CA1241016A - Methode pour l'obtention de derives de substitution nucleaire de l'acide cinnamoylanthranilique - Google Patents

Methode pour l'obtention de derives de substitution nucleaire de l'acide cinnamoylanthranilique

Info

Publication number: CA1241016A
Authority: CA; Canada
Prior art keywords: hydroxy; acid; accordance; cyclic amine; nuclear substituted
Prior art date: 1984-09-25
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

CA000478780A

Other languages

English (en)

Inventor

Kinji Iizuka

Tetsuhide Kamijo

Ryoji Yamamoto

Hiromu Harada

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.)

Kissei Pharmaceutical Co Ltd

Original Assignee

Kissei Pharmaceutical Co Ltd

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.)

1984-09-25

Filing date

1985-04-10

Publication date

1988-08-23

1984-09-25 Priority claimed from US06/654,231 external-priority patent/US4587356A/en

1985-04-10 Application filed by Kissei Pharmaceutical Co Ltd filed Critical Kissei Pharmaceutical Co Ltd

1988-08-23 Application granted granted Critical

1988-08-23 Publication of CA1241016A publication Critical patent/CA1241016A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 45
GMEKUFJCKPYDAH-UHFFFAOYSA-N 2-(3-phenylprop-2-enoylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NC(=O)C=CC1=CC=CC=C1 GMEKUFJCKPYDAH-UHFFFAOYSA-N 0.000 title claims abstract description 15
238000004519 manufacturing process Methods 0.000 title claims abstract description 10
-1 cyclic amine Chemical class 0.000 claims abstract description 28
LZEMYXZYMHWMMN-UHFFFAOYSA-N 2-(phenylcarbamoyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)C(=O)NC1=CC=CC=C1 LZEMYXZYMHWMMN-UHFFFAOYSA-N 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 14
150000003935 benzaldehydes Chemical class 0.000 claims abstract description 9
239000002244 precipitate Substances 0.000 claims abstract description 7
239000000376 reactant Substances 0.000 claims abstract description 7
239000012445 acidic reagent Substances 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
239000000047 product Substances 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical group COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 10
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
FSKJPXSYWQUVGO-UHFFFAOYSA-N 2-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoylamino]benzoic acid Chemical group C1=C(O)C(OC)=CC(C=CC(=O)NC=2C(=CC=CC=2)C(O)=O)=C1 FSKJPXSYWQUVGO-UHFFFAOYSA-N 0.000 claims description 5
DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
AVHHJLURQYHHDR-UHFFFAOYSA-N 2-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoylamino]benzoic acid Chemical group C1=C(O)C(OC)=CC=C1C=CC(=O)NC1=CC=CC=C1C(O)=O AVHHJLURQYHHDR-UHFFFAOYSA-N 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
MWOOGOJBHIARFG-OUBTZVSYSA-N 4-hydroxy-3-methoxybenzaldehyde Chemical group [13CH3]OC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-OUBTZVSYSA-N 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
239000012442 inert solvent Substances 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000543 intermediate Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000243 solution Substances 0.000 description 7
239000013078 crystal Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 4
206010012438 Dermatitis atopic Diseases 0.000 description 4
208000024780 Urticaria Diseases 0.000 description 4
230000003266 anti-allergic effect Effects 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
201000008937 atopic dermatitis Diseases 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000004566 IR spectroscopy Methods 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000007815 allergy Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NZHGWWWHIYHZNX-UHFFFAOYSA-N 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-UHFFFAOYSA-N 0.000 description 1
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
GRIWJVSWLJHHEM-UHFFFAOYSA-N 3-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=C(O)C=CC=C1C=O GRIWJVSWLJHHEM-UHFFFAOYSA-N 0.000 description 1
HXLDCOVUIPCODC-UHFFFAOYSA-N 3-hydroxy-2-methoxybenzaldehyde;3-hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1O.COC1=C(O)C=CC=C1C=O HXLDCOVUIPCODC-UHFFFAOYSA-N 0.000 description 1
PMCWOGATSZLJKS-UHFFFAOYSA-N 3-hydroxy-4-propoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C=C1O PMCWOGATSZLJKS-UHFFFAOYSA-N 0.000 description 1
JUUPYFMXANQBND-UHFFFAOYSA-N 3-phenylprop-2-enoyl 2-aminobenzoate Chemical class NC1=CC=CC=C1C(=O)OC(=O)C=CC1=CC=CC=C1 JUUPYFMXANQBND-UHFFFAOYSA-N 0.000 description 1
QKMNBOPIPCIBFG-UHFFFAOYSA-N 4-[3-(2-carboxyanilino)-3-oxoprop-1-enyl]-2-methoxyphenolate;pyrrolidin-1-ium Chemical compound C1CC[NH2+]C1.C1=C([O-])C(OC)=CC(C=CC(=O)NC=2C(=CC=CC=2)C(O)=O)=C1 QKMNBOPIPCIBFG-UHFFFAOYSA-N 0.000 description 1
CBKYEFKMNADVGO-UHFFFAOYSA-N 4-hydroxy-3-propoxybenzaldehyde Chemical compound CCCOC1=CC(C=O)=CC=C1O CBKYEFKMNADVGO-UHFFFAOYSA-N 0.000 description 1
ZBURODYGHXGIML-UHFFFAOYSA-N 5-[3-(2-carboxyanilino)-3-oxoprop-1-enyl]-2-methoxyphenolate;pyrrolidin-1-ium Chemical compound C1CC[NH2+]C1.C1=C([O-])C(OC)=CC=C1C=CC(=O)NC1=CC=CC=C1C(O)=O ZBURODYGHXGIML-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000478780A 1984-09-25 1985-04-10 Methode pour l'obtention de derives de substitution nucleaire de l'acide cinnamoylanthranilique Expired CA1241016A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/654,231 US4587356A (en)	1981-09-01	1984-09-25	Process for the production of nuclear substituted cinnamoylanthranilic acid derivatives
US654,231		1984-09-25

Publications (1)

Publication Number	Publication Date
CA1241016A true CA1241016A (fr)	1988-08-23

Family

ID=24624008

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000478780A Expired CA1241016A (fr)	1984-09-25	1985-04-10	Methode pour l'obtention de derives de substitution nucleaire de l'acide cinnamoylanthranilique

Country Status (1)

Country	Link
CA (1)	CA1241016A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008144933A1 (fr) *	2007-05-29	2008-12-04	Université de Montréal	Inhibiteurs à base de cinnamoyle de la transglutaminase

1985
- 1985-04-10 CA CA000478780A patent/CA1241016A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008144933A1 (fr) *	2007-05-29	2008-12-04	Université de Montréal	Inhibiteurs à base de cinnamoyle de la transglutaminase
US8614233B2 (en)	2007-05-29	2013-12-24	Universite De Montreal	Cinnamoyl inhibitors of transglutaminase
US9162991B2 (en)	2007-05-29	2015-10-20	University Of Ottawa	Cinnamoyl inhibitors of transglutaminase

Legal Events

Date	Code	Title	Description
2005-08-23	MKEX	Expiry

Publication	Publication Date	Title
US4486597A (en)	1984-12-04	Method for the production of nuclear substituted cinnamoylanthranilic acid derivatives
US4587356A (en)	1986-05-06	Process for the production of nuclear substituted cinnamoylanthranilic acid derivatives
US5239077A (en)	1993-08-24	Highly pure amidoximes
CA1241016A (fr)	1988-08-23	Methode pour l'obtention de derives de substitution nucleaire de l'acide cinnamoylanthranilique
JPH0458468B2 (fr)	1992-09-17
US4665197A (en)	1987-05-12	Process for preparing azetidine derivatives and intermediates thereof
Jagdmann Jr et al.	1990	A mild efficient procedure for the conversion of carboxylic acid esters to primary amides using formamide/methanolic sodium methoxide
JPH0782268A (ja)	1995-03-28	ベンゾチアジアゾール誘導体の製法
CN115286568B (zh)	2023-12-12	一种2-羟基-4-三氟甲基吡啶的制备方法
JP2782698B2 (ja)	1998-08-06	９−アミノ−１，２，３，４−テトラヒドロアクリジンの新規製造方法
CA1050988A (fr)	1979-03-20	Benzoylpyridines et derives
US3019227A (en)	1962-01-30	Alkyl acridines
Burger et al.	1950	Amino Derivatives of 2, 2-Diphenylcyclohexanone. I1
KR880000763B1 (ko)	1988-05-06	핵(核)치환 신나모일 아미노 안트라닐산 유도체의 제조방법
CA2040110A1 (fr)	1991-10-11	Procede de preparation de derives de pyridine et de quinoleine
JPS6119624B2 (fr)	1986-05-17
JP3563424B2 (ja)	2004-09-08	４ｈ−ピラン−４−オンの製造方法
SU959622A3 (ru)	1982-09-15	Способ получени производных бензоциклогептена или их солей
Papadopoulos et al.	1994	Reactions of lucigenin in protic solvents in the presence of amines
US4948912A (en)	1990-08-14	Alkylating agents and method of use thereof
US3347864A (en)	1967-10-17	Production of aminoquinolines
JP4287083B2 (ja)	2009-07-01	２−または４−モノ置換ピリジンの製造方法並びに４−モノ置換ピリジンまたはその塩の選択的製造方法および分離方法
CN113121418A (zh)	2021-07-16	一种1,4-二氢吡啶-3,5-二甲酰胺类化合物的制备方法
SU346867A1 (ru)		Способ получения производных бензоморфана
JPS6054342A (ja)	1985-03-28	バニリルアミン塩酸塩の製造方法