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US4873346A Expired / Lapsed US ⏱️ 0.0 years remaining

Substituted benzothiazoles, benzimidazoles, and benzoxazoles

Assignee: Pharmacia and Upjohn Co

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Filing: 1985-09-20

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Granted: 1989-10-10

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Expires: 2005-09-20

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Abstract

Abstract The present invention provides certain novel substituted benzothiazoles, benzimidazoles and benzoxazoles which are useful as inhibitors of leukotriene biosynthesis and/or as inhibitors of the action of lipoxygenase and/or as inhibitors of mucus secretion in mammalian metabolism. They are thus employed wherever it is medically necessary or desirable to inhibit these systems.

Inventors

👤 David J. Anderson

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-11-08 01:45

CPC Classifications

C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/28; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74; C07D277/82; C07D417/00; C07D417/02; C07D417/12

Claims Analysis

Total Claims: 7

Claim 1

Independent Claim 154 words

A compound according to the structural formula wherein A, B, C and D are independently hydrogen or hydroxy provided that they are all not hydrogen; X is O, S or NH; and Z is (1) exo or endo 2-norbornyl, (2) 1-adamantyl, (3) 3-cyclohexenyl, (4) 2-cyclohexanolyl, (5) 2-cyclohexanone, (6) Cl, (7) Br, (8) CN, (9) OCOCH 3 , (10) COOCH 3 , (11) C.tbd.CH, (12) CH═CH 2 , (13) CH═CH(C 1 -C 4 )alkyl, (14) CH═CH-phenyl, (15) CH(Br)CH 3 , (16) CH(CH 3 )phenyl, (17) CH(CH 3 ) p -tolyl, (18) phenyl unsubstituted or substituted at the 4 position with bromine or COOCH 3 ; (19) benzoyl, (20) toluyl, (21) 2-naphthyl, (22) 9-anthracenyl, (23) 2-tetrahydrofuranyl, (24) phthalimido, (25) 2-benzimidazolyl, (26) 2-mercapto-6-hydroxybenzothiazolyl, or (27) 7-methoxy-coumarin-4-yl; and pharmaceutically acceptable salts thereof; wherein n is 4-11, except when Z is: (a) exo or endo 2-norbornyl, (b) 1-adamantyl, (c) 3-cyclohexenyl, (d) 2-cyclohexanolyl, or (e) 2-cyclohexanone; then n is 0.

Claim 2

Dependent Claim 154 words

Claim 3

Dependent Claim 47 words

The compound of claim 1 according to the structural formula: ##STR4## wherein A, B and D are hydrogen; C is hydroxy; X is (1) S, or (2) NH; n is 4-11; Z is (1) CH═CH 2 , or (2) COOCH 3 ; and pharmaceutically acceptable salts thereof.

Claim 4

Dependent Claim 58 words

A compound according to claim 1 wherein the compound is: Hexanoic acid, 6-[(6-hydroxy-2-benzothiazolyl)thio]-, methyl ester; Hexanenitrile, 6-[(6-hydroxy-2-benzothiazolyl)thio]-; 6-Benzothiazolol, 2-(5-hexenylthio)-; 6-Benzothiazolol, 2-(bicyclo[2.2.1]hept-2-ylthio)-; 6-Benzothiazolol, 2-[(2-hydroxycyclohexyl)thio]-; 4-Benzothiazolol, 2-(5-hexenylthio)-; Hexanoic acid, 6-[(4-hydroxy-2-benzothiazolyl)thio]-, methyl ester; 6-Benzothiazolol, 2-[(6-bromohexyl)thio]-; Pentanol, 5-[(6-hydroxybenzothiazol-2-yl)thio]-acetate-; Benzothiazole-6-ol, 2-[(2-oxocyclohexyl)thio]-; 6-Benzothiazolol, 2-(b 2-cyclohexenylthio)-; 2-[6-[(6-Hydroxy-2-benzothiazolyl)thio]hexyl]-1H-Isoindole-1,3(2H)dione; 6-[(6-Hydroxy-2-benzothiazolyl)amino]hexanoic acid methyl ester; 2-[(5-Bromohexyl)amino]-6-benzothiazolol; 2-[[5-(4-Methylphenyl)hexyl]amino]-6-benzothiazolol; 2-(b 5-Hexenylamino)-6-benzothiazolol; 2-(5-Hexenylamino)-6-benzothiazolol maleic acid salt; 6-Benzothiazolol, 2-[(6-chlorohexyl)thio]-2-(Tricyclo[3.3.1.1.3,7]dec-1-ylamino)-6-benzothiazolol; 6-[(6-Hydroxy-2-benzothiazolyl)amino]-1-(4-methylphenyl)-1-hexanone; Endo-2-(bicyclo[2.2.1]hept-2-ylamino)-6-benzothiazolol; 2-(5-Hexenyloxy)-6-benzothiazolol; or.

Claim 5

Dependent Claim 26 words

A compound according to claim 2 wherein the compound is: Hexanoic acid, 6-[(6-hydroxy-2-benzothiazolyl)thio]-, methyl ester; 6-Benzothiazolol, 2-(5-hexenylthio)-; 6-[(6-Hydroxy-2-benzothiazolyl)amino]hexanoic acid methyl ester; 2-(5-Hexenylamino)-6-benzothiazolol; 2-(5-Hexenylammino)-6-benzothiazolol maleic acid salt.

Claim 6

Dependent Claim 15 words

A compound selected from the group consisting of: 2-[[3-(Diethylamino)propyl]amino]-6-benzothiazolol; 2-[[3-(Diethylamino(propyl]amino]-6-benzothiazolol, hydroquinone dihydrochloride salt; 2-[[3-(Diethylamino(propyl]amino]-6-benzothiazolol dihydrochloride.

Claim 7

Dependent Claim 15 words

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USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1992-10-09	1993-04-10	1993-10-10	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1996-10-09	1997-04-10	1997-10-10	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2000-10-09	2001-04-10	2001-10-10	$7700.00	Window Closed / Lapsed

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