CA2567935C - Aminopyridine derivatives as selective dopamine d3 agonists - Google Patents

Aminopyridine derivatives as selective dopamine d3 agonists Download PDF

Info

Publication number: CA2567935C
Authority: CA; Canada
Prior art keywords: alkyl; formula; compounds; compound according; methyl
Prior art date: 2004-05-27
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

Application number

CA002567935A

Other languages

English (en)

French (fr)

Other versions

CA2567935A1 (en

Inventor

Charlotte Moira Norfor Allerton

Andrew Simon Cook

David Hepworth

Duncan Charles Miller

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

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

Pfizer Inc

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

2005-05-17

Publication date

2009-10-27

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=CA2567935(C) "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

2005-05-17 Application filed by Pfizer Corp SRL, Pfizer Inc filed Critical Pfizer Corp SRL

2005-12-08 Publication of CA2567935A1 publication Critical patent/CA2567935A1/en

2009-10-27 Application granted granted Critical

2009-10-27 Publication of CA2567935C publication Critical patent/CA2567935C/en

2025-05-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000556 agonist Substances 0.000 title abstract description 19
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title abstract description 10
150000003927 aminopyridines Chemical class 0.000 title description 9
229960003638 dopamine Drugs 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 370
238000011282 treatment Methods 0.000 claims abstract description 75
206010057671 Female sexual dysfunction Diseases 0.000 claims abstract description 23
201000001881 impotence Diseases 0.000 claims abstract description 19
208000010228 Erectile Dysfunction Diseases 0.000 claims abstract description 16
201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 16
231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims description 113
-1 OR7 Chemical group 0.000 claims description 84
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 30
239000003814 drug Substances 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
125000001424 substituent group Chemical group 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 26
125000001072 heteroaryl group Chemical group 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
230000004770 neurodegeneration Effects 0.000 claims description 11
208000020016 psychiatric disease Diseases 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 10
208000020401 Depressive disease Diseases 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
WZAQGEYBXLKEDB-UHFFFAOYSA-N 5-morpholin-2-ylpyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1OCCNC1 WZAQGEYBXLKEDB-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
239000000651 prodrug Substances 0.000 claims description 6
229940002612 prodrug Drugs 0.000 claims description 6
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 5
RPPCYSJLGJVJPM-OALUTQOASA-N 5-[(2r,5s)-5-(phenylmethoxymethyl)-4-propylmorpholin-2-yl]pyridin-2-amine Chemical compound C([C@H]1CO[C@@H](CN1CCC)C=1C=NC(N)=CC=1)OCC1=CC=CC=C1 RPPCYSJLGJVJPM-OALUTQOASA-N 0.000 claims description 5
WQEDAMLUPHXADE-WCQYABFASA-N 5-[(2s,5s)-4-butyl-5-methylmorpholin-2-yl]pyridin-2-amine Chemical compound O1C[C@H](C)N(CCCC)C[C@@H]1C1=CC=C(N)N=C1 WQEDAMLUPHXADE-WCQYABFASA-N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
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 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
DWSKCUWWSWFKJO-UHFFFAOYSA-N 4-methyl-5-(4-propylmorpholin-2-yl)pyridin-2-amine Chemical compound C1N(CCC)CCOC1C1=CN=C(N)C=C1C DWSKCUWWSWFKJO-UHFFFAOYSA-N 0.000 claims description 2
MILNIPPOWYGNRP-NWDGAFQWSA-N 5-[(2s,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-NWDGAFQWSA-N 0.000 claims description 2
PTLVHXZCCZEHPB-UHFFFAOYSA-N 5-[4-(3-phenylpropyl)morpholin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1OCCN(CCCC=2C=CC=CC=2)C1 PTLVHXZCCZEHPB-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
BWGDAGTZIVIBHX-MAUKXSAKSA-N 5-[(2s,5s)-5-methyl-4-(3-phenylpropyl)morpholin-2-yl]pyridin-2-amine Chemical compound C([C@@H](OC[C@@H]1C)C=2C=NC(N)=CC=2)N1CCCC1=CC=CC=C1 BWGDAGTZIVIBHX-MAUKXSAKSA-N 0.000 claims 1
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 1
208000021663 Female sexual arousal disease Diseases 0.000 abstract description 26
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
208000006262 Psychological Sexual Dysfunctions Diseases 0.000 abstract description 16
206010024419 Libido decreased Diseases 0.000 abstract description 13
208000035475 disorder Diseases 0.000 abstract description 13
208000017020 hypoactive sexual desire disease Diseases 0.000 abstract description 13
206010057672 Male sexual dysfunction Diseases 0.000 abstract description 5
208000014840 female orgasmic disease Diseases 0.000 abstract description 5
201000004197 inhibited female orgasm Diseases 0.000 abstract description 5
230000002265 prevention Effects 0.000 abstract description 5
208000015122 neurodegenerative disease Diseases 0.000 abstract description 4
239000003136 dopamine receptor stimulating agent Substances 0.000 abstract description 3
206010036596 premature ejaculation Diseases 0.000 abstract description 3
206010002652 Anorgasmia Diseases 0.000 abstract description 2
229940052760 dopamine agonists Drugs 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 276
238000006243 chemical reaction Methods 0.000 description 201
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 159
239000000203 mixture Substances 0.000 description 145
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
229910052739 hydrogen Inorganic materials 0.000 description 93
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 84
238000005481 NMR spectroscopy Methods 0.000 description 72
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
239000003921 oil Substances 0.000 description 69
235000019198 oils Nutrition 0.000 description 69
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 65
239000002904 solvent Substances 0.000 description 63
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
238000000034 method Methods 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000000741 silica gel Substances 0.000 description 47
229910002027 silica gel Inorganic materials 0.000 description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 43
239000000243 solution Substances 0.000 description 43
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 42
229910052943 magnesium sulfate Inorganic materials 0.000 description 42
235000019341 magnesium sulphate Nutrition 0.000 description 42
238000003818 flash chromatography Methods 0.000 description 41
235000019439 ethyl acetate Nutrition 0.000 description 40
238000010992 reflux Methods 0.000 description 40
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 35
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 34
239000002253 acid Substances 0.000 description 33
150000001408 amides Chemical class 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 32
239000007787 solid Substances 0.000 description 32
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
150000001299 aldehydes Chemical class 0.000 description 31
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 29
238000009472 formulation Methods 0.000 description 29
239000000543 intermediate Substances 0.000 description 28
150000002825 nitriles Chemical class 0.000 description 28
239000012442 inert solvent Substances 0.000 description 26
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
238000010511 deprotection reaction Methods 0.000 description 24
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 23
150000002009 diols Chemical class 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
239000003054 catalyst Substances 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
230000015572 biosynthetic process Effects 0.000 description 21
230000001568 sexual effect Effects 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
239000003795 chemical substances by application Substances 0.000 description 20
239000012044 organic layer Substances 0.000 description 19
238000003756 stirring 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
150000001412 amines Chemical class 0.000 description 18
238000001816 cooling Methods 0.000 description 18
239000012321 sodium triacetoxyborohydride Substances 0.000 description 18
239000003638 chemical reducing agent Substances 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
230000009467 reduction Effects 0.000 description 17
238000006722 reduction reaction Methods 0.000 description 17
150000001336 alkenes Chemical class 0.000 description 16
229910000085 borane Inorganic materials 0.000 description 16
229940079593 drug Drugs 0.000 description 16
150000002118 epoxides Chemical class 0.000 description 16
238000010438 heat treatment Methods 0.000 description 16
239000000463 material Substances 0.000 description 16
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239000003826 tablet Substances 0.000 description 16
230000000694 effects Effects 0.000 description 15
230000014759 maintenance of location Effects 0.000 description 15
239000000047 product Substances 0.000 description 15
239000010410 layer Substances 0.000 description 14
238000006268 reductive amination reaction Methods 0.000 description 13
239000012279 sodium borohydride Substances 0.000 description 13
229910000033 sodium borohydride Inorganic materials 0.000 description 13
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 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 12
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
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
230000037007 arousal Effects 0.000 description 12
229910052796 boron Inorganic materials 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000002552 dosage form Substances 0.000 description 12
210000004392 genitalia Anatomy 0.000 description 12
238000000746 purification Methods 0.000 description 12
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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
150000004678 hydrides Chemical class 0.000 description 11
229910052751 metal Inorganic materials 0.000 description 11
239000002184 metal Substances 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
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206010012289 Dementia Diseases 0.000 description 10
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239000003112 inhibitor Substances 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
239000007788 liquid Substances 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
229910000027 potassium carbonate Inorganic materials 0.000 description 10
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QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
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 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
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150000003222 pyridines Chemical class 0.000 description 9
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 8
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239000012298 atmosphere Substances 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000001257 hydrogen Substances 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
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150000003141 primary amines Chemical class 0.000 description 8
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
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239000005557 antagonist Substances 0.000 description 7
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
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150000004820 halides Chemical class 0.000 description 7
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
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230000002618 waking effect Effects 0.000 description 1
229960005080 warfarin Drugs 0.000 description 1
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229960000317 yohimbine Drugs 0.000 description 1
BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

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- 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
- C07D213/73—Unsubstituted amino or imino radicals
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Obesity (AREA)
Hematology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Gynecology & Obstetrics (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Child & Adolescent Psychology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Emergency Medicine (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002567935A 2004-05-27 2005-05-17 Aminopyridine derivatives as selective dopamine d3 agonists Expired - Fee Related CA2567935C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB0411891A GB0411891D0 (en)	2004-05-27	2004-05-27	New aminopyridine derivatives and their use as pharmaceuticals
GB0411891.5		2004-05-27
GB0412463.2		2004-06-03
GB0412463A GB0412463D0 (en)	2004-06-03	2004-06-03	New aminopyridine derivatives and their use as pharmaceuticals
PCT/IB2005/001554 WO2005115985A1 (en)	2004-05-27	2005-05-17	Aminopyridine derivatives as selective dopamine d3 agonists

Publications (2)

Publication Number	Publication Date
CA2567935A1 CA2567935A1 (en)	2005-12-08
CA2567935C true CA2567935C (en)	2009-10-27

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Application Number	Title	Priority Date	Filing Date
CA002567935A Expired - Fee Related CA2567935C (en)	2004-05-27	2005-05-17	Aminopyridine derivatives as selective dopamine d3 agonists

Country Status (21)

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

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GB0502509D0 (en) *	2005-02-07	2005-03-16	Pfizer Ltd	Novel salt form of a dopamine agonist
CA2752105C (en) *	2009-02-13	2017-10-31	Matthias Vennemann	Fused pyrimidines
EP2558437B1 (en) *	2010-04-12	2015-08-05	Supernus Pharmaceuticals, Inc.	Methods for producing viloxazine salts and novel polymorphs thereof
US9504949B2 (en)	2011-06-30	2016-11-29	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
HRP20241015T1 (hr)	2016-07-20	2024-11-08	Novartis Ag	Derivati aminopiridina i njihova uporaba kao selektivnih alk-2 inhibitora
IL274868B2 (en) *	2017-12-08	2024-06-01	Boehringer Ingelheim Int	History of imidazopyridine and their use as medicine
US12479838B2 (en) *	2019-04-12	2025-11-25	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
MX2022006176A (es)	2019-11-22	2022-08-17	Incyte Corp	Terapia combinada que comprende un inhibidor de alk2 y un inhibidor de jak2.
PH12022553501A1 (en)	2020-06-16	2024-04-22	Incyte Corp	Alk2 inhibitors for the treatment of anemia

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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
NZ540505A (en) *	2002-12-10	2007-02-23	Pfizer	Morpholine derivatives for use as dopamine agonists in the treatment of I.A. sexual dysfunction

2005
- 2005-05-17 CA CA002567935A patent/CA2567935C/en not_active Expired - Fee Related
- 2005-05-17 JP JP2007514200A patent/JP4198183B2/ja not_active Expired - Fee Related
- 2005-05-17 AU AU2005247699A patent/AU2005247699A1/en not_active Abandoned
- 2005-05-17 EA EA200601982A patent/EA200601982A1/ru unknown
- 2005-05-17 AP AP2006003824A patent/AP2006003824A0/xx unknown
- 2005-05-17 BR BRPI0511571-0A patent/BRPI0511571A/pt not_active Application Discontinuation
- 2005-05-17 MX MXPA06013786A patent/MXPA06013786A/es not_active Application Discontinuation
- 2005-05-17 WO PCT/IB2005/001554 patent/WO2005115985A1/en not_active Ceased
- 2005-05-17 EP EP05747191A patent/EP1758862A1/en not_active Withdrawn
- 2005-05-24 GT GT200500125A patent/GT200500125A/es unknown
- 2005-05-25 PE PE2005000583A patent/PE20060366A1/es not_active Application Discontinuation
- 2005-05-26 NL NL1029139A patent/NL1029139C2/nl not_active IP Right Cessation
- 2005-05-26 PA PA20058635101A patent/PA8635101A1/es unknown
- 2005-05-26 AR ARP050102169A patent/AR049548A1/es unknown
- 2005-05-26 UY UY28925A patent/UY28925A1/es not_active Application Discontinuation
- 2005-05-26 TW TW094117274A patent/TW200609216A/zh unknown
- 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
UY28925A1 (es)	2005-12-30
AU2005247699A1 (en)	2005-12-08
GT200500125A (es)	2006-01-10
NO20065326L (no)	2006-12-19
PA8635101A1 (es)	2006-05-16
JP4198183B2 (ja)	2008-12-17
WO2005115985A1 (en)	2005-12-08
BRPI0511571A (pt)	2008-01-02
JP2008500331A (ja)	2008-01-10
AP2006003824A0 (en)	2006-12-31
AR049548A1 (es)	2006-08-16
ECSP067029A (es)	2006-12-29
EP1758862A1 (en)	2007-03-07
IL179314A0 (en)	2007-03-08
CA2567935A1 (en)	2005-12-08
PE20060366A1 (es)	2006-05-15
TW200609216A (en)	2006-03-16
MA28607B1 (fr)	2007-05-02
MXPA06013786A (es)	2007-01-25
NL1029139C2 (nl)	2006-06-19
SV2005002129A (es)	2005-12-13
EA200601982A1 (ru)	2007-04-27
NL1029139A1 (nl)	2005-11-30

Publication	Publication Date	Title
JP5780954B2 (ja)	2015-09-16	ヒスタミンｈ３受容体アンタゴニストとしてのアゼチジン類及びシクロブタン類
US20090005354A1 (en)	2009-01-01	New Amino Derivatives and Their Use as Pharmaceuticals
CN101959870A (zh)	2011-01-26	吗啉衍生物的制备
CN101679357A (zh)	2010-03-24	取代的杂环衍生物及其组合物和作为抗菌剂的药物用途
CA2567935C (en)	2009-10-27	Aminopyridine derivatives as selective dopamine d3 agonists
US20050176772A1 (en)	2005-08-11	Pharmaceutically active compounds
US20050267096A1 (en)	2005-12-01	New indazole and indolone derivatives and their use pharmaceuticals
JP2020522504A (ja)	2020-07-30	多環式化合物およびそれらの用途
CA2702745A1 (en)	2009-04-23	Trisubstituted piperidines
EP1753763B1 (en)	2008-08-13	Indazole and indolone derivatives and their use as pharmaceuticals
MXPA01008860A (es)	2002-08-20	Derivados de fenoxifenilheterociclilo como inhibidores selectivos de la recaptacion de serotonina.
KR20070022795A (ko)	2007-02-27	선택적 도파민 ｄ3 효능제로서의 아미노피리딘 유도체
KR20070022753A (ko)	2007-02-27	인다졸 및 인돌론 유도체 및 이의 약제로서의 용도
CA2758367A1 (fr)	2010-10-21	Derives de n-[(7-aza-bicyclo[2.2.1]hept-1-yl)-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique
CN1956958A (zh)	2007-05-02	作为选择性多巴胺d3激动剂的氨基吡啶衍生物
CA2751863A1 (fr)	2010-08-19	Derives de n-[(2-aza-bicyclo[2.1.1]hex-1-yl]-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique
HK1104029A (en)	2008-01-04	Aminopyridine derivatives as selective dopamine d3 agonists
CA2751866A1 (fr)	2010-08-19	Derives de n-[(6-aza-bicyclo[3.2.1]oct-1-yl)-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique
CA2755526A1 (fr)	2010-09-23	Derives de n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, leur preparation et leur application en therapeutique
FR2943056A1 (fr)	2010-09-17	Derives de n-°2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique
FR2944283A1 (fr)	2010-10-15	Derives de n-°(2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique

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2006-11-23	EEER	Examination request
2012-05-17	MKLA	Lapsed