JP2005516924A5 - - Google Patents
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- Publication number
- JP2005516924A5 JP2005516924A5 JP2003552277A JP2003552277A JP2005516924A5 JP 2005516924 A5 JP2005516924 A5 JP 2005516924A5 JP 2003552277 A JP2003552277 A JP 2003552277A JP 2003552277 A JP2003552277 A JP 2003552277A JP 2005516924 A5 JP2005516924 A5 JP 2005516924A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- host
- cyclopentyloxy
- methoxyphenyl
- pharmaceutical composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003112 inhibitor Substances 0.000 claims description 9
- WUADCCWRTIWANL-UHFFFAOYSA-N biochanin A Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O WUADCCWRTIWANL-UHFFFAOYSA-N 0.000 claims description 4
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 4
- 235000007240 daidzein Nutrition 0.000 claims description 2
- 229940045109 genistein Drugs 0.000 claims description 2
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims description 2
- 235000006539 genistein Nutrition 0.000 claims description 2
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims description 2
- 239000000186 progesterone Substances 0.000 claims description 2
- -1 allofylline Chemical compound 0.000 claims 19
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 230000016087 ovulation Effects 0.000 claims 9
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 8
- 102000001708 Protein Isoforms Human genes 0.000 claims 8
- 108010029485 Protein Isoforms Proteins 0.000 claims 8
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 8
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 8
- 230000029849 luteinization Effects 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 230000027758 ovulation cycle Effects 0.000 claims 5
- 230000001939 inductive effect Effects 0.000 claims 4
- RRRUXBQSQLKHEL-UHFFFAOYSA-N piclamilast Chemical compound COC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OC1CCCC1 RRRUXBQSQLKHEL-UHFFFAOYSA-N 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 3
- AXDZQZQUNHYUGL-UHFFFAOYSA-N 1-butyl-3-propyl-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCC)C2=C1NC=N2 AXDZQZQUNHYUGL-UHFFFAOYSA-N 0.000 claims 2
- IPUJXWMHZRFSAT-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-(2-methylphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C(=CC=CC=2)C)C(=O)C2=C1C(CC)=NN2C1CCCC1 IPUJXWMHZRFSAT-UHFFFAOYSA-N 0.000 claims 2
- IOSAAWHGJUZBOG-UHFFFAOYSA-N 3-(6-amino-9h-purin-9-yl)nonan-2-ol Chemical compound N1=CN=C2N(C(C(C)O)CCCCCC)C=NC2=C1N IOSAAWHGJUZBOG-UHFFFAOYSA-N 0.000 claims 2
- MNHXYNNKDDXKNP-UHFFFAOYSA-N 4-(3-chlorophenyl)-1,7-diethyl-2-pyrido[2,3-d]pyrimidinone Chemical compound N=1C(=O)N(CC)C2=NC(CC)=CC=C2C=1C1=CC=CC(Cl)=C1 MNHXYNNKDDXKNP-UHFFFAOYSA-N 0.000 claims 2
- UTUUPXBCDMQYRR-HSZRJFAPSA-N 4-[(2r)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine Chemical compound COC1=CC=C([C@H](CC=2C=CN=CC=2)C=2C=CC=CC=2)C=C1OC1CCCC1 UTUUPXBCDMQYRR-HSZRJFAPSA-N 0.000 claims 2
- YPFYVOZSQYRRTM-UHFFFAOYSA-N 4-[4-methoxy-3-(5-phenylpentoxy)phenyl]-2-methylbenzoic acid Chemical compound COC1=CC=C(C=2C=C(C)C(C(O)=O)=CC=2)C=C1OCCCCCC1=CC=CC=C1 YPFYVOZSQYRRTM-UHFFFAOYSA-N 0.000 claims 2
- PDUXMHXBBXXJFQ-UHFFFAOYSA-N 5,6-diethoxy-1-benzothiophene-2-carboxylic acid Chemical compound C1=C(OCC)C(OCC)=CC2=C1SC(C(O)=O)=C2 PDUXMHXBBXXJFQ-UHFFFAOYSA-N 0.000 claims 2
- VPDKLXXECPQWMY-UHFFFAOYSA-N 5-phenyl-3-(pyridin-3-ylmethyl)imidazo[4,5-c][1,8]naphthyridin-4-one Chemical compound C12=NC=CC=C2C=2N=CN(CC=3C=NC=CC=3)C=2C(=O)N1C1=CC=CC=C1 VPDKLXXECPQWMY-UHFFFAOYSA-N 0.000 claims 2
- 102000011022 Chorionic Gonadotropin Human genes 0.000 claims 2
- 108010062540 Chorionic Gonadotropin Proteins 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- GHBUMWHHZFGRDI-AWEZNQCLSA-N [(3s)-1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-3-yl]methanol Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3C[C@@H](CO)N=2)=C1 GHBUMWHHZFGRDI-AWEZNQCLSA-N 0.000 claims 2
- PJRYVTGCPZXGEY-UHFFFAOYSA-N ac1l53vz Chemical compound O=C1N(CCC)C2=CC=C(OC)N=C2N2C1=C(C)N=C2CC PJRYVTGCPZXGEY-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229940015047 chorionic gonadotropin Drugs 0.000 claims 2
- PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 claims 2
- DVWBMWJOYIFITF-UHFFFAOYSA-N n'-hydroxy-5,6-dimethoxy-1-benzothiophene-2-carboximidamide;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC2=C1SC(C(\N)=N\O)=C2 DVWBMWJOYIFITF-UHFFFAOYSA-N 0.000 claims 2
- BWJFLHODOYZAML-GODXOYSCSA-N n-[4-[(4ar,10bs)-8,9-dimethoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]phenyl]acetamide;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O.N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OC)=C1C1=CC=C(NC(C)=O)C=C1 BWJFLHODOYZAML-GODXOYSCSA-N 0.000 claims 2
- 230000000624 ovulatory effect Effects 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- JBTJXXDPSJKBRV-IBGZPJMESA-N (3s)-3-(3-cyclopentyloxy-4-methoxyphenyl)-2-methyl-5-oxo-n-(pyridin-3-ylmethyl)pyrazolidine-1-carboxamide Chemical compound COC1=CC=C([C@H]2N(N(C(=O)C2)C(=O)NCC=2C=NC=CC=2)C)C=C1OC1CCCC1 JBTJXXDPSJKBRV-IBGZPJMESA-N 0.000 claims 1
- GMQNXISAYIRAFJ-UHFFFAOYSA-N 1-(3-nitrophenyl)-3-(pyridin-3-ylmethyl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(CC=3C=NC=CC=3)C(=O)C3=CC=CN=C32)=O)=C1 GMQNXISAYIRAFJ-UHFFFAOYSA-N 0.000 claims 1
- QUUJQFQTLSFCKW-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-ylmethylamino)-6-chloroquinazolin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC(NCC=2C=C3OCOC3=CC=2)=C(C=C(Cl)C=C2)C2=N1 QUUJQFQTLSFCKW-UHFFFAOYSA-N 0.000 claims 1
- PQTJTRTXCNZDFT-UHFFFAOYSA-N 2-(2-propoxyphenyl)-3,7-dihydropurin-6-one Chemical compound CCCOC1=CC=CC=C1C(N1)=NC(=O)C2=C1N=CN2 PQTJTRTXCNZDFT-UHFFFAOYSA-N 0.000 claims 1
- LWFPGLPUKPULLC-UHFFFAOYSA-N 2-[4-[6,7-diethoxy-2,3-bis(hydroxymethyl)naphthalen-1-yl]pyridin-3-yl]-4-pyridin-3-ylphthalazin-1-one Chemical compound C=12C=C(OCC)C(OCC)=CC2=CC(CO)=C(CO)C=1C1=CC=NC=C1N(C(C1=CC=CC=C11)=O)N=C1C1=CC=CN=C1 LWFPGLPUKPULLC-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QRHLIWLOPSLNCU-UHFFFAOYSA-N 2h-phthalazin-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NN=CC2=C1 QRHLIWLOPSLNCU-UHFFFAOYSA-N 0.000 claims 1
- APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 claims 1
- DDYUBCCTNHWSQM-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound COC1=CC=C(C(CC(N)=O)N2C(C3=CC=CC=C3C2=O)=O)C=C1OC1CCCC1 DDYUBCCTNHWSQM-UHFFFAOYSA-N 0.000 claims 1
- CGFRGBQJWVFTRF-UHFFFAOYSA-N 3-[(3-cyclopentyloxy-4-methoxyphenyl)methyl]-n-ethyl-8-propan-2-ylpurin-6-amine Chemical compound C12=NC(C(C)C)=NC2=C(NCC)N=CN1CC(C=1)=CC=C(OC)C=1OC1CCCC1 CGFRGBQJWVFTRF-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- MIXLZCYFMQNQDD-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-N'-hydroxy-1,3-thiazole-2-carboximidamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(C(N)=NO)=N1 MIXLZCYFMQNQDD-UHFFFAOYSA-N 0.000 claims 1
- YAAACGHPCYZCKO-UHFFFAOYSA-N 4-(3-bromophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2-one Chemical compound N=1C(=O)N(CC)C2=NC(CC)=CC=C2C=1C1=CC=CC(Br)=C1 YAAACGHPCYZCKO-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- PDMUULPVBYQBBK-UHFFFAOYSA-N 4-[(3-butoxy-4-methoxyphenyl)methyl]-2-imidazolidinone Chemical compound C1=C(OC)C(OCCCC)=CC(CC2NC(=O)NC2)=C1 PDMUULPVBYQBBK-UHFFFAOYSA-N 0.000 claims 1
- CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 claims 1
- LWDKMRYLWLWQBL-UHFFFAOYSA-N 4-fluoro-n'-hydroxy-5,6-dimethoxy-1-benzothiophene-2-carboximidamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.FC1=C(OC)C(OC)=CC2=C1C=C(C(=N)NO)S2 LWDKMRYLWLWQBL-UHFFFAOYSA-N 0.000 claims 1
- POJMHKGLNMKGTN-UHFFFAOYSA-N 5-(3-cyclopentyloxy-4-methoxyphenyl)pyridine-2-carboxamide Chemical compound COC1=CC=C(C=2C=NC(=CC=2)C(N)=O)C=C1OC1CCCC1 POJMHKGLNMKGTN-UHFFFAOYSA-N 0.000 claims 1
- PCCPERGCFKIYIS-UHFFFAOYSA-N 5-(4-methoxy-3-propoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OCCC)=CC(C2(C)OC(=O)NC2)=C1 PCCPERGCFKIYIS-UHFFFAOYSA-N 0.000 claims 1
- DUPLFHKYPXLEPQ-UHFFFAOYSA-N 6-(3-cyclopentyloxy-4-methoxyphenyl)-8,9-dimethyl-3-oxa-1-azaspiro[4.5]dec-8-en-2-one Chemical compound COC1=CC=C(C2C3(NC(=O)OC3)CC(C)=C(C)C2)C=C1OC1CCCC1 DUPLFHKYPXLEPQ-UHFFFAOYSA-N 0.000 claims 1
- DHLCTHXZKHGREA-UHFFFAOYSA-N 6h-pyrido[2,3-d]pyridazin-5-one Chemical compound C1=CC=C2C(=O)NN=CC2=N1 DHLCTHXZKHGREA-UHFFFAOYSA-N 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims 1
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 claims 1
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 claims 1
- ZJVFLBOZORBYFE-UHFFFAOYSA-N Ibudilast Chemical compound C1=CC=CC2=C(C(=O)C(C)C)C(C(C)C)=NN21 ZJVFLBOZORBYFE-UHFFFAOYSA-N 0.000 claims 1
- 102000009151 Luteinizing Hormone Human genes 0.000 claims 1
- 108010073521 Luteinizing Hormone Proteins 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- RUOGJYKOQBFJIG-UHFFFAOYSA-N SCH-351591 Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)NC1=C(Cl)C=[N+]([O-])C=C1Cl RUOGJYKOQBFJIG-UHFFFAOYSA-N 0.000 claims 1
- DDNCQMVWWZOMLN-IRLDBZIGSA-N Vinpocetine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-IRLDBZIGSA-N 0.000 claims 1
- YPFLFUJKZDAXRA-UHFFFAOYSA-N [3-(carbamoylamino)-2-(2,4-dichlorobenzoyl)-1-benzofuran-6-yl] methanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C)=CC=C2C(NC(N)=O)=C1C(=O)C1=CC=C(Cl)C=C1Cl YPFLFUJKZDAXRA-UHFFFAOYSA-N 0.000 claims 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 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 1
- 229960002932 anastrozole Drugs 0.000 claims 1
- 230000002513 anti-ovulatory effect Effects 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 claims 1
- 229950001653 cilomilast Drugs 0.000 claims 1
- 229960003608 clomifene Drugs 0.000 claims 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- HWXIGFIVGWUZAO-UHFFFAOYSA-N doxofylline Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CC1OCCO1 HWXIGFIVGWUZAO-UHFFFAOYSA-N 0.000 claims 1
- 229960004483 doxofylline Drugs 0.000 claims 1
- 229950004203 droloxifene Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- ZJKNESGOIKRXQY-UHFFFAOYSA-N enoximone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=C(C)NC(=O)N1 ZJKNESGOIKRXQY-UHFFFAOYSA-N 0.000 claims 1
- 229950011548 fadrozole Drugs 0.000 claims 1
- 230000004720 fertilization Effects 0.000 claims 1
- STTRYQAGHGJXJJ-LICLKQGHSA-N filaminast Chemical compound COC1=CC=C(C(\C)=N\OC(N)=O)C=C1OC1CCCC1 STTRYQAGHGJXJJ-LICLKQGHSA-N 0.000 claims 1
- 229950006884 filaminast Drugs 0.000 claims 1
- 229940028334 follicle stimulating hormone Drugs 0.000 claims 1
- 230000008217 follicular development Effects 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229960002491 ibudilast Drugs 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 238000011419 induction treatment Methods 0.000 claims 1
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 claims 1
- 229960003881 letrozole Drugs 0.000 claims 1
- 229940040129 luteinizing hormone Drugs 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229960003574 milrinone Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YUPDAIOGPWAFEG-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxy-2,3-dihydroindol-3-yl]-2-oxoacetamide Chemical compound C1C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 YUPDAIOGPWAFEG-UHFFFAOYSA-N 0.000 claims 1
- DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 claims 1
- GEJPLNWGEJLXJN-UHFFFAOYSA-N n-benzyl-6-chloro-2-piperazin-1-yl-4-pyrrolidin-1-ylpteridin-7-amine Chemical compound ClC1=NC2=C(N3CCCC3)N=C(N3CCNCC3)N=C2N=C1NCC1=CC=CC=C1 GEJPLNWGEJLXJN-UHFFFAOYSA-N 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 210000000287 oocyte Anatomy 0.000 claims 1
- 230000011599 ovarian follicle development Effects 0.000 claims 1
- 229950005184 piclamilast Drugs 0.000 claims 1
- 229960003387 progesterone Drugs 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims 1
- 229960004622 raloxifene Drugs 0.000 claims 1
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| US6861422B2 (en) * | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| JP2006522151A (ja) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
| CA2552540A1 (en) * | 2004-01-17 | 2005-07-28 | Boehringer Ingelheim International Gmbh | Use of substituted pteridines for the treatment of diseases of the respiratory tract |
| DE102004002557A1 (de) * | 2004-01-17 | 2005-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von substituierten Pyrimido(5,4-d)pyrimidinen zur Behandlung von Atemwegserkrankungen |
| DE102004029784A1 (de) * | 2004-06-21 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-Benzylaminodihydropteridinone, Verfahren zur deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004033670A1 (de) * | 2004-07-09 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel |
| US20060035903A1 (en) * | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
| US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
| US7759485B2 (en) * | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
| US7728134B2 (en) * | 2004-08-14 | 2010-06-01 | Boehringer Ingelheim International Gmbh | Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament |
| US20060074088A1 (en) * | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
| EP1630163A1 (de) * | 2004-08-25 | 2006-03-01 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| EP1632493A1 (de) * | 2004-08-25 | 2006-03-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | Dihydropteridinonderivative, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004058337A1 (de) * | 2004-12-02 | 2006-06-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten |
| EP1915155A1 (en) * | 2005-08-03 | 2008-04-30 | Boehringer Ingelheim International GmbH | Dihydropteridinones in the treatment of respiratory diseases |
| US7439358B2 (en) | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
| EP2185559A1 (en) * | 2007-08-03 | 2010-05-19 | Boehringer Ingelheim International GmbH | Crystalline form of a dihydropteridione derivative |
| US8546566B2 (en) | 2010-10-12 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Process for manufacturing dihydropteridinones and intermediates thereof |
| US9358233B2 (en) | 2010-11-29 | 2016-06-07 | Boehringer Ingelheim International Gmbh | Method for treating acute myeloid leukemia |
| US9370535B2 (en) | 2011-05-17 | 2016-06-21 | Boehringer Ingelheim International Gmbh | Method for treatment of advanced solid tumors |
| CN103169699B (zh) * | 2011-12-22 | 2014-11-12 | 中国农业大学 | 来曲唑在用于制备成年牛超数排卵药物中的应用 |
| WO2014089913A1 (zh) * | 2012-12-12 | 2014-06-19 | 山东亨利医药科技有限责任公司 | 作为酪氨酸激酶抑制剂的并环化合物 |
| US20150031699A1 (en) | 2013-07-26 | 2015-01-29 | Boehringer Ingelheim International Gmbh | Treatment of myelodysplastic syndrome |
| US9867831B2 (en) | 2014-10-01 | 2018-01-16 | Boehringer Ingelheim International Gmbh | Combination treatment of acute myeloid leukemia and myelodysplastic syndrome |
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| US5087615A (en) | 1989-03-17 | 1992-02-11 | Applied Research Systems Ars Holding N.V. | Novel method of ovulation induction in humans |
| US5710170A (en) | 1995-12-15 | 1998-01-20 | Merck Frosst Canada, Inc. | Tri-aryl ethane derivatives as PDE IV inhibitors |
| GB9603723D0 (en) | 1996-02-22 | 1996-04-24 | Merck & Co Inc | Diphenyl pyridyl derivatives as pde iv inhibitors |
| AP1147A (en) | 1996-05-03 | 2003-02-25 | Pfizer | Substituted indazole derivatives and related compounds. |
| HUP0100042A3 (en) | 1996-05-20 | 2003-01-28 | Darwin Discovery Ltd Cambridge | Benzofuran carboxamides medicaments containing the same and their therapeutic use |
| IL126557A (en) | 1996-05-20 | 2002-09-12 | Darwin Discovery Ltd | Quinoline (thio) carboxamides inhibiting TNF or PDE-IV and pharmaceutical preparations containing them |
| JP2000510866A (ja) | 1996-05-20 | 2000-08-22 | ダーウィン・ディスカバリー・リミテッド | Ｔｎｆとｐｄｅ―ｉｖのインヒビターとしてのキノリンスルホンアミド |
| WO1997048697A1 (en) | 1996-06-19 | 1997-12-24 | Rhone-Poulenc Rorer Limited | Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase |
| SK176598A3 (en) | 1996-06-25 | 2000-06-12 | Pfizer | Indazole derivatives, pharmaceutical composition on their base and methods of treatment |
| GB9614718D0 (en) | 1996-07-12 | 1996-09-04 | Bayer Ag | 3-ureido-pyridofurans and -pyridothiophenes |
| DE69720757T2 (de) | 1996-10-02 | 2004-03-04 | Janssen Pharmaceutica N.V. | Pde-iv hemmende 2-cyanoiminoimidazol-derivate |
| GB9622386D0 (en) | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| WO1998020007A1 (en) | 1996-11-06 | 1998-05-14 | Darwin Discovery Limited | Quinolines and their therapeutic use |
| JP3237109B2 (ja) * | 1996-12-13 | 2001-12-10 | 田辺製薬株式会社 | 医薬組成物 |
| US6472425B1 (en) * | 1997-10-31 | 2002-10-29 | Nitromed, Inc. | Methods for treating female sexual dysfunctions |
| AU752415B2 (en) * | 1998-04-23 | 2002-09-19 | Zentaris Ivf Gmbh | Method for the treatment of fertility disorders |
| KR20010043828A (ko) * | 1998-05-26 | 2001-05-25 | 에바-마리아 시마-메이어, 얼설라 멜져, 마거, 하르트만 | ｃＡＭＰ-증강 화합물 단독 또는 감수분열-자극 화합물하나 이상과의 조합에 의한 불임 치료 방법 |
| EP1086096B1 (de) | 1998-06-10 | 2003-07-23 | ALTANA Pharma AG | Benzamide mit tetrahydrofuranyloxy-substituenten als inhibitoren der phosphodiesterase 4 |
| US6316472B1 (en) | 1999-05-13 | 2001-11-13 | Merck Frosst Canada & Co. | Heterosubstituted pyridine derivatives as PDE 4 inhibitors |
| SI1212089T1 (sl) * | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Sinergisticna kombinacija roflumilasta in salmeterola |
| US6258833B1 (en) * | 1999-12-23 | 2001-07-10 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| WO2001079526A2 (en) * | 2000-04-17 | 2001-10-25 | Bioimage A/S | Live cell procedures to identify compounds modulating intracellular distribution of phosphodiesterase (pde) enzymes |
| WO2001087287A2 (en) * | 2000-05-19 | 2001-11-22 | Applied Research Systems Ars Holding N.V. | Use of pyrazole derivatives for treating infertility |
| ATE332708T1 (de) * | 2000-06-06 | 2006-08-15 | Glaxo Group Ltd | Krebsbehandlung zusammensetzung, welche ein antineoplastisches mittel und pde4 inhibitor enthält |
| US6953774B2 (en) * | 2000-08-11 | 2005-10-11 | Applied Research Systems Ars Holding N.V. | Methods of inducing ovulation |
| US20020065324A1 (en) * | 2000-08-11 | 2002-05-30 | Stephen Palmer | Methods of inducing ovulation |
| JP2006522151A (ja) * | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
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2001
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- 2001-12-14 JP JP2003552277A patent/JP4532115B2/ja not_active Expired - Fee Related
- 2001-12-14 KR KR10-2004-7009259A patent/KR20040075004A/ko not_active Ceased
- 2001-12-14 AU AU2002217111A patent/AU2002217111B2/en not_active Ceased
- 2001-12-14 EP EP01274987A patent/EP1463493B1/en not_active Expired - Lifetime
- 2001-12-14 KR KR1020097000508A patent/KR101056916B1/ko not_active Expired - Fee Related
- 2001-12-14 IL IL16250601A patent/IL162506A0/xx unknown
- 2001-12-14 BR BRPI0117198-4A patent/BRPI0117198B1/pt unknown
- 2001-12-14 WO PCT/EP2001/014730 patent/WO2003051344A1/en not_active Ceased
- 2001-12-14 CN CNA01823951XA patent/CN1582146A/zh active Pending
- 2001-12-14 US US10/498,639 patent/US7507707B2/en not_active Expired - Fee Related
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- 2001-12-14 AT AT07018904T patent/ATE526013T1/de active
- 2001-12-14 MX MXPA04005782A patent/MXPA04005782A/es active IP Right Grant
- 2001-12-14 PT PT01274987T patent/PT1463493E/pt unknown
- 2001-12-14 EA EA200400808A patent/EA011213B1/ru not_active IP Right Cessation
- 2001-12-14 AT AT01274987T patent/ATE374606T1/de active
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- 2001-12-14 DK DK07018904.8T patent/DK1908463T3/da active
- 2001-12-14 PT PT07018904T patent/PT1908463E/pt unknown
- 2001-12-14 UA UA20040705737A patent/UA80418C2/uk unknown
- 2001-12-14 DE DE60130813T patent/DE60130813T2/de not_active Expired - Lifetime
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