DOI: 10.1021/jm049499o. Synthesis, Structure−Activity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists

Synthesis, Structure−Activity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists

10.1021/jm049499o

Crossref journal-article

American Chemical Society (ACS)

Journal of Medicinal Chemistry (316)

Bibliography

Mabire, D., Coupa, S., Adelinet, C., Poncelet, A., Simonnet, Y., Venet, M., Wouters, R., Lesage, A. S. J., Beijsterveldt, L. V., & Bischoff, F. (2005). Synthesis, StructureâActivity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists. Journal of Medicinal Chemistry, 48(6), 2134â2153.

Authors 10

Dominique Mabire (first)
Sophie Coupa (additional)
Christophe Adelinet (additional)
Alain Poncelet (additional)
Yvan Simonnet (additional)
Marc Venet (additional)
Ria Wouters (additional)
Anne S. J. Lesage (additional)
Ludy Van Beijsterveldt (additional)
François Bischoff (additional)

References 48 Referenced 86

{'key': 'jm049499ob00001/jm049499ob00001_1', 'first-page': '61', 'volume': '51', 'author': 'Dingledine R.', 'year': '1999', 'journal-title': 'Pharmacol. Rev.'} / Pharmacol. Rev. by Dingledine R. (1999)
10.1046/j.1471-4159.1999.0722539.x / J. Neurochem. by Robbins M. J. (1999)
10.1002/cne.903550310 / J. Comput. Neurol. by Romano C. (1995)
{'key': 'jm049499ob00004/jm049499ob00004_1', 'first-page': '98', 'volume-title': 'Handbook of Experimental Pharmacology:\u2009 Ionotropic Glutamate Receptors in the CNS', 'author': 'Hollmann M.', 'year': '1999'} / Handbook of Experimental Pharmacology: Ionotropic Glutamate Receptors in the CNS by Hollmann M. (1999)
10.1146/annurev.ne.17.030194.000335 / Annu. Rev. Neurosci. by Hollmann M. (1994)
10.1016/0896-6273(94)90043-4 / Neuron by Nakanishi S (1994)
{'key': 'jm049499ob00007/jm049499ob00007_1', 'first-page': '26', 'volume': '34', 'author': 'Pin J. P.', 'year': '1995', 'journal-title': 'Neuropharmacology'} / Neuropharmacology by Pin J. P. (1995)
10.1016/0197-0186(94)90092-2 / Neurochem. Int. by Schoepp D. D (1994)
{'key': 'jm049499ob00009/jm049499ob00009_1', 'first-page': '474', 'volume': '757', 'author': 'Miller S.', 'year': '1994', 'journal-title': 'Ann. N. Y. Acad. Sci.'} / Ann. N. Y. Acad. Sci. by Miller S. (1994)
{'key': 'jm049499ob00010/jm049499ob00010_1', 'first-page': '79', 'volume': '59', 'author': 'Bordi F.', 'year': '1999', 'journal-title': 'Prog. Neuropharmacology'} / Prog. Neuropharmacology by Bordi F. (1999)
10.1016/S1471-4892(01)00119-9 / Curr. Opin. Pharmacol. by Gasparini F. (2002)
{'key': 'jm049499ob00012/jm049499ob00012_1', 'first-page': '393', 'volume': '2', 'author': 'Lesage A. S. J', 'year': '2004', 'journal-title': 'Curr. Neuropharmacol.'} / Curr. Neuropharmacol. by Lesage A. S. J (2004)
10.2174/1568007023339300 / Curr. Drug Targets CNS & Neurol. Disord. by Varney M. A. (2002)
10.1016/S0304-3959(02)00140-9 / Pain by Neugebauer V (2002)
{'key': 'jm049499ob00015/jm049499ob00015_1', 'volume-title': 'Insight into the function of Group I and Group II metabotropic (mGlu) receptors:\u2009 Behavioural characterization and implications for the treatment of CNS disorders', 'author': 'Spooren W.', 'year': '2003'} / Insight into the function of Group I and Group II metabotropic (mGlu) receptors: Behavioural characterization and implications for the treatment of CNS disorders by Spooren W. (2003)
{'key': 'jm049499ob00016/jm049499ob00016_1', 'first-page': '137', 'volume-title': 'Excitatory Amino Acids:\u2009 Ten Years Later', 'author': 'Salt T. E.', 'year': '2001'} / Excitatory Amino Acids: Ten Years Later by Salt T. E. (2001)
10.1074/jbc.M006230200 / J. Biol. Chem. by Pagano A. (2000)
10.1016/S0014-2999(01)01296-1 / Eur. J. Pharmacol. by De Vry J. (2001)
{'key': 'jm049499ob00019/jm049499ob00019_1', 'volume-title': 'Remedies for brain infarction. PCT Int. Appl', 'author': 'Okada M.', 'year': '1999'} / Remedies for brain infarction. PCT Int. Appl by Okada M. (1999)
{'key': 'jm049499ob00020/jm049499ob00020_1', 'first-page': '073283', 'author': 'Van Wagenen B. C.', 'year': '2000', 'journal-title': 'WO'} / WO by Van Wagenen B. C. (2000)
{'key': 'jm049499ob00021/jm049499ob00021_1', 'first-page': '051418', 'author': 'Binggeli A.', 'year': '2002', 'journal-title': 'WO'} / WO by Binggeli A. (2002)
{'key': 'jm049499ob00022/jm049499ob00022_1', 'first-page': '026199', 'author': 'Clark B. P.', 'year': '2000', 'journal-title': 'WO'} / WO by Clark B. P. (2000)
{'key': 'jm049499ob00023/jm049499ob00023_1', 'first-page': '032632', 'author': 'Ambler S. J.', 'year': '2001', 'journal-title': 'WO'} / WO by Ambler S. J. (2001)
10.1016/S0960-894X(03)00396-2 / Bioorg. Med. Chem. Lett. by Micheli F. (2003)
{'key': 'jm049499ob00025/jm049499ob00025_1', 'first-page': '6758', 'volume': '31', 'author': 'Corcoran R. C.', 'year': '1990', 'journal-title': 'Tetrahedron Lett.'} / Tetrahedron Lett. by Corcoran R. C. (1990)
10.1021/jo00374a041 / J. Org. Chem. by Chatani N. (1986)
{'key': 'jm049499ob00027/jm049499ob00027_1', 'first-page': '2488', 'volume': '2484', 'author': 'Gagan J. M. F.', 'year': '1970', 'journal-title': 'J. Chem. Soc (C).'} / J. Chem. Soc (C). by Gagan J. M. F. (1970)
{'key': 'jm049499ob00028/jm049499ob00028_1', 'first-page': '2492', 'volume': '2488', 'author': 'Gagan J. M. F.', 'year': '1970', 'journal-title': 'J. Chem. Soc (C).'} / J. Chem. Soc (C). by Gagan J. M. F. (1970)
10.1016/S0968-0896(96)00216-7 / Bioorg. Med. Chem. by Imaki K. (1996)
{'key': 'jm049499ob00030/jm049499ob00030_1', 'first-page': '3560', 'volume': '98', 'author': 'Bodendorf K.', 'year': '1965', 'journal-title': 'Chem. Ber.'} / Chem. Ber. by Bodendorf K. (1965)
{'key': 'jm049499ob00031/jm049499ob00031_1', 'first-page': '918', 'volume': '6', 'author': 'Yus M.', 'year': '2001', 'journal-title': 'Synthesis'} / Synthesis by Yus M. (2001)
{'key': 'jm049499ob00032/jm049499ob00032_1', 'first-page': '3905', 'volume': '43', 'author': 'Wei Z.-Y.', 'year': '2000', 'journal-title': 'J. Med. Chem.'} / J. Med. Chem. by Wei Z.-Y. (2000)
{'key': 'jm049499ob00033/jm049499ob00033_1', 'first-page': '3790', 'volume': '11', 'author': 'Li J. J.', 'year': '2003', 'journal-title': 'Bioorg. Med. Chem.'} / Bioorg. Med. Chem. by Li J. J. (2003)
Sterling Drug, Inc. 3,3-Dichloro-2-oxopolymethylimines. 1970, GB1192670.
10.1002/jhet.5570310401 / J. Heterocycl. Chem. by Cziaky Z. (1994)
{'key': 'jm049499ob00036/jm049499ob00036_1', 'volume-title': 'Preparation of benzoxepinecarboxamides, benzocycloheptenecarboxamides, and related compounds as CCR5 antagonists. PCT Int. Appl', 'author': 'Nishimura O.', 'year': '1999'} / Preparation of benzoxepinecarboxamides, benzocycloheptenecarboxamides, and related compounds as CCR5 antagonists. PCT Int. Appl by Nishimura O. (1999)
10.1002/cber.19490820110 / Chem. Ber. by Henecka H (1949)
10.1021/jo026203i / J. Org. Chem. by Dormer P. (2003)
10.1021/jf00021a042 / J. Agric. Food. Chem. by Hara T. (1992)
{'key': 'jm049499ob00040/jm049499ob00040_1', 'first-page': '23', 'volume': '17', 'author': 'Gnanasekaran S. J. R.', 'year': '1993', 'journal-title': 'Sulfur Lett.'} / Sulfur Lett. by Gnanasekaran S. J. R. (1993)
10.1124/mol.63.5.1082 / Mol. Pharmacol. by Lavreysen H. (2003)
10.1016/j.neuropharm.2004.08.007 / Neuropharmacol. by Lavreysen H. (2004)
{'key': 'jm049499ob00043/jm049499ob00043_1', 'volume-title': 'Effects of mGlu1 receptor blockade on anxiety-related behaviour in the rat lick suppression test. Psychopharmacol', 'author': 'Steckler T.', 'year': '2004'} / Effects of mGlu1 receptor blockade on anxiety-related behaviour in the rat lick suppression test. Psychopharmacol by Steckler T. (2004)
{'issue': '31', 'key': 'jm049499ob00045/jm049499ob00045_1', 'first-page': '5464', 'volume': '36', 'author': 'Williams J. M.', 'year': '1995', 'journal-title': 'Tetrahedron Lett.'} / Tetrahedron Lett. by Williams J. M. (1995)
Edwards, P. N.; Waterson, D. α,α-Dialkylbenzyl derivatives containing aromatic and heteroaromatic nuclei and their preparation and use as 5-lipoxygenase inhibitors. Eur. Pat. Appl. 1992, EP 505122.
10.1021/jm030327l / J. Med. Chem. by Perner R. J. (2003)
10.1124/mol.61.5.1244 / Mol. Pharmacol. by Lavreysen H. (2002)
10.1016/S0009-9236(97)90135-1 / Clin. Pharmacol. Ther. by Iatsimirskaia E. (1997)

Dates

Type	When
Created	20 years, 5 months ago (March 17, 2005, 12:26 a.m.)
Deposited	1 year, 7 months ago (Jan. 23, 2024, 10:04 p.m.)
Indexed	2 months ago (July 1, 2025, 4:38 p.m.)
Issued	20 years, 7 months ago (Jan. 28, 2005)
Published	20 years, 7 months ago (Jan. 28, 2005)
Published Online	20 years, 7 months ago (Jan. 28, 2005)
Published Print	20 years, 6 months ago (March 1, 2005)

Funders 0

None

BibTeX

@article{Mabire_2005, title={Synthesis, Structureâˆ’Activity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists}, volume={48}, ISSN={1520-4804}, url={http://dx.doi.org/10.1021/jm049499o}, DOI={10.1021/jm049499o}, number={6}, journal={Journal of Medicinal Chemistry}, publisher={American Chemical Society (ACS)}, author={Mabire, Dominique and Coupa, Sophie and Adelinet, Christophe and Poncelet, Alain and Simonnet, Yvan and Venet, Marc and Wouters, Ria and Lesage, Anne S. J. and Beijsterveldt, Ludy Van and Bischoff, FranĂ§ois}, year={2005}, month=jan, pages={2134â€“2153} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        1
      ]
    ],
    "date-time": "2025-07-01T20:38:00Z",
    "timestamp": 1751402280133
  },
  "reference-count": 48,
  "publisher": "American Chemical Society (ACS)",
  "issue": "6",
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2005,
        3,
        1
      ]
    ]
  },
  "DOI": "10.1021/jm049499o",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2005,
        3,
        17
      ]
    ],
    "date-time": "2005-03-17T05:26:48Z",
    "timestamp": 1111037208000
  },
  "page": "2134-2153",
  "source": "Crossref",
  "is-referenced-by-count": 86,
  "title": "Synthesis, Structure\u2212Activity Relationship, and Receptor Pharmacology of a New Series of Quinoline Derivatives Acting as Selective, Noncompetitive mGlu1 Antagonists",
  "prefix": "10.1021",
  "volume": "48",
  "author": [
    {
      "given": "Dominique",
      "family": "Mabire",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Sophie",
      "family": "Coupa",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Christophe",
      "family": "Adelinet",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Alain",
      "family": "Poncelet",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Yvan",
      "family": "Simonnet",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Marc",
      "family": "Venet",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Ria",
      "family": "Wouters",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Anne S. J.",
      "family": "Lesage",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Ludy Van",
      "family": "Beijsterveldt",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    },
    {
      "given": "Fran\u00e7ois",
      "family": "Bischoff",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Medicinal Chemistry, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen-Cilag France, Campus de Maigremont, F-27106 Val de Reuil, France, and Department of Medicinal Chemistry, CNS Discovery Research and Department of Preclinical Pharmacokinetics, Johnson & Johnson Pharmaceutical Research & Development, a Division of Janssen Pharmaceutica N.V., Turnhoutseweg 30, B-2340 Beerse, Belgium"
        }
      ]
    }
  ],
  "member": "316",
  "published-online": {
    "date-parts": [
      [
        2005,
        1,
        28
      ]
    ]
  },
  "reference": [
    {
      "key": "jm049499ob00001/jm049499ob00001_1",
      "first-page": "61",
      "volume": "51",
      "author": "Dingledine R.",
      "year": "1999",
      "journal-title": "Pharmacol. Rev."
    },
    {
      "key": "jm049499ob00002/jm049499ob00002_1",
      "doi-asserted-by": "crossref",
      "first-page": "2547",
      "DOI": "10.1046/j.1471-4159.1999.0722539.x",
      "volume": "72",
      "author": "Robbins M. J.",
      "year": "1999",
      "journal-title": "J. Neurochem."
    },
    {
      "key": "jm049499ob00003/jm049499ob00003_1",
      "doi-asserted-by": "crossref",
      "first-page": "469",
      "DOI": "10.1002/cne.903550310",
      "volume": "355",
      "author": "Romano C.",
      "year": "1995",
      "journal-title": "J. Comput. Neurol."
    },
    {
      "key": "jm049499ob00004/jm049499ob00004_1",
      "first-page": "98",
      "volume-title": "Handbook of Experimental Pharmacology:\u2009 Ionotropic Glutamate Receptors in the CNS",
      "author": "Hollmann M.",
      "year": "1999"
    },
    {
      "key": "jm049499ob00005/jm049499ob00005_1",
      "doi-asserted-by": "crossref",
      "first-page": "108",
      "DOI": "10.1146/annurev.ne.17.030194.000335",
      "volume": "17",
      "author": "Hollmann M.",
      "year": "1994",
      "journal-title": "Annu. Rev. Neurosci."
    },
    {
      "key": "jm049499ob00006/jm049499ob00006_1",
      "doi-asserted-by": "crossref",
      "first-page": "1037",
      "DOI": "10.1016/0896-6273(94)90043-4",
      "volume": "13",
      "author": "Nakanishi S",
      "year": "1994",
      "journal-title": "Neuron"
    },
    {
      "key": "jm049499ob00007/jm049499ob00007_1",
      "first-page": "26",
      "volume": "34",
      "author": "Pin J. P.",
      "year": "1995",
      "journal-title": "Neuropharmacology"
    },
    {
      "key": "jm049499ob00008/jm049499ob00008_1",
      "doi-asserted-by": "crossref",
      "first-page": "449",
      "DOI": "10.1016/0197-0186(94)90092-2",
      "volume": "24",
      "author": "Schoepp D. D",
      "year": "1994",
      "journal-title": "Neurochem. Int."
    },
    {
      "key": "jm049499ob00009/jm049499ob00009_1",
      "first-page": "474",
      "volume": "757",
      "author": "Miller S.",
      "year": "1994",
      "journal-title": "Ann. N. Y. Acad. Sci."
    },
    {
      "key": "jm049499ob00010/jm049499ob00010_1",
      "first-page": "79",
      "volume": "59",
      "author": "Bordi F.",
      "year": "1999",
      "journal-title": "Prog. Neuropharmacology"
    },
    {
      "key": "jm049499ob00011/jm049499ob00011_1",
      "doi-asserted-by": "crossref",
      "first-page": "49",
      "DOI": "10.1016/S1471-4892(01)00119-9",
      "volume": "2",
      "author": "Gasparini F.",
      "year": "2002",
      "journal-title": "Curr. Opin. Pharmacol."
    },
    {
      "key": "jm049499ob00012/jm049499ob00012_1",
      "first-page": "393",
      "volume": "2",
      "author": "Lesage A. S. J",
      "year": "2004",
      "journal-title": "Curr. Neuropharmacol."
    },
    {
      "key": "jm049499ob00013/jm049499ob00013_1",
      "doi-asserted-by": "crossref",
      "first-page": "296",
      "DOI": "10.2174/1568007023339300",
      "volume": "1",
      "author": "Varney M. A.",
      "year": "2002",
      "journal-title": "Curr. Drug Targets CNS & Neurol. Disord."
    },
    {
      "key": "jm049499ob00014/jm049499ob00014_1",
      "doi-asserted-by": "crossref",
      "first-page": "8",
      "DOI": "10.1016/S0304-3959(02)00140-9",
      "volume": "98",
      "author": "Neugebauer V",
      "year": "2002",
      "journal-title": "Pain"
    },
    {
      "key": "jm049499ob00015/jm049499ob00015_1",
      "volume-title": "Insight into the function of Group I and Group II metabotropic (mGlu) receptors:\u2009 Behavioural characterization and implications for the treatment of CNS disorders",
      "author": "Spooren W.",
      "year": "2003"
    },
    {
      "key": "jm049499ob00016/jm049499ob00016_1",
      "first-page": "137",
      "volume-title": "Excitatory Amino Acids:\u2009 Ten Years Later",
      "author": "Salt T. E.",
      "year": "2001"
    },
    {
      "key": "jm049499ob00017/jm049499ob00017_1",
      "doi-asserted-by": "crossref",
      "first-page": "33758",
      "DOI": "10.1074/jbc.M006230200",
      "volume": "275",
      "author": "Pagano A.",
      "year": "2000",
      "journal-title": "J. Biol. Chem."
    },
    {
      "key": "jm049499ob00018/jm049499ob00018_1",
      "doi-asserted-by": "crossref",
      "first-page": "214",
      "DOI": "10.1016/S0014-2999(01)01296-1",
      "volume": "428",
      "author": "De Vry J.",
      "year": "2001",
      "journal-title": "Eur. J. Pharmacol."
    },
    {
      "key": "jm049499ob00019/jm049499ob00019_1",
      "volume-title": "Remedies for brain infarction. PCT Int. Appl",
      "author": "Okada M.",
      "year": "1999"
    },
    {
      "key": "jm049499ob00020/jm049499ob00020_1",
      "first-page": "073283",
      "author": "Van Wagenen B. C.",
      "year": "2000",
      "journal-title": "WO"
    },
    {
      "key": "jm049499ob00021/jm049499ob00021_1",
      "first-page": "051418",
      "author": "Binggeli A.",
      "year": "2002",
      "journal-title": "WO"
    },
    {
      "key": "jm049499ob00022/jm049499ob00022_1",
      "first-page": "026199",
      "author": "Clark B. P.",
      "year": "2000",
      "journal-title": "WO"
    },
    {
      "key": "jm049499ob00023/jm049499ob00023_1",
      "first-page": "032632",
      "author": "Ambler S. J.",
      "year": "2001",
      "journal-title": "WO"
    },
    {
      "key": "jm049499ob00024/jm049499ob00024_1",
      "doi-asserted-by": "crossref",
      "first-page": "2118",
      "DOI": "10.1016/S0960-894X(03)00396-2",
      "volume": "13",
      "author": "Micheli F.",
      "year": "2003",
      "journal-title": "Bioorg. Med. Chem. Lett."
    },
    {
      "key": "jm049499ob00025/jm049499ob00025_1",
      "first-page": "6758",
      "volume": "31",
      "author": "Corcoran R. C.",
      "year": "1990",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "jm049499ob00026/jm049499ob00026_1",
      "doi-asserted-by": "crossref",
      "first-page": "4716",
      "DOI": "10.1021/jo00374a041",
      "volume": "51",
      "author": "Chatani N.",
      "year": "1986",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "jm049499ob00027/jm049499ob00027_1",
      "first-page": "2488",
      "volume": "2484",
      "author": "Gagan J. M. F.",
      "year": "1970",
      "journal-title": "J. Chem. Soc (C)."
    },
    {
      "key": "jm049499ob00028/jm049499ob00028_1",
      "first-page": "2492",
      "volume": "2488",
      "author": "Gagan J. M. F.",
      "year": "1970",
      "journal-title": "J. Chem. Soc (C)."
    },
    {
      "key": "jm049499ob00029/jm049499ob00029_1",
      "doi-asserted-by": "crossref",
      "first-page": "2134",
      "DOI": "10.1016/S0968-0896(96)00216-7",
      "volume": "4",
      "author": "Imaki K.",
      "year": "1996",
      "journal-title": "Bioorg. Med. Chem."
    },
    {
      "key": "jm049499ob00030/jm049499ob00030_1",
      "first-page": "3560",
      "volume": "98",
      "author": "Bodendorf K.",
      "year": "1965",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "jm049499ob00031/jm049499ob00031_1",
      "first-page": "918",
      "volume": "6",
      "author": "Yus M.",
      "year": "2001",
      "journal-title": "Synthesis"
    },
    {
      "key": "jm049499ob00032/jm049499ob00032_1",
      "first-page": "3905",
      "volume": "43",
      "author": "Wei Z.-Y.",
      "year": "2000",
      "journal-title": "J. Med. Chem."
    },
    {
      "key": "jm049499ob00033/jm049499ob00033_1",
      "first-page": "3790",
      "volume": "11",
      "author": "Li J. J.",
      "year": "2003",
      "journal-title": "Bioorg. Med. Chem."
    },
    {
      "key": "jm049499ob00034/jm049499ob00034_1",
      "unstructured": "Sterling Drug, Inc. 3,3-Dichloro-2-oxopolymethylimines. 1970, GB1192670."
    },
    {
      "key": "jm049499ob00035/jm049499ob00035_1",
      "doi-asserted-by": "crossref",
      "first-page": "705",
      "DOI": "10.1002/jhet.5570310401",
      "volume": "31",
      "author": "Cziaky Z.",
      "year": "1994",
      "journal-title": "J. Heterocycl. Chem."
    },
    {
      "key": "jm049499ob00036/jm049499ob00036_1",
      "volume-title": "Preparation of benzoxepinecarboxamides, benzocycloheptenecarboxamides, and related compounds as CCR5 antagonists. PCT Int. Appl",
      "author": "Nishimura O.",
      "year": "1999"
    },
    {
      "key": "jm049499ob00037/jm049499ob00037_1",
      "doi-asserted-by": "crossref",
      "first-page": "46",
      "DOI": "10.1002/cber.19490820110",
      "volume": "82",
      "author": "Henecka H",
      "year": "1949",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "jm049499ob00038/jm049499ob00038_1",
      "doi-asserted-by": "crossref",
      "first-page": "477",
      "DOI": "10.1021/jo026203i",
      "volume": "68",
      "author": "Dormer P.",
      "year": "2003",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "jm049499ob00039/jm049499ob00039_1",
      "doi-asserted-by": "crossref",
      "first-page": "1694",
      "DOI": "10.1021/jf00021a042",
      "volume": "40",
      "author": "Hara T.",
      "year": "1992",
      "journal-title": "J. Agric. Food. Chem."
    },
    {
      "key": "jm049499ob00040/jm049499ob00040_1",
      "first-page": "23",
      "volume": "17",
      "author": "Gnanasekaran S. J. R.",
      "year": "1993",
      "journal-title": "Sulfur Lett."
    },
    {
      "key": "jm049499ob00041/jm049499ob00041_1",
      "doi-asserted-by": "crossref",
      "first-page": "1093",
      "DOI": "10.1124/mol.63.5.1082",
      "volume": "63",
      "author": "Lavreysen H.",
      "year": "2003",
      "journal-title": "Mol. Pharmacol."
    },
    {
      "issue": "7",
      "key": "jm049499ob00042/jm049499ob00042_1",
      "doi-asserted-by": "crossref",
      "first-page": "972",
      "DOI": "10.1016/j.neuropharm.2004.08.007",
      "volume": "47",
      "author": "Lavreysen H.",
      "year": "2004",
      "journal-title": "Neuropharmacol."
    },
    {
      "key": "jm049499ob00043/jm049499ob00043_1",
      "volume-title": "Effects of mGlu1 receptor blockade on anxiety-related behaviour in the rat lick suppression test. Psychopharmacol",
      "author": "Steckler T.",
      "year": "2004"
    },
    {
      "issue": "31",
      "key": "jm049499ob00045/jm049499ob00045_1",
      "first-page": "5464",
      "volume": "36",
      "author": "Williams J. M.",
      "year": "1995",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "jm049499ob00046/jm049499ob00046_1",
      "unstructured": "Edwards, P. N.; Waterson, D. \u03b1,\u03b1-Dialkylbenzyl derivatives containing aromatic and heteroaromatic nuclei and their preparation and use as 5-lipoxygenase inhibitors. Eur. Pat. Appl. 1992, EP 505122."
    },
    {
      "issue": "24",
      "key": "jm049499ob00047/jm049499ob00047_1",
      "doi-asserted-by": "crossref",
      "first-page": "5257",
      "DOI": "10.1021/jm030327l",
      "volume": "46",
      "author": "Perner R. J.",
      "year": "2003",
      "journal-title": "J. Med. Chem."
    },
    {
      "key": "jm049499ob00048/jm049499ob00048_1",
      "doi-asserted-by": "crossref",
      "first-page": "1254",
      "DOI": "10.1124/mol.61.5.1244",
      "volume": "61",
      "author": "Lavreysen H.",
      "year": "2002",
      "journal-title": "Mol. Pharmacol."
    },
    {
      "key": "jm049499ob00049/jm049499ob00049_1",
      "doi-asserted-by": "crossref",
      "first-page": "562",
      "DOI": "10.1016/S0009-9236(97)90135-1",
      "volume": "61",
      "author": "Iatsimirskaia E.",
      "year": "1997",
      "journal-title": "Clin. Pharmacol. Ther."
    }
  ],
  "container-title": "Journal of Medicinal Chemistry",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://pubs.acs.org/doi/pdf/10.1021/jm049499o",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        24
      ]
    ],
    "date-time": "2024-01-24T03:04:07Z",
    "timestamp": 1706065447000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://pubs.acs.org/doi/10.1021/jm049499o"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2005,
        1,
        28
      ]
    ]
  },
  "references-count": 48,
  "journal-issue": {
    "issue": "6",
    "published-print": {
      "date-parts": [
        [
          2005,
          3,
          1
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1021/jm049499o"
  ],
  "URL": "http://dx.doi.org/10.1021/jm049499o",
  "relation": {},
  "ISSN": [
    "0022-2623",
    "1520-4804"
  ],
  "subject": [],
  "container-title-short": "J. Med. Chem.",
  "published": {
    "date-parts": [
      [
        2005,
        1,
        28
      ]
    ]
  }
}