HRP20100631T1 - Kristal indola koji sadrži sulfonamid i postupak njegove proizvodnje - Google Patents
Kristal indola koji sadrži sulfonamid i postupak njegove proizvodnje Download PDFInfo
- Publication number
- HRP20100631T1 HRP20100631T1 HR20100631T HRP20100631T HRP20100631T1 HR P20100631 T1 HRP20100631 T1 HR P20100631T1 HR 20100631 T HR20100631 T HR 20100631T HR P20100631 T HRP20100631 T HR P20100631T HR P20100631 T1 HRP20100631 T1 HR P20100631T1
- Authority
- HR
- Croatia
- Prior art keywords
- indol
- cyano
- methyl
- sulfonamide
- crystalline form
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- 239000013078 crystal Substances 0.000 title claims 5
- -1 indole compound Chemical class 0.000 title claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 229940124530 sulfonamide Drugs 0.000 title 1
- 150000003456 sulfonamides Chemical class 0.000 title 1
- LWGUASZLXHYWIV-UHFFFAOYSA-N 3-cyano-n-(3-cyano-4-methyl-1h-indol-7-yl)benzenesulfonamide Chemical compound C1=2NC=C(C#N)C=2C(C)=CC=C1NS(=O)(=O)C1=CC=CC(C#N)=C1 LWGUASZLXHYWIV-UHFFFAOYSA-N 0.000 claims abstract 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000012046 mixed solvent Substances 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 5
- 238000010521 absorption reaction Methods 0.000 claims 4
- 238000000862 absorption spectrum Methods 0.000 claims 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Kristalni oblik (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida, naznačen time, da je njegov difrakcijski maksimum na kutu difrakcije (2θ ± 0.2°) od 11,4° u rentgenskoj difrakciji praška. Patent sadrži još 22 patentna zahtjeva.
Claims (23)
1. Kristalni oblik (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida, naznačen time, da je njegov difrakcijski maksimum na kutu difrakcije (2θ ± 0.2°) od 11,4° u rentgenskoj difrakciji praška.
2. Kristalni oblik (Oblik C) u skladu s patentnim zahtjevom 1, naznačen time, da je osim toga njegov difrakcijski maksimum na kutu difrakcije (2θ ± 0.2°) od 19,1° u rentgenskoj difrakciji praška.
3. Kristalni oblik (Oblik C) u skladu s bilo kojim patentnim zahtjevom 1 do 2, naznačen time, da mu je apsorpcijski maksimum na valnom broju 1410 ± 1 cm-1 u infracrvenom apsorpcijskom spektru (KBr).
4. Kristalni oblik (Oblik C) u skladu s patentnim zahtjevom 3, naznačen time, da je osim toga njegov apsorpcijski maksimum na valnom broju 1443 ± 1 cm-1 u infracrvenom apsorpcijskom spektru (KBr).
5. Kristalni oblik (Oblik C) u skladu s bilo kojim patentnim zahtjevom 1 do 2, naznačen time, da je njegov maksimum u kemijskom pomaku otprilike 143.4 ppm u 13C NMR spektru u krutom stanju.
6. Kristalni oblik (Oblik C) u skladu s patentnim zahtjevom 5, naznačen time, da je osim toga njegov maksimum u kemijskom pomaku otprilike 131.1 ppm u 13C NMR spektru u krutom stanju.
7. Postupak za pripravu kristalnog oblika (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 6, naznačen time, da se N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid kristalizira pomoću jednostavnog otapala odabranog iz skupine koju čine N-propil alkohol, izopropil alkohol, n-butil alkohol, s-butil alkohol, t-butil alkohol i voda ili pomoću njihove mješavine kao kristalizacijskog otapala.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da je kristalizacijsko otapalo jednostavno otapalo od izopropil alkohola ili s-butil alkohola, ili miješano otapalo s-butil alkohola i vode ili miješano otapalo izopropil alkohola i vode.
9. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da je kristalizacijsko otapalo miješano otapalo s-butil alkohola i vode (omjer volumena = 3:1-5:1) ili miješano otapalo izopropil alkohola i vode (omjer volumena = 9:1-10:1).
10. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da je kristalizacijsko otapalo miješano otapalo s-butil alkohola i vode (omjer volumena = 3.9:1-4.1:1).
11. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da se N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid zagrijava i otapa u otapalu i zatim kristalizira.
12. Postupak u skladu s patentnim zahtjevom 7, naznačen time, da se N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid zagrijava i otapa u otapalu i zatim kristalizira postupnim hlađenjem.
13. Postupak za pripravu kristalnog oblika (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 6, naznačen time, da se N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid zagrijava na 80-130°C.
14. Postupak za pripravu kristalnog oblika (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 6, naznačen time, da se N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid zagrijava i miješa u vodi na 60-90°C.
15. Postupak za pripravu kristalnog oblika (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 6, naznačen time, da se kristalni oblik spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid hidrata zagrijava na 80-130°C.
16. Postupak za pripravu kristalnog oblika (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida u skladu s bilo kojim patentnim zahtjevom 1 do 6, naznačen time, da se kristalni oblik spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid hidrata zagrijava i miješa u vodi na 60-90 °C.
17. Kristalni oblik (Oblik A) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid hidrata, naznačen time, da je njegov difrakcijski maksimum na kutu difrakcije (2θ ± 0.2°) od 8,5° u rentgenskoj difrakciji praška.
18. Kristalni oblik (Oblik A) u skladu s patentnim zahtjevom 17, naznačen time, da je osim toga njegov difrakcijski maksimum na kutu difrakcije (2θ ± 0.2°) od 25,8° u rentgenskoj difrakciji praška.
19. Kristalni oblik (Oblik A) u skladu s patentnim zahtjevom 17 ili 18, naznačen time, da mu je apsorpcijski maksimum na valnom broju 616 ± 1 cm-1 u infracrvenom apsorpcijskom spektru (KBr).
20. Kristalni oblik (Oblik A) u skladu s patentnim zahtjevom 19, naznačen time, da je osim toga njegov apsorpcijski maksimum na valnom broju 802 ± 1 cm-1 u infracrvenom apsorpcijskom spektru (KBr).
21. Kristalni oblik (Oblik A) u skladu s patentnim zahtjevom 17 ili 18, naznačen time, da je njegov maksimum u kemijskom pomaku otprilike 134.7 ppm u 13C NMR spektru u krutom stanju.
22. Kristalni oblik (Oblik A) u skladu s patentnim zahtjevom 21, naznačen time, da je osim toga njegov maksimum u kemijskom pomaku otprilike 126.3 ppm u 13C NMR spektru u krutom stanju.
23. Postupak za pripravu kristalnog oblika (Oblik A) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamid hidrata u skladu s bilo kojim patentnim zahtjevom 17 do 22, naznačen time, da se kristalni oblik (Oblik C) spoja N-(3-cijano-4-metil-1H-indol-7-il)-3-cijanobenzen-sulfonamida rekristalizira iz miješanog otapala etanola i vode.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003318953 | 2003-09-10 | ||
| PCT/JP2004/012649 WO2005026118A1 (ja) | 2003-09-10 | 2004-09-01 | スルホンアミド含有インドール化合物の結晶およびその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100631T1 true HRP20100631T1 (hr) | 2010-12-31 |
Family
ID=34308544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100631T HRP20100631T1 (hr) | 2003-09-10 | 2010-11-22 | Kristal indola koji sadrži sulfonamid i postupak njegove proizvodnje |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US7754894B2 (hr) |
| EP (1) | EP1666463B1 (hr) |
| JP (1) | JP4435090B2 (hr) |
| KR (1) | KR20060120644A (hr) |
| CN (2) | CN101165049A (hr) |
| AT (1) | ATE486849T1 (hr) |
| AU (1) | AU2004272400B2 (hr) |
| BR (1) | BRPI0414314A (hr) |
| CA (1) | CA2536995C (hr) |
| CY (1) | CY1110975T1 (hr) |
| DE (1) | DE602004029907D1 (hr) |
| DK (1) | DK1666463T3 (hr) |
| ES (1) | ES2354286T3 (hr) |
| HK (1) | HK1092796A1 (hr) |
| HR (1) | HRP20100631T1 (hr) |
| IL (2) | IL174059A0 (hr) |
| MX (1) | MXPA06002732A (hr) |
| NO (1) | NO335256B1 (hr) |
| NZ (1) | NZ546111A (hr) |
| PL (1) | PL1666463T3 (hr) |
| PT (1) | PT1666463E (hr) |
| RU (1) | RU2336269C2 (hr) |
| SI (1) | SI1666463T1 (hr) |
| TW (1) | TW200514770A (hr) |
| WO (1) | WO2005026118A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004029907D1 (de) * | 2003-09-10 | 2010-12-16 | Eisai R&D Man Co Ltd | Kristall einer sulfonamidhaltigen indolverbindung und verfahren zu dessen herstellung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3868534B2 (ja) * | 1996-05-24 | 2007-01-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スルホンアミド誘導体の製造法および中間体 |
| JP2000247949A (ja) * | 1999-02-26 | 2000-09-12 | Eisai Co Ltd | スルホンアミド含有インドール化合物 |
| ATE464892T1 (de) * | 2000-02-03 | 2010-05-15 | Eisai R&D Man Co Ltd | Inhibitoren der integrinexpression |
| TWI283575B (en) * | 2000-10-31 | 2007-07-11 | Eisai Co Ltd | Medicinal compositions for concomitant use as anticancer agent |
| DE602004029907D1 (de) * | 2003-09-10 | 2010-12-16 | Eisai R&D Man Co Ltd | Kristall einer sulfonamidhaltigen indolverbindung und verfahren zu dessen herstellung |
-
2004
- 2004-09-01 DE DE602004029907T patent/DE602004029907D1/de not_active Expired - Lifetime
- 2004-09-01 BR BRPI0414314-0A patent/BRPI0414314A/pt not_active IP Right Cessation
- 2004-09-01 ES ES04772605T patent/ES2354286T3/es not_active Expired - Lifetime
- 2004-09-01 MX MXPA06002732A patent/MXPA06002732A/es active IP Right Grant
- 2004-09-01 AT AT04772605T patent/ATE486849T1/de active
- 2004-09-01 CN CNA2007101667949A patent/CN101165049A/zh active Pending
- 2004-09-01 CN CNB2004800260696A patent/CN100406440C/zh not_active Expired - Fee Related
- 2004-09-01 JP JP2005513843A patent/JP4435090B2/ja not_active Expired - Fee Related
- 2004-09-01 AU AU2004272400A patent/AU2004272400B2/en not_active Ceased
- 2004-09-01 DK DK04772605.4T patent/DK1666463T3/da active
- 2004-09-01 PL PL04772605T patent/PL1666463T3/pl unknown
- 2004-09-01 WO PCT/JP2004/012649 patent/WO2005026118A1/ja active Application Filing
- 2004-09-01 US US10/571,279 patent/US7754894B2/en active Active
- 2004-09-01 EP EP04772605A patent/EP1666463B1/en not_active Expired - Lifetime
- 2004-09-01 PT PT04772605T patent/PT1666463E/pt unknown
- 2004-09-01 RU RU2006111454/04A patent/RU2336269C2/ru not_active IP Right Cessation
- 2004-09-01 CA CA2536995A patent/CA2536995C/en not_active Expired - Fee Related
- 2004-09-01 SI SI200431578T patent/SI1666463T1/sl unknown
- 2004-09-01 NZ NZ546111A patent/NZ546111A/en not_active IP Right Cessation
- 2004-09-01 KR KR1020067004877A patent/KR20060120644A/ko active Search and Examination
- 2004-09-06 TW TW093126889A patent/TW200514770A/zh not_active IP Right Cessation
-
2006
- 2006-03-02 IL IL174059A patent/IL174059A0/en not_active IP Right Cessation
- 2006-04-05 NO NO20061545A patent/NO335256B1/no not_active IP Right Cessation
- 2006-12-06 HK HK06113378.9A patent/HK1092796A1/xx not_active IP Right Cessation
-
2009
- 2009-01-18 IL IL196569A patent/IL196569A0/en unknown
- 2009-06-09 US US12/480,959 patent/US20090247768A1/en not_active Abandoned
-
2010
- 2010-11-22 HR HR20100631T patent/HRP20100631T1/hr unknown
- 2010-12-10 CY CY20101101136T patent/CY1110975T1/el unknown
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