TWI374883B - Crystalline form of a biphenyl compound - Google Patents

Info

Publication number

TWI374883B

TWI374883B TW094126435A TW94126435A TWI374883B TW I374883 B TWI374883 B TW I374883B TW 094126435 A TW094126435 A TW 094126435A TW 94126435 A TW94126435 A TW 94126435A TW I374883 B TWI374883 B TW I374883B

Authority

TW

Taiwan

Prior art keywords

compound

acid

hydroxy

ethyl

oxo

Prior art date

2004-08-16

Links

• Espacenet
• Global Dossier
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• -1 biphenyl compound Chemical class 0.000 title claims description 73
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 9
• 239000004305 biphenyl Substances 0.000 title claims description 5
• 235000010290 biphenyl Nutrition 0.000 title claims description 5
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 238000000034 method Methods 0.000 claims abstract description 70
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 49
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical class OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims abstract description 29
• 208000019693 Lung disease Diseases 0.000 claims abstract description 18
• 230000008569 process Effects 0.000 claims abstract description 12
• 150000001875 compounds Chemical class 0.000 claims description 144
• 239000000203 mixture Substances 0.000 claims description 112
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 76
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 61
• 239000013078 crystal Substances 0.000 claims description 55
• 238000002360 preparation method Methods 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
• 239000002253 acid Substances 0.000 claims description 38
• 239000003814 drug Substances 0.000 claims description 27
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
• 239000000843 powder Substances 0.000 claims description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 17
• 238000010521 absorption reaction Methods 0.000 claims description 16
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 16
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 16
• 150000003431 steroids Chemical class 0.000 claims description 15
• AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims description 14
• 238000002844 melting Methods 0.000 claims description 14
• 230000008018 melting Effects 0.000 claims description 14
• SQHCCAHZYMQIOG-UHFFFAOYSA-N C1(=C(C=CC=C1)NNC(O)=O)C1=CC=CC=C1 Chemical compound C1(=C(C=CC=C1)NNC(O)=O)C1=CC=CC=C1 SQHCCAHZYMQIOG-UHFFFAOYSA-N 0.000 claims description 13
• QMOVGVNKXUTCQU-UHFFFAOYSA-N (2-phenylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-N 0.000 claims description 12
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 239000003701 inert diluent Substances 0.000 claims description 11
• GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 11
• 239000000052 vinegar Substances 0.000 claims description 10
• 208000006673 asthma Diseases 0.000 claims description 9
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• XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
• 238000001816 cooling Methods 0.000 claims description 7
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 6
• 229920002472 Starch Polymers 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 6
• 235000019698 starch Nutrition 0.000 claims description 6
• 238000000862 absorption spectrum Methods 0.000 claims description 5
• 239000008107 starch Substances 0.000 claims description 5
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 4
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 239000008103 glucose Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• 239000004626 polylactic acid Substances 0.000 claims description 3
• POUWTFMTECJTGQ-UHFFFAOYSA-N CCCCCCCCC(C(O)=O)NC(C=CC=C1)=C1C1=CC=CC=C1 Chemical compound CCCCCCCCC(C(O)=O)NC(C=CC=C1)=C1C1=CC=CC=C1 POUWTFMTECJTGQ-UHFFFAOYSA-N 0.000 claims description 2
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
• 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
• 238000007670 refining Methods 0.000 claims description 2
• 150000005846 sugar alcohols Chemical class 0.000 claims description 2
• 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 claims description 2
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
• IHTNRDIBNXBSIF-UHFFFAOYSA-N 2-ethyloxane Chemical compound CCC1CCCCO1 IHTNRDIBNXBSIF-UHFFFAOYSA-N 0.000 claims 1
• 235000009508 confectionery Nutrition 0.000 claims 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
• 229940102396 methyl bromide Drugs 0.000 claims 1
• 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims 1
• 239000012453 solvate Substances 0.000 abstract description 25
• 239000000543 intermediate Substances 0.000 abstract description 2
• URWYQGVSPQJGGB-DHUJRADRSA-N [1-[3-[2-chloro-4-[[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]methyl]-5-methoxyanilino]-3-oxopropyl]piperidin-4-yl] n-(2-phenylphenyl)carbamate Chemical compound ClC=1C=C(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)C(OC)=CC=1NC(=O)CCN(CC1)CCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 URWYQGVSPQJGGB-DHUJRADRSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 239000000243 solution Substances 0.000 description 61
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• 238000004458 analytical method Methods 0.000 description 37
• 210000004027 cell Anatomy 0.000 description 37
• 239000000047 product Substances 0.000 description 35
• 235000019439 ethyl acetate Nutrition 0.000 description 33
• 238000012360 testing method Methods 0.000 description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
• 238000003556 assay Methods 0.000 description 27
• 238000009472 formulation Methods 0.000 description 24
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
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• 210000000170 cell membrane Anatomy 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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