GB1368699A - Benzoyl ureas and process for their manufacture - Google Patents

Benzoyl ureas and process for their manufacture

Info

Publication number
GB1368699A
GB1368699A GB2956372A GB2956372A GB1368699A GB 1368699 A GB1368699 A GB 1368699A GB 2956372 A GB2956372 A GB 2956372A GB 2956372 A GB2956372 A GB 2956372A GB 1368699 A GB1368699 A GB 1368699A
Authority
GB
United Kingdom
Prior art keywords
urea
substituted
benzoyl
tolyl
propyl
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
GB2956372A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1368699A publication Critical patent/GB1368699A/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
    • C07D295/12—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
    • C07D295/125—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 with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

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

Abstract

1368699 Benzoyl ureas FARBWERK HOECHST AG 23 June 1972 [23 June 1971] 29563/72 Heading C2C Novel compounds (I) and their salts in which R 1 represents one or more substituents selected from hydrogen, halogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-7 cycloalkyl, C 4-7 cycloalkenyl, aralkyl (having 1 to 4 C atoms in the alkyl moiety), phenyl, hydroxyl, acyloxy C 1-6 alkoxy, C 3-6 alkenyloxy, aralkoxy or araloxyalkoxy (having 1 to 4 C atoms in the alkyl moiety), aryloxy, trifluoromethyl and nitro and wherein two adjacent substituents R 1 may form a carbocyclic ring having 5 to 7 ring members or an alkylene-dioxy group, R 2 represents one or more substituents selected from hydrogen, halogen, C 1-4 alkyl and C 1-4 alkoxy and A is a C 2-6 alkylene radical are prepared by (1) reaction of an R 1 substituted benzoyl-isocyanate, -carbamate, -carbamoyl halide, -thiocarbamate, -urea, -semicarbazide, or -semicarbazone with an amine of Formula II (2) an R 1 substituted benzamide is reacted with an isocyanate, carbamate, thiocarbamate, carbamoyl halide or urea each substituted by a group of Formula V (3) a correspondingly substituted benzoylisourea ether or ester, benzoyl-isothiourea ether, benzoyl-parabanic acid or benzoylhaloformic acid amidine is hydrolysed; (4) water is added to a correspondingly substituted benzoylcarbodi-imide; (5) a correspondingly substituted benzoyl-thiourea, thiobenzoyl urea or thiobenzoyl-thiourea is treated with a heavy metal oxide, heavy metal salt or an oxidizing agent to replace the sulphur atom by an oxygen atom; (6) an R 1 substituted benzoic acid or halide ester or anhydride thereof is reacted with a urea substituted by the group of Formula (V); (7) a compound IV is reacted with a piperazine VII (8) a compound VI in which B represents a radical of Formula VIII is reacted with R 2 substituted aniline; (9) a compound VI in which B is an R 2 substituted phenyl group, preferably in the form of its reactive ester is reacted with an amine of Formula IX Preferred compounds are N-(4-methoxy-benzoyl)- N<SP>1</SP> - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea; N - (5 - chloro - 2 - methoxy - benzoyl) - N<SP>1</SP>- [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea and its hydrochloride; N-(3,4-methylenedioxy - benzoyl) - N<SP>1</SP> - [3 - (4 - m - tolyl - piperazine- 1-yl)-propyl] urea dihydrochloride; N-(2,5-dimethylbenzoyl) - N<SP>1</SP> - [3 - (4 - m - tolyl - piperazin- 1 - yl) - propyl] urea; N - (1 - naphthoyl) - N<SP>1</SP>- [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea; N - (5,6,7,8 - tetrahydro - 1 - naphthoyl)- N<SP>1</SP> - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea. Compounds I are tranquillizers and form with a suitable carrier a pharmaceutical preparation which may be administered orally or parenterally.
GB2956372A 1971-06-23 1972-06-23 Benzoyl ureas and process for their manufacture Expired GB1368699A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712131034 DE2131034A1 (en) 1971-06-23 1971-06-23 ACYLIC URNANE AND METHOD FOR MANUFACTURING IT

Publications (1)

Publication Number Publication Date
GB1368699A true GB1368699A (en) 1974-10-02

Family

ID=5811500

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2956372A Expired GB1368699A (en) 1971-06-23 1972-06-23 Benzoyl ureas and process for their manufacture

Country Status (12)

Country Link
US (1) US3823144A (en)
AR (2) AR194693A1 (en)
AU (1) AU461846B2 (en)
BE (1) BE785378A (en)
DD (1) DD101401A5 (en)
DE (1) DE2131034A1 (en)
FR (1) FR2143361B1 (en)
GB (1) GB1368699A (en)
HU (1) HU165554B (en)
IL (1) IL39727A0 (en)
NL (1) NL7208259A (en)
ZA (1) ZA724294B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES472295A1 (en) * 1978-08-02 1979-02-16 Invest Tecnica Aplicada New acylureas with pharmaceutical activity, the process for their preparation, and pharmaceutical compositions which contain them.
HU184062B (en) * 1979-10-19 1984-06-28 Chinoin Gyogyszer Es Vegyeszet Process for producing substituted acyl urea
US4666911A (en) * 1981-07-14 1987-05-19 Taiho Pharmaceutical Company Limited Allophanoylpiperazine compound and analgesic composition containing same as active ingredient
US4529819A (en) * 1982-08-02 1985-07-16 The Dow Chemical Company Method for making benzoylphenylureas
GB8500615D0 (en) * 1985-01-10 1985-02-13 Lundbeck & Co As H Organic compounds
ES2023217B3 (en) * 1986-08-04 1992-01-01 Sandoz Ag DERIVATIVES OF BENZOHIDROXAMICO ACID.
US6670364B2 (en) * 2001-01-31 2003-12-30 Telik, Inc. Antagonists of MCP-1 function and methods of use thereof
US6962926B2 (en) * 2001-01-31 2005-11-08 Telik, Inc. Antagonist of MCP-1 function, and compositions and methods of use thereof
TWI245761B (en) * 2001-03-01 2005-12-21 Telik Inc Antagonists of MCP-1 function and methods of use thereof
TWI236474B (en) * 2001-04-03 2005-07-21 Telik Inc Antagonists of MCP-1 function and methods of use thereof

Also Published As

Publication number Publication date
DD101401A5 (en) 1973-11-05
BE785378A (en) 1972-12-27
AR194693A1 (en) 1973-07-31
DE2131034A1 (en) 1973-01-11
US3823144A (en) 1974-07-09
IL39727A0 (en) 1972-08-30
AR194692A1 (en) 1973-07-31
HU165554B (en) 1974-09-28
NL7208259A (en) 1972-12-28
AU4366072A (en) 1974-01-03
FR2143361B1 (en) 1975-06-20
AU461846B2 (en) 1975-06-05
FR2143361A1 (en) 1973-02-02
ZA724294B (en) 1973-03-28

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees