JP2008515962A5 - - Google Patents
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- Publication number
- JP2008515962A5 JP2008515962A5 JP2007536276A JP2007536276A JP2008515962A5 JP 2008515962 A5 JP2008515962 A5 JP 2008515962A5 JP 2007536276 A JP2007536276 A JP 2007536276A JP 2007536276 A JP2007536276 A JP 2007536276A JP 2008515962 A5 JP2008515962 A5 JP 2008515962A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- ylmethyl
- acetyl
- boc
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 42
- -1 nitro, hydroxy Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims 3
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 3
- QGNOGAFKDGNVQA-FQUUOJAGSA-N (2s,4s)-1-[2-[[(1r,3r)-3-(2-cyanoethyl)cyclopentyl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile Chemical compound C1[C@@H](F)C[C@@H](C#N)N1C(=O)CN[C@H]1C[C@@H](CCC#N)CC1 QGNOGAFKDGNVQA-FQUUOJAGSA-N 0.000 claims 2
- YMXGFRQHFHFPOW-XQHKEYJVSA-N (2s,4s)-1-[2-[[(1r,3s)-3-(cyanomethyl)cyclopentyl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile Chemical compound C1[C@@H](F)C[C@@H](C#N)N1C(=O)CN[C@H]1C[C@@H](CC#N)CC1 YMXGFRQHFHFPOW-XQHKEYJVSA-N 0.000 claims 2
- YMXGFRQHFHFPOW-CYDGBPFRSA-N (2s,4s)-1-[2-[[(1s,3r)-3-(cyanomethyl)cyclopentyl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile Chemical compound C1[C@@H](F)C[C@@H](C#N)N1C(=O)CN[C@@H]1C[C@H](CC#N)CC1 YMXGFRQHFHFPOW-CYDGBPFRSA-N 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Natural products CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001753 carvones Chemical class 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- JSXSIVQMYRIDBD-SBKWZQTDSA-N (1R,3S)-3-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)cyclopentan-1-amine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1N(CCC2=CC=CC=C12)C[C@@H]1C[C@@H](CC1)N JSXSIVQMYRIDBD-SBKWZQTDSA-N 0.000 claims 1
- FISJYXZOMFAWTH-SCLLHFNJSA-N (1r,3r)-3-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@H]1CN1N=CN=C1 FISJYXZOMFAWTH-SCLLHFNJSA-N 0.000 claims 1
- ZMBNLBSFOOZHKQ-MHDYBILJSA-N (1r,3r)-3-[(2-methoxyphenyl)methyl]cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC=C1C[C@@H]1C[C@H](N)CC1 ZMBNLBSFOOZHKQ-MHDYBILJSA-N 0.000 claims 1
- XYBQISJWMAKZSH-VXGBXAGGSA-N (1r,3r)-3-benzylcyclopentan-1-amine Chemical compound C1[C@H](N)CC[C@@H]1CC1=CC=CC=C1 XYBQISJWMAKZSH-VXGBXAGGSA-N 0.000 claims 1
- FISJYXZOMFAWTH-KZYPOYLOSA-N (1r,3s)-3-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1N=CN=C1 FISJYXZOMFAWTH-KZYPOYLOSA-N 0.000 claims 1
- ATXGSMDSURIOLC-YECZQDJWSA-N (1r,3s)-3-(1,3-dihydroisoindol-2-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1CC2=CC=CC=C2C1 ATXGSMDSURIOLC-YECZQDJWSA-N 0.000 claims 1
- YHGHGAYGONPKEX-BAUSSPIASA-N (1r,3s)-3-(2,3-dihydrobenzotriazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1C2=CC=CC=C2NN1 YHGHGAYGONPKEX-BAUSSPIASA-N 0.000 claims 1
- RFTDZQBDJJRODQ-STEACBGWSA-N (1r,3s)-3-(2,3-dihydroindol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1C2=CC=CC=C2CC1 RFTDZQBDJJRODQ-STEACBGWSA-N 0.000 claims 1
- LZHZTLXNTKYUOH-VHSXEESVSA-N (1r,3s)-3-(benzotriazol-2-ylmethyl)cyclopentan-1-amine Chemical compound C1[C@H](N)CC[C@@H]1CN1N=C2C=CC=CC2=N1 LZHZTLXNTKYUOH-VHSXEESVSA-N 0.000 claims 1
- HRRLDCXWMGNJIP-BAUSSPIASA-N (1r,3s)-3-(benzotriazol-2-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1N=C2C=CC=CC2=N1 HRRLDCXWMGNJIP-BAUSSPIASA-N 0.000 claims 1
- PGFKSJGKEMYPAV-OULXEKPRSA-N (1r,3s)-3-(imidazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1C=NC=C1 PGFKSJGKEMYPAV-OULXEKPRSA-N 0.000 claims 1
- RDIMQQQRELYIMA-BAUSSPIASA-N (1r,3s)-3-(morpholin-4-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1CCOCC1 RDIMQQQRELYIMA-BAUSSPIASA-N 0.000 claims 1
- FUVZLVBWGATPDZ-OULXEKPRSA-N (1r,3s)-3-[(1,1-dioxo-1,2-thiazolidin-2-yl)methyl]cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@H](N)CC[C@@H]1CN1S(=O)(=O)CCC1 FUVZLVBWGATPDZ-OULXEKPRSA-N 0.000 claims 1
- GHPBFIPVTAHUFH-ZVWHLABXSA-N (1r,3s)-3-[(2,5-dimethylpyrrol-1-yl)methyl]cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=C(C)N1C[C@@H]1C[C@H](N)CC1 GHPBFIPVTAHUFH-ZVWHLABXSA-N 0.000 claims 1
- FISJYXZOMFAWTH-WLYNEOFISA-N (1s,3r)-3-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1N=CN=C1 FISJYXZOMFAWTH-WLYNEOFISA-N 0.000 claims 1
- HARICIXQCOMWDS-IYJPBCIQSA-N (1s,3r)-3-(indazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1C2=CC=CC=C2C=N1 HARICIXQCOMWDS-IYJPBCIQSA-N 0.000 claims 1
- SOGGGKAUCJMOPN-IYJPBCIQSA-N (1s,3r)-3-(indazol-2-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1N=C2C=CC=CC2=C1 SOGGGKAUCJMOPN-IYJPBCIQSA-N 0.000 claims 1
- YMXLUFVZWKQJKJ-RJUBDTSPSA-N (1s,3r)-3-(pyrazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1N=CC=C1 YMXLUFVZWKQJKJ-RJUBDTSPSA-N 0.000 claims 1
- GTEVGUPANVPJRC-WLYNEOFISA-N (1s,3r)-3-(triazol-1-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1N=NC=C1 GTEVGUPANVPJRC-WLYNEOFISA-N 0.000 claims 1
- VROJAWMOYZWSNX-WLYNEOFISA-N (1s,3r)-3-(triazol-2-ylmethyl)cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1N=CC=N1 VROJAWMOYZWSNX-WLYNEOFISA-N 0.000 claims 1
- CRCFMMTVWUXGKH-LIOBNPLQSA-N (1s,3r)-3-[(4-phenylpiperazin-1-yl)methyl]cyclopentan-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1[C@@H](N)CC[C@H]1CN1CCN(C=2C=CC=CC=2)CC1 CRCFMMTVWUXGKH-LIOBNPLQSA-N 0.000 claims 1
- MUMSEHFWBGQGNG-KZYPOYLOSA-N (1s,4r)-4-(1,2,4-triazol-1-ylmethyl)cyclopent-2-en-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C[C@@H](N)C[C@H]1CN1N=CN=C1 MUMSEHFWBGQGNG-KZYPOYLOSA-N 0.000 claims 1
- JJCWCECVSFPLRC-IMUQEULPSA-N (2s)-1-(3-aminocyclopentanecarbonyl)pyrrolidine-2-carbonitrile;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1C(N)CCC1C(=O)N1[C@H](C#N)CCC1 JJCWCECVSFPLRC-IMUQEULPSA-N 0.000 claims 1
- OPBAUWWPQFSAOI-MCIGGMRASA-N (2s)-1-[2-[(3-cyanocyclopentyl)amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNC1CCC(C#N)C1 OPBAUWWPQFSAOI-MCIGGMRASA-N 0.000 claims 1
- NZHRKBKTKWQHRW-MJBXVCDLSA-N (2s)-1-[2-[[(1r,3s)-3-(1,2,4-triazol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C([C@H]1CC[C@H](C1)NCC(=O)N1[C@@H](CCC1)C#N)N1C=NC=N1 NZHRKBKTKWQHRW-MJBXVCDLSA-N 0.000 claims 1
- PPGDORKIIFXPNU-DBVUQKKJSA-N (2s)-1-[2-[[(1r,3s)-3-(1,3-dihydroisoindol-2-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N([C@H]1C[C@@H](CN2CC3=CC=CC=C3C2)CC1)CC(=O)N1CCC[C@H]1C#N PPGDORKIIFXPNU-DBVUQKKJSA-N 0.000 claims 1
- NWOQBZHQGOHVFO-XHSDSOJGSA-N (2s)-1-[2-[[(1r,3s)-3-(2,3-dihydrobenzotriazol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N([C@H]1C[C@@H](CN2C3=CC=CC=C3NN2)CC1)CC(=O)N1CCC[C@H]1C#N NWOQBZHQGOHVFO-XHSDSOJGSA-N 0.000 claims 1
- MVTWTTDMTPSOJY-UHOSZYNNSA-N (2s)-1-[2-[[(1r,3s)-3-(2,3-dihydroindol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N([C@H]1C[C@@H](CN2C3=CC=CC=C3CC2)CC1)CC(=O)N1CCC[C@H]1C#N MVTWTTDMTPSOJY-UHOSZYNNSA-N 0.000 claims 1
- MTNUXJUPIJQLHH-BBWFWOEESA-N (2s)-1-[2-[[(1r,3s)-3-(benzimidazol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N([C@H]1C[C@@H](CN2C3=CC=CC=C3N=C2)CC1)CC(=O)N1CCC[C@H]1C#N MTNUXJUPIJQLHH-BBWFWOEESA-N 0.000 claims 1
- VMYUSJJAIOYGFX-XHSDSOJGSA-N (2s)-1-[2-[[(1r,3s)-3-(benzotriazol-2-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N([C@H]1C[C@@H](CN2N=C3C=CC=CC3=N2)CC1)CC(=O)N1CCC[C@H]1C#N VMYUSJJAIOYGFX-XHSDSOJGSA-N 0.000 claims 1
- NGZTVZNWLPPVGQ-UPJWGTAASA-N (2s)-1-[2-[[(1r,3s)-3-(cyanomethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CN[C@@H]1CC[C@H](CC#N)C1 NGZTVZNWLPPVGQ-UPJWGTAASA-N 0.000 claims 1
- WTSADRPXCPMCAW-ZNMIVQPWSA-N (2s)-1-[2-[[(1r,3s)-3-(imidazol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C([C@H]1CC[C@H](C1)NCC(=O)N1[C@@H](CCC1)C#N)N1C=CN=C1 WTSADRPXCPMCAW-ZNMIVQPWSA-N 0.000 claims 1
- KIHLKFPJLZFBGT-XHSDSOJGSA-N (2s)-1-[2-[[(1r,3s)-3-(morpholin-4-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C([C@H]1CC[C@H](C1)NCC(=O)N1[C@@H](CCC1)C#N)N1CCOCC1 KIHLKFPJLZFBGT-XHSDSOJGSA-N 0.000 claims 1
- KLOWNBULXQPQHF-ZNMIVQPWSA-N (2s)-1-[2-[[(1r,3s)-3-[(1,1-dioxo-1,2-thiazolidin-2-yl)methyl]cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C([C@H]1CC[C@H](C1)NCC(=O)N1[C@@H](CCC1)C#N)N1CCCS1(=O)=O KLOWNBULXQPQHF-ZNMIVQPWSA-N 0.000 claims 1
- YMTDMNKORGPJSB-QGTPRVQTSA-N (2s)-1-[2-[[(1r,3s)-3-[[5-(4-fluorophenyl)tetrazol-2-yl]methyl]cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=NN(C[C@@H]2C[C@@H](CC2)NCC(=O)N2[C@@H](CCC2)C#N)N=N1 YMTDMNKORGPJSB-QGTPRVQTSA-N 0.000 claims 1
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- NGZTVZNWLPPVGQ-AVGNSLFASA-N (2s)-1-[2-[[(1s,3r)-3-(cyanomethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CN[C@H]1CC[C@@H](CC#N)C1 NGZTVZNWLPPVGQ-AVGNSLFASA-N 0.000 claims 1
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- 2005-07-26 MX MX2007004305A patent/MX2007004305A/es active IP Right Grant
- 2005-07-26 EA EA200700720A patent/EA013463B1/ru not_active IP Right Cessation
- 2005-07-26 KR KR1020077010262A patent/KR20070073887A/ko not_active Ceased
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- 2005-07-26 JP JP2007536276A patent/JP4959569B2/ja not_active Expired - Fee Related
- 2005-07-26 AU AU2005293266A patent/AU2005293266B2/en not_active Ceased
- 2005-07-26 WO PCT/IB2005/002204 patent/WO2006040625A1/en not_active Ceased
- 2005-09-29 TW TW094134070A patent/TW200614988A/zh unknown
- 2005-10-03 MY MYPI20054654A patent/MY142423A/en unknown
- 2005-10-12 US US11/250,195 patent/US7205323B2/en not_active Expired - Lifetime
- 2005-10-12 AR ARP050104282A patent/AR053415A1/es unknown
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2007
- 2007-02-15 US US11/675,157 patent/US7524844B2/en not_active Expired - Lifetime
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- 2007-04-10 IL IL182444A patent/IL182444A0/en unknown
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