SA90100111B1 - طريقة لتحضير 7- مستبدل- حمض هبت-6- ينويك وحمض هبتانويك ومشتقات منها - Google Patents

طريقة لتحضير 7- مستبدل- حمض هبت-6- ينويك وحمض هبتانويك ومشتقات منها Download PDF

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Publication number: SA90100111B1
Authority: SA; Saudi Arabia
Prior art keywords: formula; compound; alkyl; butyl; ester
Prior art date: 1988-10-13

Application number

SA90100111A

Other languages

Arabic (ar)

English (en)

Inventor

كاو-مينق شين

برساد كوتيسوار كابا

جورج تى لى

اولجان ريبيك

د.بيتر هيس

د.ميشيل كريفويسير

Original Assignee

نوفارتيس ايه جي

Priority date (The priority date 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 date listed.)

1988-10-13

Filing date

1990-02-24

Publication date

2005-04-17

1990-02-24 Application filed by نوفارتيس ايه جي filed Critical نوفارتيس ايه جي

2005-04-17 Publication of SA90100111B1 publication Critical patent/SA90100111B1/ar

Links

238000000034 method Methods 0.000 title claims abstract description 128
239000002253 acid Substances 0.000 title claims description 33
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 278
229910052799 carbon Inorganic materials 0.000 claims abstract description 149
125000000217 alkyl group Chemical group 0.000 claims abstract description 116
239000001257 hydrogen Substances 0.000 claims abstract description 70
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
-1 7-substituted-hept-6-enoic acid Chemical class 0.000 claims abstract description 56
238000006243 chemical reaction Methods 0.000 claims abstract description 54
125000003545 alkoxy group Chemical group 0.000 claims abstract description 50
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 38
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 36
150000002148 esters Chemical class 0.000 claims abstract description 34
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
238000002360 preparation method Methods 0.000 claims abstract description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 25
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 17
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 11
238000006722 reduction reaction Methods 0.000 claims abstract description 10
230000009467 reduction Effects 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
150000003254 radicals Chemical class 0.000 claims abstract description 8
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 7
125000004185 ester group Chemical group 0.000 claims abstract description 6
238000011916 stereoselective reduction Methods 0.000 claims abstract description 6
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 81
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
239000012429 reaction media Substances 0.000 claims description 36
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 35
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 31
150000003839 salts Chemical group 0.000 claims description 24
239000002585 base Substances 0.000 claims description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 17
230000015572 biosynthetic process Effects 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 11
239000012279 sodium borohydride Substances 0.000 claims description 11
229910000033 sodium borohydride Inorganic materials 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
150000001450 anions Chemical class 0.000 claims description 8
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
229910052796 boron Inorganic materials 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
101150065749 Churc1 gene Proteins 0.000 claims description 6
102100038239 Protein Churchill Human genes 0.000 claims description 6
229940126545 compound 53 Drugs 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
238000012545 processing Methods 0.000 claims description 3
230000000707 stereoselective effect Effects 0.000 claims description 3
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
KMNYEDRKUIBKTM-UHFFFAOYSA-N carbonyl dichloride hydrobromide Chemical compound C(=O)(Cl)Cl.Br KMNYEDRKUIBKTM-UHFFFAOYSA-N 0.000 claims description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
229940125904 compound 1 Drugs 0.000 claims 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical group [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 claims 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 14
239000000543 intermediate Substances 0.000 abstract description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 9
239000008280 blood Substances 0.000 abstract description 5
210000004369 blood Anatomy 0.000 abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 2
150000002632 lipids Chemical class 0.000 abstract 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 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
230000000879 anti-atherosclerotic effect Effects 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
150000001721 carbon Chemical group 0.000 description 122
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 64
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 53
239000000047 product Substances 0.000 description 49
239000000243 solution Substances 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
235000002639 sodium chloride Nutrition 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
239000002904 solvent Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000376 reactant Substances 0.000 description 21
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
239000012044 organic layer Substances 0.000 description 20
239000000126 substance Substances 0.000 description 20
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
239000010410 layer Substances 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 15
230000008569 process Effects 0.000 description 15
229910000029 sodium carbonate Inorganic materials 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 12
238000009833 condensation Methods 0.000 description 12
230000005494 condensation Effects 0.000 description 12
238000004821 distillation Methods 0.000 description 12
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 12
238000001816 cooling Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
238000002844 melting Methods 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000012298 atmosphere Substances 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000012047 saturated solution Substances 0.000 description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
229920002554 vinyl polymer Polymers 0.000 description 8
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
239000002609 medium Substances 0.000 description 7
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
229910000085 borane Inorganic materials 0.000 description 6
239000008367 deionised water Substances 0.000 description 6
229910021641 deionized water Inorganic materials 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000008043 acidic salts Chemical class 0.000 description 5
239000012267 brine Substances 0.000 description 5
235000012000 cholesterol Nutrition 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
210000003739 neck Anatomy 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
231100000765 toxin Toxicity 0.000 description 5
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 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 4
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 4
239000003518 caustics Substances 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000468 ketone group Chemical group 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
150000002596 lactones Chemical class 0.000 description 4
229910052753 mercury Inorganic materials 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
230000035790 physiological processes and functions Effects 0.000 description 4
238000010791 quenching Methods 0.000 description 4
229960001922 sodium perborate Drugs 0.000 description 4
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
241001103582 Aelia Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
235000015107 ale Nutrition 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000010276 construction Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
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Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SA90100111A 1988-10-13 1990-02-24 طريقة لتحضير 7- مستبدل- حمض هبت-6- ينويك وحمض هبتانويك ومشتقات منها SA90100111B1 (ar)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US25747588A	1988-10-13	1988-10-13

Publications (1)

Publication Number	Publication Date
SA90100111B1 true SA90100111B1 (ar)	2005-04-17

Family

ID=22976450

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SA90100111A SA90100111B1 (ar)	1988-10-13	1990-02-24	طريقة لتحضير 7- مستبدل- حمض هبت-6- ينويك وحمض هبتانويك ومشتقات منها

Country Status (3)

Country	Link
DD (1)	DD296908A5 (de)
SA (1)	SA90100111B1 (de)
ZA (1)	ZA897782B (de)

1989
- 1989-10-12 DD DD89333538A patent/DD296908A5/de not_active IP Right Cessation
- 1989-10-13 ZA ZA897782A patent/ZA897782B/xx unknown
1990
- 1990-02-24 SA SA90100111A patent/SA90100111B1/ar unknown

Also Published As

Publication number	Publication date
ZA897782B (en)	1991-09-25
DD296908A5 (de)	1991-12-19

Publication	Publication Date	Title
AU636122B2 (en)	1993-04-22	Process for the preparation of 7-substituted-hept-6-enoic and-heptanoic acids and derivatives
FI90535B (fi)	1993-11-15	Menetelmä terapeuttisesti aktiivisten 7-substituoitujen 3,5-dihydroksihept-6-yynihappojen ja niiden johdannaisten valmistamiseksi ja välituotteina käyttökelpoiset yhdisteet
Biloski et al.	1982	A new. beta.-lactam synthesis
US20050032875A1 (en)	2005-02-10	Process for the preparation of indole derivatives
WO1995011898A1 (en)	1995-05-04	Condensed pyridine type mevalonolactone intermediate and process for its production
JPS60500499A (ja)	1985-04-11	メバロノラクトン同族体とその誘導体、それらの製造法、それらを含む製薬学的組成物、及びその製薬剤としての使用法
EP0397351B1 (de)	1994-07-20	Herstellung von diazabicyclischen Zwischenprodukten
KR0130467B1 (ko)	1998-04-09	아자비시클로알칸류
PH26148A (en)	1992-03-18	3-5-dihydroxy carboxylic acids
AU693588B2 (en)	1998-07-02	Novel process for the preparation of diisopinocampheylchloroborane
SA90100111B1 (ar)	2005-04-17	طريقة لتحضير 7- مستبدل- حمض هبت-6- ينويك وحمض هبتانويك ومشتقات منها
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