NO115473B - - Google Patents
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- Publication number
- NO115473B NO115473B NO154363A NO15436364A NO115473B NO 115473 B NO115473 B NO 115473B NO 154363 A NO154363 A NO 154363A NO 15436364 A NO15436364 A NO 15436364A NO 115473 B NO115473 B NO 115473B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- reaction
- carbon atoms
- hydrogen
- alkali metal
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 1-substituted cycloheptimidazol-2(1H)-one compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006515 benzyloxy alkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 13
- HBNPHVRKFGNYAV-UHFFFAOYSA-N 1h-cyclohepta[d]imidazol-2-one Chemical class C1=CC=CC=C2NC(=O)N=C21 HBNPHVRKFGNYAV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 229920002307 Dextran Polymers 0.000 description 6
- 230000036592 analgesia Effects 0.000 description 6
- 239000002178 crystalline material Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- AUMRVQKZNCFQJE-UHFFFAOYSA-N 1-prop-2-ynylcyclohepta[d]imidazol-2-one Chemical compound C(C#C)N1C(N=C2C1=CC=CC=C2)=O AUMRVQKZNCFQJE-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 208000000114 Pain Threshold Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002026 chloroform extract Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000037040 pain threshold Effects 0.000 description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UXQAMMYAMVOCDO-UHFFFAOYSA-N 1-(methoxymethyl)cyclohepta[d]imidazol-2-one Chemical compound COCN1C(N=C2C1=CC=CC=C2)=O UXQAMMYAMVOCDO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- AQCHNOYSJOYZKM-UHFFFAOYSA-N C(=C)N1C(N=C2C1=CC=CC=C2)=O Chemical compound C(=C)N1C(N=C2C1=CC=CC=C2)=O AQCHNOYSJOYZKM-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- LADPCMZCENPFGV-UHFFFAOYSA-N chloromethoxymethylbenzene Chemical compound ClCOCC1=CC=CC=C1 LADPCMZCENPFGV-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4028462 | 1962-09-17 | ||
| JP4296763 | 1963-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115473B true NO115473B (xx) | 1968-10-14 |
Family
ID=26379735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO154363A NO115473B (xx) | 1962-09-17 | 1964-08-12 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3293260A (xx) |
| AT (1) | AT252910B (xx) |
| BE (1) | BE637407A (xx) |
| BR (1) | BR6352573D0 (xx) |
| CH (2) | CH451166A (xx) |
| DE (2) | DE1470251A1 (xx) |
| DK (1) | DK103778C (xx) |
| FR (1) | FR3720M (xx) |
| GB (2) | GB1062563A (xx) |
| NL (1) | NL6409315A (xx) |
| NO (1) | NO115473B (xx) |
| SE (1) | SE308114B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
| US3488353A (en) * | 1967-05-29 | 1970-01-06 | Sterling Drug Inc | New 1-((2-azaindolyl)-lower-alkyl) 4-substituted-piperazines |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA631296A (en) * | 1961-11-21 | L. Clark Robert | Substituted benzimidazolones | |
| US2965648A (en) * | 1960-12-20 | Certain i-alkenyl benzimidazoles | ||
| US2623879A (en) * | 1950-11-27 | 1952-12-30 | Chemstrand Corp | Substituted benzimidazoles |
| US2944062A (en) * | 1957-07-17 | 1960-07-05 | Ciba Pharm Prod Inc | Certain alpha (1-diethylaminoethyl) benzimidazolyl (2), alpha-aryl acetamides |
| US3073841A (en) * | 1960-09-15 | 1963-01-15 | Geigy Chem Corp | Certain 1-imidazolinyl methyl, 2-aryl benzimidazoles |
| BE624446A (fr) * | 1961-11-07 | 1963-03-01 | Sankyo Co | Composés chimiques nouveaux du type cyloheptimidazol-2(1H)-ones monosubstitués. |
-
1963
- 1963-09-03 GB GB34810/63A patent/GB1062563A/en not_active Expired
- 1963-09-06 BR BR152573/63A patent/BR6352573D0/pt unknown
- 1963-09-10 US US307808A patent/US3293260A/en not_active Expired - Lifetime
- 1963-09-16 BE BE637407A patent/BE637407A/fr unknown
- 1963-09-16 DK DK435463AA patent/DK103778C/da active
- 1963-09-16 DE DE19631470251 patent/DE1470251A1/de active Pending
- 1963-09-17 AT AT747363A patent/AT252910B/de active
- 1963-09-17 CH CH1144663A patent/CH451166A/de unknown
-
1964
- 1964-08-11 CH CH1050264A patent/CH454155A/de unknown
- 1964-08-12 NO NO154363A patent/NO115473B/no unknown
- 1964-08-13 NL NL6409315A patent/NL6409315A/xx unknown
- 1964-08-14 FR FR985195A patent/FR3720M/fr not_active Expired
- 1964-08-14 GB GB33181/64A patent/GB1073485A/en not_active Expired
- 1964-08-15 DE DE19641470290 patent/DE1470290A1/de active Pending
- 1964-08-17 SE SE9905/64A patent/SE308114B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1073485A (en) | 1967-06-28 |
| AT252910B (de) | 1967-03-10 |
| CH451166A (de) | 1968-05-15 |
| SE308114B (xx) | 1969-02-03 |
| BE637407A (fr) | 1964-01-16 |
| DK103778C (da) | 1966-02-21 |
| US3293260A (en) | 1966-12-20 |
| NL6409315A (xx) | 1965-02-17 |
| DE1470290A1 (de) | 1969-06-12 |
| BR6352573D0 (pt) | 1973-07-12 |
| GB1062563A (en) | 1967-03-22 |
| DE1470251A1 (de) | 1969-06-04 |
| CH454155A (de) | 1968-04-15 |
| FR3720M (fr) | 1965-11-29 |
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