CA1030552A - Process for preparation of novel butyramide derivatives - Google Patents

Process for preparation of novel butyramide derivatives

Info

Publication number: CA1030552A
Authority: CA; Canada
Prior art keywords: revendication; représente; atome; que; procédé selon
Prior art date: 1973-09-03
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

CA208,178A

Other languages

English (en)

French (fr)

Other versions

CA208178S (en

Inventor

Jean Meier

Anne Farthouat

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.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

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.)

1973-09-03

Filing date

1974-08-30

Publication date

1978-05-02

1974-08-30 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1978-05-02 Application granted granted Critical

1978-05-02 Publication of CA1030552A publication Critical patent/CA1030552A/en

Status Expired legal-status Critical Current

Links

DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical class CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 title claims abstract description 12
230000009471 action Effects 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
150000008064 anhydrides Chemical class 0.000 claims description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 2
CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 claims description 2
DJQAPXOHSUIFSU-UHFFFAOYSA-N n-hydroxy-n-methylbutanamide Chemical compound CCCC(=O)N(C)O DJQAPXOHSUIFSU-UHFFFAOYSA-N 0.000 claims 2
CCBCHURBDSNSTJ-UHFFFAOYSA-N n-hydroxybutanamide Chemical compound CCCC(=O)NO CCBCHURBDSNSTJ-UHFFFAOYSA-N 0.000 claims 2
KHNDGDMDYRDYBR-UHFFFAOYSA-N n-methoxy-n-methylbutanamide Chemical compound CCCC(=O)N(C)OC KHNDGDMDYRDYBR-UHFFFAOYSA-N 0.000 claims 2
NIMJYJAQJPIOBE-UHFFFAOYSA-N n-methoxybutanamide Chemical compound CCCC(=O)NOC NIMJYJAQJPIOBE-UHFFFAOYSA-N 0.000 claims 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract 3
239000002253 acid Substances 0.000 abstract 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000003545 alkoxy group Chemical group 0.000 abstract 1
230000000202 analgesic effect Effects 0.000 abstract 1
230000003110 anti-inflammatory effect Effects 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229940090044 injection Drugs 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000012360 testing method Methods 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000699729 Muridae Species 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
229910006124 SOCl2 Inorganic materials 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
-1 amidon Substances 0.000 description 1
230000003416 augmentation Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
206010037833 rales Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

Landscapes

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

CA208,178A 1973-09-03 1974-08-30 Process for preparation of novel butyramide derivatives Expired CA1030552A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7331699A FR2242077B1 (de)	1973-09-03	1973-09-03

Publications (1)

Publication Number	Publication Date
CA1030552A true CA1030552A (en)	1978-05-02

Family

ID=9124547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA208,178A Expired CA1030552A (en)	1973-09-03	1974-08-30	Process for preparation of novel butyramide derivatives

Country Status (19)

Country	Link
JP (1)	JPS5050345A (de)
AT (1)	AT335998B (de)
BE (1)	BE819456A (de)
CA (1)	CA1030552A (de)
CH (1)	CH587799A5 (de)
DD (1)	DD116028A5 (de)
DE (1)	DE2442124A1 (de)
DK (1)	DK464674A (de)
ES (1)	ES429717A1 (de)
FR (1)	FR2242077B1 (de)
GB (1)	GB1444492A (de)
HU (1)	HU168678B (de)
IE (1)	IE40649B1 (de)
IL (1)	IL45506A (de)
LU (1)	LU70832A1 (de)
NL (1)	NL7411702A (de)
SE (1)	SE414496B (de)
SU (1)	SU576919A3 (de)
ZA (1)	ZA745400B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU201300B (en) *	1985-03-16	1990-10-28	Wellcome Found	Process for production of derivatives of aryl and medical compositions containing them as active substance
GB8531839D0 (en) *	1985-12-30	1986-02-05	Wellcome Found	Aryl derivatives
EP0301861B1 (de) *	1987-07-29	1992-04-01	Takeda Chemical Industries, Ltd.	Zellproliferationsinhibitor
US5028629A (en) *	1990-03-28	1991-07-02	Eli Lilly And Company	5-Lipoxygenase inhibitors
AU6701694A (en)	1993-04-16	1994-11-08	Mccormick & Company, Inc.	Encapsulation compositions
US7348437B2 (en) *	2004-06-01	2008-03-25	The Scripps Research Institute	Proteomic analysis

1973
- 1973-09-03 FR FR7331699A patent/FR2242077B1/fr not_active Expired
1974
- 1974-08-05 SE SE7410046-2A patent/SE414496B/xx unknown
- 1974-08-13 DD DD180466A patent/DD116028A5/xx unknown
- 1974-08-20 IL IL45506A patent/IL45506A/xx unknown
- 1974-08-22 ZA ZA00745400A patent/ZA745400B/xx unknown
- 1974-08-28 JP JP49098005A patent/JPS5050345A/ja active Pending
- 1974-08-30 LU LU70832A patent/LU70832A1/xx unknown
- 1974-08-30 CA CA208,178A patent/CA1030552A/en not_active Expired
- 1974-08-30 HU HURO793A patent/HU168678B/hu unknown
- 1974-09-02 GB GB3829174A patent/GB1444492A/en not_active Expired
- 1974-09-02 ES ES429717A patent/ES429717A1/es not_active Expired
- 1974-09-02 BE BE148139A patent/BE819456A/xx unknown
- 1974-09-02 CH CH1190174A patent/CH587799A5/xx not_active IP Right Cessation
- 1974-09-02 SU SU7402063057A patent/SU576919A3/ru active
- 1974-09-03 NL NL7411702A patent/NL7411702A/xx not_active Application Discontinuation
- 1974-09-03 DK DK464674A patent/DK464674A/da not_active Application Discontinuation
- 1974-09-03 AT AT710474A patent/AT335998B/de not_active IP Right Cessation
- 1974-09-03 IE IE1819/74A patent/IE40649B1/xx unknown
- 1974-09-03 DE DE2442124A patent/DE2442124A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
ZA745400B (en)	1975-10-29
FR2242077B1 (de)	1977-01-28
IL45506A0 (en)	1974-11-29
HU168678B (de)	1976-06-28
ATA710474A (de)	1976-08-15
GB1444492A (en)	1976-07-28
BE819456A (fr)	1975-03-03
SE7410046L (de)	1975-03-04
IE40649L (en)	1975-03-03
ES429717A1 (es)	1977-04-01
LU70832A1 (de)	1975-06-11
DD116028A5 (de)	1975-11-05
SE414496B (sv)	1980-08-04
DE2442124A1 (de)	1975-03-06
IE40649B1 (en)	1979-07-18
AU7260674A (en)	1976-02-26
NL7411702A (nl)	1975-03-05
JPS5050345A (de)	1975-05-06
AT335998B (de)	1977-04-12
CH587799A5 (de)	1977-05-13
FR2242077A1 (de)	1975-03-28
DK464674A (de)	1975-05-05
IL45506A (en)	1978-07-31
SU576919A3 (ru)	1977-10-15

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