US 5,639,780 AGranted

N-benzyl indol-3-yl butanoic acid derivatives as cyclooxygenase inhibitors

AssigneeMerck Frosst Canada, Inc.

InventorsCheuk Kun Lau, Cameron Black, Daniel Guay, Jacques-Yves Gauthier, Yves LeBlanc, Patrick Roy, Yves Ducharme, Pierre Hamel

Life of this patent

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Abstract

The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

Claims13

Dependent claims

A compound of formula I ##STR18## or a pharmaceutically acceptable salt thereof, wherein:

Q is
(a) --OR or
(b) --NR.sup.11 R.sup.12 ;
X is
(a) --O or
(b) --S;
R is
(a) --H or
(b) --C.sub.1-4 alkyl or mono, di or tri-substituted --C.sub.1-4 alkyl, where the substituent is selected from F, Cl, Br and I;
R.sup.1 is
(a) --OCH.sub.3 or OCH.sub.2 CH.sub.3,
(b) --OCH.sub.2 F,
(c) --OCHF.sub.2,
(d) --OCF.sub.3,
(e) --CF.sub.3,
(f) --F, Cl, Br or I
(g) methyl or ethyl;
R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each independently
(a) --H,
(b) --F or Cl,
(c) --C.sub.1-5 alkyl or haloalkyl,
(d) --C.sub.3-6 cycloalkyl,
(e) --CF.sub.3, CF.sub.2 H or CFH.sub.2,
(f) --OH, OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
(g) nonsubstituted, mono- or di-substituted benzyl, wherein the substituent is selected from
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl,
(5) OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
(h) phenyl or mono- or di-substituted phenyl, wherein the substituent is selected from
(1) CF3,
(2) CN,
(3) F, Cl, Br, I,
(4) C.sub.1-6 alkyl,
(5) OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
or R.sup.2 together with R.sup.3 form an oxo group;
or R.sup.4 together with R.sup.5 form an oxo group;
or R.sup.6 together with R.sup.7 form an oxo group;
or R.sup.2 and R.sup.3 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally one hetero atom which is oxygen;
or R.sup.3 and R.sup.4 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or 7 members;
or R.sup.3 and R.sup.6 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or 7 members;
or R.sup.4 and R.sup.5 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally containing one hetero atom which is oxygen;
or R.sup.4 and R.sup.6 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or members;
or R.sup.6 and R.sup.7 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally containing an oxygen atom;
R.sup.8 is
(a) hydrogen or
(b) F, Cl or Br,
R.sup.9 is
(a) Br, Cl or I,
(b) SMe, S(O)Me, SEt, SCF.sub.2 H or SCF.sub.3 ;
R.sup.10 is methyl, ethyl or, benzyl optionally mono- or di-substituted, wherein the substituent is selected from
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br, I, and
(4) C.sub.1-6 alkyl;
R.sup.11 and R.sup.12 are each independently
(a) --H,
(b) --C.sub.1-4 alkyl,
(c) --C.sub.3-6 cycloalkyl,
(d) --OR,
(e) --C(O)R.sup.13,
(f) --S(O).sub.2 R.sup.14,
(g) mono-substituted C.sub.2-4 alkyl wherein the substituent is selected from
(1) hydroxy,
(2) amino,
(3) methylamino, and
(4) dimethylamino,
(h) phenyl, benzyl or pyridyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl;
R.sup.13 is
(a) --H,
(b) --C.sub.1-4 alkyl,
(c) --CF.sub.3,
(d) phenyl or benzyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl;
R.sup.14 is
(a) --C.sub.1-4 alkyl,
(b) --CF.sub.3,
(c) phenyl or benzyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl.

87 more elements

A compound selected from the group consisting of

(1) 3-[1-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-cyclopropyl]prop anoic acid,
(2) [4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-(ethane-1,2-diyl )]butanoic acid, sodium salt,
(3) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2-methylbutanoic acid,
(4) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)butanoic acid,
(5) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2,2-dimethylbutanoi c acid, sodium salt
(6) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2-hydroxy-2-methylb utanoic acid,
(7) (3S) and (3R) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid,
(8) [5-Methoxy-2-methyl-1-(4-methylthiobenzyl)indol-3-yl]-3-methylbutanoic acid,
(9) trans-2-[(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)methyl]cyclop ropanecarboxylic acid,
(10) (2R,3S ) -[(4-Bromobenzyl)-5- methoxy-2-methyl-1H-indol-3-yl]-2,3-dimethylbutanoic acid,
(11) (2R,3R)-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2,3-dimethylb utanoic acid,
(12) (2S,3R)-[1-(4-Bromobenzyl) -5-methoxy-2-methyl-1H-indol-3-yl]-2,3-dimethylbutanoic acid,
(13) (2S,3S)-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2,3-dimethylb utanoic acid,
(14) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2-methylpentanoic acid,
(15) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-4-oxobutanoic acid,
(16) cis-2-[(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)methyl]cyclopro panecarboxylic acid
(17) (R)-(-)-4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbut anoic acid,
(18) 2-[(5-Bromo-1-(4-bromobenzyl)-2-methyl-1H-indol-3-yl)methyl]benzoic acid,
(19) [2-(1-(4-Bromobenzyl)-5-methoxyl-2-methyl-1H-indol-3-yl) phenyl]acetic acid, sodium salt,
(20) 2-[(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)methyl]benzoic acid,
(21) [3-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]benzoic acid, sodium salt,
(22) 4-[1-(4-Bromobenzyl)-2,5-dimethyl-1H-indol-3-yl]butanoic acid,
(23) 4-[5-Bromo-1-(4-bromobenzyl)-2-methyl-1H-indol-3-yl]butanoic acid,
(24) 4-[1-(4-Chlorobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-(ethane-1,2-diyl )butanoic acid,
(25) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]butanoic acid,
(26) 4-[5-Bromo-1-(4-chlorobenzyl)-2-methyl-1H-indol-3-yl]butanoic acid,
(27) 4-[5-Chloro-1-(4-chlorobenzyl)-2-methyl-1H-indol-3-yl]butanoic acid,
(28) 4-[1-(4-Bromo-2-fluorobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]butanoic acid,
(29) 4-[1-(4-Bromo-2-fluorobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2-methylbut anoic acid,
(30) 4-[5-Methoxy-2-methyl-1-(4-methylthiobenzyl)-1H-indol-3-yl]-3-(ethane-1,2- diyl)butanoic acid,
(31) 4-[5-Bromo-1-(4-bromobenzyl) -2-methyl-1H-indol-3-yl]-3-(ethane-1,2-diyl)butanoic acid,
(32) trans 2-(4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]methyl) cyclopropanecarboxylic acid,
(33) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3-methyl-butanoic ac id,
(34) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2-methyl-butanoic ac id,
(35) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2,3-dimethyl-butanoi c acid,
(36) 4-(1-Benzyl-5-chloro-2-methyl-1H-indol-3-yl)pentanoic acid,
(37) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]pentanoic acid,
(38) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methyl-butanoic acid
(39) 4-[5-Methoxy-2-methyl-1-(4-methanesulfoxylbenzyl)-1H-indol-3-yl]-3-(ethane -1,2-diyl)butanoic acid,
(40) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]pentanoic acid,
(41) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2,3-dimethylbutanoi c acid, sodium salt,
(42) 3(S), 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3-methylbutanoic acid, sodium salt,
(43) 3(R), 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3-methylbutanoic acid, sodium salt,
(44) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-(ethane-1,2-diyl) -2-methylbutanoic acid,
(45) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-ethylbutanoic acid,
(46) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylpentanoic acid, sodium salt,
(47) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3,3-dimethylbutanoi c acid, sodium salt,
(48) 4-[1-(4-Bromobenzyl)-5-methyl-5-trifluoromethyl-1H-indol-3-yl]butanoic acid,
(49) 2(R) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2-methylbutanoic acid,
(50) 2(S), 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2-methylbutanoic acid, sodium salt,
(51) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2-benzylbutanoic ac id,
(52) 4-[5-Chloro-1-(4-iodobenzyl)-2-methyl-1H-indol-3-yl]butanoic acid,
(53) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2-ethylbutanoic acid,
(54) 4-[5-Bromo-1-(4-bromobenzyl)-2-methyl-1H-indol-3-yl]-3,3-dimethylbutanoic acid,
(55) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3,3-dimethylbutanoic acid,
(56) 2(R), 3(R) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2,3-dimethylbutanoic acid,
(57) 2(S), 3(R) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-2,3-dimethylbutanoic acid,
(58) 3(R) 4-[1-(4-Iodobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanoic acid,
(59) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3-(ethane-1,2-diyl)b utanoic acid,
(60) 3(R) 4-[1-(4-Ethylthiobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanoi c acid,
(61) Methyl 4-[1-(4-bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]butanoate,
(62) 2-{[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]acyl}benzoic acid,
(63) 5-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-2-methylbenzoic acid,
(64) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanamide,
(65) 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-(2-pyridyl)butana mide,
(66) [4-(1-(4-Bromobenzyl) -5-methoxy-2-methyl-1H-indol-3-yl)-3-(ethane-1,2-diyl)]butanoyl methanesulfonamide,
(67) 3(R) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanamide,
(68) 3(R) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N,N-dimethyl-3-meth ylbutanamide,
(69) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N(2-hydroxyethyl)-3 -methylbutanamide,
(70) 3(R) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1 H-indol-3-yl]-N-(3-dimethylaminopropyl)-3-ethylbutanamide,
(71) 3-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(2-hydroxyethyl)b enzamide,
(72) 3-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N,N-bis(2-hydroxyet hyl)benzamide,
(73) 3-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]benzamide,
(74) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(4-pyridyl)butana mide,
(75) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-[2-(N-pyrrolidiny l) ethyl]-3-methylbutanamide,
(76) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(3-pyridyl)butana mide,
(77) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]butanamide,
(78) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-methylbutanamide,
(79) N-{3-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]benzoyl}methanesu lfonamide,
(80) N-{2-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]methyl}benzoyl)me thanesulfonamide,
(81) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanethioa mide,
(82) N-Methyl-4-[1-(4-bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbu tanethioamide,
(83) 4-[1-(4-Bromobenzyl)-5-chloro-2-methyl-1H-indol-3-yl]-3-methylbutanethioam ide,
(84) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]butanethioamide,
(85) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-methylbutanethioa mide,and
(86) 3(R) 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanethioa mide, or a pharmaceutically acceptable salt thereof.

83 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/445,838Filed 22 May 1995
Granted: 17 Jun 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 231/12
Having two or three double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms, hydrocarbon or…
C07D 209/22
Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals: with…
C07D 233/56
Having two double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms or radicals containing only…
C07D 249/08
Not condensed with other rings: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Family

No related US applications are recorded in the indexed filing history.

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Abstract

A compound of formula I ##STR18## or a pharmaceutically acceptable salt thereof, wherein:

Q is
(a) --OR or
(b) --NR.sup.11 R.sup.12 ;
X is
(a) --O or
(b) --S;
R is
(a) --H or
(b) --C.sub.1-4 alkyl or mono, di or tri-substituted --C.sub.1-4 alkyl, where the substituent is selected from F, Cl, Br and I;
R.sup.1 is
(a) --OCH.sub.3 or OCH.sub.2 CH.sub.3,
(b) --OCH.sub.2 F,
(c) --OCHF.sub.2,
(d) --OCF.sub.3,
(e) --CF.sub.3,
(f) --F, Cl, Br or I
(g) methyl or ethyl;
R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are each independently
(a) --H,
(b) --F or Cl,
(c) --C.sub.1-5 alkyl or haloalkyl,
(d) --C.sub.3-6 cycloalkyl,
(e) --CF.sub.3, CF.sub.2 H or CFH.sub.2,
(f) --OH, OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
(g) nonsubstituted, mono- or di-substituted benzyl, wherein the substituent is selected from
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl,
(5) OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
(h) phenyl or mono- or di-substituted phenyl, wherein the substituent is selected from
(1) CF3,
(2) CN,
(3) F, Cl, Br, I,
(4) C.sub.1-6 alkyl,
(5) OR.sup.10, SR.sup.10, S(O)R.sup.10 or S(O).sub.2 R.sup.10,
or R.sup.2 together with R.sup.3 form an oxo group;
or R.sup.4 together with R.sup.5 form an oxo group;
or R.sup.6 together with R.sup.7 form an oxo group;
or R.sup.2 and R.sup.3 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally one hetero atom which is oxygen;
or R.sup.3 and R.sup.4 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or 7 members;
or R.sup.3 and R.sup.6 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or 7 members;
or R.sup.4 and R.sup.5 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally containing one hetero atom which is oxygen;
or R.sup.4 and R.sup.6 are joined so that together with the carbon atoms to which they are attached there is formed a saturated or aromatic monocyclic ring of 3, 4, 5, 6 or members;
or R.sup.6 and R.sup.7 are joined so that together with the carbon atom to which they are attached there is formed a saturated monocyclic ring of 3, 4, 5, 6 or 7 members, optionally containing an oxygen atom;
R.sup.8 is
(a) hydrogen or
(b) F, Cl or Br,
R.sup.9 is
(a) Br, Cl or I,
(b) SMe, S(O)Me, SEt, SCF.sub.2 H or SCF.sub.3 ;
R.sup.10 is methyl, ethyl or, benzyl optionally mono- or di-substituted, wherein the substituent is selected from
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br, I, and
(4) C.sub.1-6 alkyl;
R.sup.11 and R.sup.12 are each independently
(a) --H,
(b) --C.sub.1-4 alkyl,
(c) --C.sub.3-6 cycloalkyl,
(d) --OR,
(e) --C(O)R.sup.13,
(f) --S(O).sub.2 R.sup.14,
(g) mono-substituted C.sub.2-4 alkyl wherein the substituent is selected from
(1) hydroxy,
(2) amino,
(3) methylamino, and
(4) dimethylamino,
(h) phenyl, benzyl or pyridyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl;
R.sup.13 is
(a) --H,
(b) --C.sub.1-4 alkyl,
(c) --CF.sub.3,
(d) phenyl or benzyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl;
R.sup.14 is
(a) --C.sub.1-4 alkyl,
(b) --CF.sub.3,
(c) phenyl or benzyl optionally mono- or di-substituted, the substituents being selected from the group consisting of
(1) CF.sub.3,
(2) CN,
(3) F, Cl, Br or I,
(4) C.sub.1-6 alkyl.

87 more elements

Facts

Application

08/445,838Filed 22 May 1995

Granted

17 Jun 1997

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 231/12
Having two or three double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms, hydrocarbon or…
C07D 209/22
Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals: with…
C07D 233/56
Having two double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms or radicals containing only…
C07D 249/08
Not condensed with other rings: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles