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IE38839B1 - 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
IE38839B1
IE38839B1 IE255/74A IE25574A IE38839B1 IE 38839 B1 IE38839 B1 IE 38839B1 IE 255/74 A IE255/74 A IE 255/74A IE 25574 A IE25574 A IE 25574A IE 38839 B1 IE38839 B1 IE 38839B1
Authority
IE
Ireland
Prior art keywords
alkyl
het
dihydroxypropoxy
dichloropyrimidine
allyloxy
Prior art date
Application number
IE255/74A
Other versions
IE38839L (en
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 IE38839L publication Critical patent/IE38839L/en
Publication of IE38839B1 publication Critical patent/IE38839B1/en

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

1465946 Propanolamine derivatives CIBA GEIGY AG 13 Feb 1974 [20 Feb 1973 31 Jan 1974] 6518/74 Heading C2C Compounds of the general formula (I) (Het=optionally substituted pyridazinyl, pyrimidinyl, pyrazinyl or substituted pyridyl, R 1 = H or CH 3 and R 2 =C 1-7 alkyl, optionally substituted phenyl-(C 1-7 , alkyl), carboxy-(C 1-7 , alkyl) or functionally modified carboxy-(C 1-7 alkyl), provided that Het does not represent pyrazin-2 or 3-yl substituted at the 3- or 2-position respectively by C 1-5 alkyl or unsubstituted phenyl when R 1 R 2 CH 3 C- is C 3-6 alkyl or unsubstituted phenyl (C 3-6 ) alkyl, their condensation products with aldehydes, ketones and carbonic acid, and their N-oxides and salts are prepared by reacting (a) Het-O-CH 2 CHX 1 CH 2 Z 1 or an N-oxide thereof with Z 2 CCH 3 R 1 R 2 (one of Z 1,2 =NH 2 , the other=reactive esterified OH and X 1 =OH, or X 1 +Z 1 =O and Z 2 =NH 2 ), (b) Het-Z (Z= nucleophilically removable radical) with HOCH 2 CHOHCH 2 NHCCH 3 R 1 R 2 or the condensation product with an aldehyde, ketone or carbonic acid or (c) 3-hydroxypyridine with ZCH 2 CHX 1 CH 2 NHCCH 3 R 1 R 2 (Z = reactive esterified OH and X 1 = OH, or Z + X 1 = O) or the corresponding azetidine, optionally followed by introduction, modification or removal of substituents, conversion to a different compound of formula (I), isomer separation and/or salt formation. The preparation of starting materials for processes (a) and (b) and 2-allyloxy-3-morpholinopyrazine, 2-allyloxy-3-dimethylaminopyrazine, 2- allyloxy - 3 - isopropylaminopyrazine, 3 - chloro- 2-[2<SP>1</SP>,2<SP>1</SP>-dimethyl-1<SP>1</SP>,3<SP>1</SP>-dioxolanyl-(4<SP>1</SP>)]methoxypyridine, 3 - chloro - 2 - (2<SP>1</SP>,3<SP>1</SP> - dihydroxypropoxy)pyridine, 3 - (2<SP>1</SP>,3<SP>1 </SP>- dihydroxypropoxy)- 2 - methoxypyridine, 2 - [2<SP>1</SP>,2<SP>1</SP> - dimethyl- 1<SP>1</SP>,3<SP>1</SP> - dioxolanyl - (4<SP>1</SP>)] - methoxypyrimidine, 2 - (2<SP>1</SP>,3<SP>1</SP> - dihydroxypropoxy)pyrimidine, 5- hydroxymethyl-, chloromethyl-, cyanomethyl- and # - aminoethyl - 2,3 - dichloropyridine, 3 - benzylamino - 1,2 - propanediol, 3-benzyl - 5 - hydroxymethyl - 2 - phenyloxazolidine, 2 - (3<SP>1</SP> - benzylamino - 21 - hydroxypropoxy) - 3 - methylpyridine, 2 - hydroxy - 3 - chloropyridine - 5 - carboxylic acid, 5 - hexylcarbamoyl - 2,4(6) - dichloropyrimidine, 5 - (# - methoxyethyl)uracil, 5 - (# - methoxyethyl) - 2,4(6) - dichloropyrimidine, 5 - methylthiomethyluracil, 5 - methylthiomethyl - 2,4(6)- dichloropyrimidine and 5-ethyl-4-hydroxypyrimidine is described. Some of the above compounds are #-adrenergic blocking agents and some are stimulants. They may be administered in the form of pharmaceutical and veterinary preparations containing them in association with a carrier. [GB1465946A]
IE255/74A 1973-02-20 1974-02-11 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture IE38839B1 (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 (2)

Publication Number Publication Date
IE38839L IE38839L (en) 1974-08-20
IE38839B1 true IE38839B1 (en) 1978-06-07

Family

ID=25690464

Family Applications (1)

Application Number Title Priority Date Filing Date
IE255/74A IE38839B1 (en) 1973-02-20 1974-02-11 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Country Status (15)

Country Link
AR (6) AR207133A1 (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
US4091104A (en) * 1976-06-15 1978-05-23 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
US4092419A (en) * 1976-06-15 1978-05-30 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
US4060601A (en) * 1976-06-15 1977-11-29 Merck & Co., Inc. Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines
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
US4144343A (en) * 1978-01-04 1979-03-13 Merck & Co., Inc. Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines
US4279913A (en) * 1978-01-04 1981-07-21 Merck & Co., Inc. Polysubstituted-2-(3-loweralkylamino-2-R1 O-propoxy)pyridines
JPS54106476A (en) * 1978-01-04 1979-08-21 Merck & Co Inc Multiisubstituted 22*33lower alkylaminoo22 r100propoxy*pyridine
US4208416A (en) * 1978-06-27 1980-06-17 Merck & Co., Inc. N-Aralkyl containing cyanopyridines
DK267779A (en) * 1978-06-27 1979-12-28 Merck & Co Inc PROCEDURE FOR THE PREPARATION OF N-ARALKYLAMINO-PROPOXYCYANOPYRIDINES
US4210653A (en) * 1978-06-27 1980-07-01 Merck & Co., Inc. Pyridyloxypropanolamines
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
EP1565472A2 (en) * 2002-11-27 2005-08-24 Artesian Therapeutics, Inc. Compounds with mixed pde-inhibitory and beta-adrenergic antagonist or partial agonist activity for treatment of heart failure
EP1773776A1 (en) * 2004-07-23 2007-04-18 Bayer Cropscience Sa 3-pyridinylethylbenzamide derivatives as fungicides
JP2013505297A (en) * 2009-09-21 2013-02-14 ヴァンダービルト ユニバーシティー O-Benzylnicotinamide analogs as positive allosteric modulators of mGluR5

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
CS203970B2 (en) 1981-03-31
AR214612A1 (en) 1979-07-13
DK143501C (en) 1982-02-22
DE2406930A1 (en) 1974-08-22
AR206801A1 (en) 1976-08-23
AR203878A1 (en) 1975-10-31
IL44202A (en) 1978-10-31
DD110041A5 (en) 1974-12-05
BE811274A (en) 1974-08-19
LU69415A1 (en) 1975-12-09
FR2218101B1 (en) 1977-07-15
ES446081A1 (en) 1977-06-16
AR207133A1 (en) 1976-09-15
SE420834B (en) 1981-11-02
AR208043A1 (en) 1976-11-22
ATA133074A (en) 1976-07-15
DK143501B (en) 1981-08-31
CA1027131A (en) 1978-02-28
AR208397A1 (en) 1976-12-27
ES446083A1 (en) 1977-09-16
IE38839L (en) 1974-08-20
FR2218101A1 (en) 1974-09-13
IL44202A0 (en) 1974-06-30
GB1465946A (en) 1977-03-02
AT335455B (en) 1977-03-10

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