ZA200505103B - Process for the preparation of aryl fused polycyclic lactams - Google Patents
Process for the preparation of aryl fused polycyclic lactams Download PDFInfo
- Publication number
- ZA200505103B ZA200505103B ZA200505103A ZA200505103A ZA200505103B ZA 200505103 B ZA200505103 B ZA 200505103B ZA 200505103 A ZA200505103 A ZA 200505103A ZA 200505103 A ZA200505103 A ZA 200505103A ZA 200505103 B ZA200505103 B ZA 200505103B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- aza
- acid
- triene
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 14
- 125000003118 aryl group Chemical group 0.000 title description 8
- -1 polycyclic lactams Chemical class 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 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
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- LUGPKNSVKLHXDX-UHFFFAOYSA-N dodeca-6,8,10-trien-4-one Chemical compound CCCC(=O)CC=CC=CC=CC LUGPKNSVKLHXDX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 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 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 150000003951 lactams Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000012902 Nervous system disease Diseases 0.000 description 3
- 208000025966 Neurological disease Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000000926 neurological effect Effects 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 208000020016 psychiatric disease Diseases 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010012335 Dependence Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 150000002560 ketene acetals Chemical class 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000011975 tartaric acid Chemical class 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 230000009529 traumatic brain injury Effects 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- LOFHCHIYFDFUNK-UHFFFAOYSA-N 3-(1,3-dioxolan-2-ylidene)indene-1-carbonitrile Chemical compound C12=CC=CC=C2C(C#N)=CC1=C1OCCO1 LOFHCHIYFDFUNK-UHFFFAOYSA-N 0.000 description 1
- FIAAFZDYLWNSPA-UHFFFAOYSA-N 3-(aminomethyl)-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound C1=CC=C2C(CN)CC(C(O)=O)C2=C1 FIAAFZDYLWNSPA-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
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- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000014094 Dystonic disease Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010020651 Hyperkinesia Diseases 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- 206010061216 Infarction Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000002389 Pouchitis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 208000003554 absence epilepsy Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000007000 age related cognitive decline Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000006949 cholinergic function Effects 0.000 description 1
- 208000035127 classic pyoderma gangrenosum Diseases 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
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- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- 230000006870 function Effects 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VLYNBHYMQUZEDV-UHFFFAOYSA-N methyl 3-(aminomethyl)-2,3-dihydro-1h-indene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)CC(CN)C2=C1 VLYNBHYMQUZEDV-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44026603P | 2003-01-15 | 2003-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505103B true ZA200505103B (en) | 2006-11-29 |
Family
ID=32713537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505103A ZA200505103B (en) | 2003-01-15 | 2005-06-23 | Process for the preparation of aryl fused polycyclic lactams |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20070066827A1 (https=) |
| EP (1) | EP1587794A1 (https=) |
| JP (1) | JP2006517202A (https=) |
| KR (2) | KR20070087258A (https=) |
| CN (1) | CN100363350C (https=) |
| AR (1) | AR042855A1 (https=) |
| AU (1) | AU2004203983A1 (https=) |
| BR (1) | BRPI0406670A (https=) |
| CA (1) | CA2513293A1 (https=) |
| CL (1) | CL2004000041A1 (https=) |
| IL (1) | IL169479A0 (https=) |
| MX (1) | MXPA05007565A (https=) |
| PL (1) | PL379373A1 (https=) |
| RS (1) | RS20050513A (https=) |
| RU (1) | RU2291862C2 (https=) |
| TW (1) | TW200420286A (https=) |
| WO (1) | WO2004063164A1 (https=) |
| ZA (1) | ZA200505103B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100655848B1 (ko) | 2002-11-25 | 2006-12-11 | 화이자 프로덕츠 인크. | 1,3-치환된 인덴의 개선된 제조 방법 |
| RU2372323C1 (ru) * | 2008-04-15 | 2009-11-10 | Открытое акционерное общество Научно-производственное предприятие НИИПАВ (ОАО НПП НИИПАВ) | Способ получения высокомолекулярных аминов |
| EP2268639A2 (en) | 2008-05-22 | 2011-01-05 | Teva Pharmaceutical Industries Ltd. | Varenicline tosylate, an intermediate in the preparation process of varenicline l-tartrate |
| WO2009155403A2 (en) * | 2008-06-19 | 2009-12-23 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of varenicline and intermediates thereof |
| EP2438054A1 (en) | 2009-06-22 | 2012-04-11 | Teva Pharmaceutical Industries Ltd. | Solid states forms of varenicline salts and processes for preparation thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2168791A1 (en) * | 1993-08-05 | 1995-02-16 | Arlindo L. Castelhano | Matrix metalloprotease inhibitors |
| DE69839131T3 (de) * | 1997-12-31 | 2015-05-07 | Pfizer Products Inc. | Arylkondensierte azapolycyclische derivate |
| US6605610B1 (en) * | 1997-12-31 | 2003-08-12 | Pfizer Inc | Aryl fused azapolycyclic compounds |
| AU2002234836B2 (en) * | 2001-04-20 | 2007-08-23 | Pfizer Products Inc. | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
-
2004
- 2004-01-08 MX MXPA05007565A patent/MXPA05007565A/es unknown
- 2004-01-08 CA CA002513293A patent/CA2513293A1/en not_active Abandoned
- 2004-01-08 US US10/547,619 patent/US20070066827A1/en not_active Abandoned
- 2004-01-08 KR KR1020077018129A patent/KR20070087258A/ko not_active Withdrawn
- 2004-01-08 JP JP2006500307A patent/JP2006517202A/ja not_active Withdrawn
- 2004-01-08 RU RU2005122406/04A patent/RU2291862C2/ru not_active IP Right Cessation
- 2004-01-08 WO PCT/IB2004/000152 patent/WO2004063164A1/en not_active Ceased
- 2004-01-08 AU AU2004203983A patent/AU2004203983A1/en not_active Abandoned
- 2004-01-08 RS YUP-2005/0513A patent/RS20050513A/sr unknown
- 2004-01-08 PL PL379373A patent/PL379373A1/pl not_active Application Discontinuation
- 2004-01-08 KR KR1020057013036A patent/KR20050101177A/ko not_active Ceased
- 2004-01-08 BR BR0406670-7A patent/BRPI0406670A/pt not_active IP Right Cessation
- 2004-01-08 CN CNB2004800022895A patent/CN100363350C/zh not_active Expired - Fee Related
- 2004-01-08 EP EP04700747A patent/EP1587794A1/en not_active Withdrawn
- 2004-01-12 CL CL200400041A patent/CL2004000041A1/es unknown
- 2004-01-14 AR ARP040100091A patent/AR042855A1/es not_active Application Discontinuation
- 2004-01-14 TW TW093100889A patent/TW200420286A/zh unknown
-
2005
- 2005-06-23 ZA ZA200505103A patent/ZA200505103B/en unknown
- 2005-06-30 IL IL169479A patent/IL169479A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN100363350C (zh) | 2008-01-23 |
| US20070066827A1 (en) | 2007-03-22 |
| IL169479A0 (en) | 2007-07-04 |
| WO2004063164A1 (en) | 2004-07-29 |
| BRPI0406670A (pt) | 2005-12-20 |
| RU2291862C2 (ru) | 2007-01-20 |
| CN1738803A (zh) | 2006-02-22 |
| WO2004063164A8 (en) | 2005-05-26 |
| EP1587794A1 (en) | 2005-10-26 |
| AR042855A1 (es) | 2005-07-06 |
| JP2006517202A (ja) | 2006-07-20 |
| CL2004000041A1 (es) | 2005-04-22 |
| AU2004203983A1 (en) | 2004-07-29 |
| HK1085204A1 (zh) | 2006-08-18 |
| PL379373A1 (pl) | 2006-08-21 |
| RS20050513A (sr) | 2007-11-15 |
| CA2513293A1 (en) | 2004-07-29 |
| MXPA05007565A (es) | 2005-09-21 |
| TW200420286A (en) | 2004-10-16 |
| RU2005122406A (ru) | 2006-01-27 |
| KR20070087258A (ko) | 2007-08-27 |
| KR20050101177A (ko) | 2005-10-20 |
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