CH624099A5 - - Google Patents
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- Publication number
- CH624099A5 CH624099A5 CH766080A CH766080A CH624099A5 CH 624099 A5 CH624099 A5 CH 624099A5 CH 766080 A CH766080 A CH 766080A CH 766080 A CH766080 A CH 766080A CH 624099 A5 CH624099 A5 CH 624099A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- cyclohexylphenyl
- acetic acid
- hydroxyl group
- Prior art date
Links
- -1 cyclohexyl-benzyl compound Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000007530 organic bases Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005832 cyclohexylphenylene group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[*:2])C1([H])C([H])([H])C([H])([H])C([H])([*:1])C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- 229960000583 acetic acid Drugs 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 239000012362 glacial acetic acid Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 10
- VBQYIRCVCGYROB-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfinyl]acetic acid Chemical group C1=CC(C(C)S(=O)CC(O)=O)=CC=C1C1CCCCC1 VBQYIRCVCGYROB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000740 bleeding effect Effects 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- SPUJKQNUMJYSGC-UHFFFAOYSA-N 2-[1-(3-chloro-4-cyclohexylphenyl)ethylsulfinyl]acetic acid Chemical compound ClC1=CC(C(C)S(=O)CC(O)=O)=CC=C1C1CCCCC1 SPUJKQNUMJYSGC-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- CHNLGGUBYZDCJC-UHFFFAOYSA-N ethyl 2-[1-(3-chloro-4-cyclohexylphenyl)ethylsulfinyl]acetate Chemical compound ClC1=CC(C(C)S(=O)CC(=O)OCC)=CC=C1C1CCCCC1 CHNLGGUBYZDCJC-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 2
- TZTXHCXTDRRXFG-UHFFFAOYSA-N 1-(1-chloroethyl)-4-cyclohexylbenzene Chemical compound C1=CC(C(Cl)C)=CC=C1C1CCCCC1 TZTXHCXTDRRXFG-UHFFFAOYSA-N 0.000 description 1
- CYEIZTMWVNXOQH-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1CCCCC1 CYEIZTMWVNXOQH-UHFFFAOYSA-N 0.000 description 1
- MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 1
- KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- WIJOXYWRGOPMTI-UHFFFAOYSA-N 2,2-dimethyl-1-(2,4,6-trimethylphenyl)propan-1-one Chemical compound CC1=CC(C)=C(C(=O)C(C)(C)C)C(C)=C1 WIJOXYWRGOPMTI-UHFFFAOYSA-N 0.000 description 1
- SMRFHZDVSXMXGB-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfanyl]acetic acid Chemical compound C1=CC(C(SCC(O)=O)C)=CC=C1C1CCCCC1 SMRFHZDVSXMXGB-UHFFFAOYSA-N 0.000 description 1
- YNSUCOJZCQFBJP-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfinyl]acetamide Chemical compound C1=CC(C(C)S(=O)CC(N)=O)=CC=C1C1CCCCC1 YNSUCOJZCQFBJP-UHFFFAOYSA-N 0.000 description 1
- KZSWRACHHTYQMX-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfonyl]-1-piperidin-1-ylethanone Chemical compound C1CCCCN1C(=O)CS(=O)(=O)C(C)C(C=C1)=CC=C1C1CCCCC1 KZSWRACHHTYQMX-UHFFFAOYSA-N 0.000 description 1
- VCJIPYMZADGPEU-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfonyl]acetamide Chemical compound C1=CC(C(C)S(=O)(=O)CC(N)=O)=CC=C1C1CCCCC1 VCJIPYMZADGPEU-UHFFFAOYSA-N 0.000 description 1
- XNHXDDIIVQFKMK-UHFFFAOYSA-N 2-[1-(4-cyclohexylphenyl)ethylsulfonyl]acetic acid Chemical compound C1=CC(C(C)S(=O)(=O)CC(O)=O)=CC=C1C1CCCCC1 XNHXDDIIVQFKMK-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- YPWBBPSNTYFMEH-UHFFFAOYSA-N 3-methylbutyl 2-[1-(4-cyclohexylphenyl)ethylsulfinyl]acetate Chemical compound C1=CC(C(C)S(=O)CC(=O)OCCC(C)C)=CC=C1C1CCCCC1 YPWBBPSNTYFMEH-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 241001552669 Adonis annua Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 208000031104 Arterial Occlusive disease Diseases 0.000 description 1
- AXFSFQCCXJNPMA-UHFFFAOYSA-N C=1C=C(C2CCCCC2)C(Cl)=CC=1C(C)SCC(=O)N1CCOCC1 Chemical compound C=1C=C(C2CCCCC2)C(Cl)=CC=1C(C)SCC(=O)N1CCOCC1 AXFSFQCCXJNPMA-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N CD3OD Substances [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
- WMGWKLPEWPYTLI-UHFFFAOYSA-N ClC=1C=C(C=CC1C1CCCCC1)C(C)S(=O)CC(=O)N1CCCCC1 Chemical compound ClC=1C=C(C=CC1C1CCCCC1)C(C)S(=O)CC(=O)N1CCCCC1 WMGWKLPEWPYTLI-UHFFFAOYSA-N 0.000 description 1
- 206010014513 Embolism arterial Diseases 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000006502 antiplatelets effects Effects 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- MXBYZYUVYQXYPG-UHFFFAOYSA-N benzyl 2-[1-(4-cyclohexylphenyl)ethylsulfinyl]acetate Chemical compound C=1C=CC=CC=1COC(=O)CS(=O)C(C)C(C=C1)=CC=C1C1CCCCC1 MXBYZYUVYQXYPG-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VKYDZIYKVSNIRK-UHFFFAOYSA-N methyl 2-[1-(4-cyclohexylphenyl)ethylsulfonyl]acetate Chemical compound C1=CC(C(C)S(=O)(=O)CC(=O)OC)=CC=C1C1CCCCC1 VKYDZIYKVSNIRK-UHFFFAOYSA-N 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2546319A DE2546319C2 (de) | 1975-10-16 | 1975-10-16 | Cyclohexylphenyl-Derivate, Verfahren zu deren Herstellung und diese enthaltende Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624099A5 true CH624099A5 (en, 2012) | 1981-07-15 |
Family
ID=5959276
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1302676A CH622777A5 (en, 2012) | 1975-10-16 | 1976-10-14 | |
| CH766080A CH624099A5 (en, 2012) | 1975-10-16 | 1980-10-14 | |
| CH766180A CH625210A5 (en, 2012) | 1975-10-16 | 1980-10-14 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1302676A CH622777A5 (en, 2012) | 1975-10-16 | 1976-10-14 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH766180A CH625210A5 (en, 2012) | 1975-10-16 | 1980-10-14 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4062973A (en, 2012) |
| JP (1) | JPS6016412B2 (en, 2012) |
| AT (1) | AT344150B (en, 2012) |
| AU (1) | AU507034B2 (en, 2012) |
| BE (1) | BE847373A (en, 2012) |
| CH (3) | CH622777A5 (en, 2012) |
| DE (1) | DE2546319C2 (en, 2012) |
| DK (1) | DK153942C (en, 2012) |
| ES (2) | ES451710A1 (en, 2012) |
| FI (1) | FI62066C (en, 2012) |
| FR (1) | FR2327767A1 (en, 2012) |
| GB (1) | GB1524637A (en, 2012) |
| HK (1) | HK16582A (en, 2012) |
| IE (1) | IE44177B1 (en, 2012) |
| KE (1) | KE3177A (en, 2012) |
| LU (1) | LU76009A1 (en, 2012) |
| MY (1) | MY8200196A (en, 2012) |
| NL (1) | NL180563C (en, 2012) |
| NO (1) | NO142524C (en, 2012) |
| SE (1) | SE433210B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2528041A1 (fr) * | 1982-06-04 | 1983-12-09 | Lafon Labor | Acides halogenobenzhydrylsulfinylacetohydroxamiques, procede de preparation et utilisation en therapeutique |
| US5256692A (en) * | 1992-01-07 | 1993-10-26 | E. R. Squibb & Sons, Inc. | Sulfur-containing HMG-COA reductase inhibitors |
| US6362183B1 (en) | 1997-03-04 | 2002-03-26 | G. D. Searle & Company | Aromatic sulfonyl alpha-hydroxy hydroxamic acid compounds |
| ITMI20020991A1 (it) * | 2002-05-10 | 2003-11-10 | Dinamite Dipharma S P A In For | Procedimento per la sintesi del modafinil |
| US7449481B2 (en) * | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
| CN112919984B (zh) * | 2021-04-16 | 2022-03-08 | 安徽硒无忧现代农业科技有限公司 | 一种生态化富硒有机营养液及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1532701A (fr) * | 1966-06-23 | 1968-07-12 | Ici Ltd | Nouveaux dérivés aryliques d'acides carboxyliques |
| GB1121027A (en) * | 1966-06-23 | 1968-07-24 | Ici Ltd | New carboxylic acid derivatives, processes for the preparation thereof and compositions containing the same |
| US4000183A (en) * | 1972-11-01 | 1976-12-28 | Ciba-Geigy Corporation | Adamantyl-phenoxy- and phenylthio-alkyl-alkanoyl esters |
| DK422774A (en, 2012) * | 1973-09-18 | 1975-05-20 | Ciba Geigy Ag | |
| AT336589B (de) * | 1974-05-20 | 1977-05-10 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen biphenylderivaten |
-
1975
- 1975-10-16 DE DE2546319A patent/DE2546319C2/de not_active Expired
-
1976
- 1976-09-21 ES ES451710A patent/ES451710A1/es not_active Expired
- 1976-09-28 AT AT717076A patent/AT344150B/de not_active IP Right Cessation
- 1976-09-29 DK DK438976A patent/DK153942C/da not_active IP Right Cessation
- 1976-09-30 FI FI762785A patent/FI62066C/fi not_active IP Right Cessation
- 1976-10-06 US US05/730,122 patent/US4062973A/en not_active Expired - Lifetime
- 1976-10-12 NL NLAANVRAGE7611254,A patent/NL180563C/xx active Search and Examination
- 1976-10-14 IE IE2267/76A patent/IE44177B1/en unknown
- 1976-10-14 CH CH1302676A patent/CH622777A5/de not_active IP Right Cessation
- 1976-10-14 LU LU76009A patent/LU76009A1/xx unknown
- 1976-10-15 NO NO763532A patent/NO142524C/no unknown
- 1976-10-15 JP JP51123769A patent/JPS6016412B2/ja not_active Expired
- 1976-10-15 SE SE7611494A patent/SE433210B/xx not_active IP Right Cessation
- 1976-10-15 BE BE171583A patent/BE847373A/xx not_active IP Right Cessation
- 1976-10-15 AU AU18738/76A patent/AU507034B2/en not_active Expired
- 1976-10-15 GB GB43008/76A patent/GB1524637A/en not_active Expired
- 1976-10-15 FR FR7631122A patent/FR2327767A1/fr active Granted
-
1977
- 1977-03-25 ES ES457227A patent/ES457227A1/es not_active Expired
-
1980
- 1980-10-14 CH CH766080A patent/CH624099A5/de not_active IP Right Cessation
- 1980-10-14 CH CH766180A patent/CH625210A5/de not_active IP Right Cessation
-
1981
- 1981-12-11 KE KE3177A patent/KE3177A/xx unknown
-
1982
- 1982-04-08 HK HK165/82A patent/HK16582A/xx unknown
- 1982-12-30 MY MY196/82A patent/MY8200196A/xx unknown
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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased | ||
| PL | Patent ceased |