NO325150B1 - Sulfonyloksyeddiksyreesterderivater, fremgangsmate for deres fremstilling samt deres anvendelse som syntesemellomprodukter - Google Patents

Sulfonyloksyeddiksyreesterderivater, fremgangsmate for deres fremstilling samt deres anvendelse som syntesemellomprodukter Download PDF

Info

Publication number: NO325150B1
Authority: NO; Norway
Prior art keywords: stated; group; chlorophenyl; methyl; acid ester
Prior art date: 1997-10-06

Application number

NO20001736A

Other languages

English (en)

Norwegian (no)

Other versions

NO20001736L (no

NO20001736D0 (no

Inventor

Andre Bousquet

Andree Musolino

Original Assignee

Sanofi Aventis

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.)

1997-10-06

Filing date

2000-04-04

Publication date

2008-02-11

2000-04-04 Application filed by Sanofi Aventis filed Critical Sanofi Aventis

2000-04-04 Publication of NO20001736D0 publication Critical patent/NO20001736D0/no

2000-06-06 Publication of NO20001736L publication Critical patent/NO20001736L/no

2008-02-11 Publication of NO325150B1 publication Critical patent/NO325150B1/no

Links

238000000034 method Methods 0.000 title claims description 43
-1 Sulfonyloxyacetic acid ester Chemical class 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title description 6
239000000543 intermediate Substances 0.000 title description 5
239000002253 acid Substances 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 28
239000005552 B01AC04 - Clopidogrel Substances 0.000 claims description 24
GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims description 24
229960003009 clopidogrel Drugs 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 22
239000003795 chemical substances by application Substances 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
AOGSMZZEIDWJOW-CQSZACIVSA-N methyl (2r)-2-(benzenesulfonyloxy)-2-(2-chlorophenyl)acetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=CC=CC=C1 AOGSMZZEIDWJOW-CQSZACIVSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229910003002 lithium salt Inorganic materials 0.000 claims description 7
159000000002 lithium salts Chemical class 0.000 claims description 7
150000004982 aromatic amines Chemical class 0.000 claims description 6
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 6
229910001486 lithium perchlorate Inorganic materials 0.000 claims description 6
BPBBJZNRUKPSDJ-CQSZACIVSA-N methyl (2r)-2-(2-chlorophenyl)-2-(4-nitrophenyl)sulfonyloxyacetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 BPBBJZNRUKPSDJ-CQSZACIVSA-N 0.000 claims description 6
239000002798 polar solvent Substances 0.000 claims description 6
WRNCAJVYSZFDPH-CQSZACIVSA-N methyl (2r)-2-(2-chlorophenyl)-2-(2,5-dichlorophenyl)sulfonyloxyacetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=CC(Cl)=CC=C1Cl WRNCAJVYSZFDPH-CQSZACIVSA-N 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
150000003461 sulfonyl halides Chemical class 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
230000022244 formylation Effects 0.000 claims description 3
238000006170 formylation reaction Methods 0.000 claims description 3
229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 3
YPCYCGGEMDSLDC-MRXNPFEDSA-N methyl (2r)-2-(2-chlorophenyl)-2-(2,4,6-trimethylphenyl)sulfonyloxyacetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=C(C)C=C(C)C=C1C YPCYCGGEMDSLDC-MRXNPFEDSA-N 0.000 claims description 3
CIBFZAMKUSNKFH-CQSZACIVSA-N methyl (2r)-2-(2-chlorophenyl)-2-(4-chlorophenyl)sulfonyloxyacetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=CC=C(Cl)C=C1 CIBFZAMKUSNKFH-CQSZACIVSA-N 0.000 claims description 3
PINYXVRQIQKIJN-JOCHJYFZSA-N methyl (2r)-2-(2-chlorophenyl)-2-[2,4,6-tri(propan-2-yl)phenyl]sulfonyloxyacetate Chemical group O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C PINYXVRQIQKIJN-JOCHJYFZSA-N 0.000 claims description 3
239000012454 non-polar solvent Substances 0.000 claims description 3
238000006116 polymerization reaction Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical class NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 claims description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
150000001412 amines Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000005587 carbonate group Chemical group 0.000 claims 1
150000008282 halocarbons Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
125000003118 aryl group Chemical group 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
230000003287 optical effect Effects 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMPGBVQQIQSQED-MRVPVSSYSA-N methyl (2r)-2-(2-chlorophenyl)-2-hydroxyacetate Chemical compound COC(=O)[C@H](O)C1=CC=CC=C1Cl ZMPGBVQQIQSQED-MRVPVSSYSA-N 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
RWOLDZZTBNYTMS-SSDOTTSWSA-N (2r)-2-(2-chlorophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1Cl RWOLDZZTBNYTMS-SSDOTTSWSA-N 0.000 description 4
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
BUGNHCGQRDZRSQ-UHFFFAOYSA-N methyl 2-chloro-2-(2-chlorophenyl)acetate Chemical compound COC(=O)C(Cl)C1=CC=CC=C1Cl BUGNHCGQRDZRSQ-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 3
238000010908 decantation Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000010534 nucleophilic substitution reaction Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
CJPVPOYTTALCNX-UHFFFAOYSA-N (2-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1Cl CJPVPOYTTALCNX-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
RWOLDZZTBNYTMS-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1Cl RWOLDZZTBNYTMS-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
229940011051 isopropyl acetate Drugs 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
230000006340 racemization Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical class O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
FDEODCTUSIWGLK-RSAXXLAASA-N clopidogrel sulfate Chemical compound [H+].OS([O-])(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl FDEODCTUSIWGLK-RSAXXLAASA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
JYAHLZXGPKGNJS-SECBINFHSA-N methyl (2R)-2-(2-chlorophenyl)-2-methylsulfonyloxyacetate Chemical compound COC(=O)[C@H](OS(C)(=O)=O)C1=CC=CC=C1Cl JYAHLZXGPKGNJS-SECBINFHSA-N 0.000 description 1
PDIIKCXDULBMTD-OAHLLOKOSA-N methyl (2r)-2-(2-chlorophenyl)-2-(4-methylphenyl)sulfonyloxyacetate Chemical compound O([C@@H](C(=O)OC)C=1C(=CC=CC=1)Cl)S(=O)(=O)C1=CC=C(C)C=C1 PDIIKCXDULBMTD-OAHLLOKOSA-N 0.000 description 1
BUGNHCGQRDZRSQ-QMMMGPOBSA-N methyl (2s)-2-chloro-2-(2-chlorophenyl)acetate Chemical compound COC(=O)[C@@H](Cl)C1=CC=CC=C1Cl BUGNHCGQRDZRSQ-QMMMGPOBSA-N 0.000 description 1
XEUQMYXHUMKCJY-UHFFFAOYSA-N methyl 2-methylsulfonyloxypropanoate Chemical compound COC(=O)C(C)OS(C)(=O)=O XEUQMYXHUMKCJY-UHFFFAOYSA-N 0.000 description 1
125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Hematology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)
Cephalosporin Compounds (AREA)

NO20001736A 1997-10-06 2000-04-04 Sulfonyloksyeddiksyreesterderivater, fremgangsmate for deres fremstilling samt deres anvendelse som syntesemellomprodukter NO325150B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9712441A FR2769313B1 (fr)	1997-10-06	1997-10-06	Derives d'esters hydroxyacetiques, leur procede de preparation et leur utilisation comme intermediaires de synthese
PCT/FR1998/002082 WO1999018110A1 (fr)	1997-10-06	1998-09-29	Derives d'esters hydroxyacetiques, leur procede de preparation et leur utilisation comme intermediaires de synthese

Publications (3)

Publication Number	Publication Date
NO20001736D0 NO20001736D0 (no)	2000-04-04
NO20001736L NO20001736L (no)	2000-06-06
NO325150B1 true NO325150B1 (no)	2008-02-11

Family

ID=9511879

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20001736A NO325150B1 (no)	1997-10-06	2000-04-04	Sulfonyloksyeddiksyreesterderivater, fremgangsmate for deres fremstilling samt deres anvendelse som syntesemellomprodukter

Country Status (15)

Country	Link
US (3)	US6573381B1 (de)
EP (1)	EP1021449B1 (de)
JP (3)	JP3827946B2 (de)
AT (1)	ATE211476T1 (de)
AU (1)	AU9354498A (de)
BR (1)	BR9813022B1 (de)
CA (1)	CA2306409C (de)
DE (1)	DE69803397T2 (de)
DK (1)	DK1021449T3 (de)
ES (1)	ES2171040T3 (de)
FR (1)	FR2769313B1 (de)
HU (1)	HU226771B1 (de)
NO (1)	NO325150B1 (de)
PT (1)	PT1021449E (de)
WO (1)	WO1999018110A1 (de)

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CN101253271A (zh) *	2005-09-02	2008-08-27	第一精密化学株式会社	光学活性α-羟基羧酸的制造方法
KR101235117B1 (ko)	2005-12-26	2013-02-20	에스케이케미칼주식회사	광학분리에 의한 (ｓ)-(＋)-클로피도그렐의 제조방법
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WO2008004249A2 (en) *	2006-07-04	2008-01-10	Msn Laboratories Limited	An improved process for the preparation of clopidogrel and its pharmaceutically acceptable salts
TW200823215A (en) *	2006-08-04	2008-06-01	Merz Pharma Gmbh & Amp Co Kgaa	Pyrazolopyrimidines, a process for their preparation and the use as a medicine
KR100834967B1 (ko) *	2006-08-11	2008-06-03	에스케이케미칼주식회사	여액의 라세미화 반응에 의한 ｓ-(＋)-클로피도그렐의고수율 제조방법
EP1980563A1 (de)	2007-04-09	2008-10-15	BATTULA, Srinivasa Reddy	Verfahren zur Herstellung von Methyl (+)-(S)-Alpha-(O-Chlorophenyl)-6,7-Dihydrothieno-[3,2-C]pyridine-5(4H) Acetat
KR20090086903A (ko) *	2007-04-18	2009-08-14	테바 파마슈티컬 인더스트리즈 리미티드	개선된 클로피도그렐의 제조 방법
CN101686681B (zh)	2007-04-27	2015-04-01	锡德克斯药物公司	包含氯吡格雷和磺基烷基醚环糊精的制剂和其使用方法
EP2107061A1 (de)	2008-04-02	2009-10-07	Krka Tovarna Zdravil, D.D., Novo Mesto	Herstellungsverfahren für optisch angereichertes Clopidogrel
KR100990949B1 (ko)	2008-06-09	2010-10-29	엔자이텍 주식회사	클로피도그렐 및 그의 유도체의 제조방법
PL3100728T3 (pl)	2009-05-13	2020-05-18	Cydex Pharmaceuticals, Inc.	Kompozycje farmaceutyczne zawierające prasugrel i pochodne cyklodekstryny oraz sposoby ich wytwarzania i zastosowania
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1997
- 1997-10-06 FR FR9712441A patent/FR2769313B1/fr not_active Expired - Lifetime
1998
- 1998-09-29 PT PT98946523T patent/PT1021449E/pt unknown
- 1998-09-29 CA CA2306409A patent/CA2306409C/fr not_active Expired - Lifetime
- 1998-09-29 US US09/509,879 patent/US6573381B1/en not_active Expired - Lifetime
- 1998-09-29 ES ES98946523T patent/ES2171040T3/es not_active Expired - Lifetime
- 1998-09-29 BR BRPI9813022-6A patent/BR9813022B1/pt not_active IP Right Cessation
- 1998-09-29 WO PCT/FR1998/002082 patent/WO1999018110A1/fr not_active Ceased
- 1998-09-29 EP EP98946523A patent/EP1021449B1/de not_active Expired - Lifetime
- 1998-09-29 DE DE69803397T patent/DE69803397T2/de not_active Expired - Lifetime
- 1998-09-29 DK DK98946523T patent/DK1021449T3/da active
- 1998-09-29 AU AU93544/98A patent/AU9354498A/en not_active Abandoned
- 1998-09-29 HU HU0004250A patent/HU226771B1/hu unknown
- 1998-09-29 JP JP2000514920A patent/JP3827946B2/ja not_active Expired - Lifetime
- 1998-09-29 AT AT98946523T patent/ATE211476T1/de active
2000
- 2000-04-04 NO NO20001736A patent/NO325150B1/no not_active IP Right Cessation
2003
- 2003-04-29 US US10/425,437 patent/US6894186B2/en not_active Expired - Lifetime
2004
- 2004-07-14 US US10/890,749 patent/US7153969B2/en not_active Expired - Lifetime
2005
- 2005-12-20 JP JP2005366868A patent/JP4264437B2/ja not_active Expired - Lifetime
2009
- 2009-01-08 JP JP2009002505A patent/JP4903819B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US7153969B2 (en)	2006-12-26
DK1021449T3 (da)	2002-04-22
HUP0004250A2 (hu)	2001-10-28
FR2769313A1 (fr)	1999-04-09
BR9813022A (pt)	2000-08-15
DE69803397T2 (de)	2002-08-29
ES2171040T3 (es)	2002-08-16
HUP0004250A3 (en)	2001-12-28
PT1021449E (pt)	2002-06-28
JP4264437B2 (ja)	2009-05-20
WO1999018110A1 (fr)	1999-04-15
JP4903819B2 (ja)	2012-03-28
EP1021449A1 (de)	2000-07-26
AU9354498A (en)	1999-04-27
EP1021449B1 (de)	2002-01-02
US6894186B2 (en)	2005-05-17
JP2001519353A (ja)	2001-10-23
NO20001736L (no)	2000-06-06
ATE211476T1 (de)	2002-01-15
CA2306409C (fr)	2010-06-29
JP2009137989A (ja)	2009-06-25
DE69803397D1 (de)	2002-02-28
JP2006124398A (ja)	2006-05-18
HU226771B1 (en)	2009-09-28
US20030208077A1 (en)	2003-11-06
CA2306409A1 (fr)	1999-04-15
FR2769313B1 (fr)	2000-04-21
BR9813022B1 (pt)	2010-07-13
US20040260110A1 (en)	2004-12-23
US6573381B1 (en)	2003-06-03
NO20001736D0 (no)	2000-04-04
JP3827946B2 (ja)	2006-09-27

Legal Events

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2018-10-08	MK1K	Patent expired

Publication	Publication Date	Title
US6573381B1 (en)	2003-06-03	Hydroxyacetic ester derivatives, preparation method and use as synthesis intermediates
PL177891B1 (pl)	2000-01-31	Sposób wytwarzania florfenikolu, tiamfenikolu i chloramfenikolu
KR101777474B1 (ko)	2017-09-11	1,3-프로프-1-엔 설톤의 제조방법
RU2378261C2 (ru)	2010-01-10	Способ получения солевого соединения (4,5-дигидроизоксазол-3-ил)тиокарбоксамидина
KR101100064B1 (ko)	2011-12-29	나프록센의 니트로옥시유도체 제조방법
EP0884313B1 (de)	2000-11-08	Verfahren zur herstellung von glycidylsulfonaten
KR101135088B1 (ko)	2012-04-16	1,3-프로펜설톤의 제조방법
NO167922B (no)	1991-09-16	Imidazolderivater
US6642395B1 (en)	2003-11-04	Acetalsulfonate derivative, process for producing the same, and process for producing styrene oxide derivative
CN121175316A (zh)	2025-12-19	环状酰基亚砜亚胺的合成
US4864046A (en)	1989-09-05	Process for optically active 3-thiolanyl sulfonate esters
KR20240027729A (ko)	2024-03-04	이속사졸린카르복실산 유도체의 제조 방법
MXPA00003334A (en)	2001-05-07	Hydroxyacetic ester derivatives, preparation method and use as synthesis intermediates
JP2004224714A (ja)	2004-08-12	イソオキサゾリジン−３−チオン誘導体の製造法
AU609348B2 (en)	1991-04-26	Process for the preparation of optically active 3-thiolanyl sulfonate esters
US4921972A (en)	1990-05-01	Process for optically active 3-thiolanyl sulfonate esters
CS362989A3 (en)	1992-12-16	Process for preparing lactol derivatives
CA1274846A (en)	1990-10-02	PROCESS FOR ENANTIOSELECTIVE PRODUCTION OF .alpha.-VINYL- .alpha.-AMINO ACIDS
BG107145A (bg)	2003-05-30	Метод за селективно n-формилиране на n-хидроксиламини
US4701528A (en)	1987-10-20	Intermediates useful in the preparation of 3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-2-carboxylates and process for preparing same
KR100914849B1 (ko)	2009-09-02	2-설포닐옥시-1-(4-하이드록시페닐)에탄올 유도체의 제조방법
JP2002284764A (ja)	2002-10-03	２−（アルコキシベンジルオキシ）−３−ニトロピリジン及びこれを用いるアルコキシベンジルエーテル化合物の製造法
MXPA97002446A (en)	1998-07-03	Procedure for the preparation of acids cicloalcano-indol- and pirimido- [1,2a] indol-carboxilicosanantiomeros puros and their active derivatives
KR20010071616A (ko)	2001-07-28	페닐알칸산아미드화합물의 제조방법 및 그를 위한 중간체