CA1042915A - 2-iminomethyl-3',4',5'-trimethoxycinnamic acids and esters thereof, and their production - Google Patents

2-iminomethyl-3',4',5'-trimethoxycinnamic acids and esters thereof, and their production

Info

Publication number: CA1042915A
Authority: CA; Canada
Prior art keywords: formula; grams; iminomethyl; trimethoxycinnamic; production
Prior art date: 1973-09-10
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

CA208,720A

Other languages

English (en)

French (fr)

Other versions

CA208720S (en

Inventor

Borge Alhede

Niels Gelting

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.)

Sandoz AS

Original Assignee

Gea AS

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.)

1973-09-10

Filing date

1974-09-09

Publication date

1978-11-21

1974-09-09 Application filed by Gea AS filed Critical Gea AS

1978-11-21 Application granted granted Critical

1978-11-21 Publication of CA1042915A publication Critical patent/CA1042915A/en

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title claims description 9
239000002253 acid Substances 0.000 title abstract description 5
150000007513 acids Chemical class 0.000 title abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
JFRKQRNPLPJBQG-UHFFFAOYSA-N 2-cyano-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=C(C#N)C(O)=O)=CC(OC)=C1OC JFRKQRNPLPJBQG-UHFFFAOYSA-N 0.000 claims abstract description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims abstract description 4
230000007935 neutral effect Effects 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 6
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
150000001875 compounds Chemical class 0.000 description 18
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 9
229960001082 trimethoprim Drugs 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
229960004198 guanidine Drugs 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
NENLHUFWWOXTFW-IZZDOVSWSA-N ethyl (e)-2-cyano-3-(3,4,5-trimethoxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C(\C#N)=C\C1=CC(OC)=C(OC)C(OC)=C1 NENLHUFWWOXTFW-IZZDOVSWSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
-1 2,4-diamino-6-hydrazino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine Chemical compound 0.000 description 1
FYJKTYLNKCUCLP-UHFFFAOYSA-N 6-hydroxytrimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2N)O)=C1 FYJKTYLNKCUCLP-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
DGXQTDZFHRFSQP-UHFFFAOYSA-N ethyl 2-cyano-3-(3,4,5-trimethoxyphenyl)propanoate Chemical compound CCOC(=O)C(C#N)CC1=CC(OC)=C(OC)C(OC)=C1 DGXQTDZFHRFSQP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA208,720A 1973-09-10 1974-09-09 2-iminomethyl-3',4',5'-trimethoxycinnamic acids and esters thereof, and their production Expired CA1042915A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK495973A DK495973A (de)	1973-09-10	1973-09-10

Publications (1)

Publication Number	Publication Date
CA1042915A true CA1042915A (en)	1978-11-21

Family

ID=8138193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA208,720A Expired CA1042915A (en)	1973-09-10	1974-09-09	2-iminomethyl-3',4',5'-trimethoxycinnamic acids and esters thereof, and their production

Country Status (9)

Country	Link
JP (1)	JPS5076042A (de)
AT (1)	AT336581B (de)
CA (1)	CA1042915A (de)
DE (1)	DE2443079A1 (de)
DK (1)	DK495973A (de)
GB (1)	GB1442477A (de)
HK (1)	HK12478A (de)
KE (1)	KE2806A (de)
NL (1)	NL7411932A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4918716B2 (ja) *	2005-08-03	2012-04-18	セイコーインスツル株式会社	水素発生設備及び燃料電池システム

1973
- 1973-09-10 DK DK495973A patent/DK495973A/da not_active Application Discontinuation
1974
- 1974-09-06 GB GB3898374A patent/GB1442477A/en not_active Expired
- 1974-09-09 CA CA208,720A patent/CA1042915A/en not_active Expired
- 1974-09-09 NL NL7411932A patent/NL7411932A/xx not_active Application Discontinuation
- 1974-09-09 JP JP10307774A patent/JPS5076042A/ja active Pending
- 1974-09-09 AT AT724374A patent/AT336581B/de active
- 1974-09-09 DE DE19742443079 patent/DE2443079A1/de not_active Withdrawn
1977
- 1977-11-29 KE KE280677A patent/KE2806A/xx unknown
1978
- 1978-03-02 HK HK12478A patent/HK12478A/xx unknown

Also Published As

Publication number	Publication date
DE2443079A1 (de)	1975-03-20
AT336581B (de)	1977-05-10
JPS5076042A (de)	1975-06-21
HK12478A (en)	1978-03-10
NL7411932A (nl)	1975-03-12
ATA724374A (de)	1976-09-15
KE2806A (en)	1978-02-17
DK495973A (de)	1975-05-12
GB1442477A (en)	1976-07-14

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US2581889A (en)	1952-01-08	Method of preparing pyrimidopyrazines
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US4985563A (en)	1991-01-15	Process for the preparation of 6-piperidino-2,4-diamino pyrimidine-3-oxide
KR970005910B1 (ko)	1997-04-22	퀴놀린 카복실산의 제조방법
US4440928A (en)	1984-04-03	Process for preparation of uracils
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US4423219A (en)	1983-12-27	Production of purine derivatives and intermediates therefor
CS261250B2 (en)	1989-01-12	Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production
US4137411A (en)	1979-01-30	Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines
US4024136A (en)	1977-05-17	Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide
US5648490A (en)	1997-07-15	Process for the preparation of 5-formylaminopyrimidines
SU567402A3 (ru)	1977-07-30	Способ получени производных хинолина или их солей
KR930010559B1 (ko)	1993-10-28	1-히드록시알킬크산틴류, 그의 제조방법
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