ES2636248T3 - Derivados de pirimidina pirido- o pirrolo-fusionados como inhibidores de autotaxina para el tratamiento del dolor - Google Patents
Derivados de pirimidina pirido- o pirrolo-fusionados como inhibidores de autotaxina para el tratamiento del dolor Download PDFInfo
- Publication number
- ES2636248T3 ES2636248T3 ES14702336.0T ES14702336T ES2636248T3 ES 2636248 T3 ES2636248 T3 ES 2636248T3 ES 14702336 T ES14702336 T ES 14702336T ES 2636248 T3 ES2636248 T3 ES 2636248T3
- Authority
- ES
- Spain
- Prior art keywords
- mmol
- dihydro
- equiv
- pyrimidin
- ylamino
- 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.)
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- 102100021977 Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Human genes 0.000 title description 33
- 108050004000 Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Proteins 0.000 title description 33
- 239000003112 inhibitor Substances 0.000 title description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- -1 2,3-dihydro-1H-inden-2-ylamino Chemical group 0.000 claims description 114
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- ILOFWCAZDNILKY-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]-2-[2-(2h-triazol-4-yl)ethoxy]ethanone Chemical compound C1C2=CN=C(NC3CC4=CC=CC=C4C3)N=C2CN1C(=O)COCCC1=CNN=N1 ILOFWCAZDNILKY-UHFFFAOYSA-N 0.000 claims description 3
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- 235000019198 oils Nutrition 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
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- 238000000034 method Methods 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
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- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 239000002211 L-ascorbic acid Substances 0.000 description 10
- 235000000069 L-ascorbic acid Nutrition 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 229960005070 ascorbic acid Drugs 0.000 description 10
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 10
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- 229940098773 bovine serum albumin Drugs 0.000 description 1
- XSBPYGDBXQXSCU-UHFFFAOYSA-N but-3-yn-1-amine Chemical compound NCCC#C XSBPYGDBXQXSCU-UHFFFAOYSA-N 0.000 description 1
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 1
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- LJQOTKFLOZZVML-UHFFFAOYSA-N chloryl chlorate Chemical compound O=[Cl](=O)O[Cl](=O)=O LJQOTKFLOZZVML-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 239000011536 extraction buffer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- HNWWAWKDVFVJRG-UHFFFAOYSA-N hydron;6-hydroxy-1h-pyridin-2-one;chloride Chemical compound Cl.OC1=CC=CC(=O)N1 HNWWAWKDVFVJRG-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QAFBDRSXXHEXGB-UHFFFAOYSA-N imidazol-1-ylacetic acid Chemical compound OC(=O)CN1C=CN=C1 QAFBDRSXXHEXGB-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- IKOMUVKGGBXEKG-UHFFFAOYSA-N methyl 4-(3-benzyltriazol-4-yl)oxybutanoate Chemical compound COC(=O)CCCOC1=CN=NN1CC1=CC=CC=C1 IKOMUVKGGBXEKG-UHFFFAOYSA-N 0.000 description 1
- QAWFLJGZSZIZHO-UHFFFAOYSA-N methyl 4-bromobutanoate Chemical compound COC(=O)CCCBr QAWFLJGZSZIZHO-UHFFFAOYSA-N 0.000 description 1
- RAVVJKCSZXAIQP-UHFFFAOYSA-N methyl 5-bromopentanoate Chemical compound COC(=O)CCCCBr RAVVJKCSZXAIQP-UHFFFAOYSA-N 0.000 description 1
- FLUGZEGZYQCCTQ-UHFFFAOYSA-N methyl 5-cyanopentanoate Chemical compound COC(=O)CCCCC#N FLUGZEGZYQCCTQ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RESRVDFIMBPWDM-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine Chemical compound C1NCCC2=NC(NC3CC4=CC=CC=C4C3)=NC=C21 RESRVDFIMBPWDM-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- DBZSBXFQTNEHIA-UHFFFAOYSA-N tert-butyl 2-(2,3-dihydro-1h-inden-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1C2=CC=CC=C2CC1NC1=NC=C2CN(C(=O)OC(C)(C)C)CC2=N1 DBZSBXFQTNEHIA-UHFFFAOYSA-N 0.000 description 1
- VZOQZQKRMKARBR-UHFFFAOYSA-N tert-butyl 2-(2,3-dihydro-1h-inden-2-ylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C1C2=CC=CC=C2CC1NC1=NC=C(CN(C(=O)OC(C)(C)C)CC2)C2=N1 VZOQZQKRMKARBR-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- MTBKGWHHOBJMHJ-UHFFFAOYSA-N tert-butyl imidazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CN=C1 MTBKGWHHOBJMHJ-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (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)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361751363P | 2013-01-11 | 2013-01-11 | |
| US201361751363P | 2013-01-11 | ||
| US201361777201P | 2013-03-12 | 2013-03-12 | |
| US201361777201P | 2013-03-12 | ||
| PCT/US2014/010400 WO2014110000A1 (en) | 2013-01-11 | 2014-01-07 | Pyrido- or pyrrolo-fused pyrimidine derivatives as autotaxin inhibitors for treating pain |
Publications (1)
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|---|---|
| ES2636248T3 true ES2636248T3 (es) | 2017-10-05 |
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| ES14702336.0T Active ES2636248T3 (es) | 2013-01-11 | 2014-01-07 | Derivados de pirimidina pirido- o pirrolo-fusionados como inhibidores de autotaxina para el tratamiento del dolor |
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|---|---|
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| EP (1) | EP2943494B1 (enExample) |
| JP (1) | JP6285461B2 (enExample) |
| KR (1) | KR101757997B1 (enExample) |
| CN (1) | CN104903327B (enExample) |
| AU (1) | AU2014205642B2 (enExample) |
| BR (1) | BR112015015812A2 (enExample) |
| CA (1) | CA2893253C (enExample) |
| EA (1) | EA025106B1 (enExample) |
| ES (1) | ES2636248T3 (enExample) |
| MX (1) | MX2015008971A (enExample) |
| TW (1) | TWI499591B (enExample) |
| WO (1) | WO2014110000A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201500356A (zh) * | 2013-04-12 | 2015-01-01 | Lilly Co Eli | 二氫吡啶并嘧啶化合物 |
| PE20160654A1 (es) | 2013-11-22 | 2016-07-15 | Pharmakea Inc | Compuestos de inhibidor de autotaxina |
| US9051320B1 (en) | 2014-08-18 | 2015-06-09 | Pharmakea, Inc. | Methods for the treatment of metabolic disorders by a selective small molecule autotaxin inhibitor |
| GB201501870D0 (en) | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
| GB201502020D0 (en) | 2015-02-06 | 2015-03-25 | Cancer Rec Tech Ltd | Autotaxin inhibitory compounds |
| CN116059203A (zh) | 2015-05-27 | 2023-05-05 | 赛博治疗有限责任公司 | 自分泌运动因子抑制剂及其用途 |
| US10118904B2 (en) | 2015-06-05 | 2018-11-06 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of Demyelinating Diseases |
| WO2018106643A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Heterocyclic azoles for the treatment of demyelinating diseases |
| WO2018106646A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Aminotriazoles for the treatment of demyelinating diseases |
| WO2018106641A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Pyrazoles for the treatment of demyelinating diseases |
| KR101798840B1 (ko) | 2017-05-17 | 2017-11-17 | 주식회사 레고켐 바이오사이언스 | 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물 |
| US10961242B2 (en) | 2017-05-17 | 2021-03-30 | Legochem Biosciences, Inc. | Compounds as autotaxin inhibitors and pharmaceutical compositions comprising the same |
| JP7274767B2 (ja) * | 2018-05-24 | 2023-05-17 | ▲広▼州市恒▲諾▼康医▲薬▼科技有限公司 | 芳香族複素環式化合物及びその医薬組成物 |
| US20220081400A1 (en) * | 2018-07-16 | 2022-03-17 | The Scripps Research Institute | Opioid haptens, conjugates, vaccines, and methods of generating antibodies |
| KR102629358B1 (ko) * | 2019-02-01 | 2024-01-24 | 우한 휴먼웰 이노베이티브 드러그 리서치 앤드 디벨롭먼트 센터 리미티드 컴퍼니 | 피롤로피리미딘 유도체 및 그의 용도 |
| CA3149062A1 (en) * | 2019-09-06 | 2021-03-11 | Xuejun Zhang | Pyrimidine compound and preparation method therefor |
| CA3150700A1 (en) * | 2019-09-17 | 2021-03-25 | Renato T. Skerlj | IMIDAZOLE SUBSTITUTE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| WO2021088957A1 (zh) * | 2019-11-07 | 2021-05-14 | 广州市恒诺康医药科技有限公司 | 芳杂环化合物、其药物组合物及其应用 |
| US20230069174A1 (en) * | 2019-12-11 | 2023-03-02 | Sichuan Haisco Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic autotaxin inhibitor, and composition containing same and use thereof |
| CN113943296B (zh) * | 2020-07-16 | 2025-07-04 | 武汉人福创新药物研发中心有限公司 | 吡咯并嘧啶衍生物及其应用 |
| CN113943295B (zh) * | 2020-07-16 | 2025-08-12 | 武汉人福创新药物研发中心有限公司 | 吡咯并嘧啶类化合物及其用途 |
| TWI894325B (zh) * | 2020-07-28 | 2025-08-21 | 大陸商武漢人福創新藥物研發中心有限公司 | 含氮雜環化合物的鹽及其鹽的固體形式、藥物組合物和用途 |
| CN113999235B (zh) * | 2020-07-28 | 2025-06-10 | 武汉人福创新药物研发中心有限公司 | 含氮杂环化合物的固体形式及其药物组合物和用途 |
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|---|---|---|---|---|
| SV2002000205A (es) | 1999-11-01 | 2002-06-07 | Lilly Co Eli | Compuestos farmaceuticos ref. x-01095 |
| AU2003242252A1 (en) | 2002-06-07 | 2003-12-22 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| DE102004020908A1 (de) | 2004-04-28 | 2005-11-17 | Grünenthal GmbH | Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen |
| JP5198256B2 (ja) * | 2005-05-04 | 2013-05-15 | エボテク エージー | 縮合複素環式化合物、並びにそれらの組成物及び使用 |
| US8530650B2 (en) * | 2008-12-01 | 2013-09-10 | Merck Patent Gmbh | 2, 5-diamino-substituted pyrido [4, 3-D] pyrimidines as autotaxin inhibitors against cancer |
| WO2012009258A2 (en) * | 2010-07-13 | 2012-01-19 | Edward Roberts | Peptidomimetic galanin receptor modulators |
| EP2606031B1 (en) * | 2010-08-20 | 2017-09-27 | Amira Pharmaceuticals, Inc. | Autotaxin inhibitors and uses thereof |
| AR084515A1 (es) * | 2010-12-22 | 2013-05-22 | Merz Pharma Gmbh & Co Kgaa | Derivados heterociclicos nitrogenados, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de enfermedades asociadas al sistema nervioso central tales como parkinson y alzheimer, entre otras |
| WO2013054185A1 (en) * | 2011-10-13 | 2013-04-18 | Pfizer, Inc. | Pyrimidine and pyridine derivatives useful in therapy |
| EP3243815B1 (en) * | 2011-10-28 | 2019-07-10 | Inhibitaxin Limited | Pyridazine derivatives useful in therapy |
| TW201520219A (zh) * | 2013-03-12 | 2015-06-01 | Lilly Co Eli | 咪唑並吡啶化合物 |
| TW201500356A (zh) * | 2013-04-12 | 2015-01-01 | Lilly Co Eli | 二氫吡啶并嘧啶化合物 |
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2013
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- 2014-01-07 EA EA201591098A patent/EA025106B1/ru not_active IP Right Cessation
- 2014-01-07 KR KR1020157018295A patent/KR101757997B1/ko not_active Expired - Fee Related
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- 2014-01-07 BR BR112015015812A patent/BR112015015812A2/pt not_active IP Right Cessation
- 2014-01-07 US US14/148,775 patent/US8969555B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA2893253C (en) | 2017-11-28 |
| KR101757997B1 (ko) | 2017-07-13 |
| AU2014205642B2 (en) | 2016-02-25 |
| AU2014205642A1 (en) | 2015-07-02 |
| JP6285461B2 (ja) | 2018-02-28 |
| BR112015015812A2 (pt) | 2017-07-11 |
| TWI499591B (zh) | 2015-09-11 |
| EA025106B1 (ru) | 2016-11-30 |
| US8969555B2 (en) | 2015-03-03 |
| TW201437209A (zh) | 2014-10-01 |
| EP2943494A1 (en) | 2015-11-18 |
| CN104903327B (zh) | 2016-09-07 |
| EA201591098A1 (ru) | 2015-11-30 |
| CN104903327A (zh) | 2015-09-09 |
| EP2943494B1 (en) | 2017-02-22 |
| JP2016505010A (ja) | 2016-02-18 |
| CA2893253A1 (en) | 2014-07-17 |
| US20140200231A1 (en) | 2014-07-17 |
| KR20150092761A (ko) | 2015-08-13 |
| WO2014110000A1 (en) | 2014-07-17 |
| MX2015008971A (es) | 2015-09-28 |
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