NO310024B1 - Nye krystallformer av 1-[5-metansulfonamidoindolyl-2- karbonyl]-4-[3-(1-metyletylamino)-2- pyridinyl]piperazinmonometansulfonatsalt - Google Patents

Nye krystallformer av 1-[5-metansulfonamidoindolyl-2- karbonyl]-4-[3-(1-metyletylamino)-2- pyridinyl]piperazinmonometansulfonatsalt Download PDF

Info

Publication number: NO310024B1
Authority: NO; Norway
Prior art keywords: carbonyl; methanesulfonamidoindolyl; methylethylamino; pyridinyl; piperazine
Prior art date: 1994-04-15

Application number

NO964386A

Other languages

English (en)

Norwegian (no)

Other versions

NO964386D0 (no

NO964386L (no

Inventor

Jeffrey L Havens

Donald P Smith

Michael S Bergren

Mark A Lyster

Original Assignee

Upjohn Co

Priority date (The priority date 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 date listed.)

1994-04-15

Filing date

1996-10-15

Publication date

2001-05-07

1996-10-15 Application filed by Upjohn Co filed Critical Upjohn Co

1996-10-15 Publication of NO964386D0 publication Critical patent/NO964386D0/no

1996-10-15 Publication of NO964386L publication Critical patent/NO964386L/no

2001-05-07 Publication of NO310024B1 publication Critical patent/NO310024B1/no

Links

239000013078 crystal Substances 0.000 title description 49
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 25
238000000634 powder X-ray diffraction Methods 0.000 claims description 3
238000001228 spectrum Methods 0.000 claims description 3
238000002083 X-ray spectrum Methods 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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
239000002904 solvent Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
150000001875 compounds Chemical class 0.000 description 12
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
239000002002 slurry Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000012458 free base Substances 0.000 description 8
ZKJKXGCLZUMGNT-UHFFFAOYSA-N methanesulfonic acid;piperazine Chemical compound CS(O)(=O)=O.C1CNCCN1 ZKJKXGCLZUMGNT-UHFFFAOYSA-N 0.000 description 8
239000003814 drug Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
229940079593 drug Drugs 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
239000012453 solvate Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
238000009835 boiling Methods 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
206010001513 AIDS related complex Diseases 0.000 description 2
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
238000010521 absorption reaction Methods 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000036765 blood level Effects 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
238000002483 medication Methods 0.000 description 2
239000000825 pharmaceutical preparation Substances 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
238000003756 stirring Methods 0.000 description 2
-1 3-( 1- methylethylamino)-2- pyridinyl Chemical group 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
206010007134 Candida infections Diseases 0.000 description 1
206010020144 Histoplasmosis disseminated Diseases 0.000 description 1
241000282412 Homo Species 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
208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
241000700605 Viruses Species 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
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
238000011021 bench scale process Methods 0.000 description 1
201000003984 candidiasis Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
210000004698 lymphocyte Anatomy 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
230000001766 physiological effect Effects 0.000 description 1
POPKUFIVYZJEDK-UHFFFAOYSA-N piperazin-1-ylmethanesulfonic acid Chemical class OS(=O)(=O)CN1CCNCC1 POPKUFIVYZJEDK-UHFFFAOYSA-N 0.000 description 1
201000000317 pneumocystosis Diseases 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
230000003612 virological effect Effects 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)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Immunology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Indole Compounds (AREA)

NO964386A 1994-04-15 1996-10-15 Nye krystallformer av 1-[5-metansulfonamidoindolyl-2- karbonyl]-4-[3-(1-metyletylamino)-2- pyridinyl]piperazinmonometansulfonatsalt NO310024B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US22786094A	1994-04-15	1994-04-15
US31178094A	1994-09-23	1994-09-23
PCT/US1995/002166 WO1995028398A1 (en)	1994-04-15	1995-03-01	Novel crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine

Publications (3)

Publication Number	Publication Date
NO964386D0 NO964386D0 (no)	1996-10-15
NO964386L NO964386L (no)	1996-10-15
NO310024B1 true NO310024B1 (no)	2001-05-07

Family

ID=26921831

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO964386A NO310024B1 (no)	1994-04-15	1996-10-15	Nye krystallformer av 1-[5-metansulfonamidoindolyl-2- karbonyl]-4-[3-(1-metyletylamino)-2- pyridinyl]piperazinmonometansulfonatsalt

Country Status (26)

Country	Link
US (1)	US6452007B1 (de)
EP (1)	EP0755393B1 (de)
JP (1)	JP3817261B2 (de)
KR (1)	KR100364941B1 (de)
CN (1)	CN1147253A (de)
AT (1)	ATE207481T1 (de)
AU (1)	AU693939B2 (de)
CA (1)	CA2184598C (de)
CZ (1)	CZ287164B6 (de)
DE (1)	DE69523447T2 (de)
DK (1)	DK0755393T3 (de)
ES (1)	ES2164147T3 (de)
FI (1)	FI111364B (de)
HU (1)	HU226827B1 (de)
IL (1)	IL113162A (de)
LV (1)	LV12957B (de)
MX (1)	MX9604831A (de)
MY (1)	MY116830A (de)
NO (1)	NO310024B1 (de)
NZ (1)	NZ282211A (de)
PL (1)	PL180776B1 (de)
PT (1)	PT755393E (de)
RU (1)	RU2136677C1 (de)
SK (1)	SK282424B6 (de)
TW (1)	TW393478B (de)
WO (1)	WO1995028398A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE349203T1 (de)	1998-06-11	2007-01-15	Pharmacia & Upjohn Co Llc	Delavirdin tablettenformulierung
US6872811B1 (en)	1998-09-30	2005-03-29	Millennium Pharmaceuticals, Inc.	HRPCa9 and HRPCa10 nucleic acids and polypeptides
GB0219660D0 (en) *	2002-08-23	2002-10-02	Astrazeneca Ab	Therapeutic use
DE102011113749A1 (de) *	2011-09-14	2013-03-14	Aicuris Gmbh & Co. Kg	Sulfonsäuresalze Heterocyclylamid-substituiertr Imidazole

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
MX9203454A (es) *	1989-12-28	1992-08-01	Upjohn Co	Compuestos anti sida diaromaticos substituidos.
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 DE DE69523447T patent/DE69523447T2/de not_active Expired - Lifetime
- 1995-03-01 CA CA002184598A patent/CA2184598C/en not_active Expired - Lifetime
- 1995-03-01 AT AT95911842T patent/ATE207481T1/de active
- 1995-03-01 DK DK95911842T patent/DK0755393T3/da active
- 1995-03-01 CN CN95192523A patent/CN1147253A/zh active Pending
- 1995-03-01 EP EP95911842A patent/EP0755393B1/de not_active Expired - Lifetime
- 1995-03-01 ES ES95911842T patent/ES2164147T3/es 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 WO PCT/US1995/002166 patent/WO1995028398A1/en not_active Ceased
- 1995-03-01 SK SK1229-96A patent/SK282424B6/sk unknown
- 1995-03-01 MX MX9604831A patent/MX9604831A/es unknown
- 1995-03-01 CZ CZ19962942A patent/CZ287164B6/cs not_active IP Right Cessation
- 1995-03-01 US US08/732,254 patent/US6452007B1/en not_active Expired - Lifetime
- 1995-03-01 PT PT95911842T patent/PT755393E/pt unknown
- 1995-03-01 KR KR1019960705760A patent/KR100364941B1/ko not_active Expired - Lifetime
- 1995-03-01 JP JP52695295A patent/JP3817261B2/ja not_active Expired - Lifetime
- 1995-03-01 NZ NZ282211A patent/NZ282211A/en not_active IP Right Cessation
- 1995-03-01 HU HU9602857A patent/HU226827B1/hu unknown
- 1995-03-01 AU AU35136/95A patent/AU693939B2/en not_active Expired
- 1995-03-17 TW TW084102592A patent/TW393478B/zh not_active IP Right Cessation
- 1995-03-28 MY MYPI95000766A patent/MY116830A/en unknown
- 1995-03-28 IL IL11316295A patent/IL113162A/xx not_active IP Right Cessation
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

Also Published As

Publication number	Publication date
ES2164147T3 (es)	2002-02-16
JP3817261B2 (ja)	2006-09-06
FI964114A0 (fi)	1996-10-14
SK282424B6 (sk)	2002-01-07
US6452007B1 (en)	2002-09-17
EP0755393B1 (de)	2001-10-24
ATE207481T1 (de)	2001-11-15
EP0755393A1 (de)	1997-01-29
LV12957B (en)	2003-04-20
NO964386D0 (no)	1996-10-15
HUT76467A (en)	1997-09-29
CZ287164B6 (en)	2000-10-11
PT755393E (pt)	2002-04-29
MY116830A (en)	2004-04-30
AU693939B2 (en)	1998-07-09
IL113162A (en)	1999-04-11
FI111364B (fi)	2003-07-15
PL180776B1 (pl)	2001-04-30
PL316688A1 (en)	1997-02-03
CN1147253A (zh)	1997-04-09
DK0755393T3 (da)	2001-12-17
RU2136677C1 (ru)	1999-09-10
FI964114L (fi)	1996-10-14
KR100364941B1 (ko)	2003-02-19
NZ282211A (en)	1997-10-24
SK122996A3 (en)	1997-05-07
JPH09512007A (ja)	1997-12-02
DE69523447T2 (de)	2002-05-16
CA2184598C (en)	2005-05-03
MX9604831A (es)	1998-05-31
AU3513695A (en)	1995-11-10
WO1995028398A1 (en)	1995-10-26
NO964386L (no)	1996-10-15
CZ294296A3 (en)	1997-01-15
IL113162A0 (en)	1995-06-29
DE69523447D1 (de)	2001-11-29
CA2184598A1 (en)	1995-10-26
HU226827B1 (en)	2009-11-30
TW393478B (en)	2000-06-11
HU9602857D0 (en)	1996-12-30
KR970702275A (ko)	1997-05-13

Legal Events

Date	Code	Title	Description
2015-03-09	MK1K	Patent expired

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