CA1104158A - N,n'-bis(phenylcarbamoylmethyl)amidines antiarythmiques - Google Patents

N,n'-bis(phenylcarbamoylmethyl)amidines antiarythmiques

Info

Publication number: CA1104158A
Authority: CA; Canada
Prior art keywords: alkyl; hydrogen; formula; bis; halo
Prior art date: 1977-09-30
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

CA311,221A

Other languages

English (en)

Inventor

Ronald A. Wohl

Julius Diamond

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.)

Berlex Laboratories Inc

Original Assignee

Berlex Laboratories Inc

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.)

1977-09-30

Filing date

1978-09-13

Publication date

1981-06-30

1978-09-13 Application filed by Berlex Laboratories Inc filed Critical Berlex Laboratories Inc

1981-06-30 Application granted granted Critical

1981-06-30 Publication of CA1104158A publication Critical patent/CA1104158A/fr

Status Expired legal-status Critical Current

Links

230000003288 anthiarrhythmic effect Effects 0.000 title abstract description 8
150000001409 amidines Chemical class 0.000 title abstract description 3
239000003416 antiarrhythmic agent Substances 0.000 title description 4
239000002253 acid Substances 0.000 claims abstract description 26
QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical compound NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 42
238000000034 method Methods 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 31
230000008569 process Effects 0.000 claims description 20
150000002431 hydrogen Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
150000002905 orthoesters Chemical class 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 4
IXYVBZOSGGJWCW-UHFFFAOYSA-N glycinexylidide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN IXYVBZOSGGJWCW-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
NXCNEIVTXXRMOY-UHFFFAOYSA-N 2-amino-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)CN NXCNEIVTXXRMOY-UHFFFAOYSA-N 0.000 claims description 2
JMIAPORGEDIDLT-UHFFFAOYSA-N ethyl ethanimidate Chemical compound CCOC(C)=N JMIAPORGEDIDLT-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 21
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 9
125000001475 halogen functional group Chemical group 0.000 claims 9
DMYHLFGTKCOQFY-UHFFFAOYSA-N 2-[[n-[2-(2,6-dimethylanilino)-2-oxoethyl]-c-methylcarbonimidoyl]amino]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC=1C=CC=C(C)C=1NC(=O)CN=C(C)NCC(=O)NC1=C(C)C=CC=C1C DMYHLFGTKCOQFY-UHFFFAOYSA-N 0.000 claims 4
241001334141 Rugopharynx alpha Species 0.000 claims 4
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 3
AAZJNLRTMAETDT-UHFFFAOYSA-N 2-[[n-[2-(2,6-diethylanilino)-2-oxoethyl]-c-methylcarbonimidoyl]amino]-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)CNC(C)=NCC(=O)NC1=C(CC)C=CC=C1CC AAZJNLRTMAETDT-UHFFFAOYSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
229910052801 chlorine Inorganic materials 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 11
-1 PHENYLcARBAMOYL Chemical class 0.000 description 111
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 7
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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239000003153 chemical reaction reagent Substances 0.000 description 4
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WDPUBTBNJLUJEI-UHFFFAOYSA-N 2-[[n-[2-(2,6-dimethylanilino)-2-oxoethyl]-c-methylcarbonimidoyl]amino]-n-(2,6-dimethylphenyl)acetamide;hydrochloride Chemical compound Cl.CC=1C=CC=C(C)C=1NC(=O)CN=C(C)NCC(=O)NC1=C(C)C=CC=C1C WDPUBTBNJLUJEI-UHFFFAOYSA-N 0.000 description 3
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PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
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QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
244000166550 Strophanthus gratus Species 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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YHAPAUHGCSXAMR-UHFFFAOYSA-N 3-carbamimidoyl-N,N'-bis(2,6-diethylphenyl)pentanediamide Chemical compound C(C)C1=C(C(=CC=C1)CC)NC(=O)CC(C(=N)N)CC(NC1=C(C=CC=C1CC)CC)=O YHAPAUHGCSXAMR-UHFFFAOYSA-N 0.000 description 1
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125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
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230000002194 synthesizing effect Effects 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
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239000011975 tartaric acid Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
210000000779 thoracic wall Anatomy 0.000 description 1
238000004448 titration Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
210000001186 vagus nerve Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1

Landscapes

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

CA311,221A 1977-09-30 1978-09-13 N,n'-bis(phenylcarbamoylmethyl)amidines antiarythmiques Expired CA1104158A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US83840477A	1977-09-30	1977-09-30
US838,404		1977-09-30

Publications (1)

Publication Number	Publication Date
CA1104158A true CA1104158A (fr)	1981-06-30

Family

ID=25277023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA311,221A Expired CA1104158A (fr)	1977-09-30	1978-09-13	N,n'-bis(phenylcarbamoylmethyl)amidines antiarythmiques

Country Status (6)

Country	Link
JP (1)	JPS5918388B2 (fr)
CA (1)	CA1104158A (fr)
DE (1)	DE2840747C2 (fr)
FR (1)	FR2437404A1 (fr)
GB (1)	GB2006760B (fr)
IT (1)	IT1202838B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5872122A (en) *	1997-10-16	1999-02-16	Monsanto Company	Pyrimidinylamidino β-amino acid derivatives useful as inhibitors of platelet aggregation

1978
- 1978-09-13 CA CA311,221A patent/CA1104158A/fr not_active Expired
- 1978-09-15 DE DE19782840747 patent/DE2840747C2/de not_active Expired
- 1978-09-28 GB GB7838516A patent/GB2006760B/en not_active Expired
- 1978-09-29 IT IT51319/78A patent/IT1202838B/it active
- 1978-09-29 JP JP11942578A patent/JPS5918388B2/ja not_active Expired
- 1978-09-29 FR FR7827906A patent/FR2437404A1/fr active Granted

Also Published As

Publication number	Publication date
GB2006760A (en)	1979-05-10
FR2437404A1 (fr)	1980-04-25
DE2840747C2 (de)	1983-03-10
IT7851319A0 (it)	1978-09-29
JPS5473735A (en)	1979-06-13
GB2006760B (en)	1982-03-31
IT1202838B (it)	1989-02-09
JPS5918388B2 (ja)	1984-04-26
FR2437404B1 (fr)	1983-01-07
DE2840747A1 (de)	1979-04-12

Legal Events

Date	Code	Title	Description
1998-06-30	MKEX	Expiry

Publication	Publication Date	Title
US4225591A (en)	1980-09-30	2,6-Diaminonebularines
US4072759A (en)	1978-02-07	Novel benzylalcohol derivatives as antidiabetics and cardiotonics
EP0113778B1 (fr)	1990-05-09	Derives d'aminomethylbenzene aryl-substitues utiles comme agents antiarythmiques
US3987177A (en)	1976-10-19	Vincaminic acid esters
SU1297724A3 (ru)	1987-03-15	Способ получени производных флуорена
US4169106A (en)	1979-09-25	Antiarrhythmic N,N'-bis(phenylcarbamoylalkyl)amidines
JPS6350347B2 (fr)	1988-10-07
CY1272A (en)	1985-03-08	Urea derivatives
Doub et al.	1951	Some derivatives of 4-amino-2-hydroxybenzoic acid (p-aminosalicylic acid)
JPS63255258A (ja)	1988-10-21	Ｎ−フェネチルアミノアルキル−ベンズアミド抗不整脈剤
CA1129875A (fr)	1982-08-17	Derives de chromone
JPH0471067B2 (fr)	1992-11-12
JPS6147808B2 (fr)	1986-10-21
US4143143A (en)	1979-03-06	Substituted imidazo[5,1-a]isoquinolines
ES2207325T3 (es)	2004-05-16	((aminoiminomethil) amino) alcanocarboxamidas y sus aplicaciones terapeuticas.
DE2840747C2 (de)	1983-03-10	N,N'-bis(Phenylcarbamoylmethyl)amidine
US4237068A (en)	1980-12-02	Primary aminoacylanilides
US4229462A (en)	1980-10-21	Method for controlling hypertension and compositions
JPS6350346B2 (fr)	1988-10-07
US4139537A (en)	1979-02-13	3-Aryloxy-1-(2- or 4-iminodihydro-1-pyridyl)-2-propanol antiarrhythmic compounds
GB2100261A (en)	1982-12-22	Aminophenylalkylamine derivatives, a process for their preparation and their use as pharmaceuticals
SU971098A3 (ru)	1982-10-30	Способ получени производных N-арил-N @ -/2-имидазолидинилиден/-мочевины
JPS6059230B2 (ja)	1985-12-24	不整脈抑制性フエネチルピペリジン化合物
US3100208A (en)	1963-08-06	N1-(p-toluene sulfonyl)-n2-(alpha-tetrahydrofuryl methyl) urea
US3846436A (en)	1974-11-05	Piperidinoethyl and piperidinoethoxyethyl esters of 2,2-diaryl-cyclopropane-carboxylic acids