IL229246A - Partially saturated tricyclic compounds and preparation and use methods - Google Patents

Info

Publication number

IL229246A

IL229246A IL229246A IL22924613A IL229246A IL 229246 A IL229246 A IL 229246A IL 229246 A IL229246 A IL 229246A IL 22924613 A IL22924613 A IL 22924613A IL 229246 A IL229246 A IL 229246A

Authority

IL

Israel

Prior art keywords

6alkyl

carboxylic acid

chromene

mixture

group

Prior art date

2011-05-06

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 210
• 229920006395 saturated elastomer Polymers 0.000 title claims description 28
• 238000000034 method Methods 0.000 title description 55
• 239000000203 mixture Substances 0.000 claims description 595
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 273
• 239000002253 acid Substances 0.000 claims description 175
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 104
• 125000001424 substituent group Chemical group 0.000 claims description 86
• 125000000623 heterocyclic group Chemical group 0.000 claims description 79
• -1 cyano, hydroxyl Chemical group 0.000 claims description 65
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 239000001257 hydrogen Substances 0.000 claims description 61
• 229910052757 nitrogen Inorganic materials 0.000 claims description 60
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
• 229910052799 carbon Inorganic materials 0.000 claims description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
• 125000001153 fluoro group Chemical group F* 0.000 claims description 33
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 239000011737 fluorine Substances 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 208000008589 Obesity Diseases 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 125000002837 carbocyclic group Chemical group 0.000 claims description 9
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 25
• 235000019000 fluorine Nutrition 0.000 claims 19
• 150000002431 hydrogen Chemical class 0.000 claims 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 8
• 125000004043 oxo group Chemical group O=* 0.000 claims 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 101100521345 Mus musculus Prop1 gene Proteins 0.000 claims 2
• 108700017836 Prophet of Pit-1 Proteins 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• JPKYDPJLUANHKK-HFCFLWKCSA-N 5-[[2-[2-[(2s)-1-ethylpyrrolidin-2-yl]ethylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound CCN1CCC[C@H]1CCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O JPKYDPJLUANHKK-HFCFLWKCSA-N 0.000 claims 1
• WYSQERQGMBCNST-LRYGQEGESA-N 5-[[2-[2-[(3r)-1-ethylpyrrolidin-3-yl]ethylamino]phenyl]sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid Chemical compound C1N(CC)CC[C@H]1CCNC1=CC=CC=C1S(=O)(=O)NC1=CC=C(C2C(C2)CO2)C2=C1C(O)=O WYSQERQGMBCNST-LRYGQEGESA-N 0.000 claims 1
• QEQWVMSWYZCGKP-UHFFFAOYSA-N cyclopropa[c]chromene-4-carboxylic acid Chemical compound C12=CC2=COC2=C1C=CC=C2C(=O)O QEQWVMSWYZCGKP-UHFFFAOYSA-N 0.000 claims 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 340
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 315
• 239000000543 intermediate Substances 0.000 description 280
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 240
• 239000000243 solution Substances 0.000 description 188
• 239000000706 filtrate Substances 0.000 description 180
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 122
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 118
• 238000004587 chromatography analysis Methods 0.000 description 115
• 239000002904 solvent Substances 0.000 description 106
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
• 239000007787 solid Substances 0.000 description 69
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 68
• 238000011282 treatment Methods 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• 239000012044 organic layer Substances 0.000 description 56
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 52
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
• 239000002585 base Substances 0.000 description 48
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 47
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 46
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 41
• 239000011369 resultant mixture Substances 0.000 description 41
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• 206010033307 Overweight Diseases 0.000 description 37
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 36
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
• 239000012298 atmosphere Substances 0.000 description 32
• 239000003795 chemical substances by application Substances 0.000 description 31
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 31
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
• 150000007942 carboxylates Chemical class 0.000 description 26
• 239000003054 catalyst Substances 0.000 description 26
• 235000019253 formic acid Nutrition 0.000 description 26
• 238000010992 reflux Methods 0.000 description 26
• 239000011734 sodium Substances 0.000 description 26
• 229910052708 sodium Inorganic materials 0.000 description 26
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 25
• 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 25
• 229910052763 palladium Inorganic materials 0.000 description 25
• 229910000027 potassium carbonate Inorganic materials 0.000 description 25
• 239000000377 silicon dioxide Substances 0.000 description 25
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
• 238000000926 separation method Methods 0.000 description 23
• 238000006243 chemical reaction Methods 0.000 description 21
• 239000003921 oil Substances 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 19
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 19
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 18
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 18
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 18
• 238000002953 preparative HPLC Methods 0.000 description 18
• 239000000725 suspension Substances 0.000 description 18
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 17
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• 150000001412 amines Chemical class 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 14
• 239000002245 particle Substances 0.000 description 14
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
• 235000017557 sodium bicarbonate Nutrition 0.000 description 14
• 238000001816 cooling Methods 0.000 description 13
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• 239000003208 petroleum Substances 0.000 description 12
• 239000000523 sample Substances 0.000 description 12
• 239000003826 tablet Substances 0.000 description 12
• 239000002775 capsule Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 239000012312 sodium hydride Substances 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 241001465754 Metazoa Species 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 238000002474 experimental method Methods 0.000 description 9
• 239000012280 lithium aluminium hydride Substances 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 238000006722 reduction reaction Methods 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• 239000003039 volatile agent Substances 0.000 description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 229910021529 ammonia Inorganic materials 0.000 description 8
• 150000008064 anhydrides Chemical class 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 229940050176 methyl chloride Drugs 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
• 210000000577 adipose tissue Anatomy 0.000 description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 125000000524 functional group Chemical group 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• 150000002500 ions Chemical class 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 230000003647 oxidation Effects 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 239000001301 oxygen Substances 0.000 description 7
• NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• 239000011591 potassium Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 239000003643 water by type Substances 0.000 description 7
• 230000004580 weight loss Effects 0.000 description 7
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
• 239000007821 HATU Substances 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
• 150000001345 alkine derivatives Chemical group 0.000 description 6
• 125000003545 alkoxy group Chemical group 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• 229920002301 cellulose acetate Polymers 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000007800 oxidant agent Substances 0.000 description 6
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
• 239000012346 acetyl chloride Substances 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 229910052792 caesium Inorganic materials 0.000 description 5
• TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 5
• 230000000747 cardiac effect Effects 0.000 description 5
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