NO325135B1 - Dipeptidforbindelser, mellomprodukter for fremstilling av slike, anvendelse av disse for fremstilling av medikamenter for behandling samt farmasoytiske preparater inneholdende slike - Google Patents

Dipeptidforbindelser, mellomprodukter for fremstilling av slike, anvendelse av disse for fremstilling av medikamenter for behandling samt farmasoytiske preparater inneholdende slike Download PDF

Info

Publication number: NO325135B1
Authority: NO; Norway
Prior art keywords: alkyl; phenyl; optionally substituted; group; methyl
Prior art date: 1995-12-28

Application number

NO19982991A

Other languages

English (en)

Norwegian (no)

Other versions

NO982991D0 (no

NO982991L (no

Inventor

Bruce A Lefker

Paul A Dasilva Jardine

Philip Albert Carpino

John Anthony Ragan

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1995-12-28

Filing date

1998-06-26

Publication date

2008-02-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21737850&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO325135(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-06-26 Application filed by Pfizer filed Critical Pfizer

1998-06-26 Publication of NO982991D0 publication Critical patent/NO982991D0/no

1998-08-26 Publication of NO982991L publication Critical patent/NO982991L/no

2008-02-04 Publication of NO325135B1 publication Critical patent/NO325135B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 365
238000011282 treatment Methods 0.000 title claims abstract description 62
238000002360 preparation method Methods 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title claims abstract description 24
239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 6
239000003814 drug Substances 0.000 title claims description 42
239000000543 intermediate Substances 0.000 title abstract description 21
108010016626 Dipeptides Proteins 0.000 title description 4
-1 bisphosphonate compound Chemical class 0.000 claims abstract description 120
102000018997 Growth Hormone Human genes 0.000 claims abstract description 96
108010051696 Growth Hormone Proteins 0.000 claims abstract description 96
239000000122 growth hormone Substances 0.000 claims abstract description 96
229940011871 estrogen Drugs 0.000 claims abstract description 24
239000000262 estrogen Substances 0.000 claims abstract description 24
208000001132 Osteoporosis Diseases 0.000 claims abstract description 23
239000000556 agonist Substances 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 20
241001465754 Metazoa Species 0.000 claims abstract description 17
239000005557 antagonist Substances 0.000 claims abstract description 17
229940122361 Bisphosphonate Drugs 0.000 claims abstract description 14
101710142969 Somatoliberin Proteins 0.000 claims abstract description 14
239000000095 Growth Hormone-Releasing Hormone Substances 0.000 claims abstract description 13
102000004169 proteins and genes Human genes 0.000 claims abstract description 11
108090000623 proteins and genes Proteins 0.000 claims abstract description 11
108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims abstract description 9
102000004218 Insulin-Like Growth Factor I Human genes 0.000 claims abstract description 8
230000013632 homeostatic process Effects 0.000 claims abstract description 8
210000003205 muscle Anatomy 0.000 claims abstract description 8
208000010392 Bone Fractures Diseases 0.000 claims abstract description 7
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 7
206010019280 Heart failures Diseases 0.000 claims abstract description 7
238000011084 recovery Methods 0.000 claims abstract description 7
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims abstract description 6
208000017667 Chronic Disease Diseases 0.000 claims abstract description 5
230000032683 aging Effects 0.000 claims abstract description 5
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NWQWNCILOXTTHF-HLCSKTDOSA-N (2s)-6-amino-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-aminopropanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](N)C)C(=O)N[C@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CNC=N1 NWQWNCILOXTTHF-HLCSKTDOSA-N 0.000 claims abstract description 4
WZHKXNSOCOQYQX-FUAFALNISA-N (2s)-6-amino-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-amino-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](N)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CN=CN1 WZHKXNSOCOQYQX-FUAFALNISA-N 0.000 claims abstract description 4
RVWNMGKSNGWLOL-GIIHNPQRSA-N (2s)-6-amino-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-amino-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(2-methyl-1h-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](N)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CN=CN1 RVWNMGKSNGWLOL-GIIHNPQRSA-N 0.000 claims abstract description 4
DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 claims abstract description 4
OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims abstract description 4
108090001117 Insulin-Like Growth Factor II Proteins 0.000 claims abstract description 4
102000048143 Insulin-Like Growth Factor II Human genes 0.000 claims abstract description 4
208000008589 Obesity Diseases 0.000 claims abstract description 4
108010083553 alanyl-histidyl-(2-naphthyl)alanyl-tryptophyl-phenylalanyl-lysinamide Proteins 0.000 claims abstract description 4
229940062527 alendronate Drugs 0.000 claims abstract description 4
230000001925 catabolic effect Effects 0.000 claims abstract description 4
108010015153 growth hormone releasing hexapeptide Proteins 0.000 claims abstract description 4
108010070965 hexarelin Proteins 0.000 claims abstract description 4
230000002503 metabolic effect Effects 0.000 claims abstract description 4
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238000001356 surgical procedure Methods 0.000 claims abstract description 4
102000055006 Calcitonin Human genes 0.000 claims abstract description 3
108060001064 Calcitonin Proteins 0.000 claims abstract description 3
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims abstract description 3
229960004015 calcitonin Drugs 0.000 claims abstract description 3
239000000186 progesterone Substances 0.000 claims abstract description 3
229960003387 progesterone Drugs 0.000 claims abstract description 3
230000004044 response Effects 0.000 claims abstract description 3
102000038461 Growth Hormone-Releasing Hormone Human genes 0.000 claims abstract 4
125000000217 alkyl group Chemical group 0.000 claims description 280
239000000203 mixture Substances 0.000 claims description 231
239000001257 hydrogen Substances 0.000 claims description 176
229910052739 hydrogen Inorganic materials 0.000 claims description 176
239000000460 chlorine Substances 0.000 claims description 126
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 123
229920006395 saturated elastomer Polymers 0.000 claims description 116
229910052801 chlorine Inorganic materials 0.000 claims description 107
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
229910052760 oxygen Inorganic materials 0.000 claims description 82
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
125000001424 substituent group Chemical group 0.000 claims description 78
229910052757 nitrogen Inorganic materials 0.000 claims description 77
229910052717 sulfur Chemical group 0.000 claims description 76
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
238000000034 method Methods 0.000 claims description 67
229910052731 fluorine Inorganic materials 0.000 claims description 65
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 62
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 59
239000001301 oxygen Substances 0.000 claims description 59
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 57
239000011593 sulfur Chemical group 0.000 claims description 57
150000002431 hydrogen Chemical class 0.000 claims description 49
125000005842 heteroatom Chemical group 0.000 claims description 48
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 48
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 39
125000005843 halogen group Chemical group 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
125000001153 fluoro group Chemical group F* 0.000 claims description 30
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000000335 thiazolyl group Chemical group 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
229940079593 drug Drugs 0.000 claims description 17
125000001544 thienyl group Chemical group 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 16
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 15
230000003287 optical effect Effects 0.000 claims description 15
239000011737 fluorine Substances 0.000 claims description 13
230000012010 growth Effects 0.000 claims description 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
230000001965 increasing effect Effects 0.000 claims description 10
125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 8
125000005059 halophenyl group Chemical group 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
239000002243 precursor Substances 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 6
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 6
241000282412 Homo Species 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229940047889 isobutyramide Drugs 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 5
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 4
206010056438 Growth hormone deficiency Diseases 0.000 claims description 4
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
229950004203 droloxifene Drugs 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 claims description 4
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 4
229960004622 raloxifene Drugs 0.000 claims description 4
229960001603 tamoxifen Drugs 0.000 claims description 4
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 3
206010006895 Cachexia Diseases 0.000 claims description 3
JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 3
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 3
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 3
229950002248 idoxifene Drugs 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
238000011477 surgical intervention Methods 0.000 claims description 3
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
MPHQKNPPPRRISM-XJQHNOHDSA-N 2-amino-2-methyl-n-[(2r)-1-[2-methyl-3-oxo-3a-(pyridin-2-ylmethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]propanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](COCC=3C=CC=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=N1 MPHQKNPPPRRISM-XJQHNOHDSA-N 0.000 claims description 2
CQEJJNLXQCNLHP-XJQHNOHDSA-N 2-amino-n-[(2r)-3-[(4-chlorophenyl)methoxy]-1-oxo-1-[3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CC2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1 CQEJJNLXQCNLHP-XJQHNOHDSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
SIKMESXMGBPZKW-XJQHNOHDSA-N C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CC2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1Cl Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CC2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1Cl SIKMESXMGBPZKW-XJQHNOHDSA-N 0.000 claims description 2
CMFDKVQQVCBZTI-DDAUYOFQSA-N N-[(2R)-1-(3a-benzyl-2-ethyl-3-oxo-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(CC)N=C2CCN(C(=O)[C@@H](CC=3C4=CC=CC=C4NC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 CMFDKVQQVCBZTI-DDAUYOFQSA-N 0.000 claims description 2
UEDJSWJAKQKSHC-WIZGVZBGSA-N N-[(2R)-1-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](CC=3C4=CC=CC=C4NC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 UEDJSWJAKQKSHC-WIZGVZBGSA-N 0.000 claims description 2
GWDQWGUUUGDHLC-WIZGVZBGSA-N N-[(2R)-1-[3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](CC=3C4=CC=CC=C4NC=3)NC(=O)C(C)(C)N)CC21CC1=CC=C(F)C=C1 GWDQWGUUUGDHLC-WIZGVZBGSA-N 0.000 claims description 2
YTRLNTAGPWHUIC-WZOMIXFGSA-N N-[(2R)-1-[3a-benzyl-3-oxo-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CC2(CC=3C=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=CC=C1 YTRLNTAGPWHUIC-WZOMIXFGSA-N 0.000 claims description 2
230000006735 deficit Effects 0.000 claims description 2
JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
RHQTZSQNBZVDGW-WIZGVZBGSA-N n-[(2r)-1-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-oxo-5-phenylpentan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](CCCC=3C=CC=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 RHQTZSQNBZVDGW-WIZGVZBGSA-N 0.000 claims description 2
FUXJRKMHGRUXHB-LZDHLTRGSA-N n-[(2r)-1-(3a-benzyl-2-tert-butyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C(C)(C)C)N=C2CCN(C(=O)[C@@H](COCC=3C=CC=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 FUXJRKMHGRUXHB-LZDHLTRGSA-N 0.000 claims description 2
QWCLKHXWGCBJPQ-WZOMIXFGSA-N n-[(2r)-1-[3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](COCC=3C=CC=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=C(F)C=C1 QWCLKHXWGCBJPQ-WZOMIXFGSA-N 0.000 claims description 2
229940063238 premarin Drugs 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
SIKMESXMGBPZKW-JIPXPUAJSA-N 2-amino-n-[(2r)-1-[(3ar)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(2,4-dichlorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1Cl SIKMESXMGBPZKW-JIPXPUAJSA-N 0.000 claims 1
QUAJHCSLZMRTTM-JIPXPUAJSA-N 2-amino-n-[(2r)-1-[(3ar)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(2,4-difluorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(F)C=C1F QUAJHCSLZMRTTM-JIPXPUAJSA-N 0.000 claims 1
DLOHLXUQFHABCV-JIPXPUAJSA-N 2-amino-n-[(2r)-1-[(3ar)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(3-chlorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=CC(Cl)=C1 DLOHLXUQFHABCV-JIPXPUAJSA-N 0.000 claims 1
SIKMESXMGBPZKW-ZBLYBZFDSA-N 2-amino-n-[(2r)-1-[(3as)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(2,4-dichlorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1Cl SIKMESXMGBPZKW-ZBLYBZFDSA-N 0.000 claims 1
QUAJHCSLZMRTTM-ZBLYBZFDSA-N 2-amino-n-[(2r)-1-[(3as)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(2,4-difluorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(F)C=C1F QUAJHCSLZMRTTM-ZBLYBZFDSA-N 0.000 claims 1
DLOHLXUQFHABCV-ZBLYBZFDSA-N 2-amino-n-[(2r)-1-[(3as)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(3-chlorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=CC(Cl)=C1 DLOHLXUQFHABCV-ZBLYBZFDSA-N 0.000 claims 1
CQEJJNLXQCNLHP-ZBLYBZFDSA-N 2-amino-n-[(2r)-1-[(3as)-3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(4-chlorophenyl)methoxy]-1-oxopropan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@]2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(Cl)C=C1 CQEJJNLXQCNLHP-ZBLYBZFDSA-N 0.000 claims 1
QUAJHCSLZMRTTM-XJQHNOHDSA-N 2-amino-n-[(2r)-3-[(2,4-difluorophenyl)methoxy]-1-oxo-1-[3-oxo-3a-(pyridin-2-ylmethyl)-2-(2,2,2-trifluoroethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propan-2-yl]-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CC2(CC=3N=CC=CC=3)C(=O)N(CC(F)(F)F)N=C2CC1)OCC1=CC=C(F)C=C1F QUAJHCSLZMRTTM-XJQHNOHDSA-N 0.000 claims 1
HMBSMLATJKWAHH-UHFFFAOYSA-N 2-phenyl-1-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydro-1h-isoquinolin-6-ol Chemical compound C1CC2=CC(O)=CC=C2C(C=2C=CC(OCCN3CCCC3)=CC=2)N1C1=CC=CC=C1 HMBSMLATJKWAHH-UHFFFAOYSA-N 0.000 claims 1
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
210000003734 kidney Anatomy 0.000 claims 1
KVLLHLWBPNCVNR-WZOMIXFGSA-N n-[(2r)-1-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](COCC=3C=CC=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 KVLLHLWBPNCVNR-WZOMIXFGSA-N 0.000 claims 1
LNGBRCMHOMMAIO-WZOMIXFGSA-N n-[(2r)-1-(3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)-3-[(3,4-difluorophenyl)methoxy]-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound O=C1N(C)N=C2CCN(C(=O)[C@@H](COCC=3C=C(F)C(F)=CC=3)NC(=O)C(C)(C)N)CC21CC1=CC=CC=C1 LNGBRCMHOMMAIO-WZOMIXFGSA-N 0.000 claims 1
MPHQKNPPPRRISM-JIPXPUAJSA-N n-[(2r)-1-[(3ar)-2-methyl-3-oxo-3a-(pyridin-2-ylmethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=N1 MPHQKNPPPRRISM-JIPXPUAJSA-N 0.000 claims 1
QWCLKHXWGCBJPQ-SKCUWOTOSA-N n-[(2r)-1-[(3ar)-3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=C(F)C=C1 QWCLKHXWGCBJPQ-SKCUWOTOSA-N 0.000 claims 1
GWDQWGUUUGDHLC-RNWIMVQKSA-N n-[(2r)-1-[(3ar)-3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=C(F)C=C1 GWDQWGUUUGDHLC-RNWIMVQKSA-N 0.000 claims 1
UBEBVVBBTDUZKB-RNWIMVQKSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-ethyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)CC)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 UBEBVVBBTDUZKB-RNWIMVQKSA-N 0.000 claims 1
CMFDKVQQVCBZTI-AYWVHJORSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-ethyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)CC)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 CMFDKVQQVCBZTI-AYWVHJORSA-N 0.000 claims 1
MJGRJCMGMFLOET-MYPSAZMDSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 MJGRJCMGMFLOET-MYPSAZMDSA-N 0.000 claims 1
RHQTZSQNBZVDGW-RNWIMVQKSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-5-phenylpentan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](CCCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 RHQTZSQNBZVDGW-RNWIMVQKSA-N 0.000 claims 1
UEDJSWJAKQKSHC-RNWIMVQKSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 UEDJSWJAKQKSHC-RNWIMVQKSA-N 0.000 claims 1
LNGBRCMHOMMAIO-SKCUWOTOSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(3,4-difluorophenyl)methoxy]-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=C(F)C(F)=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 LNGBRCMHOMMAIO-SKCUWOTOSA-N 0.000 claims 1
FUXJRKMHGRUXHB-WBBHLRKXSA-N n-[(2r)-1-[(3ar)-3a-benzyl-2-tert-butyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C(C)(C)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 FUXJRKMHGRUXHB-WBBHLRKXSA-N 0.000 claims 1
MPHQKNPPPRRISM-ZBLYBZFDSA-N n-[(2r)-1-[(3as)-2-methyl-3-oxo-3a-(pyridin-2-ylmethyl)-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=N1 MPHQKNPPPRRISM-ZBLYBZFDSA-N 0.000 claims 1
QWCLKHXWGCBJPQ-DFHRPNOPSA-N n-[(2r)-1-[(3as)-3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=C(F)C=C1 QWCLKHXWGCBJPQ-DFHRPNOPSA-N 0.000 claims 1
GWDQWGUUUGDHLC-BTYSJIOQSA-N n-[(2r)-1-[(3as)-3a-[(4-fluorophenyl)methyl]-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=C(F)C=C1 GWDQWGUUUGDHLC-BTYSJIOQSA-N 0.000 claims 1
UBEBVVBBTDUZKB-BTYSJIOQSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-ethyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)CC)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 UBEBVVBBTDUZKB-BTYSJIOQSA-N 0.000 claims 1
CMFDKVQQVCBZTI-HLADLETHSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-ethyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)CC)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 CMFDKVQQVCBZTI-HLADLETHSA-N 0.000 claims 1
KVLLHLWBPNCVNR-DFHRPNOPSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 KVLLHLWBPNCVNR-DFHRPNOPSA-N 0.000 claims 1
UEDJSWJAKQKSHC-BTYSJIOQSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 UEDJSWJAKQKSHC-BTYSJIOQSA-N 0.000 claims 1
LNGBRCMHOMMAIO-DFHRPNOPSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-methyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-3-[(3,4-difluorophenyl)methoxy]-1-oxopropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=C(F)C(F)=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 LNGBRCMHOMMAIO-DFHRPNOPSA-N 0.000 claims 1
FUXJRKMHGRUXHB-XJFCNFDWSA-N n-[(2r)-1-[(3as)-3a-benzyl-2-tert-butyl-3-oxo-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@]12CN(CCC1=NN(C2=O)C(C)(C)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 FUXJRKMHGRUXHB-XJFCNFDWSA-N 0.000 claims 1
FKOGOYQRCDITFG-ZBLYBZFDSA-N n-[(2r)-1-[(3as)-3a-benzyl-3-oxo-2,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]-1-oxo-3-phenylmethoxypropan-2-yl]-2-amino-2-methylpropanamide Chemical compound C([C@@H](NC(=O)C(C)(N)C)C(=O)N1C[C@]2(CC=3C=CC=CC=3)C(=O)NN=C2CC1)OCC1=CC=CC=C1 FKOGOYQRCDITFG-ZBLYBZFDSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- 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
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Orthopedic Medicine & Surgery (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Crystallography & Structural Chemistry (AREA)
Rheumatology (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Neurology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Peptides Or Proteins (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cooling Or The Like Of Electrical Apparatus (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO19982991A 1995-12-28 1998-06-26 Dipeptidforbindelser, mellomprodukter for fremstilling av slike, anvendelse av disse for fremstilling av medikamenter for behandling samt farmasoytiske preparater inneholdende slike NO325135B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US946995P	1995-12-28	1995-12-28
PCT/IB1996/001353 WO1997024369A1 (en)	1995-12-28	1996-12-04	Growth-hormone secretagogues

Publications (3)

Publication Number	Publication Date
NO982991D0 NO982991D0 (no)	1998-06-26
NO982991L NO982991L (no)	1998-08-26
NO325135B1 true NO325135B1 (no)	2008-02-04

Family

ID=21737850

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Application Number	Title	Priority Date	Filing Date
NO19982991A NO325135B1 (no)	1995-12-28	1998-06-26	Dipeptidforbindelser, mellomprodukter for fremstilling av slike, anvendelse av disse for fremstilling av medikamenter for behandling samt farmasoytiske preparater inneholdende slike

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EP (1)	EP0869968B1 (es)
JP (2)	JP3511382B2 (es)
KR (1)	KR100320167B1 (es)
CN (1)	CN1113895C (es)
AP (2)	AP756A (es)
AR (2)	AR004367A1 (es)
AT (1)	ATE361314T1 (es)
AU (1)	AU716934B2 (es)
BG (1)	BG64055B1 (es)
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DE (1)	DE69637063T2 (es)
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GT (1)	GT199600100A (es)
HN (1)	HN1996000085A (es)
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IL (4)	IL138911A (es)
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MA (1)	MA26415A1 (es)
MX (1)	MX9805157A (es)
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NO (1)	NO325135B1 (es)
NZ (1)	NZ322172A (es)
OA (1)	OA10702A (es)
PE (1)	PE30398A1 (es)
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PT (1)	PT869968E (es)
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SI (1)	SI0869968T1 (es)
SK (1)	SK285678B6 (es)
TN (1)	TNSN96172A1 (es)
TR (1)	TR199801233T2 (es)
TW (1)	TW432073B (es)
UA (1)	UA66754C2 (es)
WO (1)	WO1997024369A1 (es)
ZA (1)	ZA9610858B (es)

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Publication number	Publication date
BR9612465A (pt)	1999-07-13
ES2285715T3 (es)	2007-11-16
ZA9610858B (en)	1998-06-23
US6110932A (en)	2000-08-29
US6313140B1 (en)	2001-11-06
JPH11501945A (ja)	1999-02-16
TR199801233T2 (xx)	1998-10-21
MX9805157A (es)	1998-10-31
US6124264A (en)	2000-09-26
HUP9901246A2 (hu)	1999-08-30
IL138911A (en)	2007-07-24
SI0869968T1 (sl)	2007-08-31
IL124449A0 (en)	1998-12-06
CN1113895C (zh)	2003-07-09
KR100320167B1 (ko)	2003-11-14
PE30398A1 (es)	1998-07-21
IS4758A (is)	1998-05-26
JP3511382B2 (ja)	2004-03-29
MY135727A (en)	2008-06-30
CA2241725C (en)	2002-06-18
IL138910A0 (en)	2001-11-25
OA10702A (en)	2001-05-07
AP9901555A0 (en)	1999-06-30
TNSN96172A1 (fr)	2005-03-15
EG24195A (en)	2008-10-14
HN1996000085A (es)	1997-06-18
CZ293423B6 (cs)	2004-04-14
CN1206422A (zh)	1999-01-27
WO1997024369A1 (en)	1997-07-10
NO982991D0 (no)	1998-06-26
DE69637063D1 (de)	2007-06-14
AR052506A2 (es)	2007-03-21
HRP960618A2 (en)	1998-04-30
BR9612465B1 (pt)	2010-08-10
JP2001213800A (ja)	2001-08-07
YU70296A (en)	1999-11-22
CO4480108A1 (es)	1997-07-09
US6107306A (en)	2000-08-22
AU7585096A (en)	1997-07-28
GT199600100A (es)	1998-06-12
IL138911A0 (en)	2001-11-25
AU716934B2 (en)	2000-03-09
TW432073B (en)	2001-05-01
CZ199598A3 (cs)	1999-05-12
ATE361314T1 (de)	2007-05-15
NO982991L (no)	1998-08-26
AP860A (en)	1999-08-06
NZ322172A (en)	2000-08-25
EP0869968B1 (en)	2007-05-02
UA66754C2 (en)	2004-06-15
PL327634A1 (en)	1998-12-21
HUP9901246A3 (en)	1999-11-29
US6278000B1 (en)	2001-08-21
BG64055B1 (bg)	2003-11-28
US6482825B2 (en)	2002-11-19
US6306875B1 (en)	2001-10-23
EP0869968A1 (en)	1998-10-14
PT869968E (pt)	2007-07-11
CA2241725A1 (en)	1997-07-10
KR19990076846A (ko)	1999-10-25
DE69637063T2 (de)	2008-02-07
IL124449A (en)	2004-06-01
MA26415A1 (fr)	2004-12-20
AR004367A1 (es)	1998-11-04
US20020049196A1 (en)	2002-04-25
DK0869968T3 (da)	2007-09-10
SA97170581B1 (ar)	2006-03-15
HRP960618B1 (en)	2007-12-31
PL186916B1 (pl)	2004-03-31
IL138909A0 (en)	2001-11-25
AP9600881A0 (en)	1997-01-31
SK87498A3 (en)	1999-08-06
BG102533A (en)	1999-09-30
SK285678B6 (sk)	2007-06-07
RS49926B (sr)	2008-09-29
AP756A (en)	1999-08-06

Publication	Publication Date	Title
NO325135B1 (no)	2008-02-04	Dipeptidforbindelser, mellomprodukter for fremstilling av slike, anvendelse av disse for fremstilling av medikamenter for behandling samt farmasoytiske preparater inneholdende slike
AU747510B2 (en)	2002-05-16	Treatment of insulin resistance with growth hormone secretagogues
JP2000516639A (ja)	2000-12-12	成長ホルモン分泌促進薬としてのジペプチド誘導体
EP1002802B1 (en)	2004-12-08	Dipeptide derivatives as growth hormone secretagogues
RU2172742C2 (ru)	2001-08-27	Стимуляторы секреции гормона роста
MXPA99012085A (es)	2001-12-04	Tratamiento de la resistencia a la insulina

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