CA2285263C - Furopyridine, thienopyridine, pyrrolopyridine, et composes correspondants de pyrimidine, pyridazine et triazine convenant particulierement au controle de la chimio-transmission synaptique - Google Patents
Furopyridine, thienopyridine, pyrrolopyridine, et composes correspondants de pyrimidine, pyridazine et triazine convenant particulierement au controle de la chimio-transmission synaptique Download PDFInfo
- Publication number
- CA2285263C CA2285263C CA002285263A CA2285263A CA2285263C CA 2285263 C CA2285263 C CA 2285263C CA 002285263 A CA002285263 A CA 002285263A CA 2285263 A CA2285263 A CA 2285263A CA 2285263 C CA2285263 C CA 2285263C
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- Canada
- Prior art keywords
- alkyl
- substituted
- phenyl
- compound
- heteroaryl
- 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.)
- Expired - Fee Related
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- 239000000126 substance Substances 0.000 title claims abstract description 24
- 230000005062 synaptic transmission Effects 0.000 title claims abstract description 23
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 title claims description 13
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 6
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 title description 5
- 229940125670 thienopyridine Drugs 0.000 title description 5
- 239000002175 thienopyridine Substances 0.000 title description 5
- 150000003918 triazines Chemical class 0.000 title description 4
- -1 heterocyclic ether compounds Chemical class 0.000 claims abstract description 192
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 398
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
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- 239000003814 drug Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 11
- FEVBLIMLWKRQRY-JTQLQIEISA-N 2-[(2s)-1-methylpyrrolidin-2-yl]furo[2,3-b]pyridine Chemical compound CN1CCC[C@H]1C1=CC2=CC=CN=C2O1 FEVBLIMLWKRQRY-JTQLQIEISA-N 0.000 claims 1
- KYRHPRNLMNBROP-CYBMUJFWSA-N 3-[5-chloro-2-[(2r)-pyrrolidin-2-yl]furo[3,2-b]pyridin-6-yl]aniline Chemical compound NC1=CC=CC(C=2C(=NC=3C=C(OC=3C=2)[C@@H]2NCCC2)Cl)=C1 KYRHPRNLMNBROP-CYBMUJFWSA-N 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 125
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- 150000001412 amines Chemical class 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
- 229940032712 succinylcholine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- UZDCMXKRXSNGGO-LLVKDONJSA-N tert-butyl (2r)-2-(5,6-dichlorofuro[3,2-b]pyridin-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C1=CC2=NC(Cl)=C(Cl)C=C2O1 UZDCMXKRXSNGGO-LLVKDONJSA-N 0.000 description 1
- ASDOMKAUCZGQCP-GMUIIQOCSA-N tert-butyl (2r)-2-(6-benzoylfuro[3,2-b]pyridin-2-yl)pyrrolidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CCC[C@@H]1C1=CC2=NC=C(C(=O)C=3C=CC=CC=3)C=C2O1 ASDOMKAUCZGQCP-GMUIIQOCSA-N 0.000 description 1
- UMYFOKXJUDWICI-GFCCVEGCSA-N tert-butyl (2r)-2-(6-bromofuro[3,2-b]pyridin-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C1=CC2=NC=C(Br)C=C2O1 UMYFOKXJUDWICI-GFCCVEGCSA-N 0.000 description 1
- YDBPZCVWPFMBDH-MRVPVSSYSA-N tert-butyl (2r)-2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C=O YDBPZCVWPFMBDH-MRVPVSSYSA-N 0.000 description 1
- ACIMJAZMWGJTCY-GFCCVEGCSA-N tert-butyl (2r)-2-furo[3,2-b]pyridin-2-ylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C1=CC2=NC=CC=C2O1 ACIMJAZMWGJTCY-GFCCVEGCSA-N 0.000 description 1
- JWFDOOYFPLLVIV-LBPRGKRZSA-N tert-butyl (2s)-2-(6-chlorofuro[3,2-b]pyridin-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CC2=NC=C(Cl)C=C2O1 JWFDOOYFPLLVIV-LBPRGKRZSA-N 0.000 description 1
- NZWQRJIRXUMMQM-LBPRGKRZSA-N tert-butyl (2s)-2-(7-chlorofuro[3,2-b]pyridin-2-yl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CC2=NC=CC(Cl)=C2O1 NZWQRJIRXUMMQM-LBPRGKRZSA-N 0.000 description 1
- SNVBWOPEVYKDGO-MWBUKTMBSA-N tert-butyl (2s)-2-formylpyrrolidine-1-carboxylate;(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C=O.CC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O SNVBWOPEVYKDGO-MWBUKTMBSA-N 0.000 description 1
- XKVQAYGKIVIHNV-LBPRGKRZSA-N tert-butyl (2s)-2-furo[2,3-b]pyridin-2-ylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CC2=CC=CN=C2O1 XKVQAYGKIVIHNV-LBPRGKRZSA-N 0.000 description 1
- ACIMJAZMWGJTCY-LBPRGKRZSA-N tert-butyl (2s)-2-furo[3,2-b]pyridin-2-ylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=CC2=NC=CC=C2O1 ACIMJAZMWGJTCY-LBPRGKRZSA-N 0.000 description 1
- XDAXBEAXQVXDLY-UHFFFAOYSA-N tert-butyl 2h-thieno[3,2-b]pyridine-4-carboxylate Chemical class CC(C)(C)OC(=O)N1C=CC=C2SCC=C12 XDAXBEAXQVXDLY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- PWSBNTOBQBTNEJ-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=C[CH]C2=C=CSC2=N1 PWSBNTOBQBTNEJ-UHFFFAOYSA-N 0.000 description 1
- UYGIYVMPGNRKTG-UHFFFAOYSA-N thieno[2,3-c]pyridazine Chemical class C1=NN=C2SC=CC2=C1 UYGIYVMPGNRKTG-UHFFFAOYSA-N 0.000 description 1
- UKFCLFUPQDATFH-UHFFFAOYSA-N thieno[2,3-d]triazine Chemical class N1=NN=C2SC=CC2=C1 UKFCLFUPQDATFH-UHFFFAOYSA-N 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- CFQJBWKKHCMCGJ-UHFFFAOYSA-N tributyl(pyridin-3-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN=C1 CFQJBWKKHCMCGJ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—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
- A61K31/4355—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 oxygen as a ring hetero atom
-
- 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La présente invention concerne un composé éther hétérocyclique représenté par la formule générale (I) et convenant particulièrement au contrôle sélectif de la chimio-transmission synaptique. Dans cette formule, A, m, R, X, Y<1>, Y<2> et Y<3> sont conformes à la description qui en est donnée par les revendications. L'invention concerne également des compositions pharmaceutiques à base de ces produits, lesquelles compositions présentent une efficacité thérapeutique. L'invention concerne enfin l'utilisation de ces compositions pour le contrôle sélectif de la transmission synaptique chez les mammifères.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/834,053 US6001849A (en) | 1995-07-28 | 1997-04-11 | Furopyridine, thienopyridine pyrrolopyridine useful in controlling chemical synaptic transmission |
| US08/834,053 | 1997-04-11 | ||
| PCT/US1998/007128 WO1998046609A1 (fr) | 1997-04-11 | 1998-04-10 | Furopyridine, thienopyridine, pyrrolopyridine, et composes correspondants de pyrimidine, pyridazine et triazine convenant particulierement au controle de la chimio-transmission synaptique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285263A1 CA2285263A1 (fr) | 1998-10-22 |
| CA2285263C true CA2285263C (fr) | 2009-03-10 |
Family
ID=25265973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285263A Expired - Fee Related CA2285263C (fr) | 1997-04-11 | 1998-04-10 | Furopyridine, thienopyridine, pyrrolopyridine, et composes correspondants de pyrimidine, pyridazine et triazine convenant particulierement au controle de la chimio-transmission synaptique |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0973777A1 (fr) |
| JP (1) | JP2001521523A (fr) |
| CA (1) | CA2285263C (fr) |
| WO (1) | WO1998046609A1 (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0955301A3 (fr) * | 1998-04-27 | 2001-04-18 | Pfizer Products Inc. | Dérivés de 7-aza-bicyclo[2.2.1]-heptane, leur préparation et utilisation sur la base d'affinité pour les recepteurs de l'acetylcholine nicotinique neuronaux |
| EP1558252B1 (fr) | 2002-08-02 | 2007-10-10 | Merck & Co., Inc. | Derives de furo[2,3-b]pyridine substitues |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| ES2704744T3 (es) | 2012-06-13 | 2019-03-19 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| MX373169B (es) | 2015-02-20 | 2020-04-24 | Incyte Holdings Corp | Heterociclos bicíclicos como inhibidores de receptores del factor de crecimiento fibroblástico (fgfr). |
| WO2016134294A1 (fr) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| MA52493A (fr) | 2018-05-04 | 2021-03-10 | Incyte Corp | Sels d'un inhibiteur de fgfr |
| CR20200590A (es) | 2018-05-04 | 2021-04-26 | Incyte Corp | Formas sólidas de un inhibidor de fgfr y procesos para prepararlas |
| US20220056043A1 (en) * | 2019-02-19 | 2022-02-24 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | Nitrogen-containing fused cyclic compound, preparation method therefor and use thereof |
| WO2020185532A1 (fr) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Méthodes de traitement du cancer au moyen d'un inhibiteur de fgfr |
| WO2021007269A1 (fr) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
| WO2021067374A1 (fr) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
| TWI891666B (zh) | 2019-10-14 | 2025-08-01 | 美商英塞特公司 | 作為fgfr抑制劑之雙環雜環 |
| WO2021076728A1 (fr) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
| EP4069696A1 (fr) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Hétérocycles tricycliques en tant qu'inhibiteurs de fgfr |
| BR112022010664A2 (pt) | 2019-12-04 | 2022-08-16 | Incyte Corp | Derivados de um inibidor de fgfr |
| WO2021146424A1 (fr) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Hétérocycles bicycliques en tant qu'inhibiteurs de fgfr |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含fgfr抑制劑及nectin-4靶向劑之組合療法 |
| EP4352059A1 (fr) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Hétérocycles tricycliques en tant qu'inhibiteurs de fgfr |
| WO2022261159A1 (fr) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Hétérocycles tricycliques utiles en tant qu'inhibiteurs de fgfr |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9800776A (es) * | 1995-07-28 | 1998-04-30 | Abbott Lab | Furopiridina, tienopiridina, pirrolopiridina y compuestos de triazina, piridazina y pirimidina relacionados utiles para controlar la transmision sinaptica quimica. |
-
1998
- 1998-04-10 EP EP98913418A patent/EP0973777A1/fr not_active Withdrawn
- 1998-04-10 WO PCT/US1998/007128 patent/WO1998046609A1/fr not_active Ceased
- 1998-04-10 CA CA002285263A patent/CA2285263C/fr not_active Expired - Fee Related
- 1998-04-10 JP JP54405598A patent/JP2001521523A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2285263A1 (fr) | 1998-10-22 |
| WO1998046609A1 (fr) | 1998-10-22 |
| EP0973777A1 (fr) | 2000-01-26 |
| JP2001521523A (ja) | 2001-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130410 |