UA61991C2 - Azapolycyclic compounds condensed with aryl, intermediate compounds (variants), pharmaceutical composition (variants), a method for lowering the nicotine dependence and help to stop or lower the tobacco use by a mammal, and a method for treatment - Google Patents

Azapolycyclic compounds condensed with aryl, intermediate compounds (variants), pharmaceutical composition (variants), a method for lowering the nicotine dependence and help to stop or lower the tobacco use by a mammal, and a method for treatment Download PDF

Info

Publication number: UA61991C2
Authority: UA; Ukraine
Prior art keywords: azatricyclo; alkyl; triene; formula; tetraene
Prior art date: 1998-04-29

Application number

UA2000095418A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Pfizer Prod Inc

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.)

1998-04-29

Filing date

1999-08-04

Publication date

2003-12-15

1999-08-04 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-12-15 Publication of UA61991C2 publication Critical patent/UA61991C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 275
238000000034 method Methods 0.000 title claims abstract description 77
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
125000003118 aryl group Chemical class 0.000 title claims description 16
241000124008 Mammalia Species 0.000 title claims description 11
241000208125 Nicotiana Species 0.000 title claims description 9
235000002637 Nicotiana tabacum Nutrition 0.000 title claims description 9
206010057852 Nicotine dependence Diseases 0.000 title claims description 9
208000025569 Tobacco Use disease Diseases 0.000 title claims description 9
150000003839 salts Chemical class 0.000 claims abstract description 21
-1 nitro- Chemical class 0.000 claims description 82
125000000217 alkyl group Chemical group 0.000 claims description 72
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
239000001257 hydrogen Substances 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 47
229920006395 saturated elastomer Polymers 0.000 claims description 38
229910052757 nitrogen Inorganic materials 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
208000010877 cognitive disease Diseases 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
230000009467 reduction Effects 0.000 claims description 14
125000001153 fluoro group Chemical group F* 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 12
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 12
125000002619 bicyclic group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000011737 fluorine Substances 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
206010012335 Dependence Diseases 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
208000002193 Pain Diseases 0.000 claims description 10
208000018737 Parkinson disease Diseases 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
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 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
239000011593 sulfur Chemical group 0.000 claims description 10
229910052717 sulfur Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
208000030886 Traumatic Brain injury Diseases 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
229960002715 nicotine Drugs 0.000 claims description 8
230000009529 traumatic brain injury Effects 0.000 claims description 8
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 7
208000028698 Cognitive impairment Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
125000005605 benzo group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
206010015037 epilepsy Diseases 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
230000006999 cognitive decline Effects 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 5
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208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
206010003805 Autism Diseases 0.000 claims description 5
208000020706 Autistic disease Diseases 0.000 claims description 5
208000020925 Bipolar disease Diseases 0.000 claims description 5
208000032841 Bulimia Diseases 0.000 claims description 5
206010006550 Bulimia nervosa Diseases 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
208000000094 Chronic Pain Diseases 0.000 claims description 5
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 5
206010009900 Colitis ulcerative Diseases 0.000 claims description 5
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206010039966 Senile dementia Diseases 0.000 claims description 5
208000000323 Tourette Syndrome Diseases 0.000 claims description 5
208000016620 Tourette disease Diseases 0.000 claims description 5
208000025865 Ulcer Diseases 0.000 claims description 5
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206010047139 Vasoconstriction Diseases 0.000 claims description 5
208000005298 acute pain Diseases 0.000 claims description 5
208000022531 anorexia Diseases 0.000 claims description 5
230000036506 anxiety Effects 0.000 claims description 5
206010003119 arrhythmia Diseases 0.000 claims description 5
229940125717 barbiturate Drugs 0.000 claims description 5
229940049706 benzodiazepine Drugs 0.000 claims description 5
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 5
229960003920 cocaine Drugs 0.000 claims description 5
206010061428 decreased appetite Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
206010013663 drug dependence Diseases 0.000 claims description 5
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208000010118 dystonia Diseases 0.000 claims description 5
231100000869 headache Toxicity 0.000 claims description 5
208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 5
235000020824 obesity Nutrition 0.000 claims description 5
229940005483 opioid analgesics Drugs 0.000 claims description 5
208000019906 panic disease Diseases 0.000 claims description 5
208000028591 pheochromocytoma Diseases 0.000 claims description 5
201000000980 schizophrenia Diseases 0.000 claims description 5
208000019116 sleep disease Diseases 0.000 claims description 5
230000001148 spastic effect Effects 0.000 claims description 5
208000011117 substance-related disease Diseases 0.000 claims description 5
235000019505 tobacco product Nutrition 0.000 claims description 5
231100000397 ulcer Toxicity 0.000 claims description 5
230000025033 vasoconstriction Effects 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
208000007542 Paresis Diseases 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
208000006011 Stroke Diseases 0.000 claims description 4
230000003187 abdominal effect Effects 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
208000012661 Dyskinesia Diseases 0.000 claims description 3
208000003554 absence epilepsy Diseases 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
210000004211 gastric acid Anatomy 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
150000004702 methyl esters Chemical class 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
208000022925 sleep disturbance Diseases 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
206010043118 Tardive Dyskinesia Diseases 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000003457 sulfones Chemical group 0.000 claims description 2
150000003462 sulfoxides Chemical group 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
229920000297 Rayon Polymers 0.000 claims 1
241001582326 Renia Species 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
230000002496 gastric effect Effects 0.000 claims 1
239000002964 rayon Substances 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 10
238000003786 synthesis reaction Methods 0.000 abstract description 8
208000012902 Nervous system disease Diseases 0.000 abstract 1
208000025966 Neurological disease Diseases 0.000 abstract 1
230000000926 neurological effect Effects 0.000 abstract 1
208000020016 psychiatric disease Diseases 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 118
238000006243 chemical reaction Methods 0.000 description 91
239000000203 mixture Substances 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
238000004809 thin layer chromatography Methods 0.000 description 53
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
239000003921 oil Substances 0.000 description 50
235000019198 oils Nutrition 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
238000005481 NMR spectroscopy Methods 0.000 description 47
230000000875 corresponding effect Effects 0.000 description 45
239000007864 aqueous solution Substances 0.000 description 44
239000000243 solution Substances 0.000 description 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
239000012044 organic layer Substances 0.000 description 35
239000007787 solid Substances 0.000 description 29
239000002904 solvent Substances 0.000 description 28
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
238000010992 reflux Methods 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000010410 layer Substances 0.000 description 24
239000000047 product Substances 0.000 description 24
239000012267 brine Substances 0.000 description 23
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
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235000019439 ethyl acetate Nutrition 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000002585 base Substances 0.000 description 17
238000002360 preparation method Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
229920000742 Cotton Polymers 0.000 description 14
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 14
238000003756 stirring Methods 0.000 description 14
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 14
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
125000006239 protecting group Chemical group 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
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101150067286 STS1 gene Proteins 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
238000005755 formation reaction Methods 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
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238000012360 testing method Methods 0.000 description 9
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239000000126 substance Substances 0.000 description 8
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
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235000011056 potassium acetate Nutrition 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 5
JGQFVRIQXUFPAH-UHFFFAOYSA-N α-citronellol Chemical compound OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
102100033891 Arylsulfatase I Human genes 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
101000925544 Homo sapiens Arylsulfatase I Proteins 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
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Veterinary Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
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Psychiatry (AREA)
Pain & Pain Management (AREA)
Addiction (AREA)
Psychology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Diabetes (AREA)
Anesthesiology (AREA)
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UA2000095418A 1998-04-29 1999-08-04 Azapolycyclic compounds condensed with aryl, intermediate compounds (variants), pharmaceutical composition (variants), a method for lowering the nicotine dependence and help to stop or lower the tobacco use by a mammal, and a method for treatment UA61991C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8355698P	1998-04-29	1998-04-29
PCT/IB1999/000617 WO1999055680A1 (en)	1998-04-29	1999-04-08	Aryl fused azapolycyclic compounds

Publications (1)

Publication Number	Publication Date
UA61991C2 true UA61991C2 (en)	2003-12-15

Family

ID=22179102

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2000095418A UA61991C2 (en)	1998-04-29	1999-08-04	Azapolycyclic compounds condensed with aryl, intermediate compounds (variants), pharmaceutical composition (variants), a method for lowering the nicotine dependence and help to stop or lower the tobacco use by a mammal, and a method for treatment

Country Status (41)

Country	Link
US (3)	US6462035B1 (de)
EP (1)	EP1076650B1 (de)
JP (1)	JP2002513007A (de)
KR (1)	KR100420423B1 (de)
CN (1)	CN1144787C (de)
AP (1)	AP1154A (de)
AR (1)	AR018596A1 (de)
AT (1)	ATE258921T1 (de)
AU (1)	AU749831B2 (de)
BG (1)	BG64556B1 (de)
BR (1)	BR9910058A (de)
CA (1)	CA2330576A1 (de)
CO (1)	CO5021124A1 (de)
DE (1)	DE69914594T2 (de)
DK (1)	DK1076650T3 (de)
DZ (1)	DZ2778A1 (de)
EA (1)	EA003669B1 (de)
ES (1)	ES2213354T3 (de)
GT (1)	GT199900059A (de)
HR (1)	HRP20000731A2 (de)
HU (1)	HUP0103340A3 (de)
ID (1)	ID26700A (de)
IL (1)	IL138917A0 (de)
IS (1)	IS5649A (de)
MA (1)	MA26623A1 (de)
MY (1)	MY133474A (de)
NO (1)	NO317300B1 (de)
NZ (1)	NZ507035A (de)
OA (1)	OA11506A (de)
PA (1)	PA8471301A1 (de)
PE (1)	PE20000435A1 (de)
PL (1)	PL344010A1 (de)
PT (1)	PT1076650E (de)
SK (1)	SK15952000A3 (de)
TN (1)	TNSN99080A1 (de)
TR (1)	TR200003122T2 (de)
UA (1)	UA61991C2 (de)
UY (1)	UY25636A1 (de)
WO (1)	WO1999055680A1 (de)
YU (1)	YU64400A (de)
ZA (1)	ZA992971B (de)

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US6605610B1 (en) *	1997-12-31	2003-08-12	Pfizer Inc	Aryl fused azapolycyclic compounds
PT1044189E (pt)	1997-12-31	2008-04-22	Pfizer Prod Inc	Compostos azapolicíclicos condensados com arilo
US20010036943A1 (en) *	2000-04-07	2001-11-01	Coe Jotham W.	Pharmaceutical composition for treatment of acute, chronic pain and/or neuropathic pain and migraines
PT1383733E (pt)	2001-04-20	2008-04-15	Pfizer Prod Inc	Processo para a preparação de indenos 1,3-substituídos e compostos azapolicíclicos fundidos com arilo
PL370549A1 (en) *	2001-10-31	2005-05-30	Pfizer Products Inc.	Nicotinic acetylcholine receptor agonists in the treatment of restless legs syndrome
DE60228478D1 (de)	2001-11-30	2008-10-02	Pfizer Prod Inc	Aryl-annellierte azapolyzyklische verbindungen
US20060089400A1 (en) *	2002-05-03	2006-04-27	The Vernalis Group Of Companies	Novel spiro ketone and carboxylic acid derivatives as specific inhibitors for (po3h2) ser/(po3h2)thr-pro-specific peptidyl-prolylcis/trans-isomerases
US20040224963A1 (en) *	2003-05-09	2004-11-11	Pfizer Inc	Pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal
US20040224962A1 (en) *	2003-05-09	2004-11-11	Pfizer Inc	Pharmaceutical composition for the treatment of obesity or to facilitate or promote weight loss
ES2331245T3 (es) *	2003-07-21	2009-12-28	Pfizer Products Inc.	Compuestos azapoliciclicos condensados con heteroarilo que reducen la adiccion a la nicotina.
MXPA06000892A (es) *	2003-07-21	2006-03-30	Pfizer Prod Inc	Compuestos azapoliciclicos arilo fusionados.
US20050043407A1 (en) *	2003-08-22	2005-02-24	Pfizer Inc	Pharmaceutical composition for the prevention and treatment of addiction in a mammal
CA2591330A1 (en) *	2004-12-07	2006-06-15	Pfizer Products Inc.	1, 2, 3, 3a, 8, 8a-hexahydro-2, 7a-diada-cyclopenta [a] inden-7-one derivatives which bind to neuronal nicotinic acetylcholine specific receptor sites and are useful in modulatingcholinergic function and in the treatment of addictive disorders
US20060210497A1 (en) *	2005-03-18	2006-09-21	Unilever Home & Personal Care Usa, Division Of Conopco, Inc.	Novel resorcinol derivatives
US20060210498A1 (en)	2005-03-18	2006-09-21	Unilever Home & Personal Care Usa, Division Of Conopco, Inc.	Novel resorcinol derivatives for skin
DE102005061426A1 (de) *	2005-12-22	2007-07-05	Grünenthal GmbH	Substituierte tricyclische Piperidon-Derivate

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US3687937A (en) *	1970-06-23	1972-08-29	Us Of America The	1,5-methano-3-benzazocine derivatives
JPS4914473A (de) *	1972-06-09	1974-02-07
JPS4924968A (de) *	1972-07-01	1974-03-05

1999
- 1999-04-08 WO PCT/IB1999/000617 patent/WO1999055680A1/en not_active Ceased
- 1999-04-08 DK DK99910600T patent/DK1076650T3/da active
- 1999-04-08 PL PL99344010A patent/PL344010A1/xx unknown
- 1999-04-08 CA CA002330576A patent/CA2330576A1/en not_active Abandoned
- 1999-04-08 US US09/582,513 patent/US6462035B1/en not_active Expired - Fee Related
- 1999-04-08 AT AT99910600T patent/ATE258921T1/de not_active IP Right Cessation
- 1999-04-08 YU YU64400A patent/YU64400A/sh unknown
- 1999-04-08 DE DE69914594T patent/DE69914594T2/de not_active Expired - Fee Related
- 1999-04-08 HR HR20000731A patent/HRP20000731A2/hr not_active Application Discontinuation
- 1999-04-08 HU HU0103340A patent/HUP0103340A3/hu unknown
- 1999-04-08 PT PT99910600T patent/PT1076650E/pt unknown
- 1999-04-08 TR TR2000/03122T patent/TR200003122T2/xx unknown
- 1999-04-08 JP JP2000545840A patent/JP2002513007A/ja not_active Withdrawn
- 1999-04-08 NZ NZ507035A patent/NZ507035A/en unknown
- 1999-04-08 EP EP99910600A patent/EP1076650B1/de not_active Expired - Lifetime
- 1999-04-08 KR KR10-2000-7012039A patent/KR100420423B1/ko not_active Expired - Fee Related
- 1999-04-08 BR BR9910058-4A patent/BR9910058A/pt not_active Application Discontinuation
- 1999-04-08 ES ES99910600T patent/ES2213354T3/es not_active Expired - Lifetime
- 1999-04-08 ID IDW20002185A patent/ID26700A/id unknown
- 1999-04-08 EA EA200000996A patent/EA003669B1/ru not_active IP Right Cessation
- 1999-04-08 SK SK1595-2000A patent/SK15952000A3/sk unknown
- 1999-04-08 IL IL13891799A patent/IL138917A0/xx unknown
- 1999-04-08 AU AU29516/99A patent/AU749831B2/en not_active Ceased
- 1999-04-08 CN CNB998054542A patent/CN1144787C/zh not_active Expired - Fee Related
- 1999-04-20 GT GT199900059A patent/GT199900059A/es unknown
- 1999-04-23 PE PE1999000340A patent/PE20000435A1/es not_active Application Discontinuation
- 1999-04-27 MY MYPI99001648A patent/MY133474A/en unknown
- 1999-04-27 AR ARP990101941A patent/AR018596A1/es unknown
- 1999-04-28 MA MA25556A patent/MA26623A1/fr unknown
- 1999-04-28 TN TNTNSN99080A patent/TNSN99080A1/fr unknown
- 1999-04-28 DZ DZ990078A patent/DZ2778A1/xx active
- 1999-04-28 ZA ZA9902971A patent/ZA992971B/xx unknown
- 1999-04-29 PA PA19998471301A patent/PA8471301A1/es unknown
- 1999-04-29 AP APAP/P/1999/001524A patent/AP1154A/en active
- 1999-04-29 CO CO99026005A patent/CO5021124A1/es unknown
- 1999-08-03 UY UY25636A patent/UY25636A1/es not_active Application Discontinuation
- 1999-08-04 UA UA2000095418A patent/UA61991C2/uk unknown
2000
- 2000-09-29 IS IS5649A patent/IS5649A/is unknown
- 2000-10-25 OA OA1200000295A patent/OA11506A/en unknown
- 2000-10-26 NO NO20005397A patent/NO317300B1/no unknown
- 2000-11-24 BG BG104983A patent/BG64556B1/bg unknown
2002
- 2002-08-13 US US10/217,771 patent/US6706702B2/en not_active Expired - Fee Related
2004
- 2004-01-23 US US10/764,167 patent/US7122534B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20030008890A1 (en)	2003-01-09
AP1154A (en)	2003-03-27
DZ2778A1 (fr)	2005-04-23
AP9901524A0 (en)	1999-06-30
TR200003122T2 (tr)	2001-03-21
EA200000996A1 (ru)	2001-06-25
PA8471301A1 (es)	2000-09-29
DK1076650T3 (da)	2004-05-24
MY133474A (en)	2007-11-30
HRP20000731A2 (en)	2001-06-30
ID26700A (id)	2001-02-01
HUP0103340A3 (en)	2002-10-28
SK15952000A3 (sk)	2002-06-04
CO5021124A1 (es)	2001-03-27
AU749831B2 (en)	2002-07-04
HUP0103340A2 (hu)	2002-02-28
PT1076650E (pt)	2004-05-31
US6462035B1 (en)	2002-10-08
YU64400A (sh)	2003-01-31
AU2951699A (en)	1999-11-16
KR20010043143A (ko)	2001-05-25
ZA992971B (en)	2000-10-30
DE69914594T2 (de)	2004-12-09
BG64556B1 (bg)	2005-07-29
NO317300B1 (no)	2004-10-04
OA11506A (en)	2004-05-14
CN1298394A (zh)	2001-06-06
ES2213354T3 (es)	2004-08-16
EA003669B1 (ru)	2003-08-28
AR018596A1 (es)	2001-11-28
CN1144787C (zh)	2004-04-07
GT199900059A (es)	2000-10-11
CA2330576A1 (en)	1999-11-04
BR9910058A (pt)	2000-12-26
PE20000435A1 (es)	2000-05-26
US6706702B2 (en)	2004-03-16
NZ507035A (en)	2003-05-30
EP1076650B1 (de)	2004-02-04
WO1999055680A1 (en)	1999-11-04
TNSN99080A1 (fr)	2005-11-10
IS5649A (is)	2000-09-29
BG104983A (en)	2001-09-28
ATE258921T1 (de)	2004-02-15
PL344010A1 (en)	2001-09-24
US20040167149A1 (en)	2004-08-26
MA26623A1 (fr)	2004-12-20
HK1036453A1 (en)	2002-01-04
JP2002513007A (ja)	2002-05-08
IL138917A0 (en)	2001-11-25
US7122534B2 (en)	2006-10-17
NO20005397L (no)	2000-10-26
NO20005397D0 (no)	2000-10-26
UY25636A1 (es)	2000-02-23
KR100420423B1 (ko)	2004-03-04
DE69914594D1 (de)	2004-03-11
EP1076650A1 (de)	2001-02-21

Publication	Publication Date	Title
US20030130261A1 (en)	2003-07-10	Aryl fused azapolycyclic compounds
KR100551183B1 (ko)	2006-02-13	1,3-치환 인덴 및 아릴-융합 아자폴리시클릭 화합물의제조 방법
HRP20050506A2 (en)	2006-03-31	Aryl fused azapolycyclic compounds
KR100420423B1 (ko)	2004-03-04	아릴 축합된 아자 다환식 화합물
KR20110011653A (ko)	2011-02-08	테트라히드로이소퀴놀린의 제조 방법
AU2002234836A1 (en)	2003-04-17	Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds
EP1648893B1 (de)	2009-09-23	Nikotin abhängigkeit reduzierende heteroaryl kondensierte azapolycyclische verbindungen
AU2017356911A1 (en)	2019-06-20	Tricyclic sulfones as ROR gamma modulators
WO1995026187A1 (fr)	1995-10-05	Agent anxiolytique
CN121851000A (zh)	2026-04-14	具有cyp1a1抑制活性与抗菌活性的双功能分子及制备方法和应用
Elkanzi	2014	Synthesis of New Isolated Pyrazolo, Isoxazolo Derivatives Incorporating Pyrido [1, 2] thiazinoquinoline
MXPA00010540A (en)	2001-09-07	Aryl fused azapolycyclic compounds
HK1062170B (en)	2007-10-18	Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds