LV12957B - Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-3-(1-methylethylamino)-2-pyridinyl]piperazine - Google Patents
Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-3-(1-methylethylamino)-2-pyridinyl]piperazine Download PDFInfo
- Publication number
- LV12957B LV12957B LVP-02-186A LV020186A LV12957B LV 12957 B LV12957 B LV 12957B LV 020186 A LV020186 A LV 020186A LV 12957 B LV12957 B LV 12957B
- Authority
- LV
- Latvia
- Prior art keywords
- carbonyl
- methylethylamino
- pyridinyl
- methanesulfonamidoindolyl
- piperazine
- Prior art date
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 67
- 239000013078 crystal Substances 0.000 title abstract description 32
- 238000001228 spectrum Methods 0.000 claims abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 4
- 241000272525 Anas platyrhynchos Species 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 229960005141 piperazine Drugs 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- ZKJKXGCLZUMGNT-UHFFFAOYSA-N methanesulfonic acid;piperazine Chemical compound CS(O)(=O)=O.C1CNCCN1 ZKJKXGCLZUMGNT-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 241001430294 unidentified retrovirus Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 (1-methylethylamino)- Chemical class 0.000 description 1
- MIKRTHXMXJQUBV-UHFFFAOYSA-N CS(=O)(=O)O.CC(C)NC=1C(=NC=CC1)N1CCNCC1 Chemical compound CS(=O)(=O)O.CC(C)NC=1C(=NC=CC1)N1CCNCC1 MIKRTHXMXJQUBV-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010020144 Histoplasmosis disseminated Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 229960001520 ranitidine hydrochloride Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (1)
- IZGUDROJUMA FORMULA 1-[5-metānsulfonamidoindolil-2-karbonil]-4-[3-(1-metiletilamino)-2-piri-dinil]piperazīna monometānsulfonāta sāls, kas zināms kā “S” forma, ar sekojošu pulvera rentgenstaru difrakcijas spektru: 2 tēta leņķis (°) Starpplakņu attālums (A) Relatīvā intensitāte (%) 27,10 3,288 20,1 24,55 3,623 28,0 23,40 3,799 28,6 23,10 3,847 36,8 22,25 3,992 100,0 21,55 4,120 64,9 20,75 4,277 34,3 19,30 4,595 69,1 18,25 4,857 28,9 17,40 5,093 15,4 17,10 5,181 52,5 14,55 6,083 22,4 13,55 6,530 30,3 13,05 6,779 14,8 6,40 13,799 56,2 kur 2 tēta leņķis ir mērīts grādos, starpplakņu attālums ir mērīts angstrēmos un kur relatīvā intensitāte ir katra maksimuma intensitātes procentuālā attiecība pret lielāko maksimumu 22,25 grādos. 1-[5-metānsulfonamidoindolil-2-karbonil]-4-[3-(1-metiletilamino)-2-piri-diniljpiperazīna monometānsulfonāta sāls, kas zināms kā “T” forma, ar sekojošu pulvera rentgenstaru difrakcijas spektru: 2 2 tēta leņķis (°) Starpplakņu attālums (A) Relatīvā intensitāte (%) 28,80 3,097 19,9 27,90 3,195 18,5 27,10 3,288 28,3 25,00 3,559 21,5 23,10 3,847 64,6 22,75 3,906 22,6 21,95 4,046 39,6 20,40 4,350 82,7 18,75 4,729 60,2 18,40 4,818 100,0 13,35 6,627 46,4 12,35 7,161 26,6 9,70 9,111 23,8 6,65 13,281 59,5 kur 2 tēta leņķis ir mērīts grādos, starpplakņu attālums ir mērīts angstrēmos un kur relatīvā intensitāte ir katra maksimuma intensitātes procentuālā attiecība pret lielāko maksimumu 18,40 grādos.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22786094A | 1994-04-15 | 1994-04-15 | |
US31178094A | 1994-09-23 | 1994-09-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
LV12957B true LV12957B (en) | 2003-04-20 |
Family
ID=26921831
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-02-186A LV12957B (en) | 1994-04-15 | 2002-10-24 | Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-3-(1-methylethylamino)-2-pyridinyl]piperazine |
Country Status (26)
Country | Link |
---|---|
US (1) | US6452007B1 (lv) |
EP (1) | EP0755393B1 (lv) |
JP (1) | JP3817261B2 (lv) |
KR (1) | KR100364941B1 (lv) |
CN (1) | CN1147253A (lv) |
AT (1) | ATE207481T1 (lv) |
AU (1) | AU693939B2 (lv) |
CA (1) | CA2184598C (lv) |
CZ (1) | CZ287164B6 (lv) |
DE (1) | DE69523447T2 (lv) |
DK (1) | DK0755393T3 (lv) |
ES (1) | ES2164147T3 (lv) |
FI (1) | FI111364B (lv) |
HU (1) | HU226827B1 (lv) |
IL (1) | IL113162A (lv) |
LV (1) | LV12957B (lv) |
MX (1) | MX9604831A (lv) |
MY (1) | MY116830A (lv) |
NO (1) | NO310024B1 (lv) |
NZ (1) | NZ282211A (lv) |
PL (1) | PL180776B1 (lv) |
PT (1) | PT755393E (lv) |
RU (1) | RU2136677C1 (lv) |
SK (1) | SK282424B6 (lv) |
TW (1) | TW393478B (lv) |
WO (1) | WO1995028398A1 (lv) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1083885B1 (en) | 1998-06-11 | 2006-12-27 | Pharmacia & Upjohn Company LLC | Delavirdine tablet formulation |
US6872811B1 (en) | 1998-09-30 | 2005-03-29 | Millennium Pharmaceuticals, Inc. | HRPCa9 and HRPCa10 nucleic acids and polypeptides |
DE102011113749A1 (de) * | 2011-09-14 | 2013-03-14 | Aicuris Gmbh & Co. Kg | Sulfonsäuresalze Heterocyclylamid-substituiertr Imidazole |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3565924A (en) | 1968-07-01 | 1971-02-23 | Wisconsin Alumni Res Found | 25-hydroxycholfcalciferol |
US3833622A (en) | 1969-03-17 | 1974-09-03 | Upjohn Co | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
GB1532682A (en) | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
IL63968A (en) | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
DK0507861T3 (lv) * | 1989-12-28 | 1997-03-03 | Upjohn Co | |
US5563142A (en) * | 1989-12-28 | 1996-10-08 | The Upjohn Company | Diaromatic substituted compounds as anti-HIV-1 agents |
US5599930A (en) * | 1991-07-03 | 1997-02-04 | The Upjohn Company | Substituted indoles as anti-AIDS pharmaceuticals |
-
1995
- 1995-03-01 WO PCT/US1995/002166 patent/WO1995028398A1/en active IP Right Grant
- 1995-03-01 HU HU9602857A patent/HU226827B1/hu unknown
- 1995-03-01 MX MX9604831A patent/MX9604831A/es unknown
- 1995-03-01 AU AU35136/95A patent/AU693939B2/en not_active Expired
- 1995-03-01 AT AT95911842T patent/ATE207481T1/de active
- 1995-03-01 US US08/732,254 patent/US6452007B1/en not_active Expired - Lifetime
- 1995-03-01 ES ES95911842T patent/ES2164147T3/es not_active Expired - Lifetime
- 1995-03-01 SK SK1229-96A patent/SK282424B6/sk unknown
- 1995-03-01 NZ NZ282211A patent/NZ282211A/en not_active IP Right Cessation
- 1995-03-01 PT PT95911842T patent/PT755393E/pt unknown
- 1995-03-01 CZ CZ19962942A patent/CZ287164B6/cs not_active IP Right Cessation
- 1995-03-01 EP EP95911842A patent/EP0755393B1/en not_active Expired - Lifetime
- 1995-03-01 RU RU96119978A patent/RU2136677C1/ru active
- 1995-03-01 PL PL95316688A patent/PL180776B1/pl unknown
- 1995-03-01 CA CA002184598A patent/CA2184598C/en not_active Expired - Lifetime
- 1995-03-01 JP JP52695295A patent/JP3817261B2/ja not_active Expired - Lifetime
- 1995-03-01 CN CN95192523A patent/CN1147253A/zh active Pending
- 1995-03-01 DK DK95911842T patent/DK0755393T3/da active
- 1995-03-01 DE DE69523447T patent/DE69523447T2/de not_active Expired - Lifetime
- 1995-03-01 KR KR1019960705760A patent/KR100364941B1/ko not_active IP Right Cessation
- 1995-03-17 TW TW084102592A patent/TW393478B/zh not_active IP Right Cessation
- 1995-03-28 IL IL11316295A patent/IL113162A/xx not_active IP Right Cessation
- 1995-03-28 MY MYPI95000766A patent/MY116830A/en unknown
-
1996
- 1996-10-14 FI FI964114A patent/FI111364B/fi not_active IP Right Cessation
- 1996-10-15 NO NO964386A patent/NO310024B1/no not_active IP Right Cessation
-
2002
- 2002-10-24 LV LVP-02-186A patent/LV12957B/en unknown
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