CA1037466A - Process for the preparation of steroidal derivatives of bendazolic acid - Google Patents

Process for the preparation of steroidal derivatives of bendazolic acid

Info

Publication number: CA1037466A
Authority: CA; Canada
Prior art keywords: indazol; benzyl; oxy; cortisone; preparation
Prior art date: 1975-02-13
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

CA245,872A

Other languages

English (en)

French (fr)

Other versions

CA245872S (en

Inventor

Leandro Baiocchi

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.)

Angelini Acraf SpA

Original Assignee

Aziende Chimiche Riunite Angelini Francesco ACRAF SpA

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.)

1975-02-13

Filing date

1976-02-12

Publication date

1978-08-29

1976-02-12 Application filed by Aziende Chimiche Riunite Angelini Francesco ACRAF SpA filed Critical Aziende Chimiche Riunite Angelini Francesco ACRAF SpA

1978-08-29 Application granted granted Critical

1978-08-29 Publication of CA1037466A publication Critical patent/CA1037466A/en

Status Expired legal-status Critical Current

Links

BYFMCKSPFYVMOU-UHFFFAOYSA-N bendazac Chemical class C12=CC=CC=C2C(OCC(=O)O)=NN1CC1=CC=CC=C1 BYFMCKSPFYVMOU-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims abstract description 5
230000003637 steroidlike Effects 0.000 title 1
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims abstract description 17
229960000890 hydrocortisone Drugs 0.000 claims abstract description 8
229960005205 prednisolone Drugs 0.000 claims abstract description 7
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims abstract description 7
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims abstract description 7
229960004618 prednisone Drugs 0.000 claims abstract description 6
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims abstract description 5
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims abstract description 5
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims abstract description 5
229960004544 cortisone Drugs 0.000 claims abstract description 5
150000002148 esters Chemical class 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
KLJKSHJIQPPZKG-UHFFFAOYSA-N 2-(1-benzylindazol-3-yl)oxyacetyl chloride Chemical compound C12=CC=CC=C2C(OCC(=O)Cl)=NN1CC1=CC=CC=C1 KLJKSHJIQPPZKG-UHFFFAOYSA-N 0.000 claims abstract 2
239000000126 substance Substances 0.000 abstract description 5
230000003412 degenerative effect Effects 0.000 abstract description 2
230000001338 necrotic effect Effects 0.000 abstract description 2
230000002792 vascular Effects 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract 1
230000001575 pathological effect Effects 0.000 abstract 1
238000001228 spectrum Methods 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229960005149 bendazac Drugs 0.000 description 5
239000000243 solution Substances 0.000 description 5
-1 1-benzyl-1H-indazol-3-yl Chemical group 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA245,872A 1975-02-13 1976-02-12 Process for the preparation of steroidal derivatives of bendazolic acid Expired CA1037466A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT48150/75A IT1036870B (it)	1975-02-13	1975-02-13	Derivati steroidei dell acido bendazolico

Publications (1)

Publication Number	Publication Date
CA1037466A true CA1037466A (en)	1978-08-29

Family

ID=11264844

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA245,872A Expired CA1037466A (en)	1975-02-13	1976-02-12	Process for the preparation of steroidal derivatives of bendazolic acid

Country Status (11)

Country	Link
US (1)	US4001219A (2)
JP (1)	JPS5339436B2 (2)
AR (1)	AR212329A1 (2)
CA (1)	CA1037466A (2)
CH (1)	CH606110A5 (2)
DE (1)	DE2601367C3 (2)
ES (1)	ES444231A1 (2)
FR (1)	FR2300570A1 (2)
GB (1)	GB1505461A (2)
IT (1)	IT1036870B (2)
MX (1)	MX3276E (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4376767A (en) *	1981-01-02	1983-03-15	Merck & Co., Inc.	Pyridylmethyl esters of selected bio-affecting carboxylic acids
CA2136803A1 (en) *	1993-12-22	1995-06-23	Kazumi Ogata	Steroid derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH83A (fr) *	1888-11-17	1889-01-10	Fontainemelon Horlogerie	Perfectionnements apportés à la construction des montres de tous calibres
GB919830A (en) *	1959-07-16	1963-02-27	Leo Ab	Esters of cortical steroid hormones
GB1272841A (en) *	1969-01-23	1972-05-03	Leo Ab	New corticoid steroid compounds of cytostatic interest
DE2064859C3 (de) *	1970-12-30	1980-05-22	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue 6 a -Fluor-16 a , 18dimethyl-l,4-pregnadien-3,20-dion Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel

1975
- 1975-02-13 IT IT48150/75A patent/IT1036870B/it active
- 1975-12-18 CH CH1644775A patent/CH606110A5/xx not_active IP Right Cessation
1976
- 1976-01-06 JP JP108576A patent/JPS5339436B2/ja not_active Expired
- 1976-01-09 GB GB873/76A patent/GB1505461A/en not_active Expired
- 1976-01-09 US US05/647,749 patent/US4001219A/en not_active Expired - Lifetime
- 1976-01-12 ES ES444231A patent/ES444231A1/es not_active Expired
- 1976-01-14 MX MX002081U patent/MX3276E/es unknown
- 1976-01-15 DE DE2601367A patent/DE2601367C3/de not_active Expired
- 1976-02-10 AR AR262196A patent/AR212329A1/es active
- 1976-02-12 CA CA245,872A patent/CA1037466A/en not_active Expired
- 1976-02-13 FR FR7604068A patent/FR2300570A1/fr active Granted

Also Published As

Publication number	Publication date
DE2601367B2 (de)	1981-04-09
ES444231A1 (es)	1977-05-01
FR2300570B1 (2)	1979-09-21
CH606110A5 (2)	1978-10-13
JPS5195071A (2)	1976-08-20
DE2601367A1 (de)	1976-08-26
US4001219A (en)	1977-01-04
IT1036870B (it)	1979-10-30
JPS5339436B2 (2)	1978-10-21
AR212329A1 (es)	1978-06-30
GB1505461A (en)	1978-03-30
FR2300570A1 (fr)	1976-09-10
MX3276E (es)	1980-08-14
DE2601367C3 (de)	1982-04-22

Publication	Publication Date	Title
KR100333151B1 (ko)	2002-09-04	단량체성담즙산유도체
CA2098256C (en)	2004-08-24	Bile acid derivatives, process for their preparation and use of these compounds as pharmaceuticals
JP2947944B2 (ja)	1999-09-13	１７β―カルボキシ、カルボチオおよびアミドアンドロスタン誘導体のラクトン誘導体
EP1169337B1 (en)	2004-08-25	Steroid nitrates for the treatment of oxidative injury and endothelial dysfunction
NO156203B (no)	1987-05-04	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 6alfa-methylprednisolon-derivater.
US5015746A (en)	1991-05-14	11β, 17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-[(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienoate]
US3723484A (en)	1973-03-27	17-chloro steroids
US4001219A (en)	1977-01-04	Steroidal derivatives of bendazolic acid and process for the preparation of the same
DE3106815A1 (de)	1982-09-09	"chemische verbindungen, verfahren zu ihrer herstellung und ihre verwendung als antigene oder immunadsorbentien"
US3663579A (en)	1972-05-16	Dimeric steroid-21-alkyl-carbonates and process for their manufacture
JPS5837320B2 (ja)	1983-08-15	プレグナンサンユウドウタイノセイホウ
US3798216A (en)	1974-03-19	9-fluoro-11beta,21-dihydroxy-16alpha,17-(2-propenylidenedioxy)-pregna-1,4-diene-3,20-dione and derivatives thereof
US3472836A (en)	1969-10-14	Acyl derivatives of proscillaridin a and process for the production thereof
US4404199A (en)	1983-09-13	Salification products of cholic acids with trimethoxy-3,4,5-benzoic ester of 2-phenyl-2-dimenthylaminobutanol, having pharmacotherapeutic action, process for their preparation and therapeutic compositions containing them as active principle
EP0320253B1 (en)	1993-06-09	21-alkoxysteroid compounds
US2705232A (en)	1955-03-29	Ternorcholanylthiazoles
US3657434A (en)	1972-04-18	21-(tetrahalocyclobutyl carboxylic acid) steroid esters
CA1110616A (en)	1981-10-13	.delta. su4,9 xx-pregnane derivatives, their use as progestational and/or ovulation-inhibiting agents and process for their preparation
DE2264001C2 (de)	1982-08-26	11&beta;-Hydroxy-2',2'-dimethyl-1,4-pregnadieno[17,16&alpha;-d]-1',3'-oxathiolan-3,20-dion
CA1113452A (en)	1981-12-01	Water-soluble corticoids
JPS5817480B2 (ja)	1983-04-07	コルチコステロイド２１− エステルユウドウタイノセイゾウホウ
US3528966A (en)	1970-09-15	2-and/or-4-halogenated 17-oxygenated 3-aminoestra-1,3,5(10)-trienes
KR820002025B1 (ko)	1982-10-25	하이드로 코르티죤 유도체의 제조방법
US3163664A (en)	1964-12-29	21-hemi-alpha, beta-dialkylsuccinates of corticoids
US5250711A (en)	1993-10-05	Amine salts of alkane-1,n-dicarboxylic acid mono-(2-sulfato-ethyl) amides