ZA200100240B - Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain. - Google Patents

Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain. Download PDF

Info

Publication number: ZA200100240B
Authority: ZA; South Africa
Prior art keywords: butyl; tetrahydropyridinyl; phenyl; hydroxy; piperdinyl
Prior art date: 1998-07-10

Application number

ZA200100240A

Other languages

English (en)

Inventor

Ramon Merce-Vidal

Jordi Frigola-Constansa

Original Assignee

Esteve Labor Dr

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.)

1998-07-10

Filing date

2001-01-09

Publication date

2001-09-03

2001-01-09 Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr

2001-09-03 Publication of ZA200100240B publication Critical patent/ZA200100240B/en

Links

208000002193 Pain Diseases 0.000 title claims description 26
230000036407 pain Effects 0.000 title claims description 15
238000011282 treatment Methods 0.000 title claims description 13
239000003814 drug Substances 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 10
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title claims description 4
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 title claims 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
208000005298 acute pain Diseases 0.000 claims description 11
-1 alkoxyl radical Chemical class 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
208000004296 neuralgia Diseases 0.000 claims description 11
208000021722 neuropathic pain Diseases 0.000 claims description 11
150000003254 radicals Chemical group 0.000 claims description 11
208000001294 Nociceptive Pain Diseases 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000000202 analgesic effect Effects 0.000 claims description 3
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 4
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 2
ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 claims 2
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims 1
KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
229940035676 analgesics Drugs 0.000 description 6
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238000002560 therapeutic procedure Methods 0.000 description 3
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
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XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 description 1
240000000233 Melia azedarach Species 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
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108050002485 Sirtuin Proteins 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
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229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
238000000291 inelastic electron tunnelling spectroscopy Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Chemical class 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
230000003387 muscular Effects 0.000 description 1
238000002402 nanowire electron scattering Methods 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
238000001320 near-infrared absorption spectroscopy Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
229960005301 pentazocine Drugs 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000004297 potassium metabisulphite Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect

Landscapes

Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)

ZA200100240A 1998-07-10 2001-01-09 Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain. ZA200100240B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES009801467A ES2151828B1 (es)	1998-07-10	1998-07-10	Empleo de derivados de tetrahidropiridinas (ohidroxi-piperidinas)-b utilazoles en la elaboracion de un medicamento para el tratamiento del dolor.

Publications (1)

Publication Number	Publication Date
ZA200100240B true ZA200100240B (en)	2001-09-03

Family

ID=8304473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200100240A ZA200100240B (en)	1998-07-10	2001-01-09	Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain.

Country Status (31)

Country	Link
US (2)	USRE39113E1 (pl)
EP (1)	EP1097698B1 (pl)
JP (1)	JP2002520261A (pl)
KR (1)	KR100758740B1 (pl)
CN (1)	CN1134259C (pl)
AR (1)	AR019894A1 (pl)
AT (1)	ATE239476T1 (pl)
AU (1)	AU747073C (pl)
BG (1)	BG64725B1 (pl)
BR (1)	BR9912000A (pl)
CA (1)	CA2336784A1 (pl)
CO (1)	CO5060468A1 (pl)
CZ (1)	CZ292015B6 (pl)
DE (1)	DE69907685T2 (pl)
DK (1)	DK1097698T3 (pl)
ES (2)	ES2151828B1 (pl)
HU (1)	HUP0102868A3 (pl)
ID (1)	ID28817A (pl)
IL (1)	IL140854A (pl)
MX (1)	MXPA01000369A (pl)
NO (1)	NO20010147L (pl)
NZ (1)	NZ509556A (pl)
PL (1)	PL194721B1 (pl)
PT (1)	PT1097698E (pl)
RU (1)	RU2202347C2 (pl)
SK (1)	SK372001A3 (pl)
TR (1)	TR200100043T2 (pl)
TW (1)	TW589317B (pl)
UA (1)	UA57149C2 (pl)
WO (1)	WO2000002519A2 (pl)
ZA (1)	ZA200100240B (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6995144B2 (en) *	2002-03-14	2006-02-07	Eisai Co., Ltd.	Nitrogen containing heterocyclic compounds and medicines containing the same
EP1481680A1 (en) *	2003-05-30	2004-12-01	Aventis Pharma Deutschland GmbH	Use of S1P
DE602004017316D1 (de)	2003-07-24	2008-12-04	Euro Celtique Sa	Heteroaryl-tetrahydropyridylverbindungen, die sich für die behandlung bzw. die prävention von schmerzen eignen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1833618A3 (ru) *	1991-01-28	1995-07-09	Институт химических наук АН Республики Казахстан	1-(3-бутоксипропил)-4-оксопиперидин в качестве промежуточного соединения в синтезе гидрохлорида 1-(3-бутоксипропил)-4-фенил-4-пропионилоксипиперидина, обладающего анальгетической активностью
JPH084287A (ja) *	1994-06-16	1996-01-09	Tateyama Alum Ind Co Ltd	柱体のコンクリート床面立設方法及びこれに用いる治具
FR2723091B1 (fr) *	1994-07-29	1996-11-08	Esteve Labor Dr	Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles
EP0906104A4 (en) *	1996-03-25	2003-12-10	Lilly Co Eli	PAIN TREATMENT PROCESS

1998
- 1998-07-10 ES ES009801467A patent/ES2151828B1/es not_active Expired - Fee Related
1999
- 1999-07-01 CO CO99041288A patent/CO5060468A1/es unknown
- 1999-07-07 AR ARP990103289A patent/AR019894A1/es unknown
- 1999-07-09 WO PCT/ES1999/000222 patent/WO2000002519A2/es not_active Ceased
- 1999-07-09 MX MXPA01000369A patent/MXPA01000369A/es active IP Right Grant
- 1999-07-09 CA CA002336784A patent/CA2336784A1/en not_active Abandoned
- 1999-07-09 BR BR9912000-3A patent/BR9912000A/pt not_active Application Discontinuation
- 1999-07-09 JP JP2000558783A patent/JP2002520261A/ja not_active Ceased
- 1999-07-09 PT PT99929333T patent/PT1097698E/pt unknown
- 1999-07-09 US US10/355,216 patent/USRE39113E1/en not_active Expired - Fee Related
- 1999-07-09 KR KR1020017000391A patent/KR100758740B1/ko not_active Expired - Fee Related
- 1999-07-09 HU HU0102868A patent/HUP0102868A3/hu unknown
- 1999-07-09 CN CNB998102083A patent/CN1134259C/zh not_active Expired - Fee Related
- 1999-07-09 TR TR2001/00043T patent/TR200100043T2/xx unknown
- 1999-07-09 EP EP99929333A patent/EP1097698B1/en not_active Expired - Lifetime
- 1999-07-09 AT AT99929333T patent/ATE239476T1/de not_active IP Right Cessation
- 1999-07-09 DE DE69907685T patent/DE69907685T2/de not_active Expired - Lifetime
- 1999-07-09 US US09/743,085 patent/US6384055B1/en not_active Ceased
- 1999-07-09 DK DK99929333T patent/DK1097698T3/da active
- 1999-07-09 IL IL140854A patent/IL140854A/en not_active IP Right Cessation
- 1999-07-09 ES ES99929333T patent/ES2198136T3/es not_active Expired - Lifetime
- 1999-07-09 AU AU46171/99A patent/AU747073C/en not_active Ceased
- 1999-07-09 NZ NZ509556A patent/NZ509556A/xx unknown
- 1999-07-09 PL PL99345781A patent/PL194721B1/pl not_active IP Right Cessation
- 1999-07-09 SK SK37-2001A patent/SK372001A3/sk unknown
- 1999-07-09 ID IDW20010066A patent/ID28817A/id unknown
- 1999-07-09 CZ CZ200175A patent/CZ292015B6/cs not_active IP Right Cessation
- 1999-07-09 RU RU2001103738/14A patent/RU2202347C2/ru not_active IP Right Cessation
- 1999-08-10 TW TW088112508A patent/TW589317B/zh not_active IP Right Cessation
- 1999-09-07 UA UA2001010210A patent/UA57149C2/uk unknown
2001
- 2001-01-09 ZA ZA200100240A patent/ZA200100240B/en unknown
- 2001-01-09 NO NO20010147A patent/NO20010147L/no not_active Application Discontinuation
- 2001-01-10 BG BG105141A patent/BG64725B1/bg unknown

Also Published As

Publication number	Publication date
BG105141A (en)	2001-10-31
DK1097698T3 (da)	2003-09-01
PL345781A1 (en)	2002-01-02
US6384055B1 (en)	2002-05-07
AR019894A1 (es)	2002-03-20
PT1097698E (pt)	2003-09-30
PL194721B1 (pl)	2007-06-29
NZ509556A (en)	2002-08-28
JP2002520261A (ja)	2002-07-09
USRE39113E1 (en)	2006-05-30
UA57149C2 (uk)	2003-06-16
AU747073C (en)	2003-06-19
CN1314814A (zh)	2001-09-26
ES2198136T3 (es)	2004-01-16
WO2000002519A3 (es)	2000-04-20
ATE239476T1 (de)	2003-05-15
ES2151828A1 (es)	2001-01-01
RU2202347C2 (ru)	2003-04-20
NO20010147D0 (no)	2001-01-09
EP1097698A2 (en)	2001-05-09
AU747073B2 (en)	2002-05-09
DE69907685T2 (de)	2004-03-11
CO5060468A1 (es)	2001-07-30
DE69907685D1 (de)	2003-06-12
WO2000002519A2 (es)	2000-01-20
BG64725B1 (bg)	2006-01-31
TW589317B (en)	2004-06-01
IL140854A (en)	2006-12-31
ID28817A (id)	2001-07-05
CZ292015B6 (cs)	2003-07-16
ES2151828B1 (es)	2001-08-16
CZ200175A3 (cs)	2001-07-11
CN1134259C (zh)	2004-01-14
HUP0102868A2 (hu)	2001-12-28
MXPA01000369A (es)	2003-06-19
TR200100043T2 (tr)	2001-09-21
SK372001A3 (en)	2001-10-08
EP1097698B1 (en)	2003-05-07
HUP0102868A3 (en)	2003-01-28
KR100758740B1 (ko)	2007-09-14
IL140854A0 (en)	2003-09-17
BR9912000A (pt)	2001-05-29
AU4617199A (en)	2000-02-01
KR20010071824A (ko)	2001-07-31
CA2336784A1 (en)	2000-01-20
NO20010147L (no)	2001-01-09

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KR960704884A (ko)	1996-10-09	항종양제 또는 항바이러스제로서의 디스타마이신 A 동족체 (Distamycin A analogues as antitumour or antiviral agents)
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PH27002A (en)	1993-02-01	New use of 5HT antagonists
MXPA03005284A (es)	2003-09-25	Nuevo procedimiento para la sintesis de fenilamida del acido 5-(4-flourofenil) -1-[2-((2r, 4r)-4-hidroxi -6-oxotetrahidro -piran-2-il) -etil]-2-isopropil -4-fenil-1h -pirrol-3-carboxilico.
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WO2003008407A3 (fr)	2003-10-16	Derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique
BRPI0413233A (pt)	2006-10-03	novos compostos
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ZA200100240B (en)	2001-09-03	Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain.
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CA2101581A1 (en)	1994-01-31	1-aminoacetamidopyrroles and 1-amino acetamido-2-(substituted) pyrroles and related compounds
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JP2004525184A5 (pl)	2005-12-22
DK0785789T3 (da)	2003-01-20	Diazepinindoler som phosphodiesterase IV-inhibitorer
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