AU2003212268B2 - Pharmaceutical composition of a PDE4 or PDE3/4 inhibitor and a histamine receptor antagonist - Google Patents
Pharmaceutical composition of a PDE4 or PDE3/4 inhibitor and a histamine receptor antagonist Download PDFInfo
- Publication number
- AU2003212268B2 AU2003212268B2 AU2003212268A AU2003212268A AU2003212268B2 AU 2003212268 B2 AU2003212268 B2 AU 2003212268B2 AU 2003212268 A AU2003212268 A AU 2003212268A AU 2003212268 A AU2003212268 A AU 2003212268A AU 2003212268 B2 AU2003212268 B2 AU 2003212268B2
- Authority
- AU
- Australia
- Prior art keywords
- inn
- tetrahydro
- active ingredient
- pharmaceutically acceptable
- phthalazin
- 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.)
- Ceased
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 33
- 239000003112 inhibitor Substances 0.000 title description 23
- 229940122236 Histamine receptor antagonist Drugs 0.000 title description 18
- 101100135868 Dictyostelium discoideum pde3 gene Proteins 0.000 title description 16
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 title description 12
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 title description 12
- 239000000739 antihistaminic agent Substances 0.000 title description 12
- 239000004480 active ingredient Substances 0.000 claims description 109
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 83
- 238000002360 preparation method Methods 0.000 claims description 64
- -1 dichloropyrid-4-yl Chemical group 0.000 claims description 47
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 47
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 40
- 239000012453 solvate Substances 0.000 claims description 32
- 150000001204 N-oxides Chemical class 0.000 claims description 31
- 229960002586 roflumilast Drugs 0.000 claims description 28
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 23
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 21
- 229940127557 pharmaceutical product Drugs 0.000 claims description 19
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- CVDXFPBVOIERBH-JWQCQUIFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-JWQCQUIFSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 208000023504 respiratory system disease Diseases 0.000 claims description 14
- ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
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- CVDXFPBVOIERBH-DQEYMECFSA-N 4-[(4as,10br)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-DQEYMECFSA-N 0.000 claims description 5
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- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 206010039094 Rhinitis perennial Diseases 0.000 claims description 3
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- 230000001932 seasonal effect Effects 0.000 claims description 3
- PVMRLPYQMWDVSK-UHFFFAOYSA-N 4-(1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin-6-yl)-N,N-di(propan-2-yl)benzamide Chemical compound CC(C)N(C(C)C)C(=O)c1ccc(cc1)C1=NC2CCNCC2c2ccccc12 PVMRLPYQMWDVSK-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- LJXMVHHXVQDMPN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-(difluoromethoxy)benzamide Chemical compound FC(F)OC1=CC=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl LJXMVHHXVQDMPN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 38
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 22
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 22
- SFOVDSLXFUGAIV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-piperidin-4-ylbenzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCNCC1 SFOVDSLXFUGAIV-UHFFFAOYSA-N 0.000 description 19
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- CWNCDQYLHMXURI-UHFFFAOYSA-N 3-[4-(8-fluoro-5h-[1]benzoxepino[4,3-b]pyridin-11-ylidene)piperidin-1-yl]propanoic acid;dihydrate Chemical compound O.O.C1CN(CCC(=O)O)CCC1=C1C2=NC=CC=C2COC2=CC(F)=CC=C21 CWNCDQYLHMXURI-UHFFFAOYSA-N 0.000 description 11
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- A61K9/0012—Galenical forms characterised by the site of application
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02004987.0 | 2002-03-06 | ||
| EP02004987 | 2002-03-06 | ||
| PCT/EP2003/001876 WO2003074055A1 (en) | 2002-03-06 | 2003-02-25 | Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003212268A1 AU2003212268A1 (en) | 2003-09-16 |
| AU2003212268B2 true AU2003212268B2 (en) | 2008-09-11 |
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| AU2003212268A Ceased AU2003212268B2 (en) | 2002-03-06 | 2003-02-25 | Pharmaceutical composition of a PDE4 or PDE3/4 inhibitor and a histamine receptor antagonist |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US20050112069A1 (https=) |
| EP (2) | EP1482938B1 (https=) |
| JP (1) | JP5150034B2 (https=) |
| KR (1) | KR20040095255A (https=) |
| CN (1) | CN101257904A (https=) |
| AR (1) | AR038858A1 (https=) |
| AT (1) | ATE369134T1 (https=) |
| AU (1) | AU2003212268B2 (https=) |
| BR (1) | BR0308220A (https=) |
| CA (1) | CA2478612C (https=) |
| CO (1) | CO5611148A2 (https=) |
| CY (2) | CY1106927T1 (https=) |
| DE (1) | DE60315426T2 (https=) |
| DK (2) | DK1849468T3 (https=) |
| EA (2) | EA007903B1 (https=) |
| ES (2) | ES2291618T3 (https=) |
| HR (1) | HRP20040909B1 (https=) |
| IL (1) | IL163336A (https=) |
| IS (2) | IS2536B (https=) |
| MX (1) | MXPA04008460A (https=) |
| NO (1) | NO335254B1 (https=) |
| NZ (1) | NZ535611A (https=) |
| PL (1) | PL211574B1 (https=) |
| PT (2) | PT1482938E (https=) |
| RS (1) | RS51018B (https=) |
| SG (1) | SG160197A1 (https=) |
| SI (2) | SI1849468T1 (https=) |
| TW (1) | TWI347845B (https=) |
| UA (1) | UA80117C2 (https=) |
| WO (1) | WO2003074055A1 (https=) |
| ZA (1) | ZA200407104B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007056457A2 (en) * | 2005-11-09 | 2007-05-18 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
| ATE459358T1 (de) * | 2006-12-20 | 2010-03-15 | Glaxo Group Ltd | 4-benzyl-1(2h)-phthalazinone als h1-rezeptor- antagonisten |
| US20090182035A1 (en) * | 2007-04-11 | 2009-07-16 | Alcon Research, Ltd. | Use of a combination of olopatadine and cilomilast to treat non-infectious rhinitis and allergic conjunctivitis |
| TW200902025A (en) * | 2007-04-11 | 2009-01-16 | Alcon Res Ltd | Use of an inhibitor of TNF α plus an antihistamine to treat allergic rhinitis and allergic conjunctivitis |
| WO2009067597A1 (en) * | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf | 4- (or 5-) substituted catechol derivatives |
| KR20090061972A (ko) * | 2007-12-12 | 2009-06-17 | 한미약품 주식회사 | 베포타스틴 ｐ-톨루엔술폰산염의 결정형, 이의 제조방법 및이를 포함하는 약학 조성물 |
| LT2672957T (lt) | 2011-02-07 | 2017-02-10 | Scipharm Sarl | Naujoji kompozicija, skirta cistinės fibrozės gydymui |
| KR102226833B1 (ko) * | 2013-06-28 | 2021-03-12 | 한미약품 주식회사 | 레보세티리진 및 몬테루카스트를 포함하는 안정성이 개선된 복합 과립 제형 |
| JP2017525721A (ja) * | 2014-08-26 | 2017-09-07 | ファンダシオン パラ ラ インベスティガシオン メディカ アプリカダＦｕｎｄａｃｉｏｎ Ｐａｒａ Ｌａ Ｉｎｖｅｓｔｉｇａｓｉｏｎ Ｍｅｄｉｃａ Ａｐｌｉｃａｄａ | 認知欠損または認知障害に伴って進行する神経障害のおよび神経変性疾患の処置および予防のための製品 |
| CN107001371B (zh) * | 2014-10-09 | 2019-07-05 | 广东众生睿创生物科技有限公司 | 羟基嘌呤类化合物及其应用 |
| CN109956947A (zh) * | 2017-12-25 | 2019-07-02 | 江苏恒瑞医药股份有限公司 | 一种cns抑制剂的新晶型、制备方法及用途 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962464A (en) * | 1997-02-11 | 1999-10-05 | Sepracor Inc. | Methods and compositions for treating allergic asthma using descarboethoxyloratadine |
| EP1005865A1 (en) * | 1998-11-10 | 2000-06-07 | Panacea Biotec Limited | A anti-allergy anti-inflammatory composition comprising nimesulide and cetirizine |
| WO2001030777A1 (en) * | 1999-10-25 | 2001-05-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydrothiopy ranphthalazinone derivatives as pde4 inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| AU650953B2 (en) | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| ES2176252T3 (es) * | 1993-07-02 | 2002-12-01 | Altana Pharma Ag | Benzamidas sustituidas con fluoro-alcoxi y su utilizacion como agentes inhibidores de fosfodiesterasas de nucleotidos ciclicos. |
| US5990147A (en) * | 1997-11-07 | 1999-11-23 | Schering Corporation | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| US6174878B1 (en) * | 1999-08-31 | 2001-01-16 | Alcon Laboratories, Inc. | Topical use of kappa opioid agonists to treat otic pain |
| US7585847B2 (en) * | 2000-02-03 | 2009-09-08 | Coley Pharmaceutical Group, Inc. | Immunostimulatory nucleic acids for the treatment of asthma and allergy |
| GB0115181D0 (en) | 2001-06-20 | 2001-08-15 | Glaxo Group Ltd | Novel use |
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2003
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- 2003-02-25 RS YUP-780/04A patent/RS51018B/sr unknown
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- 2003-02-25 DE DE60315426T patent/DE60315426T2/de not_active Expired - Lifetime
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- 2003-02-25 ES ES03708130T patent/ES2291618T3/es not_active Expired - Lifetime
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- 2003-02-25 EP EP07112823A patent/EP1849468B1/en not_active Expired - Lifetime
- 2003-02-25 EA EA200601592A patent/EA010886B1/ru not_active IP Right Cessation
- 2003-02-25 UA UA20041008055A patent/UA80117C2/uk unknown
- 2003-02-25 ES ES07112823T patent/ES2400670T3/es not_active Expired - Lifetime
- 2003-02-25 PL PL371056A patent/PL211574B1/pl unknown
- 2003-02-25 DK DK03708130T patent/DK1482938T3/da active
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- 2003-02-25 MX MXPA04008460A patent/MXPA04008460A/es active IP Right Grant
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2004
- 2004-08-03 IL IL163336A patent/IL163336A/en not_active IP Right Cessation
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- 2004-09-03 IS IS7438A patent/IS2536B/is unknown
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2007
- 2007-10-11 CY CY20071101307T patent/CY1106927T1/el unknown
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2008
- 2008-09-04 IS IS8760A patent/IS8760A/is unknown
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2013
- 2013-02-21 CY CY20131100163T patent/CY1113894T1/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962464A (en) * | 1997-02-11 | 1999-10-05 | Sepracor Inc. | Methods and compositions for treating allergic asthma using descarboethoxyloratadine |
| EP1005865A1 (en) * | 1998-11-10 | 2000-06-07 | Panacea Biotec Limited | A anti-allergy anti-inflammatory composition comprising nimesulide and cetirizine |
| WO2001030777A1 (en) * | 1999-10-25 | 2001-05-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydrothiopy ranphthalazinone derivatives as pde4 inhibitors |
Non-Patent Citations (2)
| Title |
|---|
| Andri L et al. Allergie et Immunologie 1992 Vol. 24(8) pp313-314, 317-319 * |
| Hatzelmann A et al. J, Pharmacol. Exp. Therapeut. 2001 Vol. 297(1) pp267-279 * |
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