KR850002833A - 젬-디아미노알칸 유도체 감미료 - Google Patents
젬-디아미노알칸 유도체 감미료 Download PDFInfo
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- KR850002833A KR850002833A KR1019840002963A KR840002963A KR850002833A KR 850002833 A KR850002833 A KR 850002833A KR 1019840002963 A KR1019840002963 A KR 1019840002963A KR 840002963 A KR840002963 A KR 840002963A KR 850002833 A KR850002833 A KR 850002833A
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- 235000003599 food sweetener Nutrition 0.000 title claims 3
- 239000003765 sweetening agent Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- -1 dicycloalkyl Chemical group 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000004001 thioalkyl group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000005592 polycycloalkyl group Polymers 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 230000002708 enhancing effect Effects 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000006242 amine protecting group Chemical group 0.000 claims 2
- 150000003862 amino acid derivatives Chemical class 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 2
- 150000003140 primary amides Chemical class 0.000 claims 2
- 238000006276 transfer reaction Methods 0.000 claims 2
- HCLUEAXWFVFZEA-UHFFFAOYSA-N (2,2,5,5-tetramethylcyclopentyl)methanol Chemical compound CC1(C)CCC(C)(C)C1CO HCLUEAXWFVFZEA-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
- 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 1
- BXYUQRQZHXARGL-UHFFFAOYSA-N 2,2,5,5-tetramethylcyclopentan-1-one Chemical compound CC1(C)CCC(C)(C)C1=O BXYUQRQZHXARGL-UHFFFAOYSA-N 0.000 claims 1
- YQWKTQMDNDIFTP-UHFFFAOYSA-N 2,2,5,5-tetramethylcyclopentane-1-carboxylic acid Chemical compound CC1(C)CCC(C)(C)C1C(O)=O YQWKTQMDNDIFTP-UHFFFAOYSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 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 1
- 150000001412 amines Chemical class 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical class OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 150000001509 aspartic acid derivatives Chemical class 0.000 claims 1
- 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 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006243 carbonyl protecting group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 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 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (32)
- 다음 일반식의 화합물:여기서 n은 0 또는 1이고, R은 저알킬, 저히드록시알킬 또는 저티오알킬이여, R´는 수소 또는 저알킬이고, R˝는 3-10 탄소원자의 분기알킬, 3-7 탄소원자의 시클로알킬, 1-5 저알킬기로 치환된 시클로알킬, 저알킬-시클로알킬, 디시클로알킬, 헤테로원자가 산소, 질소 또는 황이고 시클로알킬기는 4-7 탄소 원자의 것인 헤테로시클로알킬, 저알킬치환헤테로시클로알킬, 용융폴리시클로알킬, 페닐 또는 저알킬치환 페닐이다.
- 제1항에 있어서, 용융폴리시클로알킬은 노르보닐, 휀칠, 1-아다맨틸 또는 2-아다맨틸인 상기 화합물.
- 제1항에 있어서, 시클로알킬은 5-6 탄소원자인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 시클로펜틸인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 트리메틸 아세틸인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 노르보닐인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 2-메틸시클로헥실인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 디시클로프로필메틸인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 디메틸시클로펜틸인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 테트라메틸 시클로펜틸인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 디메틸시클로헤실인 상기 화합물.
- 제1항에 있어서, n=1, R은 메틸, R´는 수소 그리고 R˝는 t-부틸시클로헥실인 상기 화합물.
- 제1항에 있어서, n=1, R은 히드록시메틸, R´는 수소 그리고 R˝는 테트라메틸 시클로펜틸인 상기 화합물.
- 제1항에 있어서, n=1, R과 R´는 메틸 그리고 R˝는 시클로펜틸인 상기 화합물.
- 제1항의 화합물 유효량과 비독성담체로 이루어지는 것을 특징으로 하는 식용감미물질 조성물.
- 제1항의 화합물 유효량과 식용물질로 이루어지는 것을 특징으로 하는 식용감미 조성물.
- 제1항의 화합물 향증진 유효량과 비독성담체로 이루어지는 것을 특징으로 하는 식용물질의 향 증진 조성물.
- 제1항의 화합물 향증진 유효량과 식용물질로 이루어지는 것을 특징으로 하는 향증진식용조성물.
- 제1항의 화합물 향증진 유효 감미량을 식용물질에 첨가하는 것으로 이루어지는 식용물질 감미방법.
- 제1항의 화합물 향증진유효량을 식용물질에 첨가하는 것으로 이루어지는 식용물질의 향증진방법.
- 다음 일반식의 보호아미노산을,(여기서 n은 1 또는 2, X는 아민보호기 그리고 Y는 카르보닐 보호기이다)다음 일반식의 아미노산 유도체,(여기서 R은 저알킬, 저히드록시알킬 또는 저티오알킬이고 R´는 수소 또는 저알킬이며 Z는 수소 또는 카르복실 보호기이다)와 반응시켜 다음 일반식의 화합물을 생성하는 단계와, 보호기 Z를, 그것이 수소가 아닌 경우에는, 제거하여 다음 일반식의 화합물을 생성하는 단계와, 그리고 이 화합물을 다음 일반식의 해당하는 모노아실레이트젬-디아미노 알칸염(여기서 R, R´, n, X 및 Y는 상기와 같은 정의를 가지며 A는 음이온이다)으로 전환시키는 단계, 그리고 이 화합물을 일반식 R˝COC1의 화합물(여기서 R˝는 상기와 같은 정의를 갖는다)의 산염화물과 반응시켜서 다음 일반식의 해당하는 보호된 감미료 유도체를 생성하는 단계와, 보호기 X와 Y를 제거하는 단계로 이루어지는 다음 일반식의 화합물을 제조하는 방법.여기서 n은 0 또는 1이고, R은 저알킬, 저히드록시알킬 또는 저티오알킬이며, R´는 수소 또는 저알킬이고, R˝는 3-10 탄소원자의 분기알킬, 3-7 탄소원자의 시클로 알킬, 1-5 저알킬기로 치환된 시클로알킬, 저알킬-시클로알킬, 디시클로알킬, 헤테로원자가 산소, 질소 또는 황이고 시클로알킬기가 4-7 탄소원자의 것인 헤테로 시클로알킬, 저알킬-치환헤테로 시클로알킬, 용융폴리시클로알킬, 페닐 또는 저알킬-치환페닐이다.
- 제21항에 있어서, 카르복실산 유도체의 모노아실레이트 젬-디아미노알칸염으로의 전환은 커티우스(Curtius)전이 반응에 의하여 실행되는 것을 특징으로 하는 상기 화합물의 제조방법.
- 제21항에 있어서, 카르복실산 유도체의 모노아실레이트 젬-디아미노알칸염으로의 전환은 슈미트(Schmidt)전이반응에 의하여 달성되는 것을 특징으로 하는 상기 화합물의 제조방법.
- 제21항에 있어서, 카르복실산 유도체의 모노아실레이트 젬-디아미노알칸염으로의 전환은 처음에 카르복실산 유도체를 암모니아와의 축합반응에 의하여 해당하는 아미드로 전환시키고 다음에 아미드를 호프만(Hofmann)전이 반응에 의하여 젬-디아미노 알칸염으로 전한시킴으로써 실행되는 것을 특징으로 하는 상기 화합물의 제조방법.
- 다음 일반식의 아미노산 유도체(여기서 R은 저알킬, 저히드록시알킬 또는 저 티오-알킬이고 R´는 수소 또는 저알킬이며 Z는 카르복실 보호기이다)를 일반식 R˝COC1의 산염화물(R˝는 상기와 같은 정의를 갖는다)과 반응시켜 다음 일반식의 해당화합물를 생성하는 단계와, 보호기 Z를 제거시켜 다음 일반식의 해당하는 아실레이트 아미노산 유도체를 생성하는 단계, 이 화합물을 다음 일반식의 1차 아미드 유도체로 전환시키는 단계, 이와 같이 얻은 1차 아미드유도체를 전이 반응시켜 다음 일반식의 화합물(여기서 A는 음이온이다)을 생성하는 단계, 그리고 이와 같이 얻은 전이반응된 화합물을 다음 일반식의 브호된 아미노말론사 또는 아스파르트산 유도체(여기서 X는 아민 보호기이고, Y는 카르복실 보호기 그리고 n은 1 또는 2이다)와 축합반응시켜 다음 일반식의 X와 Y에 의하여 보호된 아민과 카르복실기를 갖는 해당하는 젬-디아미노알칸을 생성하는 단계, 그리고 보호기 X와 Y를 제거하는 단계로 이루어지는 다음 일반식의 화합물을 제조하는 방법여기서 n은 0 또는 1, R은 저알킬, 저히드록시 알킬 또는 저티오-알킬, R´는 수소 또는 저알킬, 그리고 R˝는 3-10 탄소원자인 분기알킬, 3-7 탄소원자인 시클로알킬, 1-5 저알킬기로 치환된 시클로알킬, 저알킬-시클로알킬, 디시클로알킬, 헤테로원자가 산소, 질소 또는 황이고 시클로알킬기가 4-7 탄소원자의 것인 헤테로시클로알킬, 저알킬-치환헤테로시클로알킬, 용융폴리시클로알킬, 페닐 또는 저알킬-치환페닐이다.
- 제25항에 있어서, 다음 일반식의 아민염이 다음 일반식의 아미노말론산 또는 아스파르트산의 환산유도체(여기서 W는 산소 또는 황이다)와 함께 최종 일반식의 해당 화합물을 형성하는 것을 특징으로 하는 상기 화합물의 제조방법.
- 화합물 2,2,5,5-테트라메틸시클로펜탄온.
- 화합물 1,2,2,5,5-펜타메틸시클로펜탄올.
- 화합물 1-메틸렌-2,2,5,5-테트라메틸시클로펜탄.
- 화합물 2,2,5,5-테트라메틸시클로펜틸메탄올.
- 화합물 2,2,5,5-테트라메틸시클로펜탄카르복실산.
- 제1항에 있어서, 생리적으로 허용되는 양이온 및 산 첨가염.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/503,853 US4571345A (en) | 1983-06-13 | 1983-06-13 | 1,1-Diaminoalkane derived sweeteners |
US503853 | 1983-06-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850002833A true KR850002833A (ko) | 1985-05-20 |
KR910000406B1 KR910000406B1 (ko) | 1991-01-25 |
Family
ID=24003790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840002963A KR910000406B1 (ko) | 1983-06-13 | 1984-05-29 | 젬-디아미노알칸 유도체 감미료 |
Country Status (21)
Country | Link |
---|---|
US (1) | US4571345A (ko) |
EP (2) | EP0242896A3 (ko) |
JP (1) | JPS59231050A (ko) |
KR (1) | KR910000406B1 (ko) |
AT (1) | ATE47385T1 (ko) |
AU (1) | AU567944B2 (ko) |
CA (1) | CA1221683A (ko) |
DD (1) | DD223148A5 (ko) |
DE (1) | DE3480200D1 (ko) |
DK (1) | DK287284A (ko) |
ES (3) | ES8602596A1 (ko) |
FI (1) | FI842356A (ko) |
GR (1) | GR82143B (ko) |
HU (1) | HU199393B (ko) |
IL (1) | IL71447A (ko) |
MX (1) | MX7621E (ko) |
NO (1) | NO165491C (ko) |
NZ (1) | NZ208075A (ko) |
PT (1) | PT78712B (ko) |
SU (1) | SU1494862A3 (ko) |
ZA (1) | ZA843198B (ko) |
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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 (en) * | 1985-03-01 | 1987-04-22 | Kyowa Hakko Kogyo Co., Ltd. | Cyclopentane derivatives |
US4619782A (en) * | 1985-04-15 | 1986-10-28 | General Foods Corporation | L-aminodicarboxylic acid gem-diamines |
US4636396A (en) * | 1985-04-15 | 1987-01-13 | General Foods Corporation | Foodstuff with 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 |
IL80577A0 (en) * | 1985-11-27 | 1987-02-27 | Schering Ag | Process for the preparation of cyclopentanecarboxylic acid derivatives |
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 (en) * | 1995-03-16 | 1996-09-19 | Hoechst Celanese Corporation | Synthesis of amidocarboxylic acid derivatives |
NZ545747A (en) * | 2003-08-06 | 2010-06-25 | Senomyx Inc | T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds |
US9101160B2 (en) * | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
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 |
US8945652B2 (en) * | 2005-11-23 | 2015-02-03 | The Coca-Cola Company | High-potency sweetener for weight management and compositions sweetened therewith |
US8377491B2 (en) * | 2005-11-23 | 2013-02-19 | The Coca-Cola Company | High-potency sweetener composition with vitamin 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 |
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 |
US20070116800A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Chewing Gum with 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 |
US8367138B2 (en) * | 2005-11-23 | 2013-02-05 | The Coca-Cola Company | Dairy composition with high-potency sweetener |
EP1971228A1 (en) * | 2005-11-23 | 2008-09-24 | The Coca-Cola Company | Natural high-potency sweetener compositions with improved temporal profile and/or flavor profile, methods for their formulation, and uses |
US8940351B2 (en) * | 2005-11-23 | 2015-01-27 | The Coca-Cola Company | Baked goods comprising high-potency sweetener |
US20070116833A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition with Calcium and Compositions Sweetened Therewith |
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 |
US8512789B2 (en) * | 2005-11-23 | 2013-08-20 | The Coca-Cola Company | High-potency sweetener composition with dietary fiber and compositions sweetened therewith |
KR101387563B1 (ko) | 2006-04-21 | 2014-04-25 | 세노믹스, 인코포레이티드 | 고효능의 조미용 향료를 포함하는 식품 조성물 및 이의 제조 방법 |
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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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/en not_active Withdrawn
- 1984-05-03 AT AT84302978T patent/ATE47385T1/de not_active IP Right Cessation
- 1984-05-03 DE DE8484302978T patent/DE3480200D1/de not_active Expired
- 1984-05-03 EP EP84302978A patent/EP0128654B1/en not_active Expired
- 1984-05-07 NZ NZ208075A patent/NZ208075A/xx unknown
- 1984-05-29 KR KR1019840002963A patent/KR910000406B1/ko active IP Right Grant
- 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/en 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/FI842356A/fi not_active Application Discontinuation
- 1984-06-11 SU SU843751077A patent/SU1494862A3/ru active
- 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 NO NO842338A patent/NO165491C/no 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
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