OA10138A - Process of synthesizing useful intermediates of substituted imidazole compounds - Google Patents

Process of synthesizing useful intermediates of substituted imidazole compounds Download PDF

Info

Publication number: OA10138A
Authority: OA; OAPI
Prior art keywords: cgalkyl; compound; substituted; phenyl; preparing
Prior art date: 1992-09-23

Application number

OA60627A

Other languages

English (en)

Inventor

Mohamed Kheir Mokhallalati

Lendon Norwood Pridgen

Susan Shilcrat

Joseph Weinstock

Original Assignee

Smithkline Beecham Corp

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.)

1992-09-23

Filing date

1995-03-20

Publication date

1996-12-18

1995-03-20 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1996-12-18 Publication of OA10138A publication Critical patent/OA10138A/en

Links

238000000034 method Methods 0.000 title claims description 23
239000000543 intermediate Substances 0.000 title description 7
150000002460 imidazoles Chemical class 0.000 title description 3
230000002194 synthesizing effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 25
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
-1 A-CO2R6 Chemical group 0.000 claims description 9
125000001624 naphthyl group Chemical group 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
239000004305 biphenyl Substances 0.000 claims description 8
235000010290 biphenyl Nutrition 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
229910006069 SO3H Inorganic materials 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
239000005711 Benzoic acid Substances 0.000 claims 1
235000010233 benzoic acid Nutrition 0.000 claims 1
ISPFOTKDTUJUDE-UHFFFAOYSA-N ethyl 4-[(2-butyl-5-formylimidazol-1-yl)methyl]benzoate Chemical compound CCCCC1=NC=C(C=O)N1CC1=CC=C(C(=O)OCC)C=C1 ISPFOTKDTUJUDE-UHFFFAOYSA-N 0.000 claims 1
NBKPQAOGTANTFK-UHFFFAOYSA-N ethyl 4-[(2-butyl-5-formylimidazol-1-yl)methyl]naphthalene-1-carboxylate Chemical compound CCCCC1=NC=C(C=O)N1CC1=CC=C(C(=O)OCC)C2=CC=CC=C12 NBKPQAOGTANTFK-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
UCDIXJKWUCLMJK-UHFFFAOYSA-N 2-bromo-3-propan-2-yloxyprop-2-enal Chemical compound CC(C)OC=C(Br)C=O UCDIXJKWUCLMJK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
RZUOYFGIQVKGKC-UHFFFAOYSA-N 4-[(1-aminopentylideneamino)methyl]benzoic acid Chemical compound CCCCC(=N)NCC1=CC=C(C(O)=O)C=C1 RZUOYFGIQVKGKC-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
MSQGUKKNARWCBF-UHFFFAOYSA-N ethyl 4-[(1-aminopentylideneamino)methyl]benzoate Chemical compound CCCCC(=N)NCC1=CC=C(C(=O)OCC)C=C1 MSQGUKKNARWCBF-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
229940093956 potassium carbonate Drugs 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CUKWUWBLQQDQAC-VEQWQPCFSA-N (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s,3s)-1-[[(2s)-1-[(2s)-2-[[(1s)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-ox Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 CUKWUWBLQQDQAC-VEQWQPCFSA-N 0.000 description 1
XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 1
UAIVSGKSLHIONB-UHFFFAOYSA-N 1-methoxypentylideneazanium;chloride Chemical compound Cl.CCCCC(=N)OC UAIVSGKSLHIONB-UHFFFAOYSA-N 0.000 description 1
ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical class O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 1
SURMYNZXHKLDFO-UHFFFAOYSA-N 2-bromopropanedial Chemical compound O=CC(Br)C=O SURMYNZXHKLDFO-UHFFFAOYSA-N 0.000 description 1
QLMGJDCOKQGJKF-UHFFFAOYSA-N 4-[(2-butyl-5-formylimidazol-1-yl)methyl]benzoic acid Chemical compound CCCCC1=NC=C(C=O)N1CC1=CC=C(C(O)=O)C=C1 QLMGJDCOKQGJKF-UHFFFAOYSA-N 0.000 description 1
QWVFYZAYKGIEFP-UHFFFAOYSA-N 4-[(2-butyl-5-formylimidazol-1-yl)methyl]naphthalene-1-carboxylic acid Chemical compound CCCCC1=NC=C(C=O)N1CC1=CC=C(C(O)=O)C2=CC=CC=C12 QWVFYZAYKGIEFP-UHFFFAOYSA-N 0.000 description 1
102000005862 Angiotensin II Human genes 0.000 description 1
101800000733 Angiotensin-2 Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101100493710 Caenorhabditis elegans bath-40 gene Proteins 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
101100391171 Schizosaccharomyces pombe (strain 972 / ATCC 24843) for3 gene Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
229950006323 angiotensin ii Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229940120503 dihydroxyacetone Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
VCKULWDHBHUCPY-UHFFFAOYSA-N ethyl 4-[(1-aminopentylideneamino)methyl]naphthalene-1-carboxylate Chemical compound C1=CC=C2C(CNC(=N)CCCC)=CC=C(C(=O)OCC)C2=C1 VCKULWDHBHUCPY-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
DIFSGQKADHEBAI-UHFFFAOYSA-N methyl pentanimidate Chemical compound CCCCC(=N)OC DIFSGQKADHEBAI-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

OA60627A 1992-09-23 1995-03-20 Process of synthesizing useful intermediates of substituted imidazole compounds OA10138A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB929220068A GB9220068D0 (en)	1992-09-23	1992-09-23	Process

Publications (1)

Publication Number	Publication Date
OA10138A true OA10138A (en)	1996-12-18

Family

ID=10722348

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60627A OA10138A (en)	1992-09-23	1995-03-20	Process of synthesizing useful intermediates of substituted imidazole compounds

Country Status (36)

Country	Link
EP (1)	EP0662961B1 (fr)
JP (1)	JPH08501307A (fr)
KR (1)	KR100297505B1 (fr)
CN (1)	CN1035613C (fr)
AP (1)	AP418A (fr)
AT (1)	ATE186531T1 (fr)
AU (1)	AU676848B2 (fr)
BG (1)	BG62328B1 (fr)
BR (1)	BR9307201A (fr)
CA (1)	CA2145181C (fr)
CZ (1)	CZ282281B6 (fr)
DE (1)	DE69327007T2 (fr)
DK (1)	DK0662961T3 (fr)
ES (1)	ES2137999T3 (fr)
FI (1)	FI113170B (fr)
GB (1)	GB9220068D0 (fr)
GR (1)	GR3032015T3 (fr)
HU (1)	HU224071B1 (fr)
IL (1)	IL107047A (fr)
MA (1)	MA22980A1 (fr)
MX (1)	MX9305844A (fr)
MY (1)	MY110202A (fr)
NO (1)	NO304688B1 (fr)
NZ (1)	NZ256223A (fr)
OA (1)	OA10138A (fr)
PH (1)	PH31154A (fr)
PL (1)	PL173450B1 (fr)
RO (1)	RO113146B1 (fr)
RU (1)	RU2128174C1 (fr)
SA (1)	SA93140423B1 (fr)
SI (1)	SI9300494A (fr)
SK (1)	SK281227B6 (fr)
TW (1)	TW409124B (fr)
UA (1)	UA41903C2 (fr)
WO (1)	WO1994006776A1 (fr)
ZA (1)	ZA936962B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9220068D0 (en) *	1992-09-23	1992-11-04	Smithkline Beecham Corp	Process
US5565577A (en) *	1992-09-23	1996-10-15	Smithkline Beecham Corporation	Process for preparing 1-alkyaryl-2-alkyl-5-formylimidazole
US7858807B2 (en)	2005-08-23	2010-12-28	Ube Industries, Ltd.	Method for producing 1-substituted-5-acylimidazole compound
KR101472686B1 (ko) *	2013-07-09	2014-12-16	씨제이헬스케어 주식회사	벤즈이미다졸 유도체의 제조방법
CN103435617B (zh) *	2013-08-22	2016-04-27	南京华安药业有限公司	一种6,7-二氢-5H-吡咯并[1,2-a]咪唑-2-甲醛的合成方法
CN115894192A (zh) *	2022-12-05	2023-04-04	苏州诚和医药化学有限公司	一种2-溴丙二醛的合成方法、应用及2-溴丙二醛

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU250902A1 (ru) *	1968-06-24	1989-07-30	Новокузнецкий научно-исследовательский химико-фармацевтический институт	Способ получени 4(5)-карбпропоксиимидазолил-5(4)-амида @ -бис-(2-хлорэтил)-аминофенилуксусной кислоты
JPS5671073A (en) *	1979-11-12	1981-06-13	Takeda Chem Ind Ltd	Imidazole derivative
US4482723A (en) *	1983-04-11	1984-11-13	Pfizer Inc.	Process for preparation of 4-acetyl-2-substituted-imidazoles
US4602093A (en) *	1984-02-08	1986-07-22	Merck & Co., Inc.	Novel substituted imidazoles, their preparation and use
DE3811621A1 (de) *	1988-04-07	1989-10-26	Merck Patent Gmbh	Verfahren zur herstellung von 1h-imidazol-5-carbon-saeureestern oder -nitrilen und von pyrrol-3,4-carbonsaeureestern oder -nitrilen sowie verwendung der hergestellten verbindungen zur synthese von pilocarpin
US5234917A (en) *	1989-12-29	1993-08-10	Finkelstein Joseph A	Substituted 5-(alkyl)carboxamide imidazoles
GB9220068D0 (en) *	1992-09-23	1992-11-04	Smithkline Beecham Corp	Process

1992
- 1992-09-23 GB GB929220068A patent/GB9220068D0/en active Pending
1993
- 1993-09-07 DK DK93921386T patent/DK0662961T3/da active
- 1993-09-07 CZ CZ95708A patent/CZ282281B6/cs not_active IP Right Cessation
- 1993-09-07 KR KR1019950701094A patent/KR100297505B1/ko not_active Expired - Fee Related
- 1993-09-07 AU AU48496/93A patent/AU676848B2/en not_active Ceased
- 1993-09-07 SK SK373-95A patent/SK281227B6/sk not_active IP Right Cessation
- 1993-09-07 CA CA002145181A patent/CA2145181C/fr not_active Expired - Fee Related
- 1993-09-07 AT AT93921386T patent/ATE186531T1/de active
- 1993-09-07 RU RU95108600A patent/RU2128174C1/ru not_active IP Right Cessation
- 1993-09-07 ES ES93921386T patent/ES2137999T3/es not_active Expired - Lifetime
- 1993-09-07 NZ NZ256223A patent/NZ256223A/en not_active IP Right Cessation
- 1993-09-07 BR BR9307201A patent/BR9307201A/pt active Search and Examination
- 1993-09-07 EP EP93921386A patent/EP0662961B1/fr not_active Expired - Lifetime
- 1993-09-07 UA UA95048355A patent/UA41903C2/uk unknown
- 1993-09-07 HU HU9500837A patent/HU224071B1/hu not_active IP Right Cessation
- 1993-09-07 RO RO95-00556A patent/RO113146B1/ro unknown
- 1993-09-07 WO PCT/US1993/008390 patent/WO1994006776A1/fr not_active Ceased
- 1993-09-07 JP JP6508126A patent/JPH08501307A/ja not_active Ceased
- 1993-09-07 DE DE69327007T patent/DE69327007T2/de not_active Expired - Lifetime
- 1993-09-17 AP APAP/P/1993/000565A patent/AP418A/en active
- 1993-09-17 PH PH46894A patent/PH31154A/en unknown
- 1993-09-20 MY MYPI93001904A patent/MY110202A/en unknown
- 1993-09-20 IL IL107047A patent/IL107047A/en not_active IP Right Cessation
- 1993-09-21 MA MA23293A patent/MA22980A1/fr unknown
- 1993-09-21 ZA ZA936962A patent/ZA936962B/xx unknown
- 1993-09-22 MX MX9305844A patent/MX9305844A/es unknown
- 1993-09-23 SI SI9300494A patent/SI9300494A/sl not_active IP Right Cessation
- 1993-09-23 CN CN93119602A patent/CN1035613C/zh not_active Expired - Fee Related
- 1993-10-13 TW TW082108450A patent/TW409124B/zh not_active IP Right Cessation
- 1993-12-18 SA SA93140423A patent/SA93140423B1/ar unknown
1995
- 1995-03-20 OA OA60627A patent/OA10138A/en unknown
- 1995-03-21 PL PL93308173A patent/PL173450B1/pl unknown
- 1995-03-22 FI FI951350A patent/FI113170B/fi not_active IP Right Cessation
- 1995-03-22 NO NO951082A patent/NO304688B1/no not_active IP Right Cessation
- 1995-03-23 BG BG99520A patent/BG62328B1/bg unknown
1999
- 1999-11-30 GR GR990403109T patent/GR3032015T3/el unknown

Also Published As

Publication number	Publication date
EP0662961A4 (fr)	1996-07-31
GB9220068D0 (en)	1992-11-04
BG99520A (bg)	1996-01-31
KR100297505B1 (ko)	2001-10-24
ES2137999T3 (es)	2000-01-01
CZ282281B6 (cs)	1997-06-11
RU95108600A (ru)	1997-01-10
SK37395A3 (en)	1995-08-09
KR950703536A (ko)	1995-09-20
SA93140423B1 (ar)	2005-10-01
HK1012357A1 (en)	1999-07-30
PL308173A1 (en)	1995-07-24
CN1092411A (zh)	1994-09-21
FI113170B (fi)	2004-03-15
AP9300565A0 (en)	1993-10-31
AU4849693A (en)	1994-04-12
AU676848B2 (en)	1997-03-27
NO951094D0 (no)	1995-03-22
NO304688B1 (no)	1999-02-01
SK281227B6 (sk)	2001-01-18
MX9305844A (es)	1994-03-31
NO951094L (no)	1995-03-22
IL107047A0 (en)	1993-12-28
HU9500837D0 (en)	1995-05-29
FI951350A0 (fi)	1995-03-22
TW409124B (en)	2000-10-21
BR9307201A (pt)	1999-03-30
ZA936962B (en)	1994-08-01
PH31154A (en)	1998-03-20
IL107047A (en)	1998-04-05
AP418A (en)	1995-10-24
CA2145181A1 (fr)	1994-03-31
HUT71335A (en)	1995-11-28
BG62328B1 (bg)	1999-08-31
MY110202A (en)	1998-02-28
JPH08501307A (ja)	1996-02-13
FI951350L (fi)	1995-03-22
SI9300494A (en)	1994-03-31
NZ256223A (en)	1996-06-25
CA2145181C (fr)	2004-11-16
RO113146B1 (ro)	1998-04-30
DK0662961T3 (da)	2000-04-17
GR3032015T3 (en)	2000-03-31
MA22980A1 (fr)	1994-04-01
WO1994006776A1 (fr)	1994-03-31
DE69327007D1 (de)	1999-12-16
ATE186531T1 (de)	1999-11-15
UA41903C2 (uk)	2001-10-15
RU2128174C1 (ru)	1999-03-27
HU224071B1 (hu)	2005-05-30
EP0662961B1 (fr)	1999-11-10
DE69327007T2 (de)	2000-04-20
EP0662961A1 (fr)	1995-07-19
CN1035613C (zh)	1997-08-13
CZ70895A3 (en)	1995-11-15
PL173450B1 (pl)	1998-03-31

Publication	Publication Date	Title
JP3827946B2 (ja)	2006-09-27	ヒドロキシ酢酸エステル誘導体、その製法及び合成中間体としての用途
JP2023532362A (ja)	2023-07-27	フェニルイソオキサゾリン系化合物の製造方法
EP3668857A1 (fr)	2020-06-24	Procédés de préparation de niraparib et intermédiaires de celui-ci
SK163696A3 (en)	1997-10-08	3-amino-2-mercaptobenzoic acid derivatives, preparation method thereof, intermediate products at this method and their use
CA2201435C (fr)	2006-12-12	Procede pour la preparation d'acides cycloalcano-indole - carboxyliques,azaindole-carboxyliques et pyrimido [1,2a]dole- carboxyliques enantiome riquement purs et de leurs derives actifs
TWI399363B (zh)	2013-06-21	方法
OA10138A (en)	1996-12-18	Process of synthesizing useful intermediates of substituted imidazole compounds
JP4828863B2 (ja)	2011-11-30	（ｚ）−１−フェニル−１−（ｎ，ｎ−ジエチルアミノカルボニル）−２−フタルイミドメチルシクロプロパンの製造方法
US5565577A (en)	1996-10-15	Process for preparing 1-alkyaryl-2-alkyl-5-formylimidazole
AU737994B2 (en)	2001-09-06	Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides
CN115197261B (zh)	2024-05-03	噁二氮杂硼衍生物的合成方法
KR100481570B1 (ko)	2005-04-08	2-이미다졸린-5-온 제조용 중간체
JP4161290B2 (ja)	2008-10-08	ピリミジニルアルコール誘導体の製造方法及びその合成中間体
CN109970668B (zh)	2021-12-07	一种制备3-硫代-1,2,4-三氮唑类化合物的方法
HK1012357B (en)	2000-05-05	Process of synthesizing useful intermediates of substituted imidazole compounds
KR101170024B1 (ko)	2012-08-28	아조세미드 제조방법
WO2022149081A1 (fr)	2022-07-14	Procédé amélioré pour la préparation d'un composé utile dans la préparation d'un composé anti-androgénique
JPS6131098B2 (fr)	1986-07-17
MXPA97002446A (en)	1998-07-03	Procedure for the preparation of acids cicloalcano-indol- and pirimido- [1,2a] indol-carboxilicosanantiomeros puros and their active derivatives
CN114380783A (zh)	2022-04-22	一种奥洛他定氘标记代谢物的制备方法
JPH10195048A (ja)	1998-07-28	３−（ニトロベンゾイル）インドール誘導体の製造法
JPH1135563A (ja)	1999-02-09	アゾール−１−イルアルキルニトリル類の製造法
JPS63165354A (ja)	1988-07-08	不斉シアンヒドリンの製造法
HU202193B (en)	1991-02-28	Process for producing substituted amides
UA51621C2 (uk)	2002-12-16	Похідні 3-аміно-2-меркаптобензойної кислоти та способи їх одержання