DD223148A5 - Verfahren zur herstellung von gem-diaminoal-kanderivaten - Google Patents

Verfahren zur herstellung von gem-diaminoal-kanderivaten Download PDF

Info

Publication number: DD223148A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; item; product; aspartyl; hydrogen
Prior art date: 1983-06-13

Application number

DD84263717A

Other languages

German (de)

English (en)

Inventor

Michael St Verlander

William D Fuller

Murray Goodman

Original Assignee

Cumberland Packing Corp

Priority date (The priority date 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 date listed.)

1983-06-13

Filing date

1984-06-01

Publication date

1985-06-05

1984-06-01 Application filed by Cumberland Packing Corp filed Critical Cumberland Packing Corp

1985-06-05 Publication of DD223148A5 publication Critical patent/DD223148A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 64
150000001875 compounds Chemical class 0.000 claims abstract description 57
235000003599 food sweetener Nutrition 0.000 claims abstract description 45
239000003765 sweetening agent Substances 0.000 claims abstract description 45
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 22
230000008569 process Effects 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 9
235000013305 food Nutrition 0.000 claims abstract description 6
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
125000005592 polycycloalkyl group Polymers 0.000 claims abstract description 4
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 3
125000002091 cationic group Chemical group 0.000 claims abstract description 3
239000000047 product Substances 0.000 claims description 118
-1 Diycloalkyi Chemical group 0.000 claims description 49
229930006000 Sucrose Natural products 0.000 claims description 29
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 29
239000005720 sucrose Substances 0.000 claims description 29
239000007787 solid Substances 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
150000003862 amino acid derivatives Chemical class 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
230000015572 biosynthetic process Effects 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
229940024606 amino acid Drugs 0.000 claims description 11
235000001014 amino acid Nutrition 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
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 claims description 10
150000001413 amino acids Chemical class 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
150000001509 aspartic acid derivatives Chemical class 0.000 claims description 7
235000019204 saccharin Nutrition 0.000 claims description 7
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 7
229940081974 saccharin Drugs 0.000 claims description 7
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
230000009466 transformation Effects 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical compound OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 claims description 5
235000003704 aspartic acid Nutrition 0.000 claims description 5
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 5
235000009508 confectionery Nutrition 0.000 claims description 5
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
238000003776 cleavage reaction Methods 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
230000007017 scission Effects 0.000 claims description 4
108010016626 Dipeptides Proteins 0.000 claims description 3
206010013911 Dysgeusia Diseases 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000007857 degradation product Substances 0.000 claims description 3
125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
150000003140 primary amides Chemical class 0.000 claims description 3
ARSRLTZFKLVDPV-UHFFFAOYSA-N 1,2,2,5,5-pentamethylcyclopentan-1-ol Chemical compound CC1(C)CCC(C)(C)C1(C)O ARSRLTZFKLVDPV-UHFFFAOYSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 2
239000008122 artificial sweetener Substances 0.000 claims description 2
235000021311 artificial sweeteners Nutrition 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
230000001131 transforming effect Effects 0.000 claims 3
150000001450 anions Chemical class 0.000 claims 2
238000010411 cooking Methods 0.000 claims 2
239000000796 flavoring agent Substances 0.000 claims 2
235000019634 flavors Nutrition 0.000 claims 2
BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims 2
NASGYMXDTSFRMR-UHFFFAOYSA-N 1,1,2,3,3-pentamethylcyclopentane Chemical compound CC1C(C)(C)CCC1(C)C NASGYMXDTSFRMR-UHFFFAOYSA-N 0.000 claims 1
QYTINMSJRAULJN-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-methylidenecyclopentane Chemical compound CC1(C)CCC(C)(C)C1=C QYTINMSJRAULJN-UHFFFAOYSA-N 0.000 claims 1
YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000001013 cariogenic effect Effects 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
125000004001 thioalkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
239000000243 solution Substances 0.000 description 82
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 71
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
239000011541 reaction mixture Substances 0.000 description 52
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
239000000203 mixture Substances 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 45
238000004809 thin layer chromatography Methods 0.000 description 42
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 36
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
229960000583 acetic acid Drugs 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
239000012362 glacial acetic acid Substances 0.000 description 22
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000012071 phase Substances 0.000 description 19
238000000746 purification Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000004108 freeze drying Methods 0.000 description 18
238000004817 gas chromatography Methods 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
239000011734 sodium Substances 0.000 description 17
239000000284 extract Substances 0.000 description 16
125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000004913 activation Effects 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
238000003756 stirring Methods 0.000 description 14
PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 13
235000015497 potassium bicarbonate Nutrition 0.000 description 13
229910000028 potassium bicarbonate Inorganic materials 0.000 description 13
239000011736 potassium bicarbonate Substances 0.000 description 13
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
150000002576 ketones Chemical class 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
229960005261 aspartic acid Drugs 0.000 description 8
239000010410 layer Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
WKVFTNSDTVNOED-UHFFFAOYSA-N 2,2,5,5-tetramethylcyclopentane-1-carbonyl chloride Chemical compound CC1(C)CCC(C)(C)C1C(Cl)=O WKVFTNSDTVNOED-UHFFFAOYSA-N 0.000 description 5
CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
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
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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 4
238000000354 decomposition reaction Methods 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 3
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 3
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 3
230000008034 disappearance Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000005187 foaming Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000012456 homogeneous solution Substances 0.000 description 3
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002324 mouth wash Substances 0.000 description 3
229940051866 mouthwash Drugs 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
235000015067 sauces Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000010792 warming Methods 0.000 description 3
UVPVYHMJHITAMD-SCZZXKLOSA-N (3s)-3-amino-4-[[(1r)-1-benzamidoethyl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C)NC(=O)C1=CC=CC=C1 UVPVYHMJHITAMD-SCZZXKLOSA-N 0.000 description 2
WCRSJPWATCOGRI-UHFFFAOYSA-N 1,2,2-trimethylcyclohexane-1-carbonyl chloride Chemical compound CC1(C)CCCCC1(C)C(Cl)=O WCRSJPWATCOGRI-UHFFFAOYSA-N 0.000 description 2
WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 2
IPDSFOCRHPZFFS-UHFFFAOYSA-N 2,2,4-trimethylpentanoyl chloride Chemical compound CC(C)CC(C)(C)C(Cl)=O IPDSFOCRHPZFFS-UHFFFAOYSA-N 0.000 description 2
BXYUQRQZHXARGL-UHFFFAOYSA-N 2,2,5,5-tetramethylcyclopentan-1-one Chemical compound CC1(C)CCC(C)(C)C1=O BXYUQRQZHXARGL-UHFFFAOYSA-N 0.000 description 2
BEGZZVINPDCXMZ-UHFFFAOYSA-N 2,5-dimethylcyclopentane-1,1-dicarboxylic acid Chemical compound CC1CCC(C)C1(C(O)=O)C(O)=O BEGZZVINPDCXMZ-UHFFFAOYSA-N 0.000 description 2
WOUFKYXLNUWBJY-UHFFFAOYSA-N 2-cyclopropylethenylcyclopropane Chemical group C1CC1C=CC1CC1 WOUFKYXLNUWBJY-UHFFFAOYSA-N 0.000 description 2
BLEFFJIHHNLKDC-UHFFFAOYSA-N 2-tert-butylcyclohexane-1-carbonyl chloride Chemical compound CC(C)(C)C1CCCCC1C(Cl)=O BLEFFJIHHNLKDC-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 2
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230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
DFTMVZIUYVECNW-VKHMYHEASA-N n-[(3s)-2,5-dioxooxolan-3-yl]formamide Chemical compound O=CN[C@H]1CC(=O)OC1=O DFTMVZIUYVECNW-VKHMYHEASA-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
238000006386 neutralization reaction Methods 0.000 description 1
RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000006798 recombination Effects 0.000 description 1
238000005215 recombination Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000000892 thaumatin Substances 0.000 description 1
235000010436 thaumatin Nutrition 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
235000014101 wine Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/10—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentane ring
- C07C13/11—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentane ring substituted by unsaturated hydrocarbon groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/395—Saturated compounds containing a keto group being part of a ring of a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/42—Acyl halides of acids containing three or more carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/44—Acyl halides containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/06—Saturated compounds having a carboxyl group bound to a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/04—Four-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Oral & Maxillofacial Surgery (AREA)
Birds (AREA)
Epidemiology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Seasonings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Confectionery (AREA)
Medicinal Preparation (AREA)
Cephalosporin Compounds (AREA)

DD84263717A 1983-06-13 1984-06-01 Verfahren zur herstellung von gem-diaminoal-kanderivaten DD223148A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/503,853 US4571345A (en)	1983-06-13	1983-06-13	1,1-Diaminoalkane derived sweeteners

Publications (1)

Publication Number	Publication Date
DD223148A5 true DD223148A5 (de)	1985-06-05

Family

ID=24003790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84263717A DD223148A5 (de)	1983-06-13	1984-06-01	Verfahren zur herstellung von gem-diaminoal-kanderivaten

Country Status (21)

Country	Link
US (1)	US4571345A (fr)
EP (2)	EP0242896A3 (fr)
JP (1)	JPS59231050A (fr)
KR (1)	KR910000406B1 (fr)
AT (1)	ATE47385T1 (fr)
AU (1)	AU567944B2 (fr)
CA (1)	CA1221683A (fr)
DD (1)	DD223148A5 (fr)
DE (1)	DE3480200D1 (fr)
DK (1)	DK287284A (fr)
ES (3)	ES8602596A1 (fr)
FI (1)	FI842356A7 (fr)
GR (1)	GR82143B (fr)
HU (1)	HU199393B (fr)
IL (1)	IL71447A (fr)
MX (1)	MX7621E (fr)
NO (1)	NO165491C (fr)
NZ (1)	NZ208075A (fr)
PT (1)	PT78712B (fr)
SU (1)	SU1494862A3 (fr)
ZA (1)	ZA843198B (fr)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4692512A (en) *	1984-07-13	1987-09-08	The Procter & Gamble Company	Alpha-L-aspartyl-D-phenylglycine esters and amides useful as high intensity sweeteners
US4654219A (en) *	1984-12-27	1987-03-31	General Foods Corporation	L-aminodicarboxylic-(O-cycloalkyl)-L-aminocarboxylate alkyl ester sweeteners
EP0196461A3 (fr) *	1985-03-01	1987-04-22	Kyowa Hakko Kogyo Co., Ltd.	Dérivés de cyclopentane
US4636396A (en) *	1985-04-15	1987-01-13	General Foods Corporation	Foodstuff with L-aminodicarboxylic acid gem-diamines
US4619782A (en) *	1985-04-15	1986-10-28	General Foods Corporation	L-aminodicarboxylic acid gem-diamines
US4666729A (en) *	1985-05-24	1987-05-19	General Foods Corporation	Sweetening with L-aminodicarboxylic acid amides of alkoxyalkylamines
US4654439A (en) *	1985-05-24	1987-03-31	General Foods Corporation	L-aminodicarboxylic acid amides of alkoxyalkylamines
US4692513A (en) *	1985-12-20	1987-09-08	The Procter & Gamble Company	Alpha-L-aspartyl-D-heteroaromatic-substituted glycine esters and amides useful as high intensity sweeteners
DE3617605A1 (de) *	1986-05-23	1987-11-26	Schering Ag	Verfahren zur herstellung von diaminoalkan-derivaten
FR2630304B1 (fr) *	1988-04-22	1990-08-31	Bernard Lyon I Universite Clau	Derives n-hydrocarbones des acides aspartique et glutamique alpha-monoamides utiles comme agents edulcorants
IT1228451B (it) *	1989-02-22	1991-06-19	Sclavo S P A Siena	Nuovi derivati diamminici geminali e loro impiego nelle sintesi di peptidi retro-inversi
WO1996028413A1 (fr) *	1995-03-16	1996-09-19	Hoechst Celanese Corporation	Synthese de derives d'acide amidocarboxyliques
AR046078A1 (es) *	2003-08-06	2005-11-23	Senomyx Inc	Nuevos sabores, modificadores de sabores, sustancias gustativas, mejoradores de gusto, sustancias gustativas y/o mejoradoras del gusto umani o dulce y uso de los mismos.
US8435587B2 (en) *	2005-11-23	2013-05-07	The Coca-Cola Company	High-potency sweetener composition with long-chain primary aliphatic saturated alcohol and compositions sweetened therewith
US8945652B2 (en) *	2005-11-23	2015-02-03	The Coca-Cola Company	High-potency sweetener for weight management and compositions sweetened therewith
US8940350B2 (en) *	2005-11-23	2015-01-27	The Coca-Cola Company	Cereal compositions comprising high-potency sweeteners
US20070116829A1 (en) *	2005-11-23	2007-05-24	The Coca-Cola Company	Pharmaceutical Composition with High-Potency Sweetener
US8377491B2 (en) *	2005-11-23	2013-02-19	The Coca-Cola Company	High-potency sweetener composition with vitamin and compositions sweetened therewith
US20070116800A1 (en) *	2005-11-23	2007-05-24	The Coca-Cola Company	Chewing Gum with High-Potency Sweetener
US9101160B2 (en) *	2005-11-23	2015-08-11	The Coca-Cola Company	Condiments with high-potency sweetener
US8367138B2 (en) *	2005-11-23	2013-02-05	The Coca-Cola Company	Dairy composition with high-potency sweetener
US8524303B2 (en) *	2005-11-23	2013-09-03	The Coca-Cola Company	High-potency sweetener composition with phytosterol and compositions sweetened therewith
US8524304B2 (en) *	2005-11-23	2013-09-03	The Coca-Cola Company	High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith
US20070116833A1 (en) *	2005-11-23	2007-05-24	The Coca-Cola Company	High-Potency Sweetener Composition with Calcium and Compositions Sweetened Therewith
US20070116839A1 (en) *	2005-11-23	2007-05-24	The Coca-Cola Company	High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith
US8512789B2 (en) *	2005-11-23	2013-08-20	The Coca-Cola Company	High-potency sweetener composition with dietary fiber and compositions sweetened therewith
EP1971228A1 (fr) *	2005-11-23	2008-09-24	The Coca-Cola Company	Compositions d'edulcorant naturel tres puissant avec profil temporel et/ou profil de gout ameliore, procedes de preparation et utilisations
US8940351B2 (en) *	2005-11-23	2015-01-27	The Coca-Cola Company	Baked goods comprising high-potency sweetener
US8435588B2 (en) *	2005-11-23	2013-05-07	The Coca-Cola Company	High-potency sweetener composition with an anti-inflammatory agent and compositions sweetened therewith
ES2640453T3 (es)	2006-04-21	2017-11-03	Senomyx, Inc.	Procesos para preparar composiciones saborizantes sólidas
US8017168B2 (en) *	2006-11-02	2011-09-13	The Coca-Cola Company	High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith
US7632792B2 (en) *	2007-11-16	2009-12-15	International Flavors & Fragrances Inc.	Methyl cyclohexane carboxylates and their use in perfume compositions

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3492131A (en) *	1966-04-18	1970-01-27	Searle & Co	Peptide sweetening agents
US4338346A (en) *	1978-12-21	1982-07-06	The Procter & Gamble Company	Non-nutritive sweetener
US4411925A (en) *	1980-01-21	1983-10-25	Pfizer Inc.	Branched amides of L-aspartyl-d-amino acid dipeptides
US4399163A (en) *	1980-11-05	1983-08-16	Pfizer Inc.	Branched amides of L-aspartyl-D-amino acid dipeptides
US4423029A (en) *	1981-06-25	1983-12-27	The Procter & Gamble Company	(S)-3-Amino-4-[(S,S)-1-(1-hydroxyethyl)alkyl amino]-4-oxo-butyric acid compounds suitable as non-nutritive sweetners

1983
- 1983-06-13 US US06/503,853 patent/US4571345A/en not_active Expired - Fee Related
1984
- 1984-04-05 IL IL71447A patent/IL71447A/xx unknown
- 1984-04-05 GR GR74320A patent/GR82143B/el unknown
- 1984-04-30 ZA ZA843198A patent/ZA843198B/xx unknown
- 1984-05-03 EP EP87200462A patent/EP0242896A3/fr not_active Withdrawn
- 1984-05-03 EP EP84302978A patent/EP0128654B1/fr not_active Expired
- 1984-05-03 AT AT84302978T patent/ATE47385T1/de not_active IP Right Cessation
- 1984-05-03 DE DE8484302978T patent/DE3480200D1/de not_active Expired
- 1984-05-07 NZ NZ208075A patent/NZ208075A/xx unknown
- 1984-05-29 KR KR1019840002963A patent/KR910000406B1/ko not_active Expired
- 1984-05-30 JP JP59108717A patent/JPS59231050A/ja active Pending
- 1984-06-01 DD DD84263717A patent/DD223148A5/de not_active IP Right Cessation
- 1984-06-04 CA CA000455761A patent/CA1221683A/fr not_active Expired
- 1984-06-05 AU AU29058/84A patent/AU567944B2/en not_active Ceased
- 1984-06-08 PT PT78712A patent/PT78712B/pt not_active IP Right Cessation
- 1984-06-11 FI FI842356A patent/FI842356A7/fi not_active Application Discontinuation
- 1984-06-11 SU SU843751077A patent/SU1494862A3/ru active
- 1984-06-12 NO NO842338A patent/NO165491C/no unknown
- 1984-06-12 HU HU842264A patent/HU199393B/hu not_active IP Right Cessation
- 1984-06-12 MX MX8411176U patent/MX7621E/es unknown
- 1984-06-12 DK DK287284A patent/DK287284A/da not_active Application Discontinuation
- 1984-06-13 ES ES533690A patent/ES8602596A1/es not_active Expired
1985
- 1985-07-16 ES ES545627A patent/ES8701714A1/es not_active Expired
1986
- 1986-02-27 ES ES552814A patent/ES8704879A1/es not_active Expired

Also Published As

Publication number	Publication date
AU567944B2 (en)	1987-12-10
DE3480200D1 (de)	1989-11-23
ES552814A0 (es)	1987-04-16
EP0242896A3 (fr)	1988-11-30
ATE47385T1 (de)	1989-11-15
NZ208075A (en)	1988-06-30
IL71447A0 (en)	1984-07-31
PT78712A (pt)	1985-01-01
CA1221683A (fr)	1987-05-12
EP0128654A2 (fr)	1984-12-19
SU1494862A3 (ru)	1989-07-15
GR82143B (fr)	1984-12-13
NO842338L (no)	1984-12-14
US4571345A (en)	1986-02-18
ES533690A0 (es)	1985-12-01
KR910000406B1 (ko)	1991-01-25
KR850002833A (ko)	1985-05-20
HUT34430A (en)	1985-03-28
EP0242896A2 (fr)	1987-10-28
NO165491C (no)	1991-02-20
AU2905884A (en)	1984-12-20
ZA843198B (en)	1984-11-28
HU199393B (en)	1990-02-28
FI842356A7 (fi)	1984-12-14
DK287284A (da)	1984-12-14
NO165491B (no)	1990-11-12
EP0128654B1 (fr)	1989-10-18
IL71447A (en)	1988-01-31
EP0128654A3 (en)	1985-05-29
ES8704879A1 (es)	1987-04-16
ES8602596A1 (es)	1985-12-01
ES545627A0 (es)	1986-12-01
JPS59231050A (ja)	1984-12-25
ES8701714A1 (es)	1986-12-01
DK287284D0 (da)	1984-06-12
MX7621E (es)	1990-03-27
PT78712B (en)	1986-07-15
FI842356A0 (fi)	1984-06-11

Legal Events

Date	Code	Title	Description
2001-01-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD223148A5 (de)	1985-06-05	Verfahren zur herstellung von gem-diaminoal-kanderivaten
DE69303032T2 (de)	1996-10-02	Als süsstoffe brauchbare verbindungen und hir herstellungsverfahren
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