NO315044B1 - Nye dihydronaftalenderivater - Google Patents

Nye dihydronaftalenderivater Download PDF

Info

Publication number: NO315044B1
Authority: NO; Norway
Prior art keywords: compound; preparation; prepared; methyl; methoxy
Prior art date: 1997-10-02

Application number

NO20001289A

Other languages

English (en)

Norwegian (no)

Other versions

NO20001289L (no

NO20001289D0 (no

Inventor

Rolf Wolfgang Hartmann

Yoshikazu Ikeda

Shin Nomoto

Bertil Wachall

Makoto Yoshihama

Masamichi Nakakoshi

Original Assignee

Daiichi Seiyaku Co

Priority date (The priority date 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 date listed.)

1997-10-02

Filing date

2000-03-10

Publication date

2003-06-30

2000-03-10 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

2000-03-10 Publication of NO20001289L publication Critical patent/NO20001289L/no

2000-03-10 Publication of NO20001289D0 publication Critical patent/NO20001289D0/no

2003-06-30 Publication of NO315044B1 publication Critical patent/NO315044B1/no

Links

KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 title claims abstract description 12
230000002401 inhibitory effect Effects 0.000 claims abstract description 25
230000015572 biosynthetic process Effects 0.000 claims abstract description 11
102000014654 Aromatase Human genes 0.000 claims abstract description 10
108010078554 Aromatase Proteins 0.000 claims abstract description 10
238000003786 synthesis reaction Methods 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 6
230000000694 effects Effects 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 claims description 4
WGHPDURJIDESAL-UHFFFAOYSA-N 5-methyl-6-(pyridin-4-ylmethyl)-7,8-dihydronaphthalen-2-ol Chemical group C1CC2=CC(O)=CC=C2C(C)=C1CC1=CC=NC=C1 WGHPDURJIDESAL-UHFFFAOYSA-N 0.000 claims description 3
APLDUEGPXBUKMY-UHFFFAOYSA-N 8-methyl-7-(pyridin-4-ylmethyl)-5,6-dihydronaphthalen-2-ol Chemical group C1CC2=CC=C(O)C=C2C(C)=C1CC1=CC=NC=C1 APLDUEGPXBUKMY-UHFFFAOYSA-N 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
239000003163 gonadal steroid hormone Substances 0.000 abstract description 18
206010060862 Prostate cancer Diseases 0.000 abstract description 6
208000000236 Prostatic Neoplasms Diseases 0.000 abstract description 6
102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 abstract description 6
108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 abstract description 6
201000010099 disease Diseases 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
206010051482 Prostatomegaly Diseases 0.000 abstract description 5
206010047486 Virilism Diseases 0.000 abstract description 5
206010006187 Breast cancer Diseases 0.000 abstract description 4
208000026310 Breast neoplasm Diseases 0.000 abstract description 4
206010033128 Ovarian cancer Diseases 0.000 abstract description 4
206010061535 Ovarian neoplasm Diseases 0.000 abstract description 4
208000030270 breast disease Diseases 0.000 abstract description 4
231100000794 masculinization Toxicity 0.000 abstract description 4
206010002383 Angina Pectoris Diseases 0.000 abstract description 3
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208000006673 asthma Diseases 0.000 abstract description 3
230000001419 dependent effect Effects 0.000 abstract description 3
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208000010125 myocardial infarction Diseases 0.000 abstract description 3
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229940124597 therapeutic agent Drugs 0.000 abstract description 3
208000002495 Uterine Neoplasms Diseases 0.000 abstract 1
206010046766 uterine cancer Diseases 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 258
238000002360 preparation method Methods 0.000 description 199
238000000034 method Methods 0.000 description 101
238000004519 manufacturing process Methods 0.000 description 81
239000013078 crystal Substances 0.000 description 75
238000002844 melting Methods 0.000 description 72
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238000005160 1H NMR spectroscopy Methods 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
238000000921 elemental analysis Methods 0.000 description 29
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
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239000000725 suspension Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000000843 powder Substances 0.000 description 17
238000012360 testing method Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
102000004190 Enzymes Human genes 0.000 description 12
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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 12
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 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
108010010803 Gelatin Proteins 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
239000008273 gelatin Substances 0.000 description 10
229920000159 gelatin Polymers 0.000 description 10
235000019322 gelatine Nutrition 0.000 description 10
235000011852 gelatine desserts Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
239000007787 solid Substances 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
239000011777 magnesium Substances 0.000 description 8
229910052749 magnesium Inorganic materials 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000000758 substrate Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 7
210000001589 microsome Anatomy 0.000 description 7
239000001856 Ethyl cellulose Substances 0.000 description 6
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 6
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000001768 carboxy methyl cellulose Substances 0.000 description 6
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239000005457 ice water Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 6
239000000186 progesterone Substances 0.000 description 6
229960003387 progesterone Drugs 0.000 description 6
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 6
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
230000018044 dehydration Effects 0.000 description 5
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230000005764 inhibitory process Effects 0.000 description 5
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BRCPWISABURVIH-UHFFFAOYSA-N 5-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=C1C=CC=C2OC BRCPWISABURVIH-UHFFFAOYSA-N 0.000 description 4
MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 description 4
GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
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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 4
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239000003086 colorant Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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235000019325 ethyl cellulose Nutrition 0.000 description 4
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229940088597 hormone Drugs 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000005259 measurement Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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238000000746 purification Methods 0.000 description 4
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
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239000008107 starch Substances 0.000 description 4
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210000001550 testis Anatomy 0.000 description 4
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
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239000000556 agonist Substances 0.000 description 3
239000008280 blood Substances 0.000 description 3
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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YXYZOZUTGYAILQ-UHFFFAOYSA-N 3-[(1-methyl-3,4-dihydronaphthalen-2-yl)methyl]pyridine Chemical compound C1CC2=CC=CC=C2C(C)=C1CC1=CC=CN=C1 YXYZOZUTGYAILQ-UHFFFAOYSA-N 0.000 description 2
WYUOXSJEMFHGQO-UHFFFAOYSA-N 3-[(5-methoxy-1-methyl-3,4-dihydronaphthalen-2-yl)methyl]pyridine Chemical compound C1CC=2C(OC)=CC=CC=2C(C)=C1CC1=CC=CN=C1 WYUOXSJEMFHGQO-UHFFFAOYSA-N 0.000 description 2
GDVHFTJQMRJPOY-UHFFFAOYSA-N 3-[(6-methoxy-1-methyl-3,4-dihydronaphthalen-2-yl)methyl]pyridine Chemical compound C1CC2=CC(OC)=CC=C2C(C)=C1CC1=CC=CN=C1 GDVHFTJQMRJPOY-UHFFFAOYSA-N 0.000 description 2
BYUUDXWTDQHHKB-UHFFFAOYSA-N 3-[(7-methoxy-1-methyl-3,4-dihydronaphthalen-2-yl)methyl]pyridine Chemical compound CC=1C2=CC(OC)=CC=C2CCC=1CC1=CC=CN=C1 BYUUDXWTDQHHKB-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)

NO20001289A 1997-10-02 2000-03-10 Nye dihydronaftalenderivater NO315044B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP28426397		1997-10-02
PCT/JP1998/004426 WO1999018075A1 (fr)	1997-10-02	1998-10-01	Nouveaux composes a base de dihydronaphtalene et leur procede de production

Publications (3)

Publication Number	Publication Date
NO20001289L NO20001289L (no)	2000-03-10
NO20001289D0 NO20001289D0 (no)	2000-03-10
NO315044B1 true NO315044B1 (no)	2003-06-30

Family

ID=17676271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20001289A NO315044B1 (no)	1997-10-02	2000-03-10	Nye dihydronaftalenderivater

Country Status (17)

Country	Link
EP (1)	EP1028110B1 (zh)
KR (1)	KR20000069426A (zh)
CN (1)	CN1117732C (zh)
AT (1)	ATE264304T1 (zh)
AU (1)	AU743405B2 (zh)
CA (1)	CA2298527A1 (zh)
DE (1)	DE69823222T2 (zh)
DK (1)	DK1028110T3 (zh)
ES (1)	ES2218853T3 (zh)
FI (1)	FI20000207A (zh)
HU (1)	HUP0004037A3 (zh)
IL (1)	IL133483A0 (zh)
NO (1)	NO315044B1 (zh)
NZ (1)	NZ501822A (zh)
RU (1)	RU2203890C2 (zh)
WO (1)	WO1999018075A1 (zh)
ZA (1)	ZA988954B (zh)

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KR100287366B1 (ko)	1997-11-24	2001-04-16	윤순조	엠피이지 방식을 이용한 휴대용 음향 재생장치 및 방법
US7001926B2 (en)	2000-03-10	2006-02-21	Oxigene, Inc.	Tubulin binding agents and corresponding prodrug constructs
TWI283669B (en) *	1999-06-10	2007-07-11	Allergan Inc	Compounds and method of treatment having agonist-like activity selective at alpha 2B or 2B/2C adrenergic receptors
US6849656B1 (en)	1999-09-17	2005-02-01	Baylor University	Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents
JP4616454B2 (ja) *	1999-10-22	2011-01-19	武田薬品工業株式会社	１−置換フェニル−１−（１ｈ−イミダゾール−４−イル）アルコール類、その製造法および用途
DE60027034T2 (de)	1999-10-22	2006-11-09	Takeda Pharmaceutical Co. Ltd.	1-substituierte-phenyl-1-(1h-imidazol-4-yl)alkohole, verfahren zu deren herstellung sowie deren verwendung
JP4520012B2 (ja) *	1999-10-22	2010-08-04	武田薬品工業株式会社	１−置換−１−（１ｈ−イミダゾール−４−イル）メタノール類
JP2004505888A (ja)	2000-03-10	2004-02-26	ベイラー・ユニバーシテイ	チューブリン結合リガンドおよび対応するプロドラッグ構造
US7091240B2 (en)	2000-03-10	2006-08-15	Oxigene, Inc.	Tubulin binding ligands and corresponding prodrug constructs
MY134929A (en)	2000-11-17	2008-01-31	Takeda Pharmaceutical	Novel imidazole derivatives, production method thereof and use thereof
ATE502030T1 (de)	2000-11-20	2011-04-15	Takeda Pharmaceutical	Imidazolderivate, verfahren zu deren herstellung und deren verwendung
DE60139639D1 (de)	2000-12-08	2009-10-01	Takeda Pharmaceutical	Substituierte thiazolderivate mit 3-pyridylgruppen, verfahren zu deren herstellung und deren verwendung
WO2004073602A2 (en) *	2002-01-25	2004-09-02	Pharmacia Corporation	Aldosterone blocker therapy to prevent or treat inflammation-related disorders
US7456214B2 (en)	2004-05-03	2008-11-25	Baylor University	Chromene-containing compounds with anti-tubulin and vascular targeting activity
UA105794C2 (uk)	2009-06-26	2014-06-25	Новартіс Аг	1,3-ДИЗАМІЩЕНІ ПОХІДНІ ІМІДАЗОЛІДИН-2-ОНУ ЯК ІНГІБІТОРИ Cyp17
WO2012018948A2 (en)	2010-08-04	2012-02-09	Pellficure Pharmaceuticals, Inc.	Novel treatment of prostate carcinoma
JP2013537210A (ja)	2010-09-16	2013-09-30	ノバルティスアーゲー	１７α−ヒドロキシラーゼ／Ｃ１７，２０−リアーゼ阻害剤
JP6002210B2 (ja)	2011-04-28	2016-10-05	ノバルティスアーゲー	１７α−ヒドロキシラーゼ／Ｃ１７，２０−リアーゼ阻害剤
EP2968219B1 (en)	2013-03-14	2019-04-24	Pellficure Pharmaceuticals, Inc.	Novel therapy for prostate carcinoma
US10093620B2 (en)	2014-09-12	2018-10-09	Pellficure Pharmaceuticals, Inc.	Compositions and methods for treatment of prostate carcinoma
AU2017350690A1 (en)	2016-10-24	2019-06-13	Pellficure Pharmaceuticals Inc.	Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione

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JPS5681566A (en) *	1979-12-05	1981-07-03	Yoshitomi Pharmaceut Ind Ltd	Imidazole derivative
ZA825413B (en) *	1981-08-26	1983-06-29	Pfizer	Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
US4540705A (en) *	1983-03-14	1985-09-10	Sterling Drug Inc.	Antidepressant imidazolines and related compounds
PH22076A (en) *	1983-08-25	1988-05-20	Daiichi Seiyaku Co	Benzocycloalkane derivative
JPS61186348A (ja) *	1985-02-14	1986-08-20	Dai Ichi Seiyaku Co Ltd	ナフタレン誘導体
DE3508905A1 (de) *	1985-03-13	1986-09-18	Hoechst Ag, 6230 Frankfurt	Neue imidazolylverbindungen und verfahren zu ihrer herstellung
JPH06166674A (ja) *	1992-12-01	1994-06-14	Tokyo Tanabe Co Ltd	テトラリン化合物
JP3338905B2 (ja) *	1993-05-13	2002-10-28	帝国臓器製薬株式会社	６位置換ステロイド誘導体
HUT75871A (en) *	1993-09-30	1997-05-28	Yamanouchi Co	Azole derivatives and pharmaceutical compositions thereof
FR2787451B1 (fr) *	1998-12-18	2001-01-26	Adir	Nouveaux composes imidazoliniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

1998
- 1998-10-01 ES ES98945556T patent/ES2218853T3/es not_active Expired - Lifetime
- 1998-10-01 WO PCT/JP1998/004426 patent/WO1999018075A1/ja active Search and Examination
- 1998-10-01 DE DE69823222T patent/DE69823222T2/de not_active Expired - Fee Related
- 1998-10-01 AT AT98945556T patent/ATE264304T1/de not_active IP Right Cessation
- 1998-10-01 EP EP98945556A patent/EP1028110B1/en not_active Expired - Lifetime
- 1998-10-01 ZA ZA988954A patent/ZA988954B/xx unknown
- 1998-10-01 NZ NZ501822A patent/NZ501822A/en unknown
- 1998-10-01 RU RU99127323/04A patent/RU2203890C2/ru not_active IP Right Cessation
- 1998-10-01 CA CA002298527A patent/CA2298527A1/en not_active Abandoned
- 1998-10-01 IL IL13348398A patent/IL133483A0/xx unknown
- 1998-10-01 DK DK98945556T patent/DK1028110T3/da active
- 1998-10-01 KR KR1019997005209A patent/KR20000069426A/ko not_active Application Discontinuation
- 1998-10-01 AU AU92810/98A patent/AU743405B2/en not_active Ceased
- 1998-10-01 CN CN98808436A patent/CN1117732C/zh not_active Expired - Fee Related
- 1998-10-01 HU HU0004037A patent/HUP0004037A3/hu unknown
2000
- 2000-02-01 FI FI20000207A patent/FI20000207A/fi not_active Application Discontinuation
- 2000-03-10 NO NO20001289A patent/NO315044B1/no unknown

Also Published As

Publication number	Publication date
DE69823222D1 (de)	2004-05-19
HUP0004037A3 (en)	2002-03-28
EP1028110A1 (en)	2000-08-16
FI20000207A (fi)	2000-02-01
NZ501822A (en)	2001-12-21
AU9281098A (en)	1999-04-27
ATE264304T1 (de)	2004-04-15
CN1268120A (zh)	2000-09-27
CN1117732C (zh)	2003-08-13
ZA988954B (en)	1999-04-12
DE69823222T2 (de)	2005-04-14
CA2298527A1 (en)	1999-04-15
WO1999018075A1 (fr)	1999-04-15
NO20001289L (no)	2000-03-10
NO20001289D0 (no)	2000-03-10
HUP0004037A2 (hu)	2001-10-28
EP1028110A4 (en)	2001-05-23
DK1028110T3 (da)	2004-07-19
ES2218853T3 (es)	2004-11-16
KR20000069426A (ko)	2000-11-25
IL133483A0 (en)	2001-04-30
EP1028110B1 (en)	2004-04-14
RU2203890C2 (ru)	2003-05-10
AU743405B2 (en)	2002-01-24

Publication	Publication Date	Title
NO315044B1 (no)	2003-06-30	Nye dihydronaftalenderivater
US7514068B2 (en)	2009-04-07	Biphenyl-pyrazolecarboxamide compounds
DE69626862T2 (de)	2003-12-24	Imidazolderivate mit alpha2-rezeptor aktivität
TWI404712B (zh)	2013-08-11	作為用於增加ＨＤＬ-Ｃ，低ＬＤＬ-Ｃ及低膽固醇之ＰＰＡＲ-德它（δ）作用劑的苯并氮雜-氧基-乙酸衍生物
WO2007121687A1 (fr)	2007-11-01	Dérivés du 4-méthyl-1h-diaryl pyrazole et leur utilisation comme médicaments
SK151287A3 (en)	1998-06-03	Process for producing tolunitriles substituted by a heterocyclic residue
HUT60720A (en)	1992-10-28	Process for producing bis-arylamide and urea derivatives hindering thromocyte activating factor, as well as pharmaceutical compositions comprising such compounds
AU2001294592A1 (en)	2002-04-02	Compounds and methods for modulation of estrogen receptors
EP3124480B1 (en)	2018-07-11	Amide compound
JP2022540421A (ja)	2022-09-15	エストロゲン受容体アンタゴニストのレジメン
EP0135177B1 (en)	1989-12-06	Benzocycloalkane derivatives
US4999355A (en)	1991-03-12	Isoindolinone derivatives, processes for preparing them and medicines containing them
JPH06511239A (ja)	1994-12-15	ヘテロアルコキシベンズアゼピン類
US20090258902A1 (en)	2009-10-15	Biphenyl-pyrazolecarboxamide compounds
Hartmann et al.	1995	Pyridyl-substituted tetrahydrocyclopropa [a] naphthalenes: highly active and selective inhibitors of P450 arom
CN101014573A (zh)	2007-08-08	5－ht7受体拮抗剂
US5045548A (en)	1991-09-03	Quinolyl methoxy compounds and their use as antiasthmatic agents
JPS6320226B2 (zh)	1988-04-26
JP2017518378A (ja)	2017-07-06	小分子ｌｆａ−１阻害薬
US6559157B2 (en)	2003-05-06	Dihydronaphthalene compounds
DE69422629T2 (de)	2000-06-29	Indolderivate als 5-alpha-reductase-1 inhibitoren
MXPA00003167A (en)	2001-12-13	Novel dihydronaphthalene compounds and process for producing the same
JPH032168A (ja)	1991-01-08	アロマターゼ阻害活性を有する新規な４（５）―イミダゾール
WO1994007866A1 (en)	1994-04-14	Aromatase inhibitor
EP1676840A1 (en)	2006-07-05	5-HT7 Receptor antagonists