CY1423A

CY1423A - Novel amidines,processes for their manufacture,pharmaceutical preparations containing them,and their use

Novel amidines,processes for their manufacture,pharmaceutical preparations containing them,and their use Download PDF

Info

Publication number: CY1423A
Authority: CY; Cyprus
Prior art keywords: formula; salt; compound; indole; acetic acid
Prior art date: 1981-08-03

Application number

CY1423A

Other languages

English (en)

Original Assignee

Ciba Geigy Ag

Priority date

1981-08-03

Filing date

1988-09-02

Publication date

1988-09-02

1988-09-02 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1988-09-02 Publication of CY1423A publication Critical patent/CY1423A/en

Links

238000000034 method Methods 0.000 title claims abstract description 53
150000001409 amidines Chemical class 0.000 title claims abstract description 7
230000008569 process Effects 0.000 title claims description 37
238000004519 manufacturing process Methods 0.000 title claims description 16
239000000825 pharmaceutical preparation Substances 0.000 title abstract description 11
-1 carboxylic acid amidines Chemical class 0.000 claims abstract description 169
150000003839 salts Chemical class 0.000 claims abstract description 108
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 28
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims abstract description 27
229910052736 halogen Inorganic materials 0.000 claims abstract description 23
150000002367 halogens Chemical class 0.000 claims abstract description 23
125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 147
239000002253 acid Substances 0.000 claims description 81
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
239000007858 starting material Substances 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 19
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 15
239000011737 fluorine Substances 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
LNDWMQWLWGXEET-UHFFFAOYSA-N 2-(1h-indol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2NC=CC2=C1 LNDWMQWLWGXEET-UHFFFAOYSA-N 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
230000003647 oxidation Effects 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 11
238000003797 solvolysis reaction Methods 0.000 claims description 11
239000000543 intermediate Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
BBFZFOVPWAWNRA-UHFFFAOYSA-N ethyl 2-(1-thiophen-2-ylpyrimido[1,6-a]indol-5-yl)acetate Chemical compound N=1C=CC2=C(CC(=O)OCC)C3=CC=CC=C3N2C=1C1=CC=CS1 BBFZFOVPWAWNRA-UHFFFAOYSA-N 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
BMMWHLONFVRACH-UHFFFAOYSA-N ethyl 2-[7-methoxy-1-(pyridin-2-ylmethyl)pyrimido[1,6-a]indol-5-yl]acetate Chemical compound N=1C=CC2=C(CC(=O)OCC)C3=CC(OC)=CC=C3N2C=1CC1=CC=CC=N1 BMMWHLONFVRACH-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
QONDYZPOXVIVRI-UHFFFAOYSA-N 2-(1-thiophen-2-ylpyrimido[1,6-a]indol-5-yl)acetic acid Chemical compound N=1C=CC2=C(CC(=O)O)C3=CC=CC=C3N2C=1C1=CC=CS1 QONDYZPOXVIVRI-UHFFFAOYSA-N 0.000 claims description 2
PDMGSCUANDBAFH-UHFFFAOYSA-N 2-[7-methoxy-1-(pyridin-2-ylmethyl)pyrimido[1,6-a]indol-5-yl]acetic acid Chemical compound C=1C(OC)=CC=C(N23)C=1C(CC(O)=O)=C3C=CN=C2CC1=CC=CC=N1 PDMGSCUANDBAFH-UHFFFAOYSA-N 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 3
VGKWGHYHUAOYRU-UHFFFAOYSA-N 2-(1-phenylpyrimido[1,6-a]indol-5-yl)acetic acid Chemical compound N=1C=CC2=C(CC(=O)O)C3=CC=CC=C3N2C=1C1=CC=CC=C1 VGKWGHYHUAOYRU-UHFFFAOYSA-N 0.000 claims 1
DECAHEFANNFWPL-UHFFFAOYSA-N 2-[7-fluoro-1-(4-methylsulfinylphenyl)pyrimido[1,6-a]indol-5-yl]acetic acid Chemical compound C1=CC(S(=O)C)=CC=C1C1=NC=CC2=C(CC(O)=O)C3=CC(F)=CC=C3N12 DECAHEFANNFWPL-UHFFFAOYSA-N 0.000 claims 1
XZSYHLXEJZBLFQ-UHFFFAOYSA-N ethyl 2-(7-fluoro-1-thiophen-2-ylpyrimido[1,6-a]indol-5-yl)acetate Chemical compound N=1C=CC2=C(CC(=O)OCC)C3=CC(F)=CC=C3N2C=1C1=CC=CS1 XZSYHLXEJZBLFQ-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 23
239000003814 drug Substances 0.000 abstract description 3
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
150000007513 acids Chemical class 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000002585 base Substances 0.000 description 35
239000003054 catalyst Substances 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
239000003795 chemical substances by application Substances 0.000 description 29
239000000243 solution Substances 0.000 description 28
229910052500 inorganic mineral Inorganic materials 0.000 description 26
235000010755 mineral Nutrition 0.000 description 26
239000011707 mineral Substances 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000000203 mixture Substances 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
125000004043 oxo group Chemical group O=* 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
229910052783 alkali metal Inorganic materials 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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 14
239000001117 sulphuric acid Substances 0.000 description 14
235000011149 sulphuric acid Nutrition 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
238000009833 condensation Methods 0.000 description 13
230000005494 condensation Effects 0.000 description 13
235000011167 hydrochloric acid Nutrition 0.000 description 13
239000003826 tablet Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
235000014113 dietary fatty acids Nutrition 0.000 description 12
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
239000000194 fatty acid Substances 0.000 description 12
229930195729 fatty acid Natural products 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
230000002378 acidificating effect Effects 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
229920001223 polyethylene glycol Polymers 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
229920002472 Starch Polymers 0.000 description 10
150000008044 alkali metal hydroxides Chemical class 0.000 description 10
229930195733 hydrocarbon Natural products 0.000 description 10
150000002430 hydrocarbons Chemical class 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000000454 talc Substances 0.000 description 10
229910052623 talc Inorganic materials 0.000 description 10
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
239000008101 lactose Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
235000019698 starch Nutrition 0.000 description 9
238000003756 stirring Methods 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
238000006356 dehydrogenation reaction Methods 0.000 description 7
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150000002148 esters Chemical class 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
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239000011261 inert gas Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
235000011007 phosphoric acid Nutrition 0.000 description 7
235000011118 potassium hydroxide Nutrition 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000008107 starch Substances 0.000 description 7
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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239000001828 Gelatine Substances 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000010933 acylation Effects 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
239000013078 crystal Substances 0.000 description 6
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229920000159 gelatin Polymers 0.000 description 6
235000019322 gelatine Nutrition 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
239000003701 inert diluent Substances 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
150000007522 mineralic acids Chemical class 0.000 description 6
239000012071 phase Substances 0.000 description 6
229910052698 phosphorus Inorganic materials 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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239000000654 additive Substances 0.000 description 5
150000003973 alkyl amines Chemical class 0.000 description 5
239000002775 capsule Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
150000002191 fatty alcohols Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
239000002674 ointment Substances 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
239000011591 potassium Substances 0.000 description 5
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NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
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229910052751 metal Inorganic materials 0.000 description 4
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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239000012188 paraffin wax Substances 0.000 description 4
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UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
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