CZ20033107A3 - Single dose aromatase inhibitor for treating infertility - Google Patents
Single dose aromatase inhibitor for treating infertility Download PDFInfo
- Publication number
- CZ20033107A3 CZ20033107A3 CZ20033107A CZ20033107A CZ20033107A3 CZ 20033107 A3 CZ20033107 A3 CZ 20033107A3 CZ 20033107 A CZ20033107 A CZ 20033107A CZ 20033107 A CZ20033107 A CZ 20033107A CZ 20033107 A3 CZ20033107 A3 CZ 20033107A3
- Authority
- CZ
- Czechia
- Prior art keywords
- aromatase inhibitor
- administered
- single dose
- use according
- amount
- Prior art date
Links
- 239000003886 aromatase inhibitor Substances 0.000 title claims abstract description 128
- 229940122815 Aromatase inhibitor Drugs 0.000 title claims abstract description 101
- 208000000509 infertility Diseases 0.000 title claims abstract description 30
- 230000036512 infertility Effects 0.000 title claims abstract description 30
- 231100000535 infertility Toxicity 0.000 title claims abstract description 30
- 230000016087 ovulation Effects 0.000 claims abstract description 38
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 claims abstract description 36
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 claims abstract description 36
- 229940028334 follicle stimulating hormone Drugs 0.000 claims abstract description 36
- 230000027758 ovulation cycle Effects 0.000 claims abstract description 21
- 230000001939 inductive effect Effects 0.000 claims abstract description 9
- 230000002513 anti-ovulatory effect Effects 0.000 claims abstract description 6
- 230000000624 ovulatory effect Effects 0.000 claims abstract description 4
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical group C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims description 37
- 229960003881 letrozole Drugs 0.000 claims description 35
- 229940011871 estrogen Drugs 0.000 claims description 33
- 239000000262 estrogen Substances 0.000 claims description 33
- 239000003112 inhibitor Substances 0.000 claims description 31
- 102000014654 Aromatase Human genes 0.000 claims description 30
- 108010078554 Aromatase Proteins 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 26
- 229940046844 aromatase inhibitors Drugs 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 14
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims description 13
- 229960001771 vorozole Drugs 0.000 claims description 13
- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical group C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 claims description 13
- 229960000255 exemestane Drugs 0.000 claims description 12
- 229960002932 anastrozole Drugs 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 230000002441 reversible effect Effects 0.000 claims description 7
- 230000003637 steroidlike Effects 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000003018 immunoassay Methods 0.000 claims description 6
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 208000007984 Female Infertility Diseases 0.000 claims 1
- 206010021928 Infertility female Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 8
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 230000002829 reductive effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract 3
- -1 sulfo, carboxyl Chemical group 0.000 description 141
- 150000001875 compounds Chemical class 0.000 description 85
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 69
- 125000000217 alkyl group Chemical group 0.000 description 62
- 239000001257 hydrogen Substances 0.000 description 41
- 229910052739 hydrogen Inorganic materials 0.000 description 41
- 229910052736 halogen Inorganic materials 0.000 description 38
- 150000002367 halogens Chemical class 0.000 description 38
- 150000003839 salts Chemical class 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
- 125000003545 alkoxy group Chemical group 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
- 150000002431 hydrogen Chemical group 0.000 description 29
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 25
- 230000000694 effects Effects 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 230000035935 pregnancy Effects 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
- 125000001589 carboacyl group Chemical group 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 210000001672 ovary Anatomy 0.000 description 12
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 11
- 230000001833 anti-estrogenic effect Effects 0.000 description 11
- 229960005309 estradiol Drugs 0.000 description 11
- 229930182833 estradiol Natural products 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000004423 acyloxy group Chemical group 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 210000004877 mucosa Anatomy 0.000 description 9
- 230000002611 ovarian Effects 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 238000013459 approach Methods 0.000 description 8
- 125000004663 dialkyl amino group Chemical group 0.000 description 8
- 238000000338 in vitro Methods 0.000 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 description 7
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 125000003226 pyrazolyl group Chemical group 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 210000000582 semen Anatomy 0.000 description 7
- 206010006187 Breast cancer Diseases 0.000 description 6
- 102000006771 Gonadotropins Human genes 0.000 description 6
- 108010086677 Gonadotropins Proteins 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 239000003098 androgen Substances 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000002622 gonadotropin Substances 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 210000003101 oviduct Anatomy 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- 230000000638 stimulation Effects 0.000 description 6
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 5
- 208000026310 Breast neoplasm Diseases 0.000 description 5
- 206010033266 Ovarian Hyperstimulation Syndrome Diseases 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000028327 secretion Effects 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 4
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- RNIZPDIBRXCMRD-OWOJBTEDSA-N 4-[(e)-2-(4-cyanophenyl)ethenyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1\C=C\C1=CC=C(C#N)C=C1 RNIZPDIBRXCMRD-OWOJBTEDSA-N 0.000 description 4
- WQUHPLQCUQJSQW-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1\C=C\C1=CC=CC=C1 WQUHPLQCUQJSQW-VOTSOKGWSA-N 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 4
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 4
- 229960005471 androstenedione Drugs 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000035558 fertility Effects 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 210000003016 hypothalamus Anatomy 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 210000000287 oocyte Anatomy 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 230000001817 pituitary effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 125000001425 triazolyl group Chemical group 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
- PYTMYKVIJXPNBD-OQKDUQJOSA-N 2-[4-[(z)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethylethanamine;hydron;2-hydroxypropane-1,2,3-tricarboxylate Chemical group OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(/Cl)C1=CC=CC=C1 PYTMYKVIJXPNBD-OQKDUQJOSA-N 0.000 description 3
- 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 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 206010036049 Polycystic ovaries Diseases 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 241000288906 Primates Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 206010042573 Superovulation Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229960003437 aminoglutethimide Drugs 0.000 description 3
- ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 229940030486 androgens Drugs 0.000 description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940046989 clomiphene citrate Drugs 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 210000002257 embryonic structure Anatomy 0.000 description 3
- 230000002357 endometrial effect Effects 0.000 description 3
- 210000004696 endometrium Anatomy 0.000 description 3
- 102000015694 estrogen receptors Human genes 0.000 description 3
- 108010038795 estrogen receptors Proteins 0.000 description 3
- 229960003399 estrone Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000004720 fertilization Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 229940094892 gonadotropins Drugs 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 3
- 230000009027 insemination Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 125000004660 phenylalkylthio group Chemical group 0.000 description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 230000001850 reproductive effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229910052717 sulfur Chemical group 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 229960001603 tamoxifen Drugs 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- KLJSYGJTEXYKEI-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)CC1=CC=C(Cl)C=C1 KLJSYGJTEXYKEI-UHFFFAOYSA-N 0.000 description 2
- ZUIWDBPWQNOHID-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)CC1=CC=C(F)C=C1 ZUIWDBPWQNOHID-UHFFFAOYSA-N 0.000 description 2
- ZNRGNQSYDXMOLN-UHFFFAOYSA-N 2-(1-imidazol-1-ylbutyl)-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound C=1C=2CCC(=O)C=2SC=1C(CCC)N1C=CN=C1 ZNRGNQSYDXMOLN-UHFFFAOYSA-N 0.000 description 2
- YVAYXSBZWQVDFO-UHFFFAOYSA-N 2-(1-imidazol-1-ylbutyl)-5,6-dihydro-4h-1-benzothiophen-7-one Chemical compound C=1C=2CCCC(=O)C=2SC=1C(CCC)N1C=CN=C1 YVAYXSBZWQVDFO-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 208000034702 Multiple pregnancies Diseases 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000005237 alkyleneamino group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- DKVSUQWCZQBWCP-QAGGRKNESA-N androsta-1,4,6-triene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 DKVSUQWCZQBWCP-QAGGRKNESA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000003756 cervix mucus Anatomy 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000002124 endocrine Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 239000000328 estrogen antagonist Substances 0.000 description 2
- CBBNWSFYMXZPOX-UHFFFAOYSA-N ethyl 4-imidazo[1,5-a]pyridin-5-ylbenzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC=CC2=CN=CN12 CBBNWSFYMXZPOX-UHFFFAOYSA-N 0.000 description 2
- 229940087476 femara Drugs 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 210000005075 mammary gland Anatomy 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- AZKDTTQQTKDXLH-UHFFFAOYSA-N naphthalene-2-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- 125000005412 pyrazyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 230000000365 steroidogenetic effect Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- YMXUXYULYQGUGS-UHFFFAOYSA-N 1,1-dimethyl-2-oxo-8-(1,2,4-triazol-1-ylmethyl)benzo[e][1]benzofuran-7-carbonitrile Chemical compound C=1C2=C3C(C)(C)C(=O)OC3=CC=C2C=C(C#N)C=1CN1C=NC=N1 YMXUXYULYQGUGS-UHFFFAOYSA-N 0.000 description 1
- SCDITOXRDOZPKX-UHFFFAOYSA-N 1,1-dimethyl-2-oxo-8-(1,2,4-triazol-1-ylmethyl)benzo[e][1]benzofuran-7-carboxamide Chemical compound C=1C2=C3C(C)(C)C(=O)OC3=CC=C2C=C(C(N)=O)C=1CN1C=NC=N1 SCDITOXRDOZPKX-UHFFFAOYSA-N 0.000 description 1
- UQSVVKDTVCZJEH-UHFFFAOYSA-N 1,1-dimethyl-8-(1,2,4-triazol-1-ylmethyl)benzo[e][1]benzofuran-2-one Chemical compound C=1C2=C3C(C)(C)C(=O)OC3=CC=C2C=CC=1CN1C=NC=N1 UQSVVKDTVCZJEH-UHFFFAOYSA-N 0.000 description 1
- BSBDNBKZSCBTHZ-UHFFFAOYSA-N 1,11-bis[5-(1-imidazol-1-ylbutyl)thiophen-2-yl]undecan-6-one Chemical compound C1=CN=CN1C(CCC)C(S1)=CC=C1CCCCCC(=O)CCCCCC(S1)=CC=C1C(CCC)N1C=CN=C1 BSBDNBKZSCBTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- LMRXXRYKCJAFJA-UHFFFAOYSA-N 1,5-bis[5-(1-imidazol-1-ylbutyl)thiophen-2-yl]pentan-3-one Chemical compound N1(C=NC=C1)C(CCC)C1=CC=C(S1)CCC(=O)CCC=1SC(=CC=1)C(CCC)N1C=NC=C1 LMRXXRYKCJAFJA-UHFFFAOYSA-N 0.000 description 1
- BGTCPZFJLHXHAN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)CC1=CC=C(Cl)C=C1Cl BGTCPZFJLHXHAN-UHFFFAOYSA-N 0.000 description 1
- FYMBKKQKNUQWNK-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(2-methylpropyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CC(C)C)C(=O)C2CC21C1=CC=C(N)C=C1 FYMBKKQKNUQWNK-UHFFFAOYSA-N 0.000 description 1
- WUHIUYRMTKSZGJ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(cyclohexylmethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound C1=CC(N)=CC=C1C1(C(N(CC2CCCCC2)C2=O)=O)C2C1 WUHIUYRMTKSZGJ-UHFFFAOYSA-N 0.000 description 1
- RRVMZLDBVUOPFQ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-heptyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCC)C(=O)C2CC21C1=CC=C(N)C=C1 RRVMZLDBVUOPFQ-UHFFFAOYSA-N 0.000 description 1
- TYSQCNSELGOQRS-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-fluoro-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(C(F)C=1C=CC(Cl)=CC=1)(O)CN1C=NC=N1 TYSQCNSELGOQRS-UHFFFAOYSA-N 0.000 description 1
- OOKGRWOZLMQTNP-UHFFFAOYSA-N 1-(6-bromo-3,4-dihydronaphthalen-1-yl)imidazole Chemical compound C=1CCC2=CC(Br)=CC=C2C=1N1C=CN=C1 OOKGRWOZLMQTNP-UHFFFAOYSA-N 0.000 description 1
- HBBJZCDSUBUTKH-UHFFFAOYSA-N 1-(6-chloro-3,4-dihydronaphthalen-1-yl)imidazole Chemical compound C=1CCC2=CC(Cl)=CC=C2C=1N1C=CN=C1 HBBJZCDSUBUTKH-UHFFFAOYSA-N 0.000 description 1
- OEOHLZRIMGQSQN-UHFFFAOYSA-N 1-[1-(4-bromothiophen-2-yl)butyl]imidazole Chemical compound C1=CN=CN1C(CCC)C1=CC(Br)=CS1 OEOHLZRIMGQSQN-UHFFFAOYSA-N 0.000 description 1
- KWCDLCTVQUKLQA-UHFFFAOYSA-N 1-[1-(5-bromothiophen-2-yl)butyl]imidazole Chemical compound C1=CN=CN1C(CCC)C1=CC=C(Br)S1 KWCDLCTVQUKLQA-UHFFFAOYSA-N 0.000 description 1
- LTXCLNVZGCEJCO-UHFFFAOYSA-N 1-[1-[2-[(2,4-dichlorophenyl)methoxy]-5-nitrophenyl]butyl]imidazole Chemical compound C1=CN=CN1C(CCC)C1=CC([N+]([O-])=O)=CC=C1OCC1=CC=C(Cl)C=C1Cl LTXCLNVZGCEJCO-UHFFFAOYSA-N 0.000 description 1
- SSGJTZPZLQFZDC-UHFFFAOYSA-N 1-[2-[(4-chloro-2-fluorophenyl)methyl]-2-fluoro-3-(1,2,4-triazol-1-yl)propyl]-1,2,4-triazole Chemical compound FC1=CC(Cl)=CC=C1CC(F)(CN1N=CN=C1)CN1N=CN=C1 SSGJTZPZLQFZDC-UHFFFAOYSA-N 0.000 description 1
- HGYXIKJTHYSMTM-UHFFFAOYSA-N 1-[2-[(4-chlorophenyl)methyl]-2-fluoro-3-(1,2,4-triazol-1-yl)propyl]-1,2,4-triazole Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(F)CC1=CC=C(Cl)C=C1 HGYXIKJTHYSMTM-UHFFFAOYSA-N 0.000 description 1
- XMQXCGZASBUFEG-UHFFFAOYSA-N 1-[2-[(4-chlorophenyl)methyl]-3-(1,2,4-triazol-1-yl)propyl]-1,2,4-triazole Chemical compound C1=CC(Cl)=CC=C1CC(CN1N=CN=C1)CN1N=CN=C1 XMQXCGZASBUFEG-UHFFFAOYSA-N 0.000 description 1
- LMFWQPSZIAYKPG-UHFFFAOYSA-N 1-[2-fluoro-2-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]-3-(1,2,4-triazol-1-yl)propyl]-1,2,4-triazole Chemical compound FC1=CC(C(F)(F)F)=CC=C1CC(F)(CN1N=CN=C1)CN1N=CN=C1 LMFWQPSZIAYKPG-UHFFFAOYSA-N 0.000 description 1
- VRMIMFRRBJUIFN-UHFFFAOYSA-N 1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)propan-2-ol Chemical compound C1=NC=NN1CC(CN1N=CN=C1)(O)CC1=CC=C(C(F)(F)F)C=C1F VRMIMFRRBJUIFN-UHFFFAOYSA-N 0.000 description 1
- SXNLKIAUDDWIQY-UHFFFAOYSA-N 1-[4-(1-imidazol-1-ylbutyl)phenyl]-2-methylpropan-1-one Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(=O)C(C)C)C=C1 SXNLKIAUDDWIQY-UHFFFAOYSA-N 0.000 description 1
- RZVORLWZHCFKTQ-UHFFFAOYSA-N 1-[4-(1-imidazol-1-ylbutyl)phenyl]heptan-1-one Chemical compound C1=CC(C(=O)CCCCCC)=CC=C1C(CCC)N1C=NC=C1 RZVORLWZHCFKTQ-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- LXDVAPIKHNHFRC-UHFFFAOYSA-N 2,3-dimethyl-4-(1h-1,2,4-triazol-5-ylmethyl)-1-benzofuran-7-carbonitrile Chemical compound C=12C(C)=C(C)OC2=C(C#N)C=CC=1CC=1N=CNN=1 LXDVAPIKHNHFRC-UHFFFAOYSA-N 0.000 description 1
- ZOCYWUXXXWKLOB-UHFFFAOYSA-N 2-(1-imidazol-1-ylbutyl)-6,7-dihydro-5h-1-benzothiophen-4-one Chemical compound C=1C(C(CCC2)=O)=C2SC=1C(CCC)N1C=CN=C1 ZOCYWUXXXWKLOB-UHFFFAOYSA-N 0.000 description 1
- DNIUQBFREMONOO-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-fluorophenoxy)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1OC(N1N=CN=C1)C(C=1C=CC(Cl)=CC=1)(O)CN1C=NC=N1 DNIUQBFREMONOO-UHFFFAOYSA-N 0.000 description 1
- YTDYWNHRVVPGPX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-phenyl-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=CC=CC=1C(N1N=CN=C1)C(C=1C=CC(Cl)=CC=1)(O)CN1C=NC=N1 YTDYWNHRVVPGPX-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GRSURYKRCHQYQO-UHFFFAOYSA-N 2-[3-(1,3-dihydro-1,2,4-triazol-2-ylmethyl)-5-(2-hydroxypropan-2-yl)phenyl]-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC(C(C)(O)C)=CC(CN2NC=NC2)=C1 GRSURYKRCHQYQO-UHFFFAOYSA-N 0.000 description 1
- MTUMUYALKNFFBJ-UHFFFAOYSA-N 2-[3-(2-cyanopropan-2-yl)-5-(imidazol-1-ylmethyl)phenyl]-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2C=NC=C2)=C1 MTUMUYALKNFFBJ-UHFFFAOYSA-N 0.000 description 1
- NLFXBKUOMSROAY-UHFFFAOYSA-N 2-[4-(1-imidazol-1-ylbutyl)phenyl]acetonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC=C(CC#N)C=C1 NLFXBKUOMSROAY-UHFFFAOYSA-N 0.000 description 1
- JJHFOBGMWLICBW-UHFFFAOYSA-N 2-[[2-[(2,4-dichlorophenyl)methoxy]-5-nitrophenyl]methyl]-1h-imidazole Chemical compound N=1C=CNC=1CC1=CC([N+](=O)[O-])=CC=C1OCC1=CC=C(Cl)C=C1Cl JJHFOBGMWLICBW-UHFFFAOYSA-N 0.000 description 1
- GVIRAXRGZUXHCI-UHFFFAOYSA-N 2-acetyloxycarbonylbenzoic acid Chemical compound CC(=O)OC(=O)C1=CC=CC=C1C(O)=O GVIRAXRGZUXHCI-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- RFOXZBAMVWSHFS-UHFFFAOYSA-N 2-methyl-4-(tetrazol-1-yl)naphthalene-1-carbonitrile Chemical compound C(#N)C1=C(C=C(C2=CC=CC=C12)N1N=NN=C1)C RFOXZBAMVWSHFS-UHFFFAOYSA-N 0.000 description 1
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-WFGJKAKNSA-N 3,3,3-trideuterio-2-(trideuteriomethyl)propanenitrile Chemical compound [2H]C([2H])([2H])C(C#N)C([2H])([2H])[2H] LRDFRRGEGBBSRN-WFGJKAKNSA-N 0.000 description 1
- FHQDEFBZJCMUBT-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-(1,2,4-triazol-1-ylmethyl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(CN1N=CN=C1)C(C)C1=CC=C(Cl)C=C1 FHQDEFBZJCMUBT-UHFFFAOYSA-N 0.000 description 1
- WGMKCOBERUOCDU-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzoic acid Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(O)=O)C=C1OCC1=CC=C(Cl)C=C1Cl WGMKCOBERUOCDU-UHFFFAOYSA-N 0.000 description 1
- SLMAISNKTUTWGH-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C#N)C=C1OCC1=CC=C(Cl)C=C1Cl SLMAISNKTUTWGH-UHFFFAOYSA-N 0.000 description 1
- UYXQPTVIYDTLQU-UHFFFAOYSA-N 3-[(3-bromophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C#N)C=C1OCC1=CC=CC(Br)=C1 UYXQPTVIYDTLQU-UHFFFAOYSA-N 0.000 description 1
- PBBZLCQNAYKOBC-UHFFFAOYSA-N 3-[(4-bromophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)-n-phenylbenzamide Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1OCC1=CC=C(Br)C=C1 PBBZLCQNAYKOBC-UHFFFAOYSA-N 0.000 description 1
- DXRNOAFYSLIBNH-UHFFFAOYSA-N 3-[(4-bromophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzoic acid Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(O)=O)C=C1OCC1=CC=C(Br)C=C1 DXRNOAFYSLIBNH-UHFFFAOYSA-N 0.000 description 1
- WHZUUTWIJIIJAD-UHFFFAOYSA-N 3-[(4-bromophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C#N)C=C1OCC1=CC=C(Br)C=C1 WHZUUTWIJIIJAD-UHFFFAOYSA-N 0.000 description 1
- KIRBKZSRPQZIQA-UHFFFAOYSA-N 3-[(4-chlorophenyl)methoxy]-4-(1-imidazol-1-ylpentyl)-1-oxidopyridin-1-ium Chemical compound C1=CN=CN1C(CCCC)C1=CC=[N+]([O-])C=C1OCC1=CC=C(Cl)C=C1 KIRBKZSRPQZIQA-UHFFFAOYSA-N 0.000 description 1
- XEUFDRCKMFNEAF-UHFFFAOYSA-N 3-[(4-chlorophenyl)methoxy]-4-(1-imidazol-1-ylpentyl)pyridine Chemical compound C1=CN=CN1C(CCCC)C1=CC=NC=C1OCC1=CC=C(Cl)C=C1 XEUFDRCKMFNEAF-UHFFFAOYSA-N 0.000 description 1
- AFPQIHGRKOGMDW-UHFFFAOYSA-N 3-[(4-chlorophenyl)methoxy]-4-(1-imidazol-1-ylpentyl)pyridine-2-carbonitrile Chemical compound C1=CN=CN1C(CCCC)C1=CC=NC(C#N)=C1OCC1=CC=C(Cl)C=C1 AFPQIHGRKOGMDW-UHFFFAOYSA-N 0.000 description 1
- SNTLOFNFOJJWNH-UHFFFAOYSA-N 4-(1-imidazol-1-ylbutyl)benzaldehyde Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C=O)C=C1 SNTLOFNFOJJWNH-UHFFFAOYSA-N 0.000 description 1
- FUFISTOVGRWOOB-UHFFFAOYSA-N 4-(1-imidazol-1-ylethenyl)benzonitrile Chemical group C1=CN=CN1C(=C)C1=CC=C(C#N)C=C1 FUFISTOVGRWOOB-UHFFFAOYSA-N 0.000 description 1
- CJBGEQVKMRSXME-UHFFFAOYSA-N 4-(1h-imidazol-2-ylmethyl)-2,3-dimethyl-1-benzofuran-7-carbonitrile Chemical compound C=12C(C)=C(C)OC2=C(C#N)C=CC=1CC1=NC=CN1 CJBGEQVKMRSXME-UHFFFAOYSA-N 0.000 description 1
- MSBHAFLXPUACPT-UHFFFAOYSA-N 4-(1h-imidazol-2-ylmethyl)-2,3-dimethyl-1-benzofuran-7-carboxamide Chemical compound C=12C(C)=C(C)OC2=C(C(N)=O)C=CC=1CC1=NC=CN1 MSBHAFLXPUACPT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HZGNVEQPTRILJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-1,3-bis(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C=1C=C(F)C=CC=1CC(N1N=CN=C1)C(C=1C(=CC(=CC=1)C(F)(F)F)F)(O)CN1C=NC=N1 HZGNVEQPTRILJZ-UHFFFAOYSA-N 0.000 description 1
- MCZMEBFOEKKHJG-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)aniline Chemical compound C1=CC(N)=CC=C1C1N2C=NC=C2CCC1 MCZMEBFOEKKHJG-UHFFFAOYSA-N 0.000 description 1
- RWCWFQNNYZXFIT-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1N2C=NC=C2CCC1 RWCWFQNNYZXFIT-UHFFFAOYSA-N 0.000 description 1
- PDWHXGHLLWRDJT-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1N2C=NC=C2CCC1 PDWHXGHLLWRDJT-UHFFFAOYSA-N 0.000 description 1
- KLIYHHIBTVVFPB-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1N2C=NC=C2CCC1 KLIYHHIBTVVFPB-UHFFFAOYSA-N 0.000 description 1
- ZXBBOGUUSPLLLD-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-7-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1CC2=CN=CN2CC1 ZXBBOGUUSPLLLD-UHFFFAOYSA-N 0.000 description 1
- COQBJENDMHZDCW-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-7-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1CC2=CN=CN2CC1 COQBJENDMHZDCW-UHFFFAOYSA-N 0.000 description 1
- WGXAKTGJPQPASY-UHFFFAOYSA-N 4-(5-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-1-yl)benzonitrile Chemical compound C(C1=CC=CC=C1)C1CCCC=2N1C=NC=2C1=CC=C(C=C1)C#N WGXAKTGJPQPASY-UHFFFAOYSA-N 0.000 description 1
- ORKOENNBLBEILV-UHFFFAOYSA-N 4-(5-methylsulfanyl-7,8-dihydro-6h-imidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1CCC2=CN=CN2C1(SC)C1=CC=C(C#N)C=C1 ORKOENNBLBEILV-UHFFFAOYSA-N 0.000 description 1
- VKTGFDSNAZLZBO-UHFFFAOYSA-N 4-(7,8-dihydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CCCC2=CN=CN12 VKTGFDSNAZLZBO-UHFFFAOYSA-N 0.000 description 1
- CJDIEJNOENTRRJ-UHFFFAOYSA-N 4-(tetrazol-2-ylmethyl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1CN1N=NC=N1 CJDIEJNOENTRRJ-UHFFFAOYSA-N 0.000 description 1
- IEASHUXECSOQFD-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)aniline Chemical compound C1=CN=CN1C(CCC)C1=CC(N)=CC=C1OCC1=CC=C(Cl)C=C1Cl IEASHUXECSOQFD-UHFFFAOYSA-N 0.000 description 1
- MIIUOGQCXLTIRL-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC(C#N)=CC=C1OCC1=CC=C(Cl)C=C1Cl MIIUOGQCXLTIRL-UHFFFAOYSA-N 0.000 description 1
- BPFATGLSQHIYJC-UHFFFAOYSA-N 4-[(3-bromophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC(C#N)=CC=C1OCC1=CC=CC(Br)=C1 BPFATGLSQHIYJC-UHFFFAOYSA-N 0.000 description 1
- KKQFBZBYSONUOL-UHFFFAOYSA-N 4-[(4-bromophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)-n-phenylbenzamide Chemical compound C1=CN=CN1C(CCC)C1=CC(C(=O)NC=2C=CC=CC=2)=CC=C1OCC1=CC=C(Br)C=C1 KKQFBZBYSONUOL-UHFFFAOYSA-N 0.000 description 1
- UCIMJZDDNPQGLO-UHFFFAOYSA-N 4-[(4-bromophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)benzoic acid Chemical compound C1=CN=CN1C(CCC)C1=CC(C(O)=O)=CC=C1OCC1=CC=C(Br)C=C1 UCIMJZDDNPQGLO-UHFFFAOYSA-N 0.000 description 1
- LVYSTELTEDIZHK-UHFFFAOYSA-N 4-[(4-bromophenyl)methoxy]-3-(1-imidazol-1-ylbutyl)benzonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC(C#N)=CC=C1OCC1=CC=C(Br)C=C1 LVYSTELTEDIZHK-UHFFFAOYSA-N 0.000 description 1
- QESYKHACCJXMIR-UHFFFAOYSA-N 4-[1-(1,2,4-triazol-1-yl)-3-[4-(trifluoromethoxy)phenyl]propan-2-yl]benzonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1CC(C=1C=CC(=CC=1)C#N)CN1N=CN=C1 QESYKHACCJXMIR-UHFFFAOYSA-N 0.000 description 1
- OLOWIHUVIYDNLC-UHFFFAOYSA-N 4-[1-(1,2,4-triazol-1-yl)-3-[4-(trifluoromethyl)phenyl]propan-2-yl]benzonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(C=1C=CC(=CC=1)C#N)CN1N=CN=C1 OLOWIHUVIYDNLC-UHFFFAOYSA-N 0.000 description 1
- KDZFXKZZAPNLGT-UHFFFAOYSA-N 4-[1-(1,2,4-triazol-1-yl)-3-[5-(trifluoromethyl)pyridin-2-yl]propan-2-yl]benzonitrile Chemical compound N1=CC(C(F)(F)F)=CC=C1CC(C=1C=CC(=CC=1)C#N)CN1N=CN=C1 KDZFXKZZAPNLGT-UHFFFAOYSA-N 0.000 description 1
- BVVAHEKMSDKCOR-UHFFFAOYSA-N 4-[1-(1,3-thiazol-5-yl)ethenyl]benzonitrile Chemical group C=1C=C(C#N)C=CC=1C(=C)C1=CN=CS1 BVVAHEKMSDKCOR-UHFFFAOYSA-N 0.000 description 1
- LHVILYOGVWOZLJ-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CC(C=1C=CC(=CC=1)C#N)CN1N=CN=C1 LHVILYOGVWOZLJ-UHFFFAOYSA-N 0.000 description 1
- GWAJQPYEERMXQR-UHFFFAOYSA-N 4-[2-(4-cyanophenyl)-3-(1,2,4-triazol-1-yl)propyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CC(C=1C=CC(=CC=1)C#N)CN1N=CN=C1 GWAJQPYEERMXQR-UHFFFAOYSA-N 0.000 description 1
- HBHQVBJOTFGANG-UHFFFAOYSA-N 4-[2-adamantylidene(1h-1,2,4-triazol-5-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C1=NNC=N1)=C1C(C2)CC3CC2CC1C3 HBHQVBJOTFGANG-UHFFFAOYSA-N 0.000 description 1
- SGJBCKXHYQLKOV-UHFFFAOYSA-N 4-[2-adamantylidene(1h-imidazol-2-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1NC=CN=1)=C1C(C2)CC3CC2CC1C3 SGJBCKXHYQLKOV-UHFFFAOYSA-N 0.000 description 1
- IHEOJYWMFMRGNV-UHFFFAOYSA-N 4-[cycloheptylidene(1h-1,2,4-triazol-5-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C1=NNC=N1)=C1CCCCCC1 IHEOJYWMFMRGNV-UHFFFAOYSA-N 0.000 description 1
- YBHKTFSZXZFOBE-UHFFFAOYSA-N 4-[cycloheptylidene(1h-imidazol-2-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1NC=CN=1)=C1CCCCCC1 YBHKTFSZXZFOBE-UHFFFAOYSA-N 0.000 description 1
- FTLACCKTVQQRND-UHFFFAOYSA-N 4-[cyclohexylidene(1h-1,2,4-triazol-5-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C1=NNC=N1)=C1CCCCC1 FTLACCKTVQQRND-UHFFFAOYSA-N 0.000 description 1
- XGRWCPICEMCGNO-UHFFFAOYSA-N 4-[cyclohexylidene(1h-imidazol-2-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1NC=CN=1)=C1CCCCC1 XGRWCPICEMCGNO-UHFFFAOYSA-N 0.000 description 1
- RPYKHVRRSHFQOX-UHFFFAOYSA-N 4-[cyclohexylidene(2h-triazol-4-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1N=NNC=1)=C1CCCCC1 RPYKHVRRSHFQOX-UHFFFAOYSA-N 0.000 description 1
- HFPSNZHPJMEOQW-UHFFFAOYSA-N 4-[cyclopentylidene(1h-1,2,4-triazol-5-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C1=NNC=N1)=C1CCCC1 HFPSNZHPJMEOQW-UHFFFAOYSA-N 0.000 description 1
- PYVFKXCBZBKIIG-UHFFFAOYSA-N 4-[cyclopentylidene(1h-imidazol-2-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1NC=CN=1)=C1CCCC1 PYVFKXCBZBKIIG-UHFFFAOYSA-N 0.000 description 1
- ROLYNIATTYUUTO-UHFFFAOYSA-N 4-[cyclopentylidene(2h-triazol-4-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1N=NNC=1)=C1CCCC1 ROLYNIATTYUUTO-UHFFFAOYSA-N 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- MQHXPIGQRZNXAD-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC2=CN=CN12 MQHXPIGQRZNXAD-UHFFFAOYSA-N 0.000 description 1
- JVORFZLMRBKKDI-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC2=CN=CN12 JVORFZLMRBKKDI-UHFFFAOYSA-N 0.000 description 1
- UBSPPJXJSOOGNV-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC2=CN=CN12 UBSPPJXJSOOGNV-UHFFFAOYSA-N 0.000 description 1
- ZRBDYBQIBBZJBE-UHFFFAOYSA-N 4-imidazo[1,5-a]pyridin-5-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC2=CN=CN12 ZRBDYBQIBBZJBE-UHFFFAOYSA-N 0.000 description 1
- MMWHSRACPBFMEB-UHFFFAOYSA-N 5-(1,2-thiazol-5-yl)-7,8-dihydronaphthalene-2-carbonitrile Chemical compound C=1CCC2=CC(C#N)=CC=C2C=1C1=CC=NS1 MMWHSRACPBFMEB-UHFFFAOYSA-N 0.000 description 1
- PPNWHVHFTROXIF-UHFFFAOYSA-N 5-(1,3-thiazol-5-yl)-7,8-dihydronaphthalene-2-carbonitrile Chemical compound C=1CCC2=CC(C#N)=CC=C2C=1C1=CN=CS1 PPNWHVHFTROXIF-UHFFFAOYSA-N 0.000 description 1
- MBWMOKMBDFYPEK-UHFFFAOYSA-N 5-(1-imidazol-1-ylbutyl)-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1C(CCC)N1C=CN=C1 MBWMOKMBDFYPEK-UHFFFAOYSA-N 0.000 description 1
- FKXDSFKZBZYXSS-UHFFFAOYSA-N 5-(1-imidazol-1-ylbutyl)thiophene-2-carbonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C#N)S1 FKXDSFKZBZYXSS-UHFFFAOYSA-N 0.000 description 1
- LMSZUNOXOCYFNY-UHFFFAOYSA-N 5-(1-imidazol-1-ylbutyl)thiophene-3-carbonitrile Chemical compound C1=CN=CN1C(CCC)C1=CC(C#N)=CS1 LMSZUNOXOCYFNY-UHFFFAOYSA-N 0.000 description 1
- YOOMCJAOBXMFKR-UHFFFAOYSA-N 5-(1h-imidazol-2-ylmethyl)-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1CC1=NC=CN1 YOOMCJAOBXMFKR-UHFFFAOYSA-N 0.000 description 1
- IQGZMZUNSFBLQG-UHFFFAOYSA-N 5-(4-aminophenyl)-3-(cyclohexylmethyl)-3-azabicyclo[3.1.1]heptane-2,4-dione Chemical compound C1=CC(N)=CC=C1C1(C(N(CC2CCCCC2)C2=O)=O)CC2C1 IQGZMZUNSFBLQG-UHFFFAOYSA-N 0.000 description 1
- QQMGXUVJMQNZGE-UHFFFAOYSA-N 5-(4-aminophenyl)-3-cyclohexyl-3-azabicyclo[3.1.1]heptane-2,4-dione Chemical compound C1=CC(N)=CC=C1C1(C(N(C2CCCCC2)C2=O)=O)CC2C1 QQMGXUVJMQNZGE-UHFFFAOYSA-N 0.000 description 1
- DDJKKIKJQNRBPR-UHFFFAOYSA-N 5-(4-aminophenyl)-3-decyl-3-azabicyclo[3.1.1]heptane-2,4-dione Chemical compound O=C1N(CCCCCCCCCC)C(=O)C(C2)CC21C1=CC=C(N)C=C1 DDJKKIKJQNRBPR-UHFFFAOYSA-N 0.000 description 1
- BTRJMGJWUJMOON-UHFFFAOYSA-N 5-(4-aminophenyl)-3-methyl-3-azabicyclo[3.1.1]heptane-2,4-dione Chemical compound O=C1N(C)C(=O)C(C2)CC21C1=CC=C(N)C=C1 BTRJMGJWUJMOON-UHFFFAOYSA-N 0.000 description 1
- XXRDNGWQLOVWDB-UHFFFAOYSA-N 5-(4-aminophenyl)-3-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione Chemical compound O=C1N(CCC)C(=O)C(C2)CC21C1=CC=C(N)C=C1 XXRDNGWQLOVWDB-UHFFFAOYSA-N 0.000 description 1
- CETYHXLCJBBAHU-UHFFFAOYSA-N 5-(4-bromophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1=CC(Br)=CC=C1C1N2C=NC=C2CCC1 CETYHXLCJBBAHU-UHFFFAOYSA-N 0.000 description 1
- YLDXLXMVHMRCMZ-UHFFFAOYSA-N 5-(4-imidazol-1-ylheptan-4-yl)-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1C(CCC)(CCC)N1C=CN=C1 YLDXLXMVHMRCMZ-UHFFFAOYSA-N 0.000 description 1
- MPVPVMCQPGYYCE-UHFFFAOYSA-N 5-(4-methylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine Chemical compound C1=CC(C)=CC=C1C1N2C=NC=C2CCC1 MPVPVMCQPGYYCE-UHFFFAOYSA-N 0.000 description 1
- HNAZNCPNTCKBBN-UHFFFAOYSA-N 5-[(4-chlorophenyl)methoxy]-4-(1-imidazol-1-ylpentyl)pyridine-2-carbonitrile Chemical compound C1=CN=CN1C(CCCC)C1=CC(C#N)=NC=C1OCC1=CC=C(Cl)C=C1 HNAZNCPNTCKBBN-UHFFFAOYSA-N 0.000 description 1
- JLASXAPCAPHSOU-UHFFFAOYSA-N 5-[cyclohexylidene(1h-imidazol-2-yl)methyl]thiophene-2-carbonitrile Chemical compound S1C(C#N)=CC=C1C(C=1NC=CN=1)=C1CCCCC1 JLASXAPCAPHSOU-UHFFFAOYSA-N 0.000 description 1
- WMFHHZOZJZSADW-UHFFFAOYSA-N 5-imidazol-1-yl-7,8-dihydronaphthalene-2-carbonitrile Chemical compound C=1CCC2=CC(C#N)=CC=C2C=1N1C=CN=C1 WMFHHZOZJZSADW-UHFFFAOYSA-N 0.000 description 1
- KHMCICPVZFNPNB-UHFFFAOYSA-N 6-(1-imidazol-1-ylbutyl)-1-benzofuran-3-one Chemical compound C=1C=C2C(=O)COC2=CC=1C(CCC)N1C=CN=C1 KHMCICPVZFNPNB-UHFFFAOYSA-N 0.000 description 1
- KVDCWCMUYKGNIH-UHFFFAOYSA-N 6-(1-imidazol-1-ylbutyl)-2,3-dihydroinden-1-one Chemical compound C=1C=C2CCC(=O)C2=CC=1C(CCC)N1C=CN=C1 KVDCWCMUYKGNIH-UHFFFAOYSA-N 0.000 description 1
- MIGYFBCROVCJFD-UHFFFAOYSA-N 6-(1-imidazol-1-ylbutyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C=1C=C2C(=O)CCCC2=CC=1C(CCC)N1C=CN=C1 MIGYFBCROVCJFD-UHFFFAOYSA-N 0.000 description 1
- NNHWOQMPSJJUND-REZTVBANSA-N 6-[(z)-2-(4-cyanophenyl)-3-(1,2,4-triazol-1-yl)prop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC(C#N)=CC=C1C(\CN1N=CN=C1)=C\C1=CC=C(C#N)C=N1 NNHWOQMPSJJUND-REZTVBANSA-N 0.000 description 1
- DWGGOFUNFXLTKF-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)-3-(1,2,4-triazol-1-yl)propyl]pyridine-3-carbonitrile Chemical compound C1=CC(C#N)=CC=C1C(CN1N=CN=C1)CC1=CC=C(C#N)C=N1 DWGGOFUNFXLTKF-UHFFFAOYSA-N 0.000 description 1
- CNJANAFWPLWMHY-UHFFFAOYSA-N 6-[imidazol-1-yl(phenyl)methyl]-1-methylbenzotriazole Chemical compound C1=C2N(C)N=NC2=CC=C1C(N1C=NC=C1)C1=CC=CC=C1 CNJANAFWPLWMHY-UHFFFAOYSA-N 0.000 description 1
- WFNLGYMREJDRFJ-UHFFFAOYSA-N 7-(1-imidazol-1-ylbutyl)-2,3-dihydroinden-1-one Chemical compound C=1C=CC=2CCC(=O)C=2C=1C(CCC)N1C=CN=C1 WFNLGYMREJDRFJ-UHFFFAOYSA-N 0.000 description 1
- KVOQSZGIKSVKJY-UHFFFAOYSA-N 8-[bis(1,2,4-triazol-1-yl)methyl]-1,1-dimethyl-2-oxobenzo[e][1]benzofuran-7-carbonitrile Chemical compound C=1C2=C3C(C)(C)C(=O)OC3=CC=C2C=C(C#N)C=1C(N1N=CN=C1)N1C=NC=N1 KVOQSZGIKSVKJY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102100032187 Androgen receptor Human genes 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010062767 Hypophysitis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108010057021 Menotropins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MNRAVQTVTRSWIS-UHFFFAOYSA-N N#CC1=CC=C(CC(C(CN2N=CN=C2)(O)OC(C=CC(F)=C2)=C2F)N2N=CN=C2)C=C1 Chemical compound N#CC1=CC=C(CC(C(CN2N=CN=C2)(O)OC(C=CC(F)=C2)=C2F)N2N=CN=C2)C=C1 MNRAVQTVTRSWIS-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 206010046782 Uterine enlargement Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HNWGYDJRCZATGH-UHFFFAOYSA-N [4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1N2C=NC=C2CCC1 HNWGYDJRCZATGH-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229940078010 arimidex Drugs 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 229940087620 aromasin Drugs 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- HQRQUBDKFORHQM-UHFFFAOYSA-N butyl 4-(1-imidazol-1-ylbutyl)benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1C(CCC)N1C=NC=C1 HQRQUBDKFORHQM-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 230000032692 embryo implantation Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002159 estradiols Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- FSLPUIQRTFZEMT-UHFFFAOYSA-N ethyl 2-[5-(4-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-6-yl]acetate Chemical compound CCOC(=O)CC1CCC2=CN=CN2C1C1=CC=C(C#N)C=C1 FSLPUIQRTFZEMT-UHFFFAOYSA-N 0.000 description 1
- LQCSQWQXNLFGKK-UHFFFAOYSA-N ethyl 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1N2C=NC=C2CCC1 LQCSQWQXNLFGKK-UHFFFAOYSA-N 0.000 description 1
- VFUWQVZUDNUXMO-UHFFFAOYSA-N ethyl 5-(4-cyanophenyl)-7,8-dihydro-6h-imidazo[1,5-a]pyridine-5-carboxylate Chemical compound C1CCC2=CN=CN2C1(C(=O)OCC)C1=CC=C(C#N)C=C1 VFUWQVZUDNUXMO-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 229950011548 fadrozole Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 230000003325 follicular Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 229940014259 gelatin Drugs 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 150000003278 haem Chemical group 0.000 description 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 208000021267 infertility disease Diseases 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- MCOGEUATPKIOMV-UHFFFAOYSA-N methyl 3-[(2,4-dichlorophenyl)methoxy]-4-(1-imidazol-1-ylbutyl)benzoate Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(=O)OC)C=C1OCC1=CC=C(Cl)C=C1Cl MCOGEUATPKIOMV-UHFFFAOYSA-N 0.000 description 1
- YSJJVZZODYJLQQ-UHFFFAOYSA-N methyl 4-(1-imidazol-1-ylbutyl)benzoate Chemical compound C1=CN=CN1C(CCC)C1=CC=C(C(=O)OC)C=C1 YSJJVZZODYJLQQ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- DAKHYLIFCYPHQW-KZQROQTASA-N minamestane Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1N DAKHYLIFCYPHQW-KZQROQTASA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- LONWTLLIALIPKY-UHFFFAOYSA-N n-[2,2-bis(4-chlorophenyl)-2-imidazol-1-ylethyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC(N1C=NC=C1)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LONWTLLIALIPKY-UHFFFAOYSA-N 0.000 description 1
- PHHKMTVZAKTCIA-UHFFFAOYSA-N n-tert-butyl-4-imidazo[1,5-a]pyridin-5-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)(C)C)=CC=C1C1=CC=CC2=CN=CN12 PHHKMTVZAKTCIA-UHFFFAOYSA-N 0.000 description 1
- ZBFVJRBOKDTSMO-UHFFFAOYSA-N naphthalene-2,6-dicarbonitrile Chemical compound C1=C(C#N)C=CC2=CC(C#N)=CC=C21 ZBFVJRBOKDTSMO-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- KPTCZURLWZSRKB-UHFFFAOYSA-N o-prop-2-enylhydroxylamine Chemical compound NOCC=C KPTCZURLWZSRKB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000002394 ovarian follicle Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical group [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000009955 peripheral mechanism Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 210000003635 pituitary gland Anatomy 0.000 description 1
- 230000003169 placental effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- JKPDEYAOCSQBSZ-OEUJLIAZSA-N plomestane Chemical compound O=C1CC[C@]2(CC#C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKPDEYAOCSQBSZ-OEUJLIAZSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/5685—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/24—Follicle-stimulating hormone [FSH]; Chorionic gonadotropins, e.g. HCG; Luteinising hormone [LH]; Thyroid-stimulating hormone [TSH]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28428201P | 2001-04-17 | 2001-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20033107A3 true CZ20033107A3 (en) | 2004-03-17 |
Family
ID=23089583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20033107A CZ20033107A3 (en) | 2001-04-17 | 2002-04-17 | Single dose aromatase inhibitor for treating infertility |
Country Status (32)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1665516A (zh) * | 2002-07-02 | 2005-09-07 | 法马西亚和厄普乔恩公司 | 使用依西美坦治疗不孕症 |
| EP1624893A2 (en) | 2003-04-01 | 2006-02-15 | Applied Research Systems ARS Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| US20100105640A1 (en) * | 2005-06-28 | 2010-04-29 | Casper Robert F | Aromatase Inhibitors for Emergency Contraception |
| CA2637000A1 (en) * | 2006-01-10 | 2007-07-19 | Diobex, Inc. | Methods and compositions for treating prostate cancer, benign prostatic hypertrophy, polycystic ovary syndrome and other conditions |
| BR112012029392A2 (pt) | 2010-05-20 | 2017-07-11 | Univ Saskatchewan | uso d einibidores de aromatase para a sincronização da ovulação, indução da superovulação ou ovulação dupla e melhora da geminação e fertilidade em um mamífero |
| US10004723B2 (en) | 2013-04-19 | 2018-06-26 | University Of Saskatchewan | Aromatase inhibitor-releasing intravaginal device |
| US20160022644A1 (en) * | 2014-07-22 | 2016-01-28 | Tsu-I Catherine Wang | Oral Transmucosal Compositions Including Aromatase Inhibitors for Treating Female Infertility |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728645A (en) * | 1982-12-21 | 1988-03-01 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives and other substituted bicyclic derivatives, useful as aromatase inhibitors |
| US4845227A (en) * | 1984-06-18 | 1989-07-04 | Eli Lilly And Company | Aromatase inhibitors from azoles |
| US4602025A (en) * | 1984-06-18 | 1986-07-22 | Eli Lilly And Company | Aromatase inhibitors |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| GB8726505D0 (en) * | 1987-11-12 | 1987-12-16 | Ici Plc | Naphtho(2 1-b)furan derivatives |
| DE4330237C2 (de) | 1993-09-02 | 1995-11-30 | Schering Ag | 1-Methylsubstituierte Androsta-1,4-dien-3,17-dione, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate |
| CA2250908C (en) * | 1996-04-30 | 2012-03-13 | Takeda Chemical Industries, Ltd. | Combined use of gnrh agonist and antagonist |
| DE19622457A1 (de) | 1996-05-24 | 1997-11-27 | Schering Ag | 7alpha-(5-Methylaminopentyl)-estratriene, Verfahren zu deren Herstellung, pharmazeutische Präparate, die diese 7alpha-(5-Methylaminopentyl)-estratriene enthalten sowie deren Verwendung zur Herstellung von Arzneimitteln |
| US6953774B2 (en) * | 2000-08-11 | 2005-10-11 | Applied Research Systems Ars Holding N.V. | Methods of inducing ovulation |
-
2002
- 2002-04-17 AU AU2002249043A patent/AU2002249043B2/en not_active Ceased
- 2002-04-17 SI SI200230747T patent/SI1383578T1/sl unknown
- 2002-04-17 NZ NZ552873A patent/NZ552873A/en not_active IP Right Cessation
- 2002-04-17 PT PT02717919T patent/PT1383578E/pt unknown
- 2002-04-17 AR ARP020101399A patent/AR034036A1/es unknown
- 2002-04-17 EE EEP200300505A patent/EE200300505A/xx unknown
- 2002-04-17 EA EA200301128A patent/EA011310B1/ru not_active IP Right Cessation
- 2002-04-17 JP JP2002581041A patent/JP2004529924A/ja active Pending
- 2002-04-17 IL IL15839602A patent/IL158396A0/xx unknown
- 2002-04-17 YU YU81203A patent/YU81203A/sh unknown
- 2002-04-17 CA CA2444980A patent/CA2444980C/en not_active Expired - Fee Related
- 2002-04-17 PL PL02366744A patent/PL366744A1/xx not_active Application Discontinuation
- 2002-04-17 KR KR10-2003-7013484A patent/KR20040025916A/ko not_active Ceased
- 2002-04-17 BR BR0208920-3A patent/BR0208920A/pt not_active IP Right Cessation
- 2002-04-17 WO PCT/CA2002/000527 patent/WO2002083241A1/en not_active Ceased
- 2002-04-17 US US10/475,101 patent/US8008333B2/en not_active Expired - Fee Related
- 2002-04-17 ES ES02717919T patent/ES2311599T3/es not_active Expired - Lifetime
- 2002-04-17 DE DE60229047T patent/DE60229047D1/de not_active Expired - Lifetime
- 2002-04-17 DK DK02717919T patent/DK1383578T3/da active
- 2002-04-17 UA UA20031110268A patent/UA82648C2/uk unknown
- 2002-04-17 MX MXPA03009447A patent/MXPA03009447A/es not_active Application Discontinuation
- 2002-04-17 HR HR20030839A patent/HRP20030839A2/hr not_active Application Discontinuation
- 2002-04-17 CZ CZ20033107A patent/CZ20033107A3/cs unknown
- 2002-04-17 SK SK1424-2003A patent/SK14242003A3/sk unknown
- 2002-04-17 EP EP02717919A patent/EP1383578B1/en not_active Expired - Lifetime
- 2002-04-17 HU HU0304003A patent/HUP0304003A2/hu unknown
- 2002-04-17 CN CNA028120825A patent/CN1551789A/zh active Pending
- 2002-04-17 AT AT02717919T patent/ATE409066T1/de active
-
2003
- 2003-09-23 NO NO20034246A patent/NO20034246L/no not_active Application Discontinuation
- 2003-09-26 ZA ZA200307516A patent/ZA200307516B/en unknown
- 2003-11-07 BG BG108323A patent/BG108323A/bg unknown
-
2008
- 2008-12-12 CY CY20081101446T patent/CY1108648T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8008333B2 (en) | Single dose aromatase inhibitor for treating infertility | |
| CA2472309C (en) | Multiple dose aromatase inhibitor for treating infertility | |
| EP1381431B1 (en) | Aromatase inhibition to enhance implantation rate | |
| US8871750B2 (en) | Use of aromatase inhibitors for endometrial thinning in preparation for surgical procedures on the endometrial cavity and uterus | |
| AU2002249043A1 (en) | Single dose aromatase inhibitor for treating infertility | |
| AU2002249041A1 (en) | Aromatase inhibition to enhance assisted reproduction | |
| US8685950B2 (en) | Use of aromatase inhibitors for treatment of ectopic pregnancy | |
| EP1759734A2 (en) | Aromatase inhibition to enhance assisted reproduction | |
| HK1067987B (en) | Aromatase inhibition to enhance assisted reproduction |