TW200538115A - New pharmaceutical compositions for the treatment of sexual disorders - Google Patents

Info

Publication number

TW200538115A

TW200538115A TW094112651A TW94112651A TW200538115A TW 200538115 A TW200538115 A TW 200538115A TW 094112651 A TW094112651 A TW 094112651A TW 94112651 A TW94112651 A TW 94112651A TW 200538115 A TW200538115 A TW 200538115A

Authority

TW

Taiwan

Prior art keywords

individual

pharmaceutically acceptable

hydrate

necessary

acid addition

Prior art date

2004-04-22

Links

• Espacenet
• Global Dossier
• Discuss

• 238000011282 treatment Methods 0.000 title claims abstract description 83
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 66
• 208000012201 sexual and gender identity disease Diseases 0.000 title claims abstract description 6
• 208000015891 sexual disease Diseases 0.000 title claims abstract description 6
• 238000000034 method Methods 0.000 claims abstract description 40
• 239000004480 active ingredient Substances 0.000 claims abstract description 27
• 239000000203 mixture Substances 0.000 claims description 199
• 239000002253 acid Substances 0.000 claims description 192
• 150000003839 salts Chemical class 0.000 claims description 177
• 239000012453 solvate Substances 0.000 claims description 164
• 230000003287 optical effect Effects 0.000 claims description 142
• -1 NMI-775 Chemical compound 0.000 claims description 118
• 239000003814 drug Substances 0.000 claims description 97
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 89
• 208000035475 disorder Diseases 0.000 claims description 82
• 238000004519 manufacturing process Methods 0.000 claims description 82
• 230000001568 sexual effect Effects 0.000 claims description 79
• 229940079593 drug Drugs 0.000 claims description 52
• 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 description 49
• 150000001875 compounds Chemical class 0.000 claims description 44
• 150000004677 hydrates Chemical class 0.000 claims description 44
• 239000005557 antagonist Substances 0.000 claims description 43
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 36
• 239000000556 agonist Substances 0.000 claims description 32
• 239000003098 androgen Substances 0.000 claims description 29
• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 27
• 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 27
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 23
• 229940011871 estrogen Drugs 0.000 claims description 23
• 239000000262 estrogen Substances 0.000 claims description 23
• GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims description 21
• 229960003638 dopamine Drugs 0.000 claims description 19
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
• GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 claims description 18
• 229960000711 alprostadil Drugs 0.000 claims description 18
• 230000035946 sexual desire Effects 0.000 claims description 18
• 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 17
• 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
• 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 claims description 17
• 239000000674 adrenergic antagonist Substances 0.000 claims description 17
• 239000002552 dosage form Substances 0.000 claims description 17
• 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims description 13
• 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims description 13
• XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims description 13
• 239000003723 serotonin 1A agonist Substances 0.000 claims description 13
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• MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 13
• NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims description 12
• 206010024419 Libido decreased Diseases 0.000 claims description 12
• 229940083324 Selective androgen receptor modulator Drugs 0.000 claims description 12
• 239000003623 enhancer Substances 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 208000017020 hypoactive sexual desire disease Diseases 0.000 claims description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 230000003247 decreasing effect Effects 0.000 claims description 10
• 239000000336 melanocortin receptor agonist Substances 0.000 claims description 10
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 229960004622 raloxifene Drugs 0.000 claims description 9
• CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 8
• 229960004372 aripiprazole Drugs 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 8
• BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 229960002568 ethinylestradiol Drugs 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 238000002156 mixing Methods 0.000 claims description 7
• 229910052757 nitrogen Chemical group 0.000 claims description 7
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• UFFHNEZNXKJHFB-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-4h-1,4-benzoxazin-3-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3OCC(=O)NC3=CC=2)CC1 UFFHNEZNXKJHFB-UHFFFAOYSA-N 0.000 claims description 6
• MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 claims description 6
• NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 claims description 6
• XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims description 6
• 229960002629 agomelatine Drugs 0.000 claims description 6
• YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
• XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 6
• 229960002464 fluoxetine Drugs 0.000 claims description 6
• 229940029575 guanosine Drugs 0.000 claims description 6
• FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
• 208000021663 Female sexual arousal disease Diseases 0.000 claims description 5
• 208000027520 Somatoform disease Diseases 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 229960005017 olanzapine Drugs 0.000 claims description 5
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 5
• 208000027753 pain disease Diseases 0.000 claims description 5
• MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 claims description 5
• 229960001999 phentolamine Drugs 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 235000019260 propionic acid Nutrition 0.000 claims description 5
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
• 229960001534 risperidone Drugs 0.000 claims description 5
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 5
• PMIAIKWRXUGRQG-QGZVFWFLSA-N 4-[(3r)-3-[2-amino-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyrrolidin-1-yl]-1-(4-fluorophenyl)butan-1-one Chemical compound C([C@H](C1)C2=C(N=C(S2)N)C=2C=CC(F)=CC=2)CN1CCCC(=O)C1=CC=C(F)C=C1 PMIAIKWRXUGRQG-QGZVFWFLSA-N 0.000 claims description 4
• AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical group CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 4
• ULBPQWIGZUGPHU-UHFFFAOYSA-N 6-[bis(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)quinolin-2(1h)-one Chemical compound N1C(=O)C=C(C(F)(F)F)C2=CC(N(CC(F)(F)F)CC(F)(F)F)=CC=C21 ULBPQWIGZUGPHU-UHFFFAOYSA-N 0.000 claims description 4
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 4
• VGIGHGMPMUCLIQ-UHFFFAOYSA-N LSM-2183 Chemical compound C1=CC(F)=CC=C1N1CCN(CCCN2S(C=3C=CC=C4C=CC=C2C=34)(=O)=O)CC1 VGIGHGMPMUCLIQ-UHFFFAOYSA-N 0.000 claims description 4
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
• BBRBUTFBTUFFBU-LHACABTQSA-N Ornoprostil Chemical compound CCCC[C@H](C)C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(=O)OC BBRBUTFBTUFFBU-LHACABTQSA-N 0.000 claims description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
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• 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 4
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• UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 4
• 229940052760 dopamine agonists Drugs 0.000 claims description 4
• NOTIQUSPUUHHEH-UXOVVSIBSA-N dromostanolone propionate Chemical compound C([C@@H]1CC2)C(=O)[C@H](C)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)CC)[C@@]2(C)CC1 NOTIQUSPUUHHEH-UXOVVSIBSA-N 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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• 229950002951 fananserin Drugs 0.000 claims description 4
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• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical group 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 150000007857 hydrazones Chemical class 0.000 claims description 4
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• VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 claims description 4
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• XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 claims description 4
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• 239000002904 solvent Substances 0.000 claims description 4
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