DK2755964T3 - Sulfonsyresalte af heterocyclylamid-substituerede imidazoler - Google Patents
Sulfonsyresalte af heterocyclylamid-substituerede imidazoler Download PDFInfo
- Publication number
- DK2755964T3 DK2755964T3 DK12761936.9T DK12761936T DK2755964T3 DK 2755964 T3 DK2755964 T3 DK 2755964T3 DK 12761936 T DK12761936 T DK 12761936T DK 2755964 T3 DK2755964 T3 DK 2755964T3
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- Prior art keywords
- salt
- methyl
- formula
- infections
- compounds
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- 150000003460 sulfonic acids Chemical class 0.000 title description 6
- 150000002460 imidazoles Chemical class 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 35
- -1 chloro, methoxy Chemical group 0.000 claims description 32
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- 229910001868 water Inorganic materials 0.000 claims description 26
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000009385 viral infection Effects 0.000 claims description 6
- 241000700586 Herpesviridae Species 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 229920000858 Cyclodextrin Polymers 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- QUFQITXZAIGEGJ-UHFFFAOYSA-N methanesulfonic acid;1-[1-methyl-2-[4-(5-methylpyridin-2-yl)piperazine-1-carbonyl]imidazol-4-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.N1=CC(C)=CC=C1N1CCN(C(=O)C=2N(C=C(NC(=O)NC=3C=CC(OC(F)(F)F)=CC=3)N=2)C)CC1 QUFQITXZAIGEGJ-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/435—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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (10)
1. Salt af en forbindelse med formlen
hvor R1 betegner methyl, ethyl, butyl eller cyclopropylmethyl, R2 betegner phenyl, hvor phenyl er substitueret med en substituent valgt fra gruppen bestående af trifluormethoxy og difluormethoxy, og R3 betegner hydrogen, methyl, chlor, methoxy eller trifluormethyl, med methansulfonsyre.
2. Saltet ifølge krav 1, kendetegnet ved at det er et dimesylatsalt.
3. Saltet ifølge krav 2 med den følgende formel:
4. Saltet ifølge et hvilket som helst af kravene 1 til 3, kendetegnet ved krystallinsk N-(l-methyl-2-{[4-(5-methylpyridin-2-yl)piperazin-l-yl]-carbonyl}-lH-imidazol-4-yl)-N'-[4-trifluormethoxyphenyl]urea-dimesylat, yderligere kendetegnet ved at røntgenpulverdiffraktogrammet (XRD) viser karakteristiske toppe ved 6,37,11,77, 12,56, 17,17, 18,81, 20,34, 21,47, 23,04, 35,46 grader 2-theta når de optages med et Rigaku MiniFlex røntgenpulverspektrometer (XRD).
5. Saltet ifølge et hvilket som helst af kravene 1 til 4, kendetegnet ved krystallinsk N-(l-methyl-2-{[4-(5-methylpyridin-2-yl)piperazin-l-yl]-carbonyl}-lH-imidazol-4-yl)-N,-(4-trifluormelhoxyphenyl]urea-dimesylat, yderligere kendetegnet ved et røntgenpulverdiffraktogram (XRD) som illustreret i Fig. 1, når de optages med et Rigaku MiniFlex røntgenpulverspektrometer (XRD).
6. Fremgangsmåde til fremstillingen af et salt af forbindelserne med formel (I) ifølge krav 1, hvor der indgår omsætning afen forbindelse med formel (I) med methansulfonsyre.
7. Saltet ifølge et hvilket som helst af kravene 1 til 5 til anvendelse i en fremgangsmåde til behandling og/eller profylakse af sygdomme, især af virusinfektioner, fortrinsvis infektioner med HCMV eller infektioner med en anden repræsentant fra herpes viridae-gruppen.
8. Lægemiddel indeholdende et salt ifølge et hvilket som helst af kravene 1 til 5 i kombination med mindst én inert, ikke-toxisk, farmaceutisk egnet excipiens.
9. Lægemidlet ifølge krav 8, kendetegnet ved at der indgår 5 til 12,5 mg/mL af et salt ifølge et hvilket som helst af kravene 1 til 5, 50 til 150 mg/mL hydroxypropyl-8-cyclodextrin, 0,5 til 2,0 mg/mL natriumacetat og vand, og hvis relevant, yderligere farmaceutisk acceptable excipienser.
10. Lægemidlet ifølge krav 8 eller 9 til anvendelse i en fremgangsmåde til behandling og/eller profylakse af virusinfektioner, fortrinsvis infektioner med HCMV eller infektioner med en anden repræsentant fra herpes viridae-gruppen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201110113749 DE102011113749A1 (de) | 2011-09-14 | 2011-09-14 | Sulfonsäuresalze Heterocyclylamid-substituiertr Imidazole |
| PCT/EP2012/067814 WO2013037812A1 (de) | 2011-09-14 | 2012-09-12 | Sulfonsäuresalze heterocyclylamid-substituierter imidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2755964T3 true DK2755964T3 (da) | 2016-08-29 |
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ID=46888404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12761936.9T DK2755964T3 (da) | 2011-09-14 | 2012-09-12 | Sulfonsyresalte af heterocyclylamid-substituerede imidazoler |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9133165B2 (da) |
| EP (1) | EP2755964B1 (da) |
| JP (1) | JP6193860B2 (da) |
| KR (1) | KR101983416B1 (da) |
| CN (1) | CN103889973B (da) |
| AU (1) | AU2012307449B8 (da) |
| BR (1) | BR112014006196A2 (da) |
| CA (1) | CA2848806C (da) |
| CY (1) | CY1118487T1 (da) |
| DE (1) | DE102011113749A1 (da) |
| DK (1) | DK2755964T3 (da) |
| ES (1) | ES2593268T3 (da) |
| HR (1) | HRP20161186T1 (da) |
| HU (1) | HUE030091T2 (da) |
| IL (1) | IL231546A (da) |
| LT (1) | LT2755964T (da) |
| MX (1) | MX2014002921A (da) |
| PH (1) | PH12014500577A1 (da) |
| PL (1) | PL2755964T3 (da) |
| PT (1) | PT2755964T (da) |
| RS (1) | RS55191B1 (da) |
| RU (1) | RU2606639C2 (da) |
| SG (1) | SG11201400653PA (da) |
| SI (1) | SI2755964T1 (da) |
| SM (1) | SMT201600353B (da) |
| WO (1) | WO2013037812A1 (da) |
| ZA (1) | ZA201401911B (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL264178B2 (en) | 2016-07-14 | 2024-05-01 | Crinetics Pharmaceuticals Inc | Somatostatin modulators and uses thereof |
| AR113206A1 (es) | 2017-01-10 | 2020-02-19 | Bayer Cropscience Ag | Derivados heterocíclicos como pesticidas |
| JP2022540922A (ja) * | 2019-07-17 | 2022-09-20 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターの結晶形態 |
| CA3191084A1 (en) | 2020-09-09 | 2022-03-17 | Gerald Burke | Formulations of a somatostatin modulator |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1062357A (en) * | 1965-03-23 | 1967-03-22 | Pfizer & Co C | Quinazolone derivatives |
| US4337341A (en) * | 1976-11-02 | 1982-06-29 | Eli Lilly And Company | 4a-Aryl-octahydro-1H-2-pyrindines |
| DE69028552T2 (de) * | 1989-12-28 | 1997-03-06 | The Upjohn Co., Kalamazoo, Mich. | Diaromatische substituierte verbindungen gegen den aids-virus |
| DK0755393T3 (da) * | 1994-04-15 | 2001-12-17 | Upjohn Co | Nye krystalformer af 1-[5-methansulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazin |
| WO1997026880A2 (en) * | 1996-01-26 | 1997-07-31 | Pharmacia & Upjohn Company | Use of a combination of delavirdine and one or more protease inhibitors in hiv-1 infected patients |
| FR2842808B1 (fr) * | 2002-07-25 | 2004-09-10 | Sod Conseils Rech Applic | Nouveaux derives d'arylimidazoles, leur preparation et leurs applications therapeutiques |
| DE10257358A1 (de) * | 2002-12-09 | 2004-07-08 | Bayer Healthcare Ag | Substituierte Pyrrole |
| WO2005004763A1 (en) * | 2003-07-01 | 2005-01-20 | Pharmacia & Upjohn Company Llc. | Diffusion layer modulated solids |
| DE102005008183A1 (de) * | 2005-02-23 | 2006-08-31 | Bayer Healthcare Ag | Heterocyclylamid-substituierte Imidazole |
| US8546423B2 (en) * | 2005-05-18 | 2013-10-01 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
| DE102005033103A1 (de) * | 2005-07-15 | 2007-01-25 | Bayer Healthcare Ag | Heterocyclylamid-substituierte Thiazole, Pyrrole und Thiophene |
| KR101449057B1 (ko) * | 2006-03-17 | 2014-10-10 | 암비트 바이오사이언시즈 코포레이션 | 질환 치료용 이미다졸로티아졸 화합물 |
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2011
- 2011-09-14 DE DE201110113749 patent/DE102011113749A1/de not_active Ceased
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- 2012-09-12 AU AU2012307449A patent/AU2012307449B8/en not_active Ceased
- 2012-09-12 BR BR112014006196A patent/BR112014006196A2/pt not_active Application Discontinuation
- 2012-09-12 ES ES12761936.9T patent/ES2593268T3/es active Active
- 2012-09-12 SG SG11201400653PA patent/SG11201400653PA/en unknown
- 2012-09-12 WO PCT/EP2012/067814 patent/WO2013037812A1/de not_active Ceased
- 2012-09-12 HU HUE12761936A patent/HUE030091T2/en unknown
- 2012-09-12 LT LTEP12761936.9T patent/LT2755964T/lt unknown
- 2012-09-12 US US14/344,995 patent/US9133165B2/en not_active Expired - Fee Related
- 2012-09-12 CA CA2848806A patent/CA2848806C/en not_active Expired - Fee Related
- 2012-09-12 MX MX2014002921A patent/MX2014002921A/es unknown
- 2012-09-12 EP EP12761936.9A patent/EP2755964B1/de active Active
- 2012-09-12 PH PH1/2014/500577A patent/PH12014500577A1/en unknown
- 2012-09-12 RU RU2014114381A patent/RU2606639C2/ru active
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- 2012-09-12 HR HRP20161186TT patent/HRP20161186T1/hr unknown
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- 2012-09-12 CN CN201280052142.1A patent/CN103889973B/zh not_active Expired - Fee Related
- 2012-09-12 SI SI201230712A patent/SI2755964T1/sl unknown
- 2012-09-12 PT PT127619369T patent/PT2755964T/pt unknown
- 2012-09-12 KR KR1020147009444A patent/KR101983416B1/ko not_active Expired - Fee Related
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