TW200536478A - 2-halofuryl/thienyl-3-carboxamides - Google Patents

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Publication number

TW200536478A

TW200536478A TW094103287A TW94103287A TW200536478A TW 200536478 A TW200536478 A TW 200536478A TW 094103287 A TW094103287 A TW 094103287A TW 94103287 A TW94103287 A TW 94103287A TW 200536478 A TW200536478 A TW 200536478A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

formula

cycloalkyl

substituted

Prior art date

2004-02-06

Links

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• 238000000034 method Methods 0.000 claims abstract description 129
• 244000005700 microbiome Species 0.000 claims abstract description 18
• -1 cvcv haloyloxy Chemical group 0.000 claims description 315
• 125000000217 alkyl group Chemical group 0.000 claims description 159
• 239000007789 gas Substances 0.000 claims description 92
• 239000011737 fluorine Substances 0.000 claims description 77
• 229910052731 fluorine Inorganic materials 0.000 claims description 77
• 238000006243 chemical reaction Methods 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 74
• 239000002253 acid Substances 0.000 claims description 70
• 239000001257 hydrogen Substances 0.000 claims description 64
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
• 229910052794 bromium Inorganic materials 0.000 claims description 45
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 42
• 125000000304 alkynyl group Chemical group 0.000 claims description 41
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 40
• 239000003085 diluting agent Substances 0.000 claims description 40
• 125000004432 carbon atom Chemical group C* 0.000 claims description 38
• 239000000460 chlorine Substances 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 125000001188 haloalkyl group Chemical group 0.000 claims description 36
• 150000001412 amines Chemical group 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
• 239000000203 mixture Substances 0.000 claims description 33
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
• 125000004414 alkyl thio group Chemical group 0.000 claims description 30
• 239000003054 catalyst Substances 0.000 claims description 30
• 239000003795 chemical substances by application Substances 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
• 239000011593 sulfur Substances 0.000 claims description 30
• 229910052717 sulfur Inorganic materials 0.000 claims description 30
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 29
• 125000001246 bromo group Chemical group Br* 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 29
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 26
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 239000001301 oxygen Substances 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 238000006467 substitution reaction Methods 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
• 125000004992 haloalkylamino group Chemical group 0.000 claims description 19
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 19
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 239000011630 iodine Substances 0.000 claims description 15
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 15
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
• 239000011230 binding agent Substances 0.000 claims description 14
• 125000001475 halogen functional group Chemical group 0.000 claims description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 11
• 150000004820 halides Chemical class 0.000 claims description 11
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 11
• 150000002430 hydrocarbons Chemical group 0.000 claims description 11
• 150000002576 ketones Chemical class 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 229910052763 palladium Inorganic materials 0.000 claims description 10
• 241000894007 species Species 0.000 claims description 10
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 229910052742 iron Inorganic materials 0.000 claims description 9
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
• WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 229910052786 argon Inorganic materials 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
• 150000001336 alkenes Chemical class 0.000 claims description 5
• 150000004985 diamines Chemical class 0.000 claims description 5
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 5
• 229910052698 phosphorus Inorganic materials 0.000 claims description 5
• 239000011574 phosphorus Substances 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
• 239000004606 Fillers/Extenders Substances 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
• 238000006297 dehydration reaction Methods 0.000 claims description 3
• 230000002452 interceptive effect Effects 0.000 claims description 3
• 125000005429 oxyalkyl group Chemical group 0.000 claims description 3
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
• 241001674048 Phthiraptera Species 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 2
• 239000011733 molybdenum Substances 0.000 claims description 2
• 229910052750 molybdenum Inorganic materials 0.000 claims description 2
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 21
• 150000002431 hydrogen Chemical class 0.000 claims 11
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 1
• ZKXGQPQAMRSBOL-UHFFFAOYSA-N 1,2,3-trifluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=C(F)C(F)=C2F ZKXGQPQAMRSBOL-UHFFFAOYSA-N 0.000 claims 1
• KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 1
• XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 claims 1
• CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims 1
• 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
• 238000005660 chlorination reaction Methods 0.000 claims 1
• 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
• 210000004513 dentition Anatomy 0.000 claims 1
• 125000004983 dialkoxyalkyl group Chemical group 0.000 claims 1
• 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
• 125000000262 haloalkenyl group Chemical group 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
• 229950004864 olamine Drugs 0.000 claims 1
• 125000004660 phenylalkylthio group Chemical group 0.000 claims 1
• 150000004053 quinones Chemical class 0.000 claims 1
• 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
• 125000004354 sulfur functional group Chemical group 0.000 claims 1
• 125000004001 thioalkyl group Chemical group 0.000 claims 1
• 230000036346 tooth eruption Effects 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 158
• 230000008569 process Effects 0.000 abstract description 86
• 238000002360 preparation method Methods 0.000 abstract description 17
• 239000000543 intermediate Substances 0.000 abstract description 3
• 241000196324 Embryophyta Species 0.000 description 81
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
• 238000004519 manufacturing process Methods 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 54
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• 238000012360 testing method Methods 0.000 description 45
• 239000007858 starting material Substances 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
• 230000001681 protective effect Effects 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
• 239000002585 base Substances 0.000 description 23
• 229910052751 metal Inorganic materials 0.000 description 23
• 239000002184 metal Substances 0.000 description 23
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-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 19
• 125000001931 aliphatic group Chemical group 0.000 description 18
• 239000003208 petroleum Substances 0.000 description 18
• 241000233866 Fungi Species 0.000 description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
• BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 15
• GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 15
• 239000003960 organic solvent Substances 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 14
• 150000002170 ethers Chemical class 0.000 description 14
• 229940052303 ethers for general anesthesia Drugs 0.000 description 14
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 239000003995 emulsifying agent Substances 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 11
• QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 11
• 150000007513 acids Chemical class 0.000 description 11
• 150000001298 alcohols Chemical class 0.000 description 11
• MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
• 229960004592 isopropanol Drugs 0.000 description 11
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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