ZA200006483B - Gamma-aminobutyric acid derivatives containing, solid compositions and process for preparing the same. - Google Patents
Gamma-aminobutyric acid derivatives containing, solid compositions and process for preparing the same. Download PDFInfo
- Publication number
- ZA200006483B ZA200006483B ZA200006483A ZA200006483A ZA200006483B ZA 200006483 B ZA200006483 B ZA 200006483B ZA 200006483 A ZA200006483 A ZA 200006483A ZA 200006483 A ZA200006483 A ZA 200006483A ZA 200006483 B ZA200006483 B ZA 200006483B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- carbon atoms
- ring
- substituted
- amino
- Prior art date
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- 239000008247 solid mixture Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical class NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 167
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 82
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 75
- 125000003277 amino group Chemical group 0.000 claims description 72
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 69
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 62
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 50
- 125000004414 alkyl thio group Chemical group 0.000 claims description 44
- 229960002870 gabapentin Drugs 0.000 claims description 31
- -1 4-amino-3-substituted- butanoic acid Chemical class 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 17
- 239000003906 humectant Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- 239000002775 capsule Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
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- 239000000203 mixture Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003826 tablet Substances 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000012752 auxiliary agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 229960000794 baclofen Drugs 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 4
- 229960001233 pregabalin Drugs 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 3
- 229940024606 amino acid Drugs 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000000600 sorbitol Substances 0.000 claims 3
- WAULXXVONWOJBD-UHFFFAOYSA-N 3-(aminomethyl)-4-cyclohexylbutanoic acid Chemical compound OC(=O)CC(CN)CC1CCCCC1 WAULXXVONWOJBD-UHFFFAOYSA-N 0.000 claims 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N Isoleucine Chemical compound CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- SMWZNXFMLNNMFB-UHFFFAOYSA-N 3-(aminomethyl)-4-phenylbutanoic acid Chemical compound OC(=O)CC(CN)CC1=CC=CC=C1 SMWZNXFMLNNMFB-UHFFFAOYSA-N 0.000 claims 1
- NDPMXDOHYXRXHS-UHFFFAOYSA-N 3-(aminomethyl)-5-cyclohexylpentanoic acid Chemical compound OC(=O)CC(CN)CCC1CCCCC1 NDPMXDOHYXRXHS-UHFFFAOYSA-N 0.000 claims 1
- BYHDDXPKOZIZRV-UHFFFAOYSA-N 5-phenylpentanoic acid Chemical compound OC(=O)CCCCC1=CC=CC=C1 BYHDDXPKOZIZRV-UHFFFAOYSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-RFZPGFLSSA-N D-Isoleucine Chemical compound CC[C@@H](C)[C@@H](N)C(O)=O AGPKZVBTJJNPAG-RFZPGFLSSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 claims 1
- 229930182819 D-leucine Natural products 0.000 claims 1
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 claims 1
- 229930182831 D-valine Natural products 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- 229930182844 L-isoleucine Natural products 0.000 claims 1
- 239000004395 L-leucine Substances 0.000 claims 1
- 235000019454 L-leucine Nutrition 0.000 claims 1
- 229960003767 alanine Drugs 0.000 claims 1
- 229950010030 dl-alanine Drugs 0.000 claims 1
- 229960002449 glycine Drugs 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 229960003136 leucine Drugs 0.000 claims 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
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- 229940079593 drug Drugs 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
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- PWSUQCRPENFXDF-UHFFFAOYSA-N 4-cyclohexylpyrrolidin-2-one Chemical compound C1NC(=O)CC1C1CCCCC1 PWSUQCRPENFXDF-UHFFFAOYSA-N 0.000 description 2
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- AYXYPKUFHZROOJ-UHFFFAOYSA-N 3-(azaniumylmethyl)-5-methylhexanoate Chemical compound CC(C)CC(CN)CC(O)=O AYXYPKUFHZROOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
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- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
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- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13311298 | 1998-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006483B true ZA200006483B (en) | 2002-04-09 |
Family
ID=15097099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006483A ZA200006483B (en) | 1998-05-15 | 2000-11-09 | Gamma-aminobutyric acid derivatives containing, solid compositions and process for preparing the same. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8623407B2 (is) |
| EP (1) | EP1077691B1 (is) |
| JP (3) | JP4564607B2 (is) |
| KR (1) | KR100669280B1 (is) |
| CN (1) | CN100337687C (is) |
| AR (1) | AR018609A1 (is) |
| AU (1) | AU769038B2 (is) |
| BR (1) | BR9910494B1 (is) |
| CO (1) | CO5060516A1 (is) |
| CU (1) | CU23051A3 (is) |
| GT (1) | GT199900068A (is) |
| HK (2) | HK1036407A1 (is) |
| HU (1) | HU228772B1 (is) |
| ID (1) | ID26395A (is) |
| IS (1) | IS2983B (is) |
| MY (1) | MY127953A (is) |
| NO (1) | NO329116B1 (is) |
| PA (1) | PA8472701A1 (is) |
| PE (1) | PE20000542A1 (is) |
| PL (1) | PL205145B1 (is) |
| SV (1) | SV1999000063A (is) |
| TW (1) | TW592691B (is) |
| UY (1) | UY25513A1 (is) |
| WO (1) | WO1999059572A1 (is) |
| ZA (1) | ZA200006483B (is) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU714980B2 (en) | 1996-07-24 | 2000-01-13 | Warner-Lambert Company Llc | Isobutylgaba and its derivatives for the treatment of pain |
| AU2001268426A1 (en) * | 2000-06-16 | 2002-01-02 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin containing more than 2o ppm of chlorine ion |
| EP1430893A1 (en) * | 2000-06-16 | 2004-06-23 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin containing more than 20 ppm of chloride ion |
| SK302003A3 (en) * | 2000-06-16 | 2003-07-01 | Teva Pharma | Stable gabapentin having pH within a controlled range |
| EP1384473A1 (en) * | 2000-06-16 | 2004-01-28 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin containing more than 20 ppm of chlorine ion |
| US7056951B2 (en) * | 2000-09-26 | 2006-06-06 | Mutual Pharmaceutical Co., Inc. | Stable solid dosage forms of amino acids and processes for producing same |
| AU2002214305A1 (en) * | 2000-11-17 | 2002-05-27 | Takeda Chemical Industries Ltd. | Pharmaceutical preparation containing copolyvidone |
| EP1558218A1 (en) * | 2002-10-08 | 2005-08-03 | Ranbaxy Laboratories Limited | Gabapentin tablets and methods for their preparation |
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| CN107920987A (zh) | 2015-05-26 | 2018-04-17 | 艾萨·欧蒂迪 | 控制延缓释放普瑞巴林 |
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| JP6919119B2 (ja) * | 2017-01-23 | 2021-08-18 | 日新製薬株式会社 | ３位が置換されたγ−アミノ酪酸誘導体を含有する圧縮固形医薬組成物。 |
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1999
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- 1999-05-10 EP EP99924164A patent/EP1077691B1/en not_active Expired - Lifetime
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- 1999-05-10 HU HU0101791A patent/HU228772B1/hu not_active IP Right Cessation
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