NO329543B1 - Diketopiperazinderivater, farmasoytiske sammensetninger samt anvendelser derav - Google Patents

Diketopiperazinderivater, farmasoytiske sammensetninger samt anvendelser derav Download PDF

Info

Publication number: NO329543B1
Authority: NO; Norway
Prior art keywords: group; formula; compound; pharmaceutically acceptable; alkyl
Prior art date: 2001-12-21

Application number

NO20043115A

Other languages

English (en)

Norwegian (no)

Other versions

NO20043115L (no

Inventor

Andrew Mcmurtrie Mason

Deirdre Mary Bernadette Hickey

John Liddle

Alan David Borthwick

Richard Jonathan Hatley

David George Hubert Livermore

Neil Derek Miller

Fabrizio Nerozzi

Steven Leslie Sollis

Anna Katrin Szardenings

Paul Graham Wyatt

Original Assignee

Glaxo Group Ltd

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.)

2001-12-21

Filing date

2004-07-20

Publication date

2010-11-08

2004-07-20 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2004-07-20 Publication of NO20043115L publication Critical patent/NO20043115L/no

2010-11-08 Publication of NO329543B1 publication Critical patent/NO329543B1/no

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 6
BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical class O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 78
150000003839 salts Chemical class 0.000 claims abstract description 13
-1 2-indanyl group Chemical group 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
208000005107 Premature Birth Diseases 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
206010036590 Premature baby Diseases 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
208000006399 Premature Obstetric Labor Diseases 0.000 claims 1
206010036600 Premature labour Diseases 0.000 claims 1
208000026440 premature labor Diseases 0.000 claims 1
238000000034 method Methods 0.000 abstract description 20
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 abstract description 8
101800000989 Oxytocin Proteins 0.000 abstract description 8
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 abstract description 8
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 abstract description 8
229960001723 oxytocin Drugs 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
230000001404 mediated effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 29
239000000203 mixture Substances 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000002253 acid Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
102000004279 Oxytocin receptors Human genes 0.000 description 5
108090000876 Oxytocin receptors Proteins 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
239000001267 polyvinylpyrrolidone Substances 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
KUYYTTWJIWYFTJ-WXFUMESZSA-N (2r)-2-(2,4-difluorophenyl)-2-[(2r,5r)-5-(2,3-dihydro-1h-inden-2-yl)-2-(2-methylpropyl)-3,6-dioxopiperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1([C@H](C(=O)N(C)C)N2[C@@H](C(N[C@@H](C2=O)C2CC3=CC=CC=C3C2)=O)CC(C)C)=CC=C(F)C=C1F KUYYTTWJIWYFTJ-WXFUMESZSA-N 0.000 description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
239000002775 capsule Substances 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
IUOFFQYUMLJQPJ-QGZVFWFLSA-N (2r)-2-(2,3-dihydro-1h-inden-2-yl)-2-(phenylmethoxycarbonylamino)acetic acid Chemical compound N([C@@H](C(=O)O)C1CC2=CC=CC=C2C1)C(=O)OCC1=CC=CC=C1 IUOFFQYUMLJQPJ-QGZVFWFLSA-N 0.000 description 3
XPXYLSBOXFNODG-ORJQHCMISA-N 2-(2,4-difluorophenyl)-2-[(2r,5r)-5-(2,3-dihydro-1h-inden-2-yl)-2-(2-methylpropyl)-3,6-dioxopiperazin-1-yl]-n-(2-hydroxyphenyl)acetamide Chemical compound N1([C@@H](C(N[C@@H](C1=O)C1CC2=CC=CC=C2C1)=O)CC(C)C)C(C=1C(=CC(F)=CC=1)F)C(=O)NC1=CC=CC=C1O XPXYLSBOXFNODG-ORJQHCMISA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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241000700159 Rattus Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
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239000004480 active ingredient Substances 0.000 description 3
229940024606 amino acid Drugs 0.000 description 3
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239000012267 brine Substances 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
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239000000543 intermediate Substances 0.000 description 3
229960003136 leucine Drugs 0.000 description 3
238000002414 normal-phase solid-phase extraction Methods 0.000 description 3
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125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
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- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- 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
- A61P15/06—Antiabortive agents; Labour repressants
- A—HUMAN NECESSITIES
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- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

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Chemical & Material Sciences (AREA)
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Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
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Reproductive Health (AREA)
Endocrinology (AREA)
Epidemiology (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20043115A 2001-12-21 2004-07-20 Diketopiperazinderivater, farmasoytiske sammensetninger samt anvendelser derav NO329543B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0130677.8A GB0130677D0 (en)	2001-12-21	2001-12-21	Medicaments and novel compounds
PCT/EP2002/014823 WO2003053443A1 (en)	2001-12-21	2002-12-20	Substituted diketopiperazines as oxytocin antagonists

Publications (2)

Publication Number	Publication Date
NO20043115L NO20043115L (no)	2004-07-20
NO329543B1 true NO329543B1 (no)	2010-11-08

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NO20043115A NO329543B1 (no)	2001-12-21	2004-07-20	Diketopiperazinderivater, farmasoytiske sammensetninger samt anvendelser derav

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US (3)	US7514437B2 (de)
EP (1)	EP1458393B1 (de)
JP (1)	JP4638149B2 (de)
KR (2)	KR100997856B1 (de)
CN (1)	CN100374115C (de)
AT (1)	ATE399011T1 (de)
AU (1)	AU2002364304B2 (de)
BR (1)	BRPI0215277B1 (de)
CA (1)	CA2471355C (de)
CO (1)	CO5590916A2 (de)
CY (1)	CY1108334T1 (de)
DE (1)	DE60227283D1 (de)
DK (1)	DK1458393T3 (de)
ES (1)	ES2307827T3 (de)
GB (1)	GB0130677D0 (de)
HU (1)	HU229708B1 (de)
IL (2)	IL162515A0 (de)
IS (1)	IS2613B (de)
MX (1)	MXPA04006033A (de)
NO (1)	NO329543B1 (de)
NZ (1)	NZ533218A (de)
PL (1)	PL215826B1 (de)
PT (1)	PT1458393E (de)
RU (1)	RU2303032C2 (de)
SI (1)	SI1458393T1 (de)
WO (1)	WO2003053443A1 (de)
ZA (1)	ZA200404326B (de)

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GB0314738D0 (en) *	2003-06-24	2003-07-30	Glaxo Group Ltd	Novel compounds
GB0314733D0 (en) *	2003-06-24	2003-07-30	Glaxo Group Ltd	Medicaments
GB0414093D0 (en) *	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0414092D0 (en) *	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0414100D0 (en) *	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0428235D0 (en) *	2004-12-23	2005-01-26	Glaxo Group Ltd	Novel compounds
AP2007004047A0 (en)	2005-01-20	2007-06-30	Pfizer Ltd	Substituted triazole derivatives as oxtocin antagonists
RU2318818C1 (ru) *	2006-04-12	2008-03-10	Общество С Ограниченной Ответственностью "Исследовательский Институт Химического Разнообразия"	Азагетероциклы, комбинаторная библиотека, фокусированная библиотека, фармацевтическая композиция и способ получения (варианты)
US9403789B2 (en)	2008-02-21	2016-08-02	Sequoia Pharmaceuticals, Inc.	Benzofuran-containing amino acid inhibitors of cytochrome P450
JP2012500778A (ja) *	2008-08-22	2012-01-12	ブリティッシュコロンビアキャンサーエージェンシーブランチ	アンドロゲン受容体のｎ末端の活性化の小分子阻害剤
US8716286B2 (en)	2009-10-30	2014-05-06	Glaxo Group Limited	Crystalline forms of (3R, 6R)-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl]-6-[(1S)-1-methylpropyl]-2,5-piperazinedione
SG190066A1 (en) *	2010-10-29	2013-06-28	Lonza Ag	Diketopiperazine forming dipeptidyl linker
CN103242246A (zh) *	2013-05-21	2013-08-14	苏州科捷生物医药有限公司	3-位取代的n-甲基哌嗪的合成方法
CN105061317B (zh) *	2015-08-26	2017-08-25	浙江大果生物医药科技有限公司	一类吲唑盐类化合物及其制备方法和应用
ES2915948T3 (es)	2016-01-04	2022-06-27	ObsEva SA	Administración conjunta de alfa-aminoéster de derivado de hidroxipropiltiazolidin-carboxamida y un agente tocolítico
WO2018015497A2 (en)	2016-07-21	2018-01-25	ObsEva S.A.	Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage
CN109305969B (zh) *	2017-07-27	2023-03-10	江苏恒瑞医药股份有限公司	哌嗪-2,5-二酮类衍生物、其制备方法及其在医药上的应用
CN109485598A (zh) *	2018-11-29	2019-03-19	河南师范大学	一种去除氨基上喹啉保护基的新方法
EP4025207A1 (de)	2019-09-03	2022-07-13	ObsEva S.A.	Oxytocinantagonistdosierungsschemen zur förderung der embryoimplantation und zur vorbeugung von fehlgeburt
AU2021218895A1 (en)	2020-02-10	2022-09-15	ObsEva S.A.	Biomarkers for oxytocin receptor antagonist therapy

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GB0314738D0 (en)	2003-06-24	2003-07-30	Glaxo Group Ltd	Novel compounds
GB0314733D0 (en)	2003-06-24	2003-07-30	Glaxo Group Ltd	Medicaments
GB0414100D0 (en)	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0414093D0 (en)	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0414092D0 (en)	2004-06-23	2004-07-28	Glaxo Group Ltd	Novel compounds
GB0428235D0 (en)	2004-12-23	2005-01-26	Glaxo Group Ltd	Novel compounds

2001
- 2001-12-21 GB GBGB0130677.8A patent/GB0130677D0/en not_active Ceased
2002
- 2002-12-20 PT PT02799077T patent/PT1458393E/pt unknown
- 2002-12-20 WO PCT/EP2002/014823 patent/WO2003053443A1/en not_active Ceased
- 2002-12-20 KR KR1020047009415A patent/KR100997856B1/ko not_active Expired - Fee Related
- 2002-12-20 EP EP02799077A patent/EP1458393B1/de not_active Expired - Lifetime
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- 2002-12-20 BR BRPI0215277A patent/BRPI0215277B1/pt not_active IP Right Cessation
- 2002-12-20 AU AU2002364304A patent/AU2002364304B2/en not_active Ceased
- 2002-12-20 IL IL16251502A patent/IL162515A0/xx unknown
- 2002-12-20 DE DE60227283T patent/DE60227283D1/de not_active Expired - Lifetime
- 2002-12-20 JP JP2003554200A patent/JP4638149B2/ja not_active Expired - Fee Related
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- 2002-12-20 DK DK02799077T patent/DK1458393T3/da active
- 2002-12-20 US US10/499,177 patent/US7514437B2/en not_active Expired - Fee Related
- 2002-12-20 MX MXPA04006033A patent/MXPA04006033A/es active IP Right Grant
- 2002-12-20 ES ES02799077T patent/ES2307827T3/es not_active Expired - Lifetime
- 2002-12-20 AT AT02799077T patent/ATE399011T1/de active
- 2002-12-20 KR KR1020107009110A patent/KR20100060012A/ko not_active Ceased
2004
- 2004-06-02 ZA ZA2004/04326A patent/ZA200404326B/en unknown
- 2004-06-14 IL IL162515A patent/IL162515A/en not_active IP Right Cessation
- 2004-06-16 IS IS7315A patent/IS2613B/is unknown
- 2004-06-17 CO CO04056454A patent/CO5590916A2/es active IP Right Grant
- 2004-07-20 NO NO20043115A patent/NO329543B1/no not_active IP Right Cessation
2008
- 2008-09-11 CY CY20081100980T patent/CY1108334T1/el unknown
2009
- 2009-03-27 US US12/412,837 patent/US8367673B2/en not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
WO2003053443A1 (en)	2003-07-03
CN1606443A (zh)	2005-04-13
US20050148572A1 (en)	2005-07-07
GB0130677D0 (en)	2002-02-06
BR0215277A (pt)	2004-12-14
HU229708B1 (en)	2014-05-28
PT1458393E (pt)	2008-09-29
DK1458393T3 (da)	2008-10-13
CN100374115C (zh)	2008-03-12
PL370981A1 (en)	2005-06-13
CY1108334T1 (el)	2014-02-12
ES2307827T3 (es)	2008-12-01
ZA200404326B (en)	2005-09-28
HUP0500136A2 (hu)	2005-05-30
CA2471355A1 (en)	2003-07-03
BRPI0215277B1 (pt)	2016-05-03
KR20100060012A (ko)	2010-06-04
US20130131338A1 (en)	2013-05-23
IL162515A0 (en)	2005-11-20
PL215826B1 (pl)	2014-01-31
RU2303032C2 (ru)	2007-07-20
CA2471355C (en)	2013-04-23
EP1458393A1 (de)	2004-09-22
AU2002364304B2 (en)	2008-04-17
IS7315A (is)	2004-06-16
NO20043115L (no)	2004-07-20
JP2005517663A (ja)	2005-06-16
US7514437B2 (en)	2009-04-07
JP4638149B2 (ja)	2011-02-23
DE60227283D1 (de)	2008-08-07
NZ533218A (en)	2007-01-26
IS2613B (is)	2010-04-15
CO5590916A2 (es)	2005-12-30
RU2004122392A (ru)	2005-04-20
KR100997856B1 (ko)	2010-12-01
US8541579B2 (en)	2013-09-24
KR20040065285A (ko)	2004-07-21
EP1458393B1 (de)	2008-06-25
HK1069339A1 (en)	2005-05-20
SI1458393T1 (sl)	2008-10-31
ATE399011T1 (de)	2008-07-15
US8367673B2 (en)	2013-02-05
MXPA04006033A (es)	2004-09-27
IL162515A (en)	2012-08-30
AU2002364304A1 (en)	2003-07-09
US20090186867A1 (en)	2009-07-23

Legal Events

Date	Code	Title	Description
2013-05-21	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: GLAXO GROUP LTD, GB
2018-07-23	MM1K	Lapsed by not paying the annual fees

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US8541579B2 (en)	2013-09-24	Substituted diketopiperazines as oxytocin antagonists
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AU2018302026B2 (en)	2022-04-07	TLR7/8 antagonists and uses thereof
US8937179B2 (en)	2015-01-20	Substituted diketopiperazines and their use as oxytocin antagonists
JP2018537501A (ja)	2018-12-20	多環式ｔｌｒ７／８アンタゴニスト及び免疫障害の治療におけるそれらの使用
NO338769B1 (no)	2016-10-17	Piperazindioner som oksytocinreseptorantagonister
WO2005000311A1 (en)	2005-01-06	Substituted diketopiperazines for the treatment of benign prostatic hyperplasia
RU2783748C2 (ru)	2022-11-16	Полициклические антагонисты tlr7/8 и их применение в лечении иммунных расстройств
HK1069339B (en)	2009-02-06	Substituted diketopiperazines as oxytocin antagonists