MXPA06004278A - Preparacion de derivados de 3-azabiciclo [3.1.0]hexano. - Google Patents
Preparacion de derivados de 3-azabiciclo [3.1.0]hexano.Info
- Publication number
- MXPA06004278A MXPA06004278A MXPA06004278A MXPA06004278A MXPA06004278A MX PA06004278 A MXPA06004278 A MX PA06004278A MX PA06004278 A MXPA06004278 A MX PA06004278A MX PA06004278 A MXPA06004278 A MX PA06004278A MX PA06004278 A MXPA06004278 A MX PA06004278A
- Authority
- MX
- Mexico
- Prior art keywords
- hydroxy
- phenyl
- alkyl
- formula
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000005228 3‐azabicyclo[3.1.0]hexanes Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 35
- -1 -OH Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 159000000000 sodium salts Chemical class 0.000 claims description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 10
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- LNAMLTANBWXSPV-UHFFFAOYSA-N hydroxy-(2-hydroxy-1,3-dihydroinden-2-yl)methanesulfonic acid Chemical compound C1=CC=C2CC(C(O)S(O)(=O)=O)(O)CC2=C1 LNAMLTANBWXSPV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002947 alkylene group Chemical group 0.000 claims description 5
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- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 4
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- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical group CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 2
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- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 2
- HJUAYCORBOWWGO-UHFFFAOYSA-N [3-[6-ethyl-3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-3-azabicyclo[3.1.0]hexan-6-yl]phenyl]methanesulfonamide Chemical compound C12CN(CC3(O)CC4=CC=CC=C4C3)CC2C1(CC)C1=CC=CC(CS(N)(=O)=O)=C1 HJUAYCORBOWWGO-UHFFFAOYSA-N 0.000 claims description 2
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- 238000006268 reductive amination reaction Methods 0.000 abstract description 8
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- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- QJQRNDGUWQVAEV-AAFSJPGBSA-M sodium bisulfite adduct Chemical compound [Na+].[O-]S(=O)(=O)C([C@H]1N(C(C2=C3)=O)C=C(C1)/C=C/C(=O)N(C)C)NC2=CC1=C3OCO1 QJQRNDGUWQVAEV-AAFSJPGBSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51188903P | 2003-10-16 | 2003-10-16 | |
| PCT/IB2004/003261 WO2005037790A1 (en) | 2003-10-16 | 2004-10-06 | Preparation of 3-azabicyclo [3.1.0] hexane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06004278A true MXPA06004278A (es) | 2006-06-28 |
Family
ID=34465290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06004278A MXPA06004278A (es) | 2003-10-16 | 2004-10-06 | Preparacion de derivados de 3-azabiciclo [3.1.0]hexano. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7129263B2 (enExample) |
| EP (1) | EP1675829A1 (enExample) |
| JP (1) | JP2007508367A (enExample) |
| KR (1) | KR20060096038A (enExample) |
| CN (1) | CN1867548A (enExample) |
| AR (1) | AR046592A1 (enExample) |
| AU (1) | AU2004281229A1 (enExample) |
| BR (1) | BRPI0415459A (enExample) |
| CA (1) | CA2540860A1 (enExample) |
| CO (1) | CO5680416A2 (enExample) |
| IL (1) | IL174596A0 (enExample) |
| MX (1) | MXPA06004278A (enExample) |
| NO (1) | NO20062152L (enExample) |
| RU (1) | RU2006112576A (enExample) |
| TW (1) | TW200524866A (enExample) |
| WO (1) | WO2005037790A1 (enExample) |
| ZA (1) | ZA200601964B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2314289T3 (es) | 2002-12-10 | 2009-03-16 | Wyeth | Derivados del acido 1h-indol-3-il glioxilico sustituidos con arilo, ariloxi y alquloxi como inhibidores del inhibidor del activador del plasminogeno-1(pai-1). |
| MXPA06004279A (es) * | 2003-10-14 | 2006-06-28 | Pfizer Prod Inc | Derivados biciclicos [3.1.0] como inhibidores del transportador de glicina. |
| WO2008075162A2 (en) * | 2006-12-15 | 2008-06-26 | Pfizer Limited | Selective mu opioid receptor antagonists for the treatment of female sexual dysfunction |
| BR112013007566A2 (pt) | 2010-09-28 | 2016-08-02 | Panacea Biotec Ltd | novos compostos bicíclicos |
| EP3610890A1 (en) | 2012-11-14 | 2020-02-19 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| RU2701861C1 (ru) | 2013-11-20 | 2019-10-02 | Санва Кагаку Кенкюсо Ко., Лтд. | Новое производное 3-азабицикло[3.1.0]гексана и его применение в медицинских целях |
| CA2985327A1 (en) * | 2015-05-20 | 2016-11-24 | Sanwa Kagaku Kenkyusho Co., Ltd. | Crystal of salt of 3-azabicyclo[3.1.0]hexane derivative and pharmaceutical use thereof |
| WO2019173173A1 (en) * | 2018-03-05 | 2019-09-12 | E. I. Du Pont De Nemours And Company | Process and intermidiates for the preparation of certain mesoionic pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI244481B (en) * | 1998-12-23 | 2005-12-01 | Pfizer | 3-azabicyclo[3.1.0]hexane derivatives useful in therapy |
| EP1440059B1 (en) * | 2001-10-22 | 2008-04-16 | Pfizer Products Inc. | 3-azabicyclo(3.1.0)hexane derivatives as opioid receptor antagonists |
-
2004
- 2004-10-06 KR KR1020067007220A patent/KR20060096038A/ko not_active Ceased
- 2004-10-06 WO PCT/IB2004/003261 patent/WO2005037790A1/en not_active Ceased
- 2004-10-06 CN CNA2004800305305A patent/CN1867548A/zh active Pending
- 2004-10-06 CA CA002540860A patent/CA2540860A1/en not_active Abandoned
- 2004-10-06 JP JP2006534849A patent/JP2007508367A/ja not_active Abandoned
- 2004-10-06 RU RU2006112576/04A patent/RU2006112576A/ru not_active Application Discontinuation
- 2004-10-06 MX MXPA06004278A patent/MXPA06004278A/es not_active Application Discontinuation
- 2004-10-06 AU AU2004281229A patent/AU2004281229A1/en not_active Abandoned
- 2004-10-06 BR BRPI0415459-2A patent/BRPI0415459A/pt not_active IP Right Cessation
- 2004-10-06 EP EP04769571A patent/EP1675829A1/en not_active Withdrawn
- 2004-10-12 TW TW093130881A patent/TW200524866A/zh unknown
- 2004-10-14 AR ARP040103725A patent/AR046592A1/es not_active Application Discontinuation
- 2004-10-15 US US10/966,712 patent/US7129263B2/en not_active Expired - Fee Related
-
2006
- 2006-03-08 ZA ZA200601964A patent/ZA200601964B/en unknown
- 2006-03-27 IL IL174596A patent/IL174596A0/en unknown
- 2006-04-05 CO CO06033213A patent/CO5680416A2/es not_active Application Discontinuation
- 2006-05-12 NO NO20062152A patent/NO20062152L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7129263B2 (en) | 2006-10-31 |
| TW200524866A (en) | 2005-08-01 |
| JP2007508367A (ja) | 2007-04-05 |
| ZA200601964B (en) | 2007-04-25 |
| IL174596A0 (en) | 2006-08-20 |
| AR046592A1 (es) | 2005-12-14 |
| NO20062152L (no) | 2006-05-12 |
| CA2540860A1 (en) | 2005-04-28 |
| CN1867548A (zh) | 2006-11-22 |
| BRPI0415459A (pt) | 2006-12-19 |
| WO2005037790A1 (en) | 2005-04-28 |
| KR20060096038A (ko) | 2006-09-05 |
| US20050113437A1 (en) | 2005-05-26 |
| EP1675829A1 (en) | 2006-07-05 |
| RU2006112576A (ru) | 2006-08-27 |
| CO5680416A2 (es) | 2006-09-29 |
| AU2004281229A1 (en) | 2005-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |