CA2611900A1 - Benzofuranone derivatives as nonsteroidal progesterone receptor modulators - Google Patents
Benzofuranone derivatives as nonsteroidal progesterone receptor modulators Download PDFInfo
- Publication number
- CA2611900A1 CA2611900A1 CA002611900A CA2611900A CA2611900A1 CA 2611900 A1 CA2611900 A1 CA 2611900A1 CA 002611900 A CA002611900 A CA 002611900A CA 2611900 A CA2611900 A CA 2611900A CA 2611900 A1 CA2611900 A1 CA 2611900A1
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- Canada
- Prior art keywords
- rac
- compounds according
- ethinyl
- alkyl
- alkenyl
- 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.)
- Abandoned
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- 239000002379 progesterone receptor modulator Substances 0.000 title abstract description 14
- 229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title abstract description 12
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
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- 210000004291 uterus Anatomy 0.000 claims abstract description 14
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- 238000000034 method Methods 0.000 claims abstract description 8
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- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 6
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- -1 methoxyphenyl Chemical group 0.000 claims description 46
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 36
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
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- 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 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 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 description 3
- YDMKKJVVAGMKRL-UHFFFAOYSA-N 5-[4-[5-(4,4,5,5,5-pentafluoropentylsulfinyl)pentoxy]phenyl]-6-phenyl-8,9-dihydro-7h-benzo[7]annulen-2-ol Chemical compound C=1C(O)=CC=C(C=2C=3C=CC(OCCCCCS(=O)CCCC(F)(F)C(F)(F)F)=CC=3)C=1CCCC=2C1=CC=CC=C1 YDMKKJVVAGMKRL-UHFFFAOYSA-N 0.000 claims description 3
- 229940122815 Aromatase inhibitor Drugs 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- PEPMWUSGRKINHX-TXTPUJOMSA-N atamestane Chemical compound C1C[C@@H]2[C@@]3(C)C(C)=CC(=O)C=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C PEPMWUSGRKINHX-TXTPUJOMSA-N 0.000 claims description 3
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- 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 description 3
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- 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 claims description 3
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- 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 description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 claims description 3
- 125000006194 pentinyl group Chemical group 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
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- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- ODYWPJIFCNWGIG-JFNPAXLGSA-N (7r,8s,9s,11s,13s,14s,17s)-11-fluoro-13-methyl-7-[5-[methyl(7,7,8,8,9,9,10,10,10-nonafluorodecyl)amino]pentyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound F[C@H]1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2[C@H](CCCCCN(CCCCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C)CC3=CC(O)=CC=C3[C@H]21 ODYWPJIFCNWGIG-JFNPAXLGSA-N 0.000 claims 2
- CNMFCEIWLPSHPT-JFNPAXLGSA-N (7r,8s,9s,11s,13s,14s,17s)-11-fluoro-13-methyl-7-[5-[methyl-[3-(4,4,5,5,5-pentafluoropentylsulfanyl)propyl]amino]pentyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound F[C@H]1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2[C@H](CCCCCN(C)CCCSCCCC(F)(F)C(F)(F)F)CC3=CC(O)=CC=C3[C@H]21 CNMFCEIWLPSHPT-JFNPAXLGSA-N 0.000 claims 2
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- 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 description 32
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- 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 1
- 230000003054 hormonal effect Effects 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000004797 ketoamides Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229950001701 lilopristone Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 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 1
- 229950011093 onapristone Drugs 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 238000009094 second-line therapy Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GBZCUMOLXVTYSD-UHFFFAOYSA-N tert-butyl-dimethyl-(2-methylbut-3-yn-2-yloxy)silane Chemical compound CC(C)(C)[Si](C)(C)OC(C)(C)C#C GBZCUMOLXVTYSD-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Reproductive Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005030294.7 | 2005-06-24 | ||
| DE102005030294A DE102005030294A1 (de) | 2005-06-24 | 2005-06-24 | Nichtsteroidale Progesteronrezeptor-Modulatoren |
| PCT/EP2006/006532 WO2006136462A1 (de) | 2005-06-24 | 2006-06-22 | Nonsteroidal progesterone receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2611900A1 true CA2611900A1 (en) | 2006-12-28 |
Family
ID=36716643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002611900A Abandoned CA2611900A1 (en) | 2005-06-24 | 2006-06-22 | Benzofuranone derivatives as nonsteroidal progesterone receptor modulators |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1899315A1 (de) |
| JP (1) | JP2008543911A (de) |
| KR (1) | KR20080018275A (de) |
| CN (1) | CN101248056A (de) |
| AR (1) | AR057409A1 (de) |
| AU (1) | AU2006261049A1 (de) |
| BR (1) | BRPI0612305A2 (de) |
| CA (1) | CA2611900A1 (de) |
| CR (1) | CR9595A (de) |
| DE (1) | DE102005030294A1 (de) |
| DO (1) | DOP2006000150A (de) |
| EA (1) | EA200702604A1 (de) |
| EC (1) | ECSP078043A (de) |
| GT (1) | GT200600272A (de) |
| IL (1) | IL188022A0 (de) |
| MX (1) | MX2008000070A (de) |
| NO (1) | NO20080441L (de) |
| PE (1) | PE20070170A1 (de) |
| TW (1) | TW200738665A (de) |
| UY (1) | UY29626A1 (de) |
| WO (1) | WO2006136462A1 (de) |
| ZA (1) | ZA200800689B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY30805A1 (es) * | 2006-12-21 | 2008-07-31 | Bayer Schering Pharma Ag | Moduladores no esteroides de receptores de progesterona |
| DE102007032800A1 (de) * | 2007-07-10 | 2009-01-15 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
| DE102007058747A1 (de) | 2007-12-05 | 2009-06-10 | Bayer Schering Pharma Aktiengesellschaft | Nichtsteroidale Progesteronrezeptor-Modulatoren |
| TWI477276B (zh) * | 2008-04-28 | 2015-03-21 | Repros Therapeutics Inc | 抗黃體素給藥方案 |
| CA2872644A1 (en) | 2012-05-31 | 2013-12-05 | Repros Therapeutics Inc. | Formulations and methods for vaginal delivery of antiprogestins |
| JP6343619B2 (ja) | 2012-11-02 | 2018-06-13 | レプロス セラピューティクス インコーポレイティド | プロゲステロン依存性病態を処置する方法およびその組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19723722A1 (de) * | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| EP1175422A2 (de) * | 1999-05-04 | 2002-01-30 | Ligand Pharmaceuticals Incorporated | Tetracyclische progesteronrezeptor-modulator-verbindungen und verfahren |
| US6358948B1 (en) * | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| US6960581B2 (en) * | 2002-01-14 | 2005-11-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations, and uses thereof |
| BR0308394A (pt) * | 2002-03-11 | 2005-01-25 | Schering Ag | 5-{2-hidróxi-3-[1-(3-trifluormetilfenil)-ciclopropil]-pr oprionilamino}-ftaleto e compostos relacionados com atividade moduladora de receptores de progesterona para uso em controle da fertilidade e terapia de reposição hormonal |
| DE10346939A1 (de) * | 2003-10-06 | 2005-05-19 | Schering Ag | Heterocyclisch substituierte Pentanole, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
-
2005
- 2005-06-24 DE DE102005030294A patent/DE102005030294A1/de not_active Ceased
-
2006
- 2006-06-22 AU AU2006261049A patent/AU2006261049A1/en not_active Abandoned
- 2006-06-22 BR BRPI0612305-8A patent/BRPI0612305A2/pt not_active Application Discontinuation
- 2006-06-22 EA EA200702604A patent/EA200702604A1/ru unknown
- 2006-06-22 KR KR1020087001789A patent/KR20080018275A/ko not_active Application Discontinuation
- 2006-06-22 CA CA002611900A patent/CA2611900A1/en not_active Abandoned
- 2006-06-22 CN CNA2006800306699A patent/CN101248056A/zh active Pending
- 2006-06-22 JP JP2008517445A patent/JP2008543911A/ja active Pending
- 2006-06-22 EP EP06762405A patent/EP1899315A1/de not_active Withdrawn
- 2006-06-22 MX MX2008000070A patent/MX2008000070A/es not_active Application Discontinuation
- 2006-06-22 WO PCT/EP2006/006532 patent/WO2006136462A1/de active Application Filing
- 2006-06-23 TW TW095122741A patent/TW200738665A/zh unknown
- 2006-06-26 DO DO2006000150A patent/DOP2006000150A/es unknown
- 2006-06-26 UY UY29626A patent/UY29626A1/es not_active Application Discontinuation
- 2006-06-26 PE PE2006000732A patent/PE20070170A1/es not_active Application Discontinuation
- 2006-06-26 GT GT200600272A patent/GT200600272A/es unknown
- 2006-06-27 AR ARP060102752A patent/AR057409A1/es unknown
-
2007
- 2007-12-10 IL IL188022A patent/IL188022A0/en unknown
- 2007-12-14 CR CR9595A patent/CR9595A/es not_active Application Discontinuation
- 2007-12-21 EC EC2007008043A patent/ECSP078043A/es unknown
-
2008
- 2008-01-23 ZA ZA200800689A patent/ZA200800689B/xx unknown
- 2008-01-23 NO NO20080441A patent/NO20080441L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EA200702604A1 (ru) | 2008-06-30 |
| KR20080018275A (ko) | 2008-02-27 |
| CN101248056A (zh) | 2008-08-20 |
| GT200600272A (es) | 2007-08-20 |
| WO2006136462A1 (de) | 2006-12-28 |
| MX2008000070A (es) | 2008-03-19 |
| CR9595A (es) | 2008-05-05 |
| ECSP078043A (es) | 2008-01-23 |
| UY29626A1 (es) | 2007-01-31 |
| TW200738665A (en) | 2007-10-16 |
| EP1899315A1 (de) | 2008-03-19 |
| NO20080441L (no) | 2008-03-07 |
| DOP2006000150A (es) | 2006-12-31 |
| IL188022A0 (en) | 2008-03-20 |
| JP2008543911A (ja) | 2008-12-04 |
| BRPI0612305A2 (pt) | 2010-11-03 |
| DE102005030294A1 (de) | 2007-01-04 |
| AU2006261049A1 (en) | 2006-12-28 |
| PE20070170A1 (es) | 2007-03-02 |
| ZA200800689B (en) | 2009-07-29 |
| AR057409A1 (es) | 2007-12-05 |
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