ES2477968T9 - Compuesto de triazolopiridina, y acción del mismo como inhibidor de prolil-hidroxilasa e inductor de la producción de eritropoyetina - Google Patents
Compuesto de triazolopiridina, y acción del mismo como inhibidor de prolil-hidroxilasa e inductor de la producción de eritropoyetina Download PDFInfo
- Publication number
- ES2477968T9 ES2477968T9 ES10799914.6T ES10799914T ES2477968T9 ES 2477968 T9 ES2477968 T9 ES 2477968T9 ES 10799914 T ES10799914 T ES 10799914T ES 2477968 T9 ES2477968 T9 ES 2477968T9
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- Spain
- Prior art keywords
- nmr
- amino
- triazolo
- dmso
- mhz
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- -1 Triazolopyridine compound Chemical class 0.000 title description 19
- 102000003951 Erythropoietin Human genes 0.000 title 1
- 108090000394 Erythropoietin Proteins 0.000 title 1
- 229940078467 Prolyl hydroxylase inhibitor Drugs 0.000 title 1
- 229940105423 erythropoietin Drugs 0.000 title 1
- 239000000411 inducer Substances 0.000 title 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 title 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 167
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 120
- 150000001875 compounds Chemical class 0.000 description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 37
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000000338 in vitro Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- FHXAZIRZQXEKGQ-UHFFFAOYSA-N OC(=O)CNC(=O)c1c(O)cc(-c2cccc(Cl)c2)n2ncnc12 Chemical compound OC(=O)CNC(=O)c1c(O)cc(-c2cccc(Cl)c2)n2ncnc12 FHXAZIRZQXEKGQ-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JDIANWNCWXMZRT-UHFFFAOYSA-N 2-[[6-hydroxy-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridine-5-carbonyl]amino]acetic acid;hydrochloride Chemical compound Cl.C12=NC=NN2C(C(=O)NCC(=O)O)=C(O)C=C1C1=CC=CC(C(F)(F)F)=C1 JDIANWNCWXMZRT-UHFFFAOYSA-N 0.000 description 1
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- BAXPNSKMBUZWBC-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)cc(-c2cccc(c2F)C(F)(F)F)n2ncnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)cc(-c2cccc(c2F)C(F)(F)F)n2ncnc12 BAXPNSKMBUZWBC-UHFFFAOYSA-N 0.000 description 1
- UKWGMBHQFZZPSJ-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)cc(-c2ccccc2F)n2ncnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)cc(-c2ccccc2F)n2ncnc12 UKWGMBHQFZZPSJ-UHFFFAOYSA-N 0.000 description 1
- VELXXWZXQLUECO-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)cc(CCC2CC2)n2ncnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)cc(CCC2CC2)n2ncnc12 VELXXWZXQLUECO-UHFFFAOYSA-N 0.000 description 1
- CSSCCRYABUWARL-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)cc(CCC2CCC2)n2ncnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)cc(CCC2CCC2)n2ncnc12 CSSCCRYABUWARL-UHFFFAOYSA-N 0.000 description 1
- OGERHEOETJZNKU-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)cc(Cc2ccc(F)cc2)n2ncnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)cc(Cc2ccc(F)cc2)n2ncnc12 OGERHEOETJZNKU-UHFFFAOYSA-N 0.000 description 1
- LTQGDRFIXLPJTK-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)ccc2ncnn12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)ccc2ncnn12 LTQGDRFIXLPJTK-UHFFFAOYSA-N 0.000 description 1
- GZFRSQALFNDYIM-UHFFFAOYSA-N Cl.OC(=O)CNC(=O)c1c(O)ccn2c(CCC3CCCCC3)nnc12 Chemical compound Cl.OC(=O)CNC(=O)c1c(O)ccn2c(CCC3CCCCC3)nnc12 GZFRSQALFNDYIM-UHFFFAOYSA-N 0.000 description 1
- CRQRYBPQWYMJIX-UHFFFAOYSA-N Cl.S1C(C)=CC=C1C1=CC(O)=C(C(=O)NCC(O)=O)C2=NC=NN12 Chemical compound Cl.S1C(C)=CC=C1C1=CC(O)=C(C(=O)NCC(O)=O)C2=NC=NN12 CRQRYBPQWYMJIX-UHFFFAOYSA-N 0.000 description 1
- NALAUGMPMIVAOW-UHFFFAOYSA-N N12N=CN=C2C(C(=O)NCC(=O)O)=C(O)C=C1CCC1=CC=CC=C1 Chemical compound N12N=CN=C2C(C(=O)NCC(=O)O)=C(O)C=C1CCC1=CC=CC=C1 NALAUGMPMIVAOW-UHFFFAOYSA-N 0.000 description 1
- SYQWYIBSNAEHEZ-UHFFFAOYSA-N OC(=O)CNC(=O)c1c(O)cc(-c2cc(F)cc(c2)C(F)(F)F)n2ncnc12 Chemical compound OC(=O)CNC(=O)c1c(O)cc(-c2cc(F)cc(c2)C(F)(F)F)n2ncnc12 SYQWYIBSNAEHEZ-UHFFFAOYSA-N 0.000 description 1
- UTTATOSFLLPRDC-UHFFFAOYSA-N OC(=O)CNC(=O)c1c(O)cc(-c2ccc(F)c(c2)C(F)(F)F)n2ncnc12 Chemical compound OC(=O)CNC(=O)c1c(O)cc(-c2ccc(F)c(c2)C(F)(F)F)n2ncnc12 UTTATOSFLLPRDC-UHFFFAOYSA-N 0.000 description 1
- DFGQLHALVMWKQP-UHFFFAOYSA-N OC(=O)CNC(=O)c1c(O)cc(CCCc2ccccc2)n2ncnc12 Chemical compound OC(=O)CNC(=O)c1c(O)cc(CCCc2ccccc2)n2ncnc12 DFGQLHALVMWKQP-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
Description
[Tabla 1]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 1
-
clorhidrato de ácido {[5-(4-fluoro-3trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]amino}acético
imagen71 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,31 (s, 1H), 7,73-7,82 (m, 1H), 8,34-8,43 (m, 1H), 8,43-8,51 (m, 1H), 8,61 (s, 1H), 9,99 (t, 1H, J = 5,6 Hz). 399 397
- 2
-
clorhidrato de ácido [(7-hidroxi-5-fenetil[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen72 RMN 1H (DMSO-D6, 400MHZ)) 3,12 (t, 2H, J = 7,8 Hz), 3,41 (t, 2H, J = 7,8 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,81 (s, 1H), 7,147,33 (m, 5H), 8,60 (s, 1H), 9,85 (t, 1H, J=5,6 Hz). 341 339
- 3
-
clorhidrato de ácido [(5-butil-7hidroxi[1,2,4]triazolo[1, 5-a]piridin-8-carbonil)amino]acético
imagen73 RMN 1H (DMSO-D6, 400 MHz) : 0,93 (t, 3H, J=7,4 Hz), 1,39 (td, 2H, J = 14,8, 7,4 Hz), 1,72-1,79 (m, 2H), 3,10 (t, 2H, J = 7,7 Hz), 4,21 (d, 2H, J = 5,5 Hz), 6,85 (s, 293 291
- 1H), 8,56 (s, 1H) , 9,84 (t, 1H, J=5,6 Hz).
- 4
-
clorhidrato de ácido [(5,6-dietil-7hidroxi[1,2,4]triazolo[1, 5-a]piridin-8-carbonil)amino]acético
imagen74 RMN 1H (DMSO-D6, 400 MHz) : 1,15 (t, 3H, J = 7,5 Hz), 1,29 (t, 3H, J = 7,5 Hz), 2,72 (q, 2H, J = 7,5 Hz), 3,20 (q, 2H, J = 7,6 Hz), 4,21 (d, 2H, J = 5,6 Hz), 8,52 (s, 1H), 9,95 (t, 1H, J = 5,6 Hz). 293 291
- 5
-
clorhidrato de ácido [(7-hidroxi-6-fenetil[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen75 RMN 1H (DMSO-D6, 400 MHz) : 2,93 (s, 4H), 4,22 (d, 2H, J = 5,7 Hz), 7,19 (tt, 1H, J = 7,1, 1,8 Hz), 7,23-7,31 (m, 4H), 8,50 (s, 1H), 8,78 (s, 1H), 9,97 (s, 1H). 341 339
72 [Tabla 2]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 6
-
clorhidrato de ácido [(5-butil-6-cloro-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen76 RMN 1H (DMSO-D6, 400 MHz) : 0,93 (t, 3H, J = 7,3 Hz), 1,361,47 (m, 2H), 1,64-1,72 (m, 2H), 3,15-3,28 (m, 2H), 4,15 (d, 2H, J = 2,8 Hz), 8,74 (s a, 1H), 10,20 (s a, 1H). 327 325
- 7
-
clorhidrato de ácido [(7-hidroxi-2-metil-5fenetil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen77 RMN 1H (DMSO-D6, 400 MHz) : 2,52 (s, 3H), 3,10 (t, 2H, J = 7,8 Hz), 3,35 (t, 2H, J = 7,8 Hz), 4,19 (d, 2H, J = 5,7 Hz), 6,69 (s, 1H), 7,18-7,31 (m, 5H), 9,81 (t, 1H, J = 5,5 Hz). 355 353
- 8
-
clorhidrato de ácido {[8-(3,3-dimetilbutil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen78 RMN 1H (DMSO-D6, 400 MHz) : 0,98 (s, 9H), 1,57-1,66 (m, 2H), 2,89-2,99 (m, 2H), 4,25 (d, 2H, J = 5,4 Hz), 7,42 (s, 1H), 8. 64 (s, 1H), 10,42 321 319
- (t, 1H, J = 5,4 Hz), 13,28 (s, 1H).
- 9
-
ácido [(7-hidroxi-6fenil-[1,2,4]triazolo[4,3-a]piridin-8carbonil)-amino]acético
imagen79 RMN 1H (DMSO-D6, 400 MHz) : 4,06 (d, 2H, J = 5,5 Hz), 7,397,46 (m, 3H), 7,60 (dd, 2H, J = 8,3, 1,4 Hz), 8,39 (s, 1H), 8,86 (s, 1H), 313 311
- 10,50 (t, 1H, J = 5,7 Hz), 12,59 (s, 1H), 13,75 (s, 1H) .
- 10
-
clorhidrato de ácido [(7-hidroxi-[1,2,4]triazolo[4,3-a]piridin-8carbonil)-amino]acético
imagen80 RMN 1H (DMSO-D6, 400 MHz) : 4,07 (s, 2H), 6,65 (d, 1H, J = 7,7 Hz), 8,32 (d, 1H, J = 7,7 Hz), 8,99 (s, 1H), 10,09 (s, 1H). 237 235
73 [Tabla 3]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 11
-
ácido [(6-hidroxi[1,2,3]-triazolo[1,5a]piridin-7-carbonil)amino]acético
imagen81 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,2 Hz), 7,31 (d, 1H, J = 9,7 Hz), 8,20 (d, 1H, J = 9,7 Hz), 8,39 (s, 1H), 10,36 (t, 1H, J = 5,2 Hz), 13,82 (s, 1H). 237 235
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 12
-
clorhidrato de ácido [(7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen82 RMN 1H (DMSO-D6, 400 MHz) : 4,22 (d, 2H, J = 5,6 Hz), 6,93 (d, 1H, J = 7,7 Hz), 8,56 (s, 1H), 8,96 (d, 1H, J = 7,7 Hz), 9,81-9,91 (m, 1H). 237 235
- 13
-
clorhidrato de ácido [(7hidroxi-2fenil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen83 RMN 1H (DMSO-D6, 400 MHz) : 4,27 (d, 2H, J = 5,6 Hz), 6,94 (d, 1H, J = 7,7 Hz), 7,55-7,58 (m, 3H), 8,31-8,33 (m, 2H), 9,00 (d, 1H, J = 7,3 Hz), 10,11 (t, 1H, J = 5,2 Hz). 313 311
- 14
- clorhidrato de ácido ({5[2-(4-clorofenil)etil]-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil}-amino)acético RMN 1H (DMSO-D6, 400 MHz) : 3,12 (2H, t, J = 7,9 Hz), 3,40 (2H, t, J = 7,7 Hz), 4,21 (2H, d, J = 5,6 Hz), 6,80 (1H, s), 7,27 (2H, d, J = 8,5 Hz), 7,35 (2H, d, J = 8,5 Hz), 8,59 (1H, s), 9,85 (1H, t, J = 5,6 Hz). 375 373
74 [Tabla 4]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 15
-
clorhidrato de ácido [(2ciclopropil-7-hidroxi-5fenetil-[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen84 RMN 1H (DMSO-D6, 400 MHz) : 1,04-1,12 (m, 4H), 2,17-2,23 (m, 1H), 3,10 (t, 2H, J = 7,9 Hz), 3,29-3,37 (m, 2H), 4,18 (d, 2H, J = 5,3 Hz), 6,66 (s, 1H), 7,18-7,32 (m, 381 379
- 5H), 9,84 (t, 1H, J = 4,9 Hz), 14,10 (s, 1H).
- 16
-
clorhidrato de ácido ({7hidroxi-5-[2-(4-trifluorometilfenil)etil][1,2,4]triazol o[1,5-a]piridin-8-carbonil}amino)acético
imagen85 RMN 1H (DMSO-D6, 400 MHz) : 3,21 (2H, t, J = 7,8 Hz), 3,44 (2H, t, J = 7,8 Hz), 4,20 (2H, d, J = 5,8 Hz), 6,83 (1H, s), 7,48 (2H, d, J = 8,1 H2) , 7,66 (2H, 409 407
- d, J = 8,1 Hz), 8,59 (1H, s), 9,819,88 (1H, m).
- 17
-
clorhidrato de ácido ({5[2-(4-fluorofenil)etil]-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil}-amino)acético
imagen86 RMN 1H (DMSO-D6, 400 MHz) : 3,11 (2H, t, J = 7,9 Hz), 3,39 (2H, t, J = 7,7 Hz), 4,21 (2H, d, J = 5,2 Hz), 6,80 (1H, s), 7,07-7,16 (2H, m), 7,23-7,30 (2H, m), 8,60 (1H, s), 9,85 (1H, t, J = 5,4 Hz). 359 357
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 18
-
clorhidrato de ácido {[7-hidroxi-5-(3metilbutil)-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen87 RMN 1H (DMSO-D6, 400 MHz) : 0,95 (6H, d, J =6,5 Hz), 1,581,70 (3H, m), 3,07-3,13 (2H, m), 4,21 (2H, d, J = 5,6 Hz), 6,87 (1H, s), 8,57 (1H, s), 9,85 (1H, t, J = 5,6 Hz). 307 305
75 76 [Tabla 5]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 19
-
clorhidrato de ácido ({5-[2-(3,5difluorofenil)etil]-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil}-amino)acético
imagen88 RMN 1H (DMSO-D6, 400 MHz) : 3,15 (2H, t, J = 7,8 Hz), 3,42 (2H, t, J = 7,8 Hz), 4,20 (2H, d, J = 5,6 Hz), 6,83 (1H, s), 6,97-7,11 (3H, m), 8,58-8,61 (1H, m), 9,799,89 (1H, m). 377 375
- 20
-
clorhidrato de ácido [(5-ciclopentilmetil-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen89 RMN 1H (DMSO-D6, 400 MHz) : 1,21-1,32 (2H, m), 1,45-1,55 (2H, m), 1,591,74 (4H, m), 2,40-2,49 (1H, m), 3,09 (2H, d, J = 7,3 Hz), 4,21 (2H, d, J = 5,6 319 317
- Hz), 6,88 (1H, s), 8,55 (1H, s), 9,85 (1H, t, J = 5,6 Hz).
- 21
-
clorhidrato de ácido {[5-(3,5-difluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen90 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,8 Hz), 7,29 (s, 1H), 7,56 (tt, 1H, J = 9,3, 2,3 Hz), 7,78-7,86 (m, 2H), 8,62 (s, 1H), 9,99 (t, 1H, J = 5,8 Hz). 349 347
- 22
-
clorhidrato de ácido [(7-hidroxi-5fenil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen91 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,12 (s, 1H), 7,59-7,62 (m, 3H), 7,998,02 (m, 2H), 8,58 (s, 1H), 9,98 (t, 1H, J = 5,6 Hz). 313 311
- 23
-
clorhidrato de ácido {[5-(3-cloro-4fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen92 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,23 (s, 1H), 7,67 (dd, 1H, J = 8,9, 8,9 Hz), 8,05 (ddd, 1H, J = 8,9, 2,4, 4,8 Hz), 8,30 (dd, 1H, J = 7,3, 2,4 Hz), 8,60 (s, 1H), 9,98 (t, 1H, J = 5,4 Hz). 365 363
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 24
-
clorhidrato de ácido {[5-(3,3-dimetilbutil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen93 RMN 1H (DMSO-D6, 400 MHz) : 0,98 (s, 9H), 1,591,70 (m, 2H), 3,01-3,13 (m, 2H), 4,21 (d, 2H, J = 5,6 Hz), 6,89 (s, 1H), 8,57 (s, 1H), 9,84 (t, 1H, J = 5,6 Hz). 321 319
- 25
-
clorhidrato de ácido {[5-(3,4-difluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen94 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,5 Hz), 7,22 (s, 1H), 7. 69 (dt, 1H, J = 15,0, 5,3 Hz), 7,92-7,94 (m, 1H), 8,17 (ddd, 1H, J = 11,9, 7,7, 349 347
- 2,2 Hz), 8,60 (s, 1H), 9,98 (t, 1H, J = 5,5 Hz).
- 26
-
clorhidrato de ácido {[7-hidroxi-5-(ptolil)[1,2,4]triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen95 RMN 1H (DMSO-D6, 400 MHz) : 2,42 (s, 3H), 4,24 (d, 2H, J = 5,5 Hz), 7,09 (s, 1H), 7,40 (d, 2H, J = 8,2 Hz), 7,93 (d, 2H, J = 8,2 Hz), 8,58 (s, 1H), 9,97 (t, 1H, J = 5,5 Hz). 327 325
- 27
-
clorhidrato de ácido [(5-ciclohexil-7-hidroxi[1,2,4]-triazolo[2,5a]piridin-8-carbonil)amino]acético
imagen96 RMN 1H (DMSO-D6, 400 MHz) : 1,21-1,62 (5H, m), 1,69-1,79 (1H, m), 1,801,88 (2H, m), 1,98-2,09 (2H, m), 3,31-3,43 (1H, m), 4,20 (2H, d, J = 5,8 Hz), 6,76 (1H, s), 8,56 (1H, s), 9,80-9,87 (1H, m). 319 317
77 [Tabla 6]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 28
-
clorhidrato de ácido [(5-ciclohexilmetil-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen97 RMN 1H (DMSO-D6, 400 MHz) : 0,98-1,23 (5H, m), 1,56-1,70 (5H, m), 1,901,99 (1H, m), 3,00 (2H, d, J = 7,2 Hz), 4,21 (2H, d, J = 5,6 Hz), 6,84 (1H, s), 8,55 (1H, s), 9,85 (1H, t, J = 5,6 Hz). 333 331
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 29
-
ácido {[7-hidroxi-5-(3fenilpropil)[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen98 RMN 1H (DMSO-D6, 400 MHz) 2,07-2,15 (m, 2H), 2,71 (t, 2H, J = 7,7 Hz), 3,12 (t, 2H, J = 7,6 Hz), 4,21 (d, 2H, J = 5,5 Hz), 6,85 (s, 1H), 7,15-7,31 (m, 5H), 8,55 (s, 1H), 9,84 (t, 1H, J = 5,5 Hz). 355 353
- 30
-
clorhidrato de ácido [(5ciclopentil-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen99 RMN 1H (DMSO-D6, 400 MHz) : 1,68-1,84 (m, 6H), 2,14-2,21 (m, 2H), 3,693,76 (m, 1H), 4,21 (d, 2H, J = 5,7 Hz), 6,83 (s, 1H), 8,56 (s, 1H), 9,85 (t, 1H, J = 5. 6 Hz) . 305 303
- 31
-
clorhidrato de ácido {[5(3-fluoro-5trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen100 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,37 (s, 1H), 7,99 (d, 1H, J = 9,3 Hz), 8,23 (d, 1H, J =9,3 Hz), 8,30 (s, 1H), 8,63 (s, 1H), 10,00 (t, 1H, J = 5,6 Hz). 399 397
78 [Tabla 7]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 32
-
clorhidrato de ácido {[5(4-fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen101 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,7 Hz), 7,14 (s, 1H), 7,41-7,48 (m, 2H), 8,078,13 (m, 2H), 8,59 (s, 1H), 9,97 (t, 1H, J = 5,7 Hz). 331 329
- 33
-
clorhidrato de ácido {[7hidroxi-5-(3trifluorometilfenil)[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen102 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,5 Hz), 7,28 (s, 1H), 7,84 (t, 1H, J = 7,9 Hz), 7,98 (d, 1H, J = 7,9 Hz), 8,28 (d, 1H, J = 7,9 Hz), 8,41 (s, 1H), 8,61 (s, 1H), 10,00 (t, 1H, J = 5,7 Hz). 381 379
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 34
-
clorhidrato de ácido {[5-(2-fluoro-5trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen103 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,28 (s, 1H), 7,73 (dd, 1H, J = 9,1, 9,1 Hz), 8,10 (ddd, 1H, J = 9,1, 4,5, 2,0 Hz), 8,24 (dd, 1H, J = 6,4, 2,0 Hz), 8,57 (s, 1H), 9,95 (t, 1H, J = 5,6 Hz). 39,9 397
- 35
-
clorhidrato de ácido [(7-hidroxi-5-isopropil[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen104 RMN 1H (DMSO-D6, 400 MHz) : 1,37 (d, 6H, J = 7,3 Hz), 3,67 (sept, 1H, J = 7,3 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,82 (s, 1H), 8,59 (s, 1H), 9,84 (t, 1H, J = 5,6 Hz). 279 277
79 [Tabla 8]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 36
-
clorhidrato de ácido {[5-(3-cloro-5trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen105 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,37 (s, 1H), 8,14 (s, 1H), 8,37 (s, 1H), 8,41 (s, 1H), 8,62 (s, 1H), 9,99 (t, 1H, J = 5,6 Hz). 415 413
- 37
-
clorhidrato de ácido {[5-(3-cianofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino)acético
imagen106 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,7 Hz), 7,28 (s, 1H), 7,81 (t, 1H, J = 7,9 Hz), 8,08 (dt, 1H, J = 7,9, 1,0 Hz), 8,34 (d, 1H, J = 8,4 Hz), 8,48 (t, 1H, J = 1,3 Hz), 8,61 (s, 1H), 9,99 (t, 1H, J = 5,7 Hz). 338 336
- 38
-
clorhidrato de ácido ({5-[2-(4-ciclopropilfenil)etil]-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil}amino)acético
imagen107 RMN 1H (DMSO-D6, 400 MHz) : 0,59-0,64 (m, 2H), 0,88-0,93 (m, 2H), 1,831,90 (m, 1H), 3,06 (t, 2H, J = 7,9 Hz), 3,37 (t, 2H, J = 7,9 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,81 (s, 1H), 6,99 (d, 2H, J = 8,1 Hz), 7,11 (d, 2H, J = 8,1 Hz), 8,60 (s, 1H), 9,84 (t, 1H, J = 5,6 Hz). 381 379
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 39
-
clorhidrato de ácido {[5-(2,2-dimetil-propil)7-hidroxi-[1,2,4]triazolo[1,5-a)piridin-8carbonil]-amino}acético
imagen108 RMN 1H (DMSO-D6, 400 MHz) : 0,97 (s, 9H), 3,12 (s, 2H), 4,21 (d, 2H, J = 5,6 Hz), 6,78 (s, 1H), 8,53 (s, 1H), 9,88 (t, 1H, J = 5,6 Hz). 307 305
80 81 [Tabla 9]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 40
-
clorhidrato de ácido {[5-(1-etilpropil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen109 RMN 1H (DMSO-D6, 400 MHz) : 0,78 (t, 6H, J = 7,3 Hz), 1,72-1,94 (m, 4H), 3,373,48 (m, 1H), 4,21 (d, 2H, J = 5,6 Hz), 6,85 (s, 1H), 8,55 (s, 1H), 9,88 (t, 1H, J = 5,6 Hz). 307 305
- 41
-
clorhidrato de ácido {[5-(3-cloro-5fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen110 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,8 Hz), 7,28 (s, 1H), 7,73 (dt, 1H, J = 8,7, 2,1 Hz), 7,88-7,91 (m, 1H), 7,98-8,00 (m, 1H), 8,60 (s, 1H), 9,97 (t, 1H, J = 5,6 Hz). 365 363
- 42
-
clorhidrato de ácido {[5-(3-fluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen111 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,5 Hz), 7,21 (s, 1H), 7,47 (tdd, 1H, J = 8,6, 2,6, 0,7 Hz), 7,64 (td, 1H, J = 8,1, 6,0 Hz), 7,87 (dt, 1H, J = 7,8, 1,0 Hz), 7,90 (dt, 1H, J = 10,1, 2,1 Hz), 8,60 (s, 1H), 9,99 (t, 1H, J = 5,4 Hz). 331 329
- 43
-
ácido [(7-hidroxi-5isobutil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen112 RMN 1H (DMSO-D6, 400 MHz) : 0,94 (d, 6H, J = 6,9 Hz), 2,28 (tsept, 1H, J = 6,9, 7,3 Hz), 2,98 (d, 2H, J = 7,3 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,85 (s, 1H), 8,55 (s, 1H), 9,85 (t, 1H, J = 5,6 Hz). 293 291
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 44
-
ácido {[5-(3-clorofenil)7-hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen113 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,22 (s, 1H), 7,59-7,71 (m, 2H), 7,96 (d, 1H, J = 7,7 Hz), 8,11 (s, 1H), 8,59 (s, 1H), 9,98 (s a, 1H), 12,99 (s a, 1H), 14,38 (s a, 1H). 347, 349 345, 347
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 45
-
clorhidrato de ácido {[5-(2-etilbutil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen114 RMN 1H (DMSO-D6, 400 MHz) : 0,85 (t, 6H, J = 7,4 Hz), 1,25-1,39 (m, 4H), 1,942,02 (m, 1H), 3,03 (d, 2H, J = 7,3 Hz), 4,21 (d, 2H, J = 5,5 Hz), 6,87 321 319
- (s, 1H), 8,56 (s, 1H), 9,85 (t, 1H, J = 5,5 Hz).
- 46
-
clorhidrato de ácido {[5-(3,5-diclorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen115 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 3H, J = 5,6 Hz), 7,30 (s, 1H), 7,89 (t, 1H, J = 3,5 Hz), 8,08 (s, 1H), 8,09 (s, 1H), 8,61 (s, 1H), 9,99 (t, 1H, J = 5,6 Hz). 381, 383 379, 381
- 47
-
clorhidrato de ácido {[5-(2-ciclopropiletil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen116 RMN 1H (DMSO-D6, 400 MHz) : 0,00-0,05 (2H, m), 0,35-0,42 (2H, m), 0,720,81 (1H, m), 1,64-1,73 (2H, m), 3,15-3,21 (2H, m), 4,20 (2H, d, J = 5,6 Hz), 6,86 (1H, s), 8,55 (1H, s), 9,79-9,87 (1H, m). 305 303
82 [Tabla 10]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 48
-
clorhidrato de ácido {[5-(3,3-dimetilpentil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen117 RMN 1H (CD3OD, 400 MHz) : 0,91 (t, 3H, J = 7,6 Hz), 0,98 (s, 6H), L,39 (q, 2H, J = 7,5 Hz), L,70 (ddd, 2H, J = 8,7, 4,7, 3,8 Hz), 3,083,14 (m, 2H), 4,24 (s, 2H), 5,82 (s, 1H), 3,54 (s, 1H). 335 333
- 49
-
clorhidrato de ácido {[7-hidroxi-5-(3,4,5trifluorofenil)-[1,2,4]triazolo[1,5-a]piridin-8carboxil]-amino}acético
imagen118 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,5 Hz), 7,28 (s, 1H), 3,09 (dd, 2H, J = 9,0, 6,8 Hz), 8,62 (s, 1H), 9,98 (t, 1H, J = 5,1 Hz). 367 365
- 50
-
clorhidrato de ácido {[5-(4-clorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen119 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,17 (s, 1H), 7,67 (d, 2H, J = 8,6 Hz), 8,05 (d, 2H, J = 8,6 Hz), 8,59 (s, 1H), 9,98 (t, 1H, J = 5,6 Hz). 347 345
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 51
-
clorhidrato de ácido [(7-hidroxi-5-(mtolil)[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen120 RMN 1H (DMSO-D6, 400 MHz) : 2,42 (3H, s), 4,24 (2H, d, J = 5,6 Hz), 7,09 (1H, s), 7,41-7,51 (2H, m), 7,78-7,84 (2H, m), 8,58 (1H, s), 9,98 (1H, t, J = 5,6 Hz). 327 325
83 84 [Tabla 11]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 52
-
clorhidrato de ácido {[5-(3-ciclopropil-5fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen121 RMN 1H (DMSO-D6, 400 MHz) : 0,82-0,86 (m, 2H), 1,01-1,06 (m, 2H), 2,032,10 (m, 1H), 4,24 (d, 2H, J = 5,6 Hz), 7,15-7,18 (m, 1H), 7,20 (s, 1H), 7,56 (dd, 1H, J = 1,4, 1,4 Hz), 7,627,65 (m, 1H), 8,59 (s, 1H), 9,98 (t, 1H, J = 5,6 Hz). 371 369
- 53
-
clorhidrato de ácido [(5-ciclobutilmetil-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen122 RMN 1H (DMSO-D6, 400 MHz) : 1,72-1,90 (m, 4H), 1,98-2,10 (m, 2H), 2,802,92 (m, 1H), 3,20 (d, 2H, J = 7,4 Hz), 4,20 (d, 2H, J = 5,6 Hz), 6,79 305 303
- (s, 1H), 8,55 (s, 1H), 9,83 (t, 1H, J = 5,6 Hz).
- 54
-
clorhidrato de ácido {[5-(2-ciclobutil-etil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen123 RMN 1H (DMSO-D6, 400 MHz) : 1,54-1,67 (m, 2H), 1,72-1,92 (m, 4H), 1,952,06 (m, 2H), 2,26-2,37 (m, 1H), 3,00 (t, 2H, J = 7,7 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,85 (s, 1H), 8,56 (s, 1H), 9,85 (t, 1H, J = 5,6 Hz). 319 317
- 55
-
clorhidrato de ácido {[5-(2-fluoro-3trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen124 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (2H, d, J = 5,6 Hz), 7,25 (1H, s), 7,61-7,68 (1H, m), 8,03-8,13 (2H, m), 8,57 (1H, s), 9,87-10,01 (1H, m). 399 397
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 56
-
clorhidrato de ácido {[5(3-cloro-2-fluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen125 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (2H, d, J = 5,6 Hz), 7,21 (1H, s), 7,47 (1H, dd, J = 7,9, 3,9 Hz), 7,73 (1H, dd, J = 7,1, 3,5 Hz), 7,88 (1H, dd, J = 7,7, 365 363
- 3,8 Hz), 8,56 (1H, s), 9,95 (1H, t, J = 5,0 Hz).
- 57
-
clorhidrato de ácido {[7hidroxi-5-(4trifluorometilfenil)[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen126 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (2H, d, J = 5,6 Hz), 7,23 (1H, s), 7,96 (2H, d, J = 8,1 Hz), 8,21 (2H, d, J = 8,1 Hz), 8,59 (1H, s), 9,99 (1H, t, J = 5,3 Hz). 381 379
- 58
-
clorhidrato de ácido [(5cicloheptil-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen127 RMN 1H (DMSO-D6, 400 MHz) : 1,52-1,86 (m, 10H), 1,96-2,04 (m, 2H), 3,503,59 (m, 1H), 4,21 (d, 2H, J = 5,5 Hz), 6,78 (s, 1H), 8,56 (s, 1H), 9,86 (t, 1H, J = 5,5 Hz). 333 331
- 59
-
clorhidrato de ácido {[5(2,3-difluoro-fenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen128 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,7 Hz), 7,20 (s, 1H), 7,45 (tdd, 1H, J = 8,2, 4,9, 1,4 Hz), 7,59 (ddt, 1H, J = 8,3, 5,4, 1,2 Hz), 7,70-7,77 (m, 1H), 8,56 (s, 1H), 9,95 (t, 1H, J = 5,6 Hz). 349 347
85 [Tabla 12]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 60
-
clorhidrato de ácido {[5(2-ciclopentiletil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen129 RMN 1H (DMSO-D6, 400 MHz) : 1,11-1,19 (m, 2H), 1,47-1,61 (m, 4H), 1,741,87 (m, 5H), 3,10 (t, 2H, J = 7,5 Hz), 4,21 (d, 2H, J = 5,6 Hz), 6,87 (s, 1H), 8,56 (s, 1H), 9,84 (t, 1H, J = 5,6 Hz). 333 331
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 61
-
clorhidrato de ácido {[5-(2-fluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen130 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,13 (s, 1H), 7,41-7,48 (m, 2H), 7,667,72 (m, 1H), 7,74-7,78 (m, 1H), 8,55 (s, 1H), 9,95 (t, 1H, J = 5. 6 Hz) . 331 329
- 62
-
clorhidrato de ácido {[5-(4-cloro-2fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen131 RMN 1H, (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,2 Hz), 7,16 (s, 1H), 7,55 (dd, 1H, J = 8,1, 1,4 Hz), 7,74 (dd, 1H, J = 10,0, 1,4 Hz), 7,81 (dd, 1H, J = 8,1, 8,1 Hz), 8,56 (s, 1H), 9,94 (t, 1H, J = 5,2 Hz). 365 363
- 63
-
clorhidrato de ácido {[5-(4-fluorobencil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen132 RMN 1H (DMSO-D6, 400 MHz) : 4,20 (2H, d, J = 5,5 Hz), 4,46 (2H, s), 6,74 (1H, s), 7,16 (2H, dd, J = 8,9, 4,5 Hz), 7,45 (2H, dd, J = 8,6, 5,5 Hz), 8,57 (1H, s), 9,83 (1H, t, J = 5,4 Hz). 345 343
86 [Tabla 13]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 64
-
clorhidrato de ácido (R)-2-{[5-(3,5difluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}propiónico
imagen133 RMN 1H (DMSO-D6, 400 MHz) : 1,52 (d, 3H, J = 7,1 Hz), 4,58-4,67 (m, 1H), 7,28 (s a, 1H), 7,51-7,59 (m, 1H), 7,81 (d, 2H, J = 6,4 Hz), 8,62 (s, 1H), 10,08-10,15 (m a, 1H). 363 361
- 65
-
clorhidrato de ácido [(7-hidroxi-5propil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen134 RMN 1H (DMSO-D6, 400 MHz) : 0,97 (t, 3H, J = 7,4 Hz), 1,80 (tq, 2H, J = 7,4, 7,4 Hz), 3,07 (t, 2H, J = 7,4 Hz), 4,21 (d, 1H, J = 5,7 Hz), 6,85 (s, 1H), 8,56 (s, 1H), 9,84 (t, 1H, J = 5,7 Hz). 279 277
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 66
-
clorhidrato de ácido 2{[5-(3,5-difluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]amino}propiónico
imagen135 RMN 1H (DMSO-D6, 400 MHz) : 1,52 (d, 3H, J = 7,1 Hz), 4,58-4,67 (m, 1H), 7,28 (s a, 1H), 7,51-7,59 (m, 1H), 7,81 (d, 2H, J = 6,4 Hz), 8,62 (s, 1H), 10,08-10,15 (m a, 1H). 363 361
- 67
-
clorhidrato de ácido (S)-2-{[5-(3,5difluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}propiónico
imagen136 RMN 1H (DMSO-D6, 400 MHz) : 1,52 (d, 3H, J = 7,1 Hz), 4,60-4,67 (m, 1H), 7,31 (s, 1H), 7,56 (t, 1H, J = 9,3 Hz), 7,82 (d, 2H, J = 6,6 Hz), 8,61 (s, 1H), 10,10 (d, 1H, J = 6,6 Hz), 13,16 (s a, 1H), 14,32 (s, 1H). 363 361
87 [Tabla 14]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 68
- clorhidrato de ácido 2{[5-(3,5-difluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}-2metil-propiónico RMN 1H (DMSO-D6, 400 MHz) : 1,63 (s, 6H), 7,27 (s, 1H), 7,51-7,60 (m, 1H), 7,767,83 (m, 2H), 8,61 (s, 1H), 10,15 (s, 1H). 377 375
- 69
-
clorhidrato de ácido (S)-2-[(7-hidroxi-5fenetil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]propiónico
imagen137 RMN 1H (DMSO-D6, 400 MHz) : 1,49 (d, 3H, J = 7,3 Hz), 3,12 (t, 2H, J = 7,8 Hz), 3,41 (t, 2H, J = 7,8 Hz), 4,56-4,63 (m, 1H), 6,81 (s, 1H), 7,18-7,33 (m, 5H), 8,61 (s, 1H), 9,97 (d, 1H, J = 7,1 Hz). 355 353
- 70
-
clorhidrato de ácido (R)-2-[7(7-hidroxi-5fenetil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]propiónico
imagen138 RMN 1H (DMSO-D6, 400 MHz) : 1,49 (d, 3H, J = 7,3 Hz), 3,12 (t, 2H, J = 7,8 Hz), 3,41 (t, 2H, J = 7,8 Hz), 4,56-4,63 (m, 1H), 6,80 (s, 1H), 7,18-7,33 (m, 5H), 8,61 (s, 1H), 9,97 (d, 1H, J = 7,1 Hz). 355 353
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 71
-
clorhidrato de ácido [(7-hidroxi-6pentil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen139 RMN 1H (DMSO-D6, 400 MHz) : 0,87 (t, 3H, J = 6,9 Hz), 1,28-1,36 (m, 4H), 1,61 (t, 2H, J = 7,6 Hz), 2,62 (t, 2H, J = 7,6 Hz), 4,21 (d, 2H, J = 5,3 Hz), 8,50 (s, 1H), 8,88 (s, 1H), 9,93 (s, 1H), 14,81 (s, 1H). 307 305
88 89 [Tabla 15]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 72
-
clorhidrato de ácido {[7-hidroxi-5-(5-metiltiophen-2-il)[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen140 RMN 1H (DMSO-D6, 400 MHz) : 2,58 (s, 3H), 4,23 (d, 2H, J = 5,5 Hz), 7,07 (d, 1H, J = 3,7 Hz), 7,50 (s, 1H), 8,27 (d, 1H, J = 4,0 Hz), 8,67 (s, 1H), 9,859,90 (m a, 1H). 333 331
- 73
-
clorhidrato de ácido [(5-hexil-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen141 RMN 1H (DMSO-D6, 400 MHz) : 0,85 (3H, t, J = 7,0 Hz), 1,23-1,41 (6H, m), 1,711,81 (2H, m), 3,08 (2H, t, J = 7,7 Hz), 4,20 (2H, d, J = 5,6 Hz), 6,85 321 319
- (1H, s), 8,56 (1H, s), 9,79-9,86 (1H, m).
- 74
-
clorhidrato de ácido [(7-hidroxi-5pentil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen142 RMN 1H (DMSO-D6, 400 MHz) : 0,84-0,91 (m, 3H), 1,29-1,40 (m, 4H), 1,721,83 (m, 2H), 3,09 (t, 2H, J = 7,5 Hz), 4,21 (d, 2H, J = 5,4 Hz), 6,86 (s, 1H), 8,56 (s, 1H), 9,83 (t, 1H, J = 5,4 Hz). 307 305
- 75
- clorhidrato de ácido {[5-(2,5-difluorofenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,6 Hz), 7,19 (s, 1H), 7,49-7,60 (m, 2H), 7,677,73 (m, 1H), 8,56 (s, 1H), 9,95 (t, 1H, J = 5,6 Hz). 349 347
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 76
-
clorhidrato de ácido {[7-hidroxi-5-(2,3,5trifluorofenil)-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen143 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,5 Hz), 7,25 (s, 1H), 7,58-7,64 (m, 1H), 7,867,93 (m, 1H), 8,59 (s, 1H), 9,95 (t, 1H, J = 5,5 Hz). 367 365
- 77
-
clorhidrato de ácido {[5-(2,4-difluoro-fenil)7-hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen144 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,2 Hz), 7,14 (s, 1H), 7,30-7,39 (m, 1H), 7,507,60 (m, 1H), 7,81-7,89 (m, 1H), 8,55 (s, 1H), 9,94 (t, 1H, J = 5,4 Hz). 349 347
- 78
-
clorhidrato de ácido {[5-(4-cloro-3fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen145 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,6 Hz), 7,26 (s, 1H), 7,82-7,86 (m, 1H), 7,93 (dd, 1H, J = 8,5, 1,6 Hz), 8,13 (dd, 1H, J = 10,5, 2,0 Hz), 8,61 (s, 1H), 9,98 (t, 1H, J = 5,4 Hz). 365 363
- 79
-
clorhidrato de ácido {[5-(3-fluoro-5metilfenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen146 RMN 1H (DMSO-D6, 400 MHz) : 2,43 (s, 3H), 4,25 (d, 2H, J = 5,3 Hz), 7,18 (s, 1H), 7,32 (d, 1H, J = 9,3 Hz), 7,70 (d, 2H, J = 10,4 Hz), 3,60 (d, 1H, J = 0,7 Hz), 9,99 (t, 1H, J = 5,3 Hz). 345 343
- 80
-
clorhidrato de ácido [(6-cloro-7-hidroxi-5fenetil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen147 RMN 1H (DMSO-D6, 400 MHz) : 3,05 (t, 2H, J = 7,8 Hz), 3,56 (t, 2H, J = 7,8 Hz), 4,17 (d, 2H, J = 5,1 Hz), 7,16-7,22 (m, 3H), 7,237,29 (m, 2H), 8,60 (s, 1H). 375 373
90 [Tabla 16]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 81
-
clorhidrato de ácido [(6-cloro-7-hidroxi-5propil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen148 RMN 1H (DMSO-D6, 400 MHz) : 3,09 (t, 2H, J = 7,8 Hz), 3,28 (t, 2H, J = 7,8 Hz), 4,25 (d, 2H, J = 5,6 Hz), 7,16-7,32 (m, 5H), 7,36 (s, 1H), 8,68 (s, 1H), 10,42 (t, 1H, J = 5,6 Hz), 13,26 (s, 1H). 313 311
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 82
-
clorhidrato de ácido {[5-(4-ciclopropil-2fluorofenil)-7-hidroxi[1,2,4]-triazolo[1,5a]piridin-8-carbonil]amino}acético
imagen149 RMN 1H (DMSO-D6, 400 MHz) : 0,82-0,86 (m, 2H), 1,05-1,10 (m, 2H), 2,042,11 (m, 1H), 4,24 (d, 2H, J = 5,6 Hz), 7,06 (s, 1H), 7,14 (d, 1H, J = 8,1 Hz), 7,15 (d, 1H, J = 7,7 Hz), 371 369
- 7,62 (dd, 1H, J = 7,7, 7,7 Hz), 8,53 (s, 1H), 9,94 (t, 1H, J=5,6 Hz).
- 83
-
clorhidrato de ácido [(6-hidroxi-8fenil[1,2,4]triazolo[1,5a]piridin-5-carbonil)amino]acético
imagen150 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,5 Hz), 7,50-7,63 (m, 3H), 7,80 (s, 1H), 8,21 (d, 2H, J = 7,3 Hz), 8,74 (s, 1H), 10,53 (t, 1H, J = 5,5 Hz), 13,36 (s, 1H). 313 311
- 84
-
ácido {[8-(3-clorofenil)6-hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen151 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,6 Hz), 7,58-7,64 (m, 2H), 7,92 (s, 1H), 8,15-8,21 (m, 1H), 8,378,39 (m, 1H), 8,76 (s, 1H), 10,54 (t, 1H, J = 5,4 Hz), 13,06 (s, 1H), 13,36 (s, 1H). 347 345
91 [Tabla 17]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 85
-
clorhidrato de ácido {[8-(3,5-difluorofenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen152 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,6 Hz), 7,47 (tt, 1H, J = 9,3, 2,3 Hz), 8,03 (s, 1H), 8,06-8,14 (m, 2H), 8,78 (s, 1H), 10,54 (t, 1H, J = 5,4 Hz), 13,35 (s, 1H). 349 347
- 86
-
clorhidrato de ácido [(8-bencil-6-hidroxi[1,2,4]-triazolo[1,5a]piridin-5-carbonil)amino]acético
imagen153 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,6 Hz), 4,33 (s, 2H), 7,20-7,25 (m, 1H), 7,287,33 (m, 2H), 7,35 (s, 1H), 7,38-7,41 (m, 2H), 8,66 (s, 1H), 10,40 (t, 1H, J = 5,6 Hz), 13,27 (s, 1H). 327 325
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 87
-
clorhidrato de ácido [(6-hidroxi-8-fenetil[1,2,4]-triazolo[1,5a]piridin-5-carbonil)amino]acético
imagen154 RMN 1H (DMSO-D6, 400 MHz) : 3,09 (t, 2H, J = 7,8 Hz), 3,28 (t, 2H, J = 7,8 Hz), 4,25 (d, 2H, J = 5,6 Hz), 7,16-7,32 (m, 5H), 7,36 (s, 1H), 8,68 (s, 1H), 10,42 (t, 1H, J = 5,6 Hz), 13,26 (s, 1H). 341 339
- 88
-
ácido {[8-(2-clorofenil)6-hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen155 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,6 Hz), 7,49-7,59 (m, 2H), 7,607,63 (m, 2H), 7,67 (dd, 1H, J = 7,9, 1,4 Hz), 8,66 (s, 1H), 10,50 (t, 1H, J = 5,6 Hz), 13,06 (s, 1H), 13,37 (s, 1H). 347 345
92 93 [Tabla 18]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 89
-
clorhidrato de ácido {[8-(3,5-diclorofenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen156 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,3 Hz), 7,80 (t, 1H, J = 1,9 Hz), 8,03 (s, 1H), 8,36 (d, 2H, J = 1,8 Hz), 8,77 (s, 1H), 10,53 (t, 1H, J = 5,3 Hz), 13,34 (s, 1H). 381 379
- 90
-
clorhidrato de ácido ({8-[2-(4fluorofenil)etil]-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil}-amino)acético
imagen157 RMN 1H (DMSO-D6, 400 MHz) : 3,09 (t, 2H, J = 7,9 Hz), 3,27 (t, 2H, J = 7,7 Hz), 4,25 (d, 2H, J = 5,5 Hz), 7,10 (t, 2H, J = 8,9 Hz), 7,26 (dd, 2H, J = 8,7, 5,8 Hz), 7,35 (s, 1H), 8,66 (s, 1H), 10,42 (t, 1H, J=5,3 Hz), 13,26 (s, 1H). 359 357
- 91
-
clorhidrato de ácido [(8-ciclohexilmetil-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil)-amino]acético
imagen158 RMN 1H (DMSO-D6, 400 MHz) : 0,94-1,23 (m, 5H), 1,53-1,70 (m, 5H), 1,801,94 (m, 1H), 2,86 (d, 2H, J = 7,2 Hz), 4,25 (d, 2H, J = 5,6 Hz), 7,36 (s, 1H), 8,62 (s, 1H), 10,42 (t, 1H, J = 5,6 Hz), 13,28 (s, 1H). 333 331
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 92
-
clorhidrato de ácido [(8-ciclohexil-6-hidroxi[1,2,4]-triazolo[1,5a]piridin-5-carbonil)amino]acético
imagen159 RMN 1H (DMSO-D6, 400 MHz) : 1,23-1,34 (m, 1H), 1,38-1,49 (m, 2H), 1,571,67 (m, 2H), 1,73-1,77 (m, 1H), 1,82-1,86 (m, 2H), 1,911,96 (m, 2H), 3,15-3,22 (m, 1H), 4,25 (d, 2H, J=5,6 Hz), 7,33 (s, 1H), 8,63 (s, 1H), 10,42 (t, 1H, J=5,6 Hz), 13,29 (s, 1H). 319 317
- 93
-
clorhidrato de ácido [(8-ciclohex-1-enil-6hidroxil-[1,2,4]triazolo[1,5-a]piridin-5carbonil)-amino]acético
imagen160 RMN 1H (DMSO-D6, 400 MHz) : 1,62-1,68 (m, 2H), 1,74-1,80 (m, 2H), 2,312,35 (m, 2H), 2,49-2,54 (m, 2H), 4,25 (d, 2H, J = 5,6 Hz), 7,33 (s, 1H), 7,58-7,61 317 315
- (m, 1H), 8,66 (s, 1H), 10,48 (t, 1H, J = 5,6 Hz), 13,28 (s, 1H).
- 94
-
clorhidrato de ácido {[8-(3-cloro-4fluorofenil)-6-hidroxi[1,2,4]-triazolo[1,5a]piridin-5-carbonil]amino}acético
imagen161 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,5 Hz), 7,64 (t, 1H, J = 8,9 Hz), 7,94 (s, 1H), 8,29 (dq, 1H, J = 8,7, 2,3 Hz), 8,57 (dd, 1H, J = 7,2, 2,3 Hz), 8,77 (s, 1H), 365 363
- 10,52 (t, 1H, J = 5,5 Hz), 13,36 (s, 1H).
- 95
-
clorhidrato de ácido {[8-(3,4-diclorofenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen162 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,5 Hz), 7,84 (d, 1H, J = 8,4 Hz), 7,97 (s, 1H), 8,25 '(dd, 1H, J = 8,4, 2,2 Hz), 8,60 (d, 1H, J=2,2 Hz), 8,77 (s, 1H), 10,52 (t, 1H, J = 5,5 Hz), 13,35 (s, 1H). 381 379
94 [Tabla 19]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 96
-
clorhidrato de ácido {[8(5-clorotiofen-2-il)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen163 RMN 1H (DMSO-D6, 400 MHz) : 4,26 (d, 2H, J = 5,5 Hz), 7,35 (d, 1H, J = 4,2 Hz), 8,06 (s, 1H), 8,22 (d, 1H, J = 4,2 Hz), 8,78 (s, 1H), 10,41 (t, 1H, J = 5,5 Hz), 13,35 (s, 1H). 353 351
- 97
- clorhidrato de ácido {[8(3,5-bistrifluorometilfenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético RMN 1H (DMSO-D6, 400 MHz) : 4,29 (d, 2H, J = 5,5 Hz), 8,24 (s, 1H), 8,29 (s, 1H), 8,82 (s, 1H), 8,98 (s, 2H), 10,55 (t, 1H, J = 5,5 Hz), 13,36 (s, 1H). 449 447
- 98
-
clorhidrato de ácido {[8(2-ciclohexiletil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen164 RMN 1H (DMSO-D6, 400 MHz) : 0,85-1,34 (m, 6H), 1,53-1,82 (m, 7H), 2,94-3,02 (m, 2H), 4,25 (d, 2H, J = 5,6 Hz), 7,40 (s, 1H), 8,63 (s, 1H), 10,41 (t, 1H, J = 5,6 Hz), 13,28 (s, 1H). 347 345
- 99
-
clorhidrato de ácido {[8(2-ciclopentiletil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen165 RMN 1H (DMSO-D6, 400 MHz) : 1,07-1,22 (m, 2H), 1,41-1,65 (m, 4H), 1,70-1,86 (m, 5H), 2,93-3,02 (m, 2H), 4,25 (d, 2H, J = 5,6 Hz), 7,40 (s, 1H), 8,64 (s, 1H), 10,41 (t, 1H, J = 5,6 Hz), 13,28 (s, 1H). 333 331
95 [Tabla 20]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 100
-
clorhidrato de ácido ({6hidroxi-8-[2-(2trifluorometilfenil)etil][1, 2,4]triazolo[1,5a]piridin-5-carbonil}amino)acético
imagen166 RMN 1H (DMSO-D6, 400 MHz) : 3,21-3,35 (m, 4H), 4,25 (d, 2H, J = 5,6 Hz), 7,38 (s, 1H), 7,44 (t, 1H, J = 7,5 Hz), 7,56 (d, 1H, J = 7,7 Hz), 7,63 (t, 1H, J = 7,7 Hz), 7,70 (d, 1H, J = 7,5 Hz), 8,68 (s, 1H), 10,43 (t, 1H, J = 5,6 Hz), 13,28 (s, 1H). 409 407
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 101
-
clorhidrato de ácido ({6hidroxi-8-[2-(3trifluorometilfenil)etil][1, 2,4]triazolo[1,5a]piridin-5-carbonil}amino)acético
imagen167 RMN 1H (DMSO-D6, 400 MHz) : 3,20 (dd, 2H, J = 9,4, 6,5 Hz), 3,32 (dd, 2H, J = 9,4, 6,5 Hz), 4,25 (d, 2H, J = 5,6 Hz), 7,40 (s, 1H), 7,497,59 (m, 3H), 7,63 (s, 1H), 8,68 (s, 409 407
- 1H), 10,42 (t, 1H, J = 5,6 Hz), 13,27 (s, 1H).
- 102
-
clorhidrato de ácido ({6hidroxi-8-[2-(4trifluorometilfenil)etil][1, 2,4]triazolo[1,5a]piridin-5-carbonil}amino)acético
imagen168 RMN 1H (DMSO-D6, 400 MHz) : 3,17-3,24 (m, 2H), 3,28-3,36 (m, 2H), 4,25 (d, 2H, J = 5,6 Hz), 7,40 (s, 1H), 7,48 (d, 2H, J = 7,9 Hz), 7,65 (d, 2H, J = 7,9 Hz), 8,68 (s, 1H), 10,42 (t, 1H, J = 5,6 Hz), 13,27 (s, 1H). 409 407
96 [Tabla 21]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 103
-
clorhidrato de ácido {[8(3-cloro-5-ciclopropilfenil)-6-hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen169 RMN 1H (DMSO-D6, 400 MHz) : 0,84-0,90 (m, 2H), 1,01-1,06 (m, 2H), 2,03-2,10 (m, 1H), 4,28 (d, 2H, J = 5,4 Hz), 7,31 (dd, 1H, J = 1,8, 1,8 Hz), 7,83 (dd, 1H, J = 1,8, 1,8 Hz), 7,93 (s, 1H), 8,13 387 385
- (dd, 1H, J = 1,8, 1,8 Hz), 8,75 (s, 1H), 10,53 (t, 1H, J = 5,4 Hz), 13,35 (s, 1H).
- 104
-
clorhidrato de ácido {[8(3-fluoro-5trifluorometilfenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen170 RMN 1H (DMSO-D6, 400 MHz) : 4,29 (d, 2H, J = 5,5 Hz), 7,89 (d, 1H, J = 8,6 Hz), 8,12 (s, 1H), 8,46 (d, 1H, J = 8,6 Hz), 8,63 (s, 1H), 8,80 (s, 1H), 10,54 (t, 1H, J = 5,5 Hz), 13,36 (s, 1H). 399 397
- 105
-
clorhidrato de ácido {[8(3-cloro-5-fluorofenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen171 RMN 1H (DMSO-D6, 400 MHz) : 4,28 (d, 2H, J = 5,3 Hz), 7,62-7,67 (m, 1H), 8,03 (s, 1H), 8,13-8,19 (m, 1H), 8,31 (s, 1H), 8,78 (s, 1H), 10,54 (t, 1H, J = 5,3 Hz), 13,35 (s, 1H). 365 363
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 106
-
clorhidrato de ácido {[8(4-fluoro-3trifluorometilfenil)-6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen172 RMN 1H (DMSO-D6, 400 MHz) : 4,29 (d, 2H, J = 5,6 Hz), 7,717,80 (m, 1H), 8,03 (s, 1H), 8,56-8,63 (m, 1H), 8,73-8,82 (m, 2H), 10,53 (t, 1H, J = 5,6 Hz), 13,37 (s, 1H). 399 397
97 98 [Tabla 22]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 107
-
clorhidrato de ácido [(6hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil)-amino]acético
imagen173 RMN 1H (DMSO-D6, 400 MHz) : 4,27 (d, 2H, J = 5,3 Hz), 7,56 (d, 1H, J = 9,7 Hz), 8,09 (d, 1H, J = 9,7 Hz), 8,68 (s, 1H), 10,49 (t, 1H, J = 5,3 Hz), 13,29 (s a, 1H). 237 235
- 108
-
ácido {[8-(4-clorofenil)6-hidroxi-[1,2,4]triazolo[1,5-a]piridin-5carbonil)-amino}acético
imagen174 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,2 Hz), 7,627,67 (m, 2H), 7,86 (s, 1H), 8,26-8,31 (m, 2H), 8,74 (s, 1H), 347 345
- 10,53 (t, 1H, J = 5,2 Hz), 13,31 (s a, 1H).
- 109
-
clorhidrato de ácido ({8[2-(3,5-difluorofenil)etil]-6-hidroxi[1,2,4]-triazolo[1,5a]piridin-5-carbonil}amino)acético
imagen175 RMN 1H (DMSO-D6, 400 MHz) : 3,13 (t, 2H, J = 7,9 Hz), 3,30 (t, 2H, J = 7,9 Hz), 4,25 (d, 2H, J = 5,2 Hz), 6,987,08 (m, 3H), 7,40 (s, 1H), 8,67 (s, 1H), 10,42 (t, 1H, J = 5,2 Hz), 13,27 (s a, 1H). 377 375
- 110
-
clorhidrato de ácido {[6hidroxi-8-(3trifluorometilfenil)[1,2,4]triazolo[1,5-a]piridin-5carbonil]-amino}acético
imagen176 RMN 1H (DMSO-D6, 400 MHz) : 4,29 (d, 2H, J = 5,5 Hz), 7,82 (t, 1H, J = 7,9 Hz), 7,91 (d, 1H, J = 7,9 Hz), 8,00 (s, 1H), 8,48 (d, 1H, J = 7,9 Hz), 8,70 (s, 1H), 8,78 (s, 1H), 10,54 (t, 1H, J = 5,5 Hz), 13,36 (s a, 1H). 381 379
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 111
-
clorhidrato de ácido [(7-hidroxi-3,6-difenil[1,2,4]-triazolo[4,3a]piridin-8-carbonil)amino]acético
imagen177 RMN 1H (DMSO-D6, 400 MHz) : 4,09 (d, 2H, J = 5,5 Hz), 7,36-7,44 (m, 3H), 7,577,66 (m, 5H), 7,90 (d, 2H, J = 7,3 Hz), 8,00 (s, 1H), 10,56 (t, 1H, J = 389 387
- 5,3 Hz), 12,61 (s, 1H), 13,95 (s, 1H).
- 112
-
clorhidrato de ácido [(7-hidroxi-3-metil-6fenil[1,2,4]triazolo[4,3a]piridin-8-carbonil)amino]acético
imagen178 RMN 1H (DMSO-D6, 400 MHz) : 2,62 (s, 3H), 4,05 (d, 2H, J = 5,5 Hz), 7,39-7,46 (m, 3H), 7,63 (d, 2H, J = 6,8 Hz), 8,21 (s, 1H), 10,54 (t, 1H, J = 5,3 Hz), 12,58 (s, 1H), 13,44 (s, 1H). 327 325
- 113
-
ácido [(7-hidroxi-3fenil[1,2,4]triazolo[4,3a]piridin-8-carbonil)amino] acético
imagen179 RMN 1H (DMSO-D6, 400 MHz) : 4,06-4,24 (m, 2H), 6,47-6,74 (m, 1H), 7,587,71 (m, 3H), 7,78-7,89 (m, 2H), 7,99-8,42 (m, 1H), 9,9910,43 (m, 1H). 313 311
- 114
-
clorhidrato de ácido [(7-hidroxi-3-fenetil[1,2,4]-triazolo[4,3a]piridin-8-carbonil)amino]acético
imagen180 RMN 1H (DMSO-D6, 400 MHz) : 3,08 (t, 2H, J = 7,7 Hz), 3,28 (t, 2H, J = 7,7 Hz), 4,05 (d, 2H, J = 5,2 Hz), 6,46 (d, 1H, J = 7,3 Hz), 7,16-7,25 (m, 1H), 7,26-7,32 341 339
- (m, 4H), 8,19 (d, 1H, J = 7,3 Hz), 10,33 (s a, 1H), 13,52 (s a, 1H).
99 [Tabla 23]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 115
-
clorhidrato de ácido {[3-(2-ciclohexiletil)-7hidroxi-[1,2,4]triazolo[4,3-a]piridin-8carbonil]-amino}acético
imagen181 RMN 1H (DMSO-D6, 400 MHz) : 0,90-0,98 (m, 2H), 1,17-1,22 (m, 3H), 1,281,40 (m, 1H), 1,62-1,67 (m, 5H), 1,75-1,78 (m, 2H), 2,96 (t, 2H, J = 7,9 Hz), 4,04 (d, 2H, J = 5,2 Hz), 6,52 (d, 1H, J = 7,7 Hz), 8,21 (d, 1H, J=7,7 Hz), 10,28 (s a, 1H). 347 345
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 116
-
ácido [(7-hidroxi-5fenetil-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen182 RMN 1H (DMSO-D6, 400 MHz) : 3,12 (t, 2H, J = 7,9 Hz), 3,40 (t, 3H, J = 7,9 Hz), 4,22 (d, 2H, J = 5,2 Hz), 6,79 (s, 1H), 7,21-7,29 (m, 5H), 8,58 (s, 341 339
- 1H), 9,84 (t, 1H, J = 5,2 Hz), 12,97 (s, 1H), 14,22 (s, 1H).
- 117
-
ácido [(5-butil-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil)-amino]acético
imagen183 RMN 1H (DMSO-D6, 400 MHz) : 0,93 (t, 3H, J = 7,5 Hz), 1,33-1,44 (m, 2H), 1,711,80 (m, 2H), 3,10 (t, 2H, J = 7,5 Hz), 4,20 (d, 2H, J = 5,2 Hz), 6,85 293 291
- (s, 1H), 8,55 (s, 1H), 9,84 (s a, 1H), 14,26 (s a, 1H).
100 [Tabla 24]
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 118
-
ácido {[5-(3-fluoro-5trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen184 RMN 1H (DMSO-D6, 400 MHz) : 4,25 (d, 2H, J = 5,1 Hz), 7,39 (s, 1H), 7,99 (d, 1H, J = 8,6 Hz), 8,23 (d, 1H, J = 9,5 Hz), 8,31 (s, 1H), 8,62 (s, 1H), 9,98 399 397
- (s, 1H), 13,01 (s, 1H), 14,41 (s, 1H).
- 119
-
ácido [(7-hidroxi-5pentil[1,2,4]triazolo[1,5a]piridin-8-carbonil)amino]acético
imagen185 RMN 1H (DMSO-D6, 400 MHz) : 0,88 (t, 3H, J = 7,6 Hz), 1,28-1,40 (m, 4H), 1,731,83 (m, 2H), 3,09 (t, 2H, J = 7,6 Hz), 4,21 (d, 2H, J = 5,5 Hz), 6,85 (s, 1H), 8,54 (s, 1H), 9,84 (t, 1H, J = 5,5 Hz), 12,94 (s, 1H), 14,25 (s, 1H). 307 305
- Ej. nº
- nombre del compuesto fórmula estructural RMN 1H, ppm EM (M+H) EM (M-H)
- 120
-
ácido {[5-(3-clorofenil)7-hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen186 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (d, 2H, J = 5,3 Hz), 7,22 (s, 1H), 7,58-7,70 (m, 2H), 7,96 (d, 1H, J = 7,7 Hz), 8,11 (s, 1H), 8,59 (s, 1H), 9,97 (s, 1H), 14,38 (s, 1H). 347 345
- 121
-
ácido {[5-(4-fluoro-3trifluorometilfenil)-7hidroxi-[1,2,4]triazolo[1,5-a]piridin-8carbonil]-amino}acético
imagen187 RMN 1H (DMSO-D6, 400 MHz) : 4,24 (2H, d, J = 5,6 Hz), 7,30 (1H, s), 7,77 (1H, dd, J = 10,5, 9,3 Hz), 3,36-8,40 (1H, m), 8,47 (1H, d, J = 6,9 Hz), 3,60 (1H, s), 9,97 (1H, s a), 14,38 (1H, s a). 399 397
101
- Ej. nº
- CI50 (µM) o actividad inhibidora (%) a 30 µM in vitro
- 11
- 0,29
- 12
- 0,82
- 13
- 1,31
- 14
- 0,23
- 15
- 1,80
- 16
- 0,32
- 17
- 0,29
- 18
- 0,48
- 19
- 0,26
- 20
- 0,59
- 21
- 0,25
- 22
- 0,21
- 23
- 0,19
- 24
- 0,57
- 25
- 0,25
- 26
- 0,33
- 27
- 0,74
- 28
- 1,38
- 29
- 0,92
[Tabla 26]
- Ej. nº
- CI50 (µM) o actividad inhibidora (%) a 30 µM in vitro
- 30
- 0,98
- 31
- 0,80
- 32
- 0,38
- 33
- 0,46
- 34
- 0,43
- 35
- 0,88
- 36
- 0,72
- 37
- 0,20
- 38
- 0,59
- 39
- 1,25
- 40
- 0,87
- 41
- 0,26
104
[Tabla 30]
- Ej. nº
- CE50 (µM) o actividad de producción (%) a 30 µM in vitro
- 9,9
- 10,9
- 12,4
- 38 %
- 11,5
- 20,8
- 18,4
- 13,4
- 1 %
- 0 %
- 1 %
- 5 %
- 1 %
- 5,1
- 29,1
- 7,0
- 8,8
- 6,1
- 6,6
- 6,6
- 12,0
- 13,7
- 7,8
- 5,4
- 14,1
- 7,5
- 7,7
- 13,9
- 11,3
108 [Tabla 31]
- Ej. nº
- CE50 (µM) o actividad de producción (%) a 30 µM in vitro
- 30
- 15,4
- 31
- 12,1
- 32
- 15,6
- 33
- 10,1
- 34
- 15,0
- 35
- 43 %
- 36
- 10,5
- 37
- 11 %
- 38
- 8,7
- 39
- 22,3
- 40
- 17,7
- 41
- 9,1
- 42
- 14,2
- 43
- 23,6
- 44
- 10,4
- 45
- 9,9
- 46
- 4,8
- 47
- 12,0
- 48
- 4,5
- 49
- 11,7
- 50
- 5,6
- 51
- 9,1
- 52
- 10,4
- 53
- 8,9
- 54
- 4,5
- 55
- 8,9
- 56
- 8,4
- 57
- 4,7
- 58
- 4,7
109 [Tabla 32]
- Ej. nº
- CE50 (µM) o actividad de producción (%) a 30 µM in vitro
- 59
- 49 %
- 60
- 8,4
- 61
- 28,8
- 62
- 10,1
- 63
- 19,7
- 64
- 0 %
- 65
- 49 %
- 66
- 21,1
- 67
- 14,3
- 68
- 0 %
- 69
- 12,0
- 70
- 1 %
- 71
- 15,8
- 72
- 4,0
- 73
- 34 %
- 74
- 8,3
- 75
- 23,7
- 76
- 18,0
- 77
- 18,7
- 78
- 6,6
- 79
- 7,8
- 80
- 23,3
- 81
- 33 %
- 82
- 5,4
- 83
- 20,7
- 84
- 11,0
- 85
- 20,6
- 86
- 6 %
- 87
- 18,5
110 [Tabla 33]
- Ej. nº
- CE50 (µM) o actividad de producción (%) a 30 µM in vitro
- 88
- 14 %
- 89
- 4,2
- 90
- 16,6
- 91
- 43 %
- 92
- 18,5
- 93
- 16,0
- 94
- 9,7
- 95
- 4,3
- 96
- 5,9
- 97
- 3,5
- 98
- 25,6
- 99
- 20,2
- 100
- 18,0
- 101
- 6 %
- 102
- 16,0
- 103
- 6,9
- 104
- 6,3
- 105
- 5,9
- 106
- 6,0
- 107
- 4 %
- 108
- 8,9
- 109
- 13,7
- 110
- 6,5
- 111
- 0 %
- 112
- 0 %
- 113
- 0 %
- 114
- 0 %
- 115
- 0 %
[Tabla 34]
- Ej. nº
- EC50 (µM) o actividad de producción (%) a 30 µM in vitro
- 116
- 5,6
- 117
- 7,7
111
Claims (1)
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imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 imagen7 imagen8 imagen9
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PCT/JP2010/062037 WO2011007856A1 (ja) | 2009-07-17 | 2010-07-16 | トリアゾロピリジン化合物、ならびにそのプロリル水酸化酵素阻害剤およびエリスロポエチン産生誘導剤としての作用 |
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