AU602891B2 - 4H-1-benzopyran-4-one derivatives, a process for their preparation and their use as medicaments - Google Patents

4H-1-benzopyran-4-one derivatives, a process for their preparation and their use as medicaments

Info

Publication number
AU602891B2
AU602891B2 AU71397/87A AU7139787A AU602891B2 AU 602891 B2 AU602891 B2 AU 602891B2 AU 71397/87 A AU71397/87 A AU 71397/87A AU 7139787 A AU7139787 A AU 7139787A AU 602891 B2 AU602891 B2 AU 602891B2
Authority
AU
Australia
Prior art keywords
alkyl
aryl
cycloalkyl
represents hydrogen
integer
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
AU71397/87A
Other languages
English (en)
Other versions
AU7139787A (en
Inventor
Alihussein Nomanbhai Dohadwalla
Samba Laxminarayan Kattige
Aftab Dawoodbhai Lakdawalla
Ramchandra Ganapati Naik
Richard Helmut Rupp
Noel John De Souza
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
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.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of AU7139787A publication Critical patent/AU7139787A/en
Application granted granted Critical
Publication of AU602891B2 publication Critical patent/AU602891B2/en
Anticipated expiration legal-status Critical
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40Oxygen atoms
    • C07D211/42Oxygen atoms attached in position 3 or 5
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Transplantation (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
AU71397/87A 1986-04-11 1987-04-10 4H-1-benzopyran-4-one derivatives, a process for their preparation and their use as medicaments Expired AU602891B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3612337 1986-04-11
DE19863612337 DE3612337A1 (de) 1986-04-11 1986-04-11 4h-1-benzopyran-4-on-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Publications (2)

Publication Number Publication Date
AU7139787A AU7139787A (en) 1987-10-15
AU602891B2 true AU602891B2 (en) 1990-11-01

Family

ID=6298535

Family Applications (1)

Application Number Title Priority Date Filing Date
AU71397/87A Expired AU602891B2 (en) 1986-04-11 1987-04-10 4H-1-benzopyran-4-one derivatives, a process for their preparation and their use as medicaments

Country Status (16)

Country Link
US (1) US4900727A (Sortimente)
EP (1) EP0241003B1 (Sortimente)
JP (1) JPH0686446B2 (Sortimente)
KR (1) KR950009861B1 (Sortimente)
AT (2) ATE95519T1 (Sortimente)
AU (1) AU602891B2 (Sortimente)
CA (1) CA1332238C (Sortimente)
DE (2) DE3612337A1 (Sortimente)
DK (1) DK169760B1 (Sortimente)
ES (1) ES2060582T3 (Sortimente)
HK (1) HK1006021A1 (Sortimente)
IE (1) IE62244B1 (Sortimente)
IL (1) IL82149A (Sortimente)
IN (1) IN164232B (Sortimente)
PT (1) PT84654B (Sortimente)
ZA (1) ZA872555B (Sortimente)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU628409B2 (en) * 1988-10-28 1992-09-17 Hoechst Aktiengesellschaft The use of 4h-1-benzopyran-4-one derivatives, novel 4h-1- benzopyran-4-one derivatives, and pharmaceuticals containing them
AU653800B2 (en) * 1991-04-10 1994-10-13 Hoechst Aktiengesellschaft 5,7-dihydroxy-2-methyl-8-{4-(3-hydroxy-1-(1-propyl) piperidinyl}-4H-1-benzophyran-4-one, its preparation and its use

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5284856A (en) * 1988-10-28 1994-02-08 Hoechst Aktiengesellschaft Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives
US5278174A (en) * 1990-06-04 1994-01-11 Scios Nova, Inc. Sigma binding site agents
US6011024A (en) 1991-08-28 2000-01-04 Imperial College Of Science Technology & Medicine Steroid sulphatase inhibitors
GB9604709D0 (en) * 1996-03-05 1996-05-01 Imperial College A compound
US6476011B1 (en) 1991-08-28 2002-11-05 Sterix Limited Methods for introducing an estrogenic compound
US6903084B2 (en) 1991-08-28 2005-06-07 Sterix Limited Steroid sulphatase inhibitors
SK280617B6 (sk) * 1992-01-16 2000-05-16 Hoechst Aktiengesellschaft Arylcykloalkylové deriváty, spôsob ich prípravy, f
US5733920A (en) * 1995-10-31 1998-03-31 Mitotix, Inc. Inhibitors of cyclin dependent kinases
US6506792B1 (en) 1997-03-04 2003-01-14 Sterix Limited Compounds that inhibit oestrone sulphatase and/or aromatase and methods for making and using
US20060241173A1 (en) * 1996-02-16 2006-10-26 Sterix Ltd. Compound
US6087366A (en) * 1996-03-07 2000-07-11 The Trustees Of Columbia University In The City Of New York Use of flavopiridol or a pharmaceutically acceptable salt thereof for inhibiting cell damage or cell death
US5849733A (en) * 1996-05-10 1998-12-15 Bristol-Myers Squibb Co. 2-thio or 2-oxo flavopiridol analogs
US5908934A (en) * 1996-09-26 1999-06-01 Bristol-Myers Squibb Company Process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs
DE19802449A1 (de) * 1998-01-23 1999-07-29 Hoechst Marion Roussel De Gmbh Verfahren zur Herstellung von (-)cis-3-Hydroxy-1-methyl-4-(2,4,6-trimethoxypyhenyl)-piperidin
GB9807779D0 (en) * 1998-04-09 1998-06-10 Ciba Geigy Ag Organic compounds
US6399633B1 (en) * 1999-02-01 2002-06-04 Aventis Pharmaceuticals Inc. Use of 4-H-1-benzopryan-4-one derivatives as inhibitors of smooth muscle cell proliferation
DE19959546A1 (de) * 1999-12-09 2001-06-21 Rhone Poulenc Rorer Gmbh Pharmazeutische Zubereitung zur Behandlung von Tumorerkrankungen
US7335650B2 (en) 2000-01-14 2008-02-26 Sterix Limited Composition
US6576647B2 (en) 2000-01-18 2003-06-10 Aventis Pharmaceuticals Inc. Pseudopolymorph of (—)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8[4R-(3S-hydroxy -1-methyl)piperidinyl]-4H-1-benzopyran-4-one
US6821990B2 (en) 2000-01-18 2004-11-23 Aventis Pharma Deutschland Gmbh Ethanol solvate of (-)-cis-2-(2-chlorophenyl)-5, 7-dihydroxy-8 [4R-(3S-hydroxy-1-M ethyl) piperidinyl]-4H-1-benzopyran-4-one
MXPA02006965A (es) * 2000-01-18 2004-09-06 Aventis Pharma Inc Solvato de etanol de (-) -cis-2 -(2-clorofenil) -5, 7-dihidroxi -8[4r-(3s -hidroxi -1-metil] piperidinil] -4h-1 -benzopiran-4 -ona.
ES2222332T3 (es) * 2000-01-18 2005-02-01 Aventis Pharmaceuticals Inc. Seudopolimorfo de hidrocloruro de (-)-cis-2-(2-clorofenil)-5,7-dihidroxi-8(4r-(3s-hidroxi-1-metil)piperidinil)-4h-1-benzopiran-4-ona.
FR2805538B1 (fr) * 2000-02-29 2006-08-04 Hoechst Marion Roussel Inc Nouveaux derives de flavones, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation
KR100423899B1 (ko) 2000-05-10 2004-03-24 주식회사 엘지생명과학 세포 증식 억제제로 유용한 1,1-디옥소이소티아졸리딘을갖는 인다졸
AU2003234733B2 (en) 2002-04-17 2009-01-29 Cytokinetics, Inc. Compounds, compositions, and methods
US7271193B2 (en) * 2002-07-08 2007-09-18 Nicholas Piramal India, Ltd. Inhibitors of cyclin-dependent kinases and their use
US7884127B2 (en) * 2002-07-08 2011-02-08 Pirimal Life Sciences Ltd. Inhibitors of cyclin dependent kinases and their use
US7915301B2 (en) 2002-07-08 2011-03-29 Piramal Life Science Limited Inhibitors of cyclin dependent kinases and their use
AU2003252025A1 (en) * 2002-07-17 2004-02-02 Cytokinetics, Inc. Compounds, compositions, and methods
WO2004024086A2 (en) * 2002-09-13 2004-03-25 Cytokinetics, Inc. Compounds, compositions and methods
WO2005042697A2 (en) * 2003-10-06 2005-05-12 Cytokinetics, Inc. Compounds, compositions and methods
JP2007513962A (ja) * 2003-12-09 2007-05-31 アメリカ合衆国 免疫応答を抑制するため、または増殖性障害を治療するための方法
WO2005058341A2 (en) * 2003-12-11 2005-06-30 Theravance, Inc. Compositions for use in the treatment of mutant receptor tyrosine kinase driven cellular proliferative diseases
ES2552338T3 (es) 2005-01-21 2015-11-27 Astex Therapeutics Limited Compuestos farmacéuticos
WO2007148158A1 (en) 2006-06-21 2007-12-27 Piramal Life Sciences Limited Enantiomerically pure flavone derivatives for the treatment of poliferative disorders and processes for their preparation
US8916552B2 (en) 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
US8883790B2 (en) 2006-10-12 2014-11-11 Astex Therapeutics Limited Pharmaceutical combinations
TWI461194B (zh) 2009-05-05 2014-11-21 Piramal Entpr Ltd 吡咯啶取代黃酮作為輻射致敏劑
CA2790993A1 (en) 2010-02-26 2011-09-01 Piramal Enterprises Limited Pyrrolidine substituted flavones for the treatment of inflammatory disorders
ES2685171T3 (es) 2010-06-14 2018-10-05 The Scripps Research Institute Reprogramación de células a un nuevo destino
TW201300105A (zh) 2011-05-31 2013-01-01 Piramal Life Sciences Ltd 治療頭頸鱗狀細胞癌之相乘藥物組合物
US9776989B2 (en) 2013-04-10 2017-10-03 Council Of Scientific & Industrial Research Chromone alkaloid dysoline for the treatment of cancer and inflammatory disorders
WO2014170914A1 (en) 2013-04-17 2014-10-23 Council Of Scientific And Industrial Research Rohitukine analogs as cyclin-dependent kinase inhibitors and a process for the preparation thereof
CN105530931B (zh) 2013-07-12 2019-11-08 皮拉马尔企业有限公司 用于治疗黑素瘤的药物组合
EP3218005B1 (en) 2014-11-12 2023-01-04 Seagen Inc. Glycan-interacting compounds and methods of use
BR112017022666A8 (pt) 2015-04-20 2022-10-18 Tolero Pharmaceuticals Inc Preparando resposta à alvocidib por perfilamento mitocondrial
TR201911032T4 (tr) 2015-05-18 2019-08-21 Tolero Pharmaceuticals Inc Artırılmış biyoyararlanıma sahip alvocıdıb ön ilaçları.
JP7083497B2 (ja) 2015-08-03 2022-06-13 スミトモ ファーマ オンコロジー, インコーポレイテッド がんの処置のための併用療法
JP7066613B2 (ja) 2015-11-12 2022-05-13 シージェン インコーポレイテッド グリカン相互作用化合物および使用方法
EP3541847A4 (en) 2016-11-17 2020-07-08 Seattle Genetics, Inc. COMPOUNDS INTERACTING WITH GLYCANE AND METHODS OF USE
US11279694B2 (en) 2016-11-18 2022-03-22 Sumitomo Dainippon Pharma Oncology, Inc. Alvocidib prodrugs and their use as protein kinase inhibitors
CN110234659A (zh) 2016-12-19 2019-09-13 特雷罗药物股份有限公司 用于敏感性分析的分析肽和方法
AU2018226824A1 (en) 2017-03-03 2019-09-19 Seagen Inc. Glycan-interacting compounds and methods of use
US11497756B2 (en) 2017-09-12 2022-11-15 Sumitomo Pharma Oncology, Inc. Treatment regimen for cancers that are insensitive to BCL-2 inhibitors using the MCL-1 inhibitor alvocidib
KR20210099066A (ko) 2018-12-04 2021-08-11 스미토모 다이니폰 파마 온콜로지, 인크. 암의 치료를 위한 작용제로서 사용하기 위한 cdk9 억제제 및 그의 다형체
US11793802B2 (en) 2019-03-20 2023-10-24 Sumitomo Pharma Oncology, Inc. Treatment of acute myeloid leukemia (AML) with venetoclax failure
JPWO2020213714A1 (Sortimente) * 2019-04-18 2020-10-22

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2591484A (en) * 1983-03-25 1984-09-27 Bayer Aktiengesellschaft Chromone- and thiochromone- substituted 1,4-dihydropyridine derivatives
EP0137193A2 (de) * 1983-08-12 1985-04-17 Hoechst Aktiengesellschaft Chromonalkaloid, Verfahren zu seiner Isolierung aus Dysoxylum Binectariferum, und seine Verwendung als Arzneimittel
AU5107085A (en) * 1984-12-15 1986-06-19 Bayer Aktiengesellschaft 1,4-dihydropyridine carboxamide derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1223690A (en) * 1967-10-17 1971-03-03 Fisons Pharmaceuticals Ltd Substituted chromon-2-carboxylic acids
DE2731566A1 (de) * 1977-07-13 1979-02-01 Bayer Ag Verfahren zur herstellung von neuen chromon-derivaten, sowie ihre verwendung als pflanzenschutzmittel
GB2101115A (en) * 1980-10-23 1983-01-12 Pfizer Ltd Thromboxane synthetase inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2591484A (en) * 1983-03-25 1984-09-27 Bayer Aktiengesellschaft Chromone- and thiochromone- substituted 1,4-dihydropyridine derivatives
EP0137193A2 (de) * 1983-08-12 1985-04-17 Hoechst Aktiengesellschaft Chromonalkaloid, Verfahren zu seiner Isolierung aus Dysoxylum Binectariferum, und seine Verwendung als Arzneimittel
AU5107085A (en) * 1984-12-15 1986-06-19 Bayer Aktiengesellschaft 1,4-dihydropyridine carboxamide derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU628409B2 (en) * 1988-10-28 1992-09-17 Hoechst Aktiengesellschaft The use of 4h-1-benzopyran-4-one derivatives, novel 4h-1- benzopyran-4-one derivatives, and pharmaceuticals containing them
AU653800B2 (en) * 1991-04-10 1994-10-13 Hoechst Aktiengesellschaft 5,7-dihydroxy-2-methyl-8-{4-(3-hydroxy-1-(1-propyl) piperidinyl}-4H-1-benzophyran-4-one, its preparation and its use

Also Published As

Publication number Publication date
EP0241003B1 (de) 1993-10-06
DK185287A (da) 1987-10-12
IN164232B (Sortimente) 1989-02-04
US4900727A (en) 1990-02-13
DE3787661D1 (de) 1993-11-11
ATA260587A (de) 1989-07-15
IE62244B1 (en) 1995-01-11
AU7139787A (en) 1987-10-15
ZA872555B (en) 1987-11-25
CA1332238C (en) 1994-10-04
PT84654B (pt) 1989-12-29
JPH0686446B2 (ja) 1994-11-02
KR870010045A (ko) 1987-11-30
ES2060582T3 (es) 1994-12-01
IL82149A (en) 1994-01-25
PT84654A (de) 1987-05-01
JPS62242680A (ja) 1987-10-23
KR950009861B1 (en) 1995-08-29
DK169760B1 (da) 1995-02-20
EP0241003A2 (de) 1987-10-14
IL82149A0 (en) 1987-10-30
DE3612337A1 (de) 1987-10-15
EP0241003A3 (en) 1988-10-12
AT389875B (de) 1990-02-12
ATE95519T1 (de) 1993-10-15
DK185287D0 (da) 1987-04-10
IE870941L (en) 1987-10-11
HK1006021A1 (en) 1999-02-05

Similar Documents

Publication Publication Date Title
AU602891B2 (en) 4H-1-benzopyran-4-one derivatives, a process for their preparation and their use as medicaments
IL113011A (en) R-mandelic acid salt of (2s,3s)-3- (2-methoxybenzylamino)-2- phenylpiperidine
HU9400352D0 (en) New quinoline- and naphtiridine-carboxylic acid derivatives
ES8104264A1 (es) Procedimiento para la preparacion de n- (trimetoxibencil)- n'-fenilpiperazinas
IE43847L (en) N-substituted phenylpiperidine derivatives.
PT93126A (pt) Processo para a preparacao de eteres carboxialquilicos da 2-amino-7- -hidroxitetralina
IE822330L (en) 2,2-disubstituted-ethylamines
ES2006994A6 (es) Procedimiento para la preparacion de derivados de los acidos quinolincarboxilicos.
PT90635A (pt) Processo para a preparacao de derivados do acido n-(5,6,7,8-tetra-hidropirido-{2,3-d}pirimidin-6-il-alcanoil)glutamico
DE3787030D1 (de) 1-carboxy-1-vinyloxyiminoaminothiazol-cephalosporin-derivate und deren herstellung.
PT78918A (en) Process for preparing novel benzofuran derivatives
ZA888663B (en) Substituted derivatives of 20,21-dinoreburanamenine,their preparation process and the new intermediates thus obtained,their use as medicaments and the pharmaceutical compositions containing them
AU577159B2 (en) Morpholinoethylamino-1,3,4-thiadiazole compounds
ES8504754A1 (es) Procedimiento para preparar la n-(3-trifluorometil fenil)-n-propargil-piperazina.
IL72681A (en) 4-alkyl-5-haloimidazole-1-carboxylic acid esters and amides,their preparation and their use as nitrification inhibitors
ZA924888B (en) Process for the synthesis of enantiomers of 3-aminochroman compounds
DE3470741D1 (en) Azolylmethylcycloacetals, process for their preparation and their use as medicaments
ES8202544A1 (es) Procedimiento para la preparacion de 2-fenilamino-imidazoli-nas -(2) sustituidas
ZA807905B (en) 2-phenylamino-imidazolines-(2),compositions thereof and process for the preparation thereof
AT383811B (de) Verfahren zur herstellung von monoalkalisalzen von 7-amino-3-cephem-4-carbonsaeurederivaten
GR3015467T3 (en) p-Oxybenzoic acid derivatives, process for preparing them and their use as medicaments.
DE69109072D1 (de) Aminoalkylketonderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Anwendungen.
JPS5387389A (en) Novel cephalosporin derivative, pharmaceuticals containing the same, and its preparation