JPH11508902A - 新規キノキサリン−およびキノキサリンアルカン−ホスホン酸 - Google Patents

新規キノキサリン−およびキノキサリンアルカン−ホスホン酸

Info

Publication number: JPH11508902A
Authority: JP; Japan
Prior art keywords: acid; dioxo; tetrahydro; free; group
Prior art date: 1995-07-10
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

JP9505465A

Other languages

English (en)

Japanese (ja)

Inventor

モレッティ，ロベール

アルガイアー，ハンス

Original Assignee

ノバルティス・アクチエンゲゼルシャフト

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.)

1995-07-10

Filing date

1996-07-01

Publication date

1999-08-03

1996-07-01 Application filed by ノバルティス・アクチエンゲゼルシャフト filed Critical ノバルティス・アクチエンゲゼルシャフト

1999-08-03 Publication of JPH11508902A publication Critical patent/JPH11508902A/ja

Status Pending legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 claims abstract description 53
239000001257 hydrogen Substances 0.000 claims abstract description 38
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
229910052736 halogen Inorganic materials 0.000 claims abstract description 23
150000002367 halogens Chemical class 0.000 claims abstract description 23
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims abstract description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims abstract description 6
230000001575 pathological effect Effects 0.000 claims abstract description 3
-1 nitro, carboxy Chemical group 0.000 claims description 133
150000001875 compounds Chemical class 0.000 claims description 93
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000001118 alkylidene group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
208000005392 Spasm Diseases 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
QIKGBPGSUJXLBC-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CCCP(O)(=O)O QIKGBPGSUJXLBC-UHFFFAOYSA-N 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000005109 alkynylthio group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
206010010904 Convulsion Diseases 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
125000005108 alkenylthio group Chemical group 0.000 claims description 3
230000036461 convulsion Effects 0.000 claims description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 claims description 3
GZDJSOJULKHOIW-UHFFFAOYSA-N 1-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C(C)P(O)(O)=O GZDJSOJULKHOIW-UHFFFAOYSA-N 0.000 claims description 2
KLCJLGDHDKNRFF-UHFFFAOYSA-N 1-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C(C)P(O)(O)=O KLCJLGDHDKNRFF-UHFFFAOYSA-N 0.000 claims description 2
BABPOUFHWOCNNS-UHFFFAOYSA-N 2-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CP(O)(=O)O BABPOUFHWOCNNS-UHFFFAOYSA-N 0.000 claims description 2
OCFXRQBTOUGKRB-UHFFFAOYSA-N 2-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCP(O)(=O)O OCFXRQBTOUGKRB-UHFFFAOYSA-N 0.000 claims description 2
ZQBFDFCRRKCWPN-UHFFFAOYSA-N 2-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C=CP(O)(=O)O ZQBFDFCRRKCWPN-UHFFFAOYSA-N 0.000 claims description 2
CXGBVHWGXKKZTM-UHFFFAOYSA-N 2-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCP(O)(=O)O CXGBVHWGXKKZTM-UHFFFAOYSA-N 0.000 claims description 2
RMDXKUMEYLOUJB-UHFFFAOYSA-N 3-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CCP(O)(=O)O RMDXKUMEYLOUJB-UHFFFAOYSA-N 0.000 claims description 2
IRMAUQFNMCPNKR-UHFFFAOYSA-N 3-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)propylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCCP(O)(=O)O IRMAUQFNMCPNKR-UHFFFAOYSA-N 0.000 claims description 2
PZKZUTUIEQATQD-UHFFFAOYSA-N 3-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C=CCP(O)(=O)O PZKZUTUIEQATQD-UHFFFAOYSA-N 0.000 claims description 2
UWZRCGOFRIWUQT-UHFFFAOYSA-N 3-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)propylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCCP(O)(=O)O UWZRCGOFRIWUQT-UHFFFAOYSA-N 0.000 claims description 2
OARFPQNKOLGYHZ-UHFFFAOYSA-N 3-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound ClC1=CC(=C2NC(C(NC2=C1)=O)=O)C=CCP(O)(=O)O OARFPQNKOLGYHZ-UHFFFAOYSA-N 0.000 claims description 2
DIWCSSZWIWIHJC-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCC=CP(O)(=O)O DIWCSSZWIWIHJC-UHFFFAOYSA-N 0.000 claims description 2
WTGPQJYRMFTPLH-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCCCP(O)(=O)O WTGPQJYRMFTPLH-UHFFFAOYSA-N 0.000 claims description 2
GHZGLYPWKLGARA-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCC=CP(O)(=O)O GHZGLYPWKLGARA-UHFFFAOYSA-N 0.000 claims description 2
BFXXCDKGBWJVRM-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C=CCCP(O)(=O)O BFXXCDKGBWJVRM-UHFFFAOYSA-N 0.000 claims description 2
UCOYQIJKIGUGSB-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCC=CP(O)(=O)O UCOYQIJKIGUGSB-UHFFFAOYSA-N 0.000 claims description 2
MQGNUGIYISGXJZ-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C=CCCP(O)(=O)O MQGNUGIYISGXJZ-UHFFFAOYSA-N 0.000 claims description 2
201000006474 Brain Ischemia Diseases 0.000 claims description 2
206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
206010047163 Vasospasm Diseases 0.000 claims description 2
206010008118 cerebral infarction Diseases 0.000 claims description 2
206010015037 epilepsy Diseases 0.000 claims description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
230000002792 vascular Effects 0.000 claims description 2
241000506319 Trifur Species 0.000 claims 2
208000023589 ischemic disease Diseases 0.000 claims 2
AVMVKAVAFKFBNZ-UHFFFAOYSA-N 1-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C(C)P(O)(O)=O AVMVKAVAFKFBNZ-UHFFFAOYSA-N 0.000 claims 1
QNQPLCIZACNUQH-UHFFFAOYSA-N 2-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound OP(O)(=O)C=Cc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12 QNQPLCIZACNUQH-UHFFFAOYSA-N 0.000 claims 1
IMIQAHTWYJCSJN-UHFFFAOYSA-N 2-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCP(O)(=O)O IMIQAHTWYJCSJN-UHFFFAOYSA-N 0.000 claims 1
WZMNUVQQLLZLDG-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCCCP(O)(=O)O WZMNUVQQLLZLDG-UHFFFAOYSA-N 0.000 claims 1
BJZGWDAAMWNEPG-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCCCP(O)(=O)O BJZGWDAAMWNEPG-UHFFFAOYSA-N 0.000 claims 1
229940124531 pharmaceutical excipient Drugs 0.000 claims 1
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230000001225 therapeutic effect Effects 0.000 claims 1
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150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
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238000006243 chemical reaction Methods 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 13
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
239000007858 starting material Substances 0.000 description 10
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238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
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238000005160 1H NMR spectroscopy Methods 0.000 description 7
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108010010803 Gelatin Proteins 0.000 description 7
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OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
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CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 to carbon atoms of the hetero ring

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Health & Medical Sciences (AREA)
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Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP9505465A 1995-07-10 1996-07-01 新規キノキサリン−およびキノキサリンアルカン−ホスホン酸 Pending JPH11508902A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH2009/95		1995-07-10
CH200995		1995-07-10
PCT/EP1996/002866 WO1997003079A1 (en)	1995-07-10	1996-07-01	Novel quinoxaline- and quinoxalinylalkane-phosphonic acids

Publications (1)

Publication Number	Publication Date
JPH11508902A true JPH11508902A (ja)	1999-08-03

Family

ID=4223780

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9505465A Pending JPH11508902A (ja)	1995-07-10	1996-07-01	新規キノキサリン−およびキノキサリンアルカン−ホスホン酸

Country Status (15)

Country	Link
EP (1)	EP0837864A1 (cs)
JP (1)	JPH11508902A (cs)
KR (1)	KR19990028839A (cs)
AU (1)	AU6516296A (cs)
BR (1)	BR9609644A (cs)
CA (1)	CA2224718A1 (cs)
CZ (1)	CZ5398A3 (cs)
HU (1)	HUP9901345A3 (cs)
IL (1)	IL122872A0 (cs)
NO (1)	NO980095L (cs)
PL (1)	PL324340A1 (cs)
SK (1)	SK2798A3 (cs)
TR (1)	TR199800022T1 (cs)
WO (1)	WO1997003079A1 (cs)
ZA (1)	ZA965800B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TR199900897T2 (xx) *	1996-10-24	1999-07-21	Novartis Ag	Ornat�lm�� aminoalkanfosfonik asitler.
US6841684B2 (en)	1997-12-04	2005-01-11	Allergan, Inc.	Imidiazoles having reduced side effects
US6329369B1 (en)	1997-12-04	2001-12-11	Allergan Sales, Inc.	Methods of treating pain and other conditions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5118675A (en) *	1991-02-15	1992-06-02	American Home Products Corporation	Quinoxaline phosphono-amino acids
IL109397A0 (en) *	1993-04-28	1994-07-31	Schering Ag	Quinoxalinedione derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same

1996
- 1996-07-01 HU HU9901345A patent/HUP9901345A3/hu unknown
- 1996-07-01 TR TR1998/00022T patent/TR199800022T1/xx unknown
- 1996-07-01 SK SK27-98A patent/SK2798A3/sk unknown
- 1996-07-01 JP JP9505465A patent/JPH11508902A/ja active Pending
- 1996-07-01 WO PCT/EP1996/002866 patent/WO1997003079A1/en not_active Ceased
- 1996-07-01 AU AU65162/96A patent/AU6516296A/en not_active Abandoned
- 1996-07-01 PL PL96324340A patent/PL324340A1/xx unknown
- 1996-07-01 EP EP96924829A patent/EP0837864A1/en not_active Withdrawn
- 1996-07-01 BR BR9609644A patent/BR9609644A/pt not_active Application Discontinuation
- 1996-07-01 IL IL12287296A patent/IL122872A0/xx unknown
- 1996-07-01 CZ CZ9853A patent/CZ5398A3/cs unknown
- 1996-07-01 CA CA002224718A patent/CA2224718A1/en not_active Abandoned
- 1996-07-01 KR KR1019980700140A patent/KR19990028839A/ko not_active Withdrawn
- 1996-07-09 ZA ZA965800A patent/ZA965800B/xx unknown
1998
- 1998-01-09 NO NO980095A patent/NO980095L/no unknown

Also Published As

Publication number	Publication date
ZA965800B (en)	1997-01-10
AU6516296A (en)	1997-02-10
PL324340A1 (en)	1998-05-25
BR9609644A (pt)	1999-05-11
MX9800332A (es)	1998-07-31
SK2798A3 (en)	1998-07-08
HUP9901345A3 (en)	2000-01-28
TR199800022T1 (xx)	1998-05-21
CA2224718A1 (en)	1997-01-30
NO980095L (no)	1998-03-05
HUP9901345A2 (hu)	1999-08-30
NO980095D0 (no)	1998-01-09
WO1997003079A1 (en)	1997-01-30
EP0837864A1 (en)	1998-04-29
CZ5398A3 (cs)	1998-06-17
KR19990028839A (ko)	1999-04-15
IL122872A0 (en)	1998-08-16

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KR19990077135A (ko)	1999-10-25	5에이치, 10에이치-이미다조[1,2-에이]인데노[1,2-이]피라진-4-온 유도체, 이의 제조방법, 이의 중간체 및 이를 함유하는 약제
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KR20010082702A (ko)	2001-08-30	6-아미노 또는 6-히드라지노-술포닐-3-퀴놀릴-포스폰산화합물, 이의 제조 방법 및 이를 함유하는 약제 조성물
JPH0873465A (ja)	1996-03-19	アザ脂肪族架橋キノキサリン−２，３−ジオン
JP2001278890A (ja)	2001-10-10	アリール又はヘテロアリールキノリニルホスホン酸化合物、これらの製造方法及びこれらを含む薬剤組成物
JP2926274B2 (ja)	1999-07-28	ホスホン酸ジエステル誘導体
KR100807894B1 (ko)	2008-02-27	포스핀산 유도체
JPH0555510B2 (cs)	1993-08-17
JP2001253892A (ja)	2001-09-18	６−スルファモイル−３−キノリルホスホン酸化合物、これらの製造方法及びこれらを含む薬剤組成物
CN1194649A (zh)	1998-09-30	新的喹喔啉－和喹喔啉基烷烃－膦酸
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CA2073464A1 (en)	1991-07-14	Anxiolytic drugs
JPWO1991010432A1 (ja)	1992-01-09	抗不安薬