ES406345A1 - Aminoalcohol derivatives - Google Patents

Aminoalcohol derivatives

Info

Publication number
ES406345A1
ES406345A1 ES406345A ES406345A ES406345A1 ES 406345 A1 ES406345 A1 ES 406345A1 ES 406345 A ES406345 A ES 406345A ES 406345 A ES406345 A ES 406345A ES 406345 A1 ES406345 A1 ES 406345A1
Authority
ES
Spain
Prior art keywords
group
formula
methyl
phenyl
butyl
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
ES406345A
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.)
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Vegyeszeti Gyar RT
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
Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT
Publication of ES406345A1 publication Critical patent/ES406345A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/84—Xanthenes 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 in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

A process for the preparation of a pharmaceutically active ester or salt of a new amino alcohol of formulas (I) and (II) **(See formula)** where n is an integer from 1 to 4, R1 represents hydrogen or a straight or branched chain lower alkyl or alkenyl group, R2 represents hydrogen, a straight or branched chain lower alkyl or alkenyl group or a phenyl group, R3 represents hydrogen, a straight or branched chain lower alkyl or alkenyl group or a benzyl group, X represents an amino group of general formula (III) **(See formula)** where R4 and R5 each represent an alkyl, cycloalkyl or lower alkenyl group or R4 and R5 can form together an alkylene group or an aliphatic hydrocarbon group where the carbon chain is interrupted by an oxygen atom, X may further represent a 4-hydroxy-4-p-chlorophenyl-piperidine group of formula (IV) **(See formula)** a 4-p-chlorophenyl-tetrahydropyridine group of formula (V) **(See formula)** or a 4-acetoxylidyl-piperazino group of formula (VI) **(See formula)** Y represents a straight or branched chain lower alkyl or haloalkyl group, a phenyl group optionally substituted by one or more alkyl, halogen, hydroxy, alkoxy, methylenedioxy, phenoxy, nitro and/or trifluoromethyl groups and furthermore an alkoxybenzyl or xanthenyl group, Z represents a residue of a pharmaceutically acceptable organic or mineral acid, with the condition of: (1) if R4 and R5 each represent a methyl, ethyl, propyl, isopropyl or butyl group and Y represents a methyl, ethyl, propyl, phenyl or nitrophenyl group optionally with other or more substituents, R1 can be only isopropyl, n- butyl, an isomeric butyl, allyl, metalyl, or phenylallyl and R2 may be only n-butyl, an isomeric butyl, allyl, metalyl, phenylallyl, or phenyl, or respectively (2) if R4 and R5 each represent a methyl, ethyl, propyl, isopropyl or butyl group, n is 1 or 2, R1 is hydrogen or a straight or branched chain alkyl or alkenyl group and R2 is hydrogen, an alkyl group or straight or branched chain alkenyl or a phenyl group, Y may be only an isopropyl, 2-methyl-isopropyl or substituted phenyl group, where the substituent or substituents (s) attached to the phenyl group may be alkyl, halogen, hydroxy, alkoxy, methylenedioxy, phenoxy and/or trifluoromethyl, or respectively, (3) if R4 and R5 together form a butylene- (1,4), pentylene- (1,5) or 3-oxapentylene- (1,5) group, Y represents a methyl, ethyl, propyl, butyl, isobutyl group, phenyl or substituted phenyl, where the substituent or substituents attached to the phenyl group can be an alkyl, halogen, hydroxy, alkoxy, methylenedioxy, phenoxy, nitro and/or trifluoromethyl group and a, 1) R1 and R2 each represent hydrogen or b, 1) R1 represents hydrogen and R2 represents a straight or branched chain lower alkyl or alkenyl group or a phenyl group, n can only represent 2, 3 or 4, or respectively (4) if R4 and R5 represent methyl, ethyl, butyl, pentylene- (1,5) or 3-oxapentylene- (1,5), R1 represents hydrogen or a methyl group, R2 represents hydrogen or a phenyl group and Y represents methyl, ethyl, butyl, phenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl or trichlorophenyl, 2,5-dichlorophenoxy and n is 2, 3 or 4, or respectively (5) if Y represents a xanthenyl group and a, 1) R4, and R5 are identical and represent methyl, ethyl, propyl, isopropyl or butyl or b, 1) R4 and R5 together form a butylene- (1,4), pentylene- (1,5) or 3-oxapentylene- (1,5) group, R1 can only be methyl, ethyl, propyl, isopropyl, allyl, metallyl or phenylallyl and R2 can only be methyl, ethyl, propyl, isopropyl, allyl, metalyl, phenylallyl or phenyl, the process of which is characterized by reacting a secondary amine of general formula (IX) **(See formula)** where R4 and R5 have the meaning defined above, 4-p-chlorophenyl-tetrahydropyridine of formula (XI) **(See formula)** or 4-acetoxylidido-piperazine of formula (XII) **(See formula)** with a haloalcohol of general formula (VIII) where R1, R2 and n have the meanings defined above and Hal is halogen, and the amino alcohol obtained of general formula (XIII) **(See formula)** where R1, R2 and n have the meanings defined above and X is a group of formulas (III), (V) or (VI), it is reacted with a reactive derivative of a carboxylic acid of general formula (VII) **(See formula)** where Y has the meaning given above; and the compounds of general formula (II) are optionally converted into the corresponding free bases of general formula (I) or the bases of general formula (I) are optionally converted into their addition salts with acid or quaternary salts. (Machine-translation by Google Translate, not legally binding)
ES406345A 1971-09-03 1972-09-02 Aminoalcohol derivatives Expired ES406345A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HURI444A HU163608B (en) 1971-09-03 1971-09-03

Publications (1)

Publication Number Publication Date
ES406345A1 true ES406345A1 (en) 1976-01-16

Family

ID=11000874

Family Applications (1)

Application Number Title Priority Date Filing Date
ES406345A Expired ES406345A1 (en) 1971-09-03 1972-09-02 Aminoalcohol derivatives

Country Status (18)

Country Link
AT (1) AT323741B (en)
AU (1) AU4622172A (en)
BE (1) BE788289A (en)
CA (1) CA1008075A (en)
CH (1) CH577957A5 (en)
CS (1) CS168004B2 (en)
DD (1) DD102142A5 (en)
DE (2) DE2265580C2 (en)
DK (1) DK144821C (en)
ES (1) ES406345A1 (en)
FI (1) FI56007C (en)
GB (1) GB1407456A (en)
HU (1) HU163608B (en)
IL (1) IL40169A (en)
NL (1) NL179205C (en)
PL (1) PL90702B1 (en)
SU (1) SU631068A3 (en)
YU (1) YU35762B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004045220A1 (en) * 2004-09-17 2006-04-06 Riemser Arzneimittel Ag New medicines

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1445551A1 (en) 1964-12-10 1969-05-22 Boheringer Mannheim Gmbh Process for the preparation of new, basic substituted xanthene-9-o1-9-carboxylic acid esters and their salts
US3523950A (en) * 1967-12-13 1970-08-11 Robins Co Inc A H Certain 4 - phenyl - 1,2,3,6 - tetrahydropyridyl-n-lower alkylene-ureas and derivatives

Also Published As

Publication number Publication date
HU163608B (en) 1973-09-27
DE2243143A1 (en) 1973-04-12
NL179205C (en) 1986-08-01
DE2243143C3 (en) 1982-01-21
SU631068A3 (en) 1978-10-30
DK144821C (en) 1982-11-01
DE2265580C2 (en) 1982-11-18
NL179205B (en) 1986-03-03
CH577957A5 (en) 1976-07-30
BE788289A (en) 1973-01-02
FI56007B (en) 1979-07-31
AU4622172A (en) 1974-03-07
NL7211966A (en) 1973-03-06
PL90702B1 (en) 1977-01-31
IL40169A0 (en) 1972-10-29
GB1407456A (en) 1975-09-24
DD102142A5 (en) 1973-12-05
DE2243143B2 (en) 1980-10-09
YU35762B (en) 1981-06-30
AT323741B (en) 1975-07-25
CA1008075A (en) 1977-04-05
FI56007C (en) 1979-11-12
DK144821B (en) 1982-06-14
YU221172A (en) 1980-10-31
CS168004B2 (en) 1976-05-28
IL40169A (en) 1976-04-30

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