DK174184B1 - Benzothiopyrano[4,3,2-cd]indazoler, fremgangsmåder til fremstilling deraf samt præparater indeholdende disse - Google Patents

Benzothiopyrano[4,3,2-cd]indazoler, fremgangsmåder til fremstilling deraf samt præparater indeholdende disse Download PDF

Info

Publication number: DK174184B1
Authority: DK; Denmark
Prior art keywords: benzothiopyrano; ethyl; amino; structural formula; indazol
Prior art date: 1983-01-06

Application number

DK198306083A

Other languages

Danish (da)

English (en)

Other versions

DK608383A (da

DK608383D0 (da

Inventor

Leslie M Werbel

Edward F Elslager

Donald F Worth

Howard D H Showalter

Daniel F Ortwine

Original Assignee

Warner Lambert 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.)

1983-01-06

Filing date

1983-12-30

Publication date

2002-08-19

1983-12-30 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1983-12-30 Publication of DK608383D0 publication Critical patent/DK608383D0/da

1984-07-07 Publication of DK608383A publication Critical patent/DK608383A/da

2002-08-19 Application granted granted Critical

2002-08-19 Publication of DK174184B1 publication Critical patent/DK174184B1/da

Links

238000002360 preparation method Methods 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 21
GOLXQLMHTCVMKG-UHFFFAOYSA-N C1=CC(SC=2C3=CC=CC=2)=C2C3=NNC2=C1 Chemical class C1=CC(SC=2C3=CC=CC=2)=C2C3=NNC2=C1 GOLXQLMHTCVMKG-UHFFFAOYSA-N 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 118
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 110
239000000203 mixture Substances 0.000 claims description 89
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 74
229910052757 nitrogen Inorganic materials 0.000 claims description 60
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 59
-1 aminoethylamino Chemical group 0.000 claims description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 33
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239000000460 chlorine Substances 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 23
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239000001257 hydrogen Substances 0.000 claims description 21
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239000002253 acid Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
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ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
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239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
229910000679 solder Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
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235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
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238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
YOEWQQVKRJEPAE-UHFFFAOYSA-L succinylcholine chloride (anhydrous) Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C YOEWQQVKRJEPAE-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
235000001508 sulfur Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
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238000002054 transplantation Methods 0.000 description 1
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235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/06—Peri-condensed systems
- 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
- 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
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

DK198306083A 1983-01-06 1983-12-30 Benzothiopyrano[4,3,2-cd]indazoler, fremgangsmåder til fremstilling deraf samt præparater indeholdende disse DK174184B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US45616283A	1983-01-06	1983-01-06
US45616283		1983-01-06
US55940283A	1983-12-12	1983-12-12
US55940283		1983-12-12

Publications (3)

Publication Number	Publication Date
DK608383D0 DK608383D0 (da)	1983-12-30
DK608383A DK608383A (da)	1984-07-07
DK174184B1 true DK174184B1 (da)	2002-08-19

Family

ID=27038136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198306083A DK174184B1 (da)	1983-01-06	1983-12-30	Benzothiopyrano[4,3,2-cd]indazoler, fremgangsmåder til fremstilling deraf samt præparater indeholdende disse

Country Status (9)

Country	Link
EP (1)	EP0114002B1 (fr)
JP (2)	JPH0692415B2 (fr)
CA (1)	CA1206153A (fr)
DE (1)	DE3369994D1 (fr)
DK (1)	DK174184B1 (fr)
ES (4)	ES528713A0 (fr)
GR (1)	GR79496B (fr)
HK (1)	HK103089A (fr)
IE (1)	IE56749B1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1251451A (fr) *	1984-06-29	1989-03-21	Ellen M. Berman	Compositions a base de benzoselenio¬4,3,2-cd\| indazole; preparation et utilisation
CA1251450A (fr) *	1984-06-29	1989-03-21	David B. Capps	Compositions a base de benzopyrano¬4,3,2-cd\| indazole; preparation et utilisation
US4806654A (en) *	1987-03-23	1989-02-21	Warner-Lambert Company	Processes for the preparation of benzo(chalcogeno)(4,3,2-cd)indazoles and intermediates thereof
WO1992003421A2 (fr) *	1990-08-17	1992-03-05	E.I. Du Pont De Nemours And Company	Pyrazolines, pyrazolidines et hydrazines arthropodicides
US5569667A (en) *	1995-01-19	1996-10-29	Warner-Lambert Company	Treatment of prostate cancer
NZ303528A (en) *	1995-02-27	1998-08-26	Sanofi Winthrop Inc	Benzothiopyran[4,3,2-cd]indazole derivatives and medicaments
JPH11513020A (ja) *	1995-07-06	1999-11-09	ユニバーシティオブバーモント	抗腫瘍活性を有する新規ピリド−チオピラノインダゾール類
RU2281169C1 (ru)	2004-12-06	2006-08-10	Закрытое акционерное общество "Научно-производственный внедренческий центр "Уральский научно-исследовательский и проектный институт обогащения и механической обработки полезных ископаемых - Техника" (ЗАО НПВЦ "Уралмеханобр - Техника")	Флотационная колонная пневматическая машина
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US4197249A (en) *	1977-08-15	1980-04-08	American Cyanamid Company	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof

1983
- 1983-12-22 CA CA000444162A patent/CA1206153A/fr not_active Expired
- 1983-12-22 IE IE3056/83A patent/IE56749B1/en not_active IP Right Cessation
- 1983-12-29 EP EP83308029A patent/EP0114002B1/fr not_active Expired
- 1983-12-29 DE DE8383308029T patent/DE3369994D1/de not_active Expired
- 1983-12-30 DK DK198306083A patent/DK174184B1/da not_active IP Right Cessation
1984
- 1984-01-04 GR GR73430A patent/GR79496B/el unknown
- 1984-01-05 JP JP59000111A patent/JPH0692415B2/ja not_active Expired - Lifetime
- 1984-01-05 ES ES528713A patent/ES528713A0/es active Granted
- 1984-03-22 ES ES530851A patent/ES8505371A1/es not_active Expired
1985
- 1985-06-01 ES ES543807A patent/ES8604229A1/es not_active Expired
- 1985-06-01 ES ES543808A patent/ES8604230A1/es not_active Expired
1989
- 1989-12-28 HK HK1030/89A patent/HK103089A/en not_active IP Right Cessation
1993
- 1993-10-27 JP JP5267686A patent/JPH0751554B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES8600303A1 (es)	1985-10-01
ES543807A0 (es)	1986-01-16
GR79496B (fr)	1984-10-30
EP0114002B1 (fr)	1987-03-04
EP0114002A2 (fr)	1984-07-25
DE3369994D1 (en)	1987-04-09
IE56749B1 (en)	1991-12-04
EP0114002A3 (en)	1984-11-14
JPH06279385A (ja)	1994-10-04
JPH0692415B2 (ja)	1994-11-16
CA1206153A (fr)	1986-06-17
DK608383A (da)	1984-07-07
ES528713A0 (es)	1985-10-01
ES530851A0 (es)	1985-05-16
JPH0751554B2 (ja)	1995-06-05
IE833056L (en)	1984-07-06
JPS59134794A (ja)	1984-08-02
ES8604229A1 (es)	1986-01-16
HK103089A (en)	1990-01-05
ES8604230A1 (es)	1986-01-16
DK608383D0 (da)	1983-12-30
ES8505371A1 (es)	1985-05-16
ES543808A0 (es)	1986-01-16

Legal Events

Date	Code	Title	Description
2004-01-19	PUP	Patent expired

Publication	Publication Date	Title
AU4127400A (en)	2000-10-16	Derivatives of pyrimido(6,1-a)isoquinolin-4-one
NO170929B (no)	1992-09-21	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotiazolforbindelser
US4013665A (en)	1977-03-22	Antiviral, substituted 1,3-dimethyl-1h-pyrazolo(3,4b)quinolines
EP0114002B1 (fr)	1987-03-04	Benzothiopyrano(4,3,2-cd)indazoles, leur compositions pharmaceutiques et méthodes pour leur préparation
RU2138495C1 (ru)	1999-09-27	Тиоксантеноновые соединения и фармацевтические композиции, обладающие противоопухолевой активностью
EP0138302B1 (fr)	1988-03-09	Dérivés de la pyrazolo(3,4,5-kl)acridine, compositions pharmaceutiques les contenant et procédé pour leur préparation
AU601004B2 (en)	1990-08-30	Triazine derivatives
PT87160B (pt)	1992-07-31	Processo para a preparacao de 3h-1,2,3-triazolo{4,5-d}pirimidinas
EP0252682A2 (fr)	1988-01-13	Tétrazines
TW593307B (en)	2004-06-21	Sulfonamide-substituted benzopyran derivatives, processes for their preparation, their use as a medicament, and pharmaceutical preparations comprising them
US4604390A (en)	1986-08-05	Antibacterial benzo(chalcogeno)[4,3,2-cd]indazoles
US4582851A (en)	1986-04-15	Anti-bacterial 1,4-aminoalkylamino-9H-thioxanthen-9-one derivatives, compositions, and method of use therefor
CA1234117A (fr)	1988-03-15	7-anilinoisoquinoline-5,8-quinolines
EP0981528A1 (fr)	2000-03-01	Benzothiopyranopyridines regioisomeres a activite antitumorale
AU713107B2 (en)	1999-11-25	New pyrido-thiopyranoindazoles with antitumor activity
DK159108B (da)	1990-09-03	Analogifremgangsmaade til fremstilling af 6-anilino-5,8-quinoxalindioner
US4621086A (en)	1986-11-04	Method of treating leukemia with pyrazolo[3,4,5-kl]acridines
NZ206080A (en)	1987-01-23	3-cyano-5-(phenoxy or phenylthio)indol-2-ylamines
US5935969A (en)	1999-08-10	Pyrido-thiopyrandoinazoles with antitumor activity
EP0112419B1 (fr)	1986-07-23	Dérivés naphto triazoliques à activité pharmacologique
US4588730A (en)	1986-05-13	Pyrazolo[3,4,5-k1]acridine compositions and methods for their use as antimicrobials
EP0074712B1 (fr)	1985-07-24	Dérivés du naphtotriazole possédant une activité pharmaceutique
DK162098B (da)	1991-09-16	Benzopyrano(4,3,2-cd)indazolforbindelser, udgangsforbindelser til brug ved fremstilling heraf og farmaceutiske midler indeholdende saadanne forbindelser