CA2587141A1 - Derives d'octahydropyrrolo[3,4-c]pyrrole - Google Patents

Info

Publication number

CA2587141A1

CA2587141A1 CA002587141A CA2587141A CA2587141A1 CA 2587141 A1 CA2587141 A1 CA 2587141A1 CA 002587141 A CA002587141 A CA 002587141A CA 2587141 A CA2587141 A CA 2587141A CA 2587141 A1 CA2587141 A1 CA 2587141A1

Authority

CA

Canada

Prior art keywords

cndot

formula

compound

inhibitors

preparation

Prior art date

2004-11-24

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical class C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 title abstract description 5
• 238000000034 method Methods 0.000 claims abstract description 100
• 239000000203 mixture Substances 0.000 claims abstract description 75
• 230000008569 process Effects 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 233
• -1 trifluoromethoxy, hydroxy Chemical group 0.000 claims description 53
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• ZVFSYTFFWGYEMM-UHFFFAOYSA-N 2-(trichloromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(Cl)(Cl)Cl)=NC2=C1 ZVFSYTFFWGYEMM-UHFFFAOYSA-N 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 26
• 229910021529 ammonia Inorganic materials 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 19
• 239000003446 ligand Substances 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
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• 229940044551 receptor antagonist Drugs 0.000 claims description 9
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• 239000005557 antagonist Substances 0.000 claims description 8
• 230000008878 coupling Effects 0.000 claims description 7
• 238000010168 coupling process Methods 0.000 claims description 7
• 238000005859 coupling reaction Methods 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
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• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
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• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 4
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
• ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 3
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• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims description 3
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
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• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
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• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims description 3
• GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 claims description 3
• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 3
• OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 claims description 3
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 3
• JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 3
• 229960003088 loratadine Drugs 0.000 claims description 3
• 229960005127 montelukast Drugs 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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• 208000023504 respiratory system disease Diseases 0.000 claims description 3
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• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 2
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 2
• 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 claims description 2
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• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 2
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