles Chemical class 0.000 title abstract description 8
- 150000002916 oxazoles Chemical class 0.000 title abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 60
- -1 nitro- Chemical class 0.000 claims abstract description 51
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 150000001408 amides Chemical class 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 235000019260 propionic acid Nutrition 0.000 claims description 13
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000005283 haloketone group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 125000002560 nitrile group Chemical group 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000001391 thioamide group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 24
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 101150000679 OPTN gene Proteins 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 61
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 59
- 239000000243 solution Substances 0.000 description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 44
- 235000019441 ethanol Nutrition 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 229910000029 sodium carbonate Inorganic materials 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 21
- VPUHMOLSUUYGEJ-UHFFFAOYSA-N 3-bromo-4-oxo-4-phenylbutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=CC=C1 VPUHMOLSUUYGEJ-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- OKPUICCJRDBRJT-UHFFFAOYSA-N 4-chlorobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(Cl)C=C1 OKPUICCJRDBRJT-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- WKWVTPKUHJOVTI-UHFFFAOYSA-N 4-methoxybenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C=C1 WKWVTPKUHJOVTI-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KOQNISNMBYPFKQ-UHFFFAOYSA-N 2-(1,3-thiazol-5-yl)acetic acid Chemical compound OC(=O)CC1=CN=CS1 KOQNISNMBYPFKQ-UHFFFAOYSA-N 0.000 description 4
- DEFUMLHLEJNWIO-UHFFFAOYSA-N 2-methylbenzenecarbothioamide Chemical compound CC1=CC=CC=C1C(N)=S DEFUMLHLEJNWIO-UHFFFAOYSA-N 0.000 description 4
- VWFCNOXLOVFXKZ-UHFFFAOYSA-N 3-bromo-4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)C(Br)CC(O)=O)C=C1 VWFCNOXLOVFXKZ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000005059 halophenyl group Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 150000003556 thioamides Chemical class 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- IGIVWRJICPRDTF-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-4-phenyl-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC(Cl)=CC=2)=NC=1C1=CC=CC=C1 IGIVWRJICPRDTF-UHFFFAOYSA-N 0.000 description 3
- JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- VSRWEJNGQWEPPH-UHFFFAOYSA-N 4-bromo-5-oxo-5-phenylpentanoic acid Chemical compound OC(=O)CCC(Br)C(=O)C1=CC=CC=C1 VSRWEJNGQWEPPH-UHFFFAOYSA-N 0.000 description 3
- AIPANIYQEBQYGC-UHFFFAOYSA-N 4-bromobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(Br)C=C1 AIPANIYQEBQYGC-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001562 ulcerogenic effect Effects 0.000 description 3
- QBKPJKJQRZFKFT-UHFFFAOYSA-N 2,3-dimethylbenzenecarbothioamide Chemical compound CC1=CC=CC(C(N)=S)=C1C QBKPJKJQRZFKFT-UHFFFAOYSA-N 0.000 description 2
- KYGPUPQKDUNOLW-UHFFFAOYSA-N 2,4-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C(OC)=C1 KYGPUPQKDUNOLW-UHFFFAOYSA-N 0.000 description 2
- WNGOHXAHAKLKAR-UHFFFAOYSA-N 2-(2,4-diphenyl-1,3-thiazol-5-yl)acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 WNGOHXAHAKLKAR-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OOWWTLJQIIZWGE-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)-2-phenyl-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=C(CC(O)=O)SC(C=2C=CC=CC=2)=N1 OOWWTLJQIIZWGE-UHFFFAOYSA-N 0.000 description 2
- NBUMRXASFOKBCR-UHFFFAOYSA-N 2-chloro-6-methylbenzenecarbothioamide Chemical compound CC1=CC=CC(Cl)=C1C(N)=S NBUMRXASFOKBCR-UHFFFAOYSA-N 0.000 description 2
- LZLTYTSQBJHHPG-UHFFFAOYSA-N 3-(2,4-diphenyl-1,3-thiazol-5-yl)propanoic acid Chemical compound C1(=CC=CC=C1)C=1SC(=C(N1)C1=CC=CC=C1)CCC(=O)O LZLTYTSQBJHHPG-UHFFFAOYSA-N 0.000 description 2
- VAJRNXYAGYPYBP-UHFFFAOYSA-N 4-chloro-2-methoxybenzenecarbothioamide Chemical compound COC1=CC(Cl)=CC=C1C(N)=S VAJRNXYAGYPYBP-UHFFFAOYSA-N 0.000 description 2
- CGSMWCIPWDONQU-UHFFFAOYSA-N 4-chloro-2-methylbenzenecarbothioamide Chemical compound CC1=CC(Cl)=CC=C1C(N)=S CGSMWCIPWDONQU-UHFFFAOYSA-N 0.000 description 2
- PTNZSQYXCXOSKS-UHFFFAOYSA-N 4-methoxy-2-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C(C)=C1 PTNZSQYXCXOSKS-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 2
- NKUFFUIDFNMMBA-UHFFFAOYSA-N ethyl 2-[4-(4-chlorophenyl)-2-phenyl-1,3-thiazol-5-yl]acetate Chemical compound C(C)OC(CC1=C(N=C(S1)C1=CC=CC=C1)C1=CC=C(C=C1)Cl)=O NKUFFUIDFNMMBA-UHFFFAOYSA-N 0.000 description 2
- BRBTXTZUNIXYDG-UHFFFAOYSA-N ethyl 2-[4-(4-methoxyphenyl)-2-phenyl-1,3-thiazol-5-yl]acetate Chemical compound C(C)OC(CC1=C(N=C(S1)C1=CC=CC=C1)C1=CC=C(C=C1)OC)=O BRBTXTZUNIXYDG-UHFFFAOYSA-N 0.000 description 2
- IZRWFQDCZXJSBL-UHFFFAOYSA-N ethyl 4-bromo-3-oxo-4-phenylbutanoate Chemical compound BrC(C(CC(=O)OCC)=O)C1=CC=CC=C1 IZRWFQDCZXJSBL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
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- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZQGJZFKITDDUEH-UHFFFAOYSA-N naphthalene-2-carbothioamide Chemical compound C1=CC=CC2=CC(C(=S)N)=CC=C21 ZQGJZFKITDDUEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000001252 propanoic acid ester group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HYKQYVSNFPWGKQ-UHFFFAOYSA-N pyridine-2-carbothioamide Chemical compound NC(=S)C1=CC=CC=N1 HYKQYVSNFPWGKQ-UHFFFAOYSA-N 0.000 description 1
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 description 1
- KPIIGXWUNXGGCP-UHFFFAOYSA-N pyridine-4-carbothioamide Chemical compound NC(=S)C1=CC=NC=C1 KPIIGXWUNXGGCP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005980 thioamidation reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M25/00—Catheters; Hollow probes
- A61M25/01—Introducing, guiding, advancing, emplacing or holding catheters
- A61M25/02—Holding devices, e.g. on the body
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1648872A CH554884A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole bzw. thiazole. |
| CH1717071A CH556351A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole. |
| CH1716871A CH545308A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1716971A CH545309A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1717271A CH536311A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxagole |
| CH1717171A CH545310A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1485573A CH560203A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 | |
| CH1717371A CH560205A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51823/66A GB1145884A (en) | 1966-11-18 | 1966-11-18 | Thiazole derivatives |
| GB5620366A GB1206403A (en) | 1966-12-15 | 1966-12-15 | Oxazoles |
| GB2507667 | 1967-05-31 | ||
| GB2626267A GB1147626A (en) | 1966-07-15 | 1967-06-07 | Thiazole derivatives |
| GB2738267 | 1967-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH528531A true CH528531A (de) | 1972-09-30 |
Family
ID=27516268
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1606467A CH528531A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen aromatischen Charakters |
| CH1717371A CH560205A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 | |
| CH1717071A CH556351A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole. |
| CH1485573A CH560203A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 | |
| CH1716871A CH545308A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1717271A CH536311A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxagole |
| CH1717171A CH545310A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1648872A CH554884A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole bzw. thiazole. |
| CH1716971A CH545309A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1717371A CH560205A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 | |
| CH1717071A CH556351A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole. |
| CH1485573A CH560203A5 (enrdf_load_stackoverflow) | 1966-11-18 | 1967-11-16 | |
| CH1716871A CH545308A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1717271A CH536311A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxagole |
| CH1717171A CH545310A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
| CH1648872A CH554884A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur herstellung neuer trisubstituierter oxazole bzw. thiazole. |
| CH1716971A CH545309A (de) | 1966-11-18 | 1967-11-16 | Verfahren zur Herstellung neuer trisubstituierter Oxazole |
Country Status (12)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2096994A1 (en) * | 1970-07-24 | 1972-03-03 | Roussel Uclaf | 2-para-cyclopropyl phenyl-4-(halo)phenyl-5-thiazolyl - alkanoic acids -antiinflammatory analgesic, antipyretic agents |
| JPS5113375U (enrdf_load_stackoverflow) * | 1974-07-18 | 1976-01-30 | ||
| JPS5182675A (enrdf_load_stackoverflow) * | 1975-01-17 | 1976-07-20 | Tokyo Shibaura Electric Co | |
| GB1543154A (en) * | 1975-05-02 | 1979-03-28 | Lilly Industries Ltd | Urea and carbamate derivatives |
| US4168315A (en) * | 1977-09-28 | 1979-09-18 | The Upjohn Company | Dianisyl thiazole compound, compositions and method of antithrombotic treatment |
| US4697012A (en) * | 1984-07-25 | 1987-09-29 | Merck & Co., Inc. | Morpholino pyridyl thiazole compound |
| IT1204751B (it) * | 1986-01-03 | 1989-03-10 | Therapicon Srl | Derivati idrosolubili dell'acido 4,5 -difenil- 2 -ossazolpropionico,loro preparazione ed utilizzo in composizioni farmaceutiche |
| TW311136B (enrdf_load_stackoverflow) * | 1990-11-30 | 1997-07-21 | Otsuka Pharma Co Ltd | |
| WO1996003392A1 (en) * | 1994-07-27 | 1996-02-08 | G.D. Searle & Co. | Substituted thiazoles for the treatment of inflammation |
| MY128323A (en) | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130759C (enrdf_load_stackoverflow) * | 1965-10-07 |
-
1967
- 1967-10-23 IL IL2880367A patent/IL28803A/xx unknown
- 1967-11-10 FI FI304067A patent/FI50416C/fi active
- 1967-11-13 PL PL12355567A patent/PL72562B1/pl unknown
- 1967-11-15 NL NL6715532.A patent/NL157012B/xx not_active IP Right Cessation
- 1967-11-16 CH CH1606467A patent/CH528531A/de not_active IP Right Cessation
- 1967-11-16 CH CH1717371A patent/CH560205A5/xx not_active IP Right Cessation
- 1967-11-16 CH CH1717071A patent/CH556351A/xx not_active IP Right Cessation
- 1967-11-16 CH CH1485573A patent/CH560203A5/xx not_active IP Right Cessation
- 1967-11-16 BE BE706625A patent/BE706625A/xx not_active IP Right Cessation
- 1967-11-16 CH CH1716871A patent/CH545308A/de not_active IP Right Cessation
- 1967-11-16 CH CH1717271A patent/CH536311A/de not_active IP Right Cessation
- 1967-11-16 CH CH1717171A patent/CH545310A/de not_active IP Right Cessation
- 1967-11-16 CH CH1648872A patent/CH554884A/xx not_active IP Right Cessation
- 1967-11-16 CH CH1716971A patent/CH545309A/de not_active IP Right Cessation
- 1967-11-16 LU LU54891D patent/LU54891A1/xx unknown
- 1967-11-17 JP JP7368167A patent/JPS4938267B1/ja active Pending
- 1967-11-17 DE DE19671795822 patent/DE1795822C2/de not_active Expired
- 1967-11-17 ES ES347319A patent/ES347319A1/es not_active Expired
- 1967-11-17 DE DE19671670005 patent/DE1670005C2/de not_active Expired
- 1967-11-17 FR FR128733A patent/FR8018M/fr not_active Expired
- 1967-11-17 SE SE1585567A patent/SE369307B/xx unknown
- 1967-11-17 FR FR1584222D patent/FR1584222A/fr not_active Expired
-
1973
- 1973-11-28 SE SE7316107A patent/SE422209B/sv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1584222A (enrdf_load_stackoverflow) | 1969-12-19 |
| SE369307B (enrdf_load_stackoverflow) | 1974-08-19 |
| DE1670005A1 (de) | 1970-08-06 |
| CH536311A (de) | 1973-04-30 |
| NL157012B (nl) | 1978-06-15 |
| IL28803A (en) | 1974-05-16 |
| FI50416C (fi) | 1976-03-10 |
| SE422209B (sv) | 1982-02-22 |
| LU54891A1 (enrdf_load_stackoverflow) | 1968-02-08 |
| CH545309A (de) | 1973-12-15 |
| NL6715532A (enrdf_load_stackoverflow) | 1968-05-20 |
| CH545308A (de) | 1973-12-15 |
| JPS4938267B1 (enrdf_load_stackoverflow) | 1974-10-16 |
| CH545310A (de) | 1973-12-15 |
| DE1795822C2 (de) | 1982-07-15 |
| FR8018M (enrdf_load_stackoverflow) | 1970-08-03 |
| CH560205A5 (enrdf_load_stackoverflow) | 1975-03-27 |
| CH556351A (de) | 1974-11-29 |
| BE706625A (enrdf_load_stackoverflow) | 1968-05-16 |
| ES347319A1 (es) | 1969-05-16 |
| FI50416B (enrdf_load_stackoverflow) | 1975-12-01 |
| CH554884A (de) | 1974-10-15 |
| DE1670005C2 (de) | 1982-06-09 |
| PL72562B1 (en) | 1974-08-30 |
| CH560203A5 (enrdf_load_stackoverflow) | 1975-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |