IP Library › Granted Patent US 11,034,650
Granted Patent B2
US 11,034,650 · App. 16/472,001 · Granted Jun 15, 2021

Compounds useful for treating a

Inventors: Michael Berger (Wiesbaden, DE); Thorsten Meyer (Wiesbaden, DE); Joachim Ullrich (Stadecken-Elsheim, DE); Ralf Warrass (Alzey, DE)
Assignee: Intervet Inc.
C07C259/06A61P11/00A61P31/04C07C317/50C07C323/60C07D213/56C07D217/18C07D235/14C07D267/10C07D277/28C07D295/155C07D307/52C07D333/20C07D405/12C07D409/12C07D413/12C07D417/12C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07C2601/16
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Quick Facts
Patent No.
US 11,034,650
App. No.
16/472,001
Granted
Jun 15, 2021
Kind
B2
Abstract

The present invention discloses compounds of formula (I) that are useful in the treatment of respiratory diseases of animals, especially Bovine or Swine Respiratory disease (BRD and SRD).

Claims (3339)

1. A compound according to formula A:

or a stereoisomer, pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of

No

A

L

M

1

cyclopropylamine

—CH 2 —

meta phenyl

2

(CH 3 ) 2 CHNH—

—CH 2 —

meta phenyl

3

CH 2 CHCH 2 NH—

—CH 2 —

meta phenyl

4

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

meta phenyl

5

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

6

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

7

CO 2 HCH 2 NH—

—CH 2 —

meta phenyl

8

(C 2 H 5 ) 2 N—

—CH 2 —

meta phenyl

9

morpholine

—CH 2 —

meta phenyl

10

4-tert-butyl-piperidine

—CH 2 —

meta phenyl

11

4-phenyl-piperidine

—CH 2 —

meta phenyl

12

4-phenyl-piperazine

—CH 2 —

meta phenyl

13

1-(pyridin-2-yl)-piperazine

—CH 2 —

meta phenyl

14

1,2,3,4-tetrahydro-

—CH 2 —

meta phenyl

isoquinoline

15

heliamine

—CH 2 —

meta phenyl

16

benzylamine

—CH 2 —

meta phenyl

17

N-methylbenzylamine

—CH 2 —

meta phenyl

18

4-chlorobenzylamine

—CH 2 —

meta phenyl

19

4-methoxybenzylamine

—CH 2 —

meta phenyl

20

4-dimethylaminobenzylamine

—CH 2 —

meta phenyl

21

4-trifluoromethylbenzylamine

—CH 2 —

meta phenyl

22

4-pyridylmethanamine

—CH 2 —

meta phenyl

23

3,4-dimethylbenzylamine

—CH 2 —

meta phenyl

24

cyclopropylamine

—CH 2 —

meta phenyl

25

(CH 3 ) 2 CHNH—

—CH 2 —

meta phenyl

26

CH 2 CHCH 2 NH—

—CH 2 —

meta phenyl

27

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

meta phenyl

28

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

29

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

30

CO 2 HCH 2 NH—

—CH 2 —

meta phenyl

31

(C 2 H 5 ) 2 N—

—CH 2 —

meta phenyl

32

morpholine

—CH 2 —

meta phenyl

33

1,1-dioxo-thiomorpholine

—CH 2 —

meta phenyl

34

4-tert-butyl-piperidine

—CH 2 —

meta phenyl

35

4-phenyl-piperidine

—CH 2 —

meta phenyl

36

4-phenyl-piperazine

—CH 2 —

meta phenyl

37

1-(pyridin-2-yl)-piperazine

—CH 2 —

meta phenyl

38

1,2,3,4-tetrahydro-

—CH 2 —

meta phenyl

isoquinoline

39

heliamine

—CH 2 —

meta phenyl

40

benzylamine

—CH 2 —

meta phenyl

41

N-methylbenzylamine

—CH 2 —

meta phenyl

42

4-chlorobenzylamine

—CH 2 —

meta phenyl

43

4-methoxybenzylamine

—CH 2 —

meta phenyl

44

4-dimethylaminobenzylamine

—CH 2 —

meta phenyl

45

4-trifluoromethylbenzylamine

—CH 2 —

meta phenyl

46

4-pyridylmethanamine

—CH 2 —

meta phenyl

47

3,4-dimethylbenzylamine

—CH 2 —

meta phenyl

48

(CH 3 ) 2 CHNH—

—CH 2 —

meta phenyl

49

CH 2 CHCH 2 NH—

—CH 2 —

meta phenyl

50

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

meta phenyl

51

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

52

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

meta phenyl

53

CO 2 HCH 2 NH—

—CH 2 —

meta phenyl

54

(C 2 H 5 ) 2 N—

—CH 2 —

meta phenyl

55

morpholine

—CH 2 —

meta phenyl

56

1,1-dioxo-thiomorpholine

—CH 2 —

meta phenyl

57

4-tert-butyl-piperidine

—CH 2 —

meta phenyl

58

4-phenyl-piperidine

—CH 2 —

meta phenyl

59

4-phenyl-piperazine

—CH 2 —

meta phenyl

60

1-(pyridin-2-yl)-piperazine

—CH 2 —

meta phenyl

61

1,2,3,4-tetrahydro-

—CH 2 —

meta phenyl

isoquinoline

62

heliamine

—CH 2 —

meta phenyl

63

benzylamine

—CH 2 —

meta phenyl

64

N-methylbenzylamine

—CH 2 —

meta phenyl

65

4-chlorobenzylamine

—CH 2 —

meta phenyl

66

4-methoxybenzylamine

—CH 2 —

meta phenyl

67

4-dimethylaminobenzylamine

—CH 2 —

meta phenyl

68

4-trifluoromethylbenzylamine

—CH 2 —

meta phenyl

69

4-pyridylmethanamine

—CH 2 —

meta phenyl

70

3,4-dimethylbenzylamine

—CH 2 —

meta phenyl

71

cyclopropylamine

—CH 2 —

para phenyl

72

(CH 3 ) 2 CHNH—

—CH 2 —

para phenyl

73

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

74

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

75

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

para phenyl

76

(C 2 H 5 ) 2 N—

—CH 2 —

para phenyl

77

morpholine

—CH 2 —

para phenyl

78

1,1-dioxo-thiomorpholine

—CH 2 —

para phenyl

79

4-tert-butyl-piperidine

—CH 2 —

para phenyl

80

4-phenyl-piperidine

—CH 2 —

para phenyl

81

4-phenyl-piperazine

—CH 2 —

para phenyl

82

1-(pyridin-2-yl)-piperazine

—CH 2 —

para phenyl

83

1,2,3,4-tetrahydro-

—CH 2 —

para phenyl

isoquinoline

84

heliamine

—CH 2 —

para phenyl

85

benzylamine

—CH 2 —

para phenyl

86

N-methylbenzylamine

—CH 2 —

para phenyl

87

4-chlorobenzylamine

—CH 2 —

para phenyl

88

4-methoxybenzylamine

—CH 2 —

para phenyl

89

4-trifluoromethylbenzylamine

—CH 2 —

para phenyl

90

4-pyridylmethanamine

—CH 2 —

para phenyl

91

3,4-dimethylbenzylamine

—CH 2 —

para phenyl

92

cyclopropylamine

—CH 2 —

para phenyl

93

(CH 3 ) 2 CHNH—

—CH 2 —

para phenyl

94

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

95

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

para phenyl

96

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

97

(C 2 H 5 ) 2 N—

—CH 2 —

para phenyl

98

morpholine

—CH 2 —

para phenyl

99

1,1-dioxo-thiomorpholine

—CH 2 —

para phenyl

100

4-phenyl-piperidine

—CH 2 —

para phenyl

101

1-(pyridin-2-yl)-piperazine

—CH 2 —

para phenyl

102

1,2,3,4-tetrahydro-

—CH 2 —

para phenyl

isoquinoline

103

heliamine

—CH 2 —

para phenyl

104

benzylamine

—CH 2 —

para phenyl

105

N-methylbenzylamine

—CH 2 —

para phenyl

106

4-chlorobenzylamine

—CH 2 —

para phenyl

107

4-methoxybenzylamine

—CH 2 —

para phenyl

108

4-dimethylaminobenzylamine

—CH 2 —

para phenyl

109

4-trifluoromethylbenzylamine

—CH 2 —

para phenyl

110

4-pyridylmethanamine

—CH 2 —

para phenyl

111

3,4-dimethylbenzylamine

—CH 2 —

para phenyl

112

cyclopropylamine

—CH 2 —

para phenyl

113

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

114

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

para phenyl

115

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

116

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

para phenyl

117

CO 2 HCH 2 NH—

—CH 2 —

para phenyl

118

(C 2 H 5 ) 2 N—

—CH 2 —

para phenyl

119

morpholine

—CH 2 —

para phenyl

120

4-tert-butyl-piperidine

—CH 2 —

para phenyl

121

4-phenyl-piperidine

—CH 2 —

para phenyl

122

4-phenyl-piperazine

—CH 2 —

para phenyl

123

1-(pyridin-2-yl)-piperazine

—CH 2 —

para phenyl

124

1,2,3,4-tetrahydro-

—CH 2 —

para phenyl

isoquinoline

125

heliamine

—CH 2 —

para phenyl

126

benzylamine

—CH 2 —

para phenyl

127

N-methylbenzylamine

—CH 2 —

para phenyl

128

4-chlorobenzylamine

—CH 2 —

para phenyl

129

4-methoxybenzylamine

—CH 2 —

para phenyl

130

4-dimethylaminobenzylamine

—CH 2 —

para phenyl

131

4-trifluoromethylbenzylamine

—CH 2 —

para phenyl

132

4-pyridylmethanamine

—CH 2 —

para phenyl

133

3,4-dimethylbenzylamine

—CH 2 —

para phenyl

134

4-dimethylaminobenzylamine

—CH 2 —

para phenyl

135

4-phenyl-piperazine

—CH 2 —

para phenyl

136

(CH 3 ) 3 CCH 2 NH—

—CH 2 —

para phenyl

137

CO 2 HCH 2 NH—

—CH 2 —

para phenyl

138

(CH 3 ) 2 N(CH 2 ) 2 NH—

—CH 2 —

para phenyl

139

CO 2 HCH 2 NH—

—CH 2 —

para phenyl

140

4-tert-butyl-piperidine

—CH 2 —

para phenyl

141

(CH 3 ) 2 CHNH—

—CH 2 —

para phenyl

142

1,1-dioxo-thiomorpholine

—CH 2 —

para phenyl

143

1,1-dioxo-thiomorpholine

—CH 2 —

meta phenyl

144

cyclopropylamine

—CH 2 —

meta phenyl

145

pyrrolidine

—CH 2 —

para phenyl

146

N-methylpiperazine

—CH 2 —

para phenyl

147

cyclobutylamine

—CH 2 —

para phenyl

148

cyclopentylamine

—CH 2 —

para phenyl

149

cyclohexylamine

—CH 2 —

para phenyl

150

CH 3 NH—

—CH 2 —

para phenyl

151

C 2 H 5 NH—

—CH 2 —

para phenyl

152

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

153

CH 3 O(CH 2 ) 3 NH—

—CH 2 —

para phenyl

154

CH 3 O(CH 2 ) 2 N(CH 3 )—

—CH 2 —

para phenyl

155

2,6-dimethylmorpholine

—CH 2 —

para phenyl

156

piperidine

—CH 2 —

para phenyl

157

3-pyridylmethanamine

—CH 2 —

para phenyl

158

2-pyridylmethanamine

—CH 2 —

para phenyl

159

furfurylamine

—CH 2 —

para phenyl

160

2-thienylmethanamine

—CH 2 —

para phenyl

161

4-methylbenzylamine

—CH 2 —

para phenyl

162

tetrahydrofurfurylamine

—CH 2 —

para phenyl

163

imidazol-2-ylmethanamine

—CH 2 —

para phenyl

164

CH 3 OCH 2 CH(CH 3 )NH—

—CH 2 —

para phenyl

165

2,6-dimethylmorpholine

—CH 2 —

para phenyl

166

piperidine

—CH 2 —

para phenyl

167

3-pyridylmethanamine

—CH 2 —

para phenyl

168

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

169

2-pyridylmethanamine

—CH 2 —

para phenyl

170

furfurylamine

—CH 2 —

para phenyl

171

2-thienylmethanamine

—CH 2 —

para phenyl

172

4-methylbenzylamine

—CH 2 —

para phenyl

173

imidazol-2-ylmethanamine

—CH 2 —

para phenyl

174

pyrrolidine

—CH 2 —

para phenyl

175

N-methylpiperazine

—CH 2 —

para phenyl

176

C 2 H 5 NH—

—CH 2 —

para phenyl

177

CH 3 O(CH 2 ) 3 NH—

—CH 2 —

para phenyl

178

CH 3 O(CH 2 ) 2 N(CH 3 )—

—CH 2 —

para phenyl

179

3-pyridylmethanamine

—CH 2 —

para phenyl

180

2-pyridylmethanamine

—CH 2 —

para phenyl

181

furfurylamine

—CH 2 —

para phenyl

182

2-thienylmethanamine

—CH 2 —

para phenyl

183

tetrahydrofurfurylamine

—CH 2 —

para phenyl

184

imidazol-2-ylmethanamine

—CH 2 —

para phenyl

185

CH 3 OCH 2 CH(CH 3 )NH—

—CH 2 —

para phenyl

186

1,4-oxazepane

—CH 2 —

para phenyl

187

piperidine

—CH 2 —

para phenyl

188

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

189

4-methylbenzylamine

—CH 2 —

para phenyl

190

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

191

2,6-dimethylmorpholine

—CH 2 —

para phenyl

192

NCCH 2 NH—

—CH 2 —

para phenyl

193

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

194

CH 3 NH—

—CH 2 —

para phenyl

195

cyclohexylamine

—CH 2 —

para phenyl

196

cyclopentylamine

—CH 2 —

para phenyl

197

cyclobutylamine

—CH 2 —

para phenyl

198

CH 3 OCH 2 CH(CH 3 )NH—

—CH 2 —

para phenyl

199

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

200

tetrahydrofurfurylamine

—CH 2 —

para phenyl

201

C 2 H 5 NH—

—CH 2 —

para phenyl

202

1,4-oxazepane

—CH 2 —

para phenyl

203

CH 3 O(CH 2 ) 2 N(CH 3 )—

—CH 2 —

para phenyl

204

NCCH 2 NH—

—CH 2 —

para phenyl

205

CH 3 O(CH 2 ) 3 NH—

—CH 2 —

para phenyl

206

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

207

CH 3 NH—

—CH 2 —

para phenyl

208

cyclohexylamine

—CH 2 —

para phenyl

209

cyclopentylamine

—CH 2 —

para phenyl

210

cyclobutylamine

—CH 2 —

para phenyl

211

N-methylpiperazine

—CH 2 —

para phenyl

212

pyrrolidine

—CH 2 —

para phenyl

213

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

214

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

215

1,4-oxazepane

—CH 2 —

para phenyl

216

NCCH 2 NH—

—CH 2 —

para phenyl

217

morpholine

—CH 2 —

ethenyl

218

cyclopropylamine

—CH 2 —

para phenyl

219

cyclopropylamine

—CH 2 —

para phenyl

220

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

221

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

222

morpholine

—CH 2 —

para phenyl

223

benzylamine

—CH 2 —

para phenyl

224

4-methoxybenzylamine

—CH 2 —

para phenyl

225

pyrrolidine

—CH 2 —

para phenyl

226

cyclobutylamine

—CH 2 —

para phenyl

227

cyclopentylamine

—CH 2 —

para phenyl

228

3-pyridylmethanamine

—CH 2 —

para phenyl

229

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

230

2-pyridylmethanamine

—CH 2 —

para phenyl

231

furfurylamine

—CH 2 —

para phenyl

232

2-thienylmethanamine

—CH 2 —

para phenyl

233

4-methylbenzylamine

—CH 2 —

para phenyl

234

tetrahydrofurfurylamine

—CH 2 —

para phenyl

235

cyclopropylamine

—CH 2 —

para phenyl

236

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

237

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

238

morpholine

—CH 2 —

para phenyl

239

benzylamine

—CH 2 —

para phenyl

240

4-methoxybenzylamine

—CH 2 —

para phenyl

241

4-pyridylmethanamine

—CH 2 —

para phenyl

242

pyrrolidine

—CH 2 —

para phenyl

243

cyclobutylamine

—CH 2 —

para phenyl

244

cyclopentylamine

—CH 2 —

para phenyl

245

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

246

NCCH 2 NH—

—CH 2 —

para phenyl

247

3-pyridylmethanamine

—CH 2 —

para phenyl

248

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

249

2-pyridylmethanamine

—CH 2 —

para phenyl

250

furfurylamine

—CH 2 —

para phenyl

251

2-thienylmethanamine

—CH 2 —

para phenyl

252

4-methylbenzylamine

—CH 2 —

para phenyl

253

tetrahydrofurfurylamine

—CH 2 —

para phenyl

254

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

255

cyclopropylamine

—CH 2 —

para phenyl

256

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

257

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

258

morpholine

—CH 2 —

para phenyl

259

benzylamine

—CH 2 —

para phenyl

260

4-methoxybenzylamine

—CH 2 —

para phenyl

261

4-pyridylmethanamine

—CH 2 —

para phenyl

262

pyrrolidine

—CH 2 —

para phenyl

263

cyclobutylamine

—CH 2 —

para phenyl

264

cyclopentylamine

—CH 2 —

para phenyl

265

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

266

NCCH 2 NH—

—CH 2 —

para phenyl

267

3-pyridylmethanamine

—CH 2 —

para phenyl

268

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

269

2-pyridylmethanamine

—CH 2 —

para phenyl

270

furfurylamine

—CH 2 —

para phenyl

271

2-thienylmethanamine

—CH 2 —

para phenyl

272

4-methylbenzylamine

—CH 2 —

para phenyl

273

tetrahydrofurfurylamine

—CH 2 —

para phenyl

274

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

275

4-pyridylmethanamine

—CH 2 —

para phenyl

276

benzylamine

—CH 2 —

para phenyl

277

4-chlorobenzylamine

—CH 2 —

para phenyl

278

4-pyridylmethanamine

—CH 2 —

para phenyl

279

4-trifluoromethylbenzylamine

—CH 2 —

para phenyl

280

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

281

(CH 3 ) 2 CHNH—

—CH 2 —

para phenyl

282

2-pyridylmethanamine

—CH 2 —

para phenyl

283

4-methylbenzylamine

—CH 2 —

para phenyl

284

4-fluorobenzylamine

—CH 2 —

para phenyl

285

CH 3 O(CH 2 ) 3 NH—

—CH 2 —

para phenyl

286

3-pyridylmethanamine

—CH 2 —

para phenyl

287

furfurylamine

—CH 2 —

para phenyl

288

CF 3 CH 2 NH—

—CH 2 —

para phenyl

289

2-thienylmethanamine

—CH 2 —

para phenyl

290

cyclopropylamine

—CH 2 —

thiophene

291

CH 2 CHCH 2 NH—

—CH 2 —

thiophene

292

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

thiophene

293

morpholine

—CH 2 —

thiophene

294

benzylamine

—CH 2 —

thiophene

295

4-methoxybenzylamine

—CH 2 —

thiophene

296

3-pyridylmethanamine

—CH 2 —

thiophene

297

2-pyridylmethanamine

—CH 2 —

thiophene

298

furfurylamine

—CH 2 —

thiophene

299

(5-methyloxazol-2-

—CH 2 —

thiophene

yl)methanamine

300

cyclopropylamine

—CH 2 —

thiophene

301

CH 2 CHCH 2 NH—

—CH 2 —

thiophene

302

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

thiophene

303

morpholine

—CH 2 —

thiophene

304

benzylamine

—CH 2 —

thiophene

305

4-methoxybenzylamine

—CH 2 —

thiophene

306

3-pyridylmethanamine

—CH 2 —

thiophene

307

2-pyridylmethanamine

—CH 2 —

thiophene

308

furfurylamine

—CH 2 —

thiophene

309

CF 3 CH 2 NH—

—CH 2 —

thiophene

310

(5-methyloxazol-2-

—CH 2 —

thiophene

yl)methanamine

311

cyclopropylamine

—CH 2 —

thiophene

312

CH 2 CHCH 2 NH—

—CH 2 —

thiophene

313

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

thiophene

314

morpholine

—CH 2 —

thiophene

315

benzylamine

—CH 2 —

thiophene

316

4-methoxybenzylamine

—CH 2 —

thiophene

317

4-pyridylmethanamine

—CH 2 —

thiophene

318

NCCH 2 NH—

—CH 2 —

thiophene

319

3-pyridylmethanamine

—CH 2 —

thiophene

320

2-pyridylmethanamine

—CH 2 —

thiophene

321

furfurylamine

—CH 2 —

thiophene

322

2-pyrimidinylmethanamine

—CH 2 —

thiophene

323

(5-methyloxazol-2-

—CH 2 —

thiophene

yl)methanamine

324

cyclopropylamine

—CH 2 —

pyridine

325

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

pyridine

326

morpholine

—CH 2 —

pyridine

327

benzylamine

—CH 2 —

pyridine

328

4-methoxybenzylamine

—CH 2 —

pyridine

329

4-pyridylmethanamine

—CH 2 —

pyridine

330

3-pyridylmethanamine

—CH 2 —

pyridine

331

2-pyridylmethanamine

—CH 2 —

pyridine

332

furfurylamine

—CH 2 —

pyridine

333

CF 3 CH 2 NH—

—CH 2 —

pyridine

334

(5-methyloxazol-2-

—CH 2 —

pyridine

yl)methanamine

335

cyclopropylamine

—CH 2 —

pyridine

336

CH 2 CHCH 2 NH—

—CH 2 —

pyridine

337

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

pyridine

338

morpholine

—CH 2 —

pyridine

339

benzylamine

—CH 2 —

pyridine

340

4-methoxybenzylamine

—CH 2 —

pyridine

341

4-pyridylmethanamine

—CH 2 —

pyridine

342

NCCH 2 NH—

—CH 2 —

pyridine

343

2-pyridylmethanamine

—CH 2 —

pyridine

344

furfurylamine

—CH 2 —

pyridine

345

CF 3 CH 2 NH—

—CH 2 —

pyridine

346

2-pyrimidinylmethanamine

—CH 2 —

pyridine

347

(5-methyloxazol-2-

—CH 2 —

pyridine

yl)methanamine

348

cyclopropylamine

—CH 2 —

pyridine

349

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

pyridine

350

morpholine

—CH 2 —

pyridine

351

benzylamine

—CH 2 —

pyridine

352

4-methoxybenzylamine

—CH 2 —

pyridine

353

2-pyridylmethanamine

—CH 2 —

pyridine

354

furfurylamine

—CH 2 —

pyridine

355

CF 3 CH 2 NH—

—CH 2 —

pyridine

356

2-pyrimidinylmethanamine

—CH 2 —

pyridine

357

(5-methyloxazol-2-

—CH 2 —

pyridine

yl)methanamine

358

NCCH 2 NH—

—CH 2 —

thiophene

359

thiazol-2-ylmethanamine

—CH 2 —

thiophene

360

2-pyrimidinylmethanamine

—CH 2 —

thiophene

361

CH 2 CHCH 2 NH—

—CH 2 —

pyridine

362

thiazol-2-ylmethanamine

—CH 2 —

pyridine

363

2-pyrimidinylmethanamine

—CH 2 —

pyridine

364

4-pyridylmethanamine

—CH 2 —

thiophene

365

thiazol-2-ylmethanamine

—CH 2 —

thiophene

366

2-pyrimidinylmethanamine

—CH 2 —

thiophene

367

3-pyridylmethanamine

—CH 2 —

pyridine

368

thiazol-2-ylmethanamine

—CH 2 —

pyridine

369

thiazol-2-ylmethanamine

—CH 2 —

thiophene

370

CH 2 CHCH 2 NH—

—CH 2 —

pyridine

371

4-pyridylmethanamine

—CH 2 —

pyridine

372

NCCH 2 NH—

—CH 2 —

pyridine

373

3-pyridylmethanamine

—CH 2 —

pyridine

374

thiazol-2-ylmethanamine

—CH 2 —

pyridine

375

NO 2

—

para phenyl

376

NH 2

—

para phenyl

377

NO 2

—

para phenyl

378

cyclopropylamine

—CH 2 —

para phenyl

379

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

380

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

381

morpholine

—CH 2 —

para phenyl

382

benzylamine

—CH 2 —

para phenyl

383

4-methoxybenzylamine

—CH 2 —

para phenyl

384

pyrrolidine

—CH 2 —

para phenyl

385

cyclobutylamine

—CH 2 —

para phenyl

386

cyclopentylamine

—CH 2 —

para phenyl

387

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

388

3-pyridylmethanamine

—CH 2 —

para phenyl

389

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

390

2-pyridylmethanamine

—CH 2 —

para phenyl

391

furfurylamine

—CH 2 —

para phenyl

392

2-thienylmethanamine

—CH 2 —

para phenyl

393

4-methylbenzylamine

—CH 2 —

para phenyl

394

tetrahydrofurfurylamine

—CH 2 —

para phenyl

395

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

396

cyclopropylamine

—CH 2 —

para phenyl

397

CH 2 CHCH 2 NH—

—CH 2 —

para phenyl

398

CH 3 O(CH 2 ) 2 NH—

—CH 2 —

para phenyl

399

morpholine

—CH 2 —

para phenyl

400

benzylamine

—CH 2 —

para phenyl

401

4-methoxybenzylamine

—CH 2 —

para phenyl

402

4-pyridylmethanamine

—CH 2 —

para phenyl

403

pyrrolidine

—CH 2 —

para phenyl

404

cyclobutylamine

—CH 2 —

para phenyl

405

cyclopentylamine

—CH 2 —

para phenyl

406

CH 3 (CH 2 ) 2 NH—

—CH 2 —

para phenyl

407

3-pyridylmethanamine

—CH 2 —

para phenyl

408

(2-chloro-4-

—CH 2 —

para phenyl

pyridyl)methanamine

409

2-pyridylmethanamine

—CH 2 —

para phenyl

410

furfurylamine

—CH 2 —

para phenyl

411

2-thienylmethanamine

—CH 2 —

para phenyl

412

4-methylbenzylamine

—CH 2 —

para phenyl

413

tetrahydrofurfurylamine

—CH 2 —

para phenyl

414

thiazol-2-ylmethanamine

—CH 2 —

para phenyl

and

415

4-pyridylmethanamine

—CH 2 —

para phenyl

No

n

R 1

C a

1

1

—CH 2 OH

(S)

2

1

—CH 2 OH

(S)

3

1

—CH 2 OH

(S)

4

1

—CH 2 OH

(S)

5

1

—CH 2 OH

(S)

6

1

—CH 2 OH

(S)

7

1

—CH 2 OH

(S)

8

1

—CH 2 OH

(S)

9

1

—CH 2 OH

(S)

10

1

—CH 2 OH

(S)

11

1

—CH 2 OH

(S)

12

1

—CH 2 OH

(S)

13

1

—CH 2 OH

(S)

14

1

—CH 2 OH

(S)

15

1

—CH 2 OH

(S)

16

1

—CH 2 OH

(S)

17

1

—CH 2 OH

(S)

18

1

—CH 2 OH

(S)

19

1

—CH 2 OH

(S)

20

1

—CH 2 OH

(S)

21

1

—CH 2 OH

(S)

22

1

—CH 2 OH

(S)

23

1

—CH 2 OH

(S)

24

1

—CH(CH 3 ) 2

(S)

25

1

—CH(CH 3 ) 2

(S)

26

1

—CH(CH 3 ) 2

(S)

27

1

—CH(CH 3 ) 2

(S)

28

1

—CH(CH 3 ) 2

(S)

29

1

—CH(CH 3 ) 2

(S)

30

1

—CH(CH 3 ) 2

(S)

31

1

—CH(CH 3 ) 2

(S)

32

1

—CH(CH 3 ) 2

(S)

33

1

—CH(CH 3 ) 2

(S)

34

1

—CH(CH 3 ) 2

(S)

35

1

—CH(CH 3 ) 2

(S)

36

1

—CH(CH 3 ) 2

(S)

37

1

—CH(CH 3 ) 2

(S)

38

1

—CH(CH 3 ) 2

(S)

39

1

—CH(CH 3 ) 2

(S)

40

1

—CH(CH 3 ) 2

(S)

41

1

—CH(CH 3 ) 2

(S)

42

1

—CH(CH 3 ) 2

(S)

43

1

—CH(CH 3 ) 2

(S)

44

1

—CH(CH 3 ) 2

(S)

45

1

—CH(CH 3 ) 2

(S)

46

1

—CH(CH 3 ) 2

(S)

47

1

—CH(CH 3 ) 2

(S)

48

1

(S)—CH(CH 3 )C 2 H 5

(S)

49

1

(S)—CH(CH 3 )C 2 H 5

(S)

50

1

(S)—CH(CH 3 )C 2 H 5

(S)

51

1

(S)—CH(CH 3 )C 2 H 5

(S)

52

1

(S)—CH(CH 3 )C 2 H 5

(S)

53

1

(S)—CH(CH 3 )C 2 H 5

(S)

54

1

(S)—CH(CH 3 )C 2 H 5

(S)

55

1

(S)—CH(CH 3 )C 2 H 5

(S)

56

1

(S)—CH(CH 3 )C 2 H 5

(S)

57

1

(S)—CH(CH 3 )C 2 H 5

(S)

58

1

(S)—CH(CH 3 )C 2 H 5

(S)

59

1

(S)—CH(CH 3 )C 2 H 5

(S)

60

1

(S)—CH(CH 3 )C 2 H 5

(S)

61

1

(S)—CH(CH 3 )C 2 H 5

(S)

62

1

(S)—CH(CH 3 )C 2 H 5

(S)

63

1

(S)—CH(CH 3 )C 2 H 5

(S)

64

1

(S)—CH(CH 3 )C 2 H 5

(S)

65

1

(S)—CH(CH 3 )C 2 H 5

(S)

66

1

(S)—CH(CH 3 )C 2 H 5

(S)

67

1

(S)—CH(CH 3 )C 2 H 5

(S)

68

1

(S)—CH(CH 3 )C 2 H 5

(S)

69

1

(S)—CH(CH 3 )C 2 H 5

(S)

70

1

(S)—CH(CH 3 )C 2 H 5

(S)

71

1

—CH 2 OH

(S)

72

1

—CH 2 OH

(S)

73

1

—CH 2 OH

(S)

74

1

—CH 2 OH

(S)

75

1

—CH 2 OH

(S)

76

1

—CH 2 OH

(S)

77

1

—CH 2 OH

(S)

78

1

—CH 2 OH

(S)

79

1

—CH 2 OH

(S)

80

1

—CH 2 OH

(S)

81

1

—CH 2 OH

(S)

82

1

—CH 2 OH

(S)

83

1

—CH 2 OH

(S)

84

1

—CH 2 OH

(S)

85

1

—CH 2 OH

(S)

86

1

—CH 2 OH

(S)

87

1

—CH 2 OH

(S)

88

1

—CH 2 OH

(S)

89

1

—CH 2 OH

(S)

90

1

—CH 2 OH

(S)

91

1

—CH 2 OH

(S)

92

1

—CH(CH 3 ) 2

(S)

93

1

—CH(CH 3 ) 2

(S)

94

1

—CH(CH 3 ) 2

(S)

95

1

—CH(CH 3 ) 2

(S)

96

1

—CH(CH 3 ) 2

(S)

97

1

—CH(CH 3 ) 2

(S)

98

1

—CH(CH 3 ) 2

(S)

99

1

—CH(CH 3 ) 2

(S)

100

1

—CH(CH 3 ) 2

(S)

101

1

—CH(CH 3 ) 2

(S)

102

1

—CH(CH 3 ) 2

(S)

103

1

—CH(CH 3 ) 2

(S)

104

1

—CH(CH 3 ) 2

(S)

105

1

—CH(CH 3 ) 2

(S)

106

1

—CH(CH 3 ) 2

(S)

107

1

—CH(CH 3 ) 2

(S)

108

1

—CH(CH 3 ) 2

(S)

109

1

—CH(CH 3 ) 2

(S)

110

1

—CH(CH 3 ) 2

(S)

111

1

—CH(CH 3 ) 2

(S)

112

1

(S)—CH(CH 3 )C 2 H 5

(S)

113

1

(S)—CH(CH 3 )C 2 H 5

(S)

114

1

(S)—CH(CH 3 )C 2 H 5

(S)

115

1

(S)—CH(CH 3 )C 2 H 5

(S)

116

1

(S)—CH(CH 3 )C 2 H 5

(S)

117

1

(S)—CH(CH 3 )C 2 H 5

(S)

118

1

(S)—CH(CH 3 )C 2 H 5

(S)

119

1

(S)—CH(CH 3 )C 2 H 5

(S)

120

1

(S)—CH(CH 3 )C 2 H 5

(S)

121

1

(S)—CH(CH 3 )C 2 H 5

(S)

122

1

(S)—CH(CH 3 )C 2 H 5

(S)

123

1

(S)—CH(CH 3 )C 2 H 5

(S)

124

1

(S)—CH(CH 3 )C 2 H 5

(S)

125

1

(S)—CH(CH 3 )C 2 H 5

(S)

126

1

(S)—CH(CH 3 )C 2 H 5

(S)

127

1

(S)—CH(CH 3 )C 2 H 5

(S)

128

1

(S)—CH(CH 3 )C 2 H 5

(S)

129

1

(S)—CH(CH 3 )C 2 H 5

(S)

130

1

(S)—CH(CH 3 )C 2 H 5

(S)

131

1

(S)—CH(CH 3 )C 2 H 5

(S)

132

1

(S)—CH(CH 3 )C 2 H 5

(S)

133

1

(S)—CH(CH 3 )C 2 H 5

(S)

134

1

—CH 2 OH

(S)

135

1

—CH(CH 3 ) 2

(S)

136

1

—CH 2 OH

(S)

137

1

—CH 2 OH

(S)

138

1

—CH(CH 3 ) 2

(S)

139

1

—CH(CH 3 ) 2

(S)

140

1

—CH(CH 3 ) 2

(S)

141

1

(S)—CH(CH 3 )C 2 H 5

(S)

142

1

(S)—CH(CH 3 )C 2 H 5

(S)

143

1

—CH 2 OH

(S)

144

1

(S)—CH(CH 3 )C 2 H 5

(S)

145

1

—CH 2 OH

(S)

146

1

—CH 2 OH

(S)

147

1

—CH 2 OH

(S)

148

1

—CH 2 OH

(S)

149

1

—CH 2 OH

(S)

150

1

—CH 2 OH

(S)

151

1

—CH 2 OH

(S)

152

1

—CH 2 OH

(S)

153

1

—CH 2 OH

(S)

154

1

—CH 2 OH

(S)

155

1

—CH 2 OH

(S)

156

1

—CH 2 OH

(S)

157

1

—CH 2 OH

(S)

158

1

—CH 2 OH

(S)

159

1

—CH 2 OH

(S)

160

1

—CH 2 OH

(S)

161

1

—CH 2 OH

(S)

162

1

—CH 2 OH

(S)

163

1

—CH 2 OH

(S)

164

1

—CH 2 OH

(S)

165

1

—CH(CH 3 ) 2

(S)

166

1

—CH(CH 3 ) 2

(S)

167

1

—CH(CH 3 ) 2

(S)

168

1

—CH(CH 3 ) 2

(S)

169

1

—CH(CH 3 ) 2

(S)

170

1

—CH(CH 3 ) 2

(S)

171

1

—CH(CH 3 ) 2

(S)

172

1

—CH(CH 3 ) 2

(S)

173

1

—CH(CH 3 ) 2

(S)

174

1

(S)—CH(CH 3 )C 2 H 5

(S)

175

1

(S)—CH(CH 3 )C 2 H 5

(S)

176

1

(S)—CH(CH 3 )C 2 H 5

(S)

177

1

(S)—CH(CH 3 )C 2 H 5

(S)

178

1

(S)—CH(CH 3 )C 2 H 5

(S)

179

1

(S)—CH(CH 3 )C 2 H 5

(S)

180

1

(S)—CH(CH 3 )C 2 H 5

(S)

181

1

(S)—CH(CH 3 )C 2 H 5

(S)

182

1

(S)—CH(CH 3 )C 2 H 5

(S)

183

1

(S)—CH(CH 3 )C 2 H 5

(S)

184

1

(S)—CH(CH 3 )C 2 H 5

(S)

185

1

(S)—CH(CH 3 )C 2 H 5

(S)

186

1

(S)—CH(CH 3 )C 2 H 5

(S)

187

1

(S)—CH(CH 3 )C 2 H 5

(S)

188

1

(S)—CH(CH 3 )C 2 H 5

(S)

189

1

(S)—CH(CH 3 )C 2 H 5

(S)

190

1

(S)—CH(CH 3 )C 2 H 5

(S)

191

1

(S)—CH(CH 3 )C 2 H 5

(S)

192

1

(S)—CH(CH 3 )C 2 H 5

(S)

193

1

(S)—CH(CH 3 )C 2 H 5

(S)

194

1

(S)—CH(CH 3 )C 2 H 5

(S)

195

1

(S)—CH(CH 3 )C 2 H 5

(S)

196

1

(S)—CH(CH 3 )C 2 H 5

(S)

197

1

(S)—CH(CH 3 )C 2 H 5

(S)

198

1

—CH(CH 3 ) 2

(S)

199

1

—CH(CH 3 ) 2

(S)

200

1

—CH(CH 3 ) 2

(S)

201

1

—CH(CH 3 ) 2

(S)

202

1

—CH(CH 3 ) 2

(S)

203

1

—CH(CH 3 ) 2

(S)

204

1

—CH(CH 3 ) 2

(S)

205

1

—CH(CH 3 ) 2

(S)

206

1

—CH(CH 3 ) 2

(S)

207

1

—CH(CH 3 ) 2

(S)

208

1

—CH(CH 3 ) 2

(S)

209

1

—CH(CH 3 ) 2

(S)

210

1

—CH(CH 3 ) 2

(S)

211

1

—CH(CH 3 ) 2

(S)

212

1

—CH(CH 3 ) 2

(S)

213

1

—CH 2 OH

(S)

214

1

—CH 2 OH

(S)

215

1

—CH 2 OH

(S)

216

1

—CH 2 OH

(S)

217

1

—CH(CH 3 ) 2

(S)

218

1

—C(CH 3 ) 2 NO 2

219

1

—C(CH 3 ) 2 OH

(S)

220

1

—C(CH 3 ) 2 OH

(S)

221

1

—C(CH 3 ) 2 OH

(S)

222

1

—C(CH 3 ) 2 OH

(S)

223

1

—C(CH 3 ) 2 OH

(S)

224

1

—C(CH 3 ) 2 OH

(S)

225

1

—C(CH 3 ) 2 OH

(S)

226

1

—C(CH 3 ) 2 OH

(S)

227

1

—C(CH 3 ) 2 OH

(S)

228

1

—C(CH 3 ) 2 OH

(S)

229

1

—C(CH 3 ) 2 OH

(S)

230

1

—C(CH 3 ) 2 OH

(S)

231

1

—C(CH 3 ) 2 OH

(S)

232

1

—C(CH 3 ) 2 OH

(S)

233

1

—C(CH 3 ) 2 OH

(S)

234

1

—C(CH 3 ) 2 OH

(S)

235

1

—C(CH 3 ) 2 SCH 3

(R)

236

1

—C(CH 3 ) 2 SCH 3

(R)

237

1

—C(CH 3 ) 2 SCH 3

(R)

238

1

—C(CH 3 ) 2 SCH 3

(R)

239

1

—C(CH 3 ) 2 SCH 3

(R)

240

1

—C(CH 3 ) 2 SCH 3

(R)

241

1

—C(CH 3 ) 2 SCH 3

(R)

242

1

—C(CH 3 ) 2 SCH 3

(R)

243

1

—C(CH 3 ) 2 SCH 3

(R)

244

1

—C(CH 3 ) 2 SCH 3

(R)

245

1

—C(CH 3 ) 2 SCH 3

(R)

246

1

—C(CH 3 ) 2 SCH 3

(R)

247

1

—C(CH 3 ) 2 SCH 3

(R)

248

1

—C(CH 3 ) 2 SCH 3

(R)

249

1

—C(CH 3 ) 2 SCH 3

(R)

250

1

—C(CH 3 ) 2 SCH 3

(R)

251

1

—C(CH 3 ) 2 SCH 3

(R)

252

1

—C(CH 3 ) 2 SCH 3

(R)

253

1

—C(CH 3 ) 2 SCH 3

(R)

254

1

—C(CH 3 ) 2 SCH 3

(R)

255

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

256

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

257

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

258

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

259

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

260

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

261

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

262

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

263

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

264

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

265

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

266

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

267

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

268

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

269

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

270

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

271

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

272

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

273

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

274

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

275

1

—C(CH 3 ) 2 OH

(S)

276

1

—C(CH 3 ) 2 NO 2

277

1

—C(CH 3 ) 2 NO 2

278

1

—C(CH 3 ) 2 NO 2

279

1

—C(CH 3 ) 2 NO 2

280

1

—C(CH 3 ) 2 NO 2

281

1

—C(CH 3 ) 2 NO 2

282

1

—C(CH 3 ) 2 NO 2

283

1

—C(CH 3 ) 2 NO 2

284

1

—C(CH 3 ) 2 NO 2

285

1

—C(CH 3 ) 2 NO 2

286

1

—C(CH 3 ) 2 NO 2

287

1

—C(CH 3 ) 2 NO 2

288

1

—C(CH 3 ) 2 NO 2

289

1

—C(CH 3 ) 2 NO 2

290

1

—C(CH 3 ) 2 OH

(S)

291

1

—C(CH 3 ) 2 OH

(S)

292

1

—C(CH 3 ) 2 OH

(S)

293

1

—C(CH 3 ) 2 OH

(S)

294

1

—C(CH 3 ) 2 OH

(S)

295

1

—C(CH 3 ) 2 OH

(S)

296

1

—C(CH 3 ) 2 OH

(S)

297

1

—C(CH 3 ) 2 OH

(S)

298

1

—C(CH 3 ) 2 OH

(S)

299

1

—C(CH 3 ) 2 OH

(S)

300

1

—C(CH 3 ) 2 SCH 3

(R)

301

1

—C(CH 3 ) 2 SCH 3

(R)

302

1

—C(CH 3 ) 2 SCH 3

(R)

303

1

—C(CH 3 ) 2 SCH 3

(R)

304

1

—C(CH 3 ) 2 SCH 3

(R)

305

1

—C(CH 3 ) 2 SCH 3

(R)

306

1

—C(CH 3 ) 2 SCH 3

(R)

307

1

—C(CH 3 ) 2 SCH 3

(R)

308

1

—C(CH 3 ) 2 SCH 3

(R)

309

1

—C(CH 3 ) 2 SCH 3

(R)

310

1

—C(CH 3 ) 2 SCH 3

(R)

311

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

312

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

313

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

314

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

315

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

316

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

317

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

318

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

319

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

320

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

321

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

322

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

323

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

324

1

—C(CH 3 ) 2 OH

(S)

325

1

—C(CH 3 ) 2 OH

(S)

326

1

—C(CH 3 ) 2 OH

(S)

327

1

—C(CH 3 ) 2 OH

(S)

328

1

—C(CH 3 ) 2 OH

(S)

329

1

—C(CH 3 ) 2 OH

(S)

330

1

—C(CH 3 ) 2 OH

(S)

331

1

—C(CH 3 ) 2 OH

(S)

332

1

—C(CH 3 ) 2 OH

(S)

333

1

—C(CH 3 ) 2 OH

(S)

334

1

—C(CH 3 ) 2 OH

(S)

335

1

—C(CH 3 ) 2 SCH 3

(R)

336

1

—C(CH 3 ) 2 SCH 3

(R)

337

1

—C(CH 3 ) 2 SCH 3

(R)

338

1

—C(CH 3 ) 2 SCH 3

(R)

339

1

—C(CH 3 ) 2 SCH 3

(R)

340

1

—C(CH 3 ) 2 SCH 3

(R)

341

1

—C(CH 3 ) 2 SCH 3

(R)

342

1

—C(CH 3 ) 2 SCH 3

(R)

343

1

—C(CH 3 ) 2 SCH 3

(R)

344

1

—C(CH 3 ) 2 SCH 3

(R)

345

1

—C(CH 3 ) 2 SCH 3

(R)

346

1

—C(CH 3 ) 2 SCH 3

(R)

347

1

—C(CH 3 ) 2 SCH 3

(R)

348

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

349

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

350

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

351

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

352

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

353

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

354

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

355

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

356

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

357

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

358

1

—C(CH 3 ) 2 OH

(S)

359

1

—C(CH 3 ) 2 OH

(S)

360

1

—C(CH 3 ) 2 OH

(S)

361

1

—C(CH 3 ) 2 OH

(S)

362

1

—C(CH 3 ) 2 OH

(S)

363

1

—C(CH 3 ) 2 OH

(S)

364

1

—C(CH 3 ) 2 SCH 3

(R)

365

1

—C(CH 3 ) 2 SCH 3

(R)

366

1

—C(CH 3 ) 2 SCH 3

(R)

367

1

—C(CH 3 ) 2 SCH 3

(R)

368

1

—C(CH 3 ) 2 SCH 3

(R)

369

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

370

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

371

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

372

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

373

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

374

1

—C(CH 3 ) 2 SO 2 CH 3

(R)

375

1

—CH 2 OH

(S)

376

1

—CH 2 OH

(S)

377

1

—CH(CH 3 ) 2

(S)

378

1

—C(═NOCH 3 )CH 3

(S)

379

1

—C(═NOCH 3 )CH 3

(S)

380

1

—C(═NOCH 3 )CH 3

(S)

381

1

—C(═NOCH 3 )CH 3

(S)

382

1

—C(═NOCH 3 )CH 3

(S)

383

1

—C(═NOCH 3 )CH 3

(S)

384

1

—C(═NOCH 3 )CH 3

(S)

385

1

—C(═NOCH 3 )CH 3

(S)

386

1

—C(═NOCH 3 )CH 3

(S)

387

1

—C(═NOCH 3 )CH 3

(S)

388

1

—C(═NOCH 3 )CH 3

(S)

389

1

—C(═NOCH 3 )CH 3

(S)

390

1

—C(═NOCH 3 )CH 3

(S)

391

1

—C(═NOCH 3 )CH 3

(S)

392

1

—C(═NOCH 3 )CH 3

(S)

393

1

—C(═NOCH 3 )CH 3

(S)

394

1

—C(═NOCH 3 )CH 3

(S)

395

1

—C(═NOCH 3 )CH 3

(S)

396

1

—COCH 3

(S)

397

1

—COCH 3

(S)

398

1

—COCH 3

(S)

399

1

—COCH 3

(S)

400

1

—COCH 3

(S)

401

1

—COCH 3

(S)

402

1

—COCH 3

(S)

403

1

—COCH 3

(S)

404

1

—COCH 3

(S)

405

1

—COCH 3

(S)

406

1

—COCH 3

(S)

407

1

—COCH 3

(S)

408

1

—COCH 3

(S)

409

1

—COCH 3

(S)

410

1

—COCH 3

(S)

411

1

—COCH 3

(S)

412

1

—COCH 3

(S)

413

1

—COCH 3

(S)

414

1

—COCH 3

(S)

415

1

—C(═NOCH 3 )CH 3

(S).

2. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutical acceptable carrier.

3. A method of treating an infection caused by a bacteria in an animal wherein the bacteria is at least one of the bacteria selected from the group Pasteurella multocida, Mannheimia haemolytica and Histophilus somni , comprising administering to an animal in need thereof an effective amount of the compound according to claim 1 .

4. The method of treating according to claim 3 wherein the bacteria causes bovine respiratory disease or swine respiratory disease.

Assignments (2)
CHANGE OF ADDRESS Recorded Sep 26, 2023
From: INTERVET INC.
To: INTERVET INC.
Reel/Frame 065028/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2019
From: BERGER, MICHAEL; MEYER, THORSTEN; ULLRICH, JOACHIM; WARRASS, RALF
To: INTERVET INC.
Reel/Frame 051293/0769 →
Priority Claims (1)
EP 16206790 · Dec 23, 2016 · regional
Continuity (1)
Related Publication 20190352256A1 · Nov 21, 2019