IL135842A - Use of 3-carboalkoxy-2,3-dihydro-1h-phenothiazin-4-[10h]-one derivatives for the preparation of a medicament for treating grand mal and partial seizures in a mammal - Google Patents

Use of 3-carboalkoxy-2,3-dihydro-1h-phenothiazin-4-[10h]-one derivatives for the preparation of a medicament for treating grand mal and partial seizures in a mammal

Info

Publication number: IL135842A
Authority: IL; Israel
Prior art keywords: methyl; dihydro; phenothiazin; coor; acid
Prior art date: 1997-10-27

Application number

IL13584298A

Other languages

English (en)

Other versions

IL135842A0 (en

Original Assignee

Univ Howard

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.)

1997-10-27

Filing date

1998-10-27

Publication date

2004-06-01

1998-10-27 Application filed by Univ Howard filed Critical Univ Howard

2001-05-20 Publication of IL135842A0 publication Critical patent/IL135842A0/xx

2004-06-01 Publication of IL135842A publication Critical patent/IL135842A/en

Links

206010010904 Convulsion Diseases 0.000 title claims description 16
239000003814 drug Substances 0.000 title claims description 6
241000124008 Mammalia Species 0.000 title claims description 5
208000034308 Grand mal convulsion Diseases 0.000 title claims description 4
206010061334 Partial seizures Diseases 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
229950000688 phenothiazine Drugs 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000002990 phenothiazines Chemical class 0.000 abstract description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 7
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
125000001246 bromo group Chemical group Br* 0.000 abstract description 2
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 53
239000000203 mixture Substances 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
239000013078 crystal Substances 0.000 description 30
241001465754 Metazoa Species 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 26
150000001875 compounds Chemical class 0.000 description 24
238000012360 testing method Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000009472 formulation Methods 0.000 description 22
239000007788 liquid Substances 0.000 description 22
239000004480 active ingredient Substances 0.000 description 20
239000007787 solid Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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239000000538 analytical sample Substances 0.000 description 13
238000010438 heat treatment Methods 0.000 description 13
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239000012071 phase Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
239000001961 anticonvulsive agent Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229960003965 antiepileptics Drugs 0.000 description 9
239000000243 solution Substances 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000000034 method Methods 0.000 description 8
-1 anthelminics Substances 0.000 description 7
230000001773 anti-convulsant effect Effects 0.000 description 7
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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239000004615 ingredient Substances 0.000 description 6
YOELNWPMMURSQH-UHFFFAOYSA-N methyl 2-methyl-4,6-dioxocyclohexane-1-carboxylate Chemical compound COC(=O)C1C(C)CC(=O)CC1=O YOELNWPMMURSQH-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 6
239000003826 tablet Substances 0.000 description 6
LDGHLZFFKMEAOE-UHFFFAOYSA-N 2-amino-5-bromobenzenethiol Chemical compound NC1=CC=C(Br)C=C1S LDGHLZFFKMEAOE-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
SFEPTOBOJHIYPH-UHFFFAOYSA-N butyl 2-methyl-4,6-dioxocyclohexane-1-carboxylate Chemical compound CCCCOC(=O)C1C(C)CC(=O)CC1=O SFEPTOBOJHIYPH-UHFFFAOYSA-N 0.000 description 4
239000006071 cream Substances 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
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RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
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230000001988 toxicity Effects 0.000 description 4
KOBHMYVVCCJHNM-UHFFFAOYSA-N 1,2,3,10-tetrahydrophenothiazin-4-one Chemical compound S1C2=CC=CC=C2NC2=C1C(=O)CCC2 KOBHMYVVCCJHNM-UHFFFAOYSA-N 0.000 description 3
VUMZNLOQJGKGNE-UHFFFAOYSA-N 2-amino-5-methylbenzenethiol Chemical compound CC1=CC=C(N)C(S)=C1 VUMZNLOQJGKGNE-UHFFFAOYSA-N 0.000 description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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241000700159 Rattus Species 0.000 description 3
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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238000007920 subcutaneous administration Methods 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
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241000220479 Acacia Species 0.000 description 2
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235000010643 Leucaena leucocephala Nutrition 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/12—Antiepileptics; Anticonvulsants for grand-mal

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL13584298A 1997-10-27 1998-10-27 Use of 3-carboalkoxy-2,3-dihydro-1h-phenothiazin-4-[10h]-one derivatives for the preparation of a medicament for treating grand mal and partial seizures in a mammal IL135842A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/958,320 US5994349A (en)	1997-10-27	1997-10-27	3-carboalkoxy-2, 3-dihydro-1H-phenothiazin-4[10H]-one derivatives
PCT/US1998/022693 WO1999021560A1 (en)	1997-10-27	1998-10-27	3-carboalkoxy-2,3-dihydro-1h-phenothiazin-4[10h]-one derivatives

Publications (2)

Publication Number	Publication Date
IL135842A0 IL135842A0 (en)	2001-05-20
IL135842A true IL135842A (en)	2004-06-01

Family

ID=25500854

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13584298A IL135842A (en)	1997-10-27	1998-10-27	Use of 3-carboalkoxy-2,3-dihydro-1h-phenothiazin-4-[10h]-one derivatives for the preparation of a medicament for treating grand mal and partial seizures in a mammal

Country Status (11)

Country	Link
US (1)	US5994349A (de)
EP (1)	EP1027055B1 (de)
AT (1)	ATE257382T1 (de)
AU (1)	AU748596B2 (de)
CA (1)	CA2308281C (de)
DE (1)	DE69821019T2 (de)
DK (1)	DK1027055T3 (de)
ES (1)	ES2212370T3 (de)
IL (1)	IL135842A (de)
PT (1)	PT1027055E (de)
WO (1)	WO1999021560A1 (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW201536795A (zh)	2013-05-31	2015-10-01	Medeia Therapeutics Ltd	作為細胞保護劑用之芳基噻嗪化合物
CN106117247B (zh) *	2016-06-29	2018-02-16	东华大学	一种2‑甲基‑1,2,3,9‑四氢苯并[b]吡咯[1,4]‑噻嗪‑1,3‑二酮类化合物的制备方法
DK3846903T3 (da)	2018-09-03	2024-01-02	Hoffmann La Roche	Bicykliske heteroarylderivater
CN117946116A (zh)	2018-12-13	2024-04-30	豪夫迈·罗氏有限公司	6,7-二氢-5h-吡咯并[1,2-b][1,2,4]三唑-2-胺衍生物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3229122A1 (de) *	1982-08-04	1984-02-09	Bayer Ag, 5090 Leverkusen	Anellierte 4h-1,4-benzothiazine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3426564A1 (de) *	1984-07-19	1986-01-30	Bayer Ag, 5090 Leverkusen	Verwendung von 4h-1,4-benzothiazinen bei der prophylaxe und therapie von erkrankungen der atemwege, entzuendungen/rheuma, thromboembolischen erkrankungen, ischaemien und infarkten, herzrhythmusstoerungen, arteriosklerose und dermatosen, arzneimittel zu diesem zweck sowie wirkstoffe, die in diesen arzneimitteln enthalten sind
US5580894A (en) *	1996-01-11	1996-12-03	Howard University	Isoxazolyl enaminones

1997
- 1997-10-27 US US08/958,320 patent/US5994349A/en not_active Expired - Fee Related
1998
- 1998-10-27 EP EP98955131A patent/EP1027055B1/de not_active Expired - Lifetime
- 1998-10-27 AT AT98955131T patent/ATE257382T1/de not_active IP Right Cessation
- 1998-10-27 IL IL13584298A patent/IL135842A/en not_active IP Right Cessation
- 1998-10-27 DK DK98955131T patent/DK1027055T3/da active
- 1998-10-27 WO PCT/US1998/022693 patent/WO1999021560A1/en not_active Ceased
- 1998-10-27 CA CA002308281A patent/CA2308281C/en not_active Expired - Fee Related
- 1998-10-27 DE DE69821019T patent/DE69821019T2/de not_active Expired - Fee Related
- 1998-10-27 PT PT98955131T patent/PT1027055E/pt unknown
- 1998-10-27 ES ES98955131T patent/ES2212370T3/es not_active Expired - Lifetime
- 1998-10-27 AU AU12013/99A patent/AU748596B2/en not_active Ceased

Also Published As

Publication number	Publication date
DE69821019T2 (de)	2004-10-28
EP1027055B1 (de)	2004-01-07
US5994349A (en)	1999-11-30
CA2308281C (en)	2004-08-24
EP1027055A1 (de)	2000-08-16
IL135842A0 (en)	2001-05-20
AU1201399A (en)	1999-05-17
DE69821019D1 (en)	2004-02-12
PT1027055E (pt)	2004-05-31
CA2308281A1 (en)	1999-05-06
ATE257382T1 (de)	2004-01-15
ES2212370T3 (es)	2004-07-16
DK1027055T3 (da)	2004-04-26
AU748596B2 (en)	2002-06-06
WO1999021560A1 (en)	1999-05-06
EP1027055A4 (de)	2001-12-05

Legal Events

Date	Code	Title	Description
2004-11-10	FF	Patent granted
2009-12-24	MM9K	Patent not in force due to non-payment of renewal fees

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GB2163426A (en)	1986-02-26	Substituted quinazolinones having functionality at n1
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CA1099712A (en)	1981-04-21	Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostryrils
PL191091B1 (pl)	2006-03-31	Nowe związki indanolowe, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie
SU1438610A3 (ru)	1988-11-15	Способ получени гетероциклических соединений
JP2021104931A (ja)	2021-07-26	含窒素複素環を有するジベンゾアゼピン誘導体
HU226059B1 (en)	2008-04-28	Novel disubstituted trans-3,4,4a,5,6,10b-hexahydro-2h-naphto[1,2-b][1,4]oxazine derivatives, process for producing them and pharmaceutical compositions containing them
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EP0870759B1 (de)	2001-03-21	Aminierte 6,7,8,9-Tetrahydro-cyclopenta[a]naphthalen- und 2,3-dihydro-cyclopenta[e]inden-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
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JPH0710863B2 (ja)	1995-02-08	エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用
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