SK9402002A3 - Novel substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them - Google Patents

Novel substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them Download PDF

Info

Publication number: SK9402002A3
Authority: SK; Slovakia
Prior art keywords: pyrazolo; diazepin; ethyl; dihydrogen; ppm
Prior art date: 2000-01-05

Application number

SK940-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Catherine Burnouf

Amaya Berecibar

Michel Navet

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.)

2000-01-05

Filing date

2000-12-27

Publication date

2003-08-05

2000-12-27 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2003-08-05 Publication of SK9402002A3 publication Critical patent/SK9402002A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 41
229940126601 medicinal product Drugs 0.000 title claims abstract description 11
239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 6
230000008569 process Effects 0.000 title abstract description 11
CRHOJTLKLUQJSM-UHFFFAOYSA-N pyrazolo[3,4-d]diazepine Chemical class C1=NN=CC=C2C=NN=C21 CRHOJTLKLUQJSM-UHFFFAOYSA-N 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 216
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 640
125000004432 carbon atom Chemical group C* 0.000 claims description 200
-1 methoxy, hydroxy Chemical group 0.000 claims description 140
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 138
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 117
229910052757 nitrogen Inorganic materials 0.000 claims description 115
229910052717 sulfur Chemical group 0.000 claims description 108
229910052760 oxygen Inorganic materials 0.000 claims description 102
125000005842 heteroatom Chemical group 0.000 claims description 81
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 78
239000001301 oxygen Chemical group 0.000 claims description 78
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 77
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 77
239000011593 sulfur Chemical group 0.000 claims description 77
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 74
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
125000003118 aryl group Chemical group 0.000 claims description 53
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
125000000753 cycloalkyl group Chemical group 0.000 claims description 50
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 35
125000002877 alkyl aryl group Chemical group 0.000 claims description 34
125000003710 aryl alkyl group Chemical group 0.000 claims description 26
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229910052799 carbon Inorganic materials 0.000 claims description 25
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125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 18
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 12
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
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208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
208000011580 syndromic disease Diseases 0.000 claims description 8
229910052721 tungsten Inorganic materials 0.000 claims description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 7
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 7
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125000003545 alkoxy group Chemical group 0.000 claims description 7
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
230000001684 chronic effect Effects 0.000 claims description 6
230000006378 damage Effects 0.000 claims description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
230000035882 stress Effects 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
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125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
AVRKSHFWKBNKBU-UHFFFAOYSA-N CCOC(=O)C1=CNC=CC=N1 Chemical compound CCOC(=O)C1=CNC=CC=N1 AVRKSHFWKBNKBU-UHFFFAOYSA-N 0.000 claims description 4
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BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
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125000001153 fluoro group Chemical group F* 0.000 claims description 3
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238000002560 therapeutic procedure Methods 0.000 claims description 3
238000007280 thionation reaction Methods 0.000 claims description 3
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
206010012438 Dermatitis atopic Diseases 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims description 2
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 2
201000008937 atopic dermatitis Diseases 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
230000004968 inflammatory condition Effects 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
MKDKOPTXADLFIA-UHFFFAOYSA-N 1-ethyl-3-methyl-5-(4-methylphenyl)-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound C1NC(=O)C=2N(CC)N=C(C)C=2N=C1C1=CC=C(C)C=C1 MKDKOPTXADLFIA-UHFFFAOYSA-N 0.000 claims 1
KGEMKXWIIXCPCB-UHFFFAOYSA-N 1-ethyl-3-propan-2-yl-5-[4-(trifluoromethyl)phenyl]-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound C1NC(=O)C=2N(CC)N=C(C(C)C)C=2N=C1C1=CC=C(C(F)(F)F)C=C1 KGEMKXWIIXCPCB-UHFFFAOYSA-N 0.000 claims 1
OETSJRZSRPIUJQ-UHFFFAOYSA-N 3,5-ditert-butyl-1-ethyl-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound N1=C(C(C)(C)C)CNC(=O)C2=C1C(C(C)(C)C)=NN2CC OETSJRZSRPIUJQ-UHFFFAOYSA-N 0.000 claims 1
FMDWGNQQWFTIQP-UHFFFAOYSA-N 3-tert-butyl-1-ethyl-5-(4-hydroxyphenyl)-6,7-dihydropyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound C1NC(=O)C=2N(CC)N=C(C(C)(C)C)C=2N=C1C1=CC=C(O)C=C1 FMDWGNQQWFTIQP-UHFFFAOYSA-N 0.000 claims 1
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XZQJNUKCAVEBHU-UHFFFAOYSA-N 2-ethyl-5-methyl-4-nitropyrazole-3-carboxylic acid Chemical compound CCN1N=C(C)C([N+]([O-])=O)=C1C(O)=O XZQJNUKCAVEBHU-UHFFFAOYSA-N 0.000 description 20
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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SK940-2002A 2000-01-05 2000-12-27 Novel substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them SK9402002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0000095A FR2803299B1 (fr)	2000-01-05	2000-01-05	NOUVELLES PYRAZOLO [4,3-e] DIAZEPINES SUBSTITUEES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, UTILISATION A TITRE DE MEDICAMENT ET PROCEDES POUR LEUR PREPARATION
PCT/EP2000/013380 WO2001049689A2 (en)	2000-01-05	2000-12-27	NOVEL SUBSTITUTED PYRAZOLO[4,3-e]DIAZEPINES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, USE AS MEDICINAL PRODUCTS AND PROCESSES FOR PREPARING THEM

Publications (1)

Publication Number	Publication Date
SK9402002A3 true SK9402002A3 (en)	2003-08-05

Family

ID=8845641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK940-2002A SK9402002A3 (en)	2000-01-05	2000-12-27	Novel substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them

Country Status (42)

Country	Link
EP (1)	EP1248787B1 (tr)
JP (1)	JP2003519233A (tr)
KR (1)	KR20020063293A (tr)
CN (1)	CN1420888A (tr)
AP (1)	AP2002002572A0 (tr)
AR (1)	AR032298A1 (tr)
AT (1)	ATE278692T1 (tr)
AU (1)	AU3367801A (tr)
BG (1)	BG106893A (tr)
BR (1)	BR0016926A (tr)
CA (1)	CA2396315A1 (tr)
CO (1)	CO5290255A1 (tr)
CR (1)	CR6693A (tr)
CZ (1)	CZ20022222A3 (tr)
DE (1)	DE60014712T2 (tr)
DZ (1)	DZ3103A1 (tr)
EA (1)	EA005071B1 (tr)
EE (1)	EE200200373A (tr)
ES (1)	ES2226978T3 (tr)
FR (1)	FR2803299B1 (tr)
GT (1)	GT200100002A (tr)
HK (1)	HK1050002A1 (tr)
HN (1)	HN2001000002A (tr)
HR (1)	HRP20020577A2 (tr)
HU (1)	HUP0204213A2 (tr)
IL (1)	IL150394A0 (tr)
IS (1)	IS6437A (tr)
MA (1)	MA26863A1 (tr)
MX (1)	MXPA02006618A (tr)
NO (1)	NO20023249L (tr)
NZ (1)	NZ519520A (tr)
OA (1)	OA12134A (tr)
PA (1)	PA8509601A1 (tr)
PE (1)	PE20011041A1 (tr)
PL (1)	PL356668A1 (tr)
SK (1)	SK9402002A3 (tr)
SV (1)	SV2001000253A (tr)
TN (1)	TNSN01001A1 (tr)
TR (1)	TR200201719T2 (tr)
UY (1)	UY26517A1 (tr)
WO (1)	WO2001049689A2 (tr)
ZA (1)	ZA200205287B (tr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1188438A1 (en) *	2000-09-15	2002-03-20	Warner-Lambert Company	Pharmaceutical composition for preventing or treating a disease associated with an excess of Il-12 production
EP1199074A1 (en) *	2000-09-15	2002-04-24	Warner-Lambert Company	Pharmaceutical composition for preventing or treating a disease associated with an excess of il-12 production
TW200745106A (en) *	2005-10-03	2007-12-16	Astrazeneca Ab	Chemical compounds
KR20160080799A (ko)	2014-12-30	2016-07-08	한국해양과학기술원	금 촉매를 이용한 α-피론 유도체 전합성 방법 및 이에 의해 합성되어 인간 암세포주에 세포독성을 가지는 α-피론 유도체
EP3551632B1 (en) *	2016-12-12	2024-06-12	UNION therapeutics A/S	Substituted pyrazoloazepin-4-ones and their use as phosphodiesterase inhibitors
WO2018108231A1 (en)	2016-12-12	2018-06-21	Leo Pharma A/S	Substituted pyrazoloazepin-8-ones and their use as phosphodiesterase inhibitors
JP6850886B2 (ja)	2016-12-12	2021-03-31	レオファーマアクティーゼルスカブ	置換ピラゾロアゼピン−４−オンおよびそれらのホスホジエステラーゼ阻害剤としての使用
TWI812739B (zh) *	2018-06-21	2023-08-21	景凱生物科技股份有限公司	Nadph氧化酶抑制劑、含其的醫藥組合物、及其應用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3764688A (en) *	1972-07-27	1973-10-09	Abbott Lab	4,6-DIHYDRO-1,3-DIMETHYL-8-PHENYL-4-PROPARGYL-PYRAZOLO {8 4,3-e{9 {0 DIAZEPIN-5 (1H) ONE IN TREATING INFLAMMATION

2000
- 2000-01-05 FR FR0000095A patent/FR2803299B1/fr not_active Expired - Fee Related
- 2000-12-23 DZ DZ000158A patent/DZ3103A1/xx active
- 2000-12-27 TR TR2002/01719T patent/TR200201719T2/tr unknown
- 2000-12-27 HR HR20020577A patent/HRP20020577A2/hr not_active Application Discontinuation
- 2000-12-27 JP JP2001550229A patent/JP2003519233A/ja active Pending
- 2000-12-27 HU HU0204213A patent/HUP0204213A2/hu unknown
- 2000-12-27 AP APAP/P/2002/002572A patent/AP2002002572A0/en unknown
- 2000-12-27 SK SK940-2002A patent/SK9402002A3/sk unknown
- 2000-12-27 OA OA1200200203A patent/OA12134A/en unknown
- 2000-12-27 EE EEP200200373A patent/EE200200373A/xx unknown
- 2000-12-27 MX MXPA02006618A patent/MXPA02006618A/es active IP Right Grant
- 2000-12-27 ES ES00991657T patent/ES2226978T3/es not_active Expired - Lifetime
- 2000-12-27 AT AT00991657T patent/ATE278692T1/de not_active IP Right Cessation
- 2000-12-27 DE DE60014712T patent/DE60014712T2/de not_active Expired - Fee Related
- 2000-12-27 BR BR0016926-9A patent/BR0016926A/pt not_active Application Discontinuation
- 2000-12-27 AU AU33678/01A patent/AU3367801A/en not_active Abandoned
- 2000-12-27 NZ NZ519520A patent/NZ519520A/en unknown
- 2000-12-27 PL PL00356668A patent/PL356668A1/xx not_active Application Discontinuation
- 2000-12-27 CZ CZ20022222A patent/CZ20022222A3/cs unknown
- 2000-12-27 WO PCT/EP2000/013380 patent/WO2001049689A2/en not_active Ceased
- 2000-12-27 CN CN00818202A patent/CN1420888A/zh active Pending
- 2000-12-27 HK HK03102129.7A patent/HK1050002A1/zh unknown
- 2000-12-27 IL IL15039400A patent/IL150394A0/xx unknown
- 2000-12-27 EP EP00991657A patent/EP1248787B1/en not_active Expired - Lifetime
- 2000-12-27 KR KR1020027008692A patent/KR20020063293A/ko not_active Withdrawn
- 2000-12-27 EA EA200200610A patent/EA005071B1/ru not_active IP Right Cessation
- 2000-12-27 CA CA002396315A patent/CA2396315A1/en not_active Abandoned
2001
- 2001-01-03 PA PA20018509601A patent/PA8509601A1/es unknown
- 2001-01-03 TN TNTNSN01001A patent/TNSN01001A1/fr unknown
- 2001-01-03 UY UY26517A patent/UY26517A1/es not_active Application Discontinuation
- 2001-01-03 AR ARP010100024A patent/AR032298A1/es not_active Application Discontinuation
- 2001-01-03 PE PE2001000003A patent/PE20011041A1/es not_active Application Discontinuation
- 2001-01-04 SV SV2001000253A patent/SV2001000253A/es not_active Application Discontinuation
- 2001-01-04 HN HN2001000002A patent/HN2001000002A/es unknown
- 2001-01-04 GT GT200100002A patent/GT200100002A/es unknown
- 2001-01-04 CO CO01000514A patent/CO5290255A1/es not_active Application Discontinuation
2002
- 2002-06-19 IS IS6437A patent/IS6437A/is unknown
- 2002-07-01 CR CR6693A patent/CR6693A/es not_active Application Discontinuation
- 2002-07-02 ZA ZA200205287A patent/ZA200205287B/en unknown
- 2002-07-02 BG BG106893A patent/BG106893A/xx unknown
- 2002-07-03 MA MA26719A patent/MA26863A1/fr unknown
- 2002-07-04 NO NO20023249A patent/NO20023249L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HK1050002A1 (zh)	2003-06-06
EE200200373A (et)	2003-10-15
IL150394A0 (en)	2002-12-01
WO2001049689A2 (en)	2001-07-12
PA8509601A1 (es)	2002-07-30
IS6437A (is)	2002-06-19
ES2226978T3 (es)	2005-04-01
GT200100002A (es)	2002-01-18
PE20011041A1 (es)	2001-10-12
DZ3103A1 (fr)	2004-06-20
EP1248787A2 (en)	2002-10-16
EA200200610A1 (ru)	2002-12-26
AP2002002572A0 (en)	2002-09-30
CR6693A (es)	2004-04-27
UY26517A1 (es)	2001-03-16
HRP20020577A2 (en)	2003-12-31
TNSN01001A1 (fr)	2005-11-10
NO20023249L (no)	2002-09-04
CA2396315A1 (en)	2001-07-12
EA005071B1 (ru)	2004-10-28
PL356668A1 (en)	2004-06-28
HUP0204213A2 (hu)	2003-04-28
KR20020063293A (ko)	2002-08-01
DE60014712D1 (de)	2004-11-11
OA12134A (en)	2006-05-05
CO5290255A1 (es)	2003-06-27
BG106893A (en)	2003-04-30
FR2803299B1 (fr)	2004-09-17
AR032298A1 (es)	2003-11-05
WO2001049689A3 (en)	2001-12-20
ZA200205287B (en)	2003-07-02
SV2001000253A (es)	2001-10-16
CZ20022222A3 (cs)	2003-05-14
JP2003519233A (ja)	2003-06-17
HN2001000002A (es)	2001-09-26
FR2803299A1 (fr)	2001-07-06
ATE278692T1 (de)	2004-10-15
NZ519520A (en)	2004-02-27
BR0016926A (pt)	2002-11-19
MXPA02006618A (es)	2002-09-30
DE60014712T2 (de)	2006-02-02
CN1420888A (zh)	2003-05-28
NO20023249D0 (no)	2002-07-04
MA26863A1 (fr)	2004-12-20
AU3367801A (en)	2001-07-16
EP1248787B1 (en)	2004-10-06
TR200201719T2 (tr)	2002-12-23

Legal Events

Date	Code	Title	Description
2010-03-08	FB9A	Suspension of patent application procedure

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CN114656472B (zh)	2023-07-04	吡唑并嘧啶类化合物、异构体或盐及其制备方法和用途
JP2000507552A (ja)	2000-06-20	アリールオキシおよびアリールチオ縮合ピリジン、アリールオキシおよびアリールチオ縮合ピリミジン、およびそれらの誘導体
US4897392A (en)	1990-01-30	4H-indolo(1,2-d)(1,2,4)triazolo(4,3-A)(1,4)benzodiazepines
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US6962912B2 (en)	2005-11-08	Substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them
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JP2000038389A (ja)	2000-02-08	ピラゾロピリミジン化合物及びキサンチンオキシダーゼ阻害剤
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