GB1414048A - Pyrrolidylidene piperidylidene and hexahydroazepinylidene ureas - Google Patents

Pyrrolidylidene piperidylidene and hexahydroazepinylidene ureas

Info

Publication number
GB1414048A
GB1414048A GB1259773A GB1259773A GB1414048A GB 1414048 A GB1414048 A GB 1414048A GB 1259773 A GB1259773 A GB 1259773A GB 1259773 A GB1259773 A GB 1259773A GB 1414048 A GB1414048 A GB 1414048A
Authority
GB
United Kingdom
Prior art keywords
alkyl
phenyl
prepared
compound
benzyloxy
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
GB1259773A
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.)
Janssen Pharmaceuticals Inc
Original Assignee
McNeilab Inc
McNeil Laboratories Inc
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 McNeilab Inc, McNeil Laboratories Inc filed Critical McNeilab Inc
Publication of GB1414048A publication Critical patent/GB1414048A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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
    • 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
    • C07D211/72—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 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1414048 Pyrrolidylidene; piperidylidene and hexahydroazepenylidene ureas McNEIL LABORATORIES Inc 15 March 1973 [17 March 1972] 12597/73 Heading C2C Novel compounds (I) in which n is 1 to 3, R and R 2 are hydrogen or C 1-5 alkyl R 1 is C 1-5 alkyl or benzyl. Ar is naphthyl, phenyl mono-, di or tri-halophenyl, mono, di or tri, C 1-5 alkylphenyl, mono-, di- or tri- C 1-5 alkoxy-phenyl, mono- or ditrifluoromethylphenyl nitro-phenyl cyanophenyl methylthiophenyl, C 1-5 alkylcarboxyl-phenyl, benzyloxy - phenyl halo - C 1-5 alkyl - phenyl halo - C 1-5 alkoxyphenyl, halobenzyloxyphenyl, halo-trifluoromethylphenyl or halonitrophenyl; provided that when n is 2 or 3. R is hydrogen and R 1 is C 1-5 alkyl and their acid addition salts are prepared by reacting an imino compound (II) with [1] an isocyanate (III) Ar-N=C=O to form a compound I in which R 2 is hydrogen or (2 ) with a carbamoylhalide (IV ) Cl-CO-NR 2 Ar in which R 2 is C 1-5 alkyl to form a compound I in which R 2 is C 1-5 alkyl. Compounds II are prepared from a compound (VI) in which n is 1 or 2 by reaction with triethoxyoxonium fluoroborate and ammonia to form the fluoroborate salt of a compound II which is converted to other salts and the required free base. The carbamoyl chlorides (IV) are prepared from the appropriate aniline by treatment with excess phosgene. m-Acetylphenylisocyanate and m - methylthiophenylisocyanate are prepared from m-(acetyl or methyl thio) aniline by reaction with phosgene. 4- Benzyloxy - 3 - chloro - phenylisocyanate is prepared from ethyl-4-benzyloxy-3-chlorobenzoate by reaction with hydrazine to form the corresponding hydrazide which on treatment with hydrochloric acid and sodium nitrite gives 4- benzyloxy-3 -chlorobenzoylazide which rearranges on heating to the isocyanate. Compounds I show CNS depressant activity and form with a diluent or carrier a pharmaceutical composition which may be administered orally or parenterally.
GB1259773A 1972-03-17 1973-03-15 Pyrrolidylidene piperidylidene and hexahydroazepinylidene ureas Expired GB1414048A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23581672A 1972-03-17 1972-03-17
US33584573A 1973-02-26 1973-02-26

Publications (1)

Publication Number Publication Date
GB1414048A true GB1414048A (en) 1975-11-12

Family

ID=26929245

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1259773A Expired GB1414048A (en) 1972-03-17 1973-03-15 Pyrrolidylidene piperidylidene and hexahydroazepinylidene ureas

Country Status (12)

Country Link
AT (2) AT323191B (en)
CA (1) CA950464A (en)
CH (1) CH578539A5 (en)
CS (2) CS179412B2 (en)
DE (1) DE2313257A1 (en)
DK (1) DK136715B (en)
FI (1) FI56831C (en)
FR (1) FR2181826B1 (en)
GB (1) GB1414048A (en)
IL (1) IL41798A (en)
NL (1) NL7303723A (en)
NO (1) NO140136C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ183570A (en) * 1976-03-19 1979-06-08 Mcneilab Inc Heterocyclic guanidine derivatives, having anti-secretory and hypogliycaemic activity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3717648A (en) * 1970-10-21 1973-02-20 Sterling Drug Inc 1-phenyl-azacarbocyclic-2-imines

Also Published As

Publication number Publication date
CH578539A5 (en) 1976-08-13
CS179412B2 (en) 1977-10-31
DK136715C (en) 1978-04-24
DE2313257A1 (en) 1973-10-04
FR2181826A1 (en) 1973-12-07
FI56831B (en) 1979-12-31
IL41798A (en) 1976-04-30
AT323194B (en) 1975-06-25
IL41798A0 (en) 1973-05-31
CA950464A (en) 1974-07-02
NO140136C (en) 1979-07-11
NO140136B (en) 1979-04-02
AT323191B (en) 1975-06-25
FI56831C (en) 1980-04-10
DK136715B (en) 1977-11-14
FR2181826B1 (en) 1976-04-09
CS179444B2 (en) 1977-10-31
NL7303723A (en) 1973-09-19

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee