MX2011002899A - Compuestos de amida utiles en terapia. - Google Patents
Compuestos de amida utiles en terapia.Info
- Publication number
- MX2011002899A MX2011002899A MX2011002899A MX2011002899A MX2011002899A MX 2011002899 A MX2011002899 A MX 2011002899A MX 2011002899 A MX2011002899 A MX 2011002899A MX 2011002899 A MX2011002899 A MX 2011002899A MX 2011002899 A MX2011002899 A MX 2011002899A
- Authority
- MX
- Mexico
- Prior art keywords
- carboxamide
- pyrazole
- cyanophenyl
- isopropyl
- cyclopropyl
- Prior art date
Links
- -1 Amide compounds Chemical class 0.000 title claims description 184
- 238000002560 therapeutic procedure Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 607
- 238000002360 preparation method Methods 0.000 claims abstract description 271
- 238000000034 method Methods 0.000 claims abstract description 196
- 239000000203 mixture Substances 0.000 claims abstract description 132
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 60
- 238000011282 treatment Methods 0.000 claims abstract description 44
- 125000001424 substituent group Chemical group 0.000 claims abstract description 39
- 239000012453 solvate Substances 0.000 claims abstract description 38
- 201000009273 Endometriosis Diseases 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 206010046798 Uterine leiomyoma Diseases 0.000 claims abstract description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 23
- 201000010260 leiomyoma Diseases 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 107
- 229920006395 saturated elastomer Polymers 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 208000024891 symptom Diseases 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 19
- 208000000450 Pelvic Pain Diseases 0.000 claims description 18
- 208000026310 Breast neoplasm Diseases 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 206010006187 Breast cancer Diseases 0.000 claims description 13
- 102000003998 progesterone receptors Human genes 0.000 claims description 12
- 108090000468 progesterone receptors Proteins 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 208000004483 Dyspareunia Diseases 0.000 claims description 11
- 230000001684 chronic effect Effects 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 208000007106 menorrhagia Diseases 0.000 claims description 10
- 208000005641 Adenomyosis Diseases 0.000 claims description 9
- 201000009274 endometriosis of uterus Diseases 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 7
- 206010033128 Ovarian cancer Diseases 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 230000002611 ovarian Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- 206010014733 Endometrial cancer Diseases 0.000 claims description 6
- 230000008901 benefit Effects 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 210000000481 breast Anatomy 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003981 vehicle Substances 0.000 claims description 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- BGJBWNKGIONRMZ-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-(2-hydroxy-2-methylpropyl)-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC1=C(C(=O)NCC(C)(C)O)N(C(C)C)N=C1C1=CC=C(C#N)C(C)=C1 BGJBWNKGIONRMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- SDZICSPVYMXOSB-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-(2-hydroxy-2-methylpropyl)pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NCC(C)(C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 SDZICSPVYMXOSB-UHFFFAOYSA-N 0.000 claims description 3
- OSKNGWSQLJMACL-UHFFFAOYSA-N 4-benzyl-5-(4-cyanophenyl)-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC)=C1CC1=CC=CC=C1 OSKNGWSQLJMACL-UHFFFAOYSA-N 0.000 claims description 3
- YIAGHWLJXSQTNF-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC(C)C)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 YIAGHWLJXSQTNF-UHFFFAOYSA-N 0.000 claims description 3
- YEWVTHULFRGMBO-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(C#N)=C1C(=O)NC1CC1 YEWVTHULFRGMBO-UHFFFAOYSA-N 0.000 claims description 3
- HSPGZCZZFFLAIW-ZDUSSCGKSA-N 5-(4-cyano-3-methylphenyl)-n-[(2s)-2-hydroxypropyl]-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@@H](O)C)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 HSPGZCZZFFLAIW-ZDUSSCGKSA-N 0.000 claims description 3
- UWCYXOGMFRIUGH-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n,4-dimethylpyrazole-3-carboxamide Chemical compound CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UWCYXOGMFRIUGH-UHFFFAOYSA-N 0.000 claims description 3
- QCNXVNKVIAVYEC-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-cyclopropyl-4-methylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 QCNXVNKVIAVYEC-UHFFFAOYSA-N 0.000 claims description 3
- SIVWFSCCEFCZGK-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-4-methyl-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 SIVWFSCCEFCZGK-UHFFFAOYSA-N 0.000 claims description 3
- FBYQOMWMZAJYSY-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-(2-hydroxy-2-methylpropyl)-4-methylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 FBYQOMWMZAJYSY-UHFFFAOYSA-N 0.000 claims description 3
- LSKWDBADKXIQFN-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC(C)C)=C1C1CC1 LSKWDBADKXIQFN-UHFFFAOYSA-N 0.000 claims description 3
- WCXVUYXIGPFOGB-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-cyclopropylethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1CCNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 WCXVUYXIGPFOGB-UHFFFAOYSA-N 0.000 claims description 3
- VCVJJXWOLOJNJU-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-hydroxy-2-methylpropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 VCVJJXWOLOJNJU-UHFFFAOYSA-N 0.000 claims description 3
- VJQZKDYGAKVNHM-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(3-methoxypropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCCCOC)=C1C1CC1 VJQZKDYGAKVNHM-UHFFFAOYSA-N 0.000 claims description 3
- PMFFJQNIINPWNE-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(oxolan-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1COCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 PMFFJQNIINPWNE-UHFFFAOYSA-N 0.000 claims description 3
- AOHXXMCSOZRHPR-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC)=C1C1CC1 AOHXXMCSOZRHPR-UHFFFAOYSA-N 0.000 claims description 3
- JHNKPVKQRMPQAS-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC)=C1C1CC1 JHNKPVKQRMPQAS-UHFFFAOYSA-N 0.000 claims description 3
- FCLJBNPOXFMTPP-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-ethyl-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC(C)C)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 FCLJBNPOXFMTPP-UHFFFAOYSA-N 0.000 claims description 3
- QPVDZLPTLGDRPO-UHFFFAOYSA-N 5-(4-cyanophenyl)-n,2-dicyclopropyl-4-methylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 QPVDZLPTLGDRPO-UHFFFAOYSA-N 0.000 claims description 3
- YZDIBZSBRCJEEL-UHFFFAOYSA-N 5-(4-cyanophenyl)-n,4-diethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 YZDIBZSBRCJEEL-UHFFFAOYSA-N 0.000 claims description 3
- RDCCZYHLSAKEIS-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(cyclopropylmethyl)-4-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC=1C(C=2C=CC(=CC=2)C#N)=NN(C(C)C)C=1C(=O)NCC1CC1 RDCCZYHLSAKEIS-UHFFFAOYSA-N 0.000 claims description 3
- OZSSUUDDOJZMMU-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-cyclobutyl-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 OZSSUUDDOJZMMU-UHFFFAOYSA-N 0.000 claims description 3
- WHQQUTRCBTUYPN-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-cyclopropyl-4-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC=1C(C=2C=CC(=CC=2)C#N)=NN(C(C)C)C=1C(=O)NC1CC1 WHQQUTRCBTUYPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- BYHDNQBLRHQLBA-UHFFFAOYSA-N n-(1-acetylazetidin-3-yl)-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(C)=O)CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 BYHDNQBLRHQLBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- QMOWKNTVESEZCI-ARLHGKGLSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[(2r)-2-hydroxypropyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC[C@@H](C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 QMOWKNTVESEZCI-ARLHGKGLSA-N 0.000 claims description 2
- QMOWKNTVESEZCI-KZUDCZAMSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[(2s)-2-hydroxypropyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC[C@H](C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 QMOWKNTVESEZCI-KZUDCZAMSA-N 0.000 claims description 2
- OTODJUJPEZDJAD-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[2-(methylamino)-2-oxoethyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NCC(=O)NC)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 OTODJUJPEZDJAD-UHFFFAOYSA-N 0.000 claims description 2
- FFPYOXYDFNUAFY-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-methylpyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 FFPYOXYDFNUAFY-UHFFFAOYSA-N 0.000 claims description 2
- ITEZWOJCRBHRKD-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC(C)C)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 ITEZWOJCRBHRKD-UHFFFAOYSA-N 0.000 claims description 2
- GPGOMDBNUDLLIK-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-n,4-diethylpyrazole-3-carboxamide Chemical compound CCC(C)N1C(C(=O)NCC)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 GPGOMDBNUDLLIK-UHFFFAOYSA-N 0.000 claims description 2
- XRKVQHBODOBNNB-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-n-(cyclopropylmethyl)-4-ethylpyrazole-3-carboxamide Chemical compound CCC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(CC)=C1C(=O)NCC1CC1 XRKVQHBODOBNNB-UHFFFAOYSA-N 0.000 claims description 2
- COQQZKHXBCBTTJ-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-n-cyclopropyl-4-ethylpyrazole-3-carboxamide Chemical compound CCC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(CC)=C1C(=O)NC1CC1 COQQZKHXBCBTTJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- LGAQXDXWEYTAGV-UHFFFAOYSA-N 4-benzyl-5-(4-cyanophenyl)-n-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1CC1=CC=CC=C1 LGAQXDXWEYTAGV-UHFFFAOYSA-N 0.000 claims description 2
- VDSNWLNCUOGZBC-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 VDSNWLNCUOGZBC-UHFFFAOYSA-N 0.000 claims description 2
- XBTGKQAYTSXSFW-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 XBTGKQAYTSXSFW-UHFFFAOYSA-N 0.000 claims description 2
- RSLGKBCEJSCKQG-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-4-methyl-n-[2-(methylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC(=O)NC)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 RSLGKBCEJSCKQG-UHFFFAOYSA-N 0.000 claims description 2
- HSPGZCZZFFLAIW-CYBMUJFWSA-N 5-(4-cyano-3-methylphenyl)-n-[(2r)-2-hydroxypropyl]-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@H](O)C)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 HSPGZCZZFFLAIW-CYBMUJFWSA-N 0.000 claims description 2
- QVADJKYRFUVAIF-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-cyclopropyl-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=C(C)C(C#N)=CC=2)C(C)=C1C(=O)NC1CC1 QVADJKYRFUVAIF-UHFFFAOYSA-N 0.000 claims description 2
- TZPWEISEDROZNX-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-(2-hydroxy-2-methylpropyl)-4-methylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 TZPWEISEDROZNX-UHFFFAOYSA-N 0.000 claims description 2
- YOQBZXHUZVMUNY-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-(cyclopropylmethyl)-4-methylpyrazole-3-carboxamide Chemical compound C1CC1CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 YOQBZXHUZVMUNY-UHFFFAOYSA-N 0.000 claims description 2
- UMIUTNHZINBZSD-GFCCVEGCSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-[(2r)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UMIUTNHZINBZSD-GFCCVEGCSA-N 0.000 claims description 2
- UMIUTNHZINBZSD-LBPRGKRZSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-[(2s)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UMIUTNHZINBZSD-LBPRGKRZSA-N 0.000 claims description 2
- MPOJUMRSSPODEY-NSHDSACASA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-[(2s)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 MPOJUMRSSPODEY-NSHDSACASA-N 0.000 claims description 2
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- VQECVCDXYDUCNV-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-(3,3-difluorocyclobutyl)-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC)=C1C1CC(F)(F)C1 VQECVCDXYDUCNV-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9790208P | 2008-09-18 | 2008-09-18 | |
| PCT/IB2009/054038 WO2010032200A1 (en) | 2008-09-18 | 2009-09-16 | Amide compounds useful in therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2011002899A true MX2011002899A (es) | 2011-04-11 |
Family
ID=41269630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2011002899A MX2011002899A (es) | 2008-09-18 | 2009-09-16 | Compuestos de amida utiles en terapia. |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8232269B2 (enExample) |
| EP (1) | EP2350017A1 (enExample) |
| JP (1) | JP2012502975A (enExample) |
| KR (1) | KR20110044304A (enExample) |
| CN (1) | CN102159548A (enExample) |
| AP (1) | AP2011005611A0 (enExample) |
| AU (1) | AU2009294290B2 (enExample) |
| BR (1) | BRPI0918935A2 (enExample) |
| CA (1) | CA2735931A1 (enExample) |
| CL (1) | CL2011000570A1 (enExample) |
| CO (1) | CO6351734A2 (enExample) |
| DO (1) | DOP2011000083A (enExample) |
| EA (1) | EA201100368A1 (enExample) |
| EC (1) | ECSP11010901A (enExample) |
| IL (1) | IL211479A0 (enExample) |
| MA (1) | MA32642B1 (enExample) |
| MX (1) | MX2011002899A (enExample) |
| PE (1) | PE20110793A1 (enExample) |
| WO (1) | WO2010032200A1 (enExample) |
| ZA (1) | ZA201102690B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5964407B2 (ja) * | 2011-04-21 | 2016-08-03 | オリオン コーポレーション | アンドロゲン受容体調節カルボキシアミド |
| EP2734042B1 (en) * | 2011-07-21 | 2017-02-01 | The Regents Of The University Of California | Targeting gli proteins in human cancer by small molecules |
| US9416109B2 (en) | 2012-02-17 | 2016-08-16 | Eisai R&D Management Co., Ltd. | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
| EP2700635A1 (en) | 2012-08-20 | 2014-02-26 | Basf Se | 5-Trifluoromethylpyrazole amides having herbicidal activity |
| WO2014116651A1 (en) | 2013-01-23 | 2014-07-31 | The Regents Of The University Of California | Targeting gli proteins in human cancer by small molecules |
| EA027879B1 (ru) | 2013-02-22 | 2017-09-29 | Пфайзер Инк. | ПРОИЗВОДНЫЕ ПИРРОЛО[2,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-РОДСТВЕННЫХ КИНАЗ (JAK) |
| WO2014143617A1 (en) * | 2013-03-14 | 2014-09-18 | Teva Women's Health, Inc. | Deuterium-enriched tanaproget and processes for its preparation |
| WO2016024185A1 (en) | 2014-08-12 | 2016-02-18 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidine derivatives useful for inhibiting janus kinase |
| US20190321363A1 (en) * | 2016-06-20 | 2019-10-24 | Dr. Reddy's Laboratories Limited | Process for the preparation of elagolix sodium and its polymorph |
| CN108623446A (zh) * | 2017-03-24 | 2018-10-09 | 北京艾德旺科技发展有限公司 | 一种合成3，3-二氟环丁烷甲酸的方法 |
| EP3946606B1 (en) | 2019-03-27 | 2025-01-01 | Insilico Medicine IP Limited | Bicyclic jak inhibitors and uses thereof |
| EP4053124A1 (en) * | 2019-10-28 | 2022-09-07 | Shanghai Institute of Materia Medica, Chinese Academy of Sciences | Five-membered heterocyclic oxocarboxylic acid compound and medical use thereof |
| WO2023217203A2 (zh) * | 2022-05-12 | 2023-11-16 | 西北农林科技大学 | 二苯基吡唑类化合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2604218A1 (en) * | 2005-04-20 | 2006-10-26 | Pfizer Limited | Pyrazole derivatives as progesterone receptor antagonists |
| CA2623327A1 (en) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
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2009
- 2009-09-16 KR KR1020117006161A patent/KR20110044304A/ko not_active Ceased
- 2009-09-16 JP JP2011527444A patent/JP2012502975A/ja not_active Withdrawn
- 2009-09-16 EA EA201100368A patent/EA201100368A1/ru unknown
- 2009-09-16 CN CN2009801364939A patent/CN102159548A/zh active Pending
- 2009-09-16 CA CA2735931A patent/CA2735931A1/en not_active Abandoned
- 2009-09-16 MX MX2011002899A patent/MX2011002899A/es not_active Application Discontinuation
- 2009-09-16 PE PE2011000628A patent/PE20110793A1/es not_active Application Discontinuation
- 2009-09-16 AU AU2009294290A patent/AU2009294290B2/en not_active Expired - Fee Related
- 2009-09-16 BR BRPI0918935A patent/BRPI0918935A2/pt not_active IP Right Cessation
- 2009-09-16 EP EP09787204A patent/EP2350017A1/en not_active Withdrawn
- 2009-09-16 AP AP2011005611A patent/AP2011005611A0/xx unknown
- 2009-09-16 WO PCT/IB2009/054038 patent/WO2010032200A1/en not_active Ceased
- 2009-09-17 US US12/561,398 patent/US8232269B2/en not_active Expired - Fee Related
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2011
- 2011-02-28 IL IL211479A patent/IL211479A0/en unknown
- 2011-03-17 DO DO2011000083A patent/DOP2011000083A/es unknown
- 2011-03-17 CL CL2011000570A patent/CL2011000570A1/es unknown
- 2011-03-17 EC EC2011010901A patent/ECSP11010901A/es unknown
- 2011-03-18 MA MA33710A patent/MA32642B1/fr unknown
- 2011-03-25 CO CO11036952A patent/CO6351734A2/es not_active Application Discontinuation
- 2011-04-11 ZA ZA2011/02690A patent/ZA201102690B/en unknown
-
2012
- 2012-06-18 US US13/525,893 patent/US20120316150A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EA201100368A1 (ru) | 2011-12-30 |
| US20100249091A1 (en) | 2010-09-30 |
| CL2011000570A1 (es) | 2011-06-17 |
| PE20110793A1 (es) | 2011-10-31 |
| ZA201102690B (en) | 2011-12-28 |
| AU2009294290A1 (en) | 2010-03-25 |
| US20120316150A1 (en) | 2012-12-13 |
| AP2011005611A0 (en) | 2011-04-30 |
| EP2350017A1 (en) | 2011-08-03 |
| MA32642B1 (fr) | 2011-09-01 |
| CO6351734A2 (es) | 2011-12-20 |
| KR20110044304A (ko) | 2011-04-28 |
| AU2009294290B2 (en) | 2012-08-30 |
| IL211479A0 (en) | 2011-05-31 |
| CN102159548A (zh) | 2011-08-17 |
| US8232269B2 (en) | 2012-07-31 |
| DOP2011000083A (es) | 2011-03-31 |
| BRPI0918935A2 (pt) | 2015-12-01 |
| JP2012502975A (ja) | 2012-02-02 |
| ECSP11010901A (es) | 2011-04-29 |
| WO2010032200A1 (en) | 2010-03-25 |
| CA2735931A1 (en) | 2010-03-25 |
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Legal Events
| Date | Code | Title | Description |
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| FA | Abandonment or withdrawal |