GB1287317A - Novel adamantylurea derivatives and a process for the preparation thereof - Google Patents

Novel adamantylurea derivatives and a process for the preparation thereof

Info

Publication number
GB1287317A
GB1287317A GB5049070A GB5049070A GB1287317A GB 1287317 A GB1287317 A GB 1287317A GB 5049070 A GB5049070 A GB 5049070A GB 5049070 A GB5049070 A GB 5049070A GB 1287317 A GB1287317 A GB 1287317A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
adamantyl
alkyl
reacting
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
GB5049070A
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.)
Cilag Chemie Ltd
Original Assignee
Cilag Chemie Ltd
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 Cilag Chemie Ltd filed Critical Cilag Chemie Ltd
Publication of GB1287317A publication Critical patent/GB1287317A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • 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
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Abstract

1287317 Adamantylurea derivatives CILAG CHEMIE AG 23 Out 1970 [28 Oct 1969 2 Sept 1970] 50490170 Heading C2C The invention comprises adamantylurea derivatives of the Formula Ib wherein R 1 and R 2 each are H or C 1-12 alkyl; Alk is C 1-10 alkylene; R 3 is H, C 1-12 alkyl, di- (C 1-5 alkyl) amino-C 1-5 alkyl, benzyl, 4-(N- methyl)piperidyl, or a group of the formula R<SP>1</SP>-(O-R<SP>11</SP>) n -R<SP>111</SP>-, in which R<SP>1</SP> is CH 3 or CH 2 CH 3 , R<SP>11</SP> and R<SP>111</SP> each are -CH 2 - or -CH 2 -CH 2 -, and n is 0 to 3; provided that when one of R 1 or R 2 is an alkyl group of more than 5 carbon atoms, then the other group is H or C 1-5 alkyl, Alk is CH 2 and R 3 is C 1-5 alkyl, the therapeutically active acid addition salts of the foregoing compounds which contain a basic nitrogen, and N - (1 - adamantyl) - N<SP>1</SP> - (ethoxycarbonyl)-urea. The latter compound is prepared by reacting ethoxycarbonyl isocyanate with 1-amino adamantane in an anhydrous organic solvent. Compounds of Formula Ib above may be obtained by one of the following methods: (a) reacting 1-adamantane isocyanate with compounds of the formula (b) reacting the appropriate aminoadamantanes with compounds of the formula (R 3 is not equal to H) in anhydrous organic solvents; (c) reacting the appropriate compound of the formula AdN(R 1 )COCl (Ad is 1-adamantyl) with compounds of the formula HNR 2 -Alk COOR 3 (R 3 is not H) in anhydrous organic solvents; (d) reacting the appropriate aminadamantanes with compounds of the formula ClOC-NR 2 -Alk COOR 3 (R 3 is not H) in anhydrous organic solvents, and, if desired, esterifying the compounds thus obtained in which R 3 is H, or hydrolysing the compounds thus obtained wherein R 3 is other than H. The following intermediates and starting materials are prepared: N - (1 - Adamantyl) - N - ethylcarbamoyl chloride, N - (1 - adamantyl) - N - methylcarbamoyl chloride, N - (ethoxycarbonylmethyl)-N- methylcarbamoyl chloride, N - (1 - adamantyl)-N- propyicarhamoyl chloride, N - (1 - adamantyl)- N - octylcarbamoyl chloride, N - (1 - adamantyl) - N<SP>1</SP> - (chlorocarbonylmethyl) urea, N - ( 1 - adaman - tyl) - N - (α - chlorocarbonylethyl) urea, 1-octanoylaminoadamantane, 1 - (octylamino) adamantane, pentylaminoacetonitrile, pentylaminoacetic acid hydrochloride, ethyl pentylaminoacetate, ethyl octylaminoacetate, 1 - (sec.- butylamino) adamantane, 3,6 - diazaheptyl isocyantoacetate, 3,6,9,12- tetraoxa - trideconyl isocyanatoacetate and 2-dimethylaminoethyl isocyantoacetate hydrochloride. Pharmaceutical compositions have anti-viral activity, contain the above novel adamantane derivatives and pharmaceutically acceptable carriers.
GB5049070A 1969-10-28 1970-10-23 Novel adamantylurea derivatives and a process for the preparation thereof Expired GB1287317A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US87408469A 1969-10-28 1969-10-28
US6915070A 1970-09-02 1970-09-02

Publications (1)

Publication Number Publication Date
GB1287317A true GB1287317A (en) 1972-08-31

Family

ID=26749738

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5049070A Expired GB1287317A (en) 1969-10-28 1970-10-23 Novel adamantylurea derivatives and a process for the preparation thereof

Country Status (9)

Country Link
AT (1) AT302348B (en)
BE (1) BE758165A (en)
CH (1) CH543487A (en)
DE (1) DE2052256A1 (en)
ES (1) ES384946A1 (en)
FR (1) FR2070171B1 (en)
GB (1) GB1287317A (en)
NL (1) NL7015825A (en)
SE (1) SE356044B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090326039A1 (en) * 2003-04-03 2009-12-31 The Regents Of The University Of California Inhibitors for the soluble epoxide hydrolase
WO2010112946A1 (en) 2009-03-31 2010-10-07 Rudjer Boskovic Institute Adamantane bisurea derivatives, method of preparation and application in anion sensing
US8513302B2 (en) 2003-04-03 2013-08-20 The Regents Of The University Of California Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002507591A (en) * 1998-03-26 2002-03-12 ユニバーシティ オブ サスカチワン テクノロジーズ インコーポレイテッド Aliphatic aminocarboxylic acids and aminophosphonic acids, aminonitrile and aminotetrazole as cell rescue agents
US6984754B1 (en) 1998-03-26 2006-01-10 University Of Saskatchewan Technologies Inc. Aliphatic amino carboxylic and amino phosphonic acids amino nitriles and amino tetrazoles as cellular rescue agents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH456570A (en) * 1965-11-18 1968-07-31 Geigy Ag J R Process for the production of new substituted urea derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090326039A1 (en) * 2003-04-03 2009-12-31 The Regents Of The University Of California Inhibitors for the soluble epoxide hydrolase
US8455652B2 (en) * 2003-04-03 2013-06-04 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Inhibitors for the soluble epoxide hydrolase
US8513302B2 (en) 2003-04-03 2013-08-20 The Regents Of The University Of California Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids
WO2010112946A1 (en) 2009-03-31 2010-10-07 Rudjer Boskovic Institute Adamantane bisurea derivatives, method of preparation and application in anion sensing

Also Published As

Publication number Publication date
DE2052256A1 (en) 1971-05-06
AT302348B (en) 1972-10-10
ES384946A1 (en) 1973-09-01
NL7015825A (en) 1971-05-03
FR2070171A1 (en) 1971-09-10
CH543487A (en) 1973-10-31
BE758165A (en) 1971-04-28
SE356044B (en) 1973-05-14
FR2070171B1 (en) 1975-04-18

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee