NO320128B1 - Fremgangsmate for krystallisering av en revers transkriptaseinhibitor ved anvendelse av et anti-losningsmiddel - Google Patents

Fremgangsmate for krystallisering av en revers transkriptaseinhibitor ved anvendelse av et anti-losningsmiddel Download PDF

Info

Publication number: NO320128B1
Authority: NO; Norway
Prior art keywords: solvent; compound; water; slurry; propanol
Prior art date: 1997-02-05

Application number

NO19993779A

Other languages

English (en)

Norwegian (no)

Other versions

NO993779D0 (no

NO993779L (no

Inventor

William Clarke

Louis S Crocker

Ii Joseph L Kukura

Original Assignee

Merck & Co Inc

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.)

1997-02-05

Filing date

1999-08-04

Publication date

2005-10-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27451618&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO320128(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-03-24 Priority claimed from GBGB9706046.1A external-priority patent/GB9706046D0/en

1997-05-07 Priority claimed from GBGB9709348.8A external-priority patent/GB9709348D0/en

1999-08-04 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1999-08-04 Publication of NO993779D0 publication Critical patent/NO993779D0/no

1999-10-05 Publication of NO993779L publication Critical patent/NO993779L/no

2005-10-31 Publication of NO320128B1 publication Critical patent/NO320128B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 52
239000012296 anti-solvent Substances 0.000 title claims abstract description 46
239000003419 rna directed dna polymerase inhibitor Substances 0.000 title description 3
239000002904 solvent Substances 0.000 claims abstract description 86
238000002425 crystallisation Methods 0.000 claims abstract description 33
XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims abstract description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 78
239000002002 slurry Substances 0.000 claims description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
150000001875 compounds Chemical class 0.000 claims description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
230000008025 crystallization Effects 0.000 claims description 30
239000000463 material Substances 0.000 claims description 27
238000001035 drying Methods 0.000 claims description 14
238000000634 powder X-ray diffraction Methods 0.000 claims description 13
239000006228 supernatant Substances 0.000 claims description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
238000001914 filtration Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
238000000227 grinding Methods 0.000 claims description 7
238000002156 mixing Methods 0.000 claims description 6
230000004580 weight loss Effects 0.000 claims description 6
238000002411 thermogravimetry Methods 0.000 claims description 4
238000005406 washing Methods 0.000 claims description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 3
238000001938 differential scanning calorimetry curve Methods 0.000 claims description 3
238000003801 milling Methods 0.000 claims description 2
239000013618 particulate matter Substances 0.000 claims description 2
238000010583 slow cooling Methods 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims 2
239000011877 solvent mixture Substances 0.000 claims 1
239000013078 crystal Substances 0.000 description 30
239000000047 product Substances 0.000 description 15
239000012467 final product Substances 0.000 description 5
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 3
238000005185 salting out Methods 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000010586 diagram Methods 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000001654 germ layer Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PUYCICVJCRLABY-UHFFFAOYSA-N heptane;oxolane Chemical compound C1CCOC1.CCCCCCC PUYCICVJCRLABY-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000006911 nucleation Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000003134 recirculating effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Virology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Enzymes And Modification Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

NO19993779A 1997-02-05 1999-08-04 Fremgangsmate for krystallisering av en revers transkriptaseinhibitor ved anvendelse av et anti-losningsmiddel NO320128B1 (no)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US3738597P	1997-02-05	1997-02-05
GBGB9706046.1A GB9706046D0 (en)	1997-03-24	1997-03-24	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
US4280797P	1997-04-08	1997-04-08
GBGB9709348.8A GB9709348D0 (en)	1997-05-07	1997-05-07	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
PCT/US1998/001999 WO1998033782A1 (en)	1997-02-05	1998-02-02	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent

Publications (3)

Publication Number	Publication Date
NO993779D0 NO993779D0 (no)	1999-08-04
NO993779L NO993779L (no)	1999-10-05
NO320128B1 true NO320128B1 (no)	2005-10-31

Family

ID=27451618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19993779A NO320128B1 (no)	1997-02-05	1999-08-04	Fremgangsmate for krystallisering av en revers transkriptaseinhibitor ved anvendelse av et anti-losningsmiddel

Country Status (18)

Country	Link
EP (1)	EP0975609B1 (ru)
JP (6)	JP3418626B2 (ru)
KR (1)	KR100573192B1 (ru)
CN (2)	CN1191242C (ru)
AT (1)	ATE486065T1 (ru)
AU (1)	AU738545C (ru)
CA (1)	CA2279198C (ru)
CZ (2)	CZ297535B6 (ru)
DE (1)	DE69841972D1 (ru)
EA (1)	EA001805B1 (ru)
EE (1)	EE03827B1 (ru)
HU (1)	HU229087B1 (ru)
IL (1)	IL130715A (ru)
NO (1)	NO320128B1 (ru)
NZ (1)	NZ336510A (ru)
PL (1)	PL197740B1 (ru)
SK (1)	SK284935B6 (ru)
WO (1)	WO1998033782A1 (ru)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998033782A1 (en) *	1997-02-05	1998-08-06	Merck & Co., Inc.	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
US6015926A (en) *	1997-05-16	2000-01-18	Merck & Co., Inc.	Efficient enantioselective addition reaction using an organozinc reagent
US20010014352A1 (en)	1998-05-27	2001-08-16	Udit Batra	Compressed tablet formulation
HRP990182A2 (en) *	1998-06-11	2000-02-29	Du Pont Pharm Co	Crystalline efavirenz
GB9828721D0 (en) *	1998-12-24	1999-02-17	Glaxo Group Ltd	Novel apparatus and process
WO2006018853A2 (en)	2004-08-19	2006-02-23	Hetero Drugs Limited	Novel polymorphs of efavirenz
WO2008108630A1 (en) *	2007-03-02	2008-09-12	Ultimorphix Technologies B.V.	Polymorphic forms of efavirenz
WO2009087679A2 (en) *	2007-12-24	2009-07-16	Matrix Laboratories Limited	Process for preparing polymorphic forms of (s)-6-chloro-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
ES2445090T3 (es)	2008-12-22	2014-02-28	Hetero Research Foundation	Procedimiento para preparar un polimorfo de efavirenz
DE102009041443A1 (de)	2009-09-16	2011-03-31	Archimica Gmbh	Salze des 6-Chlor-4-(cyclopropylethinyl)-1,4-dihydro-4-(trifluormethyl)-2H-3,1-benzoxazin-2-ons und deren Synthese, Aufreinigung und Anwendung als Vorstufen für Efavirenz
EP2471783A1 (en)	2010-12-23	2012-07-04	Esteve Química, S.A.	Novel polymorphic form of efavirenz
CN103508973B (zh) *	2012-06-25	2016-04-27	上海迪赛诺药业有限公司	制备依非韦伦i型结晶的方法
CN105037175B (zh) *	2014-07-18	2017-02-22	盐城迪赛诺制药有限公司	一种用于提高依非韦伦中间体光学纯度的方法
US11780848B2 (en)	2015-10-16	2023-10-10	Abbvie Inc.	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1- carboxamide and solid state forms thereof
US11524964B2 (en)	2015-10-16	2022-12-13	Abbvie Inc.	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
SG11201802990RA (en)	2015-10-16	2018-05-30	Abbvie Inc	PROCESSES FOR THE PREPARATION OF (3S,4R)-3-ETHYL-4-(3H-IMIDAZO[1,2-a]PYRROLO[2,3-e]-PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE AND SOLID STATE FORMS THEREOF
US10550126B2 (en)	2015-10-16	2020-02-04	Abbvie Inc.	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-A]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
US11512092B2 (en)	2015-10-16	2022-11-29	Abbvie Inc.	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
US11365198B2 (en)	2015-10-16	2022-06-21	Abbvie Inc.	Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
CN114195761B (zh) *	2021-12-23	2023-04-14	浙江普洛家园药业有限公司	一种高纯度西他沙星3/2水合物的制备方法

Family Cites Families (8)

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Publication number	Priority date	Publication date	Assignee	Title
CA1282405C (en) *	1984-05-21	1991-04-02	Michael R. Violante	Method for making uniformly sized particles from water-insoluble organic compounds
US5519021A (en) *	1992-08-07	1996-05-21	Merck & Co., Inc.	Benzoxazinones as inhibitors of HIV reverse transcriptase
IL106507A (en) *	1992-08-07	1997-11-20	Merck & Co Inc	Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type
AU1694295A (en) *	1994-01-28	1995-08-15	Merck & Co., Inc.	Benzoxazinones as inhibitors of hiv reverse transcriptase
US5663467A (en) *	1995-01-23	1997-09-02	Merck & Co., Inc.	Synthesis of cyclopropylacetylene
US5633405A (en) *	1995-05-25	1997-05-27	Merck & Co., Inc.	Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one
WO1998033782A1 (en) *	1997-02-05	1998-08-06	Merck & Co., Inc.	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
IL132185A0 (en) *	1997-04-07	2001-03-19	Pont Pharmaceuticals Company M	Asymmetric synthesis of benzoxazinones via new intermediates

1998
- 1998-02-02 WO PCT/US1998/001999 patent/WO1998033782A1/en active IP Right Grant
- 1998-02-02 CN CNB011227095A patent/CN1191242C/zh not_active Expired - Lifetime
- 1998-02-02 AU AU62632/98A patent/AU738545C/en not_active Expired
- 1998-02-02 DE DE69841972T patent/DE69841972D1/de not_active Expired - Lifetime
- 1998-02-02 EP EP98904853A patent/EP0975609B1/en not_active Expired - Lifetime
- 1998-02-02 CZ CZ0276599A patent/CZ297535B6/cs not_active IP Right Cessation
- 1998-02-02 AT AT98904853T patent/ATE486065T1/de active
- 1998-02-02 CZ CZ20040883A patent/CZ304186B6/cs not_active IP Right Cessation
- 1998-02-02 KR KR1019997006985A patent/KR100573192B1/ko not_active IP Right Cessation
- 1998-02-02 SK SK1055-99A patent/SK284935B6/sk not_active IP Right Cessation
- 1998-02-02 CA CA002279198A patent/CA2279198C/en not_active Expired - Lifetime
- 1998-02-02 HU HU0001313A patent/HU229087B1/hu unknown
- 1998-02-02 NZ NZ336510A patent/NZ336510A/en not_active IP Right Cessation
- 1998-02-02 IL IL13071598A patent/IL130715A/xx not_active IP Right Cessation
- 1998-02-02 EE EEP199900341A patent/EE03827B1/xx unknown
- 1998-02-02 PL PL334478A patent/PL197740B1/pl unknown
- 1998-02-02 JP JP53319098A patent/JP3418626B2/ja not_active Expired - Lifetime
- 1998-02-02 EA EA199900720A patent/EA001805B1/ru not_active IP Right Cessation
- 1998-02-02 CN CN98802171A patent/CN1073991C/zh not_active Expired - Lifetime
1999
- 1999-08-04 NO NO19993779A patent/NO320128B1/no not_active IP Right Cessation
2002
- 2002-06-04 JP JP2002163198A patent/JP2003040874A/ja not_active Withdrawn
2010
- 2010-09-10 JP JP2010202879A patent/JP5295190B2/ja not_active Expired - Lifetime
2013
- 2013-04-22 JP JP2013089216A patent/JP2013139484A/ja active Pending
2015
- 2015-07-24 JP JP2015146631A patent/JP6126172B2/ja not_active Expired - Lifetime
2017
- 2017-01-11 JP JP2017002745A patent/JP2017061575A/ja active Pending

Also Published As

Publication number	Publication date
CA2279198A1 (en)	1998-08-06
AU6263298A (en)	1998-08-25
JP5295190B2 (ja)	2013-09-18
NZ336510A (en)	2001-04-27
WO1998033782A1 (en)	1998-08-06
IL130715A0 (en)	2000-06-01
EP0975609A1 (en)	2000-02-02
JP3418626B2 (ja)	2003-06-23
SK105599A3 (en)	2000-05-16
EP0975609A4 (en)	2001-02-21
CA2279198C (en)	2009-04-14
IL130715A (en)	2003-07-31
HUP0001313A2 (hu)	2000-10-28
JP2017061575A (ja)	2017-03-30
PL197740B1 (pl)	2008-04-30
CZ297535B6 (cs)	2007-01-03
EA199900720A1 (ru)	2000-04-24
NO993779D0 (no)	1999-08-04
EE9900341A (et)	2000-02-15
CZ304186B6 (cs)	2013-12-11
CN1191242C (zh)	2005-03-02
EP0975609B1 (en)	2010-10-27
SK284935B6 (sk)	2006-02-02
CN1246113A (zh)	2000-03-01
AU738545C (en)	2004-06-17
CN1073991C (zh)	2001-10-31
CN1385425A (zh)	2002-12-18
JP6126172B2 (ja)	2017-05-10
CZ276599A3 (cs)	2000-02-16
PL334478A1 (en)	2000-02-28
JP2013139484A (ja)	2013-07-18
ATE486065T1 (de)	2010-11-15
JP2000507972A (ja)	2000-06-27
HUP0001313A3 (en)	2002-12-28
JP2003040874A (ja)	2003-02-13
HU229087B1 (en)	2013-07-29
EE03827B1 (et)	2002-08-15
KR20000070735A (ko)	2000-11-25
JP2015205914A (ja)	2015-11-19
JP2011006472A (ja)	2011-01-13
NO993779L (no)	1999-10-05
DE69841972D1 (de)	2010-12-09
EA001805B1 (ru)	2001-08-27
AU738545B2 (en)	2001-09-20
KR100573192B1 (ko)	2006-04-24

Legal Events

Date	Code	Title	Description
2018-02-12	MK1K	Patent expired

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JP6126172B2 (ja)	2017-05-10	逆溶媒を使用する逆転写酵素阻害剤の結晶化方法
US20060009641A1 (en)	2006-01-12	Crystal forms of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
RU2275354C2 (ru)	2006-04-27	Способы получения кристаллов в-типа натеглинида
AU739211B2 (en)	2001-10-04	Crystalline macrolides and process for their preparation
JP2024038090A (ja)	2024-03-19	２，２，２－トリフルオロ酢酸１－（２，４－ジメチルフェニル）－２－［（３－メトキシフェニル）メチレン］ヒドラジド多形体およびその製造方法
KR20140108222A (ko)	2014-09-05	결정질 형태의 신속한 식별 및 제조를 위한 방법
JPH08333364A (ja)	1996-12-17	ｄ４Ｔ多形フォームＩ方法
AU760075B2 (en)	2003-05-08	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
ES2353458T3 (es)	2011-03-02	Procedimiento para la cristalización de un inhibidor de transcriptasa inversa usando un anti-solvente.
CN113683607B (zh)	2023-10-27	一种特力利汀中间体晶型ii及其制备方法
MXPA99007215A (en)	2000-02-02	Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
HUE025398T2 (en)	2016-02-29	New crystalline modification of CDB-4124