BE904930A - 4-(n-methyl-n-nicotinoyl)-amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one et compose ainsi obtenu. - Google Patents

4-(n-methyl-n-nicotinoyl)-amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one et compose ainsi obtenu. Download PDF

Info

Publication number: BE904930A
Authority: BE; Belgium
Prior art keywords: methyl; phenyl; dimethyl; pyrazoline; amino
Prior art date: 1986-05-15

Application number

BE0/216789A

Other languages

English (en)

French (fr)

Inventor

L Mazzoni

Original Assignee

Ibis Ist Biochim Speriment

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.)

1986-05-15

Filing date

1986-06-16

Publication date

1986-12-16

1986-06-16 Application filed by Ibis Ist Biochim Speriment filed Critical Ibis Ist Biochim Speriment

1986-12-16 Publication of BE904930A publication Critical patent/BE904930A/fr

Links

150000001875 compounds Chemical class 0.000 title description 2
238000000034 method Methods 0.000 claims description 9
JILCEWWZTBBOFS-UHFFFAOYSA-N 4-(methylamino)antipyrine Chemical compound O=C1C(NC)=C(C)N(C)N1C1=CC=CC=C1 JILCEWWZTBBOFS-UHFFFAOYSA-N 0.000 abstract description 14
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract description 7
150000008064 anhydrides Chemical class 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
229960003512 nicotinic acid Drugs 0.000 abstract description 3
235000001968 nicotinic acid Nutrition 0.000 abstract description 3
239000011664 nicotinic acid Substances 0.000 abstract description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
GCIGZRAXWDUHRE-UHFFFAOYSA-N n-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-n-methylpyridine-3-carboxamide Chemical compound CC=1N(C)N(C=2C=CC=CC=2)C(=O)C=1N(C)C(=O)C1=CC=CN=C1 GCIGZRAXWDUHRE-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
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
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XZQXOUJKVOYPAH-UHFFFAOYSA-N 4,5-dimethyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C)=C(C)NN1C1=CC=CC=C1 XZQXOUJKVOYPAH-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BE0/216789A 1986-05-15 1986-06-16 4-(n-methyl-n-nicotinoyl)-amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one et compose ainsi obtenu. BE904930A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT20439/86A IT1204352B (it)	1986-05-15	1986-05-15	Procedimento per la preparazione di 4-(n-metil-n-nicotinoil)-amino-2,3-dimetil-1-fenil-3-pirazolin-5-one e composto cosi' ottenuto

Publications (1)

Publication Number	Publication Date
BE904930A true BE904930A (fr)	1986-12-16

Family

ID=11166959

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/216789A BE904930A (fr)	1986-05-15	1986-06-16	4-(n-methyl-n-nicotinoyl)-amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one et compose ainsi obtenu.

Country Status (2)

Country	Link
BE (1)	BE904930A (it)
IT (1)	IT1204352B (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105801487A (zh) *	2014-12-31	2016-07-27	浙江海森药业有限公司	一种4-甲氨基安替比林的制备方法

1986
- 1986-05-15 IT IT20439/86A patent/IT1204352B/it active
- 1986-06-16 BE BE0/216789A patent/BE904930A/fr not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105801487A (zh) *	2014-12-31	2016-07-27	浙江海森药业有限公司	一种4-甲氨基安替比林的制备方法

Also Published As

Publication number	Publication date
IT8620439A0 (it)	1986-05-15
IT1204352B (it)	1989-03-01

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Legal Events

Date

Code

Title

Description

1990-12-31

RE

Patent lapsed

Owner name: ISTITUTO BIOCHIMICO SPERIMENTALE IBIS S.P.A.

Effective date: 19900630