NO764012L - - Google Patents
Info
- Publication number
- NO764012L NO764012L NO764012A NO764012A NO764012L NO 764012 L NO764012 L NO 764012L NO 764012 A NO764012 A NO 764012A NO 764012 A NO764012 A NO 764012A NO 764012 L NO764012 L NO 764012L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- radical
- hydrogen
- compound
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- -1 carbonyl radical Chemical class 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 75
- 239000002253 acid Substances 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 37
- 239000007858 starting material Substances 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000003254 radicals Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 8
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- CQSIDCYPXUKBNE-UHFFFAOYSA-N methyl 2-[4-(2-formamidoacetyl)phenyl]sulfanylacetate Chemical compound COC(=O)CSC1=CC=C(C(=O)CNC=O)C=C1 CQSIDCYPXUKBNE-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- NDRUTHFTDCUQOA-UHFFFAOYSA-N methyl 2-[4-(2-aminoacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)CN)C=C1 NDRUTHFTDCUQOA-UHFFFAOYSA-N 0.000 claims description 4
- SQHYUSJORGWXLZ-UHFFFAOYSA-N methyl 2-[4-(2-formamidoacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)CNC=O)C=C1 SQHYUSJORGWXLZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- GPYVBDZBJBAROZ-UHFFFAOYSA-N 2-[4-(2-aminoacetyl)phenoxy]acetic acid Chemical compound NCC(=O)C1=CC=C(OCC(O)=O)C=C1 GPYVBDZBJBAROZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- SPVFIZYNBJGTQQ-UHFFFAOYSA-N methyl 2-[4-(2-aminoacetyl)phenyl]sulfanylacetate Chemical compound COC(=O)CSC1=CC=C(C(=O)CN)C=C1 SPVFIZYNBJGTQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 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
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000032544 Cicatrix Diseases 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000037387 scars Effects 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 57
- 239000000203 mixture Substances 0.000 description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 102000009123 Fibrin Human genes 0.000 description 18
- 108010073385 Fibrin Proteins 0.000 description 18
- 229950003499 fibrin Drugs 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 150000001540 azides Chemical class 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 230000009467 reduction Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- UGJREGAGQDKXPR-UHFFFAOYSA-N methyl 2-[4-(2-aminoacetyl)phenoxy]acetate;hydrochloride Chemical compound Cl.COC(=O)COC1=CC=C(C(=O)CN)C=C1 UGJREGAGQDKXPR-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 208000007536 Thrombosis Diseases 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003701 inert diluent Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- MULCHMGSUCDHNN-UHFFFAOYSA-N 3-[4-(2-chloroacetyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(C(=O)CCl)C=C1 MULCHMGSUCDHNN-UHFFFAOYSA-N 0.000 description 5
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VACHEQBTEGIMEH-UHFFFAOYSA-N propan-2-yl 2-(4-acetylphenoxy)acetate Chemical compound CC(C)OC(=O)COC1=CC=C(C(C)=O)C=C1 VACHEQBTEGIMEH-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 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 5
- 238000012360 testing method Methods 0.000 description 5
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 230000002378 acidificating effect Effects 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- HPXGIVFLGKNDOB-UHFFFAOYSA-N 2-[4-(2-bromoacetyl)phenoxy]-1-morpholin-4-ylethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1OCC(=O)N1CCOCC1 HPXGIVFLGKNDOB-UHFFFAOYSA-N 0.000 description 3
- HRFLCOPAVNRDRN-UHFFFAOYSA-N 2-[4-(2-chloroacetyl)phenoxy]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)COC1=CC=C(C(=O)CCl)C=C1 HRFLCOPAVNRDRN-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 241000786363 Rhampholeon spectrum Species 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- SVJPNJJYQDZSRE-UHFFFAOYSA-N ethyl 2-[4-(2-azidoacetyl)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(C(=O)CN=[N+]=[N-])C=C1 SVJPNJJYQDZSRE-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- QVZGUDBOSUAKTA-UHFFFAOYSA-N methyl 2-[4-(2-azidoacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)CN=[N+]=[N-])C=C1 QVZGUDBOSUAKTA-UHFFFAOYSA-N 0.000 description 3
- CDULGSLSRWNKQX-UHFFFAOYSA-N methyl 2-[4-(2-azidoacetyl)phenyl]sulfanylacetate Chemical compound COC(=O)CSC1=CC=C(C(=O)CN=[N+]=[N-])C=C1 CDULGSLSRWNKQX-UHFFFAOYSA-N 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- WZTUDEBHYBHGHD-UHFFFAOYSA-N methyl 3-[4-(2-chloroacetyl)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(C(=O)CCl)C=C1 WZTUDEBHYBHGHD-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IWZIHRDNGZLBRJ-UHFFFAOYSA-N ethyl 2-(4-acetylphenoxy)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(C(C)=O)C=C1 IWZIHRDNGZLBRJ-UHFFFAOYSA-N 0.000 description 1
- DNTVXNURGLHBDY-UHFFFAOYSA-N ethyl 2-[4-(2-aminoacetyl)phenoxy]-2-methylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)(C)OC1=CC=C(C(=O)CN)C=C1 DNTVXNURGLHBDY-UHFFFAOYSA-N 0.000 description 1
- YPSNGYBSHYETIV-UHFFFAOYSA-N ethyl 2-[4-(2-aminoacetyl)phenoxy]acetate;hydrochloride Chemical compound Cl.CCOC(=O)COC1=CC=C(C(=O)CN)C=C1 YPSNGYBSHYETIV-UHFFFAOYSA-N 0.000 description 1
- WBFUQMUJGSUBIT-UHFFFAOYSA-N ethyl 2-[4-(2-aminoacetyl)phenoxy]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)OC1=CC=C(C(=O)CN)C=C1 WBFUQMUJGSUBIT-UHFFFAOYSA-N 0.000 description 1
- IQNBTWADYKHANG-UHFFFAOYSA-N ethyl 2-phenoxypropanoate Chemical compound CCOC(=O)C(C)OC1=CC=CC=C1 IQNBTWADYKHANG-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940106780 human fibrinogen Drugs 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- IYUKFAFDFHZKPI-UHFFFAOYSA-N hydron;methyl 2-aminopropanoate;chloride Chemical compound Cl.COC(=O)C(C)N IYUKFAFDFHZKPI-UHFFFAOYSA-N 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-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
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- VGCCRSXMNCBMIA-JTQLQIEISA-N methyl (2s)-2-[3-[4-(2-aminoacetyl)phenyl]propanoylamino]propanoate Chemical compound COC(=O)[C@H](C)NC(=O)CCC1=CC=C(C(=O)CN)C=C1 VGCCRSXMNCBMIA-JTQLQIEISA-N 0.000 description 1
- DHJVXENYKAYHIJ-JTQLQIEISA-N methyl (2s)-2-[3-[4-(2-chloroacetyl)phenyl]propanoylamino]propanoate Chemical compound COC(=O)[C@H](C)NC(=O)CCC1=CC=C(C(=O)CCl)C=C1 DHJVXENYKAYHIJ-JTQLQIEISA-N 0.000 description 1
- YGATUAAPJYMNQG-UHFFFAOYSA-N methyl 2-(3-acetylphenoxy)acetate Chemical compound COC(=O)COC1=CC=CC(C(C)=O)=C1 YGATUAAPJYMNQG-UHFFFAOYSA-N 0.000 description 1
- IICFBQQVVDPOHE-UHFFFAOYSA-N methyl 2-(4-carbonochloridoylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(C(Cl)=O)C=C1 IICFBQQVVDPOHE-UHFFFAOYSA-N 0.000 description 1
- LBOUUZPMJRYIIJ-UHFFFAOYSA-N methyl 2-[3-(2-aminoacetyl)phenoxy]acetate;hydrochloride Chemical compound Cl.COC(=O)COC1=CC=CC(C(=O)CN)=C1 LBOUUZPMJRYIIJ-UHFFFAOYSA-N 0.000 description 1
- FSTQEVMTHYUQHX-UHFFFAOYSA-N methyl 2-[4-(2-aminoacetyl)phenoxy]propanoate;hydrochloride Chemical compound Cl.COC(=O)C(C)OC1=CC=C(C(=O)CN)C=C1 FSTQEVMTHYUQHX-UHFFFAOYSA-N 0.000 description 1
- IUFKUHKOLQVVPL-UHFFFAOYSA-N methyl 2-[4-(2-chloroacetyl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=C(C(=O)CCl)C=C1 IUFKUHKOLQVVPL-UHFFFAOYSA-N 0.000 description 1
- FEMVKRLWWZDGQR-UHFFFAOYSA-N methyl 2-[4-(2-formamidoacetyl)phenyl]sulfinylacetate Chemical compound COC(=O)CS(=O)C1=CC=C(C(=O)CNC=O)C=C1 FEMVKRLWWZDGQR-UHFFFAOYSA-N 0.000 description 1
- BLDAGWMQKUFAMZ-UHFFFAOYSA-N methyl 2-[4-[2-(ethoxycarbonylamino)acetyl]phenoxy]acetate Chemical compound CCOC(=O)NCC(=O)C1=CC=C(OCC(=O)OC)C=C1 BLDAGWMQKUFAMZ-UHFFFAOYSA-N 0.000 description 1
- PMWNXHYPYJBREK-UHFFFAOYSA-N methyl 2-amino-3-[4-(2-methoxy-2-oxoethoxy)phenyl]-3-oxopropanoate;hydrochloride Chemical compound Cl.COC(=O)COC1=CC=C(C(=O)C(N)C(=O)OC)C=C1 PMWNXHYPYJBREK-UHFFFAOYSA-N 0.000 description 1
- CRXFROMHHBMNAB-UHFFFAOYSA-N methyl 2-isocyanoacetate Chemical compound COC(=O)C[N+]#[C-] CRXFROMHHBMNAB-UHFFFAOYSA-N 0.000 description 1
- MUNSXQQODXYRKI-UHFFFAOYSA-N methyl 2-phenylsulfanylacetate Chemical compound COC(=O)CSC1=CC=CC=C1 MUNSXQQODXYRKI-UHFFFAOYSA-N 0.000 description 1
- NXWIFZIJEPKPTE-UHFFFAOYSA-N methyl 3-[4-(2-aminoacetyl)phenyl]propanoate;hydrochloride Chemical compound Cl.COC(=O)CCC1=CC=C(C(=O)CN)C=C1 NXWIFZIJEPKPTE-UHFFFAOYSA-N 0.000 description 1
- SSRVFHVMEFTYQS-UHFFFAOYSA-N methyl 4-phenoxybutanoate Chemical compound COC(=O)CCCOC1=CC=CC=C1 SSRVFHVMEFTYQS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- CAKRCYBQYAFXDI-UHFFFAOYSA-N n,n-diethyl-2-phenoxyacetamide Chemical compound CCN(CC)C(=O)COC1=CC=CC=C1 CAKRCYBQYAFXDI-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
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- LBXOOGFSONVWLV-UHFFFAOYSA-N propyl 2-[4-(2-aminoacetyl)phenyl]acetate;hydrochloride Chemical compound Cl.CCCOC(=O)CC1=CC=C(C(=O)CN)C=C1 LBXOOGFSONVWLV-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AUMHDRMJJNZTPB-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(O)=C1CCS(=O)C1=CC=CC=C1 AUMHDRMJJNZTPB-UHFFFAOYSA-N 0.000 description 1
- 229960003329 sulfinpyrazone Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- KRTNWFAEAZIUJL-UHFFFAOYSA-L zinc methyl 2-[4-(2-aminoacetyl)phenyl]sulfanylacetate dichloride hydrochloride Chemical compound [Cl-].[Zn+2].Cl.NCC(=O)C1=CC=C(SCC(=O)OC)C=C1.[Cl-] KRTNWFAEAZIUJL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C07D263/34—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 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
-
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- 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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48402/75A GB1559977A (en) | 1975-11-25 | 1975-11-25 | Amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO764012L true NO764012L (fr) | 1977-05-26 |
Family
ID=10448487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO764012A NO764012L (fr) | 1975-11-25 | 1976-11-24 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4105790A (fr) |
| JP (2) | JPS5265240A (fr) |
| AR (1) | AR215871A1 (fr) |
| AT (1) | AT348993B (fr) |
| AU (1) | AU503657B2 (fr) |
| BE (1) | BE848707A (fr) |
| CA (1) | CA1068695A (fr) |
| CH (1) | CH624383A5 (fr) |
| CS (1) | CS196333B2 (fr) |
| DD (1) | DD127474A5 (fr) |
| DE (1) | DE2653635C2 (fr) |
| DK (1) | DK531276A (fr) |
| ES (2) | ES453632A1 (fr) |
| FI (1) | FI763399A (fr) |
| FR (1) | FR2332747A1 (fr) |
| GB (1) | GB1559977A (fr) |
| IE (1) | IE44030B1 (fr) |
| IL (1) | IL50904A (fr) |
| IN (1) | IN145003B (fr) |
| LU (1) | LU76251A1 (fr) |
| NL (1) | NL7613081A (fr) |
| NO (1) | NO764012L (fr) |
| NZ (1) | NZ182581A (fr) |
| PL (2) | PL105799B1 (fr) |
| PT (1) | PT65892B (fr) |
| SE (1) | SE7613079L (fr) |
| SU (1) | SU722481A3 (fr) |
| ZA (1) | ZA766696B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02130656U (fr) * | 1989-03-31 | 1990-10-29 | ||
| JPH028457U (fr) * | 1988-07-01 | 1990-01-19 | ||
| US5348969A (en) * | 1992-04-03 | 1994-09-20 | Bristol-Myers Squibb Company | Diphenyloxazolyl-oxazoles as platelet aggregation inhibitors |
| US6147216A (en) * | 1993-06-25 | 2000-11-14 | Merrell Pharmaceuticals Inc. | Intermediates useful for the preparation of antihistaminic piperidine derivatives |
| WO1995000480A1 (fr) | 1993-06-25 | 1995-01-05 | Merrell Pharmaceuticals Inc. | Nouveaux intermediaires utilises dans la preparation de derives de piperidine 4-diphenylmethyl/diphenylmethoxy antihistaminiques |
| US6673933B2 (en) | 1998-07-02 | 2004-01-06 | Aventis Pharmaceutical Inc. | Antihistaminic piperidine derivatives and intermediates for the preparation thereof |
| US6683094B2 (en) | 1998-07-02 | 2004-01-27 | Aventis Pharmaceuticals Inc. | Antihistaminic piperidine derivatives and intermediates for the preparation thereof |
| FR2880887B1 (fr) * | 2005-01-14 | 2009-01-30 | Merck Sante Soc Par Actions Si | Derives d'hydroxyphenols, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
| TW200740779A (en) | 2005-07-22 | 2007-11-01 | Mitsubishi Pharma Corp | Intermediate compound for synthesizing pharmaceutical agent and production method thereof |
| WO2016009871A1 (fr) * | 2014-07-16 | 2016-01-21 | 株式会社Adeka | Composition photosensible |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH543472A (fr) * | 1969-01-31 | 1973-10-31 | Orchimed Sa | Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques |
-
1975
- 1975-11-25 GB GB48402/75A patent/GB1559977A/en not_active Expired
-
1976
- 1976-11-08 IE IE2474/76A patent/IE44030B1/en unknown
- 1976-11-09 NZ NZ182581A patent/NZ182581A/xx unknown
- 1976-11-09 ZA ZA766696A patent/ZA766696B/xx unknown
- 1976-11-09 US US05/740,195 patent/US4105790A/en not_active Expired - Lifetime
- 1976-11-10 IN IN2024/CAL/76A patent/IN145003B/en unknown
- 1976-11-12 CA CA265,534A patent/CA1068695A/fr not_active Expired
- 1976-11-14 IL IL50904A patent/IL50904A/xx unknown
- 1976-11-15 AU AU19625/76A patent/AU503657B2/en not_active Expired
- 1976-11-23 LU LU76251A patent/LU76251A1/xx unknown
- 1976-11-23 PL PL1976205925A patent/PL105799B1/pl unknown
- 1976-11-23 PL PL1976193861A patent/PL105491B1/pl unknown
- 1976-11-23 SE SE7613079A patent/SE7613079L/xx unknown
- 1976-11-24 NL NL7613081A patent/NL7613081A/xx not_active Application Discontinuation
- 1976-11-24 AT AT870976A patent/AT348993B/de not_active IP Right Cessation
- 1976-11-24 FR FR7635385A patent/FR2332747A1/fr active Granted
- 1976-11-24 NO NO764012A patent/NO764012L/no unknown
- 1976-11-24 BE BE172664A patent/BE848707A/fr not_active IP Right Cessation
- 1976-11-24 DD DD195943A patent/DD127474A5/xx unknown
- 1976-11-24 CS CS767604A patent/CS196333B2/cs unknown
- 1976-11-24 CH CH1480376A patent/CH624383A5/de not_active IP Right Cessation
- 1976-11-25 DE DE2653635A patent/DE2653635C2/de not_active Expired
- 1976-11-25 PT PT65892A patent/PT65892B/pt unknown
- 1976-11-25 DK DK531276A patent/DK531276A/da not_active Application Discontinuation
- 1976-11-25 FI FI763399A patent/FI763399A/fi not_active Application Discontinuation
- 1976-11-25 ES ES453632A patent/ES453632A1/es not_active Expired
- 1976-11-25 AR AR265606A patent/AR215871A1/es active
- 1976-11-25 JP JP51141767A patent/JPS5265240A/ja active Granted
-
1977
- 1977-12-16 ES ES465152A patent/ES465152A1/es not_active Expired
-
1978
- 1978-02-13 SU SU782579897A patent/SU722481A3/ru active
-
1985
- 1985-11-08 JP JP60249137A patent/JPS61158922A/ja active Granted
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