DE3920616A1 - Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate - Google Patents
Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivateInfo
- Publication number
- DE3920616A1 DE3920616A1 DE3920616A DE3920616A DE3920616A1 DE 3920616 A1 DE3920616 A1 DE 3920616A1 DE 3920616 A DE3920616 A DE 3920616A DE 3920616 A DE3920616 A DE 3920616A DE 3920616 A1 DE3920616 A1 DE 3920616A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- hydroxyphenyl
- ethyl
- derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 4
- -1 N- [2- [3,5-di-tert-butyl-4-hydroxyphenyl] ethyl] -3,5-di-tert-butyl-4-hydroxybenzamide 3,5-di-tert-butyl-4-hydroxyphenylacetic acid (3,5-di-tert-butyl-4-hydroxyphenyl) methyl amide Chemical compound 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- RNVYCHNNRVFSDL-UHFFFAOYSA-N 4-(2-aminoethyl)-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(CCN)=CC(C(C)(C)C)=C1O RNVYCHNNRVFSDL-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003585 thioureas Chemical class 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 3
- 229960003912 probucol Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- RUDCXQFBSMSNID-UHFFFAOYSA-N 1,3-bis[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]urea Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCNC(=O)NCCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 RUDCXQFBSMSNID-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- TXBWKXFDLINCMJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(chloromethyl)phenol Chemical compound CC(C)(C)C1=CC(CCl)=CC(C(C)(C)C)=C1O TXBWKXFDLINCMJ-UHFFFAOYSA-N 0.000 description 2
- BEQZSRGZHCDMMH-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC(CC#N)=CC(C(C)(C)C)=C1O BEQZSRGZHCDMMH-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- BJJXHLWLUDYTGC-ANULTFPQSA-N Gestrinone Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](CC)([C@](CC3)(O)C#C)C=C3)C3=C21 BJJXHLWLUDYTGC-ANULTFPQSA-N 0.000 description 2
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- LTUOEBMGHCVNIA-UHFFFAOYSA-N (diisocyanatohydrazinylidene)-oxomethane Chemical compound O=C=NN(N=C=O)N=C=O LTUOEBMGHCVNIA-UHFFFAOYSA-N 0.000 description 1
- UUYOFWFGKXFIHU-UHFFFAOYSA-N 1,3-bis[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]thiourea Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCNC(=S)NCCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 UUYOFWFGKXFIHU-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- HHXPSHRTWQWXCG-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-isocyanatoethyl)phenol Chemical compound CC(C)(C)C1=CC(CCN=C=O)=CC(C(C)(C)C)=C1O HHXPSHRTWQWXCG-UHFFFAOYSA-N 0.000 description 1
- VHVCELDJAZFAHH-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenoxy)-2-methylpropanoic acid Chemical compound CC(C)(C)C1=CC(OC(C)(C)C(O)=O)=CC(C(C)(C)C)=C1O VHVCELDJAZFAHH-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
- GCXNJISCBDJICV-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n-[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]propanamide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GCXNJISCBDJICV-UHFFFAOYSA-N 0.000 description 1
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
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- FAWIHCUUQFGNFK-UHFFFAOYSA-N thiocarbonyl dichloride Chemical compound ClC(Cl)=S.ClC(Cl)=S FAWIHCUUQFGNFK-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- 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
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- 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
- C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
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- 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
- C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/48—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to nitrogen atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C335/12—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3920616A DE3920616A1 (de) | 1989-06-23 | 1989-06-23 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate |
DK90111501.4T DK0404039T3 (da) | 1989-06-23 | 1990-06-19 | Lægemiddel indeholdende di-tert.-butylhydroxy-phenylderivater samt hidtil ukendte derivater |
AT90111501T ATE84413T1 (de) | 1989-06-23 | 1990-06-19 | Arzneimittel, enthaltend di-tert.butylhydroxyphenyl-derivatesowie neue derivate. |
DE9090111501T DE59000750D1 (de) | 1989-06-23 | 1990-06-19 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate. |
EP90111501A EP0404039B1 (de) | 1989-06-23 | 1990-06-19 | Arzneimittel, enthaltend Di-tert.-Butylhydroxyphenyl-Derivate sowie neue Derivate |
JP2164354A JPH0348648A (ja) | 1989-06-23 | 1990-06-25 | 抗動脈硬化薬としての作用を有する医薬及び新規ジ―t―ブチルヒドロキシフエニル誘導体 |
GR920403074T GR3007513T3 (forum.php) | 1989-06-23 | 1993-03-31 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3920616A DE3920616A1 (de) | 1989-06-23 | 1989-06-23 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3920616A1 true DE3920616A1 (de) | 1991-01-03 |
Family
ID=6383432
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3920616A Withdrawn DE3920616A1 (de) | 1989-06-23 | 1989-06-23 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate |
DE9090111501T Expired - Fee Related DE59000750D1 (de) | 1989-06-23 | 1990-06-19 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE9090111501T Expired - Fee Related DE59000750D1 (de) | 1989-06-23 | 1990-06-19 | Arzneimittel, enthaltend di-tert.-butylhydroxyphenyl-derivate sowie neue derivate. |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0404039B1 (forum.php) |
JP (1) | JPH0348648A (forum.php) |
AT (1) | ATE84413T1 (forum.php) |
DE (2) | DE3920616A1 (forum.php) |
DK (1) | DK0404039T3 (forum.php) |
GR (1) | GR3007513T3 (forum.php) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5354782A (en) * | 1991-01-17 | 1994-10-11 | Merrell Dow Pharmaceuticals Inc. | Polyamine phenols as radioprotective agents |
DE4204405A1 (de) * | 1991-08-02 | 1993-02-04 | Boehringer Mannheim Gmbh | Verwendung von di-tert.-butylhydroxyphenyl-derivaten zur therapie von entzuendlichen erkrankungen des magen-darm-traktes |
DE4126662A1 (de) | 1991-08-13 | 1993-02-18 | Boehringer Mannheim Gmbh | Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel |
CA2223948A1 (en) * | 1995-06-07 | 1996-12-19 | Rui Han | Chalcone retinoids and methods of use of same |
US5703130A (en) * | 1995-06-07 | 1997-12-30 | Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences | Chalcone retinoids and methods of use of same |
WO1998016497A1 (fr) * | 1996-10-11 | 1998-04-23 | Kowa Co., Ltd. | Nouveaux composes de diamide et medicaments les contenant |
DE19747644C2 (de) * | 1997-10-29 | 2001-02-22 | Inst Polymerforschung Dresden | Sterisch gehinderte Phenole und Verfahren zu ihrer Herstellung |
WO2003053425A1 (en) * | 2001-12-10 | 2003-07-03 | Yansheng Du | Treatment of neurodegenerative and cardiovascular disorders |
EP1492856A4 (en) | 2002-04-05 | 2010-11-10 | Univ Massachusetts Lowell | POLYMER ANTIOXIDANTS |
US7595074B2 (en) | 2002-04-05 | 2009-09-29 | University Of Massachusetts Lowell | Polymeric antioxidants |
US7323511B2 (en) | 2004-01-21 | 2008-01-29 | University Of Massachusetts Lowell | Post-coupling synthetic approach for polymeric antioxidants |
EA200700117A1 (ru) | 2004-06-24 | 2007-06-29 | Инсайт Корпорейшн | N-замещенные пиперидины и их применение в качестве фармацевтических препаратов |
EP1768954A4 (en) * | 2004-06-24 | 2008-05-28 | Incyte Corp | 2-METHYLPROPANAMIDES AND THEIR USE AS PHARMACEUTICALS |
AU2005269780A1 (en) * | 2004-07-23 | 2006-02-09 | Polnox Corporation | Anti-oxidant macromonomers and polymers and methods of making and using the same |
WO2006060800A1 (en) | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
EP1817393A2 (en) | 2004-12-03 | 2007-08-15 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
EP1861484A2 (en) | 2005-02-22 | 2007-12-05 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
EP1866279A2 (en) | 2005-03-25 | 2007-12-19 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
WO2007050985A2 (en) | 2005-10-27 | 2007-05-03 | Polnox Corporation | Macromolecular antioxidants based on stξrically hindered phenolic phosphites |
EP1966293A1 (en) | 2005-10-27 | 2008-09-10 | Polnox Corporation | Stabilized polyolefin compositions |
EP1963468A1 (en) | 2005-12-02 | 2008-09-03 | Polnox Corporation | Lubricant oil compositions |
WO2008005358A2 (en) | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
US20130143933A1 (en) * | 2011-11-09 | 2013-06-06 | Trt Pharma Inc. | Targeted correction of a genetic defect in cancer therapy |
EP3057930B1 (en) | 2013-10-17 | 2020-03-25 | Swimc Llc | Di(amido(alkyl)phenol) compounds and polymers formed therefrom |
WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
BR112016026342B1 (pt) | 2014-05-19 | 2022-03-03 | Swimc Llc | Artigo |
US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3584047A (en) * | 1967-12-29 | 1971-06-08 | Geigy Chem Corp | Alkylhydroxyphenyl polyamides |
US3763166A (en) * | 1967-12-29 | 1973-10-02 | Ciba Geigy Corp | N,n'-bis(3-(3,5-di-t-butyl-4-hydroxyphenyl)lower alkanoyl)piperazines |
DE2240609A1 (de) * | 1972-08-18 | 1974-02-28 | Hoechst Ag | Stoffwechselwirksame derivate der 4-hydroxy-3,5-di-alkylphenyl-propionsaeure |
GB1405767A (en) * | 1972-12-14 | 1975-09-10 | Ethyl Corp | Method formulation and pharmaceutical composition for reducing plasma lipid levels |
DE2721398A1 (de) * | 1976-05-19 | 1977-12-01 | Ciba Geigy Ag | Alkylphenol-stabilisatoren |
US4066610A (en) * | 1976-07-14 | 1978-01-03 | Dart Industries, Inc. | Stabilized pigmented polyolefin compositions |
NL7905000A (nl) * | 1978-09-25 | 1980-03-27 | Cincinnati Milacron Chem | Gehinderde fenolverbindingen, alsmede organische mate- rialen die met behulp daarvan gestabiliseerd zijn tegen oxydatieve aantasting. |
US4473579A (en) * | 1982-01-26 | 1984-09-25 | American Cyanamid Company | Antiatherosclerotic tetrasubstituted ureas and thioureas |
US4397868A (en) * | 1982-01-26 | 1983-08-09 | American Cyanamid Company | Method of treating atherosclerosis with trisubstituted ureas |
US4835189A (en) * | 1987-06-05 | 1989-05-30 | G. D. Searle & Co. | Phenolic thioalkylamides as inhibitors of 5-lipoxygenase |
-
1989
- 1989-06-23 DE DE3920616A patent/DE3920616A1/de not_active Withdrawn
-
1990
- 1990-06-19 DK DK90111501.4T patent/DK0404039T3/da active
- 1990-06-19 AT AT90111501T patent/ATE84413T1/de not_active IP Right Cessation
- 1990-06-19 DE DE9090111501T patent/DE59000750D1/de not_active Expired - Fee Related
- 1990-06-19 EP EP90111501A patent/EP0404039B1/de not_active Expired - Lifetime
- 1990-06-25 JP JP2164354A patent/JPH0348648A/ja active Pending
-
1993
- 1993-03-31 GR GR920403074T patent/GR3007513T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
JPH0348648A (ja) | 1991-03-01 |
DK0404039T3 (da) | 1993-04-19 |
ATE84413T1 (de) | 1993-01-15 |
EP0404039A1 (de) | 1990-12-27 |
EP0404039B1 (de) | 1993-01-13 |
DE59000750D1 (de) | 1993-02-25 |
GR3007513T3 (forum.php) | 1993-08-31 |
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