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 them

Info

Publication number: IL93041A
Authority: IL; Israel
Prior art keywords: pyrrolo; pyridine; tetrahydropyrid; hydrogen; nmr
Prior art date: 1989-01-20

Application number

IL9304190A

Other languages

English (en)

Hebrew (he)

Other versions

IL93041A0 (en

Original Assignee

Pfizer

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.)

1989-01-20

Filing date

1990-01-12

Publication date

1994-02-27

1990-01-12 Application filed by Pfizer filed Critical Pfizer

1990-11-05 Publication of IL93041A0 publication Critical patent/IL93041A0/xx

1994-02-27 Publication of IL93041A publication Critical patent/IL93041A/en

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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
239000007787 solid Substances 0.000 description 59
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 32
238000010828 elution Methods 0.000 description 28
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 27
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 26
101150041968 CDC13 gene Proteins 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
229940093499 ethyl acetate Drugs 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 19
230000035484 reaction time Effects 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
239000000284 extract Substances 0.000 description 15
238000003818 flash chromatography Methods 0.000 description 15
229940086542 triethylamine Drugs 0.000 description 15
239000000706 filtrate Substances 0.000 description 14
238000000605 extraction Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000012298 atmosphere Substances 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000007810 chemical reaction solvent Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
YUGDKEWUYZXXRU-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetonitrile Chemical compound ClC1=CC=C(OCC#N)C=C1 YUGDKEWUYZXXRU-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
229910000564 Raney nickel Inorganic materials 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000000843 powder Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000006260 foam Substances 0.000 description 5
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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
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
238000001665 trituration Methods 0.000 description 4
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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241000699670 Mus sp. Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
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239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000002689 maleic acids Chemical class 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
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229910052708 sodium Inorganic materials 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
VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 2
YAUFQXZEUFCKAT-UHFFFAOYSA-N 2-(6-methyl-3-nitropyridin-2-yl)acetonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C(CC#N)=N1 YAUFQXZEUFCKAT-UHFFFAOYSA-N 0.000 description 2
KKKJYDOHVKIIQP-UHFFFAOYSA-N 2-[4-(3-chlorobenzoyl)phenoxy]-N-pyridin-3-ylacetamide Chemical compound ClC=1C=C(C(=O)C2=CC=C(OCC(=O)NC=3C=NC=CC=3)C=C2)C=CC=1 KKKJYDOHVKIIQP-UHFFFAOYSA-N 0.000 description 2
JXNJQUZHZOZWMK-UHFFFAOYSA-N 2-[6-(dimethylamino)-3-nitropyridin-2-yl]acetonitrile Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C(CC#N)=N1 JXNJQUZHZOZWMK-UHFFFAOYSA-N 0.000 description 2
LHASZEBEQGPCFM-CJFMBICVSA-N 2-amino-4-[(1r)-1-[[(6r)-6-[(5-chloro-2-methoxyphenyl)methyl]-7-oxo-3-(phenoxyamino)-5,6-dihydro-2h-1,4-diazepine-1-carbonyl]amino]propyl]benzoic acid Chemical compound C([C@@H]1CNC(CN(C1=O)C(=O)N[C@H](CC)C=1C=C(N)C(C(O)=O)=CC=1)=NOC=1C=CC=CC=1)C1=CC(Cl)=CC=C1OC LHASZEBEQGPCFM-CJFMBICVSA-N 0.000 description 2
HWZUMEVIIGNXGM-UHFFFAOYSA-N 2-chloro-4-methyl-5-nitropyridine Chemical compound CC1=CC(Cl)=NC=C1[N+]([O-])=O HWZUMEVIIGNXGM-UHFFFAOYSA-N 0.000 description 2
DJNQRLCFAHKFLZ-UHFFFAOYSA-N 2-methoxy-4-methyl-5-nitropyridine Chemical compound COC1=CC(C)=C([N+]([O-])=O)C=N1 DJNQRLCFAHKFLZ-UHFFFAOYSA-N 0.000 description 2
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ZTLPHDKBDBRZER-UHFFFAOYSA-N 5-[(2-methylpropan-2-yl)oxy]-1h-pyrrolo[3,2-b]pyridine Chemical compound CC(C)(C)OC1=CC=C2NC=CC2=N1 ZTLPHDKBDBRZER-UHFFFAOYSA-N 0.000 description 2
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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
- 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)
Hematology (AREA)
Obesity (AREA)
Diabetes (AREA)
Child & Adolescent Psychology (AREA)
Pain & Pain Management (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL9304190A 1989-01-20 1990-01-12 3-) 1,2,5,6-Tetrahydropyrid-4 il (- H1 Pyrolopyridines and medicinal preparations containing them IL93041A (en)

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 (de)
EP (1)	EP0379314B1 (de)
JP (1)	JPH0751576B2 (de)
KR (1)	KR920010642B1 (de)
CN (1)	CN1025998C (de)
AT (1)	ATE103282T1 (de)
CA (1)	CA2008016A1 (de)
CS (1)	CS277611B6 (de)
DD (2)	DD298398A5 (de)
DE (1)	DE69007501T2 (de)
DK (1)	DK0379314T3 (de)
EG (1)	EG18945A (de)
ES (1)	ES2062319T3 (de)
FI (1)	FI94641C (de)
HU (1)	HU206349B (de)
IE (1)	IE62757B1 (de)
IL (1)	IL93041A (de)
MX (1)	MX19185A (de)
MY (1)	MY106305A (de)
NO (1)	NO912860L (de)
NZ (1)	NZ232166A (de)
PL (2)	PL163626B1 (de)
PT (1)	PT92889A (de)
WO (1)	WO1990007926A1 (de)
YU (1)	YU47553B (de)
ZA (1)	ZA90393B (de)

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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
SI2054418T1 (sl)	2006-07-06	2012-02-29	Array Biopharma Inc	Dihidrotieno pirimidini kot AKT protein kinazni inhibitorji
US8063050B2 (en) *	2006-07-06	2011-11-22	Array Biopharma Inc.	Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
EP2049500B1 (de)	2006-07-06	2011-09-07	Array Biopharma, Inc.	Cyclopenta [d]-pyrimidine als akt-proteinkinasehemmer
DE602007011628D1 (de)	2006-07-06	2011-02-10	Array Biopharma Inc	Dihydrofuropyrimidine als akt-proteinkinaseinhibitoren
CA2710230C (en)	2006-12-29	2016-02-23	Rigel Pharmaceuticals, Inc.	Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors
CN101801955B (zh)	2007-07-05	2013-05-08	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
US8846683B2 (en)	2007-07-05	2014-09-30	Array Biopharma, Inc.	Pyrimidyl cyclopentanes as Akt protein kinase inhibitors
US9409886B2 (en)	2007-07-05	2016-08-09	Array Biopharma Inc.	Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
SI2173723T1 (sl) *	2007-07-05	2011-12-30	Array Biopharma Inc	Pirimidil ciklopentani kot inhibitorji AKT-protein-kinaze
EP2247578B1 (de) *	2008-01-09	2013-05-22	Array Biopharma, Inc.	Hydroxylierte pyrimidylcyclopentane als akt-proteinkinaseinhibitoren
AU2009204019B2 (en) *	2008-01-09	2014-02-20	Array Biopharma Inc.	Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor
CA2749843C (en)	2009-01-16	2017-09-05	Rigel Pharmaceuticals, Inc.	Axl inhibitors for use in combination therapy for preventing, treating or managing metastatic cancer
NZ597059A (en)	2009-06-17	2014-01-31	Vertex Pharma	Inhibitors of influenza viruses replication
RU2013132681A (ru)	2010-12-16	2015-01-27	Вертекс Фармасьютикалз Инкорпорейтед	Ингибиторы репликации вирусов гриппа
RU2013148817A (ru)	2011-04-01	2015-05-10	Дженентек, Инк.	Комбинации соединений-ингибиторов акт и мек и способы их применения
KR102021157B1 (ko)	2011-04-01	2019-09-11	제넨테크, 인크.	Ａｋｔ 억제제 화합물 및 아비라테론의 조합물, 및 사용 방법
UA118010C2 (uk)	2011-08-01	2018-11-12	Вертекс Фармасьютікалз Інкорпорейтед	Інгібітори реплікації вірусів грипу
WO2014078568A1 (en)	2012-11-14	2014-05-22	The Johns Hopkins University	Methods and compositions for treating schizophrenia
SG10201804026WA (en)	2013-11-13	2018-06-28	Vertex Pharma	Inhibitors of influenza viruses replication
HUE052178T2 (hu)	2013-11-13	2021-04-28	Vertex Pharma	Eljárások influenzavírus-replikáció inhibitorainak elõállítására
CA2960567C (en)	2014-10-23	2023-03-07	Janssen Pharmaceutica Nv	Thienopyrimidine derivatives as nik inhibitors
EA033237B1 (ru) *	2014-10-23	2019-09-30	Янссен Фармацевтика Нв	Новые производные пиразолопиримидина в качестве ингибиторов nik, фармацевтическая композиция и лекарственное средство, содержащее ее
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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
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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 not_active Ceased
- 1989-01-23 HU HU9249A patent/HU206349B/hu not_active IP Right Cessation
- 1989-01-23 US US07/576,429 patent/US5051412A/en not_active Expired - Lifetime
1990
- 1990-01-12 EP EP90300361A patent/EP0379314B1/de not_active Expired - Lifetime
- 1990-01-12 AT AT90300361T patent/ATE103282T1/de active
- 1990-01-12 DE DE69007501T patent/DE69007501T2/de not_active Expired - Fee Related
- 1990-01-12 ES ES90300361T patent/ES2062319T3/es not_active Expired - Lifetime
- 1990-01-12 IL IL9304190A patent/IL93041A/en not_active IP Right Cessation
- 1990-01-12 DK DK90300361.4T patent/DK0379314T3/da active
- 1990-01-17 MY MYPI90000082A patent/MY106305A/en unknown
- 1990-01-17 EG EG2690A patent/EG18945A/xx active
- 1990-01-18 CA CA002008016A patent/CA2008016A1/en not_active Abandoned
- 1990-01-18 PT PT92889A patent/PT92889A/pt unknown
- 1990-01-18 CS CS90260A patent/CS277611B6/cs not_active IP Right Cessation
- 1990-01-19 JP JP2010431A patent/JPH0751576B2/ja not_active Expired - Lifetime
- 1990-01-19 DD DD90343473A patent/DD298398A5/de not_active IP Right Cessation
- 1990-01-19 IE IE21090A patent/IE62757B1/en not_active IP Right Cessation
- 1990-01-19 CN CN90100888A patent/CN1025998C/zh not_active Expired - Fee Related
- 1990-01-19 PL PL90283354A patent/PL163626B1/pl unknown
- 1990-01-19 KR KR1019900000626A patent/KR920010642B1/ko not_active Expired
- 1990-01-19 DD DD90337216A patent/DD291559A5/de not_active IP Right Cessation
- 1990-01-19 NZ NZ232166A patent/NZ232166A/en unknown
- 1990-01-19 ZA ZA90393A patent/ZA90393B/xx unknown
- 1990-01-19 PL PL28784090A patent/PL287840A1/xx unknown
- 1990-01-19 YU YU9990A patent/YU47553B/sh unknown
1991
- 1991-07-22 NO NO91912860A patent/NO912860L/no unknown
- 1991-07-22 FI FI913509A patent/FI94641C/fi not_active IP Right Cessation
- 1991-09-20 US US07/763,081 patent/US5169947A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1990007926A1 (en)	1990-07-26
PL287840A1 (en)	1991-07-15
NZ232166A (en)	1992-10-28
YU9990A (en)	1992-05-28
MX19185A (es)	1993-12-01
ES2062319T3 (es)	1994-12-16
DK0379314T3 (da)	1994-05-09
IE900210L (en)	1990-07-23
US5169947A (en)	1992-12-08
PT92889A (pt)	1990-07-31
DE69007501T2 (de)	1994-06-30
AU613259B2 (en)	1991-07-25
NO912860D0 (no)	1991-07-22
JPH0751576B2 (ja)	1995-06-05
JPH02247175A (ja)	1990-10-02
CN1025998C (zh)	1994-09-28
FI94641B (fi)	1995-06-30
IL93041A0 (en)	1990-11-05
CA2008016A1 (en)	1990-07-20
ZA90393B (en)	1991-08-28
HUT57762A (en)	1991-12-30
CS26090A3 (en)	1992-02-19
PL283354A1 (en)	1991-08-12
US5051412A (en)	1991-09-24
DE69007501D1 (de)	1994-04-28
EP0379314B1 (de)	1994-03-23
EG18945A (en)	1994-09-29
KR900011772A (ko)	1990-08-02
FI94641C (fi)	1995-10-10
AU4867390A (en)	1990-07-26
CS277611B6 (en)	1993-03-17
DD298398A5 (de)	1992-02-20
NO912860L (no)	1991-07-22
PL163626B1 (pl)	1994-04-29
YU47553B (sh)	1995-10-03
FI913509A0 (fi)	1991-07-22
MY106305A (en)	1995-04-29
ATE103282T1 (de)	1994-04-15
IE62757B1 (en)	1995-02-22
DD291559A5 (de)	1991-07-04
CN1044465A (zh)	1990-08-08
HU206349B (en)	1992-10-28
EP0379314A1 (de)	1990-07-25
KR920010642B1 (ko)	1992-12-12

Legal Events

Date	Code	Title	Description
1996-10-31	RH	Patent void

Publication	Publication Date	Title
EP0379314B1 (de)	1994-03-23	3-(1,2,5,6-Tetrahydropyridyl)-pyrrolopyridine
DE60316542T2 (de)	2008-07-03	7-azaindole als inhibitoren c-jun n-terminaler kinasen zur behandlung neurodegenerativer störungen
JP4796698B2 (ja)	2011-10-19	新たな薬学的に活性な化合物
EP2041133B1 (de)	2010-10-13	Imidazo [1,2-a]pyridin-2-carboxamid-derivate, herstellungsverfahren und ihre verwendung für therapeutika
JP2010503627A (ja)	2010-02-04	心血管障害のためのグアニル酸シクラーゼの刺激剤としてのピラゾロピラジン、インダゾール、イミダゾピリジン、イミダゾピリミジン、ピラゾロピラジンおよびピラゾロピリジン誘導体
EA020409B1 (ru)	2014-10-30	Антагонисты рецептора cgrp
MXPA01010915A (es)	2002-11-07	Esteroides sustituidos con 3alfa-hidroxi-3beta mexoximetil- 21 -heterociclo, con actividad anestesica.
WO2007027999A2 (en)	2007-03-08	Chemical compounds
RU2093513C1 (ru)	1997-10-20	Производные 9-деазагуанины или их таутомеры и фармацевтическая композиция, обладающая способностью ингибировать активность пуриннуклеозид фосфорилазы у млекопитающих
IE58115B1 (en)	1993-07-14	New beta -carboline-3-oxadiazolyl derivatives,method of preparing the same and their use
EP1904501A2 (de)	2008-04-02	Chemische verbindungen
KR20010005676A (ko)	2001-01-15	테트라히드로피리도 화합물
CN111278814B (zh)	2022-10-28	作为毒蕈碱m1受体正向别构调节剂的多环酰胺
CA1264748A (en)	1990-01-23	.beta.-carboline-3-oxadiazolyl derivatives, method of preparing the same and_their use
JP3545332B2 (ja)	2004-07-21	新規カンプトテシン類似化合物、それらの製造方法、及びそれらを含有する医薬組成物
EA003991B1 (ru)	2003-12-25	Производные 2-аминопиридинов, способ ингибирования синтазы оксида азота, фармацевтические композиции и способы лечения
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HK1010051A1 (en)	1999-06-11	Ellipticine derivatives with antitumor activity
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FR2486801A1 (fr)	1982-01-22	Compositions pharmaceutiques a base de pyridoindoles
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