PT99831A - Processo para a preparacao de derivados de acido benzoico contendo uma cadeia lateral di-azaciclica ou azabiciclica - Google Patents
Processo para a preparacao de derivados de acido benzoico contendo uma cadeia lateral di-azaciclica ou azabiciclica Download PDFInfo
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- PT99831A PT99831A PT99831A PT9983191A PT99831A PT 99831 A PT99831 A PT 99831A PT 99831 A PT99831 A PT 99831A PT 9983191 A PT9983191 A PT 9983191A PT 99831 A PT99831 A PT 99831A
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- pharmaceutically acceptable
- process according
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- 238000000034 method Methods 0.000 title claims description 26
- 150000001558 benzoic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 23
- -1 (8-methyl-8-azabicyclo [3.2.1] -octan-3-yl) -4-amino-3,5-dichloro- 2-methoxybenzamide Chemical compound 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 206010047700 Vomiting Diseases 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
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- 208000002193 Pain Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
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- 229930004006 tropane Natural products 0.000 claims description 4
- 229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
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- 238000011321 prophylaxis Methods 0.000 claims description 3
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 3
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 claims description 2
- XTZCYZPPSXSLKZ-UHFFFAOYSA-N 4-amino-n-(1-azabicyclo[2.2.2]octan-3-yl)-3,5-dichlorobenzamide Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(=O)NC1C(CC2)CCN2C1 XTZCYZPPSXSLKZ-UHFFFAOYSA-N 0.000 claims description 2
- ODWVFJUVKLPMDM-UHFFFAOYSA-N 9-methyl-9-azabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1N2C ODWVFJUVKLPMDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
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- 241000534944 Thia Species 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
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- 125000004423 acyloxy group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 4
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 239000005557 antagonist Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 2
- PEJTUMUHVFETQR-UHFFFAOYSA-N 4-amino-5-chloro-3-fluoro-2-methoxybenzoic acid Chemical compound COC1=C(F)C(N)=C(Cl)C=C1C(O)=O PEJTUMUHVFETQR-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
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- 238000005658 halogenation reaction Methods 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 230000000968 intestinal effect Effects 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 235000020824 obesity Nutrition 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
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- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 231100000759 toxicological effect Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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 Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909027487A GB9027487D0 (en) | 1990-12-19 | 1990-12-19 | Pharmaceuticals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT99831A true PT99831A (pt) | 1992-12-31 |
Family
ID=10687217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT99831A PT99831A (pt) | 1990-12-19 | 1991-12-17 | Processo para a preparacao de derivados de acido benzoico contendo uma cadeia lateral di-azaciclica ou azabiciclica |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0563087A1 (enExample) |
| JP (1) | JPH06503332A (enExample) |
| KR (1) | KR930703308A (enExample) |
| AU (1) | AU9053391A (enExample) |
| CA (1) | CA2098729A1 (enExample) |
| GB (1) | GB9027487D0 (enExample) |
| IE (1) | IE914395A1 (enExample) |
| MX (1) | MX9102630A (enExample) |
| NZ (1) | NZ241019A (enExample) |
| PT (1) | PT99831A (enExample) |
| TW (1) | TW226020B (enExample) |
| WO (1) | WO1992011259A1 (enExample) |
| ZA (1) | ZA919884B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9214184D0 (en) * | 1992-07-03 | 1992-08-12 | Smithkline Beecham Plc | Pharmaceuticals |
| GB9721139D0 (en) | 1997-10-07 | 1997-12-03 | Glaxo Group Ltd | Medicaments |
| AU2001282874A1 (en) * | 2000-08-18 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted aryl moieties for treatment of disease (nicotinic acetylcholine receptor ligands) |
| AU2001284645A1 (en) * | 2000-08-18 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| US6486172B2 (en) | 2000-08-18 | 2002-11-26 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| US6492385B2 (en) | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| US6599916B2 (en) | 2000-08-21 | 2003-07-29 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| WO2002017358A2 (en) | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists) |
| PE20021019A1 (es) | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
| MXPA04007936A (es) | 2002-02-15 | 2004-11-26 | Upjohn Co | Compuestos de aril-sustituidos para el tratamiento de enfermedades. |
| US7176198B2 (en) | 2002-08-01 | 2007-02-13 | Pfizer Inc. | 1H-pyrazole and 1H-pyrrole-azabicyclic compounds for the treatment of disease |
| TW200842733A (en) | 2007-04-17 | 2008-11-01 | Univ Nat Chiao Tung | Object image detection method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2476088A2 (fr) * | 1979-01-16 | 1981-08-21 | Delalande Sa | Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique |
| FR2529548A1 (fr) * | 1982-07-02 | 1984-01-06 | Delalande Sa | Nouveaux derives de l'amino-3 quinuclidine, leur procede et leur application en therapeutique |
| EP0220011A3 (en) * | 1985-10-12 | 1990-01-03 | Beecham Group Plc | Use of azabicloalkylbenzamides in the treatment of gastrointestinal motility disorders, migraine, emesis, cluster headaches, trigeminal neuralgia and arrhythmia |
| GB8829079D0 (en) * | 1988-12-13 | 1989-01-25 | Beecham Group Plc | Novel compounds |
-
1990
- 1990-12-19 GB GB909027487A patent/GB9027487D0/en active Pending
-
1991
- 1991-12-12 WO PCT/GB1991/002210 patent/WO1992011259A1/en not_active Ceased
- 1991-12-12 JP JP4501723A patent/JPH06503332A/ja active Pending
- 1991-12-12 CA CA002098729A patent/CA2098729A1/en not_active Abandoned
- 1991-12-12 EP EP92900452A patent/EP0563087A1/en not_active Withdrawn
- 1991-12-12 AU AU90533/91A patent/AU9053391A/en not_active Abandoned
- 1991-12-17 PT PT99831A patent/PT99831A/pt not_active Application Discontinuation
- 1991-12-17 MX MX9102630A patent/MX9102630A/es unknown
- 1991-12-17 NZ NZ24101991A patent/NZ241019A/en unknown
- 1991-12-17 ZA ZA919884A patent/ZA919884B/xx unknown
- 1991-12-17 IE IE439591A patent/IE914395A1/en not_active Application Discontinuation
- 1991-12-20 TW TW080110005A patent/TW226020B/zh active
-
1993
- 1993-06-18 KR KR1019930701884A patent/KR930703308A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NZ241019A (en) | 1994-07-26 |
| GB9027487D0 (en) | 1991-02-06 |
| ZA919884B (en) | 1992-10-28 |
| AU9053391A (en) | 1992-07-22 |
| EP0563087A1 (en) | 1993-10-06 |
| TW226020B (enExample) | 1994-07-01 |
| MX9102630A (es) | 1992-06-01 |
| IE914395A1 (en) | 1992-07-01 |
| CA2098729A1 (en) | 1992-06-20 |
| WO1992011259A1 (en) | 1992-07-09 |
| KR930703308A (ko) | 1993-11-29 |
| JPH06503332A (ja) | 1994-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19920713 |
|
| FC3A | Refusal |
Effective date: 19990224 |