ES424500A1 - A procedure for the preparation of derivatives of 1-amino (replaced) -2-oxy) -2-propanol. (Machine-translation by Google Translate, not legally binding) - Google Patents

A procedure for the preparation of derivatives of 1-amino (replaced) -2-oxy) -2-propanol. (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES424500A1
ES424500A1 ES424500A ES424500A ES424500A1 ES 424500 A1 ES424500 A1 ES 424500A1 ES 424500 A ES424500 A ES 424500A ES 424500 A ES424500 A ES 424500A ES 424500 A1 ES424500 A1 ES 424500A1
Authority
ES
Spain
Prior art keywords
carbon atoms
group
alkyl
substituted
formula
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
ES424500A
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.)
Syntex USA LLC
Original Assignee
Syntex USA LLC
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 US451179A external-priority patent/US3897441A/en
Application filed by Syntex USA LLC filed Critical Syntex USA LLC
Publication of ES424500A1 publication Critical patent/ES424500A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/58—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

A method of preparing 1-amino (substituted) -3- (4'-or 5'-thiazole (substituted) -2-oxy-2-propanol derivatives of the formula: **(See formula)** where R1 and R2 are independently selected from the group consisting of hydrogen, lower alkyl, cycloalkyl of 3 to 7 ring atoms, lower alkenyl, aryl, arylalkyl, lower alkylaryl, lower alkoxy, lower alkyl, lower alkyl (N-heterocyclic containing from 5 to 7 ring atoms including one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and where at least one of said heteroatoms is nitrogen) and groups of formulas **(See formula)** where n is an integer from 1 to 4; and R11 and R12 are independently hydrogen or lower alkyl; or R1 and R2 attached to the nitrogen atom to which they are attached form a nitrogenous heterocycle of 5 to 7 atoms in the ring containing 1 or 2 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and where at least one of said heteroatoms is nitrogen or R1 and R2 form a substituted nitrogen heterocycle of 5 to 7 ring atoms including 1 or 2 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and where at least one of said heteroatoms is nitrogen and containing one or two substituents independently selected from the group consisting of lower alkyl and hydroxyalkyl lower; Z is a substituent on the thiazole ring at position 4 or 5, selected from the group of formulas **(See formula)** where one of the radicals R3 or R4 is independently selected from the group consisting of alkyl of 7 to 12 carbon atoms; cycloalkyl of 3 to 12 carbon atoms; terminally substituted alkyl group containing from 2 to 12 carbon atoms with a substituted terminal carbon atom bearing a substituent selected from the group consisting of hydroxy, acyloxy of 2 to 12 carbon atoms, and alkoxy of 1 to 6 carbon atoms; and formula groups **(See formula)** where n is an integer from 1 to 4 and R8 and R9 are independently selected from hydrogen and alkyl groups of 1 to 4 carbon atoms and R10 is cycloalkyl of 3 to 8 carbon atoms; and the other radical R3 or R4 is selected from the group consisting of hydrogen; alkyl of 1 to 12 carbon atoms; cycloalkyl of 3 to 12 carbon atoms; phenyl, lower phenylalkyl where the alkyl radical contains 1 to 6 carbon atoms, substituted phenyl and substituted phenylalkyl where said phenyl ring carries one or two substituents independently selected from hydroxy, lower alkyl, lower alkoxy and halogen; a terminally substituted alkyl group containing 2 to 12 carbon atoms, with a substituted terminal carbon atom bearing a substituent selected from the group consisting of hydroxy, acyloxy of 2 to 12 carbon atoms, and alkoxy of 1 to 6 carbon atoms ; and formula groups **(See formula)** where n is an integer from 1 to 4; R8 and R9 are independently selected from hydrogen and alkyl groups of 1 to 4 carbon atoms and R10 is cycloalkyl of 3 to 8 carbon atoms; and where, when one of the radicals R1 or R2 is the group **(See formula)** then R3 and R4 may each be independently selected from the group consisting of hydrogen; alkyl of 1 to 12 carbon atoms; cycloalkyl of 3 to 12 carbon atoms; phenyl, lower phenylalkyl where the alkyl radical contains from 1 to 6 carbon atoms, substituted phenyl and substituted lower phenylalkyl where said phenyl ring carries one or two substituents independently selected from hydroxy, lower alkyl, lower alkoxy and halogen; a terminally substituted alkyl group of 2 to 12 carbon atoms, with a substituted terminal carbon atom bearing a substituent selected from the group, consisting of hydroxy, acyloxy of 2 to 12 carbon atoms, and alkoxy of 1 to 6 carbon atoms ; and formula groups **(See formula)** where n is an integer from 1 to 4; R8 and R9 are independently selected from the group consisting of hydrogen and alkyl groups of 1 to 4 carbon atoms and R10 is cycloalkyl of 3 to 8 carbon atoms; and also with the condition that, when Z is (see formula), then R4 cannot be hydrogen; and its pharmaceutically acceptable salts; whose procedure is to react the corresponding compound of formula **(See formula)** where R3 and R4 are as defined above, with an amine derivative or an N-heterocyclic derivative containing the desired R1 and R2 substituents, thereby giving the corresponding compound of formula I. (Machine-translation by Google Translate, not legally binding)
ES424500A 1973-03-22 1974-03-21 A procedure for the preparation of derivatives of 1-amino (replaced) -2-oxy) -2-propanol. (Machine-translation by Google Translate, not legally binding) Expired ES424500A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US34394573A 1973-03-22 1973-03-22
US451179A US3897441A (en) 1971-10-27 1974-03-14 Certain thiazole-carboxamides and acylamino-thiazoles

Publications (1)

Publication Number Publication Date
ES424500A1 true ES424500A1 (en) 1976-11-01

Family

ID=26993700

Family Applications (2)

Application Number Title Priority Date Filing Date
ES424500A Expired ES424500A1 (en) 1973-03-22 1974-03-21 A procedure for the preparation of derivatives of 1-amino (replaced) -2-oxy) -2-propanol. (Machine-translation by Google Translate, not legally binding)
ES446566A Expired ES446566A1 (en) 1973-03-22 1976-03-31 A procedure for the preparation of derivatives of 1-amino- (replaced) -3-4'-0-5'-tiazol (replaced) -2-oxi-2-propanol. (Machine-translation by Google Translate, not legally binding)

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES446566A Expired ES446566A1 (en) 1973-03-22 1976-03-31 A procedure for the preparation of derivatives of 1-amino- (replaced) -3-4'-0-5'-tiazol (replaced) -2-oxi-2-propanol. (Machine-translation by Google Translate, not legally binding)

Country Status (6)

Country Link
JP (1) JPS5029558A (en)
CA (1) CA1039287A (en)
ES (2) ES424500A1 (en)
IE (1) IE40145B1 (en)
IL (1) IL44460A (en)
SE (2) SE7706067L (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119718A (en) * 1977-05-02 1978-10-10 Merck & Co., Inc. 3-Amino-2-oxy-propoxy-substituted isothiazoles
US11246451B2 (en) 2015-10-12 2022-02-15 Weber-Stephen Products Llc Burner tube for gas grill

Also Published As

Publication number Publication date
IL44460A (en) 1978-12-17
IE40145B1 (en) 1979-03-28
ES446566A1 (en) 1977-11-01
AU6693574A (en) 1975-09-25
IE40145L (en) 1974-09-22
SE7706067L (en) 1977-05-24
SE7706068L (en) 1977-05-24
JPS5029558A (en) 1975-03-25
CA1039287A (en) 1978-09-26

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