NO313413B1 - Hydrokinonderivat, anvendelse derav og farmasöytisk preparat - Google Patents

Hydrokinonderivat, anvendelse derav og farmasöytisk preparat Download PDF

Info

Publication number: NO313413B1
Authority: NO; Norway
Prior art keywords: group; pyrimidinedione; methyl; amino; hydroxy
Prior art date: 1996-09-19

Application number

NO19974313A

Other languages

English (en)

Norwegian (no)

Other versions

NO974313D0 (no

NO974313L (no

Inventor

Yoshiaki Isobe

Yuso Goto

Masanori Tobe

Osamu Takahashi

Original Assignee

Japan Energy Corp

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.)

1996-09-19

Filing date

1997-09-18

Publication date

2002-09-30

1997-09-18 Application filed by Japan Energy Corp filed Critical Japan Energy Corp

1997-09-18 Publication of NO974313D0 publication Critical patent/NO974313D0/no

1998-03-20 Publication of NO974313L publication Critical patent/NO974313L/no

2002-09-30 Publication of NO313413B1 publication Critical patent/NO313413B1/no

Links

125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 53
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
208000026935 allergic disease Diseases 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
-1 methoxybenzoyl Chemical group 0.000 description 78
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 30
238000000034 method Methods 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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239000002674 ointment Substances 0.000 description 7
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
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VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical group C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
229940124597 therapeutic agent Drugs 0.000 description 5
HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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239000011780 sodium chloride Substances 0.000 description 4
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RLNWRDKVJSXXPP-UHFFFAOYSA-N tert-butyl 2-[(2-bromoanilino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNC1=CC=CC=C1Br RLNWRDKVJSXXPP-UHFFFAOYSA-N 0.000 description 3
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125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical class NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 description 2
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 2
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VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
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PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
108010036949 Cyclosporine Proteins 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000037374 absorbed through the skin Effects 0.000 description 2
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150000001412 amines Chemical class 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
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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 2
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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230000037444 atrophy Effects 0.000 description 1
PCCNIENXBRUYFK-UHFFFAOYSA-O azanium;cerium(4+);pentanitrate Chemical compound [NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PCCNIENXBRUYFK-UHFFFAOYSA-O 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000003074 decanoyl 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(*)=O 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
231100000001 growth retardation Toxicity 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
239000008101 lactose Substances 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
FJLBFSROUSIWMA-UHFFFAOYSA-N metyrapone Chemical compound C=1C=CN=CC=1C(C)(C)C(=O)C1=CC=CN=C1 FJLBFSROUSIWMA-UHFFFAOYSA-N 0.000 description 1
229960004465 metyrapone Drugs 0.000 description 1
125000001419 myristoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ALYNUARCKBRTJM-UHFFFAOYSA-N n-butyl-n-(2,4-dioxo-1h-pyrimidin-5-yl)-3,4-dihydro-2h-chromene-2-carboxamide Chemical compound C1CC2=CC=CC=C2OC1C(=O)N(CCCC)C1=CNC(=O)NC1=O ALYNUARCKBRTJM-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000008512 pyrimidinediones Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])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])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
150000003890 succinate salts Chemical class 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
229960000984 tocofersolan Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000936 topical exposure Toxicity 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
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (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)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19974313A 1996-09-19 1997-09-18 Hydrokinonderivat, anvendelse derav og farmasöytisk preparat NO313413B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP24827296		1996-09-19

Publications (3)

Publication Number	Publication Date
NO974313D0 NO974313D0 (no)	1997-09-18
NO974313L NO974313L (no)	1998-03-20
NO313413B1 true NO313413B1 (no)	2002-09-30

Family

ID=17175664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19974313A NO313413B1 (no)	1996-09-19	1997-09-18	Hydrokinonderivat, anvendelse derav og farmasöytisk preparat

Country Status (13)

Country	Link
US (2)	US5821247A (de)
EP (1)	EP0831092B1 (de)
AT (1)	ATE194838T1 (de)
AU (1)	AU716992B2 (de)
CA (1)	CA2216288C (de)
DE (1)	DE69702580T2 (de)
DK (1)	DK0831092T3 (de)
ES (1)	ES2149548T3 (de)
GR (1)	GR3034418T3 (de)
NO (1)	NO313413B1 (de)
NZ (1)	NZ328769A (de)
PT (1)	PT831092E (de)
ZA (1)	ZA978413B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6649629B2 (en) *	1999-12-23	2003-11-18	Nitromed, Inc.	Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use
JPWO2004026842A1 (ja) *	2002-09-20	2006-01-12	住友製薬株式会社	新規ウラシル誘導体及びその医薬用途
EP3018122B1 (de) *	2007-11-06	2018-10-10	BioElectron Technology Corporation	4-(p-quinonyl)-2-hydroxybutanamid-derivate zur behandlung von mitochondrialen erkrankungen
WO2016100579A1 (en)	2014-12-16	2016-06-23	Edison Pharmaceuticals, Inc.,	Polymorphic and amorphous forms of (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
ES3033538T3 (en) *	2015-10-08	2025-08-05	Khondrion Ip B V	Novel compounds for treating mitochondrial disease

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5661153A (en) *	1994-07-19	1997-08-26	Japan Energy Corporation	1-arylpyrimidine derivatives and pharmaceutical use thereof

1997
- 1997-09-16 AU AU37601/97A patent/AU716992B2/en not_active Ceased
- 1997-09-16 US US08/933,208 patent/US5821247A/en not_active Expired - Fee Related
- 1997-09-17 AT AT97250280T patent/ATE194838T1/de not_active IP Right Cessation
- 1997-09-17 DK DK97250280T patent/DK0831092T3/da active
- 1997-09-17 DE DE69702580T patent/DE69702580T2/de not_active Expired - Fee Related
- 1997-09-17 ES ES97250280T patent/ES2149548T3/es not_active Expired - Lifetime
- 1997-09-17 PT PT97250280T patent/PT831092E/pt unknown
- 1997-09-17 EP EP97250280A patent/EP0831092B1/de not_active Expired - Lifetime
- 1997-09-18 NZ NZ328769A patent/NZ328769A/en unknown
- 1997-09-18 ZA ZA9708413A patent/ZA978413B/xx unknown
- 1997-09-18 NO NO19974313A patent/NO313413B1/no unknown
- 1997-09-19 CA CA002216288A patent/CA2216288C/en not_active Expired - Fee Related
1998
- 1998-07-10 US US09/113,826 patent/US5877318A/en not_active Expired - Fee Related
2000
- 2000-09-18 GR GR20000402106T patent/GR3034418T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK0831092T3 (da)	2000-10-16
CA2216288A1 (en)	1998-03-19
EP0831092B1 (de)	2000-07-19
US5877318A (en)	1999-03-02
DE69702580D1 (de)	2000-08-24
EP0831092A3 (de)	1998-04-08
NZ328769A (en)	1998-07-28
US5821247A (en)	1998-10-13
AU716992B2 (en)	2000-03-16
GR3034418T3 (en)	2000-12-29
CA2216288C (en)	2006-02-07
ZA978413B (en)	1998-03-26
NO974313D0 (no)	1997-09-18
ATE194838T1 (de)	2000-08-15
NO974313L (no)	1998-03-20
EP0831092A2 (de)	1998-03-25
PT831092E (pt)	2000-10-31
AU3760197A (en)	1998-03-26
DE69702580T2 (de)	2001-03-08
ES2149548T3 (es)	2000-11-01

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EP0930310B1 (de)	2003-03-26	Isocumarinderivate und deren verwendung in medikamenten
EP0629602B1 (de)	1997-09-10	3,4-Dihydroxychalkonderivate
EP0389370B1 (de)	1994-04-27	19-Nor, 3-keto-Steroide mit einer amino-substituierten Kette, Verfahren zu deren Herstellung, Zwischenprodukte und pharmazeutische Präparate davon
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CA2214744C (en)	2002-12-24	3-(bis-substituted phenylmethylene)oxindole derivatives
WO2000050408A1 (en)	2000-08-31	Pyridazin-3-one derivatives and medicines containing the same
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EP0720983B1 (de)	2001-03-14	Diphenyl-disulfid Verbindungen
JPH0291074A (ja)	1990-03-30	置換された５，６，７，８‐テトラヒドロイミダゾ［１，５‐ａ］ピリジン及びその製造方法
JPS60158150A (ja)	1985-08-19	１，４‐ナフトキノン誘導体類
JP2876144B2 (ja)	1999-03-31	３―フェニルクマリン―７―イルオキシ酢酸誘導体とその製法及び用途
US20080234357A1 (en)	2008-09-25	Indole derivatives substituted with long-chain alcohols and medicaments containing them
US6046218A (en)	2000-04-04	Pyridine derivative and medicament containing the same as an effective ingredient
EP0418655B1 (de)	1995-04-19	Konjugierte gamma-Hydroxybutenolid-Derivate und sie als aktiver Wirkstoff enthaltende Mittel gegen Magengeschwüre
JP2010254614A (ja)	2010-11-11	含セレン複素環化合物及びその用途
JP2984403B2 (ja)	1999-11-29	イソキノロン誘導体
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EP1541562A1 (de)	2005-06-15	Neue uracilderivate und deren medizinische verwendung
JPH07188209A (ja)	1995-07-25	３−フェニルチオクロモン化合物及びアルドースレダクターゼ阻害剤
JP2009051731A (ja)	2009-03-12	新規アスコクロリン誘導体化合物及びそれを含有する医薬組成物