NL1029139C2 - Nieuwe aminopyridinederivaten en hun gebruik als farmaceutica. - Google Patents

Nieuwe aminopyridinederivaten en hun gebruik als farmaceutica. Download PDF

Info

Publication number: NL1029139C2
Authority: NL; Netherlands
Prior art keywords: alkyl; formula; compounds; methyl; mmol
Prior art date: 2004-05-27

Application number

NL1029139A

Other languages

English (en)

Dutch (nl)

Other versions

NL1029139A1 (nl

Inventor

David Hepworth

Duncan Charles Miller

Charlotte Moira Norfo Allerton

Andrew Simon Cook

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.)

2004-05-27

Filing date

2005-05-26

Publication date

2006-06-19

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34970000&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NL1029139(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-05-27 Priority claimed from GB0411891A external-priority patent/GB0411891D0/en

2004-06-03 Priority claimed from GB0412463A external-priority patent/GB0412463D0/en

2005-05-26 Application filed by Pfizer filed Critical Pfizer

2005-11-30 Publication of NL1029139A1 publication Critical patent/NL1029139A1/nl

2006-06-19 Application granted granted Critical

2006-06-19 Publication of NL1029139C2 publication Critical patent/NL1029139C2/nl

Links

239000003814 drug Substances 0.000 title claims description 29
150000003927 aminopyridines Chemical class 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 350
238000002360 preparation method Methods 0.000 claims description 136
-1 4-propyl-morpholin-2-yl Chemical group 0.000 claims description 114
238000011282 treatment Methods 0.000 claims description 79
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 18
206010057671 Female sexual dysfunction Diseases 0.000 claims description 17
201000001881 impotence Diseases 0.000 claims description 16
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
208000010228 Erectile Dysfunction Diseases 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
201000001880 Sexual dysfunction Diseases 0.000 claims description 9
231100000872 sexual dysfunction Toxicity 0.000 claims description 9
208000020401 Depressive disease Diseases 0.000 claims description 8
230000004770 neurodegeneration Effects 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
208000020016 psychiatric disease Diseases 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000012453 solvate Substances 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000000651 prodrug Substances 0.000 claims description 4
229940002612 prodrug Drugs 0.000 claims description 4
UXRVFSIWSWPXSI-CBAPKCEASA-N 5-[(2r,5s)-5-methylmorpholin-2-yl]pyridin-2-amine Chemical compound C1N[C@@H](C)CO[C@@H]1C1=CC=C(N)N=C1 UXRVFSIWSWPXSI-CBAPKCEASA-N 0.000 claims description 3
GDJIKWMLGQXLIT-UHFFFAOYSA-N [6-(6-aminopyridin-3-yl)-4-propylmorpholin-3-yl]methanol Chemical compound O1CC(CO)N(CCC)CC1C1=CC=C(N)N=C1 GDJIKWMLGQXLIT-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
MILNIPPOWYGNRP-RYUDHWBXSA-N 5-[(2r,5s)-4,5-diethylmorpholin-2-yl]pyridin-2-amine Chemical compound C1N(CC)[C@@H](CC)CO[C@@H]1C1=CC=C(N)N=C1 MILNIPPOWYGNRP-RYUDHWBXSA-N 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 297
238000006243 chemical reaction Methods 0.000 description 202
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
229910052739 hydrogen Inorganic materials 0.000 description 185
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 145
239000000203 mixture Substances 0.000 description 136
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 107
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 104
239000003921 oil Substances 0.000 description 68
235000019198 oils Nutrition 0.000 description 68
238000005481 NMR spectroscopy Methods 0.000 description 64
239000002904 solvent Substances 0.000 description 64
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
238000000034 method Methods 0.000 description 58
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000000741 silica gel Substances 0.000 description 50
229910002027 silica gel Inorganic materials 0.000 description 50
239000000460 chlorine Substances 0.000 description 47
239000000243 solution Substances 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
238000003818 flash chromatography Methods 0.000 description 45
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
239000011541 reaction mixture Substances 0.000 description 44
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 42
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 40
235000019439 ethyl acetate Nutrition 0.000 description 40
239000002253 acid Substances 0.000 description 39
238000010992 reflux Methods 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
102100027006 Paraplegin Human genes 0.000 description 34
150000001299 aldehydes Chemical class 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 32
150000001408 amides Chemical class 0.000 description 32
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
239000007787 solid Substances 0.000 description 31
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 27
229910000041 hydrogen chloride Inorganic materials 0.000 description 27
230000015572 biosynthetic process Effects 0.000 description 26
239000012442 inert solvent Substances 0.000 description 26
239000000543 intermediate Substances 0.000 description 26
150000002825 nitriles Chemical class 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
150000002009 diols Chemical class 0.000 description 24
208000021663 Female sexual arousal disease Diseases 0.000 description 23
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 23
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
239000003054 catalyst Substances 0.000 description 22
208000035475 disorder Diseases 0.000 description 22
239000010410 layer Substances 0.000 description 22
230000001568 sexual effect Effects 0.000 description 22
239000000556 agonist Substances 0.000 description 21
150000001412 amines Chemical class 0.000 description 21
239000007788 liquid Substances 0.000 description 21
239000003795 chemical substances by application Substances 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
239000012044 organic layer Substances 0.000 description 20
238000010511 deprotection reaction Methods 0.000 description 19
PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
150000001414 amino alcohols Chemical class 0.000 description 18
238000001816 cooling Methods 0.000 description 18
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
239000000463 material Substances 0.000 description 18
150000003335 secondary amines Chemical class 0.000 description 18
239000003638 chemical reducing agent Substances 0.000 description 17
150000002924 oxiranes Chemical class 0.000 description 17
125000006239 protecting group Chemical group 0.000 description 17
239000012321 sodium triacetoxyborohydride Substances 0.000 description 17
239000003826 tablet Substances 0.000 description 17
150000001336 alkenes Chemical class 0.000 description 16
238000010438 heat treatment Methods 0.000 description 16
230000014759 maintenance of location Effects 0.000 description 16
230000009467 reduction Effects 0.000 description 16
238000006722 reduction reaction Methods 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 14
229910000085 borane Inorganic materials 0.000 description 14
239000000047 product Substances 0.000 description 14
230000002829 reductive effect Effects 0.000 description 14
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 13
229940079593 drug Drugs 0.000 description 13
230000000694 effects Effects 0.000 description 13
230000004044 response Effects 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000002552 dosage form Substances 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 12
238000000746 purification Methods 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
206010012289 Dementia Diseases 0.000 description 11
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 11
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
239000005557 antagonist Substances 0.000 description 11
238000005553 drilling Methods 0.000 description 11
210000004392 genitalia Anatomy 0.000 description 11
150000004678 hydrides Chemical class 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
206010024419 Libido decreased Diseases 0.000 description 10
208000017020 hypoactive sexual desire disease Diseases 0.000 description 10
VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 description 10
239000012280 lithium aluminium hydride Substances 0.000 description 10
VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
239000012279 sodium borohydride Substances 0.000 description 10
229910000033 sodium borohydride Inorganic materials 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
125000002524 organometallic group Chemical group 0.000 description 9
210000003899 penis Anatomy 0.000 description 9
239000000843 powder Substances 0.000 description 9
150000003222 pyridines Chemical class 0.000 description 9
238000006268 reductive amination reaction Methods 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 8
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 8
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
230000037007 arousal Effects 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
150000004677 hydrates Chemical class 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
238000006798 ring closing metathesis reaction Methods 0.000 description 8
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
210000002460 smooth muscle Anatomy 0.000 description 8
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
208000019901 Anxiety disease Diseases 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 7
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
208000028017 Psychotic disease Diseases 0.000 description 7
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
210000005226 corpus cavernosum Anatomy 0.000 description 7
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229940011871 estrogen Drugs 0.000 description 7
239000000262 estrogen Substances 0.000 description 7
239000010408 film Substances 0.000 description 7
230000014509 gene expression Effects 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
150000003141 primary amines Chemical class 0.000 description 7
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
210000001215 vagina Anatomy 0.000 description 7
239000011701 zinc Substances 0.000 description 7
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 description 6
230000001476 alcoholic effect Effects 0.000 description 6
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 6
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
230000003111 delayed effect Effects 0.000 description 6
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Gynecology & Obstetrics (AREA)
Psychology (AREA)
Urology & Nephrology (AREA)
Rheumatology (AREA)
Emergency Medicine (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)
Child & Adolescent Psychology (AREA)
Vascular Medicine (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL1029139A 2004-05-27 2005-05-26 Nieuwe aminopyridinederivaten en hun gebruik als farmaceutica. NL1029139C2 (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB0411891		2004-05-27
GB0411891A GB0411891D0 (en)	2004-05-27	2004-05-27	New aminopyridine derivatives and their use as pharmaceuticals
GB0412463		2004-06-03
GB0412463A GB0412463D0 (en)	2004-06-03	2004-06-03	New aminopyridine derivatives and their use as pharmaceuticals

Publications (2)

Publication Number	Publication Date
NL1029139A1 NL1029139A1 (nl)	2005-11-30
NL1029139C2 true NL1029139C2 (nl)	2006-06-19

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NL1029139A NL1029139C2 (nl)	2004-05-27	2005-05-26	Nieuwe aminopyridinederivaten en hun gebruik als farmaceutica.

Country Status (21)

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EP (1)	EP1758862A1 (pt)
JP (1)	JP4198183B2 (pt)
AP (1)	AP2006003824A0 (pt)
AR (1)	AR049548A1 (pt)
AU (1)	AU2005247699A1 (pt)
BR (1)	BRPI0511571A (pt)
CA (1)	CA2567935C (pt)
EA (1)	EA200601982A1 (pt)
EC (1)	ECSP067029A (pt)
GT (1)	GT200500125A (pt)
IL (1)	IL179314A0 (pt)
MA (1)	MA28607B1 (pt)
MX (1)	MXPA06013786A (pt)
NL (1)	NL1029139C2 (pt)
NO (1)	NO20065326L (pt)
PA (1)	PA8635101A1 (pt)
PE (1)	PE20060366A1 (pt)
SV (1)	SV2005002129A (pt)
TW (1)	TW200609216A (pt)
UY (1)	UY28925A1 (pt)
WO (1)	WO2005115985A1 (pt)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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GB0502509D0 (en) *	2005-02-07	2005-03-16	Pfizer Ltd	Novel salt form of a dopamine agonist
EA201101186A1 (ru)	2009-02-13	2012-04-30	Байер Фарма Акциенгезельшафт	Конденсированные пиримидины
EP2558437B1 (en) *	2010-04-12	2015-08-05	Supernus Pharmaceuticals, Inc.	Methods for producing viloxazine salts and novel polymorphs thereof
WO2013003769A2 (en)	2011-06-30	2013-01-03	Donaldson Company, Inc.	Air/oil separator assemblies; components; and, methods
GB2543296A (en)	2015-10-13	2017-04-19	Indivior Uk Ltd	Dopamine D3 receptor antagonists having a morpholine moiety
MX388518B (es)	2016-07-20	2025-03-19	Novartis Ag	Derivados de aminopiridina y su uso como inhibidores selectivos de alk-2.
WO2019110703A1 (en) *	2017-12-08	2019-06-13	Boehringer Ingelheim International Gmbh	Imidazopyridine derivatives and the use thereof as medicament
CA3136151A1 (en) *	2019-04-12	2020-10-15	The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	D3 receptor agonist compounds; methods of preparation; intermediates thereof; and methods of use thereof
JP7717065B2 (ja)	2019-11-22	2025-08-01	インサイトコーポレーション	Ａｌｋ２阻害剤及びｊａｋ２阻害剤を含む併用療法
WO2021257532A1 (en)	2020-06-16	2021-12-23	Incyte Corporation	Alk2 inhibitors for the treatment of anemia

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* Cited by examiner, † Cited by third party
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US5077290A (en) *	1990-10-11	1991-12-31	Merck & Co., Inc.	Morpholine derivatives compositions and use
GB0130219D0 (en) *	2001-12-18	2002-02-06	Pfizer Ltd	Compounds for the treatment of sexual dysfunction
OA13014A (en) *	2002-12-10	2006-11-10	Pfizer	Morpholine derivatives for use as dopamine agonists in the treatment of i.a sexual dysfunction.

2005
- 2005-05-17 AU AU2005247699A patent/AU2005247699A1/en not_active Abandoned
- 2005-05-17 MX MXPA06013786A patent/MXPA06013786A/es not_active Application Discontinuation
- 2005-05-17 BR BRPI0511571-0A patent/BRPI0511571A/pt not_active Application Discontinuation
- 2005-05-17 AP AP2006003824A patent/AP2006003824A0/xx unknown
- 2005-05-17 EP EP05747191A patent/EP1758862A1/en not_active Withdrawn
- 2005-05-17 JP JP2007514200A patent/JP4198183B2/ja not_active Expired - Fee Related
- 2005-05-17 WO PCT/IB2005/001554 patent/WO2005115985A1/en not_active Ceased
- 2005-05-17 EA EA200601982A patent/EA200601982A1/ru unknown
- 2005-05-17 CA CA002567935A patent/CA2567935C/en not_active Expired - Fee Related
- 2005-05-24 GT GT200500125A patent/GT200500125A/es unknown
- 2005-05-25 PE PE2005000583A patent/PE20060366A1/es not_active Application Discontinuation
- 2005-05-26 PA PA20058635101A patent/PA8635101A1/es unknown
- 2005-05-26 NL NL1029139A patent/NL1029139C2/nl not_active IP Right Cessation
- 2005-05-26 AR ARP050102169A patent/AR049548A1/es unknown
- 2005-05-26 TW TW094117274A patent/TW200609216A/zh unknown
- 2005-05-26 UY UY28925A patent/UY28925A1/es not_active Application Discontinuation
- 2005-05-27 SV SV2005002129A patent/SV2005002129A/es not_active Application Discontinuation
2006
- 2006-11-15 IL IL179314A patent/IL179314A0/en unknown
- 2006-11-20 NO NO20065326A patent/NO20065326L/no unknown
- 2006-11-27 MA MA29488A patent/MA28607B1/fr unknown
- 2006-11-27 EC EC2006007029A patent/ECSP067029A/es unknown

Also Published As

Publication number	Publication date
NL1029139A1 (nl)	2005-11-30
SV2005002129A (es)	2005-12-13
MXPA06013786A (es)	2007-01-25
BRPI0511571A (pt)	2008-01-02
CA2567935C (en)	2009-10-27
TW200609216A (en)	2006-03-16
UY28925A1 (es)	2005-12-30
ECSP067029A (es)	2006-12-29
PA8635101A1 (es)	2006-05-16
EP1758862A1 (en)	2007-03-07
NO20065326L (no)	2006-12-19
AR049548A1 (es)	2006-08-16
IL179314A0 (en)	2007-03-08
MA28607B1 (fr)	2007-05-02
JP2008500331A (ja)	2008-01-10
EA200601982A1 (ru)	2007-04-27
GT200500125A (es)	2006-01-10
PE20060366A1 (es)	2006-05-15
AU2005247699A1 (en)	2005-12-08
WO2005115985A1 (en)	2005-12-08
AP2006003824A0 (en)	2006-12-31
JP4198183B2 (ja)	2008-12-17
CA2567935A1 (en)	2005-12-08

Legal Events

Date	Code	Title	Description
2006-02-01	AD1A	A request for search or an international type search has been filed
2006-04-03	RD2N	Patents in respect of which a decision has been taken or a report has been made (novelty report)	Effective date: 20060210
2006-08-01	PD2B	A search report has been drawn up
2010-02-01	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20091201

Publication	Publication Date	Title
JP3245424B2 (ja)	2002-01-15	モルホリンおよびチオモルホリン系のタキキニン受容体拮抗薬
US20170342054A1 (en)	2017-11-30	Compounds and methods of use thereof
HK1210609A1 (en)	2016-04-29	Fluoro-[1,3]oxazines as bace1 inhibitors
JPH09509935A (ja)	1997-10-07	モルホリンタキキニン受容体拮抗薬のプロドラッグ
US20090005354A1 (en)	2009-01-01	New Amino Derivatives and Their Use as Pharmaceuticals
CN102300863A (zh)	2011-12-28	具有乙基和乙烯基连接体的异*唑/邻-吡啶衍生物
US20220281823A1 (en)	2022-09-08	PHENYL AND PYRIDINYL SUBSTITUTED IMIDAZOLES AS MODULATORS OF RORgT
US20210093606A1 (en)	2021-04-01	Compounds and uses thereof
NL1029139C2 (nl)	2006-06-19	Nieuwe aminopyridinederivaten en hun gebruik als farmaceutica.
JP2010064982A (ja)	2010-03-25	アルキルアミノ誘導体
NL1024983C2 (nl)	2005-02-01	Morfine als dopamineagonisten.
OA13039A (en)	2006-11-10	3-(1-[3-(1,3-benzothiazol-6-yl)propylcarbamoyl]cycloalkyl)propanoic acid derivatives as NEP inhibitors.
JP2023503320A (ja)	2023-01-27	肝臓ｘ受容体アゴニストとしての１，２，４－オキサジアゾール誘導体
JP2008543828A (ja)	2008-12-04	ドーパミン作動薬としての３−フェニルアゼチジン誘導体
US20050267096A1 (en)	2005-12-01	New indazole and indolone derivatives and their use pharmaceuticals
KR100997033B1 (ko)	2010-11-26	도파민 아고니스트의 신규한 염 형태
JP2009532443A (ja)	2009-09-10	レニンインヒビターとして用いるための置換４−フェニルピペリジン
CA2995161A1 (en)	2017-03-30	2,3,4,5-tetrahydropyridin-6-amine derivatives
EP1753763B1 (en)	2008-08-13	Indazole and indolone derivatives and their use as pharmaceuticals
KR20070022795A (ko)	2007-02-27	선택적 도파민 ｄ3 효능제로서의 아미노피리딘 유도체
KR20070022753A (ko)	2007-02-27	인다졸 및 인돌론 유도체 및 이의 약제로서의 용도
JP2008521789A (ja)	2008-06-26	クロマン化合物
NZ718251B2 (en)	2021-05-27	Piperazine derivatives and the use thereof as medicament
HK1104029A (en)	2008-01-04	Aminopyridine derivatives as selective dopamine d3 agonists
JP2014088325A (ja)	2014-05-15	グリシントランスポーター阻害物質