RU2451674C2 - Пиридинкарбоксамиды в качестве ингибиторов 11-бета-hsd1 - Google Patents
Пиридинкарбоксамиды в качестве ингибиторов 11-бета-hsd1 Download PDFInfo
- Publication number
- RU2451674C2 RU2451674C2 RU2009115830/04A RU2009115830A RU2451674C2 RU 2451674 C2 RU2451674 C2 RU 2451674C2 RU 2009115830/04 A RU2009115830/04 A RU 2009115830/04A RU 2009115830 A RU2009115830 A RU 2009115830A RU 2451674 C2 RU2451674 C2 RU 2451674C2
- Authority
- RU
- Russia
- Prior art keywords
- pyridin
- acetic acid
- propylsulfanyl
- piperidyl
- cyclohexylcarbamoyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 239000003814 drug Substances 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract 4
- 238000001727 in vivo Methods 0.000 claims abstract 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract 4
- 241001465754 Metazoa Species 0.000 claims abstract 3
- FLIPCDXQSSQHMS-SCUMNGBJSA-N 2-[(3s)-1-[5-(1-adamantylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C1=CC=C(C(=O)NC23CC4CC(CC(C4)C2)C3)C=N1 FLIPCDXQSSQHMS-SCUMNGBJSA-N 0.000 claims abstract 2
- ZRWLIWLEJVTMNH-KRWDZBQOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-piperazin-1-ylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCNCC2)=CC=C1C(=O)NC1CCCCC1 ZRWLIWLEJVTMNH-KRWDZBQOSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 81
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 47
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 11
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- -1 cyclohexylcarbamoyl Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000010412 Glaucoma Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000005592 polycycloalkyl group Polymers 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 201000008827 tuberculosis Diseases 0.000 claims 3
- OTVUUOKTGJTVOI-NXEDIBJZSA-N (3r,5s)-4-[[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]amino]adamantane-1-carboxylic acid Chemical compound C1([C@]2([H])CC3C[C@]1(CC(C3)(C2)C(O)=O)[H])NC(N=C1SCCC)=CC=C1C(=O)NC1CCCCC1 OTVUUOKTGJTVOI-NXEDIBJZSA-N 0.000 claims 2
- MFLSCKDFADLNLG-FQEVSTJZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(3,4-dihydro-1h-isoquinolin-2-yl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CC3=CC=CC=C3CC2)=CC=C1C(=O)NC1CCCCC1 MFLSCKDFADLNLG-FQEVSTJZSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- GBOKRRIOJRPDOE-BYICEURKSA-N (1r,5s)-3-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound CCCSC1=NC(N2C[C@@H]3[C@@H](C3C(O)=O)C2)=CC=C1C(=O)NC1CCCCC1 GBOKRRIOJRPDOE-BYICEURKSA-N 0.000 claims 1
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
- WUYAHJJXCBDIKJ-NPWKZODJSA-N (1s,5r)-3-[5-(2-adamantylcarbamoyl)-6-ethylsulfanylpyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound C1C(CC2C3)CC3CC1C2NC(=O)C1=CC=C(N2C[C@@H]3[C@@H](C3C(O)=O)C2)N=C1SCC WUYAHJJXCBDIKJ-NPWKZODJSA-N 0.000 claims 1
- UQXYTOYECTZNET-ASODICMLSA-N (1s,5r)-3-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound C1C(CC2C3)CC3CC1C2NC(=O)C1=CC=C(N2C[C@@H]3[C@@H](C3C(O)=O)C2)N=C1SCCC UQXYTOYECTZNET-ASODICMLSA-N 0.000 claims 1
- HEAOWUYQOYGPJY-XDIGRCDVSA-N (1s,5r)-3-[6-cyclohexylsulfanyl-5-(3-pyridin-3-ylpyrrolidine-1-carbonyl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound C([C@@H]1C([C@@H]1C1)C(=O)O)N1C(N=C1SC2CCCCC2)=CC=C1C(=O)N(C1)CCC1C1=CC=CN=C1 HEAOWUYQOYGPJY-XDIGRCDVSA-N 0.000 claims 1
- DVRHKBLRYFGQHR-XNQJLTTFSA-N (2s)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidine-2-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CCC[C@H]1C(O)=O DVRHKBLRYFGQHR-XNQJLTTFSA-N 0.000 claims 1
- KKIUUXNWTSIXPO-INIZCTEOSA-N (2s)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidine-2-carboxylic acid Chemical compound CCCSC1=NC(N2[C@@H](CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 KKIUUXNWTSIXPO-INIZCTEOSA-N 0.000 claims 1
- KXRYVJZOORPUHV-BWVQPMQLSA-N (3r)-1-[5-(2-adamantylcarbamoyl)-6-ethylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCC)=NC=1N1CC[C@@H](C(O)=O)C1 KXRYVJZOORPUHV-BWVQPMQLSA-N 0.000 claims 1
- LPURRRBKLBZUPO-WFBUYENLSA-N (3r)-1-[5-(2-adamantylcarbamoyl)-6-methylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SC)=NC=1N1CC[C@@H](C(O)=O)C1 LPURRRBKLBZUPO-WFBUYENLSA-N 0.000 claims 1
- LLTNOCNNDPGMCN-KTRILSHOSA-N (3r)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CC[C@@H](C(O)=O)C1 LLTNOCNNDPGMCN-KTRILSHOSA-N 0.000 claims 1
- KXRYVJZOORPUHV-VEYWMJLUSA-N (3s)-1-[5-(2-adamantylcarbamoyl)-6-ethylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCC)=NC=1N1CC[C@H](C(O)=O)C1 KXRYVJZOORPUHV-VEYWMJLUSA-N 0.000 claims 1
- LLTNOCNNDPGMCN-ZAKJRURMSA-N (3s)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CC[C@H](C(O)=O)C1 LLTNOCNNDPGMCN-ZAKJRURMSA-N 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- NVKADYQHGSKWAU-UHFFFAOYSA-N 1-[1-[5-(cyclohexylcarbamoyl)-6-cyclopentylsulfanylpyridin-2-yl]piperidin-3-yl]cyclopropane-1-carboxylic acid Chemical compound C1CCN(C=2N=C(SC3CCCC3)C(C(=O)NC3CCCCC3)=CC=2)CC1C1(C(=O)O)CC1 NVKADYQHGSKWAU-UHFFFAOYSA-N 0.000 claims 1
- SEPOOLQHIXKDEF-UHFFFAOYSA-N 1-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]cyclobutane-1-carboxylic acid Chemical compound CCCSC1=NC(N2CC(CCC2)C2(CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 SEPOOLQHIXKDEF-UHFFFAOYSA-N 0.000 claims 1
- OBIBTFMGDXQHMI-UHFFFAOYSA-N 1-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]cyclopropane-1-carboxylic acid Chemical compound CCCSC1=NC(N2CC(CCC2)C2(CC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 OBIBTFMGDXQHMI-UHFFFAOYSA-N 0.000 claims 1
- TUQXAEMHWYQEKQ-UHFFFAOYSA-N 1-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-4-yl]cyclobutane-1-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(CC2)C2(CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 TUQXAEMHWYQEKQ-UHFFFAOYSA-N 0.000 claims 1
- XJAXAWKEAXKJJB-UHFFFAOYSA-N 1-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-4-yl]cyclopropane-1-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(CC2)C2(CC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 XJAXAWKEAXKJJB-UHFFFAOYSA-N 0.000 claims 1
- JVJMSDLTRHBRJB-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-3-methylpiperidine-3-carboxylic acid Chemical compound CCCSC1=NC(N2CC(C)(CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 JVJMSDLTRHBRJB-UHFFFAOYSA-N 0.000 claims 1
- NLMGUVBLHWMZKH-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-4-methylpiperidine-4-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(C)(CC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 NLMGUVBLHWMZKH-UHFFFAOYSA-N 0.000 claims 1
- NELACKFJPMHQOT-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]-4-propan-2-ylpiperidine-4-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(CC2)(C(C)C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 NELACKFJPMHQOT-UHFFFAOYSA-N 0.000 claims 1
- OYJYRXPSEFHPIA-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]azepane-4-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 OYJYRXPSEFHPIA-UHFFFAOYSA-N 0.000 claims 1
- OUWJQKDZRGZBGA-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidine-2-carboxylic acid Chemical compound CCCSC1=NC(N2C(CCCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 OUWJQKDZRGZBGA-UHFFFAOYSA-N 0.000 claims 1
- MFQPYWLVPWCPPR-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidine-3-carboxylic acid Chemical compound CCCSC1=NC(N2CC(CCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 MFQPYWLVPWCPPR-UHFFFAOYSA-N 0.000 claims 1
- ZLGMJDQCLXIRIW-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidine-4-carboxylic acid Chemical compound CCCSC1=NC(N2CCC(CC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 ZLGMJDQCLXIRIW-UHFFFAOYSA-N 0.000 claims 1
- IPWNSFXRBGOKPT-UHFFFAOYSA-N 1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidine-3-carboxylic acid Chemical compound CCCSC1=NC(N2CC(CC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 IPWNSFXRBGOKPT-UHFFFAOYSA-N 0.000 claims 1
- QPNWKLCBXZTJCR-HMSUTVNQSA-N 2-[(3r)-1-[5-(2-adamantylcarbamoyl)-6-ethylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCC)=NC=1N1CC[C@H](CC(O)=O)C1 QPNWKLCBXZTJCR-HMSUTVNQSA-N 0.000 claims 1
- SCSGTNXILYPGSQ-XMYZRKPFSA-N 2-[(3r)-1-[5-(2-adamantylcarbamoyl)-6-methylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SC)=NC=1N1CC[C@H](CC(O)=O)C1 SCSGTNXILYPGSQ-XMYZRKPFSA-N 0.000 claims 1
- QOCBHDUDZJJMHL-ABYMYHKNSA-N 2-[(3r)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CC[C@H](CC(O)=O)C1 QOCBHDUDZJJMHL-ABYMYHKNSA-N 0.000 claims 1
- CULOQDXMEBSGMA-OAHLLOKOSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-3-fluoro-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound FC=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1N1CCC[C@H](CC(O)=O)C1 CULOQDXMEBSGMA-OAHLLOKOSA-N 0.000 claims 1
- WIWMHUGRFDJESS-OAQYLSRUSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-(2-phenylethylsulfanyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@@H](CC(=O)O)CCCN1C(N=C1SCCC=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 WIWMHUGRFDJESS-OAQYLSRUSA-N 0.000 claims 1
- CAHHMJMKYHUFDI-GOSISDBHSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-cyclohexylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@@H](CC(=O)O)CCCN1C(N=C1SC2CCCCC2)=CC=C1C(=O)NC1CCCCC1 CAHHMJMKYHUFDI-GOSISDBHSA-N 0.000 claims 1
- UNWKTNSGHKJPJI-QGZVFWFLSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-cyclohexylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C1[C@@H](CC(=O)O)CCN1C(N=C1SC2CCCCC2)=CC=C1C(=O)NC1CCCCC1 UNWKTNSGHKJPJI-QGZVFWFLSA-N 0.000 claims 1
- QQWHNWGBOUKEIN-QGZVFWFLSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-cyclopentylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@@H](CC(=O)O)CCCN1C(N=C1SC2CCCC2)=CC=C1C(=O)NC1CCCCC1 QQWHNWGBOUKEIN-QGZVFWFLSA-N 0.000 claims 1
- IATOFNQDDSCHSO-MRXNPFEDSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-cyclopentylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C1[C@@H](CC(=O)O)CCN1C(N=C1SC2CCCC2)=CC=C1C(=O)NC1CCCCC1 IATOFNQDDSCHSO-MRXNPFEDSA-N 0.000 claims 1
- NCDZABJPWMBMIQ-MRXNPFEDSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 NCDZABJPWMBMIQ-MRXNPFEDSA-N 0.000 claims 1
- UZTXBBWTQKNEIG-OAHLLOKOSA-N 2-[(3r)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@@H](CC(O)=O)CC2)=CC=C1C(=O)NC1CCCCC1 UZTXBBWTQKNEIG-OAHLLOKOSA-N 0.000 claims 1
- GKGNIRTXRGLECN-RNXZQOMOSA-N 2-[(3s)-1-[5-(1-adamantylcarbamoyl)-6-methylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC23CC4CC(CC(C4)C2)C3)C(C)=NC=1N1CCC[C@@H](CC(O)=O)C1 GKGNIRTXRGLECN-RNXZQOMOSA-N 0.000 claims 1
- UHCBVICNHRMFMX-DCFCRPKGSA-N 2-[(3s)-1-[5-(2-adamantylcarbamoyl)-6-butylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(CCCC)=NC=1N1CCC[C@@H](CC(O)=O)C1 UHCBVICNHRMFMX-DCFCRPKGSA-N 0.000 claims 1
- ILXOSLRUYLNORZ-QVISQJLHSA-N 2-[(3s)-1-[5-(2-adamantylcarbamoyl)-6-cyclopropylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1C2CC2)=CC=C1C(=O)NC1C(C2)CC3CC2CC1C3 ILXOSLRUYLNORZ-QVISQJLHSA-N 0.000 claims 1
- DEZDNNQATPOEGF-SXFOCMKRSA-N 2-[(3s)-1-[5-(2-adamantylcarbamoyl)-6-methylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(C)=NC=1N1CCC[C@@H](CC(O)=O)C1 DEZDNNQATPOEGF-SXFOCMKRSA-N 0.000 claims 1
- ZLEMFYCDQXGULQ-QYIZGFRMSA-N 2-[(3s)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CCC[C@@H](CC(O)=O)C1 ZLEMFYCDQXGULQ-QYIZGFRMSA-N 0.000 claims 1
- QOCBHDUDZJJMHL-SXFOCMKRSA-N 2-[(3s)-1-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CC[C@@H](CC(O)=O)C1 QOCBHDUDZJJMHL-SXFOCMKRSA-N 0.000 claims 1
- OQGIUZADBRQLNO-HNNXBMFYSA-N 2-[(3s)-1-[5-(4,4-difluoropiperidine-1-carbonyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N1CCC(F)(F)CC1 OQGIUZADBRQLNO-HNNXBMFYSA-N 0.000 claims 1
- AGRNYJCBLOMLGJ-HNNXBMFYSA-N 2-[(3s)-1-[5-(4-carbamoylpiperidine-1-carbonyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N1CCC(C(N)=O)CC1 AGRNYJCBLOMLGJ-HNNXBMFYSA-N 0.000 claims 1
- CULOQDXMEBSGMA-HNNXBMFYSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-3-fluoro-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound FC=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1N1CCC[C@@H](CC(O)=O)C1 CULOQDXMEBSGMA-HNNXBMFYSA-N 0.000 claims 1
- XICSMEVHYFSCMO-NRFANRHFSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(2-phenylethylamino)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1NCCC=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 XICSMEVHYFSCMO-NRFANRHFSA-N 0.000 claims 1
- WIWMHUGRFDJESS-NRFANRHFSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(2-phenylethylsulfanyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1SCCC=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 WIWMHUGRFDJESS-NRFANRHFSA-N 0.000 claims 1
- ASHYVZLNCRWFBZ-SFHVURJKSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(2-pyrazin-2-ylethylsulfanyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1SCCC=2N=CC=NC=2)=CC=C1C(=O)NC1CCCCC1 ASHYVZLNCRWFBZ-SFHVURJKSA-N 0.000 claims 1
- MPURQDYSCJNZDB-FQEVSTJZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(2-pyridin-3-ylethoxy)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1OCCC=2C=NC=CC=2)=CC=C1C(=O)NC1CCCCC1 MPURQDYSCJNZDB-FQEVSTJZSA-N 0.000 claims 1
- MABNZVPFIQPNQO-FQEVSTJZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(2-pyridin-3-ylethylsulfanyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1SCCC=2C=NC=CC=2)=CC=C1C(=O)NC1CCCCC1 MABNZVPFIQPNQO-FQEVSTJZSA-N 0.000 claims 1
- XBEYVXMISRCNDH-SFHVURJKSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(3-methylbutoxy)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CC(C)CCOC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 XBEYVXMISRCNDH-SFHVURJKSA-N 0.000 claims 1
- YIVHEVFYXYIMQI-IBGZPJMESA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(4-ethylsulfonylpiperazin-1-yl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 YIVHEVFYXYIMQI-IBGZPJMESA-N 0.000 claims 1
- WEGLHTQFGNFPQQ-DEOSSOPVSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(4-phenylmethoxycarbonylpiperazin-1-yl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 WEGLHTQFGNFPQQ-DEOSSOPVSA-N 0.000 claims 1
- NYJBPBKPVXQXIF-QFIPXVFZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(4-phenylpiperazin-1-yl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCN(CC2)C=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 NYJBPBKPVXQXIF-QFIPXVFZSA-N 0.000 claims 1
- QVOSIQNMULYAJW-INIZCTEOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-(propylamino)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCNC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 QVOSIQNMULYAJW-INIZCTEOSA-N 0.000 claims 1
- QTRDDHCAPJLKNF-FQEVSTJZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-[2-(4-fluorophenyl)ethoxy]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1OCCC=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CCCCC1 QTRDDHCAPJLKNF-FQEVSTJZSA-N 0.000 claims 1
- DZGMKYVVQNPSKS-AIBWNMTMSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-[3-(4-fluorophenyl)pyrrolidin-1-yl]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CC(CC2)C=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CCCCC1 DZGMKYVVQNPSKS-AIBWNMTMSA-N 0.000 claims 1
- COVVXBQQRFUZQA-NRFANRHFSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-[4-(4-fluorobenzoyl)piperazin-1-yl]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CCCCC1 COVVXBQQRFUZQA-NRFANRHFSA-N 0.000 claims 1
- GJSCCAPNPKHPKQ-QFIPXVFZSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-[methyl(2-phenylethyl)amino]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound N=1C(N2C[C@H](CC(O)=O)CCC2)=CC=C(C(=O)NC2CCCCC2)C=1N(C)CCC1=CC=CC=C1 GJSCCAPNPKHPKQ-QFIPXVFZSA-N 0.000 claims 1
- DBVAIWWZAHIRPF-KRWDZBQOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-[methyl(propyl)amino]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCN(C)C1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 DBVAIWWZAHIRPF-KRWDZBQOSA-N 0.000 claims 1
- QQWHNWGBOUKEIN-KRWDZBQOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-cyclopentylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1SC2CCCC2)=CC=C1C(=O)NC1CCCCC1 QQWHNWGBOUKEIN-KRWDZBQOSA-N 0.000 claims 1
- IATOFNQDDSCHSO-INIZCTEOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-cyclopentylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCN1C(N=C1SC2CCCC2)=CC=C1C(=O)NC1CCCCC1 IATOFNQDDSCHSO-INIZCTEOSA-N 0.000 claims 1
- UVLKNKMJZSBROZ-HNNXBMFYSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-cyclopropylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1C2CC2)=CC=C1C(=O)NC1CCCCC1 UVLKNKMJZSBROZ-HNNXBMFYSA-N 0.000 claims 1
- ISUBFMQRGSCEHL-AWEZNQCLSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-methoxypyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound COC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 ISUBFMQRGSCEHL-AWEZNQCLSA-N 0.000 claims 1
- ADFKQQACZXAVRN-HNNXBMFYSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-methylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 ADFKQQACZXAVRN-HNNXBMFYSA-N 0.000 claims 1
- ZAYVFUVDFQCDFH-KRWDZBQOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-morpholin-4-ylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCOCC2)=CC=C1C(=O)NC1CCCCC1 ZAYVFUVDFQCDFH-KRWDZBQOSA-N 0.000 claims 1
- KBMYMEBMUZWXNB-SFHVURJKSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-piperidin-1-ylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCCCC2)=CC=C1C(=O)NC1CCCCC1 KBMYMEBMUZWXNB-SFHVURJKSA-N 0.000 claims 1
- GJJUVRHRHOIJDZ-INIZCTEOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-propoxypyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCOC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 GJJUVRHRHOIJDZ-INIZCTEOSA-N 0.000 claims 1
- NCDZABJPWMBMIQ-INIZCTEOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 NCDZABJPWMBMIQ-INIZCTEOSA-N 0.000 claims 1
- UZTXBBWTQKNEIG-HNNXBMFYSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]pyrrolidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CC2)=CC=C1C(=O)NC1CCCCC1 UZTXBBWTQKNEIG-HNNXBMFYSA-N 0.000 claims 1
- ZKHWPWLULNPFAF-KRWDZBQOSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)-6-pyrrolidin-1-ylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCCC2)=CC=C1C(=O)NC1CCCCC1 ZKHWPWLULNPFAF-KRWDZBQOSA-N 0.000 claims 1
- BDTJNEMNIPKUIF-AWEZNQCLSA-N 2-[(3s)-1-[5-(cyclohexylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C1=CC=C(C(=O)NC2CCCCC2)C=N1 BDTJNEMNIPKUIF-AWEZNQCLSA-N 0.000 claims 1
- RYUCFSARRJJSQU-HNNXBMFYSA-N 2-[(3s)-1-[5-(oxan-4-ylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCOCC1 RYUCFSARRJJSQU-HNNXBMFYSA-N 0.000 claims 1
- NJMKZNRIZPAUCN-INIZCTEOSA-N 2-[(3s)-1-[5-(piperidine-1-carbonyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N1CCCCC1 NJMKZNRIZPAUCN-INIZCTEOSA-N 0.000 claims 1
- AMSUENPUCKPGGN-GTPINHCMSA-N 2-[(3s)-1-[5-[(4-hydroxycyclohexyl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCC(O)CC1 AMSUENPUCKPGGN-GTPINHCMSA-N 0.000 claims 1
- QYVSMIVRWCSXAZ-SFHVURJKSA-N 2-[(3s)-1-[5-[cyclohexyl(cyclopropyl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1CCCCC1)C1CC1 QYVSMIVRWCSXAZ-SFHVURJKSA-N 0.000 claims 1
- ZMLDBFQNSHTHBA-FQEVSTJZSA-N 2-[(3s)-1-[5-[cyclohexyl(cyclopropylmethyl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1CCCCC1)CC1CC1 ZMLDBFQNSHTHBA-FQEVSTJZSA-N 0.000 claims 1
- AROMIVMFUAPFKU-SFHVURJKSA-N 2-[(3s)-1-[5-[cyclohexyl(ethyl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(CC)C1CCCCC1 AROMIVMFUAPFKU-SFHVURJKSA-N 0.000 claims 1
- ZNUWJDYQPCHRQG-KRWDZBQOSA-N 2-[(3s)-1-[5-[cyclohexyl(methyl)carbamoyl]-6-(propylamino)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCNC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C)C1CCCCC1 ZNUWJDYQPCHRQG-KRWDZBQOSA-N 0.000 claims 1
- ZSRZVONCSYFTSU-SFHVURJKSA-N 2-[(3s)-1-[5-[cyclohexyl(methyl)carbamoyl]-6-[methyl(propyl)amino]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCN(C)C1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C)C1CCCCC1 ZSRZVONCSYFTSU-SFHVURJKSA-N 0.000 claims 1
- SAYFMVBIFLYMRS-KRWDZBQOSA-N 2-[(3s)-1-[5-[cyclohexyl(methyl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C)C1CCCCC1 SAYFMVBIFLYMRS-KRWDZBQOSA-N 0.000 claims 1
- JTULUHITEXTPHD-IBGZPJMESA-N 2-[(3s)-1-[5-[cyclohexyl(propan-2-yl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C(C)C)C1CCCCC1 JTULUHITEXTPHD-IBGZPJMESA-N 0.000 claims 1
- SIRPPHOMDWANGK-INIZCTEOSA-N 2-[(3s)-1-[5-[methyl(oxan-4-yl)carbamoyl]-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C)C1CCOCC1 SIRPPHOMDWANGK-INIZCTEOSA-N 0.000 claims 1
- NEATYAVACQARGG-IBGZPJMESA-N 2-[(3s)-1-[6-(4-acetylpiperazin-1-yl)-5-(cyclohexylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1CN(C(=O)C)CCN1C1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 NEATYAVACQARGG-IBGZPJMESA-N 0.000 claims 1
- UMIQWAMCDLPJGV-FQEVSTJZSA-N 2-[(3s)-1-[6-[2-(4-chlorophenyl)ethylamino]-5-(cyclohexylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1NCCC=2C=CC(Cl)=CC=2)=CC=C1C(=O)NC1CCCCC1 UMIQWAMCDLPJGV-FQEVSTJZSA-N 0.000 claims 1
- KVTZEZSPIHYJTE-QFIPXVFZSA-N 2-[(3s)-1-[6-[4-(benzenesulfonyl)piperazin-1-yl]-5-(cyclohexylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1N2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=CC=C1C(=O)NC1CCCCC1 KVTZEZSPIHYJTE-QFIPXVFZSA-N 0.000 claims 1
- GTKTXVLDMNTDMQ-KRWDZBQOSA-N 2-[(3s)-1-[6-butyl-5-(cyclohexylcarbamoyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCCC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 GTKTXVLDMNTDMQ-KRWDZBQOSA-N 0.000 claims 1
- XROHBHIHWGAZJM-ZQRQZVKFSA-N 2-[(3s)-1-[6-cyclopentylsulfanyl-5-(3-pyridin-3-ylpyrrolidine-1-carbonyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound C1[C@H](CC(=O)O)CCCN1C(N=C1SC2CCCC2)=CC=C1C(=O)N1CC(C=2C=NC=CC=2)CC1 XROHBHIHWGAZJM-ZQRQZVKFSA-N 0.000 claims 1
- KSFBJDKGSCPVAM-ZENAZSQFSA-N 2-[(3s)-1-[6-propylsulfanyl-5-(3-pyrazin-2-ylpyrrolidine-1-carbonyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1)CCC1C1=CN=CC=N1 KSFBJDKGSCPVAM-ZENAZSQFSA-N 0.000 claims 1
- AHLSUADPLSQCSA-OYKVQYDMSA-N 2-[(3s)-1-[6-propylsulfanyl-5-(3-pyridin-2-ylpyrrolidine-1-carbonyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1)CCC1C1=CC=CC=N1 AHLSUADPLSQCSA-OYKVQYDMSA-N 0.000 claims 1
- FOEJBQIYVOHFSX-LROBGIAVSA-N 2-[(3s)-1-[6-propylsulfanyl-5-(3-pyridin-3-ylpyrrolidine-1-carbonyl)pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1)CCC1C1=CC=CN=C1 FOEJBQIYVOHFSX-LROBGIAVSA-N 0.000 claims 1
- SNJPVMVDQAXZMA-VYRBHSGPSA-N 2-[(3s)-1-[6-propylsulfanyl-5-[3-(trifluoromethyl)piperidine-1-carbonyl]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N1CCCC(C(F)(F)F)C1 SNJPVMVDQAXZMA-VYRBHSGPSA-N 0.000 claims 1
- WLBGMTJZNWHPLM-OYKVQYDMSA-N 2-[(3s)-1-[6-propylsulfanyl-5-[3-[2-(trifluoromethyl)phenyl]pyrrolidine-1-carbonyl]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N(C1)CCC1C1=CC=CC=C1C(F)(F)F WLBGMTJZNWHPLM-OYKVQYDMSA-N 0.000 claims 1
- ZEZQAIPFKAGRCU-HNNXBMFYSA-N 2-[(3s)-1-[6-propylsulfanyl-5-[4-(trifluoromethyl)piperidine-1-carbonyl]pyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2C[C@H](CC(O)=O)CCC2)=CC=C1C(=O)N1CCC(C(F)(F)F)CC1 ZEZQAIPFKAGRCU-HNNXBMFYSA-N 0.000 claims 1
- GTUDBQDYDZTOGI-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]-2-methylpropanoic acid Chemical compound CCCSC1=NC(N2CC(CCC2)C(C)(C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 GTUDBQDYDZTOGI-UHFFFAOYSA-N 0.000 claims 1
- NCDZABJPWMBMIQ-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]acetic acid Chemical compound CCCSC1=NC(N2CC(CC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 NCDZABJPWMBMIQ-UHFFFAOYSA-N 0.000 claims 1
- VNNOSPFMDVVKMD-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]oxy-2-methylpropanoic acid Chemical compound CCCSC1=NC(N2CC(CCC2)OC(C)(C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 VNNOSPFMDVVKMD-UHFFFAOYSA-N 0.000 claims 1
- JRYCXASJIJYAGH-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]oxyacetic acid Chemical compound CCCSC1=NC(N2CC(CCC2)OCC(O)=O)=CC=C1C(=O)NC1CCCCC1 JRYCXASJIJYAGH-UHFFFAOYSA-N 0.000 claims 1
- SDBPYWSWQDSKDL-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]oxypropanoic acid Chemical compound CCCSC1=NC(N2CC(CCC2)OC(C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 SDBPYWSWQDSKDL-UHFFFAOYSA-N 0.000 claims 1
- NUNLJZNHEAEMFR-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound CCCSC1=NC(N2CCC(CC2)C(C)(C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 NUNLJZNHEAEMFR-UHFFFAOYSA-N 0.000 claims 1
- MCCSIDXTNHFYKE-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound CCCSC1=NC(N2CCC(CC(O)=O)CC2)=CC=C1C(=O)NC1CCCCC1 MCCSIDXTNHFYKE-UHFFFAOYSA-N 0.000 claims 1
- AMGRCXKRLIHRCS-UHFFFAOYSA-N 2-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-4-yl]propanoic acid Chemical compound CCCSC1=NC(N2CCC(CC2)C(C)C(O)=O)=CC=C1C(=O)NC1CCCCC1 AMGRCXKRLIHRCS-UHFFFAOYSA-N 0.000 claims 1
- DSKZCZYYGSJDHV-UHFFFAOYSA-N 2-[3-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]oxyphenyl]acetic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1OC1=CC=CC(CC(O)=O)=C1 DSKZCZYYGSJDHV-UHFFFAOYSA-N 0.000 claims 1
- ANODRYWADGDDLM-UHFFFAOYSA-N 2-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]oxyphenoxy]acetic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1OC1=CC=C(OCC(O)=O)C=C1 ANODRYWADGDDLM-UHFFFAOYSA-N 0.000 claims 1
- HJRLXHFWMKEEIN-UHFFFAOYSA-N 2-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]oxyphenyl]propanoic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1OC1=CC=C(C(C)C(O)=O)C=C1 HJRLXHFWMKEEIN-UHFFFAOYSA-N 0.000 claims 1
- LDPRXTKVDRGIMT-UHFFFAOYSA-N 2-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperazin-1-yl]acetic acid Chemical compound CCCSC1=NC(N2CCN(CC(O)=O)CC2)=CC=C1C(=O)NC1CCCCC1 LDPRXTKVDRGIMT-UHFFFAOYSA-N 0.000 claims 1
- HUEDKGNPZYCQSB-UHFFFAOYSA-N 2-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]sulfanylphenoxy]acetic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1SC1=CC=C(OCC(O)=O)C=C1 HUEDKGNPZYCQSB-UHFFFAOYSA-N 0.000 claims 1
- ZGRBKIYHILNWNJ-UHFFFAOYSA-N 2-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]sulfanylphenyl]acetic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1SC1=CC=C(CC(O)=O)C=C1 ZGRBKIYHILNWNJ-UHFFFAOYSA-N 0.000 claims 1
- OJBFWJPKKNTZBA-UHFFFAOYSA-N 2-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]sulfanylbenzoic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1SC1=CC=CC=C1C(O)=O OJBFWJPKKNTZBA-UHFFFAOYSA-N 0.000 claims 1
- JEZQQEUCVUKRAC-UHFFFAOYSA-N 3-[1-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]piperidin-3-yl]propanoic acid Chemical compound CCCSC1=NC(N2CC(CCC(O)=O)CCC2)=CC=C1C(=O)NC1CCCCC1 JEZQQEUCVUKRAC-UHFFFAOYSA-N 0.000 claims 1
- NOQVXLJWLRHUOL-UHFFFAOYSA-N 3-[4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]oxyphenyl]propanoic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1OC1=CC=C(CCC(O)=O)C=C1 NOQVXLJWLRHUOL-UHFFFAOYSA-N 0.000 claims 1
- XJCZMQZSBNAEND-UHFFFAOYSA-N 3-[5-(2-adamantylcarbamoyl)-6-butylpyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Chemical compound C1C(CC2C3)CC3CC1C2NC(=O)C1=CC=C(N2CC3C(C3C(O)=O)C2)N=C1CCCC XJCZMQZSBNAEND-UHFFFAOYSA-N 0.000 claims 1
- SWEVLFSXNGUATR-UHFFFAOYSA-N 3-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]sulfanylbenzoic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1SC1=CC=CC(C(O)=O)=C1 SWEVLFSXNGUATR-UHFFFAOYSA-N 0.000 claims 1
- TWSMMGCFKFUITI-UHFFFAOYSA-N 3-[[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]amino]propanoic acid Chemical compound CCCSC1=NC(NCCC(O)=O)=CC=C1C(=O)NC1CCCCC1 TWSMMGCFKFUITI-UHFFFAOYSA-N 0.000 claims 1
- 125000005977 3-phenylpropyloxy group Chemical group 0.000 claims 1
- UTTJDSDFBCWGMB-UHFFFAOYSA-N 4-[5-(2-adamantylcarbamoyl)-6-propylsulfanylpyridin-2-yl]morpholine-2-carboxylic acid Chemical compound C=1C=C(C(=O)NC2C3CC4CC(C3)CC2C4)C(SCCC)=NC=1N1CCOC(C(O)=O)C1 UTTJDSDFBCWGMB-UHFFFAOYSA-N 0.000 claims 1
- UKLYDDLGLXXVCF-UHFFFAOYSA-N 4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]morpholine-2-carboxylic acid Chemical compound CCCSC1=NC(N2CC(OCC2)C(O)=O)=CC=C1C(=O)NC1CCCCC1 UKLYDDLGLXXVCF-UHFFFAOYSA-N 0.000 claims 1
- COPDWTHUTCKCJS-UHFFFAOYSA-N 4-[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]sulfanylbenzoic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1SC1=CC=C(C(O)=O)C=C1 COPDWTHUTCKCJS-UHFFFAOYSA-N 0.000 claims 1
- LSNUPHZZOYTURX-UHFFFAOYSA-N 4-[[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]amino]cyclohexane-1-carboxylic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1NC1CCC(C(O)=O)CC1 LSNUPHZZOYTURX-UHFFFAOYSA-N 0.000 claims 1
- LNJRBNUEVZIFCD-UHFFFAOYSA-N 4-[[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]methylamino]cyclohexane-1-carboxylic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1CNC1CCC(C(O)=O)CC1 LNJRBNUEVZIFCD-UHFFFAOYSA-N 0.000 claims 1
- DXCCQDZRHQWJET-UHFFFAOYSA-N 4-[[[5-(cyclohexylcarbamoyl)-6-propylsulfanylpyridin-2-yl]amino]methyl]cyclohexane-1-carboxylic acid Chemical compound C=1C=C(C(=O)NC2CCCCC2)C(SCCC)=NC=1NCC1CCC(C(O)=O)CC1 DXCCQDZRHQWJET-UHFFFAOYSA-N 0.000 claims 1
- GQRZVTQRTAZATQ-UUEODZFSSA-N C1CCC(C1)SC2=C(C=CC(=N2)N3CC[C@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 Chemical compound C1CCC(C1)SC2=C(C=CC(=N2)N3CC[C@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 GQRZVTQRTAZATQ-UUEODZFSSA-N 0.000 claims 1
- NQDOPABZRGZDNJ-JRBCGFFPSA-N C1CCC(CC1)SC2=C(C=CC(=N2)N3CC[C@@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 Chemical compound C1CCC(CC1)SC2=C(C=CC(=N2)N3CC[C@@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 NQDOPABZRGZDNJ-JRBCGFFPSA-N 0.000 claims 1
- NQDOPABZRGZDNJ-KQWBDTQASA-N C1CCC(CC1)SC2=C(C=CC(=N2)N3CC[C@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 Chemical compound C1CCC(CC1)SC2=C(C=CC(=N2)N3CC[C@H](C3)C(C(=O)O)O)C(=O)NC4C5CC6CC(C5)CC4C6 NQDOPABZRGZDNJ-KQWBDTQASA-N 0.000 claims 1
- WDRKLYMQYOKYDB-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)C2=C(C(=CC=C2)C(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)C2=C(C(=CC=C2)C(=O)O)O)C(=O)NC3CCCCC3 WDRKLYMQYOKYDB-UHFFFAOYSA-N 0.000 claims 1
- WLIVHNMYIREIPT-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)C2=CC(=C(C=C2)C(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)C2=CC(=C(C=C2)C(=O)O)O)C(=O)NC3CCCCC3 WLIVHNMYIREIPT-UHFFFAOYSA-N 0.000 claims 1
- LVXAAIROLVVYKM-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)C2=CC(=C(C=C2)CC(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)C2=CC(=C(C=C2)CC(=O)O)O)C(=O)NC3CCCCC3 LVXAAIROLVVYKM-UHFFFAOYSA-N 0.000 claims 1
- JQSHRSCCMPQABP-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)C2CCC(CC2)(C(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)C2CCC(CC2)(C(=O)O)O)C(=O)NC3CCCCC3 JQSHRSCCMPQABP-UHFFFAOYSA-N 0.000 claims 1
- UBCBOSRZZSOCSX-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)N2CC(C2)C(C(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)N2CC(C2)C(C(=O)O)O)C(=O)NC3CCCCC3 UBCBOSRZZSOCSX-UHFFFAOYSA-N 0.000 claims 1
- JXZMWBAYWWSNAN-UHFFFAOYSA-N CCCSC1=C(C=CC(=N1)N2CCC(C2)C(C(=O)O)O)C(=O)NC3CCCCC3 Chemical compound CCCSC1=C(C=CC(=N1)N2CCC(C2)C(C(=O)O)O)C(=O)NC3CCCCC3 JXZMWBAYWWSNAN-UHFFFAOYSA-N 0.000 claims 1
- JGYUCOWXSLYLDG-KTBMJJBCSA-N CCCSC1=C(C=CC(=N1)N2CC[C@@H](C2)C(C(=O)O)O)C(=O)NC3C4CC5CC(C4)CC3C5 Chemical compound CCCSC1=C(C=CC(=N1)N2CC[C@@H](C2)C(C(=O)O)O)C(=O)NC3C4CC5CC(C4)CC3C5 JGYUCOWXSLYLDG-KTBMJJBCSA-N 0.000 claims 1
- JGYUCOWXSLYLDG-JIJFESOXSA-N CCCSC1=C(C=CC(=N1)N2CC[C@H](C2)C(C(=O)O)O)C(=O)NC3C4CC5CC(C4)CC3C5 Chemical compound CCCSC1=C(C=CC(=N1)N2CC[C@H](C2)C(C(=O)O)O)C(=O)NC3C4CC5CC(C4)CC3C5 JGYUCOWXSLYLDG-JIJFESOXSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 229960004275 glycolic acid Drugs 0.000 claims 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 230000000694 effects Effects 0.000 abstract 3
- 230000005764 inhibitory process Effects 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 *N(*)C(C(C(O*)=NC(**C(O)=O)=C1)=C*1P)=O Chemical compound *N(*)C(C(C(O*)=NC(**C(O)=O)=C1)=C*1P)=O 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Obesity (AREA)
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- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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| US86424706P | 2006-11-03 | 2006-11-03 | |
| US86430306P | 2006-11-03 | 2006-11-03 | |
| US60/864,247 | 2006-11-03 | ||
| US60/864,303 | 2006-11-03 |
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| RU2009115830A RU2009115830A (ru) | 2010-12-10 |
| RU2451674C2 true RU2451674C2 (ru) | 2012-05-27 |
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| MX (1) | MX2009004707A (enExample) |
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