GB1125559A - Novel urea derivatives and their production - Google Patents

Novel urea derivatives and their production

Info

Publication number
GB1125559A
GB1125559A GB51522/66A GB5152266A GB1125559A GB 1125559 A GB1125559 A GB 1125559A GB 51522/66 A GB51522/66 A GB 51522/66A GB 5152266 A GB5152266 A GB 5152266A GB 1125559 A GB1125559 A GB 1125559A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
splitting
hydrolysis
amine
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
GB51522/66A
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.)
Novartis AG
Original Assignee
JR 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
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1125559A publication Critical patent/GB1125559A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,125,559. Urea and thiourea derivatives; adamantanes. J. R. GEIGY A.G. 17 Nov., 1966 [18 Nov., 1965], No. 51522/66. Heading C2C. Novel compounds of Formula I wherein X represents a methylene, ethylene' imino or C 1-2 alkylimino or alkanoylimino group, or oxygen, Y represents oxygen or sulphur, R 1 , R 2 and R5 represent hydrogen or a C 1-4 alkyl group, R 3 and R 4 represent hydrogen, halogen up to the atomic number 35, trifluoromethyl, or C 1-4 low alkyl or alkoxy or C 1-2 alkanoyl groups, and n represents 0 or 1, are prepared (1) by reacting an amine of Formula II wherein X<SP>1</SP> has the meaning given for X above with the exception of the imino group, with a suitable phenyl isocyanate or isothiocyanate or with a reactive functional derivative of a suitable carbanilic acid or thiocarbanilic acid, and, if desired, splitting off any low alkanoyl radical in X<SP>1</SP> by hydrolysis, (2) by reacting an isocyanate or isothiocyanate of Formula VI or a reactive functional derivative of a carbamic acid or thiocarbamic acid of Formula VII with a suitable aniline, and, if desired, splitting off any low alkanoyl radical in X<SP>1</SP> by hydrolysis, (3) by reacting a compound of Formula VIII with a compound of formula H 2 Y, and, if desired, splitting off any low alkanoyl radical in X<SP>1</SP> by hydrolysis, or (4) by converting a thiourea obtained as described above into the corresponding urea. 2-Oxa - adamantane - 1 - amine may be prepared by reacting bicyclo[3,3,1]nonan-3,7-dione with benzylamine, reducing the 3-benzylamino- 2 - oxaadamantan - 1 - ol obtained with lithium aluminium hydride, and debenzylating the N - benzyl - 2 - oxaadamantane - 1 - amine thus formed. 1 - (1 - Adamantyl) - 3 - (3,4 - dichlorophenyl)- carbodiimide may be obtained by treating 1-(1- adamantyl) - 3 - (3,4 - dichlorophenyl) - thiourea with anhydrous magnesium sulphate and lead oxide. Therapeutic compositions having anti-bacterial activity, which may be administered locally, parenterally or orally, contain as active ingredient a compound of Formula I above.
GB51522/66A 1965-11-18 1966-11-17 Novel urea derivatives and their production Expired GB1125559A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1590965A CH456570A (en) 1965-11-18 1965-11-18 Process for the production of new substituted urea derivatives

Publications (1)

Publication Number Publication Date
GB1125559A true GB1125559A (en) 1968-08-28

Family

ID=4412947

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51522/66A Expired GB1125559A (en) 1965-11-18 1966-11-17 Novel urea derivatives and their production

Country Status (10)

Country Link
AT (2) AT267543B (en)
BE (1) BE689823A (en)
CH (1) CH456570A (en)
DE (1) DE1246722B (en)
ES (4) ES333485A1 (en)
FR (2) FR1504098A (en)
GB (1) GB1125559A (en)
NL (1) NL6616214A (en)
NO (1) NO119270B (en)
SE (1) SE325024B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005009391A2 (en) 2003-07-24 2005-02-03 Merck & Co., Inc. Antibiotic compound
WO2010112946A1 (en) 2009-03-31 2010-10-07 Rudjer Boskovic Institute Adamantane bisurea derivatives, method of preparation and application in anion sensing
WO2017017048A1 (en) * 2015-07-28 2017-02-02 Universitat De Barcelona Analogs of adamantylureas as soluble epoxide hydrolase inhibitors

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3621100A (en) * 1965-11-18 1971-11-16 Geigy Chem Corp Composition and method for producing a tuberculostatic effect
US3615941A (en) * 1968-05-07 1971-10-26 Hitachi Ltd Method for manufacturing semiconductor device with passivation film
BE758165A (en) * 1969-10-28 1971-04-28 Cilag Chemie ADAMANTYLURIDES AND METHODS FOR PREPARING THEM
ATE61574T1 (en) * 1987-07-02 1991-03-15 Warner Lambert Co N-((2,6-DISUBSTITUTED)-PHENYL>-UREA AND - CARBAMATE INHIBITORS OF ACYL-COENZYME A:CHOLESTEROL ACYLTRANSFERASE.

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005009391A2 (en) 2003-07-24 2005-02-03 Merck & Co., Inc. Antibiotic compound
EP1651628A2 (en) * 2003-07-24 2006-05-03 Merck &amp; Co., Inc. (a New Jersey corp.) Antibiotic compound
EP1651628A4 (en) * 2003-07-24 2008-07-16 Merck & Co Inc Antibiotic compound
WO2010112946A1 (en) 2009-03-31 2010-10-07 Rudjer Boskovic Institute Adamantane bisurea derivatives, method of preparation and application in anion sensing
WO2017017048A1 (en) * 2015-07-28 2017-02-02 Universitat De Barcelona Analogs of adamantylureas as soluble epoxide hydrolase inhibitors

Also Published As

Publication number Publication date
ES333487A1 (en) 1967-12-01
CH456570A (en) 1968-07-31
NO119270B (en) 1970-04-27
DE1246722B (en) 1967-08-10
ES333486A1 (en) 1968-01-01
NL6616214A (en) 1967-05-19
SE325024B (en) 1970-06-22
ES333485A1 (en) 1967-12-01
FR1504098A (en) 1967-12-01
FR6433M (en) 1968-11-04
AT267543B (en) 1969-01-10
BE689823A (en) 1967-05-17
ES333484A1 (en) 1967-12-01
AT267540B (en) 1969-01-10

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