JPH05508836A - シグマ受容体に対して高い結合性を有する置換グアニジンおよびその使用 - Google Patents
シグマ受容体に対して高い結合性を有する置換グアニジンおよびその使用Info
- Publication number
- JPH05508836A JPH05508836A JP91510984A JP51098491A JPH05508836A JP H05508836 A JPH05508836 A JP H05508836A JP 91510984 A JP91510984 A JP 91510984A JP 51098491 A JP51098491 A JP 51098491A JP H05508836 A JPH05508836 A JP H05508836A
- Authority
- JP
- Japan
- Prior art keywords
- guanidine
- carbon atoms
- tolyl
- exo
- iodophenyl
- 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.)
- Pending
Links
- 108010085082 sigma receptors Proteins 0.000 title claims description 115
- 230000027455 binding Effects 0.000 title claims description 93
- 150000002357 guanidines Chemical class 0.000 title claims description 32
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 408
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 203
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 200
- 229910052757 nitrogen Inorganic materials 0.000 claims description 153
- 150000001875 compounds Chemical class 0.000 claims description 120
- -1 N-(adamant-1-yl)-N'-(o-isopropylphenyl)guanidine N-(adamant-1-yl)-N'-(p-bromo-o-tolyl)guanidine Chemical compound 0.000 claims description 114
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 61
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- 210000004556 brain Anatomy 0.000 claims description 49
- 230000000694 effects Effects 0.000 claims description 48
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- 239000012528 membrane Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 230000000949 anxiolytic effect Effects 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000002837 carbocyclic group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
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- 241000700199 Cavia porcellus Species 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- VEGSEUJMFASKPM-UHFFFAOYSA-N 1,2-dibenzylguanidine Chemical compound C=1C=CC=CC=1CNC(=N)NCC1=CC=CC=C1 VEGSEUJMFASKPM-UHFFFAOYSA-N 0.000 claims description 11
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- JUNBYRXGWOTEEP-UHFFFAOYSA-N [C].NC(N)=N Chemical group [C].NC(N)=N JUNBYRXGWOTEEP-UHFFFAOYSA-N 0.000 claims description 10
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- HKQAANYYOSPWPM-UHFFFAOYSA-N 1,2-bis(1,2,3,4-tetrahydronaphthalen-1-yl)guanidine Chemical compound C1CCC2=CC=CC=C2C1NC(=N)NC1C2=CC=CC=C2CCC1 HKQAANYYOSPWPM-UHFFFAOYSA-N 0.000 claims description 8
- KTLUTBQGBABJDU-UHFFFAOYSA-N 1,2-bis(3-propylphenyl)guanidine Chemical compound CCCC1=CC=CC(NC(=N)NC=2C=C(CCC)C=CC=2)=C1 KTLUTBQGBABJDU-UHFFFAOYSA-N 0.000 claims description 8
- JFRVIRASSXIVLH-UHFFFAOYSA-N 2-tert-butyl-1-(2-iodophenyl)guanidine Chemical compound CC(C)(C)NC(=N)NC1=CC=CC=C1I JFRVIRASSXIVLH-UHFFFAOYSA-N 0.000 claims description 7
- 241000282412 Homo Species 0.000 claims description 7
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- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 7
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- AFWDFPQVQNRSJJ-UHFFFAOYSA-N 2-(1-adamantyl)-1-(2,4-difluorophenyl)guanidine Chemical compound FC1=CC(F)=CC=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 AFWDFPQVQNRSJJ-UHFFFAOYSA-N 0.000 claims description 6
- OCUUDHBWYKCRGO-UHFFFAOYSA-N 2-(1-adamantyl)-1-[2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC=CC=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 OCUUDHBWYKCRGO-UHFFFAOYSA-N 0.000 claims description 6
- OGAVVWZTKYWFNT-UHFFFAOYSA-N 2-(3,5-dimethyl-1-adamantyl)-1-(2-iodophenyl)guanidine Chemical compound C1C(C)(C2)CC(C3)CC1(C)CC32NC(=N)NC1=CC=CC=C1I OGAVVWZTKYWFNT-UHFFFAOYSA-N 0.000 claims description 6
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- JYQMCTXRNGINFZ-UHFFFAOYSA-N 1-(4-bromo-2-methylphenyl)-2-cyclohexylguanidine Chemical compound CC1=CC(Br)=CC=C1NC(=N)NC1CCCCC1 JYQMCTXRNGINFZ-UHFFFAOYSA-N 0.000 claims description 5
- AGGSMRWOSSYYHD-UHFFFAOYSA-N 2-(2-adamantyl)-1-(2-iodophenyl)guanidine Chemical compound IC1=CC=CC=C1NC(=N)NC1C(C2)CC3CC2CC1C3 AGGSMRWOSSYYHD-UHFFFAOYSA-N 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 5
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- YSFOTGFAHZYTEJ-UHFFFAOYSA-N 1,2-bis(4-bromo-2-methylphenyl)guanidine Chemical compound CC1=CC(Br)=CC=C1NC(=N)NC1=CC=C(Br)C=C1C YSFOTGFAHZYTEJ-UHFFFAOYSA-N 0.000 claims description 4
- MPUAUPQFSLHOHQ-UHFFFAOYSA-N 1,2-dicyclohexylguanidine Chemical compound C1CCCCC1NC(=N)NC1CCCCC1 MPUAUPQFSLHOHQ-UHFFFAOYSA-N 0.000 claims description 4
- DMKHPJQTKYTAQN-UHFFFAOYSA-N 1,3-bis(3-ethylphenyl)imidazolidin-2-imine Chemical compound CCC1=CC=CC(N2C(N(CC2)C=2C=C(CC)C=CC=2)=N)=C1 DMKHPJQTKYTAQN-UHFFFAOYSA-N 0.000 claims description 4
- METBKYNDHDGJGY-UHFFFAOYSA-N 2-(1-adamantyl)-1-(2-nitrophenyl)guanidine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 METBKYNDHDGJGY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 230000002285 radioactive effect Effects 0.000 claims description 4
- XZGRNYZXYCNDHI-UHFFFAOYSA-N 1-(2-iodophenyl)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1NC(=N)NC1=CC=CC=C1I XZGRNYZXYCNDHI-UHFFFAOYSA-N 0.000 claims description 3
- HREBFKCZFOECGR-UHFFFAOYSA-N 2-(1-adamantyl)-1-[4-fluoro-2-(trifluoromethyl)phenyl]guanidine Chemical compound FC(F)(F)C1=CC(F)=CC=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 HREBFKCZFOECGR-UHFFFAOYSA-N 0.000 claims description 3
- 230000004064 dysfunction Effects 0.000 claims description 3
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- 230000001105 regulatory effect Effects 0.000 claims description 3
- SAPQZYMPGUOQOF-UHFFFAOYSA-N 1,2-bis(2-iodophenyl)guanidine Chemical compound IC1=CC=CC=C1NC(=N)NC1=CC=CC=C1I SAPQZYMPGUOQOF-UHFFFAOYSA-N 0.000 claims description 2
- RIAXXCQKICATHW-UHFFFAOYSA-N 1,2-bis(3-methylphenyl)guanidine Chemical compound CC1=CC=CC(NC(=N)NC=2C=C(C)C=CC=2)=C1 RIAXXCQKICATHW-UHFFFAOYSA-N 0.000 claims description 2
- PGCGCFBAHRVIIN-UHFFFAOYSA-N 1,3-bis(2-methylphenyl)imidazolidin-2-imine Chemical compound CC1=CC=CC=C1N1C(=N)N(C=2C(=CC=CC=2)C)CC1 PGCGCFBAHRVIIN-UHFFFAOYSA-N 0.000 claims description 2
- WDYCWJKRDHPOMN-UHFFFAOYSA-N 1-(5-bromo-2-methyl-4-nitrophenyl)-2-(4,5-dibromo-2-methylphenyl)guanidine Chemical compound CC1=CC([N+]([O-])=O)=C(Br)C=C1NC(N)=NC1=CC(Br)=C(Br)C=C1C WDYCWJKRDHPOMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 claims description 2
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- DZPXQGGBMZBZNI-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)methyl]guanidine Chemical compound CC1=CC=CC=C1CNC(=N)NCC1=CC=CC=C1C DZPXQGGBMZBZNI-UHFFFAOYSA-N 0.000 claims 5
- FYZGFWOIQSITSW-UHFFFAOYSA-N 1-(5-bromo-2-methylphenyl)-2-cyclohexylguanidine Chemical compound CC1=CC=C(Br)C=C1NC(=N)NC1CCCCC1 FYZGFWOIQSITSW-UHFFFAOYSA-N 0.000 claims 5
- NSOJADJSIOHGHB-UHFFFAOYSA-N 2-(3,5-dimethyl-1-adamantyl)-1-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1NC(=N)NC1(C2)CC(C)(C3)CC2(C)CC3C1 NSOJADJSIOHGHB-UHFFFAOYSA-N 0.000 claims 4
- HNCJNENNFGMRQN-UHFFFAOYSA-N 1-(2-methyl-5-nitrophenyl)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1NC(=N)NC1=CC([N+]([O-])=O)=CC=C1C HNCJNENNFGMRQN-UHFFFAOYSA-N 0.000 claims 3
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- XAKPVTYBFUZSJC-UHFFFAOYSA-N 2-(1-adamantyl)-1-(2-propan-2-ylphenyl)guanidine Chemical compound CC(C)C1=CC=CC=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 XAKPVTYBFUZSJC-UHFFFAOYSA-N 0.000 claims 2
- HIKWVLDGBVMKQK-UHFFFAOYSA-N CC1=CC=C(Br)C=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 Chemical compound CC1=CC=C(Br)C=C1NC(=N)NC1(C2)CC(C3)CC2CC3C1 HIKWVLDGBVMKQK-UHFFFAOYSA-N 0.000 claims 2
- 101100108551 Mus musculus Akr1b7 gene Proteins 0.000 claims 2
- CDKJFRLFTVPCDI-UHFFFAOYSA-N 1,2-bis(2,3-dihydro-1h-inden-4-yl)guanidine Chemical compound C=1C=CC=2CCCC=2C=1NC(=N)NC1=CC=CC2=C1CCC2 CDKJFRLFTVPCDI-UHFFFAOYSA-N 0.000 claims 1
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- XPMPUPIXGHJYCO-UHFFFAOYSA-N 2-(1-adamantyl)-1-(2-oxochromen-6-yl)guanidine Chemical compound C1C(C2)CC(C3)CC2CC13N=C(N)NC1=CC=C(OC(=O)C=C2)C2=C1 XPMPUPIXGHJYCO-UHFFFAOYSA-N 0.000 claims 1
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- CKLOSYYAFRUXFF-UHFFFAOYSA-N 2-cyclohexyl-1-(4-iodophenyl)guanidine Chemical compound C1=CC(I)=CC=C1NC(=N)NC1CCCCC1 CKLOSYYAFRUXFF-UHFFFAOYSA-N 0.000 claims 1
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- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/12—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
- C07C2603/64—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings having a tricyclo[2.2.1.0(2,6)]heptstructure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Liquid Crystal Display Device Control (AREA)
- Control Of Indicators Other Than Cathode Ray Tubes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52821690A | 1990-05-25 | 1990-05-25 | |
| US528,216 | 1990-05-25 | ||
| US65775991A | 1991-02-21 | 1991-02-21 | |
| US657,759 | 1991-02-21 | ||
| PCT/US1991/003594 WO1991018868A1 (en) | 1990-05-25 | 1991-05-22 | Substituted guanidines having high binding to the sigma receptor and the use thereof |
Publications (1)
| Publication Number | Publication Date |
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| JPH05508836A true JPH05508836A (ja) | 1993-12-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP91510984A Pending JPH05508836A (ja) | 1990-05-25 | 1991-05-22 | シグマ受容体に対して高い結合性を有する置換グアニジンおよびその使用 |
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| Country | Link |
|---|---|
| US (1) | US5574070A (enExample) |
| EP (1) | EP0532642A1 (enExample) |
| JP (1) | JPH05508836A (enExample) |
| AU (1) | AU653729B2 (enExample) |
| IE (1) | IE63076B1 (enExample) |
| PT (1) | PT97770B (enExample) |
| WO (1) | WO1991018868A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015522621A (ja) * | 2012-07-19 | 2015-08-06 | ドレクセル ユニバーシティ | 細胞タンパク質ホメオスタシスを調節するためのシグマ受容体リガンド |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5190976A (en) * | 1986-07-10 | 1993-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And University Of Oregon | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| ES2181668T3 (es) * | 1990-03-02 | 2003-03-01 | Oregon State | Guanidinas tri- y tetra-substituidas y su uso como antagonistas de aminoacido excitador. |
| ATE186047T1 (de) * | 1991-02-08 | 1999-11-15 | Cambridge Neuroscience Res | Substituierte guanidine und derivate hiervon als modulatoren der freisetzung von neurotransmittern und neue methode zur identifizierung von inhibitoren der neurotransmitter-freisetzung |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| CN1188121C (zh) * | 1993-05-27 | 2005-02-09 | 剑桥神经科学公司 | 治疗性取代的胍类 |
| WO1995014467A1 (en) * | 1993-11-22 | 1995-06-01 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| KR100424523B1 (ko) * | 1993-11-23 | 2004-09-30 | 캠브리지 뉴로사이언스, 인코포레이티드 | 치료용의치환된구아니딘 |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| JPH09509156A (ja) | 1994-02-03 | 1997-09-16 | ケンブリッジ・ニューロサイエンス・インコーポレーテッド | 治療用グアニジン類 |
| WO1995023132A1 (en) * | 1994-02-23 | 1995-08-31 | Cambridge Neuroscience, Inc. | Blockers of ion channels and methods of use thereof |
| US6774263B1 (en) | 1997-10-10 | 2004-08-10 | Cambridge Neuroscience, Inc. | Pharmaceutically active compound and methods of use |
| WO2000001676A1 (en) * | 1998-07-02 | 2000-01-13 | Neurosearch A/S | Potassium channel blocking agents |
| US6194447B1 (en) | 1998-07-02 | 2001-02-27 | Neurosearch A/S | Bis (benzimidazole) derivatives serving as potassium blocking agents |
| US6875759B1 (en) | 1999-07-21 | 2005-04-05 | Kadmus Pharmaceuticals | Substituted guanidines and the use thereof |
| ITTO20030668A1 (it) | 2003-09-02 | 2005-03-03 | Rotta Res Lab S P A O Ra Rottapharm | Derivati dell'adamantano dotati di attivita' neuroprotettiva, antidepressiva e anti-ischemica e procedimento per la loro preparazione. |
| WO2007022964A2 (de) | 2005-08-24 | 2007-03-01 | Abbott Gmbh & Co. Kg | Hetaryl substituierte guanidinverbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| CA2651862A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7998971B2 (en) * | 2006-09-08 | 2011-08-16 | Braincells Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US11117870B2 (en) | 2017-11-01 | 2021-09-14 | Drexel University | Compounds, compositions, and methods for treating diseases |
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| HU180240B (en) * | 1978-04-21 | 1983-02-28 | Gyogyszerkutato Intezet | Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines |
| CA1173037A (en) * | 1980-03-01 | 1984-08-21 | John L. Archibald | Piperidino ureas as antidepressants |
| FR2509724B1 (fr) * | 1981-07-15 | 1985-10-25 | Centre Nat Rech Scient | Nouvelles guanidines a fort encombrement sterique et procedes pour leur preparation |
| US4400383A (en) * | 1981-12-11 | 1983-08-23 | Burroughs Wellcome Co. | Treatment of anxiety |
| US4575514A (en) * | 1982-12-20 | 1986-03-11 | Mcneilab, Inc. | Anxiety alleviating compositions containing loweralkyl-N-[amino(arylaminocarbonyl)-iminomethyl]-N-methylglycinates |
| US4663263A (en) * | 1984-10-19 | 1987-05-05 | Canon Kabushiki Kaisha | Toner, charge-imparting material and composition containing substituted guanidine compound for electrophotography |
| DE3501383A1 (de) * | 1985-01-17 | 1986-07-17 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von n,n'-disubstituierten guanidinen |
| EP0259371B1 (en) * | 1986-01-28 | 1992-05-13 | JOHN WYETH & BROTHER LIMITED | Preparation of 3-dimethylamino-7-methyl-1,2,4-benzotriazine-1-oxide and azapropazone |
| US4906779A (en) * | 1986-07-10 | 1990-03-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5190976A (en) * | 1986-07-10 | 1993-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And University Of Oregon | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US4709094A (en) * | 1986-07-10 | 1987-11-24 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Sigma brain receptor ligands and their use |
| US5093525A (en) * | 1986-07-10 | 1992-03-03 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
| AU642881B2 (en) * | 1989-05-02 | 1993-11-04 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Methods for treating anxiety with sigma receptor ligands |
-
1991
- 1991-05-22 EP EP91911414A patent/EP0532642A1/en not_active Withdrawn
- 1991-05-22 US US07/952,849 patent/US5574070A/en not_active Expired - Lifetime
- 1991-05-22 WO PCT/US1991/003594 patent/WO1991018868A1/en not_active Ceased
- 1991-05-22 AU AU80032/91A patent/AU653729B2/en not_active Ceased
- 1991-05-22 JP JP91510984A patent/JPH05508836A/ja active Pending
- 1991-05-23 IE IE177691A patent/IE63076B1/en not_active IP Right Cessation
- 1991-05-24 PT PT97770A patent/PT97770B/pt not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015522621A (ja) * | 2012-07-19 | 2015-08-06 | ドレクセル ユニバーシティ | 細胞タンパク質ホメオスタシスを調節するためのシグマ受容体リガンド |
| JP2019006800A (ja) * | 2012-07-19 | 2019-01-17 | ドレクセル ユニバーシティ | 細胞タンパク質ホメオスタシスを調節するためのシグマ受容体リガンド |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8003291A (en) | 1991-12-31 |
| US5574070A (en) | 1996-11-12 |
| AU653729B2 (en) | 1994-10-13 |
| IE911776A1 (en) | 1991-12-04 |
| EP0532642A4 (enExample) | 1994-04-27 |
| EP0532642A1 (en) | 1993-03-24 |
| IE63076B1 (en) | 1995-03-22 |
| PT97770A (pt) | 1992-06-30 |
| WO1991018868A1 (en) | 1991-12-12 |
| PT97770B (pt) | 1998-10-30 |
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