CN111484493A - 1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途 - Google Patents

1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途 Download PDF

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Publication number: CN111484493A
Authority: CN; China
Prior art keywords: pyrrolo; pyrazole; mmol; pyridin; benzyl
Prior art date: 2012-01-30
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.): Pending

Application number

CN202010405942.3A

Other languages

English (en)

Chinese (zh)

Inventor

斯蒂芬·斯托克斯

克里斯多佛·约翰·格雷厄姆

斯图亚特·克里斯多佛·雷

艾玛·杰妮·斯蒂芬尼亚克

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Werneris R&d Co ltd

Original Assignee

Werneris R&d Co 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.)

2012-01-30

Filing date

2013-01-30

Publication date

2020-08-04

2013-01-30 Application filed by Werneris R&d Co ltd filed Critical Werneris R&d Co ltd

2020-08-04 Publication of CN111484493A publication Critical patent/CN111484493A/zh

Status Pending legal-status Critical Current

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150000005258 1H-pyrrolo(2,3-b)pyridines Chemical class 0.000 title abstract description 7
229940043355 kinase inhibitor Drugs 0.000 title abstract description 4
239000003757 phosphotransferase inhibitor Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 356
-1 O-methyl Chemical group 0.000 claims description 66
125000000623 heterocyclic group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000003107 substituted aryl group Chemical group 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 11
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 6
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000732 arylene group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005549 heteroarylene group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 317
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 282
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 200
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 150
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 140
239000007787 solid Substances 0.000 description 121
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 115
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 108
238000002360 preparation method Methods 0.000 description 103
235000019439 ethyl acetate Nutrition 0.000 description 100
238000005481 NMR spectroscopy Methods 0.000 description 99
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 97
229920006395 saturated elastomer Polymers 0.000 description 96
KGDOHXYALMXHLF-UHFFFAOYSA-N 1-benzylpyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC=C1 KGDOHXYALMXHLF-UHFFFAOYSA-N 0.000 description 93
239000000243 solution Substances 0.000 description 89
238000006243 chemical reaction Methods 0.000 description 82
239000000203 mixture Substances 0.000 description 78
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 76
229910052943 magnesium sulfate Inorganic materials 0.000 description 75
235000019341 magnesium sulphate Nutrition 0.000 description 75
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239000011780 sodium chloride Substances 0.000 description 70
238000000034 method Methods 0.000 description 64
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239000000047 product Substances 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
238000004440 column chromatography Methods 0.000 description 52
239000013058 crude material Substances 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
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238000007792 addition Methods 0.000 description 36
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AKKPGUPOFLAXRN-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=C(F)C=C1 AKKPGUPOFLAXRN-UHFFFAOYSA-N 0.000 description 20
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
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238000003818 flash chromatography Methods 0.000 description 20
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 20
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238000002953 preparative HPLC Methods 0.000 description 18
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 description 13
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239000000706 filtrate Substances 0.000 description 13
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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WUOQXNWMYLFAHT-MRVPVSSYSA-N tert-butyl n-[(3r)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCCNC1 WUOQXNWMYLFAHT-MRVPVSSYSA-N 0.000 description 12
201000011510 cancer Diseases 0.000 description 11
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125000001424 substituent group Chemical group 0.000 description 11
RJAFVJZCUMEOBR-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=NC=C1 RJAFVJZCUMEOBR-UHFFFAOYSA-N 0.000 description 10
241000400611 Eucalyptus deanei Species 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 9
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DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
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LRZZXMQRQHIQAQ-SNVBAGLBSA-N tert-butyl n-[(3r)-1-[3-amino-5-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-yl]carbamate Chemical compound C1[C@H](NC(=O)OC(C)(C)C)CCCN1C1=C(C(F)(F)F)C=NC2=C1C(N)=CN2 LRZZXMQRQHIQAQ-SNVBAGLBSA-N 0.000 description 1
OGPCSYUFPBVGKD-SNVBAGLBSA-N tert-butyl n-[(3r)-1-[3-nitro-5-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-yl]carbamate Chemical compound C1[C@H](NC(=O)OC(C)(C)C)CCCN1C1=C(C(F)(F)F)C=NC2=C1C([N+]([O-])=O)=CN2 OGPCSYUFPBVGKD-SNVBAGLBSA-N 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229960001196 thiotepa Drugs 0.000 description 1
FBGKGORFGWHADY-UHFFFAOYSA-N tin(2+);dihydrate Chemical compound O.O.[Sn+2] FBGKGORFGWHADY-UHFFFAOYSA-N 0.000 description 1
229960003087 tioguanine Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000016596 traversing start control point of mitotic cell cycle Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
208000022679 triple-negative breast carcinoma Diseases 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
235000019798 tripotassium phosphate Nutrition 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
238000013022 venting Methods 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Dermatology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CN202010405942.3A 2012-01-30 2013-01-30 1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途 Pending CN111484493A (zh)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB1201566.5		2012-01-30
GBGB1201566.5A GB201201566D0 (en)	2012-01-30	2012-01-30	New chemical compounds
CN201380014717.5A CN104203948A (zh)	2012-01-30	2013-01-30	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途

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Publications (1)

Publication Number	Publication Date
CN111484493A true CN111484493A (zh)	2020-08-04

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ID=45876325

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CN201610920724.7A Pending CN107011341A (zh)	2012-01-30	2013-01-30	1H‑吡咯并[2,3‑b]吡啶衍生物及它们作为激酶抑制剂的用途
CN201610920720.9A Expired - Fee Related CN106866658B (zh)	2012-01-30	2013-01-30	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途
CN202010405942.3A Pending CN111484493A (zh)	2012-01-30	2013-01-30	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途
CN201380014717.5A Pending CN104203948A (zh)	2012-01-30	2013-01-30	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途

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CN201610920724.7A Pending CN107011341A (zh)	2012-01-30	2013-01-30	1H‑吡咯并[2,3‑b]吡啶衍生物及它们作为激酶抑制剂的用途
CN201610920720.9A Expired - Fee Related CN106866658B (zh)	2012-01-30	2013-01-30	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途

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Country Status (21)

Country	Link
US (3)	US10000481B2 (2)
EP (1)	EP2809670B1 (2)
JP (1)	JP6199316B2 (2)
CN (4)	CN107011341A (2)
AU (1)	AU2013213954B2 (2)
BR (1)	BR112014018795B1 (2)
CA (1)	CA2862940C (2)
DK (1)	DK2809670T3 (2)
EA (1)	EA026657B1 (2)
ES (1)	ES2637340T3 (2)
GB (1)	GB201201566D0 (2)
HK (1)	HK1200447A1 (2)
HU (1)	HUE035332T2 (2)
IL (1)	IL233595B (2)
IN (1)	IN2014DN06104A (2)
MX (1)	MX352927B (2)
NZ (1)	NZ627361A (2)
PL (1)	PL2809670T3 (2)
PT (1)	PT2809670T (2)
WO (1)	WO2013114113A1 (2)
ZA (1)	ZA201405070B (2)

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CN105705499B (zh) *	2013-08-22	2018-10-12	基因泰克公司	用于制备化合物的方法
CN104829609B (zh) *	2014-02-11	2016-08-03	北大方正集团有限公司	取代的吡啶并嘧啶化合物及其制备方法和应用
MA41559A (fr) *	2015-09-08	2017-12-26	Taiho Pharmaceutical Co Ltd	Composé de pyrimidine condensé ou un sel de celui-ci
US10032914B2 (en) *	2015-10-20	2018-07-24	Taiwan Semiconductor Manufacturing Co., Ltd.	Semiconductor device and manufacturing method thereof
CA3015484C (en)	2016-02-23	2022-11-08	Taiho Pharmaceutical Co., Ltd.	Novel condensed pyrimidine compound or salt thereof
EP3674325A4 (en)	2017-08-21	2021-11-03	Taiho Pharmaceutical Co., Ltd.	FUSION PROTEIN OF DCTN1 PROTEIN WITH RET PROTEIN
TW202043198A (zh)	2019-01-17	2020-12-01	美商ＩｆｍＤｕｅ有限公司	用於治療與sting活性相關之病況的化合物及組合物
CN111518096B (zh)	2019-02-02	2022-02-11	江苏威凯尔医药科技有限公司	两面神激酶jak家族抑制剂及其制备和应用
US12428395B2 (en)	2019-08-01	2025-09-30	Sperogenix Therapeutics Limited	Heterocyclic compounds as kinase inhibitor and uses thereof
IT202000005527A1 (it) *	2020-03-16	2021-09-16	Univ Degli Studi Di Trento	Trattamento terapeutico di cromatinopatie
JP2023540674A (ja) *	2020-07-15	2023-09-26	アイエフエムデューインコーポレイテッド	Ｓｔｉｎｇ活性に関連する状態を治療するための化合物および組成物
WO2022015975A1 (en)	2020-07-15	2022-01-20	Ifm Due, Inc.	Compounds and compositions for treating conditions associated with sting activity
PY2157405A (es) *	2020-07-15	2022-04-22	Ifm Due Inc	Compuestos y composiciones para el tratamiento de afecciones asociadas a la actividad del sting
EP4274824A1 (en)	2021-01-08	2023-11-15	IFM Due, Inc.	Heterobicyclic compounds having an urea or analogue and their compositions for treating conditions associated with sting activity
IL310724A (en)	2021-08-10	2024-04-01	Ifm Due Inc	COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF CONDITIONS ASSOCIATED WITH STING ACTIVITY
CN118613473A (zh) *	2022-01-12	2024-09-06	艾福姆德尤股份有限公司	用于治疗与sting活性相关的病症的化合物和组合物

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2012
- 2012-01-30 GB GBGB1201566.5A patent/GB201201566D0/en not_active Ceased
2013
- 2013-01-30 PT PT137031217T patent/PT2809670T/pt unknown
- 2013-01-30 MX MX2014009112A patent/MX352927B/es active IP Right Grant
- 2013-01-30 HK HK15100794.1A patent/HK1200447A1/xx unknown
- 2013-01-30 JP JP2014555310A patent/JP6199316B2/ja not_active Expired - Fee Related
- 2013-01-30 AU AU2013213954A patent/AU2013213954B2/en active Active
- 2013-01-30 DK DK13703121.7T patent/DK2809670T3/en active
- 2013-01-30 IN IN6104DEN2014 patent/IN2014DN06104A/en unknown
- 2013-01-30 CN CN201610920724.7A patent/CN107011341A/zh active Pending
- 2013-01-30 CN CN201610920720.9A patent/CN106866658B/zh not_active Expired - Fee Related
- 2013-01-30 CN CN202010405942.3A patent/CN111484493A/zh active Pending
- 2013-01-30 EP EP13703121.7A patent/EP2809670B1/en active Active
- 2013-01-30 CN CN201380014717.5A patent/CN104203948A/zh active Pending
- 2013-01-30 ES ES13703121.7T patent/ES2637340T3/es active Active
- 2013-01-30 WO PCT/GB2013/050212 patent/WO2013114113A1/en not_active Ceased
- 2013-01-30 EA EA201491376A patent/EA026657B1/ru not_active IP Right Cessation
- 2013-01-30 NZ NZ627361A patent/NZ627361A/en not_active IP Right Cessation
- 2013-01-30 PL PL13703121T patent/PL2809670T3/pl unknown
- 2013-01-30 CA CA2862940A patent/CA2862940C/en active Active
- 2013-01-30 HU HUE13703121A patent/HUE035332T2/en unknown
- 2013-01-30 BR BR112014018795-9A patent/BR112014018795B1/pt not_active IP Right Cessation
- 2013-01-30 US US14/375,353 patent/US10000481B2/en active Active
2014
- 2014-07-10 IL IL233595A patent/IL233595B/en active IP Right Grant
- 2014-07-11 ZA ZA2014/05070A patent/ZA201405070B/en unknown
2018
- 2018-06-15 US US16/009,439 patent/US10889582B2/en active Active
2020
- 2020-11-30 US US17/107,176 patent/US20210206762A1/en not_active Abandoned

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CN104203948A (zh) *	2012-01-30	2014-12-10	沃纳利斯(R&D)有限公司	1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途
CN106866658A (zh) *	2012-01-30	2017-06-20	沃纳利斯(R&D)有限公司	1H‑吡咯并[2,3‑b]吡啶衍生物及它们作为激酶抑制剂的用途
CN107011341A (zh) *	2012-01-30	2017-08-04	沃纳利斯(R&D)有限公司	1H‑吡咯并[2,3‑b]吡啶衍生物及它们作为激酶抑制剂的用途

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CN106866658A (zh)	2017-06-20
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IN2014DN06104A (2)	2015-08-14
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US10000481B2 (en)	2018-06-19
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