IL93041A - 3-) 1,2,5,6-Tetrahydropyrid-4 il (- H1 Pyrolopyridines and medicinal preparations containing them - Google Patents
3-) 1,2,5,6-Tetrahydropyrid-4 il (- H1 Pyrolopyridines and medicinal preparations containing themInfo
- Publication number
- IL93041A IL93041A IL9304190A IL9304190A IL93041A IL 93041 A IL93041 A IL 93041A IL 9304190 A IL9304190 A IL 9304190A IL 9304190 A IL9304190 A IL 9304190A IL 93041 A IL93041 A IL 93041A
- Authority
- IL
- Israel
- Prior art keywords
- pyrrolo
- pyridine
- tetrahydropyrid
- hydrogen
- nmr
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- UTZWZATUUDPCFB-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical class C1NCCC(C=2C3=NC=CC=C3NC=2)=C1 UTZWZATUUDPCFB-UHFFFAOYSA-N 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 37
- -1 phenyloxy Chemical group 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- PJYVGMRFPFNZCT-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1,4-dihydropyrrolo[3,2-b]pyridin-5-one Chemical compound C1=2NC(=O)C=CC=2NC=C1C1=CCNCC1 PJYVGMRFPFNZCT-UHFFFAOYSA-N 0.000 claims description 4
- KWQWBZIGHIOKIO-UHFFFAOYSA-N 5-propoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OCCC)=CC=C2NC=C1C1=CCNCC1 KWQWBZIGHIOKIO-UHFFFAOYSA-N 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 230000016571 aggressive behavior Effects 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- CILLFDCHNZEIGM-UHFFFAOYSA-N 5-propan-2-yloxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OC(C)C)=CC=C2NC=C1C1=CCNCC1 CILLFDCHNZEIGM-UHFFFAOYSA-N 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- WIHXNJLRQMHBFE-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[2,3-c]pyridine Chemical compound C1NCCC(C=2C3=CC=NC=C3NC=2)=C1 WIHXNJLRQMHBFE-UHFFFAOYSA-N 0.000 claims description 2
- ABSVAQCGVZCXOI-UHFFFAOYSA-N 5-cyclopentyloxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C1CCCC1OC1=CC=C(NC=C2C=3CCNCC=3)C2=N1 ABSVAQCGVZCXOI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- OQDGBIQQFFTLKL-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1NCCC(C=2C3=CC=CN=C3NC=2)=C1 OQDGBIQQFFTLKL-UHFFFAOYSA-N 0.000 claims 1
- JPZXYOVLOYJXAV-UHFFFAOYSA-N 5-[(2-methylpropan-2-yl)oxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OC(C)(C)C)=CC=C2NC=C1C1=CCNCC1 JPZXYOVLOYJXAV-UHFFFAOYSA-N 0.000 claims 1
- OQCCIRJNHWTROW-UHFFFAOYSA-N 5-butoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OCCCC)=CC=C2NC=C1C1=CCNCC1 OQCCIRJNHWTROW-UHFFFAOYSA-N 0.000 claims 1
- MQTZUWUYJPCZID-UHFFFAOYSA-N 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(Cl)=CC=C2NC=C1C1=CCNCC1 MQTZUWUYJPCZID-UHFFFAOYSA-N 0.000 claims 1
- RBFMRHDBVILZMO-UHFFFAOYSA-N 5-ethoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(OCC)=CC=C2NC=C1C1=CCNCC1 RBFMRHDBVILZMO-UHFFFAOYSA-N 0.000 claims 1
- GSVMOOFAJGTVAZ-UHFFFAOYSA-N 5-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C12=NC(C)=CC=C2NC=C1C1=CCNCC1 GSVMOOFAJGTVAZ-UHFFFAOYSA-N 0.000 claims 1
- SNJLSZVIOFJOIE-UHFFFAOYSA-N 5-phenylmethoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C=1C=CC=CC=1COC(N=C12)=CC=C1NC=C2C1=CCNCC1 SNJLSZVIOFJOIE-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002539 anti-aggressive effect Effects 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 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 1
- GXTMDNJITXSIRL-UHFFFAOYSA-N n,n-dimethyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C12=NC(N(C)C)=CC=C2NC=C1C1=CCNCC1 GXTMDNJITXSIRL-UHFFFAOYSA-N 0.000 claims 1
- MTXPFWNUKVMJLO-UHFFFAOYSA-N 3-(3,6-dihydro-2h-pyridin-1-yl)-1h-pyrrolo[3,2-b]pyridine Chemical compound C1C=CCCN1C1=CNC2=CC=CN=C12 MTXPFWNUKVMJLO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
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- 239000000243 solution Substances 0.000 description 37
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- 238000005481 NMR spectroscopy Methods 0.000 description 32
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 26
- 101150041968 CDC13 gene Proteins 0.000 description 25
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
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- 230000035484 reaction time Effects 0.000 description 19
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- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 5
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- 238000000034 method Methods 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- RBMWKMUXNBCUPZ-UHFFFAOYSA-N 5-phenylmethoxy-1h-pyrrolo[3,2-b]pyridine Chemical compound C=1C=C2NC=CC2=NC=1OCC1=CC=CC=C1 RBMWKMUXNBCUPZ-UHFFFAOYSA-N 0.000 description 4
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- XTXUDUUPOZHIMK-UHFFFAOYSA-N n,n-dimethyl-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound CN(C)C1=CC=C2NC=CC2=N1 XTXUDUUPOZHIMK-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- MKYZUGYKWHDLJJ-UHFFFAOYSA-N 5-butoxy-1h-pyrrolo[3,2-b]pyridine Chemical compound CCCCOC1=CC=C2NC=CC2=N1 MKYZUGYKWHDLJJ-UHFFFAOYSA-N 0.000 description 3
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- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
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Classifications
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1989/000231 WO1990007926A1 (en) | 1989-01-20 | 1989-01-20 | 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL93041A0 IL93041A0 (en) | 1990-11-05 |
| IL93041A true IL93041A (en) | 1994-02-27 |
Family
ID=22214793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9304190A IL93041A (en) | 1989-01-20 | 1990-01-12 | 3-) 1,2,5,6-Tetrahydropyrid-4 il (- H1 Pyrolopyridines and medicinal preparations containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US5051412A (xx) |
| EP (1) | EP0379314B1 (xx) |
| JP (1) | JPH0751576B2 (xx) |
| KR (1) | KR920010642B1 (xx) |
| CN (1) | CN1025998C (xx) |
| AT (1) | ATE103282T1 (xx) |
| CA (1) | CA2008016A1 (xx) |
| CS (1) | CS277611B6 (xx) |
| DD (2) | DD291559A5 (xx) |
| DE (1) | DE69007501T2 (xx) |
| DK (1) | DK0379314T3 (xx) |
| EG (1) | EG18945A (xx) |
| ES (1) | ES2062319T3 (xx) |
| FI (1) | FI94641C (xx) |
| HU (1) | HU206349B (xx) |
| IE (1) | IE62757B1 (xx) |
| IL (1) | IL93041A (xx) |
| MX (1) | MX19185A (xx) |
| MY (1) | MY106305A (xx) |
| NO (1) | NO912860D0 (xx) |
| NZ (1) | NZ232166A (xx) |
| PL (2) | PL287840A1 (xx) |
| PT (1) | PT92889A (xx) |
| WO (1) | WO1990007926A1 (xx) |
| YU (1) | YU47553B (xx) |
| ZA (1) | ZA90393B (xx) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX19185A (es) * | 1989-01-20 | 1993-12-01 | Pfizer | Procedimiento para preparar 3-(1,2,5,6-tretrahidropiridil)-pirrolopiridinas. |
| US5451566A (en) * | 1993-11-17 | 1995-09-19 | Zeneca Limited | Herbicidal pyrrolopyridine compounds |
| US6586458B1 (en) | 1996-08-16 | 2003-07-01 | Pozen Inc. | Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs |
| EP1082958A3 (en) * | 1996-11-15 | 2002-12-11 | Eli Lilly And Company | 5-HT1F agonists in chronic pain |
| ZA979961B (en) * | 1996-11-15 | 1999-05-05 | Lilly Co Eli | 5-HT1F agonists |
| EP0875513A1 (en) * | 1997-04-14 | 1998-11-04 | Eli Lilly And Company | Substituted heteroaromatic 5-HT 1F agonists |
| US5905084A (en) * | 1997-11-14 | 1999-05-18 | Eli Lilly And Company | 5-HTIF -agonists effective in treating migraine |
| ZA989389B (en) * | 1997-11-14 | 2000-04-14 | Lilly Co Eli | Pyrrolo [3,2-b] pyridine processes and intermediates. |
| US6476034B2 (en) | 2000-02-22 | 2002-11-05 | Bristol-Myers Squibb Company | Antiviral azaindole derivatives |
| US7332183B2 (en) | 2002-12-26 | 2008-02-19 | Pozen Inc. | Multilayer dosage forms containing NSAIDs and triptans |
| CN102786482A (zh) * | 2003-11-21 | 2012-11-21 | 阿雷生物药品公司 | Akt蛋白激酶抑制剂 |
| US7626021B2 (en) * | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| US7361764B2 (en) * | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| MX2007001127A (es) | 2004-07-27 | 2007-07-11 | Sgx Pharmaceuticals Inc | Moduladores de pirrolo-piridina cinasa. |
| MX2007001126A (es) | 2004-07-27 | 2007-09-25 | Sgx Pharmaceuticals Inc | Moduladores de heterociclo cinasa de anillo fusionado. |
| US20060100432A1 (en) | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
| US7851476B2 (en) | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
| US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
| US8063050B2 (en) * | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2054418B1 (en) | 2006-07-06 | 2011-11-09 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| DE602007011628D1 (de) | 2006-07-06 | 2011-02-10 | Array Biopharma Inc | Dihydrofuropyrimidine als akt-proteinkinaseinhibitoren |
| RU2481336C2 (ru) | 2006-07-06 | 2013-05-10 | Эррэй Биофарма Инк. | Циклопента(d)пиримидины в качестве ингибиторов протеинкиназ акт |
| PL2114955T3 (pl) | 2006-12-29 | 2013-06-28 | Rigel Pharmaceuticals Inc | Triazole podstawione mostkowanym bicyklicznym arylem oraz mostkowanym bicyklicznym heteroarylem użyteczne jako inhibitory Axl |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| CN103396409B (zh) | 2007-07-05 | 2015-03-11 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| KR20150091196A (ko) * | 2007-07-05 | 2015-08-07 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| WO2009089459A1 (en) * | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| JP5539225B2 (ja) * | 2008-01-09 | 2014-07-02 | アレイ バイオファーマ、インコーポレイテッド | Ａｋｔタンパク質キナーゼ阻害剤としての水酸化されたピリミジルシクロペンタン |
| US8546433B2 (en) | 2009-01-16 | 2013-10-01 | Rigel Pharmaceuticals, Inc. | Axl inhibitors for use in combination therapy for preventing, treating or managing metastatic cancer |
| EP3141252B8 (en) | 2009-06-17 | 2019-03-13 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| CN103492381A (zh) | 2010-12-16 | 2014-01-01 | 沃泰克斯药物股份有限公司 | 流感病毒复制的抑制剂 |
| EP2694072B1 (en) | 2011-04-01 | 2017-11-29 | Genentech, Inc. | Combination of akt inhibitor compound and abiraterone for use in therapeutic treatments |
| MX2013011333A (es) | 2011-04-01 | 2014-04-16 | Genentech Inc | Combinaciones de compuestos inhibidores de akt y mek, y metodos de uso. |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| JP6440625B2 (ja) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 精神分裂病を処置するための方法および組成物 |
| AU2014348840B2 (en) | 2013-11-13 | 2019-06-06 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| EP3851437A3 (en) | 2013-11-13 | 2021-11-03 | Vertex Pharmaceuticals Incorporated | Methods of preparing 1h-pyrrolo[2,3-b]pyridine derivates |
| EP3209663B1 (en) | 2014-10-23 | 2018-12-12 | Janssen Pharmaceutica N.V. | New pyrazolopyrimidine derivatives as nik inhibitors |
| CA2960567C (en) | 2014-10-23 | 2023-03-07 | Janssen Pharmaceutica Nv | Thienopyrimidine derivatives as nik inhibitors |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272804A (en) * | 1963-12-23 | 1966-09-13 | Sterling Drug Inc | Process and intermediates for preparing indoles |
| GB1141949A (en) * | 1966-02-23 | 1969-02-05 | Sterling Drug Inc | 7-azaindole derivatives |
| IL48508A (en) * | 1974-12-09 | 1979-10-31 | Roussel Uclaf | Pharmaceutical compositions comprising piperidylindole derivatives |
| FR2362628A1 (fr) * | 1976-08-26 | 1978-03-24 | Roussel Uclaf | Nouveaux derives du piperidyl-indole et leurs sels, procede de preparation et application a titre de medicaments |
| FR2421899A1 (fr) * | 1978-01-16 | 1979-11-02 | Roussel Uclaf | Nouveaux derives du tetrahydropyridinyl-indole et leurs sels, le procede de preparation et l'application a titre de medicaments de ces nouveaux produits |
| FR2444678A2 (fr) * | 1978-12-22 | 1980-07-18 | Roussel Uclaf | Nouveau procede de preparation de derives du piperidyl-indole et de leurs sels |
| US5025096A (en) * | 1985-08-22 | 1991-06-18 | Mine Safety Appliances Company | Preparation of indole and indole derivatives |
| MX19185A (es) * | 1989-01-20 | 1993-12-01 | Pfizer | Procedimiento para preparar 3-(1,2,5,6-tretrahidropiridil)-pirrolopiridinas. |
-
1989
- 1989-01-20 MX MX1918590A patent/MX19185A/es unknown
- 1989-01-20 WO PCT/US1989/000231 patent/WO1990007926A1/en active IP Right Grant
- 1989-01-23 US US07/576,429 patent/US5051412A/en not_active Expired - Lifetime
- 1989-01-23 HU HU9249A patent/HU206349B/hu not_active IP Right Cessation
-
1990
- 1990-01-12 DE DE69007501T patent/DE69007501T2/de not_active Expired - Fee Related
- 1990-01-12 AT AT90300361T patent/ATE103282T1/de active
- 1990-01-12 EP EP90300361A patent/EP0379314B1/en not_active Expired - Lifetime
- 1990-01-12 ES ES90300361T patent/ES2062319T3/es not_active Expired - Lifetime
- 1990-01-12 DK DK90300361.4T patent/DK0379314T3/da active
- 1990-01-12 IL IL9304190A patent/IL93041A/en not_active IP Right Cessation
- 1990-01-17 EG EG2690A patent/EG18945A/xx active
- 1990-01-17 MY MYPI90000082A patent/MY106305A/en unknown
- 1990-01-18 PT PT92889A patent/PT92889A/pt unknown
- 1990-01-18 CA CA002008016A patent/CA2008016A1/en not_active Abandoned
- 1990-01-18 CS CS90260A patent/CS277611B6/cs not_active IP Right Cessation
- 1990-01-19 PL PL28784090A patent/PL287840A1/xx unknown
- 1990-01-19 YU YU9990A patent/YU47553B/sh unknown
- 1990-01-19 ZA ZA90393A patent/ZA90393B/xx unknown
- 1990-01-19 NZ NZ232166A patent/NZ232166A/en unknown
- 1990-01-19 DD DD90337216A patent/DD291559A5/de not_active IP Right Cessation
- 1990-01-19 KR KR1019900000626A patent/KR920010642B1/ko not_active IP Right Cessation
- 1990-01-19 CN CN90100888A patent/CN1025998C/zh not_active Expired - Fee Related
- 1990-01-19 IE IE21090A patent/IE62757B1/en not_active IP Right Cessation
- 1990-01-19 DD DD90343473A patent/DD298398A5/de not_active IP Right Cessation
- 1990-01-19 JP JP2010431A patent/JPH0751576B2/ja not_active Expired - Lifetime
- 1990-01-19 PL PL90283354A patent/PL163626B1/pl unknown
-
1991
- 1991-07-22 FI FI913509A patent/FI94641C/fi not_active IP Right Cessation
- 1991-07-22 NO NO1991912860A patent/NO912860D0/no unknown
- 1991-09-20 US US07/763,081 patent/US5169947A/en not_active Expired - Lifetime
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| RH | Patent void |