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US3717642A - N quinoline 5 aminooxazoles - Google Patents

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US3717642A
US3717642A US00151553A US3717642DA US3717642A US 3717642 A US3717642 A US 3717642A US 00151553 A US00151553 A US 00151553A US 3717642D A US3717642D A US 3717642DA US 3717642 A US3717642 A US 3717642A
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compounds
heteroaryl
quinoline
phenyl
aminooxazoles
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US00151553A
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Strandtmann M Von
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Warner Lambert Co LLC
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    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • 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
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 2
    • C07D277/82—Nitrogen atoms

Definitions

  • ABSTRACT The present invention is concerned with compounds of Formula 1:
  • R is heteroaryl and R is alkyl, aryl, or heteroaryl.
  • Compounds of this invention exhibit central nervous system depressant properties.
  • the present invention relates to N-heteroaryl 5- aminooxazoles having the following structural formula:
  • R is heteroaryl and R is lower alkyl, aryl, aralkyl, or heteroaryl.
  • heteroaryl encompasses the monocyclic and bicyclic hetero aromatic compounds having at least one hetero atom in the ring which may be either nitrogen, oxygen or sulfur.
  • Representative heteroaryl radicals falling within this definition are, for example, pyridine, quinoline, pyrrole, indole, thiophene, benzimidazole, tetrazole, pyrymidine and the like.
  • aryl denotes an aromatic radical, preferably of six to carbon atoms, such as for example, phenyl, tolyl and the like.
  • aralkyl encompasses lower alkyl groups in which an aryl group as defined above is substituted for a hydrogen atom, such as for example, benzyl, phenethyl and the like.
  • lower alkyl as used herein includes lower aliphatic hydrocarbons having one to five carbon atoms arranged in a straight carbon chain.
  • the compounds of this invention are useful in cases where a reduction in skeletal muscle spasm is indicated.
  • a reduction in body tone lasting for 24 hours.
  • the motor activity and temperature are also decreased for a period of about 3 to 6 hours.
  • a dose range from 100 to 500 mg/kg is recommended to produce the desired reduction in motor activity.
  • This dosage regimen may, of course, be varied according to body weight, sex, age, species of the mammal being treated as well as the severity of the condition being treated, by methods well known to the healing art.
  • these compounds are formulated with such standard pharmaceutical carriers, such as lactose, mannitol, dicalcium phosphate into dosage forms such as tablets, capsules and the like. They can also be combined with parenterally acceptable vehicles such as sesame oil, arachis oil and the like to form dosage forms suitable for parenteral injection.
  • standard pharmaceutical carriers such as lactose, mannitol, dicalcium phosphate
  • parenterally acceptable vehicles such as sesame oil, arachis oil and the like to form dosage forms suitable for parenteral injection.
  • compounds of Type I are prepared by acylation of heteroarylamines of Type III with azlactones of Type I] followed by cyclodehydration of the intermediate compounds of type IV.
  • the foregoing reaction is illustrated by the following schematic diagram:
  • R is quinolyl and R is lower alkyl, or phenol.
  • a compound according to claim 1 which is 2- [(phenyl-5 -oxazolyl)amine quinoline.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention is concerned with compounds of Formula I: wherein R1 is heteroaryl and R2 is alkyl, aryl, or heteroaryl. Compounds of this invention exhibit central nervous system depressant properties.

Description

United States Patent Von Strandtmann Feb. 20, 1973 [54] N QUINOLINE 5 AMINOOXAZOLES [75] Inventor: Maximilian Von Strandtmann,
Rockaway, NJ.
[73] Assignee: Warner-Lambert Company, Morris Plains, NJ.
[22] Filed: June 9, 1971 [21] Appl. No.: 151,553
Related US. Application Data [62] Division of Ser. No, 843,762, July 22, 1969, Pat. No.
[52] US. Cl. ..260/287 R, 260/288 R, 424/258 [51] Int. Cl. ..C07d 85/44 [58] Field of Search ..260/307 R, 287 R, 288 R [56] References Cited UNITED STATES PATENTS 2,456,911 12/1948 Bruce ..260/287 R 2,494,083 1/1950 Bruce ..260/287 R 3,054,794 9/1962 Shapiro ..260/287 R 3,376,307 4/1968 Hyoen et a1. ..260/287 3,509,170 4/1970 Lent ..260/307 R Primary Examiner-Donald G. Daus Attorney-Albert H. Graddis et al.
[57] ABSTRACT The present invention is concerned with compounds of Formula 1:
wherein R is heteroaryl and R is alkyl, aryl, or heteroaryl.
Compounds of this invention exhibit central nervous system depressant properties.
4 Claims, No Drawings N QUINOLINE AMINOOXAZOLES This application is a divisional application of my copending application U.S. Ser. No. 843,762, filed July 22, 1969 now U.S. Pat. No. 3,624,097 granted Nov. 30, 1971.
The present invention relates to N-heteroaryl 5- aminooxazoles having the following structural formula:
wherein R is heteroaryl and R is lower alkyl, aryl, aralkyl, or heteroaryl.
In the above definitions for R and R the term heteroaryl encompasses the monocyclic and bicyclic hetero aromatic compounds having at least one hetero atom in the ring which may be either nitrogen, oxygen or sulfur. Representative heteroaryl radicals falling within this definition are, for example, pyridine, quinoline, pyrrole, indole, thiophene, benzimidazole, tetrazole, pyrymidine and the like. The term aryl denotes an aromatic radical, preferably of six to carbon atoms, such as for example, phenyl, tolyl and the like. The term aralkyl encompasses lower alkyl groups in which an aryl group as defined above is substituted for a hydrogen atom, such as for example, benzyl, phenethyl and the like. The term lower alkyl as used herein includes lower aliphatic hydrocarbons having one to five carbon atoms arranged in a straight carbon chain.
The compounds of this invention are useful in cases where a reduction in skeletal muscle spasm is indicated. For example, at a dose of 200 mg/kg intraperitoneally in laboratory animals, such as rats, the compounds of this invention produce a reduction in body tone lasting for 24 hours. Simultaneously, the motor activity and temperature are also decreased for a period of about 3 to 6 hours. Generally speaking,a dose range from 100 to 500 mg/kg is recommended to produce the desired reduction in motor activity. This dosage regimen may, of course, be varied according to body weight, sex, age, species of the mammal being treated as well as the severity of the condition being treated, by methods well known to the healing art.
In order to use these compounds, they are formulated with such standard pharmaceutical carriers, such as lactose, mannitol, dicalcium phosphate into dosage forms such as tablets, capsules and the like. They can also be combined with parenterally acceptable vehicles such as sesame oil, arachis oil and the like to form dosage forms suitable for parenteral injection.
According to the present invention, compounds of Type I are prepared by acylation of heteroarylamines of Type III with azlactones of Type I] followed by cyclodehydration of the intermediate compounds of type IV. The foregoing reaction is illustrated by the following schematic diagram:
N 0 RlNlL nmricocmmioom [I III in which R, and R are as previously defined.
Starting compounds III are readily available from commercial sources, for example, Aldrich Chemical Co. Azlactones of type II were prepared by the procedure described in Organic Syntheses, Vol. 47, p. 101 (John Wiley & Sons, Inc., New York, New York, 1967).
The following examples are included in order further to illustrate the invention.
EXAMPLE 1 N-[ (2-Quinolylcarbamoyl)methyl]benzamide Is prepared in the same manner as N-[(2-pyridyl carbamoyl) methyl1benzamide using 1 g. 2-aminoquinoline, 1.1 g. 2-phenyl-5-oxazolone and THF. The product is recrystallized from absolute EtOI-I. M.P. 2l8-219; yield: 1.7 g. (8l percent).
Anal. Calcd. for C H N O C, 70.80; H, 4.95; N,
13.76. Found: C, 70.98; H,5.00; N, 13.95.
EXAMPLE 3 2-[(Phenyl-5-oxazolyl)amino1pyridine 5 g. N-[(2-pyridyl carbamoyl)methyl]benzamide is added to g. of PPE and stirred for 45 hrs. The solution is poured onto 300 ml. of ice and water with stirring and basified with ammonium hydroxide. The
3 4 precipitate is filtered, washed with water and is 190l92', yield: 2.7 g. (72 percent). recrystallized from abs. ethanol. M.P. l69-l70', yield: Anal. Calcd. for C H N O: C, 75.24; H, 4.56; N, 1.5 g. (32 percent). 14.63.
Anal. Calcd. for C H N O: C, 70.87; H, 4.67; N, Found;C,75.15;H,4.56;N, 14.60.
17.71. 5 lclaim: FOuHdi l. A compound of the formula:
EXAMPLE 4 l0 Rani-{:1
wherein R is quinolyl and R is lower alkyl, or phenol.
2. A compound according to claim 1 which is 2- [(phenyl-5 -oxazolyl)amine quinoline.
3. A compound of the formula:
R NHCOCH NHCOIQ 2-[(Phenyl-5-oxazolyl)aminelquinoline a IS P p in the Same m a n net as 2[ (phenyl s ox wherein R 18 qumolyl and R is lower alkyl or phenyl.
azoiynaminemyridine using 3.7 g. of N [(2'quinoly1 A compound according to clairn 3 which is N-[(2- carbamoyl)methyl1benzamide and 75 g. of PPE. The qummylcarbamoynmethylwenzamlde' product is recrystallized from ethyl acetate. M.P.

Claims (3)

1. A compound of the formula: wherein R1 is quinolyl and R2 is lower alkyl, or phenol.
2. A compound according to claim 1 which is 2-((phenyl-5-oxazolyl)amine)quinoline.
3. A compound of the formula: R1NHCOCH2NHCOR2 wherein R1 is quinolyl and R2 is lower alkyl or phenyl.
US00151553A 1969-07-22 1971-06-09 N quinoline 5 aminooxazoles Expired - Lifetime US3717642A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060148841A1 (en) * 2004-02-26 2006-07-06 Lundeen James E Pharmaceutical composition comprising combination of non-alkaloid and alkaloid-based component for treating skeletal muscle spasm
CN112153984A (en) * 2018-01-30 2020-12-29 福宏治疗公司 Compounds and their uses
US11485732B2 (en) 2020-01-29 2022-11-01 Foghorn Therapeutics Inc. Compounds and uses thereof
US12282014B2 (en) 2015-11-19 2025-04-22 Dana-Farber Cancer Institute, Inc. Methods of identifying compounds that interfere with ERG-driven misguidance of BAF complexes in TMPRSS2-ERG driven prostate cancers
US12384776B2 (en) 2019-01-29 2025-08-12 Foghorn Therapeutics Inc. Compounds and uses thereof
US12383555B2 (en) 2020-05-20 2025-08-12 Foghorn Therapeutics Inc. Methods of treating cancers
US12473334B2 (en) 2018-10-17 2025-11-18 Dana-Farber Cancer Institute, Inc. SWI/SNF family chromatin remodeling complexes and uses thereof
US12509453B2 (en) 2020-01-29 2025-12-30 Foghorn Therapeutics Inc. BRM/BRG1 inhibitors and uses thereof

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* Cited by examiner, † Cited by third party
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FR2567887B1 (en) * 1984-07-19 1986-12-19 Rhone Poulenc Sante NEW SUBSTITUTED AMIDES, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
US5073565A (en) * 1990-04-27 1991-12-17 Warner-Lambert Company Tetrazole ureas and thioureas and their use as acat inhibitors
DK0600950T3 (en) * 1991-08-22 1997-04-21 Warner Lambert Co Tetrazolamides as Inhibitors of ACAT
US5677321A (en) * 1996-02-29 1997-10-14 Synaptic Pharmaceutical Corporation 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands

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US2362337A (en) * 1942-07-31 1944-11-07 American Cyanamid Co Process of making 2-aminooxazole
US2456911A (en) * 1945-05-04 1948-12-21 Wyeth Corp Disubstituted acetamidyl derivatives of amino quinolines
US2494083A (en) * 1945-04-17 1950-01-10 Wyeth Corp Disubstituted glycyl derivatives of amino quinolines
US3054794A (en) * 1958-01-17 1962-09-18 Us Vitamin Pharm Corp Process for preparing 3-(aminoalkyl)-oxazolidine-2, 4-diones
US3376307A (en) * 1964-10-29 1968-04-02 Nepera Chemical Co Inc Amino esters of (2, 3 or 4) pyridyl carbamic acid
US3401173A (en) * 1966-04-05 1968-09-10 Smith Kline French Lab Heterocyclic acylaminobenzimidazoles
US3509170A (en) * 1967-06-12 1970-04-28 Du Pont Heterocyclic amino-oxazolines
US3578671A (en) * 1967-11-06 1971-05-11 Wyeth John & Brother Ltd Oxazoles

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NL131194C (en) * 1963-07-19

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2362337A (en) * 1942-07-31 1944-11-07 American Cyanamid Co Process of making 2-aminooxazole
US2494083A (en) * 1945-04-17 1950-01-10 Wyeth Corp Disubstituted glycyl derivatives of amino quinolines
US2456911A (en) * 1945-05-04 1948-12-21 Wyeth Corp Disubstituted acetamidyl derivatives of amino quinolines
US3054794A (en) * 1958-01-17 1962-09-18 Us Vitamin Pharm Corp Process for preparing 3-(aminoalkyl)-oxazolidine-2, 4-diones
US3376307A (en) * 1964-10-29 1968-04-02 Nepera Chemical Co Inc Amino esters of (2, 3 or 4) pyridyl carbamic acid
US3401173A (en) * 1966-04-05 1968-09-10 Smith Kline French Lab Heterocyclic acylaminobenzimidazoles
US3509170A (en) * 1967-06-12 1970-04-28 Du Pont Heterocyclic amino-oxazolines
US3511851A (en) * 1967-06-12 1970-05-12 Du Pont Heterocyclic amino-oxazolines
US3578671A (en) * 1967-11-06 1971-05-11 Wyeth John & Brother Ltd Oxazoles

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060148841A1 (en) * 2004-02-26 2006-07-06 Lundeen James E Pharmaceutical composition comprising combination of non-alkaloid and alkaloid-based component for treating skeletal muscle spasm
US12282014B2 (en) 2015-11-19 2025-04-22 Dana-Farber Cancer Institute, Inc. Methods of identifying compounds that interfere with ERG-driven misguidance of BAF complexes in TMPRSS2-ERG driven prostate cancers
CN112153984A (en) * 2018-01-30 2020-12-29 福宏治疗公司 Compounds and their uses
JP2021512166A (en) * 2018-01-30 2021-05-13 フォグホーン セラピューティクス インコーポレイテッドＦｏｇｈｏｒｎ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． Compounds and their use
US11497752B2 (en) 2018-01-30 2022-11-15 Foghorn Therapeutics Inc. Compounds and uses thereof
US12383560B2 (en) 2018-01-30 2025-08-12 Foghorn Therapeutics Inc. Compounds and uses thereof
US12473334B2 (en) 2018-10-17 2025-11-18 Dana-Farber Cancer Institute, Inc. SWI/SNF family chromatin remodeling complexes and uses thereof
US12384776B2 (en) 2019-01-29 2025-08-12 Foghorn Therapeutics Inc. Compounds and uses thereof
US11485732B2 (en) 2020-01-29 2022-11-01 Foghorn Therapeutics Inc. Compounds and uses thereof
US12486262B2 (en) 2020-01-29 2025-12-02 Foghorn Therapeutics Inc. Compounds and uses thereof
US12509453B2 (en) 2020-01-29 2025-12-30 Foghorn Therapeutics Inc. BRM/BRG1 inhibitors and uses thereof
US12383555B2 (en) 2020-05-20 2025-08-12 Foghorn Therapeutics Inc. Methods of treating cancers

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