US 8,772,307 B2Granted

Substituted spiro compounds and their use for producing pain-relief medicaments

AssigneeGruenenthal GmbH

InventorsRobert Frank, Melanie Reich, Ruth Jostock, Gregor Bahrenberg, Hans Schick, Birgitta Henkel, Helmut Sonnenschein

Life of this patent

Estimating the term…

Abstract

The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

Claims22

Dependent claims

A substituted spiro compound corresponding to formula I

wherein
m is 0, 1, 2, 3 or 4,
n is 1,
R1 represents a —C(═O)—R9 group;
R2 represents
a linear or branched, saturated or unsaturated, unsubstituted or mono- or polysubstituted aliphatic group optionally having at least one heteroatom as chain member;
an unsubstituted or mono- or polysubstituted, unsaturated or saturated cycloaliphatic group which optionally has at least one heteroatom as ring member and can be bound via a linear or branched, unsubstituted or mono- or polysubstituted alkylene, alkenylene or alkinylene group optionally having at least one heteroatom as chain member and/or condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system,
a phenyl group, unsubstituted or mono- or polysubstituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —O—C1-10 alkyl, —NH2, —NO2, —O—CF3, —S—CF3, —SH, —S—C1-5 alkyl, —C1-10 alkyl, —C(═O)—OH, —C(═O)—O—C1-5 alkyl, —O—C(═O)—C1-5 alkyl, —NH—C1-5 alkyl, —N(C1-5 alkyl)2, —NH—C(═O)—O—C1-5 alkyl, —C(═O)—H, —C(═O)—C1-5 alkyl, —C(═O)—NH2, —C(═O)—NH—C1-5 alkyl, C(═O)—N—(C1-5 alkyl)2, —S(═O)2—C1-5 alkyl, —S(═O)2 phenyl, —NH—S(═O)2—C1-5 alkyl, —NH—S(═O)2—C1-5 alkylenephenyl, —NH—S(═O)2—C1-5 alkylenenaphthyl, —NH—S(═O)2 phenyl, —NH—S(═O)2 naphthyl, —S(═O)2—NH—C1-5 alkyl, cyclohexyl, cyclopentyl, morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, pyridinyl, pyridazinyl, —(CH2)-benzo[b]furanyl, —O-phenyl, —O-benzyl, phenyl and benzyl, wherein in each case the cyclic portion of the radicals pyridinyl, cyclopentyl, cyclohexyl, morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, pyridazinyl, —S(═O)2 phenyl, —O-phenyl, —O-benzyl, phenyl, —(CH2)-benzo[b]furanyl, —NH—S(═O)2—C1-5 alkylenephenyl, —NH—S(═O)2—C1-5 alkylenenaphthyl, —NH—S(═O)2 phenyl, —NH—S(═O)2 naphthyl and benzyl can be substituted with 1, 2, 3, 4 or 5 substituents selected independently of one another from the group consisting of F, Cl, Br, —OH, —CF3, —SF5, —CN, —NO2, —C1-5 alkyl, —O—C1-5 alkyl, —O—CF3, —S—CF3, phenyl and —O-benzyl, with the proviso that either of the two meta positions and the para position of said phenyl group are not both substituted with substituents which are respectively bound to the phenyl group via an identical atom selected from the group consisting of oxygen, sulfur and nitrogen;
an unsubstituted or mono- or polysubstituted group selected from the group consisting of naphthyl, (1,3)-benzodioxolyl, (1,4)-benzodioxanyl, thiophenyl, furanyl, pyrrolyl, pyrazolyl, pyranyl, pyridinyl, imidazolyl, indolyl, isoindolyl, benzo[b]furanyl, benzo[b]thiophenyl, thiazolyl, oxazolyl, isoxazolyl, pyridazinyl, pyrazinyl, pyrimidinyl, indazolyl, quinazolinyl, quinoxalinyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzoxazolyl, benzotriazolyl, benzisoxazolyl, [1,2,3,4]-tetrahydronaphthyl, [1,2,3,4]-tetrahydroquinolinyl, [1,2,3,4]-tetrahydroisoquinolinyl, [1,2,3,4]-tetrahydroquinazolinyl;
2H-benzo[1.4]oxazin-3(4H)-onyl, (3,4)-dihydroquinolin-2(1H)-onyl, [3,4]-dihydro-2H-1,4-benzoxazinyl and benzothiazolyl, or
an unsubstituted or mono- or polysubstituted aryl or heteroaryl group which is bound via a linear or branched, unsubstituted or mono- or polysubstituted alkylene, alkenylene or alkinylene group optionally having at least one heteroatom as chain member and optionally can be condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system;
R3 represents a halogen group, a nitro group, a hydroxy group, a thiol group;
an —O—R11 group, an —S—R12 group, or a linear or branched, saturated or unsaturated, unsubstituted or mono- or polysubstituted aliphatic group;
R4 represents hydrogen;
R9 represents
a linear or branched, saturated or unsaturated, aliphatic group, unsubstituted or mono- or polysubstituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —SH and —NH2, wherein said aliphatic group is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neo-pentyl, n-hexyl, 2-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, —(CH2)—(CH2)—(C(CH3)3), —(CH2)—(CH)(C2H5)—(CH2)—(CH2)—(CH2)—(CH3), ethenyl (vinyl), ethinyl, propenyl (—CH2CH═CH2, —CH═CH—CH3, —C(═CH2)—CH3), 2-methylpropenyl, propinyl (—CH2—C≡CH, —C≡C—CH3), butenyl, butinyl, pentenyl, pentinyl, hexenyl, hexinyl, octenyl and octinyl;
or
an unsubstituted or mono- or polysubstituted aryl or heteroaryl group which can be bound via a linear or branched, alkylene, alkenylene, or alkinylene group, unsubstituted or mono- or polysubstituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of F, Cl, Br, —OH, —SH, —NH2, —CN, —NO2 and phenyl, wherein the phenyl radical can be substituted with 1, 2, 3, 4 or 5 substituents selected independently of one another from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl and neo-pentyl, and/or condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system, wherein said alkylene group is selected from the group consisting of —(CH2)—, —(CH2)2—, —C(H)(CH3)—, —C(CH3)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —C(H)(CH3)—(CH2)—, and —C(H)(C2H5)—(CH2)—;
and
R11 and R12 each independently represent
a linear or branched, saturated or unsaturated, unsubstituted aliphatic group;
an unsubstituted, unsaturated or saturated cycloaliphatic group which optionally has at least one heteroatom as ring member and can be bound via a linear or branched, unsubstituted alkylene, alkenylene or alkinylene group and/or condensed with an unsubstituted mono- or polycyclic ring system, or
an unsubstituted aryl or heteroaryl group which can be bound via a linear or branched, unsubstituted alkylene, alkenylene or alkinylene group and/or condensed with an unsubstituted mono- or polycyclic ring system;
wherein the substituents of the above-mentioned aliphatic groups can be independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —SH and —NH2;
or a salt thereof.

22 more elements

A compound selected from the group consisting of:

[1] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[2] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[3] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[4] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[5] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[6] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenylamide
[7] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[8] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[9] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[10] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[11] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[12] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[13] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-m-tolylamide
[14] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[15] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[16] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[17] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[18] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[19] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[20] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-ethylphenyl)amide
[21] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[22] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[23] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[24] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[25] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[26] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-propylphenyl)amide
[27] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[28] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[29] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[30] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[31] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[32] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-fluorophenyl)amide
[33] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[34] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[35] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[36] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[37] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[38] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-chlorophenyl)amide
[39] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chlorophenyl)amide
[40] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chlorophenyl)amide
[41] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chlorophenyl)amide
[42] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chlorophenyl)amide
[43] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chlorophenyl)amide
[44] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-iodophenyl)amide
[45] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-iodophenyl)amide
[46] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-iodophenyl)amide
[47] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[48] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[49] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[50] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[51] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[52] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methoxyphenyl)amide
[53] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[54] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[55] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[56] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[57] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[58] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methylsulfanylphenyl)amide
[59] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[60] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[61] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[62] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[63] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[64] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methylsulfanylphenyl)amide
[65] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[66] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[67] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[68] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[69] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[70] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-methylsulfanylphenyl)amide
[71] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[72] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[73] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[74] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[75] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[76] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-isopropylphenyl)amide
[77] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[78] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[79] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[80] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[81] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[82] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[83] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[84] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[85] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[86] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[87] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[88] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-trifluoromethylphenyl)amide
[89] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[90] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[91] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[92] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[93] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[94] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-trifluoromethylphenyl)amide
[95] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid biphenyl-4-amide
[96] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid biphenyl-4-amide
[97] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid biphenyl-4-amide
[98] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[99] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[100] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[101] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[102] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[103] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-phenoxyphenyl)amide
[104] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[105] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[106] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[ω] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[•] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[109] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-benzyloxyphenyl)amide
[110] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[111] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[112] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[113] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[114] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[115] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid cyclohexylamide
[116] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[117] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[118] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[119] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[120] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[121] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid benzylamide
[122] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[123] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[124] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[125] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[126] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[127] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid phenethylamide
[128] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[129] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[130] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[131] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[132] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[133] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methylbenzylamide
[134] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[135] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[136] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[137] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[138] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[139] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-4-methoxybenzylamide
[140] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[141] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[142] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[143] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[144] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[145] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[146] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[147] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[148] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[149] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[150] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[151] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[152] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[153] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[154] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[155] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid o-tolylamide
[156] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[157] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[158] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[159] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[160] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[161] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-ethylphenyl)amide
[162] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[163] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[164] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[165] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[166] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[167] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[168] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[169] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[1710] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[171] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[172] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[173] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-fluorophenyl)amide
[174] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[175] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[176] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[177] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[178] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[179] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-fluorophenyl)amide
[180] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[181] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[182] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[183] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[184] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[185] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chlorophenyl)amide
[186] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[187] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[188] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[189] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[190] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[191] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-bromophenyl)amide
[192] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-bromophenyl)amide
[193] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-bromophenyl)amide
[194] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-bromophenyl)amide
[195] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-bromophenyl)amide
[196] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-bromophenyl)amide
[197] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-bromophenyl)amide
[198] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[199] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[200] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[201] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[202] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[203] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-methoxyphenyl)amide
[204] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[205] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[206] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[207] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[208] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[209] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(3-methoxyphenyl)amide
[210] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[211] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[212] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[213] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[214] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[215] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[216] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-phenoxyphenyl)amide
[217] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-phenoxyphenyl)amide
[218] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-phenoxyphenyl)amide
[219] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-phenoxyphenyl)amide
[220] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-phenoxyphenyl)amide
[221] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[222] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[223] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[224] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[225] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[226] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-chloro-5-trifluoromethylphenyl)amide
[227] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-2-trifluoromethylphenyl)amide
[228] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-2-trifluoromethylphenyl)amide
[229] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-2-trifluoromethylphenyl)amide
[230] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-2-trifluoromethylphenyl)amide
[231] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-2-trifluoromethylphenyl)amide
[232] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[233] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[234] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[235] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[236] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[237] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-chloro-3-trifluoromethylphenyl)amide
[238] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[239] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[240] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[241] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[242] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[243] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2-tert-butyl-6-methylphenyl)amide
[244] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[245] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[246] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[247] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[248] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[249] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[250] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[251] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[252] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[253] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[254] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylamide
[255] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[256] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[257] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[258] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[259] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[260] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid phenylamide
[261] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[262] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[263] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[264] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[265] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[266] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-trifluoromethylphenyl)amide
[267] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[268] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[269] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[270] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[271] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[272] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-methoxyphenyl)amide
[273] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-methoxyphenyl)amide
[274] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-methoxyphenyl)amide
[275] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-methoxyphenyl)amide
[276] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-methoxyphenyl)amide
[277] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(3-methoxyphenyl)amide
[278] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[279] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[280] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[281] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[282] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[283] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-tert-butylphenyl)amide
[284] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-2-methylbenzylamide
[285] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-2-methylbenzylamide
[286] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-2-methylbenzylamide
[287] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-2-methylbenzylamide
[288] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclopentylamide
[289] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclopentylamide
[290] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclopentylamide
[291] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclopentylamide
[292] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylmethylamide
[293] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylmethylamide
[294] 3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylmethylamide
[295] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylmethylamide
[296] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclohexylmethylamide
[297] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclooctylamide
[298] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclooctylamide
[299] 3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclooctylamide
[300] 3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclooctylamide
[301] 3-(4-trifluoromethylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid cyclooctylamide
[302] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(2-morpholin-4-ylethyl)amide
[303] 3-tert-butyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[304] 3-phenyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propinone
[305] 1-(3-tert-butyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-phenylpropinone
[306] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)methylamide
[307] (4-tert-butylphenyl)-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone
[308] (4-hydroxy-3-methoxyphenyl)-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone
[309] (4-iodophenyl)-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone
[310] 3-tert-butyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[311] 3-(4-trifluoromethoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid p-tolylamide
[312] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[313] 2-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)ethanone
[314] 1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-3-(4-trifluoromethylphenyl)propenone
[315] 3-(4-hydroxy-3-methoxyphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[316] (4-tert-butylphenyl)-[3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]methanone
[317] 3-(4-tert-butylphenyl)-1-[3-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]propenone
[318] 3-(4-tert-butylphenyl)-1-[3-(4-trifluoromethoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]propenone
[319] 3-naphthalen-2-yl-1-oxa-2,8-diazaspiro[4.5] dec-2-ene-8-carboxylic acid-(4-ethylphenyl)amide
[320] 1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-3,3-di-p-tolylpropenone
[321] 3-(4-tert-butylphenyl)-2-methyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[322] 3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-ene-8-carboxylic acid benzhydrylamide
[323] 3-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[324] 2-(4-tert-butylbenzylidene)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-buten-1-one
[325] 3-(4-isopropylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[326] 3-(4-octylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[327] 3-(4-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[328] 3-(4-pentylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[329] 3-(3-chloropyridin-2-yl)-1-oxa-2,8-diazaspiro[4.5] dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[330] 3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-thiocarboxylic acid-(4-pentafluorosulfanylphenyl)amide
[331] (3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)(9H-xanthen-9-yl)methanone
[332] (9H-fluoren-9-yl)(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone
[333] N-(4-tert-butylphenyl)-3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[334] (E)-3-(4-cyclohexylphenyl)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-2-en-1-one
[335] N-(4-tert-butylphenyl)-3-(4-cyclohexylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[336] (E)-3-(4-tert-butylphenyl)-3-phenyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-2-en-1-one
[337] (2E,4E)-3-(4-tert-butylphenyl)-5-phenyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)penta-2,4-dien-1-one
[338] (Z)-3-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(thiophen-3-yl)prop-2-en-1-one
[339] (E)-3-(4-tert-butylphenyl)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
[340] (E)-N-(5-(8-(3-(4-tert-butylphenyl)acryloyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-yl)-2-fluorophenyl)methanesulfonamide
[341] (E)-3-(4-pentafluorosulfanyl)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-2-en-1-one
[342] (E)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(2-morpholino-6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[343] N-(2-fluoro-4-(1-oxo-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propan-2-yl)phenyl)methanesulfonamide
[344] N-(2-fluoro-4-(1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-1-oxopropan-2-yl)phenyl)methanesulfonamide
[344] (Z)-3-(4-tert-butylphenyl)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(thiophen-3-yl)prop-2-en-1-one
[345] (E)-3-(3-bromophenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-2-en-1-one
[346] (E)-3-(2-bromophenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)prop-2-en-1-one
[347] 3-(3-fluorophenyl)-N-(4-(trifluoromethyl)phenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-ene-8-carboxamide
[348] N-(4-tert-butylphenyl)-3-(4-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[349] 3-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propan-1-one
[351] N-(4-tert-butylphenyl)-3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[352] N-(4-tert-butylphenyl)-3-(2-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[353] (E)-3-(4-tert-butylphenyl)-1-(3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)prop-2-en-1-one
[354] (Z)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-4,4-dimethyl-3-phenylpent-2-en-1-one
[355] (E)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[356] (E)-1-(3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[357] (2E,4E)-3-tert-butyl-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-5-phenylpenta-2,4-dien-1-one
[358] (2E,4E)-3-(4-tert-butylphenyl)-1-(3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-5-phenylpenta-2,4-dien-1-one
[359] (Z)-3-(4-tert-butylphenyl)-3-(3,4-dichlorophenyl)-1-(3-(2-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)prop-2-en-1-one
[360] (Z)-3-(4-tert-butylphenyl)-3-(3,4-dichlorophenyl)-1-(3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)prop-2-en-1-one
[361] 1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-one
[362] (E)-1-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[363] 1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-one
[364] N-(4-tert-butylphenyl)-3-(2-fluorophenyl)-6-methyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[365] (E)-1-(3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[366] N-(2-fluoro-4-(1-(3-(3-fluorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-1-oxopropan-2-yl)phenyl)methanesulfonamide
[367] (E)-1-(6-methyl-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-(2-(piperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)prop-2-en-1-one
[368] (E)-3-(2-bromo-4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-2-en-1-one
[369] N-(4-tert-butylphenyl)-6-methyl-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[370] 2-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propan-1-one
[371] N-(4-tert-butylphenyl)-3-phenyl-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-carboxamide
[372] N-(4-tert-butylbenzyl)-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[373] N-(4-tert-butylphenyl)-3-phenyl-1-oxa-2,8-diazaspiro[4.6]undec-2-ene-8-carboxamide
[374] N-(4-tert-butylbenzyl)-3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[375] N-(1-(4-tert-butylphenyl)ethyl)-3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[376] N-(4-tert-butylcyclohexyl)-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[377] N-(4-tert-butylphenethyl)-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[378] N-(4-tert-butylphenyl)-3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[379] 8-(5-tert-butyl-1H-benzo[d]imidazol-2-yl)-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene
[380] 3-phenyl-8-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene
[381] (E)-N-(2-fluoro-4-(3-oxo-3-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)prop-1-enyl)phenyl)methanesulfonamide
[382] (E)-N-(2-fluoro-4-(3-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-3-oxoprop-1-enyl)phenyl)methanesulfonamide
[383] 5-tert-butyl-2-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)benzo[d]oxazole
[384] 5-tert-butyl-2-(3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)benzo[d]oxazole
[385] 6-methyl-3-phenyl-N-(4-(trifluoromethyl)phenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[386] 3-benzyl-N-(4-tert-butylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[387] N-(4-tert-butylphenyl)-3-phenethyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxamide
[388] 3-(4-hydroxy-3-methoxyphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]decen-8-yl)propenone
[389] 3-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]decen-8-yl)propenone
[390] 3-(3-chloropyridin-2-yl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[391] 3,3-di-p-tolyl-1-(3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[392] 3-(4-tert-butylphenyl)-1-[3-(4-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[393] 3-(4-tert-butylphenyl)-2-ethyl-1-(3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[394] (4-tert-butylphenyl)-(3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)methanone
[395] 3-(4-tert-butylphenyl)-1-(3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[396] 3-(4-tert-butylphenyl)-2-methyl-1-(3-p-tolyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[397] 2-(4-tert-butylphenyl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]-but-2-en-1-one
[398] 3-(4-tert-butylphenyl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]propinone
[399] 3-(4-tert-butylphenyl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]propenone
[400] 1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-2,2-diphenyl-propan-1-one
[401] 1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-2,2-diphenylethanone
[402] 3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(2,3)-dihydrobenzo[1.4] dioxin-6-yl)amide
[403] 3-(6-tert-butylpyridin-3-yl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[404] 3-(6-tert-butylpyridin-3-yl)-1-[3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl]propenone
[405] 2,2-diphenyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)-propan-1-one
[406] 3-(6-tert-butylpyridin-3-yl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[407] 3-(4-isopropylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[408] 3-(2,3-dihydrobenzo[1,4] dioxin-6-yl)-1-oxa-2,8-diazaspiro[4.5] dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide
[409] N-[2-fluoro-4-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5][dec-2-ene-8-carbonyl]phenyl]methanesulfonamide
[410] N-[2-fluoro-4-(3-phenyl-1-oxa-2,8-diazaspiro[4.5][dec-2-ene-8-carbonyl]phenyl]methanesulfonamide
[411] 3-(4-cyclohexylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5] dec-2-en-8-yl)propenone
[412] 1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-2,2,2-triphenylethanone
[413] [3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-(9H-xanthen-9-yl)methanone
[414] [3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-(9H-fluoren-9-yl)methanone
[415] [3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-(2-chloro-6-trifluoromethylpyridin-3-yl)methanone
[416] [3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-(2-morpholin-4-yl-6-trifluoromethylpyridin-3-yl)methanone
[417] 3-(4-tert-butylphenyl)-1-[3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[418] 3-(4-tert-butylphenyl)-1-[3-(2,3-dihydrobenzo[1.4]dioxin-6-yl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-ylpropenone
[419] 3-(4-tert-butylphenyl)-1-[3-(4-cyclohexylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[420] N-[4-[3-(4-cyclohexylphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carbonyl]-2-fluorophenyl]methanesulfonamide
[421] 2-hydroxy-2,2-diphenyl-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-8-yl]ethanone
[422] (3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)-(9H-xanthen-9-yl)methanone
[426] 3-(4-tert-butylphenyl)-1-(3-quinolin-3-yl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[424] 3-(2,3-dihydrobenzo[1.4]dioxin-6-yl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trilfluoromethylphenyl)amide
[425] 3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trilfuormethylphenyl)amide
[426] (4-tert-butylphenyl)-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]methanone
[427] 3-(4-cyclohexylphenyl)-1-oxa-2,8-diaza-sprio[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethylphenyl)amide
[428] 3-(4-tert-butylphenyl)-3-(4-chlorophenyl)-1-[3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[429] 3-(4-tert-butylphenyl)-1-[3-(3-chlorophenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-3-(3-methoxyphenyl)propenone
[430] 3-(4-tert-butylphenyl)-1-[3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-3-(4-trifluoromethylphenyl)propenone
[431] 3-(4-pentafluorosulfanylphenyl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[432] 3-(4-tert-butylphenyl)-1-[3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propenone
[433] 3-(4-tert-butylphenyl)-1-[3-(4-chloro-3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]propinone
[434] 3-(4-tert-butylphenyl)-1-[3-(3-methoxyphenyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-3-(2-trifluoromethylphenyl)propenone
[435] 3-thiazol-2-yl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-isopropylphenyl)amide
[436] 3-thiazol-2-yl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-trifluoromethoxyphenyl)amide
[437] 3,3-bis-(4-tert-butylphenyl)-1-(3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl)propenone
[438] 3-thiazol-2-yl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-8-carboxylic acid-(4-tert-butylphenyl)amide;
and physiologically compatible salts thereof.

436 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/914,927Filed 17 May 2006
Priority: DE 10 2005 023 78319 May 2005
Published: US 2008/0269271 A130 Oct 2008
Granted: 8 Jul 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification29 codes

C07D 498/10
In which the condensed system contains two hetero rings: spiro-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/12
Drugs for disorders of the alimentary tract or the digestive system: antidiarrhoeals

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US 2008/0269271 A1Pre-grant publication · published 30 Oct 2008
US 8,772,307 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

A substituted spiro compound corresponding to formula I

wherein
m is 0, 1, 2, 3 or 4,
n is 1,
R1 represents a —C(═O)—R9 group;
R2 represents
a linear or branched, saturated or unsaturated, unsubstituted or mono- or polysubstituted aliphatic group optionally having at least one heteroatom as chain member;
an unsubstituted or mono- or polysubstituted, unsaturated or saturated cycloaliphatic group which optionally has at least one heteroatom as ring member and can be bound via a linear or branched, unsubstituted or mono- or polysubstituted alkylene, alkenylene or alkinylene group optionally having at least one heteroatom as chain member and/or condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system,
a phenyl group, unsubstituted or mono- or polysubstituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —O—C1-10 alkyl, —NH2, —NO2, —O—CF3, —S—CF3, —SH, —S—C1-5 alkyl, —C1-10 alkyl, —C(═O)—OH, —C(═O)—O—C1-5 alkyl, —O—C(═O)—C1-5 alkyl, —NH—C1-5 alkyl, —N(C1-5 alkyl)2, —NH—C(═O)—O—C1-5 alkyl, —C(═O)—H, —C(═O)—C1-5 alkyl, —C(═O)—NH2, —C(═O)—NH—C1-5 alkyl, C(═O)—N—(C1-5 alkyl)2, —S(═O)2—C1-5 alkyl, —S(═O)2 phenyl, —NH—S(═O)2—C1-5 alkyl, —NH—S(═O)2—C1-5 alkylenephenyl, —NH—S(═O)2—C1-5 alkylenenaphthyl, —NH—S(═O)2 phenyl, —NH—S(═O)2 naphthyl, —S(═O)2—NH—C1-5 alkyl, cyclohexyl, cyclopentyl, morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, pyridinyl, pyridazinyl, —(CH2)-benzo[b]furanyl, —O-phenyl, —O-benzyl, phenyl and benzyl, wherein in each case the cyclic portion of the radicals pyridinyl, cyclopentyl, cyclohexyl, morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, pyridazinyl, —S(═O)2 phenyl, —O-phenyl, —O-benzyl, phenyl, —(CH2)-benzo[b]furanyl, —NH—S(═O)2—C1-5 alkylenephenyl, —NH—S(═O)2—C1-5 alkylenenaphthyl, —NH—S(═O)2 phenyl, —NH—S(═O)2 naphthyl and benzyl can be substituted with 1, 2, 3, 4 or 5 substituents selected independently of one another from the group consisting of F, Cl, Br, —OH, —CF3, —SF5, —CN, —NO2, —C1-5 alkyl, —O—C1-5 alkyl, —O—CF3, —S—CF3, phenyl and —O-benzyl, with the proviso that either of the two meta positions and the para position of said phenyl group are not both substituted with substituents which are respectively bound to the phenyl group via an identical atom selected from the group consisting of oxygen, sulfur and nitrogen;
an unsubstituted or mono- or polysubstituted group selected from the group consisting of naphthyl, (1,3)-benzodioxolyl, (1,4)-benzodioxanyl, thiophenyl, furanyl, pyrrolyl, pyrazolyl, pyranyl, pyridinyl, imidazolyl, indolyl, isoindolyl, benzo[b]furanyl, benzo[b]thiophenyl, thiazolyl, oxazolyl, isoxazolyl, pyridazinyl, pyrazinyl, pyrimidinyl, indazolyl, quinazolinyl, quinoxalinyl, quinolinyl, isoquinolinyl, benzimidazolyl, benzoxazolyl, benzotriazolyl, benzisoxazolyl, [1,2,3,4]-tetrahydronaphthyl, [1,2,3,4]-tetrahydroquinolinyl, [1,2,3,4]-tetrahydroisoquinolinyl, [1,2,3,4]-tetrahydroquinazolinyl;
2H-benzo[1.4]oxazin-3(4H)-onyl, (3,4)-dihydroquinolin-2(1H)-onyl, [3,4]-dihydro-2H-1,4-benzoxazinyl and benzothiazolyl, or
an unsubstituted or mono- or polysubstituted aryl or heteroaryl group which is bound via a linear or branched, unsubstituted or mono- or polysubstituted alkylene, alkenylene or alkinylene group optionally having at least one heteroatom as chain member and optionally can be condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system;
R3 represents a halogen group, a nitro group, a hydroxy group, a thiol group;
an —O—R11 group, an —S—R12 group, or a linear or branched, saturated or unsaturated, unsubstituted or mono- or polysubstituted aliphatic group;
R4 represents hydrogen;
R9 represents
a linear or branched, saturated or unsaturated, aliphatic group, unsubstituted or mono- or polysubstituted with one or more substituents independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —SH and —NH2, wherein said aliphatic group is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neo-pentyl, n-hexyl, 2-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, —(CH2)—(CH2)—(C(CH3)3), —(CH2)—(CH)(C2H5)—(CH2)—(CH2)—(CH2)—(CH3), ethenyl (vinyl), ethinyl, propenyl (—CH2CH═CH2, —CH═CH—CH3, —C(═CH2)—CH3), 2-methylpropenyl, propinyl (—CH2—C≡CH, —C≡C—CH3), butenyl, butinyl, pentenyl, pentinyl, hexenyl, hexinyl, octenyl and octinyl;
or
an unsubstituted or mono- or polysubstituted aryl or heteroaryl group which can be bound via a linear or branched, alkylene, alkenylene, or alkinylene group, unsubstituted or mono- or polysubstituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of F, Cl, Br, —OH, —SH, —NH2, —CN, —NO2 and phenyl, wherein the phenyl radical can be substituted with 1, 2, 3, 4 or 5 substituents selected independently of one another from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl and neo-pentyl, and/or condensed with an unsubstituted or mono- or polysubstituted mono- or polycyclic ring system, wherein said alkylene group is selected from the group consisting of —(CH2)—, —(CH2)2—, —C(H)(CH3)—, —C(CH3)2—, —(CH2)3—, —(CH2)4—, —(CH2)5—, —C(H)(CH3)—(CH2)—, and —C(H)(C2H5)—(CH2)—;
and
R11 and R12 each independently represent
a linear or branched, saturated or unsaturated, unsubstituted aliphatic group;
an unsubstituted, unsaturated or saturated cycloaliphatic group which optionally has at least one heteroatom as ring member and can be bound via a linear or branched, unsubstituted alkylene, alkenylene or alkinylene group and/or condensed with an unsubstituted mono- or polycyclic ring system, or
an unsubstituted aryl or heteroaryl group which can be bound via a linear or branched, unsubstituted alkylene, alkenylene or alkinylene group and/or condensed with an unsubstituted mono- or polycyclic ring system;
wherein the substituents of the above-mentioned aliphatic groups can be independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —SH and —NH2;
or a salt thereof.

22 more elements

Facts

Application

11/914,927Filed 17 May 2006

Priority

DE 10 2005 023 78319 May 2005

Published

US 2008/0269271 A130 Oct 2008

Granted

8 Jul 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification29 codes

C07D 498/10
In which the condensed system contains two hetero rings: spiro-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/12
Drugs for disorders of the alimentary tract or the digestive system: antidiarrhoeals