CA2513293A1 - Process for the preparation of aryl fused polycyclic lactams - Google Patents
Process for the preparation of aryl fused polycyclic lactams Download PDFInfo
- Publication number
- CA2513293A1 CA2513293A1 CA002513293A CA2513293A CA2513293A1 CA 2513293 A1 CA2513293 A1 CA 2513293A1 CA 002513293 A CA002513293 A CA 002513293A CA 2513293 A CA2513293 A CA 2513293A CA 2513293 A1 CA2513293 A1 CA 2513293A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- triene
- dodeca
- aza
- tricyclo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 title abstract description 10
- -1 polycyclic lactams Chemical class 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 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
- 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
- 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo 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
- 125000004963 sulfonylalkyl 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 16
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- 238000003786 synthesis reaction Methods 0.000 abstract description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 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
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000003951 lactams Chemical class 0.000 description 5
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- 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
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- 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
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- 239000003085 diluting agent Substances 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229960004889 salicylic acid Drugs 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
- 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- 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
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
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- 150000003335 secondary amines Chemical class 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000002002 slurry Substances 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
- 230000001148 spastic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (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)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44026603P | 2003-01-15 | 2003-01-15 | |
| US60/440,266 | 2003-01-15 | ||
| PCT/IB2004/000152 WO2004063164A1 (en) | 2003-01-15 | 2004-01-08 | Process for the preparation of aryl fused polycyclic lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2513293A1 true CA2513293A1 (en) | 2004-07-29 |
Family
ID=32713537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002513293A Abandoned CA2513293A1 (en) | 2003-01-15 | 2004-01-08 | 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) | KR20050101177A (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 |
|---|---|---|---|---|
| WO2004048318A1 (en) | 2002-11-25 | 2004-06-10 | Pfizer Products Inc. | Improved process for the preparation of 1,3-substituted indenes |
| RU2372323C1 (ru) * | 2008-04-15 | 2009-11-10 | Открытое акционерное общество Научно-производственное предприятие НИИПАВ (ОАО НПП НИИПАВ) | Способ получения высокомолекулярных аминов |
| US8039620B2 (en) * | 2008-05-22 | 2011-10-18 | Teva Pharmaceutical Industries Ltd. | Varenicline tosylate, an intermediate in the preparation process of varenicline L-tartrate |
| US20090318695A1 (en) * | 2008-06-19 | 2009-12-24 | Vinod Kumar Kansal | 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 |
|---|---|---|---|---|
| RU2132851C1 (ru) * | 1993-08-05 | 1999-07-10 | Синтекс (Ю.Эс.Эй) Инк. | Производные амидов, являющиеся ингибиторами матричных металлопротеаз, фармацевтическая композиция |
| RS50069B (sr) * | 1997-12-31 | 2009-01-22 | Pfizer Products Inc., | Aril kondenzovana azapoliciklična jedinjenja |
| US6605610B1 (en) * | 1997-12-31 | 2003-08-12 | Pfizer Inc | Aryl fused azapolycyclic compounds |
| WO2002085843A2 (en) * | 2001-04-20 | 2002-10-31 | Pfizer Products Inc. | Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic compounds |
-
2004
- 2004-01-08 BR BR0406670-7A patent/BRPI0406670A/pt not_active IP Right Cessation
- 2004-01-08 KR KR1020057013036A patent/KR20050101177A/ko not_active Ceased
- 2004-01-08 CN CNB2004800022895A patent/CN100363350C/zh not_active Expired - Fee Related
- 2004-01-08 RS YUP-2005/0513A patent/RS20050513A/sr unknown
- 2004-01-08 EP EP04700747A patent/EP1587794A1/en not_active Withdrawn
- 2004-01-08 KR KR1020077018129A patent/KR20070087258A/ko not_active Withdrawn
- 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 WO PCT/IB2004/000152 patent/WO2004063164A1/en not_active Ceased
- 2004-01-08 MX MXPA05007565A patent/MXPA05007565A/es unknown
- 2004-01-08 PL PL379373A patent/PL379373A1/pl not_active Application Discontinuation
- 2004-01-08 JP JP2006500307A patent/JP2006517202A/ja not_active Withdrawn
- 2004-01-08 AU AU2004203983A patent/AU2004203983A1/en not_active Abandoned
- 2004-01-08 RU RU2005122406/04A patent/RU2291862C2/ru not_active IP Right Cessation
- 2004-01-12 CL CL200400041A patent/CL2004000041A1/es unknown
- 2004-01-14 TW TW093100889A patent/TW200420286A/zh unknown
- 2004-01-14 AR ARP040100091A patent/AR042855A1/es not_active Application Discontinuation
-
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 |
|---|---|
| AU2004203983A1 (en) | 2004-07-29 |
| KR20050101177A (ko) | 2005-10-20 |
| IL169479A0 (en) | 2007-07-04 |
| WO2004063164A1 (en) | 2004-07-29 |
| CN100363350C (zh) | 2008-01-23 |
| CN1738803A (zh) | 2006-02-22 |
| MXPA05007565A (es) | 2005-09-21 |
| BRPI0406670A (pt) | 2005-12-20 |
| EP1587794A1 (en) | 2005-10-26 |
| RU2005122406A (ru) | 2006-01-27 |
| JP2006517202A (ja) | 2006-07-20 |
| RS20050513A (sr) | 2007-11-15 |
| US20070066827A1 (en) | 2007-03-22 |
| ZA200505103B (en) | 2006-11-29 |
| PL379373A1 (pl) | 2006-08-21 |
| KR20070087258A (ko) | 2007-08-27 |
| AR042855A1 (es) | 2005-07-06 |
| CL2004000041A1 (es) | 2005-04-22 |
| HK1085204A1 (zh) | 2006-08-18 |
| TW200420286A (en) | 2004-10-16 |
| WO2004063164A8 (en) | 2005-05-26 |
| RU2291862C2 (ru) | 2007-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |