FI72316C - Foerfarande foer framstaellning av farmaceutiskt aktiva n2-arylsulfonyl-l-argininamider och farmaceutiskt acceptabla salter daerav. - Google Patents
Foerfarande foer framstaellning av farmaceutiskt aktiva n2-arylsulfonyl-l-argininamider och farmaceutiskt acceptabla salter daerav. Download PDFInfo
- Publication number
- FI72316C FI72316C FI780073A FI780073A FI72316C FI 72316 C FI72316 C FI 72316C FI 780073 A FI780073 A FI 780073A FI 780073 A FI780073 A FI 780073A FI 72316 C FI72316 C FI 72316C
- Authority
- FI
- Finland
- Prior art keywords
- arylsulfonyl
- substituted
- group
- acid
- formula
- Prior art date
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- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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 Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical class OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005583 trifluoroacetylation reaction Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005866 tritylation reaction Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 239000004066 vascular targeting agent Substances 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI842539A FI74455C (fi) | 1977-01-19 | 1984-06-21 | Foerfarande foer framstaellning av farmaceutiskt aktiva n2-arylsulfonyl-l-argininamider och farmaceutiskt acceptabla salter daerav. |
Applications Claiming Priority (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76067677 | 1977-01-19 | ||
| US05/760,745 US4066773A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,672 US4093712A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US76067277 | 1977-01-19 | ||
| US05/760,668 US4073913A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,929 US4101653A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-argininamides and the pharmaceutically acceptable salts thereof |
| US05/760,676 US4097472A (en) | 1974-11-08 | 1977-01-19 | N2 -arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| US76066877 | 1977-01-19 | ||
| US76074577 | 1977-01-19 | ||
| US76092977 | 1977-01-19 | ||
| US77619577 | 1977-03-10 | ||
| US05/776,195 US4097591A (en) | 1974-11-08 | 1977-03-10 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| JP6650877A JPS6010028B2 (ja) | 1977-06-06 | 1977-06-06 | Ｎ↑２−アリ−ルスルホニル−ｌ−アルギニンアミド類及び薬剤として許容され得るその塩 |
| JP6650877 | 1977-06-06 | ||
| US05/804,331 US4140681A (en) | 1974-11-08 | 1977-06-07 | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US80436877 | 1977-06-07 | ||
| US05/804,368 US4131673A (en) | 1974-11-08 | 1977-06-07 | N2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
| US80433177 | 1977-06-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI780073A FI780073A (fi) | 1978-07-20 |
| FI72316B FI72316B (fi) | 1987-01-30 |
| FI72316C true FI72316C (fi) | 1987-05-11 |
Family
ID=27577127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI780073A FI72316C (fi) | 1977-01-19 | 1978-01-10 | Foerfarande foer framstaellning av farmaceutiskt aktiva n2-arylsulfonyl-l-argininamider och farmaceutiskt acceptabla salter daerav. |
Country Status (17)
| Country | Link |
|---|---|
| CA (1) | CA1131621A (uk) |
| CH (2) | CH633773A5 (uk) |
| DD (1) | DD137352A5 (uk) |
| DE (1) | DE2801478A1 (uk) |
| DK (1) | DK150521C (uk) |
| FI (1) | FI72316C (uk) |
| GB (1) | GB1596971A (uk) |
| GR (1) | GR60787B (uk) |
| IL (1) | IL53685A (uk) |
| IT (1) | IT1126229B (uk) |
| NL (1) | NL187746C (uk) |
| NO (1) | NO158681C (uk) |
| NZ (1) | NZ186198A (uk) |
| PH (1) | PH15913A (uk) |
| SE (1) | SE452624B (uk) |
| SU (1) | SU1181539A3 (uk) |
| UA (1) | UA8370A1 (uk) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE48623B1 (en) * | 1978-08-31 | 1985-03-20 | Mitsubishi Chem Ind | Alpha-(n-arylsulfonyl-l-argininamides,processes for their preparation and pharmaceutical compositions containing these substances |
| SU1042615A3 (ru) * | 1978-08-31 | 1983-09-15 | Мицубиси Кемикал Индастриз Лимитед (Фирма) | Способ получени N @ -арил-сульфонил- @ -аргининамидов |
| GB9209032D0 (en) * | 1992-04-25 | 1992-06-10 | Ciba Geigy Ag | New peptide derivatives |
| GB9426038D0 (en) | 1994-12-22 | 1995-02-22 | Iaf Biochem Int | Low molecular weight bicyclic thrombin inhibitors |
| US6057314A (en) * | 1995-12-21 | 2000-05-02 | Biochem Pharma Inc. | Low molecular weight bicyclic thrombin inhibitors |
| FR2761065B1 (fr) * | 1997-03-20 | 2000-03-03 | Synthelabo | Derives de n-(arginyle)benzenesulfonamide, leur preparation et leur application en therapeutique |
| CN111961114A (zh) * | 2020-08-03 | 2020-11-20 | 扬州中宝药业股份有限公司 | 一种阿加曲班中间体及其制备方法与应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978045A (en) * | 1973-08-13 | 1976-08-31 | Mitsubishi Chemical Industries Ltd. | N2 -dansyl-L-arginine derivatives, and the pharmaceutically acceptable acid addition salts thereof |
-
1977
- 1977-12-16 CA CA293,199A patent/CA1131621A/en not_active Expired
- 1977-12-23 IL IL53685A patent/IL53685A/xx unknown
- 1977-12-27 IT IT31297/77A patent/IT1126229B/it active
-
1978
- 1978-01-10 FI FI780073A patent/FI72316C/fi not_active IP Right Cessation
- 1978-01-11 NZ NZ186198A patent/NZ186198A/xx unknown
- 1978-01-13 PH PH20660A patent/PH15913A/en unknown
- 1978-01-13 DE DE19782801478 patent/DE2801478A1/de active Granted
- 1978-01-13 NL NLAANVRAGE7800448,A patent/NL187746C/xx not_active IP Right Cessation
- 1978-01-17 SE SE7800512A patent/SE452624B/sv not_active IP Right Cessation
- 1978-01-18 NO NO780191A patent/NO158681C/no unknown
- 1978-01-18 CH CH51978A patent/CH633773A5/de not_active IP Right Cessation
- 1978-01-18 DK DK026378A patent/DK150521C/da not_active IP Right Cessation
- 1978-01-18 GB GB2063/78A patent/GB1596971A/en not_active Expired
- 1978-01-18 SU SU782566652A patent/SU1181539A3/ru active
- 1978-01-18 CH CH4530/82A patent/CH648293A5/de not_active IP Right Cessation
- 1978-01-18 UA UA2776611A patent/UA8370A1/uk unknown
- 1978-01-18 GR GR55191A patent/GR60787B/el unknown
- 1978-01-19 DD DD78203302A patent/DD137352A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO158681B (no) | 1988-07-11 |
| DK26378A (da) | 1978-07-20 |
| DE2801478A1 (de) | 1978-07-20 |
| SU1181539A3 (ru) | 1985-09-23 |
| FI72316B (fi) | 1987-01-30 |
| NZ186198A (en) | 1980-12-19 |
| GB1596971A (en) | 1981-09-03 |
| DK150521C (da) | 1987-10-19 |
| SE452624B (sv) | 1987-12-07 |
| NO780191L (no) | 1978-07-20 |
| IL53685A (en) | 1985-12-31 |
| GR60787B (en) | 1978-08-28 |
| IL53685A0 (en) | 1978-03-10 |
| UA8370A1 (uk) | 1996-03-29 |
| NL7800448A (nl) | 1978-07-21 |
| CH648293A5 (en) | 1985-03-15 |
| PH15913A (en) | 1983-04-22 |
| CA1131621A (en) | 1982-09-14 |
| NL187746C (nl) | 1992-01-02 |
| DK150521B (da) | 1987-03-16 |
| NO158681C (no) | 1988-10-19 |
| DE2801478C2 (uk) | 1991-01-31 |
| FI780073A (fi) | 1978-07-20 |
| IT1126229B (it) | 1986-05-14 |
| SE7800512L (sv) | 1978-07-20 |
| CH633773A5 (en) | 1982-12-31 |
| NL187746B (nl) | 1991-08-01 |
| DD137352A5 (de) | 1979-08-29 |
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| Date | Code | Title | Description |
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| MA | Patent expired | ||
| MA | Patent expired |
Owner name: MITSUBISHI KASEI CORPORATION Owner name: OKAMOTO, SHOSUKE |