IT1062293B - REPLACED PROLINES AND RELATED PRODUCTION PROCESS - Google Patents
REPLACED PROLINES AND RELATED PRODUCTION PROCESSInfo
- Publication number
- IT1062293B IT1062293B IT48008/77A IT4800877A IT1062293B IT 1062293 B IT1062293 B IT 1062293B IT 48008/77 A IT48008/77 A IT 48008/77A IT 4800877 A IT4800877 A IT 4800877A IT 1062293 B IT1062293 B IT 1062293B
- Authority
- IT
- Italy
- Prior art keywords
- formula
- replaced
- acid
- prolines
- acylation
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003148 prolines Chemical class 0.000 title 1
- 206010020772 Hypertension Diseases 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 230000006181 N-acylation Effects 0.000 abstract 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The compounds of formula I are prepared by N-acylation of a compound of formula II' by means of an acid of formula III'. In these formulae, R is a hydroxyl, NH2 or alkoxy group, R1 and R4 are each H or an alkyl, phenyl or phenylalkyl group, R2 is H or an organic substituent, R3 is H or a hydroxyl or alkyl group, m is 1, 2 or 3 and n is 0, 1 or 2. The acid of formula III' can be replaced by a functional derivative of the latter or, when n is 1, by an acrylic acid of formula R4CH=C(R1)-COOH. In the latter case, after the acylation, a thiol or thioacid R2SH is added to the double bond of the acryloyl residue. The compounds of formula I are therapeutically active in the treatment of blood hypertension (high blood pressure). <IMAGE>
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/657,792 US4046889A (en) | 1976-02-13 | 1976-02-13 | Azetidine-2-carboxylic acid derivatives |
| US69843276A | 1976-06-21 | 1976-06-21 | |
| US05/751,851 US4105776A (en) | 1976-06-21 | 1976-12-22 | Proline derivatives and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IT1062293B true IT1062293B (en) | 1984-05-23 |
Family
ID=27417986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT48008/77A IT1062293B (en) | 1976-02-13 | 1977-02-11 | REPLACED PROLINES AND RELATED PRODUCTION PROCESS |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS604815B2 (en) |
| AR (4) | AR222445A1 (en) |
| AT (1) | AT365569B (en) |
| AU (1) | AU509899B2 (en) |
| BG (3) | BG37375A3 (en) |
| CA (1) | CA1101864A (en) |
| CH (3) | CH622503A5 (en) |
| DD (1) | DD129442B3 (en) |
| DE (2) | DE2759862C2 (en) |
| DK (1) | DK157487C (en) |
| ES (5) | ES455803A1 (en) |
| FI (1) | FI66596C (en) |
| FR (1) | FR2340932A1 (en) |
| GB (1) | GB1576161A (en) |
| GR (1) | GR69811B (en) |
| HK (1) | HK20281A (en) |
| HU (1) | HU181965B (en) |
| IE (1) | IE44707B1 (en) |
| IL (1) | IL51297A (en) |
| IT (1) | IT1062293B (en) |
| KE (1) | KE3136A (en) |
| MY (2) | MY8200075A (en) |
| NL (1) | NL168509C (en) |
| NO (1) | NO146985C (en) |
| NZ (1) | NZ183130A (en) |
| PH (1) | PH12970A (en) |
| PL (1) | PL118161B1 (en) |
| RO (1) | RO69941A (en) |
| SE (2) | SE423812B (en) |
| SU (1) | SU747422A3 (en) |
| YU (1) | YU40664B (en) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206122A (en) * | 1978-04-14 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Derivatives of pyrrolidinecarboxaldehyde and piperidinecarboxaldehyde and intermediates therefor |
| US4053651A (en) | 1976-05-10 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Compounds and method for alleviating angiotensin related hypertension |
| AU518147B2 (en) * | 1976-12-03 | 1981-09-17 | E.R. Squibb & Sons, Inc. | Derivatives of thiazolidine, thiazine and morpholine carboxylic acids |
| US4129566A (en) * | 1978-02-15 | 1978-12-12 | E. R. Squibb & Sons, Inc. | Derivatives of dehydrocyclicimino acids |
| US4113715A (en) * | 1977-01-17 | 1978-09-12 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
| FR2412537A1 (en) * | 1977-12-22 | 1979-07-20 | Science Union & Cie | NEW SUBSTITUTE THIOBUTYRAMIDES, THEIR METHODS OF OBTAINING AND THEIR PHARMACEUTICAL APPLICATION |
| CA1120400A (en) * | 1977-12-27 | 1982-03-23 | Zola P. Horovitz | Method of treating hypertension and medicaments therefor |
| PH15381A (en) * | 1978-02-21 | 1982-12-17 | Squibb & Sons Inc | Halogen substituted mercaptoacylamino acids |
| JPS559058A (en) * | 1978-07-06 | 1980-01-22 | Dainippon Pharmaceut Co Ltd | 1-(3-mercapto-2-methylpropanoyl)prolyl amino acid derivative |
| CA1109475A (en) * | 1978-07-27 | 1981-09-22 | Miguel A. Ondetti | Thiopropanoylamino acid derivatives |
| CA1144930A (en) * | 1978-08-11 | 1983-04-19 | Miguel A. Ondetti | Mercaptoacyl derivatives of substituted prolines |
| NZ190995A (en) * | 1978-09-05 | 1982-03-09 | American Cyanamid Co | Substituted omega propionyl or butyryl l-prolines and pharmaceutical compositions |
| NL7809121A (en) * | 1978-09-07 | 1980-03-11 | Oce Andeno B V Grubbenvorsterw | OPTICALLY ACTIVE DERIVATIVES OF MERCAPTO-ISO BUTIC ACID. |
| NL7809120A (en) * | 1978-09-07 | 1980-03-11 | Oce Andeno B V Grubbenvorsterw | PROCESS FOR THE PREPARATION OF PROLINE DERIVATIVES. |
| GR73585B (en) * | 1978-09-11 | 1984-03-26 | Univ Miami | |
| US4690937A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| JPS5540622A (en) * | 1978-09-14 | 1980-03-22 | Santen Pharmaceut Co Ltd | Hypotensive agent |
| US4483861A (en) * | 1978-10-31 | 1984-11-20 | Santen Pharmaceutical Co., Ltd. | Antihypertensive sulfur-containing compounds |
| US4198515A (en) * | 1978-12-08 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of 4,5-dihydro-1H-pyrrole-2-carboxylic acids and 1,4,5,6-tetrahydropyridine-2-carboxylic acids |
| US4347371A (en) * | 1978-12-30 | 1982-08-31 | Santen Pharmaceutical Co., Ltd. | Disulfide compounds |
| US4410542A (en) | 1978-12-30 | 1983-10-18 | Santen Pharmaceutical Co., Ltd. | Disulfide compounds |
| CA1138452A (en) * | 1979-01-15 | 1982-12-28 | John Krapcho | Carbamate derivatives of mercaptoacyl hydroxy prolines |
| US4461896A (en) * | 1979-02-07 | 1984-07-24 | Norwich Eaton Pharmaceuticals, Inc. | 1-[Acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids |
| US4220791A (en) * | 1979-03-08 | 1980-09-02 | E. R. Squibb & Sons, Inc. | Mercaptoacylpyrazolidinone carboxylic acid derivatives |
| ZA802420B (en) * | 1979-05-18 | 1981-04-29 | Squibb & Sons Inc | Aminoacyl derivatives of mercaptoacyl amino acids |
| US4234489A (en) * | 1979-06-25 | 1980-11-18 | E. R. Squibb & Sons, Inc. | Pyroglutamic acid derivatives and analogs |
| JPS5629403U (en) * | 1979-08-13 | 1981-03-20 | ||
| DE2937779A1 (en) * | 1979-09-19 | 1981-04-09 | Hoechst Ag, 6000 Frankfurt | AMINO ACID DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
| GB2066240A (en) * | 1979-12-10 | 1981-07-08 | Squibb & Sons Inc | Derivatives of mercaptoacyl amino acids |
| JPS5683483A (en) * | 1979-12-13 | 1981-07-08 | Santen Pharmaceut Co Ltd | Thiazolidine compound |
| GB2065643B (en) * | 1979-12-13 | 1983-08-24 | Kanegafuchi Chemical Ind | Optically active n-mercaptoalkanoylamino acids |
| US4692458A (en) * | 1980-03-05 | 1987-09-08 | University Of Miami | Anti-hypertensive agents |
| SE431331B (en) * | 1980-03-21 | 1984-01-30 | Squibb & Sons Inc | NEW THERAPEUTICALLY ACTIVE SULFUR CONTAINING N-ACYLATED DERIVATIVES OF 4-OXO-L-PROLINE |
| DE3011239A1 (en) * | 1980-03-22 | 1981-10-01 | C.H. Boehringer Sohn, 6507 Ingelheim | SUBSTITUTED ALKYLTHIOACYLAMINO ACIDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS |
| SE8203245L (en) * | 1981-05-27 | 1982-11-28 | Crc Ricerca Chim | PROCEDURE FOR ENANTIOSELECTIVE PREPARATION OF N-SUBSTITUTED PROLINE DERIVATIVES |
| KR860001391B1 (en) * | 1984-07-23 | 1986-09-22 | 보령제약 주식회사 | Method for preparing pyrrolidine derivative |
| JPH06740B2 (en) * | 1984-08-16 | 1994-01-05 | 三菱レイヨン株式会社 | Process for producing optically active carboxylic acid amide |
| HU196369B (en) * | 1984-10-18 | 1988-11-28 | Egyt Gyogyszervegyeszeti Gyar | New process for producing n-acylized l-prolin derivatives |
| KR870001570B1 (en) * | 1984-12-19 | 1987-09-04 | 보령제약 주식회사 | Preparing process for pyrolidine derivatives |
| KR870001569B1 (en) * | 1985-02-11 | 1987-09-04 | 보령제약 주식회사 | Preparing process for pyrolidine derivatives |
| AT395012B (en) * | 1986-06-27 | 1992-08-25 | Richter Gedeon Vegyeszet | METHOD FOR PRODUCING N- (1 (S) | THOXYCARBONYL-3-PHENYL-PROPYL) - (S) -ALANYL- (S) PROLIN AND ITS ACID ADDITION SALTS |
| JP2863534B2 (en) * | 1988-10-24 | 1999-03-03 | マリオン ラボラトリーズ，インコーポレイティド | Pharmaceutical composition |
| US5026873A (en) * | 1989-11-06 | 1991-06-25 | E. R. Squibb & Sons, Inc. | Process for direct isolation of captopril |
| DE4228455A1 (en) * | 1992-08-26 | 1994-09-15 | Beiersdorf Ag | Cosmetic and dermatological sunscreen formulations containing thiols and / or thiol derivatives |
| DE59306051D1 (en) * | 1992-08-26 | 1997-05-07 | Beiersdorf Ag | USE OF RADICAL CATCHERS AS IMMUNODULATING AGENTS IN COSMETIC AND DERMATOLOGICAL PREPARATIONS |
| IT1266570B1 (en) * | 1993-07-30 | 1997-01-09 | Zambon Spa | DERIVATIVES OF PROPANAMIDE N-ETEROARYL SUBSTITUTES USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISEASES |
| US7056935B2 (en) | 1995-06-07 | 2006-06-06 | Gpi Nil Holdings, Inc. | Rotamase enzyme activity inhibitors |
| GB9704522D0 (en) * | 1997-03-05 | 1997-04-23 | Smithkline Beecham Plc | Compounds |
| SI0915088T1 (en) * | 1997-10-31 | 2002-12-31 | F. Hoffmann-La Roche Ag | D-proline derivatives |
| EP1421063A1 (en) * | 2001-08-07 | 2004-05-26 | Sunesis Pharmaceuticals, Inc. | Disulfide and thiosulfonate ligands and libraries comprising these ligands |
| CN100361971C (en) * | 2005-09-19 | 2008-01-16 | 华中师范大学 | Bifunctional L-proline derivatives with adjustable catalytic activity and their preparation |
| AU2009282747B2 (en) | 2008-08-22 | 2015-04-02 | Takeda Pharmaceutical Company Limited | Polymeric benzyl carbonate-derivatives |
| US8901153B2 (en) | 2012-04-27 | 2014-12-02 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA946836A (en) * | 1970-03-18 | 1974-05-07 | Miguel A. Ondetti | Enzyme inhibitor |
-
1977
- 1977-01-14 AU AU21347/77A patent/AU509899B2/en not_active Expired
- 1977-01-19 NZ NZ183130A patent/NZ183130A/en unknown
- 1977-01-20 IL IL51297A patent/IL51297A/en unknown
- 1977-01-21 CA CA270,184A patent/CA1101864A/en not_active Expired
- 1977-01-27 PH PH19390A patent/PH12970A/en unknown
- 1977-01-31 DE DE2759862A patent/DE2759862C2/de not_active Expired
- 1977-01-31 DE DE2703828A patent/DE2703828C2/en not_active Expired
- 1977-02-08 GR GR52745A patent/GR69811B/el unknown
- 1977-02-08 YU YU331/77A patent/YU40664B/en unknown
- 1977-02-09 RO RO7789327A patent/RO69941A/en unknown
- 1977-02-10 FI FI770437A patent/FI66596C/en not_active IP Right Cessation
- 1977-02-10 ES ES455803A patent/ES455803A1/en not_active Expired
- 1977-02-11 NO NO770464A patent/NO146985C/en unknown
- 1977-02-11 AR AR266525A patent/AR222445A1/en active
- 1977-02-11 CH CH170377A patent/CH622503A5/en not_active IP Right Cessation
- 1977-02-11 DK DK059677A patent/DK157487C/en active
- 1977-02-11 SU SU772450455A patent/SU747422A3/en active
- 1977-02-11 BG BG035398A patent/BG37375A3/en unknown
- 1977-02-11 BG BG062894A patent/BG37075A3/en unknown
- 1977-02-11 IT IT48008/77A patent/IT1062293B/en active Protection Beyond IP Right Term
- 1977-02-11 HU HU77SU939A patent/HU181965B/en unknown
- 1977-02-11 BG BG062893A patent/BG37074A3/en unknown
- 1977-02-11 NL NLAANVRAGE7701457,A patent/NL168509C/en not_active IP Right Cessation
- 1977-02-11 DD DD77197339A patent/DD129442B3/en unknown
- 1977-02-11 IE IE305/77A patent/IE44707B1/en not_active IP Right Cessation
- 1977-02-11 SE SE7701561A patent/SE423812B/en not_active IP Right Cessation
- 1977-02-12 PL PL1977195965A patent/PL118161B1/en not_active IP Right Cessation
- 1977-02-12 JP JP52014542A patent/JPS604815B2/en not_active Expired
- 1977-02-13 GB GB4088/77A patent/GB1576161A/en not_active Expired
- 1977-02-14 AT AT0098977A patent/AT365569B/en not_active IP Right Cessation
- 1977-02-14 FR FR7704122A patent/FR2340932A1/en active Granted
- 1977-10-31 AR AR269793A patent/AR222783A1/en active
- 1977-10-31 AR AR269794A patent/AR214649A1/en active
-
1978
- 1978-02-16 ES ES467053A patent/ES467053A1/en not_active Expired
- 1978-02-16 ES ES467050A patent/ES467050A1/en not_active Expired
- 1978-02-16 ES ES467052A patent/ES467052A1/en not_active Expired
- 1978-05-16 ES ES467051A patent/ES467051A1/en not_active Expired
-
1979
- 1979-09-11 AR AR278014A patent/AR226290A1/en active
-
1980
- 1980-02-21 CH CH140980A patent/CH624931A5/fr not_active IP Right Cessation
- 1980-02-21 CH CH141080A patent/CH624932A5/fr not_active IP Right Cessation
-
1981
- 1981-05-14 HK HK202/81A patent/HK20281A/en unknown
- 1981-06-18 KE KE3136A patent/KE3136A/en unknown
- 1981-08-03 SE SE8104660A patent/SE426697B/en not_active IP Right Cessation
-
1982
- 1982-12-30 MY MY75/82A patent/MY8200075A/en unknown
-
1987
- 1987-09-30 MY MYPI87002538A patent/MY102705A/en unknown
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| Date | Code | Title | Description |
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| ITCP | Complementary protection certificate |
Free format text: CCP 45 |
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| MEDD | Supplementary protection certificate for pharmaceutical products: granted |
Free format text: CCP 45, 19920303; E.R. SQUIBB & SONS, INC. |
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| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19950227 |