FI112472B - Menetelmä terapeuttisesti aktiivisten substituoitujen atsaheterosyklikarboksyylihappojen valmistamiseksi - Google Patents

Menetelmä terapeuttisesti aktiivisten substituoitujen atsaheterosyklikarboksyylihappojen valmistamiseksi Download PDF

Info

Publication number: FI112472B
Authority: FI; Finland
Prior art keywords: mmol; amino; solution; mixture; vacuo
Prior art date: 1993-09-17

Application number

FI961239A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI961239A0 (fi

FI961239A7 (fi

Inventor

Masami Nakane

Masaya Ikunaka

Yuuji Shishido

Original Assignee

Pfizer

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.)

1993-09-17

Filing date

1996-03-15

Publication date

2003-12-15

1996-03-15 Application filed by Pfizer filed Critical Pfizer

1996-03-15 Publication of FI961239A0 publication Critical patent/FI961239A0/fi

1996-03-15 Publication of FI961239A7 publication Critical patent/FI961239A7/fi

2003-12-15 Application granted granted Critical

2003-12-15 Publication of FI112472B publication Critical patent/FI112472B/fi

Links

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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 29
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239000001257 hydrogen Substances 0.000 claims abstract description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
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VDQQJMHXZCMNMU-UHFFFAOYSA-N 1-phenylpyrrolidine Chemical compound C1CCCN1C1=CC=CC=C1 VDQQJMHXZCMNMU-UHFFFAOYSA-N 0.000 claims description 2
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LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 1
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
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239000008273 gelatin Substances 0.000 description 1
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235000010299 hexamethylene tetramine Nutrition 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
239000012372 hydroboration reagent Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
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230000007365 immunoregulation Effects 0.000 description 1
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229910010272 inorganic material Inorganic materials 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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235000019359 magnesium stearate 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
239000000463 material Substances 0.000 description 1
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GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
UOLGPBIBWUMXNA-VMPITWQZSA-N methyl (e)-4-phenylmethoxybut-2-enoate Chemical compound COC(=O)\C=C\COCC1=CC=CC=C1 UOLGPBIBWUMXNA-VMPITWQZSA-N 0.000 description 1
FADYCRUUTHJNDY-UHFFFAOYSA-N methyl 2-phenylpyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCCC1C1=CC=CC=C1 FADYCRUUTHJNDY-UHFFFAOYSA-N 0.000 description 1
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LFMTUFVYMCDPGY-UHFFFAOYSA-N n,n-diethylethanamine oxide Chemical compound CC[N+]([O-])(CC)CC LFMTUFVYMCDPGY-UHFFFAOYSA-N 0.000 description 1
XEWVCDMEDQYCHX-UHFFFAOYSA-N n,n-diethylethanamine;hydron;iodide Chemical compound [I-].CC[NH+](CC)CC XEWVCDMEDQYCHX-UHFFFAOYSA-N 0.000 description 1
ZIWFCOIGUNPHPM-UHFFFAOYSA-N n-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=C(OC(F)(F)F)C=C1CNC1C(C=2C=CC=CC=2)NCCC1 ZIWFCOIGUNPHPM-UHFFFAOYSA-N 0.000 description 1
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PMQNLFGGVGXOSM-QRQUECDASA-N nff 2 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCNC=1C(=CC(=CC=1)[N+]([O-])=O)[N+]([O-])=O)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)C(CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)CC=1C=2C=CC(OC)=CC=2OC(=O)C=1)C1=CC=C(O)C=C1 PMQNLFGGVGXOSM-QRQUECDASA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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238000006709 oxidative esterification reaction Methods 0.000 description 1
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239000000312 peanut oil Substances 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
229940074439 potassium sodium tartrate Drugs 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003410 quininyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 1
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239000000523 sample Substances 0.000 description 1
201000000980 schizophrenia Diseases 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
230000009758 senescence Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/22—Anxiolytics
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

FI961239A 1993-09-17 1996-03-15 Menetelmä terapeuttisesti aktiivisten substituoitujen atsaheterosyklikarboksyylihappojen valmistamiseksi FI112472B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP25506493		1993-09-17
JP25506493		1993-09-17
JP9401514		1994-09-13
PCT/JP1994/001514 WO1995007886A1 (en)	1993-09-17	1994-09-13	3-amino-5-carboxy-substituted piperidines and 3-amino-4-carboxy-substituted pyrrolidines as tachykinin antagonists

Publications (3)

Publication Number	Publication Date
FI961239A0 FI961239A0 (fi)	1996-03-15
FI961239A7 FI961239A7 (fi)	1996-03-15
FI112472B true FI112472B (fi)	2003-12-15

Family

ID=17273646

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI961239A FI112472B (fi)	1993-09-17	1996-03-15	Menetelmä terapeuttisesti aktiivisten substituoitujen atsaheterosyklikarboksyylihappojen valmistamiseksi

Country Status (9)

Country	Link
EP (1)	EP0719253B1 (de)
AT (1)	ATE265432T1 (de)
CA (1)	CA2171637C (de)
DE (1)	DE69433744T2 (de)
DK (1)	DK0719253T3 (de)
ES (1)	ES2217269T3 (de)
FI (1)	FI112472B (de)
PT (1)	PT719253E (de)
WO (1)	WO1995007886A1 (de)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH10508837A (ja) *	1994-11-10	1998-09-02	ファイザー・インコーポレーテッド	眼の疾患を治療するためのｎｋ−１レセプターアンタゴニスト
IT1292426B1 (it) *	1997-06-27	1999-02-08	Nicox Sa	Sali nitrati di ace-inibitori
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1994
- 1994-09-13 ES ES94926394T patent/ES2217269T3/es not_active Expired - Lifetime
- 1994-09-13 AT AT94926394T patent/ATE265432T1/de not_active IP Right Cessation
- 1994-09-13 DK DK94926394T patent/DK0719253T3/da active
- 1994-09-13 CA CA002171637A patent/CA2171637C/en not_active Expired - Fee Related
- 1994-09-13 WO PCT/JP1994/001514 patent/WO1995007886A1/en not_active Ceased
- 1994-09-13 DE DE69433744T patent/DE69433744T2/de not_active Expired - Fee Related
- 1994-09-13 PT PT94926394T patent/PT719253E/pt unknown
- 1994-09-13 EP EP94926394A patent/EP0719253B1/de not_active Expired - Lifetime
1996
- 1996-03-15 FI FI961239A patent/FI112472B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT719253E (pt)	2004-07-30
EP0719253A1 (de)	1996-07-03
WO1995007886A1 (en)	1995-03-23
CA2171637A1 (en)	1995-03-23
FI961239A0 (fi)	1996-03-15
ES2217269T3 (es)	2004-11-01
DE69433744D1 (de)	2004-06-03
CA2171637C (en)	2000-05-23
EP0719253B1 (de)	2004-04-28
FI961239A7 (fi)	1996-03-15
DE69433744T2 (de)	2004-10-14
DK0719253T3 (da)	2004-07-26
ATE265432T1 (de)	2004-05-15

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