ES446083A1 - Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture - Google Patents

Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Info

Publication number
ES446083A1
ES446083A1 ES446083A ES446083A ES446083A1 ES 446083 A1 ES446083 A1 ES 446083A1 ES 446083 A ES446083 A ES 446083A ES 446083 A ES446083 A ES 446083A ES 446083 A1 ES446083 A1 ES 446083A1
Authority
ES
Spain
Prior art keywords
carbon atoms
amino
case
lower alkyl
alkyl
Prior art date
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
ES446083A
Other languages
Spanish (es)
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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.)
Filing date
Publication date
Priority claimed from CH244473A external-priority patent/CH584209A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of ES446083A1 publication Critical patent/ES446083A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom

Landscapes

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

Abstract

Procedure for obtaining derivatives of 2-hydroxy-3-aminopropane with beta-receptor activity, of the formula: ** (See formula) ** where Het means pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl; R1 signifies hydrogen or methyl; R2 means lower alkyl with up to 7 carbon atoms; phenylalkyl with up to 7 carbon atoms in the alkyl part, optionally substituted by lower alkyl or lower alkoxy groups, in each case with up to 7 carbon atoms, trifluoromethyl or halogen, cyano lower alkyl or lower carboxyalkyl, in each case with up to 7 carbon atoms in the lower alkyl part, or lower carboxyalkyl with up to 7 carbon atoms in the lower alkyl part, esterified by a cycloalkanol with 3 to 7 ring members, or by a lower alkanol or a lower phenylalkanol, in each case with up to 7 carbon atoms in the lower alkyl part, optionally substituted by halogen, lower alkyl or lower alkoxy, in each case with up to 7 carbon atoms, or carbamoylalkyl with up to 7 carbon atoms, optionally substituted in the nitrogen atom by one or two lower alkyl moieties, in each case with up to 7 carbon atoms in the lower alkyl part, or by lower alkylene with 3-7 atoms of carbon in the alkyl chain, or by lower oxaalkylene or lower thiaalkylene, in each case with 4 or 5 carbon atoms in the lower alkylene chain or by lower azaalkylene with 2-6 carbon atoms in the lower alkylene chain; R3 stands for hydrogen, halogen, cyano, hydroxy, lower alkyl, lower alkoxy-lower alkyl, amino lower alkyl, lower alkoxy-lower alkenyl, lower alkyl-amino, dialkyl lower amino or lower alkyl sulfonyl, in each case with up to 7 atoms carbon in the lower alkyl, lower alkanoyl-amino, or phenyl-lower alkanoyl-amino part, in each case with up to 7 carbon atoms in the lower alkyl part, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl , lower alkoxy, lower alkenyloxy, or lower alkoxy-methyl, in each case with up to 7 carbon atoms in the lower residues, or lower alkoxy-carbonyl-amino, with up to 7 carbon atoms in the lower alkyl, lower alkanoyl- part. amino-lower alkyl, lower alkanoyl-amino-lower alkylene or phenylalkanoyl-amino-lower alkyl or phenylalkanoyl-lower-amino-lower alkylene, in each case with up to 7 car atoms bond in the lower radicals, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-methyl, in each case with up to 7 carbon atoms in the lower radicals, lower alkoxycarbonylamino -lower alkyl or lower alkoxy-carbonylamino-lower alkylene, in each case with up to 7 carbon atoms in the lower residues, and R4 means hydrogen, halogen, lower alkyl, hydroxy-lower alkyl, lower alkenyl, lower alkoxy, lower alkoxy- lower alkyl amino-lower alkyl, lower alkoxy-lower alkoxy, lower alkenyloxy, lower alkylthio, lower alkylthio-lower alkoxy, lower alkylthio-lower alkyl, lower alkyl-amino, dialkyl lower amino, lower alkyl sulfonyl or lower alkoxy carbonyl , in each cago with up to 7 carbon atoms in the lower alkyl, hydroxy, lower alkylene-amino or hydroxyalkylene lower amino part, in each case with 4-8 ring members and 3-7 carbon atoms in the alkyl, oxa-lower-amino or thiaalkylene-lower-amino chain, in each case with 4-5 carbon atoms in the alkylene-lower azaalkylene chain -amino with 2-6 carbon atoms in the alkylene, phenyl chain, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy-methyl, lower alkoxy or lower alkenyloxy, in each case with up to 7 atoms of carbon in the lower radicals, or phenylthio, optionally substituted by halogen, trifluoromethyl, lower alkyl or lower alkoxy with up to 7 carbon atoms, lower alkanoyl-amino or phenyl-lower alkanoyl-amino in each case with up to 7 carbon atoms in the lower alkyl part, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-methyl, in each case with up to 7 carbon atoms in l the lower residues, or lower alkoxycarbonylamino with up to 7 carbon atoms in the lower alkyl part, and R5 means lower alkanoyl-amino, or phenyl-lower alkanoyl amino in each case with up to 7 carbon atoms in the lower alkane part, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy -methyl, in each case with up to 7 carbon atoms in the lower residues, or lower alkoxy-carbonylamino with up to 7 carbon atoms in the lower alkyl part, and n has values 1, 2 or 3, under the condition that when R3 and R4 signify hydrogen, R5 and n have the indicated meanings in the case that Het means pyridyl, or that, when R5 signifies hydrogen, R3 and R4 have the stated meaning when Het signifies pyrazinyl, pyridazinyl or pyrimidinyl, where at least one of the residues R3 and R4 exclusively mean lower-alkanoyl-amino or phenylalkanoyl-lower-amino in each case with up to 7 carbon atoms in the lower-alkane part, optionally sub ituido by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-methyl, in each case with up to 7 carbon atoms in the lower residues, or lower alkoxy-carbonylamino with up to 7 carbon atoms in the lower alkyl part, as well as its N-oxides and salts, especially the acid addition salts of therapeutic application, characterized in that a compound of formula: ** (See formula) ** where X3 signifies the primary amino group or the R3 moiety; X4 means the primary amino group or the R4 moiety; X5 means the primary amino group and n has the values 1, 2 or 3, under the condition that when X3 and X4 signify hydrogen and n have the indicated meaning in case Het signifies pyridyl, or that when X5 signifies hydrogen X3 and X4 have the meaning indicated when Het means pyrazinyl, pyridazinyl or pyrimidyl where at least one of the residues X3 and X4 exclusively signifies the primary amino group, as well as its N-oxides, is reacted with a lower alkane-carboxylic acid or with a phenylalkanoic acid lower-carboxylic, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-methyl, in each case with up to 7 carbon atoms in the lower radicals, or with a lower alkoxy acid -carboxylic with up to 7 carbon atoms in the lower alkyl part or with a reactive derivative thereof. (Machine-translation by Google Translate, not legally binding)
ES446083A 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture Expired ES446083A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH244473A CH584209A5 (en) 1973-02-20 1973-02-20 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity
FI193/74A FI60391C (en) 1973-02-20 1974-01-23 ANALOGIFICATION OF FRAMSTATION WITH BETA-RECEPTOR-ACTIVE 1-HETEROCYCLYLOXY-3-AMINO-2-PROPANOLFOERING

Publications (1)

Publication Number Publication Date
ES446083A1 true ES446083A1 (en) 1977-09-16

Family

ID=25690464

Family Applications (2)

Application Number Title Priority Date Filing Date
ES76446081A Expired ES446081A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture
ES446083A Expired ES446083A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES76446081A Expired ES446081A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Country Status (15)

Country Link
AR (6) AR208397A1 (en)
AT (1) AT335455B (en)
BE (1) BE811274A (en)
CA (1) CA1027131A (en)
CS (1) CS203970B2 (en)
DD (1) DD110041A5 (en)
DE (1) DE2406930A1 (en)
DK (1) DK143501C (en)
ES (2) ES446081A1 (en)
FR (1) FR2218101B1 (en)
GB (1) GB1465946A (en)
IE (1) IE38839B1 (en)
IL (1) IL44202A (en)
LU (1) LU69415A1 (en)
SE (1) SE420834B (en)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4195090A (en) * 1973-02-20 1980-03-25 Ciba-Geigy Corporation 2-(3-Amino-2-hydroxy-propoxy)pyridine derivatives and pharmaceutical compositions therewith
US4000282A (en) * 1974-12-16 1976-12-28 Merck & Co., Inc. 2-(3-tert. butyl or isopropylamino-2-hydroxypropoxy)-3-cyanopyridines
JPS5283759A (en) * 1976-01-01 1977-07-12 Merck & Co Inc Substituted pyridines
US4060601A (en) * 1976-06-15 1977-11-29 Merck & Co., Inc. Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines
US4092419A (en) * 1976-06-15 1978-05-30 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
US4091104A (en) * 1976-06-15 1978-05-23 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
DE2711655A1 (en) * 1977-03-17 1978-09-21 Basf Ag PYRIDINYL-AMINOALKYLAETHER
US4166851A (en) * 1977-05-16 1979-09-04 Merck & Co., Inc. Certain imidazo(1,2a)pyridine derivatives
US4753673A (en) * 1977-07-22 1988-06-28 The Dow Chemical Company Trifluoromethyl pyridinyloxyphenoxy and pyridinylthiophenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use
JPS54106476A (en) * 1978-01-04 1979-08-21 Merck & Co Inc Multiisubstituted 22*33lower alkylaminoo22 r100propoxy*pyridine
US4279913A (en) * 1978-01-04 1981-07-21 Merck & Co., Inc. Polysubstituted-2-(3-loweralkylamino-2-R1 O-propoxy)pyridines
US4144343A (en) * 1978-01-04 1979-03-13 Merck & Co., Inc. Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines
US4210653A (en) * 1978-06-27 1980-07-01 Merck & Co., Inc. Pyridyloxypropanolamines
DK267779A (en) * 1978-06-27 1979-12-28 Merck & Co Inc PROCEDURE FOR THE PREPARATION OF N-ARALKYLAMINO-PROPOXYCYANOPYRIDINES
US4208416A (en) * 1978-06-27 1980-06-17 Merck & Co., Inc. N-Aralkyl containing cyanopyridines
US4294969A (en) * 1979-01-29 1981-10-13 Merck & Co., Inc. Process for producing 2-bromo-3,5-disubstituted pyridines
US4393212A (en) * 1979-01-29 1983-07-12 Merck & Co., Inc. Certain nicotinic acid esters and corresponding nicotinonitriles
DD150456A5 (en) * 1979-03-01 1981-09-02 Ciba Geigy Ag PROCESS FOR THE PREPARATION OF DERIVATIVES OF 3-AMINO-1,2-PROPANDIOL
US4281005A (en) 1979-03-05 1981-07-28 Merck & Co., Inc. Novel 2-pyridylimidazole compounds
IT1165040B (en) * 1979-04-23 1987-04-22 Isf Spa ALCOSSIALKILIDENIDRAZINOPIRIDAZIONE AND PROCEDURE FOR THEIR PREPARATION
DE2943774A1 (en) * 1979-10-26 1981-05-14 1000 Berlin Schering Ag Berlin Und Bergkamen SUBSTITUTED PYRIDINE, METHOD FOR THEIR PRODUCTION AND THEIR USE
IL62602A (en) * 1980-05-19 1984-06-29 Labaz Sanofi Nv Pyridoxine derivatives,their preparation and pharmaceutical compositions containing them
FR2502618A1 (en) * 1981-03-25 1982-10-01 Synthelabo PYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
US4517188A (en) * 1983-05-09 1985-05-14 Mead Johnson & Company 1-Pyrimidinyloxy-3-hetaryl-alkylamino-2-propanols
US4598149A (en) * 1984-03-02 1986-07-01 Merck & Co., Inc. 3-amino-2-hydroxypropyl of pyrimidin-4-one useful as antihypertensive, cardioprotective, antiarrythmic, and antianginal agents
US6465467B1 (en) 1999-05-21 2002-10-15 Biovitrum Ab Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
US7361671B2 (en) * 2001-11-15 2008-04-22 The Institute For Pharmaceutical Discovery, Inc. Substituted heteroarylalkanoic acids
IL165220A0 (en) 2002-06-19 2005-12-18 Biovitrum Ab Novel compounds, their use and preparation
JP2006509790A (en) * 2002-11-27 2006-03-23 アルテシアン セラピューティック，インコーポレイティド Compounds with mixed PDE inhibition and beta-adrenergic antagonist activity or partial agonist activity for the treatment of heart failure
JP2008507491A (en) * 2004-07-23 2008-03-13 バイエル・クロツプサイエンス・エス・アー 3-pyridinylethylbenzamide derivatives as fungicides
AU2010295288A1 (en) * 2009-09-21 2012-05-03 Johnson & Johnson O-benzyl nicotinamide analogs as mGluR5 positive allosteric modulators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1001631A (en) * 1972-05-05 1976-12-14 Merck Sharp And Dohme (I.A.) Corp. 2-(3-substituted amino-2-hydroxy-propoxy)-3-substituted pyrazines and method for preparation

Also Published As

Publication number Publication date
GB1465946A (en) 1977-03-02
CA1027131A (en) 1978-02-28
DE2406930A1 (en) 1974-08-22
FR2218101A1 (en) 1974-09-13
AT335455B (en) 1977-03-10
AR206801A1 (en) 1976-08-23
AR208043A1 (en) 1976-11-22
LU69415A1 (en) 1975-12-09
FR2218101B1 (en) 1977-07-15
IL44202A (en) 1978-10-31
DK143501C (en) 1982-02-22
IL44202A0 (en) 1974-06-30
IE38839L (en) 1974-08-20
BE811274A (en) 1974-08-19
ES446081A1 (en) 1977-06-16
SE420834B (en) 1981-11-02
AR208397A1 (en) 1976-12-27
IE38839B1 (en) 1978-06-07
AR203878A1 (en) 1975-10-31
DD110041A5 (en) 1974-12-05
ATA133074A (en) 1976-07-15
AR214612A1 (en) 1979-07-13
CS203970B2 (en) 1981-03-31
AR207133A1 (en) 1976-09-15
DK143501B (en) 1981-08-31

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