CA2657986A1 - Composes de piperazine substitues - Google Patents
Composes de piperazine substitues Download PDFInfo
- Publication number
- CA2657986A1 CA2657986A1 CA002657986A CA2657986A CA2657986A1 CA 2657986 A1 CA2657986 A1 CA 2657986A1 CA 002657986 A CA002657986 A CA 002657986A CA 2657986 A CA2657986 A CA 2657986A CA 2657986 A1 CA2657986 A1 CA 2657986A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- hydrogen
- aryl
- halo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000004885 piperazines Chemical class 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 265
- 125000000217 alkyl group Chemical group 0.000 claims description 264
- 229910052739 hydrogen Inorganic materials 0.000 claims description 195
- 125000003118 aryl group Chemical group 0.000 claims description 189
- 239000001257 hydrogen Substances 0.000 claims description 177
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 109
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 107
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 88
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
- -1 piperazine compound Chemical class 0.000 claims description 71
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 43
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004193 piperazinyl group Chemical group 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- BKAJGWKYAUKWQR-UHFFFAOYSA-N 2-[4-[3-(2,3-dihydro-1h-inden-2-yloxy)-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COC2CC3=CC=CC=C3C2)CC1 BKAJGWKYAUKWQR-UHFFFAOYSA-N 0.000 claims description 6
- JOUDVTKERAVYBD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-hydroxy-3-phenylpropyl)piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CC=2C=CC=CC=2)CC1 JOUDVTKERAVYBD-UHFFFAOYSA-N 0.000 claims description 6
- FJODUEWDUANLOM-UHFFFAOYSA-N 2-[4-[3-[(2,4-dimethoxyphenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound COC1=CC(OC)=CC=C1COCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 FJODUEWDUANLOM-UHFFFAOYSA-N 0.000 claims description 5
- AOIRORRGHYXXFR-UHFFFAOYSA-N 2-[4-[3-[(4-butylphenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound C1=CC(CCCC)=CC=C1COCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 AOIRORRGHYXXFR-UHFFFAOYSA-N 0.000 claims description 5
- JFPXSSAVFKWSLG-UHFFFAOYSA-N 2-[4-[3-[(4-tert-butylphenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C=CC(=CC=2)C(C)(C)C)CC1 JFPXSSAVFKWSLG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- JJWJIKXTQILDPC-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenyl)propyl]piperazin-1-yl]acetamide Chemical compound COC1=CC=CC=C1CC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 JJWJIKXTQILDPC-UHFFFAOYSA-N 0.000 claims description 5
- VXYMFYCMJSJDNP-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-[(4-phenylphenyl)methoxy]propyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 VXYMFYCMJSJDNP-UHFFFAOYSA-N 0.000 claims description 5
- FWVPICHMUMFOOI-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[3-[(4-fluorophenyl)methoxy]-2-hydroxypropyl]-3,3-dimethylpiperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CC(C)(C)N(CC(O)COCC=2C=CC(F)=CC=2)CC1 FWVPICHMUMFOOI-UHFFFAOYSA-N 0.000 claims description 5
- HBODICVFHNSMEK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-hydroxy-3-phenylmethoxypropyl)piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C=CC=CC=2)CC1 HBODICVFHNSMEK-UHFFFAOYSA-N 0.000 claims description 4
- ULANQYGGIAFRCT-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-hydroxy-5-phenylpentyl)piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCCC=2C=CC=CC=2)CC1 ULANQYGGIAFRCT-UHFFFAOYSA-N 0.000 claims description 4
- LJVLIXKTLFKLHA-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-[(2-methoxyphenyl)methoxy]propyl]piperazin-1-yl]acetamide Chemical compound COC1=CC=CC=C1COCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 LJVLIXKTLFKLHA-UHFFFAOYSA-N 0.000 claims description 4
- KHMWCPCPKKBWCS-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-[[4-(trifluoromethyl)phenyl]methoxy]propyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C=CC(=CC=2)C(F)(F)F)CC1 KHMWCPCPKKBWCS-UHFFFAOYSA-N 0.000 claims description 4
- PHBGQKPZVMEJGV-UHFFFAOYSA-N 2-[4-[4-(2,6-difluorophenyl)-2-hydroxybutyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C(=CC=CC=2F)F)CC1 PHBGQKPZVMEJGV-UHFFFAOYSA-N 0.000 claims description 3
- JOWHVDLGWCPULX-UHFFFAOYSA-N 2-[4-[4-(2-chlorophenyl)-2-hydroxybutyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C(=CC=CC=2)Cl)CC1 JOWHVDLGWCPULX-UHFFFAOYSA-N 0.000 claims description 3
- YOJWTCTTZGSASM-UHFFFAOYSA-N 2-[4-[4-(4-tert-butylphenyl)-2-hydroxybutyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C=CC(=CC=2)C(C)(C)C)CC1 YOJWTCTTZGSASM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UVMSIUBSCUQUHE-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-hydroxy-4-phenylbutyl)piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C=CC=CC=2)CC1 UVMSIUBSCUQUHE-UHFFFAOYSA-N 0.000 claims description 3
- LWJBEPPWKAJEPU-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-4-[4-(trifluoromethyl)phenyl]butyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C=CC(=CC=2)C(F)(F)F)CC1 LWJBEPPWKAJEPU-UHFFFAOYSA-N 0.000 claims description 3
- MWJOQGPEMBCMDO-UHFFFAOYSA-N 2-[4-[3-(cyclohexylmethoxy)-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC2CCCCC2)CC1 MWJOQGPEMBCMDO-UHFFFAOYSA-N 0.000 claims description 2
- XOBDSFVYEWDDRT-UHFFFAOYSA-N 2-[4-[3-[(2,4-difluorophenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C(=CC(F)=CC=2)F)CC1 XOBDSFVYEWDDRT-UHFFFAOYSA-N 0.000 claims description 2
- MUVONNRBPZCXSV-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(4-methoxyphenyl)propyl]piperazin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 MUVONNRBPZCXSV-UHFFFAOYSA-N 0.000 claims description 2
- GQSCUSHSWKYEHJ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-[(4-methylphenyl)methoxy]propyl]piperazin-1-yl]acetamide Chemical compound C1=CC(C)=CC=C1COCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 GQSCUSHSWKYEHJ-UHFFFAOYSA-N 0.000 claims description 2
- NWENZKGHGGBLQY-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-4-(4-methoxyphenyl)butyl]piperazin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 NWENZKGHGGBLQY-UHFFFAOYSA-N 0.000 claims description 2
- CBBLOVBXHDNIEQ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[3-[(2-fluorophenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C(=CC=CC=2)F)CC1 CBBLOVBXHDNIEQ-UHFFFAOYSA-N 0.000 claims description 2
- PCZZGELDPPLUBD-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[3-[(4-fluorophenyl)methoxy]-2-hydroxypropyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)COCC=2C=CC(F)=CC=2)CC1 PCZZGELDPPLUBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 71
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 7
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- KLLMJLAAAIBZEB-UHFFFAOYSA-N 2-[4-[5-(2-chlorophenyl)-2-hydroxypentyl]piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCCC=2C(=CC=CC=2)Cl)CC1 KLLMJLAAAIBZEB-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 1
- RXDLSAZWTNBZMQ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(2-hydroxy-3-phenylpropyl)piperazin-1-yl]-2-methylpropanamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C(C)(C)N1CCN(CC(O)CC=2C=CC=CC=2)CC1 RXDLSAZWTNBZMQ-UHFFFAOYSA-N 0.000 claims 1
- LNMWLEPNCPZUOB-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl]piperazin-1-yl]-2-methylpropanamide Chemical compound COC1=C(OC)C(OC)=CC(CC(O)CN2CCN(CC2)C(C)(C)C(=O)NC=2C(=CC=CC=2C)C)=C1 LNMWLEPNCPZUOB-UHFFFAOYSA-N 0.000 claims 1
- MZYZVZZTRHATIY-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-[(4-methoxyphenyl)methoxy]propyl]piperazin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1COCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 MZYZVZZTRHATIY-UHFFFAOYSA-N 0.000 claims 1
- FSRZECAWVGSGIT-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[4-(2-fluorophenyl)-2-hydroxybutyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCC=2C(=CC=CC=2)F)CC1 FSRZECAWVGSGIT-UHFFFAOYSA-N 0.000 claims 1
- PUPYNLUYKZFTQU-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[5-(2-fluorophenyl)-2-hydroxypentyl]piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CCCC=2C(=CC=CC=2)F)CC1 PUPYNLUYKZFTQU-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 14
- 201000010099 disease Diseases 0.000 abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
- 210000002027 skeletal muscle Anatomy 0.000 abstract description 13
- 150000003839 salts Chemical class 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 8
- 208000010125 myocardial infarction Diseases 0.000 abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
- 230000009885 systemic effect Effects 0.000 abstract description 7
- 210000001519 tissue Anatomy 0.000 abstract description 7
- 206010003130 Arrhythmia supraventricular Diseases 0.000 abstract description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 abstract description 6
- 206010022562 Intermittent claudication Diseases 0.000 abstract description 6
- 208000007718 Stable Angina Diseases 0.000 abstract description 6
- 206010047281 Ventricular arrhythmia Diseases 0.000 abstract description 6
- 230000001746 atrial effect Effects 0.000 abstract description 6
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- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
- 125000005843 halogen group Chemical group 0.000 description 67
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- XKLMZUWKNUAPSZ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide Chemical compound COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-UHFFFAOYSA-N 0.000 description 20
- 238000001819 mass spectrum Methods 0.000 description 20
- 229960000213 ranolazine Drugs 0.000 description 20
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 150000002118 epoxides Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000004414 alkyl thio group Chemical group 0.000 description 13
- 125000004104 aryloxy group Chemical group 0.000 description 13
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- 230000009467 reduction Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 description 11
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 10
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- 229910052736 halogen Inorganic materials 0.000 description 10
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- 239000002585 base Substances 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 241000124008 Mammalia Species 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 229940126214 compound 3 Drugs 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 210000004185 liver Anatomy 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 6
- ZKODPGZNBMIZFX-UHFFFAOYSA-N 2-(2-bromoethyl)oxirane Chemical compound BrCCC1CO1 ZKODPGZNBMIZFX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
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- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CHFDHHMRZRLEJD-UHFFFAOYSA-N tert-butyl N-[2-[[2-hydroxy-3-(2-methoxyphenoxy)propyl]amino]ethyl]carbamate Chemical compound COC1=CC=CC=C1OCC(O)CNCCNC(=O)OC(C)(C)C CHFDHHMRZRLEJD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biochemistry (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18430600P | 2000-02-22 | 2000-02-22 | |
| US18418200P | 2000-02-22 | 2000-02-22 | |
| US18445700P | 2000-02-22 | 2000-02-22 | |
| US60/184,306 | 2000-02-22 | ||
| US60/184,182 | 2000-02-22 | ||
| US60/184,457 | 2000-02-22 | ||
| US20639600P | 2000-05-23 | 2000-05-23 | |
| US60/206,396 | 2000-05-23 | ||
| US20926200P | 2000-06-05 | 2000-06-05 | |
| US60/209,262 | 2000-06-05 | ||
| CA002400176A CA2400176C (fr) | 2000-02-22 | 2001-02-22 | Composes de piperazine substitues |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002400176A Division CA2400176C (fr) | 2000-02-22 | 2001-02-22 | Composes de piperazine substitues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2657986A1 true CA2657986A1 (fr) | 2001-08-30 |
Family
ID=27539118
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002657986A Abandoned CA2657986A1 (fr) | 2000-02-22 | 2001-02-22 | Composes de piperazine substitues |
| CA002400176A Expired - Fee Related CA2400176C (fr) | 2000-02-22 | 2001-02-22 | Composes de piperazine substitues |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002400176A Expired - Fee Related CA2400176C (fr) | 2000-02-22 | 2001-02-22 | Composes de piperazine substitues |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1259493A2 (fr) |
| JP (2) | JP3980885B2 (fr) |
| KR (1) | KR100595942B1 (fr) |
| CN (1) | CN1404471A (fr) |
| AR (1) | AR029229A1 (fr) |
| AU (2) | AU2001238623B2 (fr) |
| BR (1) | BR0108592A (fr) |
| CA (2) | CA2657986A1 (fr) |
| IL (1) | IL151178A0 (fr) |
| MX (1) | MXPA02008213A (fr) |
| NO (1) | NO324837B1 (fr) |
| NZ (1) | NZ520782A (fr) |
| TW (1) | TWI236471B (fr) |
| WO (1) | WO2001062744A2 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505886A (ja) * | 2000-02-18 | 2004-02-26 | スィーヴィー セラピューティクス インコーポレイテッド | 鬱血性心不全の処置における部分的な脂肪酸酸化阻害剤 |
| WO2003008411A1 (fr) | 2001-07-19 | 2003-01-30 | Cv Therapeutics, Inc. | Composes de piperazine substitues et leur utilisation en tant qu'inhibiteurs de l'oxydation d'acides gras |
| US7001909B2 (en) | 2001-07-19 | 2006-02-21 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| EP1806346B1 (fr) * | 2002-12-05 | 2009-07-22 | Cv Therapeutics, Inc. | Dérivés de Pipérazine substitués et leur utilisation comme inhibiteurs de l'oxydation d'acids gras |
| AU2003300827B2 (en) * | 2002-12-05 | 2009-08-13 | Gilead Palo Alto, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| NZ541069A (en) * | 2003-01-03 | 2008-09-26 | Cv Therapeutics Inc | Piperazine derivatives as fatty acid oxidation inhibitors |
| NZ544449A (en) * | 2003-06-23 | 2008-10-31 | Cv Therapeutics Inc | Urea derivatives of piperazines and piperidines as fatty acid oxidation inhibitors |
| EP1723129A1 (fr) * | 2003-12-18 | 2006-11-22 | Cv Therapeutics, Inc. | Composes piperazine et piperazine 1-akan-2-ol substitues |
| WO2006029179A2 (fr) * | 2004-09-08 | 2006-03-16 | Cv Therapeutics, Inc. | Composes heterocycliques substitues |
| CN102875490A (zh) * | 2012-10-19 | 2013-01-16 | 四川大学 | 一种用于制备雷诺嗪的合成方法 |
| CN107043361B (zh) * | 2017-05-25 | 2019-07-02 | 合肥医工医药股份有限公司 | 治疗心绞痛的化合物、制备方法及用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766125A (en) * | 1981-06-23 | 1988-08-23 | Janssen Pharmaceutica N.V. | N-aryl-piperazinealkanamides useful for protecting hearts from myocardial injury caused by ischaemia, anoxia or hypoxia |
| JPS584774A (ja) * | 1981-06-23 | 1983-01-11 | ジヤンセン・フア−マシユ−チカ・ナ−ムロ−ゼ・フエンノ−トシヤツプ | N−アリ−ル−ピペラジンアルカンアミド類 |
| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| US4558129A (en) * | 1983-05-18 | 1985-12-10 | Syntex (U.S.A.) Inc. | Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade |
| FR2552083B1 (fr) * | 1983-09-15 | 1986-05-09 | Cerm Cent Europ Rech Mauvernay | Derives de (alkynyloxy-3 hydroxy-2-propyl)-4 piperazinyl-1 n-phenyl acetamide, leur preparation et leur application en therapeutique |
| ATE142497T1 (de) * | 1989-06-23 | 1996-09-15 | Syntex Inc | Ranolazin und verwandte piperazine zur behandlung von geweben, von physischen oder chemischen schäden betroffen |
| JPH03141258A (ja) * | 1989-10-25 | 1991-06-17 | Kowa Co | 新規なピペラジン誘導体 |
| HU209723B (en) * | 1990-10-31 | 1994-10-28 | Richter Gedeon Vegyeszet | Process for producing of piperazine derivatives |
-
2001
- 2001-02-22 IL IL15117801A patent/IL151178A0/xx unknown
- 2001-02-22 AR ARP010100804A patent/AR029229A1/es unknown
- 2001-02-22 CA CA002657986A patent/CA2657986A1/fr not_active Abandoned
- 2001-02-22 JP JP2001562526A patent/JP3980885B2/ja not_active Expired - Lifetime
- 2001-02-22 BR BR0108592-1A patent/BR0108592A/pt not_active Application Discontinuation
- 2001-02-22 EP EP01911085A patent/EP1259493A2/fr not_active Withdrawn
- 2001-02-22 KR KR1020027011014A patent/KR100595942B1/ko not_active Expired - Fee Related
- 2001-02-22 AU AU2001238623A patent/AU2001238623B2/en not_active Ceased
- 2001-02-22 CN CN01805442A patent/CN1404471A/zh active Pending
- 2001-02-22 WO PCT/US2001/005606 patent/WO2001062744A2/fr not_active Ceased
- 2001-02-22 CA CA002400176A patent/CA2400176C/fr not_active Expired - Fee Related
- 2001-02-22 NZ NZ520782A patent/NZ520782A/en unknown
- 2001-02-22 AU AU3862301A patent/AU3862301A/xx active Pending
- 2001-02-22 MX MXPA02008213A patent/MXPA02008213A/es active IP Right Grant
- 2001-04-13 TW TW090104080A patent/TWI236471B/zh not_active IP Right Cessation
-
2002
- 2002-08-20 NO NO20023954A patent/NO324837B1/no not_active IP Right Cessation
-
2007
- 2007-01-15 JP JP2007005347A patent/JP2007211009A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NZ520782A (en) | 2004-03-26 |
| WO2001062744A2 (fr) | 2001-08-30 |
| KR100595942B1 (ko) | 2006-07-03 |
| NO20023954L (no) | 2002-09-30 |
| CN1404471A (zh) | 2003-03-19 |
| CA2400176A1 (fr) | 2001-08-30 |
| NO324837B1 (no) | 2007-12-17 |
| WO2001062744A3 (fr) | 2002-02-07 |
| CA2400176C (fr) | 2009-04-28 |
| AU2001238623B2 (en) | 2004-09-23 |
| KR20020079893A (ko) | 2002-10-19 |
| JP2007211009A (ja) | 2007-08-23 |
| MXPA02008213A (es) | 2004-04-05 |
| TWI236471B (en) | 2005-07-21 |
| EP1259493A2 (fr) | 2002-11-27 |
| AR029229A1 (es) | 2003-06-18 |
| BR0108592A (pt) | 2004-06-29 |
| NO20023954D0 (no) | 2002-08-20 |
| AU3862301A (en) | 2001-09-03 |
| JP2003531116A (ja) | 2003-10-21 |
| IL151178A0 (en) | 2003-04-10 |
| JP3980885B2 (ja) | 2007-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |