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 PDFInfo
- Publication number
- NO325135B1 NO325135B1 NO19982991A NO982991A NO325135B1 NO 325135 B1 NO325135 B1 NO 325135B1 NO 19982991 A NO19982991 A NO 19982991A NO 982991 A NO982991 A NO 982991A NO 325135 B1 NO325135 B1 NO 325135B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- phenyl
- optionally substituted
- group
- methyl
- Prior art date
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- 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
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- 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
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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
- 235000020824 obesity Nutrition 0.000 claims abstract description 4
- 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
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Classifications
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- 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
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- 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
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
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- 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
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- Animal Behavior & Ethology (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cooling Or The Like Of Electrical Apparatus (AREA)
- Steroid Compounds (AREA)
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
Family Applications (1)
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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