CA1071460A - Produit contrant les effets de la methylxanthine - Google Patents

Produit contrant les effets de la methylxanthine

Info

Publication number: CA1071460A
Authority: CA; Canada
Prior art keywords: coffee; caffeine; present; nicotinic acid; amount
Prior art date: 1976-03-23
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.): Expired

Application number

CA271,766A

Other languages

English (en)

Inventor

Harold S. Levenson

Alan B. Pritchard

Benjamin R. Zeitlin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

General Foods Corp

Original Assignee

General Foods 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.)

1976-03-23

Filing date

1977-02-14

Publication date

1980-02-12

1976-03-23 Priority claimed from US05/669,573 external-priority patent/US4076856A/en

1977-02-14 Application filed by General Foods Corp filed Critical General Foods Corp

1980-02-12 Application granted granted Critical

1980-02-12 Publication of CA1071460A publication Critical patent/CA1071460A/fr

Status Expired legal-status Critical Current

Links

230000008485 antagonism Effects 0.000 title abstract description 9
PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 title description 11
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims abstract description 86
235000013353 coffee beverage Nutrition 0.000 claims abstract description 70
235000016213 coffee Nutrition 0.000 claims abstract description 58
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims abstract description 44
229960001948 caffeine Drugs 0.000 claims abstract description 43
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims abstract description 43
239000005557 antagonist Substances 0.000 claims abstract description 34
239000000203 mixture Substances 0.000 claims abstract description 23
239000000463 material Substances 0.000 claims abstract description 8
230000000694 effects Effects 0.000 claims abstract description 6
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 64
235000001968 nicotinic acid Nutrition 0.000 claims description 32
239000011664 nicotinic acid Substances 0.000 claims description 32
229960003512 nicotinic acid Drugs 0.000 claims description 32
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 28
235000005152 nicotinamide Nutrition 0.000 claims description 14
239000011570 nicotinamide Substances 0.000 claims description 14
229960003966 nicotinamide Drugs 0.000 claims description 14
239000007787 solid Substances 0.000 claims description 14
235000021539 instant coffee Nutrition 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 3
RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 abstract description 18
238000000034 method Methods 0.000 abstract description 16
230000004936 stimulating effect Effects 0.000 abstract description 15
230000001627 detrimental effect Effects 0.000 abstract description 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 abstract 2
229940075420 xanthine Drugs 0.000 abstract 1
240000007154 Coffea arabica Species 0.000 description 44
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
241001122767 Theaceae Species 0.000 description 18
239000000284 extract Substances 0.000 description 15
235000013361 beverage Nutrition 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
244000046052 Phaseolus vulgaris Species 0.000 description 10
235000010627 Phaseolus vulgaris Nutrition 0.000 description 10
244000299461 Theobroma cacao Species 0.000 description 10
150000003222 pyridines Chemical class 0.000 description 7
-1 theophylline Chemical class 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WWNNZCOKKKDOPX-UHFFFAOYSA-N N-methylnicotinate Chemical compound C[N+]1=CC=CC(C([O-])=O)=C1 WWNNZCOKKKDOPX-UHFFFAOYSA-N 0.000 description 6
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 6
235000009470 Theobroma cacao Nutrition 0.000 description 5
235000019219 chocolate Nutrition 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
235000013305 food Nutrition 0.000 description 5
239000000243 solution Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
241000533293 Sesbania emerus Species 0.000 description 4
239000002253 acid Substances 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 3
230000028527 righting reflex Effects 0.000 description 3
239000007921 spray Substances 0.000 description 3
229960004559 theobromine Drugs 0.000 description 3
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
235000002187 Coffea robusta Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
241000699670 Mus sp. Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000003292 diminished effect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
238000005325 percolation Methods 0.000 description 2
235000008160 pyridoxine Nutrition 0.000 description 2
239000011677 pyridoxine Substances 0.000 description 2
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
230000001629 suppression Effects 0.000 description 2
229960000278 theophylline Drugs 0.000 description 2
229940011671 vitamin b6 Drugs 0.000 description 2
YCABHAGDPZAUBJ-UHFFFAOYSA-N 1-methyl-2h-pyridine-3-carboxylic acid Chemical compound CN1CC(C(O)=O)=CC=C1 YCABHAGDPZAUBJ-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000010340 Sleep Deprivation Diseases 0.000 description 1
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 description 1
229930006000 Sucrose Natural products 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
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 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
230000003467 diminishing effect Effects 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000021564 flavored carbonated beverage Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000020278 hot chocolate Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000009533 lab test Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
208000022925 sleep disturbance Diseases 0.000 description 1
230000004622 sleep time Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000013616 tea Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA271,766A 1976-03-23 1977-02-14 Produit contrant les effets de la methylxanthine Expired CA1071460A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/669,573 US4076856A (en)	1974-01-09	1976-03-23	Methyl xanthine antagonism

Publications (1)

Publication Number	Publication Date
CA1071460A true CA1071460A (fr)	1980-02-12

Family

ID=24686861

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA271,766A Expired CA1071460A (fr)	1976-03-23	1977-02-14	Produit contrant les effets de la methylxanthine

Country Status (1)

Country	Link
CA (1)	CA1071460A (fr)

1977
- 1977-02-14 CA CA271,766A patent/CA1071460A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-02-12	MKEX	Expiry

Publication	Publication Date	Title
US4076856A (en)	1978-02-28	Methyl xanthine antagonism
US8524307B2 (en)	2013-09-03	Healthy coffee and methods of its production
WO2010124936A1 (fr)	2010-11-04	Composition de boisson ou d'aliments comprenant des solides de café non torréfié
JPH11510703A (ja)	1999-09-21	望ましい浸出酸味を伴う、浸出力の増強されたよりダークなカップカラーを提供する急速ローストコーヒー
US2380092A (en)	1945-07-10	Coffee product
US11547123B2 (en)	2023-01-10	Methods for reducing negative flavor attributes in coffee and compositions therefrom
US3840684A (en)	1974-10-08	Decaffeinated coffee
ES481761A1 (es)	1980-01-16	Un metodo para preparar una mezcla seca de cafe instantaneo similar al cafe.
Morales	1989	Effect of holding-time on sensory quality of brewed coffee
CA1043156A (fr)	1978-11-28	Antagoniste de la methylxanthine
JPH0145344B2 (fr)	1989-10-03
KR19990080746A (ko)	1999-11-15	커피 대용차의 제조 방법
TW201907809A (zh)	2019-03-01	容器裝咖啡飲料、咖啡感改善劑、及改善咖啡感之方法
US6235317B1 (en)	2001-05-22	Additive for stimulants
JPH046328B2 (fr)	1992-02-05
US3829588A (en)	1974-08-13	Dipeptide low-grade coffees
DE2612782A1 (de)	1977-09-29	Verwendung von pyridin-antagonisten fuer methylxanthine zur herabsetzung ihrer stimulierenden wirkung in lebensmittelzubereitungen
JP7564934B1 (ja)	2024-10-09	抽出用コーヒー組成物及びその製造方法ならびにコーヒー飲料の製造方法
NO761090L (no)	1977-09-30	Kaffein-antagonister.
JP3486129B2 (ja)	2004-01-13	コーヒー抽出液
JPS609774B2 (ja)	1985-03-13	コ−ヒ−製品の苦味抑制法
JPS6283847A (ja)	1987-04-17	健康茶
WO1998007330A1 (fr)	1998-02-26	Cafe enrichi de cafeine, cafe recafeine, et procedes utiles a leur fabrication
DK404689A (da)	1991-02-18	Pulver til fremstilling af en kaffelignende drik
JPS5932096B2 (ja)	1984-08-06	コ−ヒ−又は茶の香味成分の抽出法