JPH07506844A - 硝酸１，２‐ベンゾ‐イソチアゾリル‐３（２ｈ）オン‐１，１‐ジオキシドエステル，それらの製造法及びそれらを含む薬 - Google Patents

硝酸１，２‐ベンゾ‐イソチアゾリル‐３（２ｈ）オン‐１，１‐ジオキシドエステル，それらの製造法及びそれらを含む薬

Info

Publication number: JPH07506844A
Authority: JP; Japan
Prior art keywords: isothiazolyl; dioxide; benzo; compound; general formula
Prior art date: 1993-03-16
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.): Pending

Application number

JP6520474A

Other languages

English (en)

Japanese (ja)

Inventor

スンケル　カルロス

ファウ　ミグエル

プリエーゴ　ハイメ　ヘ

スタットコウ　ピエール

ストローマン　ダニエル

シャッテリーエ　シーアム　エス

シュレーゲルミルヒ　ロナルド

Original Assignee

セルモル　ソシエテ　アノニム

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.)

1993-03-16

Filing date

1994-03-15

Publication date

1995-07-27

1994-03-15 Application filed by セルモル　ソシエテ　アノニム filed Critical セルモル　ソシエテ　アノニム

1995-07-27 Publication of JPH07506844A publication Critical patent/JPH07506844A/ja

Status Pending legal-status Critical Current

Links

229940079593 drug Drugs 0.000 title claims description 15
239000003814 drug Substances 0.000 title claims description 14
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims description 13
229910017604 nitric acid Inorganic materials 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 5
150000002148 esters Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 26
208000024172 Cardiovascular disease Diseases 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
208000028867 ischemia Diseases 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
206010002383 Angina Pectoris Diseases 0.000 claims description 3
206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
229910002651 NO3 Chemical group 0.000 claims description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
229940124549 vasodilator Drugs 0.000 claims 1
239000003071 vasodilator agent Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
238000003756 stirring Methods 0.000 description 18
238000001953 recrystallisation Methods 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
239000000243 solution Substances 0.000 description 12
239000007787 solid Substances 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
239000002904 solvent Substances 0.000 description 10
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 8
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
238000005406 washing Methods 0.000 description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
150000002823 nitrates Chemical class 0.000 description 4
230000000304 vasodilatating effect Effects 0.000 description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229960002748 norepinephrine Drugs 0.000 description 3
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
210000000709 aorta Anatomy 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 2
229960000201 isosorbide dinitrate Drugs 0.000 description 2
239000000463 material Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000002040 relaxant effect Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001432959 Chernes Species 0.000 description 1
HEVGGTGPGPKZHF-UHFFFAOYSA-N Epilaurene Natural products CC1C(=C)CCC1(C)C1=CC=C(C)C=C1 HEVGGTGPGPKZHF-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000008238 Muscle Spasticity Diseases 0.000 description 1
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241000700159 Rattus Species 0.000 description 1
-1 Shargh i Inorganic materials 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
210000002376 aorta thoracic Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000004087 circulation Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960003711 glyceryl trinitrate Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000006060 molten glass Substances 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000036316 preload Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
208000018198 spasticity Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Life Sciences & Earth 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)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

JP6520474A 1993-03-16 1994-03-15 硝酸１，２‐ベンゾ‐イソチアゾリル‐３（２ｈ）オン‐１，１‐ジオキシドエステル，それらの製造法及びそれらを含む薬 Pending JPH07506844A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH782/93-7		1993-03-16
CH782/93A CH685700A5 (fr)	1993-03-16	1993-03-16	Esters nitriques de 1,2-benzo-isothiazolyl-3(2H)one-1,1-dioxyde, procédé de préparation de ces esters et médicaments contenant ces esters.
PCT/CH1994/000057 WO1994021618A1 (fr)	1993-03-16	1994-03-15	Esters nitriques de 1,2-benzo-isothiazolyl-3(2h)one-1, 1-dioxyde, procede de preparation de ces esters et medicaments contenant ces esters

Publications (1)

Publication Number	Publication Date
JPH07506844A true JPH07506844A (ja)	1995-07-27

Family

ID=4195059

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6520474A Pending JPH07506844A (ja)	1993-03-16	1994-03-15	硝酸１，２‐ベンゾ‐イソチアゾリル‐３（２ｈ）オン‐１，１‐ジオキシドエステル，それらの製造法及びそれらを含む薬

Country Status (6)

Country	Link
EP (1)	EP0640078A1 (fr)
JP (1)	JPH07506844A (fr)
AU (1)	AU6153694A (fr)
CA (1)	CA2135921A1 (fr)
CH (1)	CH685700A5 (fr)
WO (1)	WO1994021618A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1288123B1 (it) *	1996-09-04	1998-09-10	Nicox Sa	Uso di nitroderivati per l'incontinenza urinaria

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4342761A (en) *	1979-11-01	1982-08-03	John Wyeth & Brother Limited	Piperidine derivatives
JPS6137766A (ja) *	1984-07-31	1986-02-22	Sankyo Co Ltd	フタルイミド誘導体およびその製造法
DE3726425A1 (de) *	1987-03-18	1988-09-29	Bayer Ag	Basisch substituierte saccharine
DE4003541C1 (fr) *	1990-02-06	1991-08-08	Alter S.A., Madrid, Es
IT1244472B (it) *	1990-12-14	1994-07-15	Italfarmaco Spa	Benzossazinoni e benzotiazinoni ad attivita' cardiovascolare

1993
- 1993-03-16 CH CH782/93A patent/CH685700A5/fr not_active IP Right Cessation
1994
- 1994-03-15 AU AU61536/94A patent/AU6153694A/en not_active Abandoned
- 1994-03-15 CA CA002135921A patent/CA2135921A1/fr not_active Abandoned
- 1994-03-15 JP JP6520474A patent/JPH07506844A/ja active Pending
- 1994-03-15 WO PCT/CH1994/000057 patent/WO1994021618A1/fr not_active Ceased
- 1994-03-15 EP EP94908247A patent/EP0640078A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CH685700A5 (fr)	1995-09-15
CA2135921A1 (fr)	1994-09-29
WO1994021618A1 (fr)	1994-09-29
EP0640078A1 (fr)	1995-03-01
AU6153694A (en)	1994-10-11

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