JP2008508249A5 - - Google Patents
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- Publication number
- JP2008508249A5 JP2008508249A5 JP2007523162A JP2007523162A JP2008508249A5 JP 2008508249 A5 JP2008508249 A5 JP 2008508249A5 JP 2007523162 A JP2007523162 A JP 2007523162A JP 2007523162 A JP2007523162 A JP 2007523162A JP 2008508249 A5 JP2008508249 A5 JP 2008508249A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydroxy
- group
- piperidine
- carboxylic acid
- 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.)
- Withdrawn
Links
- 125000005843 halogen group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- -1 hydroxy, benzyloxy, amino Chemical group 0.000 claims 6
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 230000003287 optical effect Effects 0.000 claims 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical class O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010058019 Cancer Pain Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010011878 Deafness Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 150000003936 benzamides Chemical class 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229960003920 cocaine Drugs 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003995 emulsifying agent Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 claims 2
- 235000013355 food flavoring agent Nutrition 0.000 claims 2
- 239000003205 fragrance Substances 0.000 claims 2
- 230000010370 hearing loss Effects 0.000 claims 2
- 231100000888 hearing loss Toxicity 0.000 claims 2
- 208000016354 hearing loss disease Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 231100000878 neurological injury Toxicity 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000003204 osmotic effect Effects 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000011347 resin Substances 0.000 claims 2
- 229920005989 resin Polymers 0.000 claims 2
- 210000001525 retina Anatomy 0.000 claims 2
- 210000000278 spinal cord Anatomy 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- 230000008736 traumatic injury Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 238000009736 wetting Methods 0.000 claims 2
- 239000000080 wetting agent Substances 0.000 claims 2
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
- ITXGAJCPAGYAJF-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-n-(4-hydroxybenzoyl)piperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C(=O)NC(=O)N1CCC(CC=2C=CC(Cl)=CC=2)CC1 ITXGAJCPAGYAJF-UHFFFAOYSA-N 0.000 claims 1
- SPUUORLTOKRGBY-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-n-(4-hydroxybenzoyl)piperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C(=O)NC(=O)N1CCC(CC=2C=CC(F)=CC=2)CC1 SPUUORLTOKRGBY-UHFFFAOYSA-N 0.000 claims 1
- SUQBNXQIAZGVKU-UHFFFAOYSA-N 4-benzyl-n-(4-hydroxybenzoyl)piperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C(=O)NC(=O)N1CCC(CC=2C=CC=CC=2)CC1 SUQBNXQIAZGVKU-UHFFFAOYSA-N 0.000 claims 1
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical group O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims 1
- 102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 claims 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 1
- BWIMHFGKSLCNEP-UHFFFAOYSA-N N-[4-(methanesulfonamido)benzoyl]-4-[(4-methylphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1CC1CCN(C(=O)NC(=O)C=2C=CC(NS(C)(=O)=O)=CC=2)CC1 BWIMHFGKSLCNEP-UHFFFAOYSA-N 0.000 claims 1
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 108010038912 Retinoid X Receptors Proteins 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- IKLAWTBCMDRBRH-UHFFFAOYSA-N n-(4-benzylpiperidine-1-carbonyl)-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound C=1C=C2NC(=O)OC2=CC=1C(=O)NC(=O)N(CC1)CCC1CC1=CC=CC=C1 IKLAWTBCMDRBRH-UHFFFAOYSA-N 0.000 claims 1
- MZISVEGLLHFXCG-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-(phenylsulfanylmethyl)piperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C(=O)NC(=O)N1CCC(CSC=2C=CC=CC=2)CC1 MZISVEGLLHFXCG-UHFFFAOYSA-N 0.000 claims 1
- HCGUJJPDXAJGAW-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-[(3-methoxyphenyl)methyl]piperidine-1-carboxamide Chemical compound COC1=CC=CC(CC2CCN(CC2)C(=O)NC(=O)C=2C=CC(O)=CC=2)=C1 HCGUJJPDXAJGAW-UHFFFAOYSA-N 0.000 claims 1
- BTKGSXIFWKUVCZ-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-[(4-methoxyphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CC1CCN(C(=O)NC(=O)C=2C=CC(O)=CC=2)CC1 BTKGSXIFWKUVCZ-UHFFFAOYSA-N 0.000 claims 1
- WLMWGRLEGFSXPD-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-[(4-methylphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1CC1CCN(C(=O)NC(=O)C=2C=CC(O)=CC=2)CC1 WLMWGRLEGFSXPD-UHFFFAOYSA-N 0.000 claims 1
- OWYBROBJWOMMRK-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-[2-(4-methylphenyl)ethyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1CCC1CCN(C(=O)NC(=O)C=2C=CC(O)=CC=2)CC1 OWYBROBJWOMMRK-UHFFFAOYSA-N 0.000 claims 1
- NFCKOGJVSQNAKZ-UHFFFAOYSA-N n-(4-hydroxybenzoyl)-4-[[4-(trifluoromethyl)phenyl]methyl]piperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C(=O)NC(=O)N1CCC(CC=2C=CC(=CC=2)C(F)(F)F)CC1 NFCKOGJVSQNAKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- IMWUREPEYPRYOR-UHFFFAOYSA-N pyrrolidine-2-thione Chemical compound S=C1CCCN1 IMWUREPEYPRYOR-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0401524A HU227000B1 (en) | 2004-07-29 | 2004-07-29 | Nmda receptor antagonist benzoyl urea derivatives, and pharmaceutical compositions containing them |
| PCT/HU2005/000079 WO2006010966A1 (en) | 2004-07-29 | 2005-07-21 | New benzoyl urea derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008508249A JP2008508249A (ja) | 2008-03-21 |
| JP2008508249A5 true JP2008508249A5 (US07794700-20100914-C00152.png) | 2008-05-15 |
Family
ID=89985409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007523162A Withdrawn JP2008508249A (ja) | 2004-07-29 | 2005-07-21 | 新規なベンゾイル尿素誘導体 |
Country Status (19)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8114843B2 (en) * | 2005-11-18 | 2012-02-14 | The Regents Of The University Of California | Photoreactive regulator of protein function and methods of use thereof |
| EP2520567A3 (en) | 2006-02-23 | 2012-12-12 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle derivatives substituted with cyclic group |
| JPWO2008023720A1 (ja) * | 2006-08-23 | 2010-01-14 | アステラス製薬株式会社 | ウレア化合物又はその塩 |
| MX2012008721A (es) | 2010-02-16 | 2012-08-17 | Pfizer | (r)-4-((4-((4-(tetrahidrofuran-3-iloxi)benzo[d]isoxazol-3-iloxi)m etil) tetrahidro-2h-piran-4-ol, un agonista pacial de receptores 5-ht4. |
| CN102532062B (zh) * | 2010-12-08 | 2013-12-04 | 上海工程技术大学 | 一种苯甲酰脲化合物及其合成方法 |
| KR101481952B1 (ko) | 2012-04-13 | 2015-01-22 | 한국과학기술연구원 | 신경보호제로서의 유레아 유도체 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882273A (en) * | 1958-02-07 | 1959-04-14 | Bristol Lab Inc | Therapeutic agents |
| US4152430A (en) * | 1977-09-22 | 1979-05-01 | William H. Rorer, Inc. | Synergistic compositions and method of use |
| EP1186303A3 (en) * | 2000-09-06 | 2003-12-10 | Pfizer Products Inc. | Pharmaceutical combinations, for the treatment of stroke and traumatic brain injury, containing a neutrophil inhibiting factor and an selective NMDA-NR2B receptor antagonist |
| MXPA04000737A (es) * | 2001-07-24 | 2004-07-08 | Richter Gedeon Vegyeszet | Derivados de piperidina como antagonistas receptores de nmda. |
-
2004
- 2004-07-29 HU HU0401524A patent/HU227000B1/hu unknown
-
2005
- 2005-07-21 AU AU2005266161A patent/AU2005266161A1/en not_active Abandoned
- 2005-07-21 KR KR1020077000264A patent/KR20070039033A/ko not_active Application Discontinuation
- 2005-07-21 CN CNA2005800241971A patent/CN1989119A/zh active Pending
- 2005-07-21 BR BRPI0513924-4A patent/BRPI0513924A/pt not_active IP Right Cessation
- 2005-07-21 CA CA002574158A patent/CA2574158A1/en not_active Abandoned
- 2005-07-21 AP AP2006003841A patent/AP2006003841A0/xx unknown
- 2005-07-21 GE GEAP20059894A patent/GEP20094607B/en unknown
- 2005-07-21 MX MX2007001042A patent/MX2007001042A/es not_active Application Discontinuation
- 2005-07-21 US US11/658,788 patent/US20090170901A1/en not_active Abandoned
- 2005-07-21 EA EA200700366A patent/EA010893B1/ru not_active IP Right Cessation
- 2005-07-21 WO PCT/HU2005/000079 patent/WO2006010966A1/en active Application Filing
- 2005-07-21 EP EP05764413A patent/EP1771429A1/en not_active Withdrawn
- 2005-07-21 JP JP2007523162A patent/JP2008508249A/ja not_active Withdrawn
-
2006
- 2006-11-22 IL IL179486A patent/IL179486A0/en unknown
-
2007
- 2007-01-11 ZA ZA200700322A patent/ZA200700322B/en unknown
- 2007-01-17 TN TNP2007000017A patent/TNSN07017A1/en unknown
- 2007-02-22 MA MA29704A patent/MA28817B1/fr unknown
- 2007-02-27 NO NO20071110A patent/NO20071110L/no not_active Application Discontinuation
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