DE2719901C2 - 9-Desoxy-9-methylen-16,16-dimethyl-prostaglandinderivat - Google Patents
9-Desoxy-9-methylen-16,16-dimethyl-prostaglandinderivatInfo
- Publication number
- DE2719901C2 DE2719901C2 DE2719901A DE2719901A DE2719901C2 DE 2719901 C2 DE2719901 C2 DE 2719901C2 DE 2719901 A DE2719901 A DE 2719901A DE 2719901 A DE2719901 A DE 2719901A DE 2719901 C2 DE2719901 C2 DE 2719901C2
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- deoxy
- methylene
- prostaglandin derivative
- compound
- Prior art date
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical group C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QAOBBBBDJSWHMU-WMBBNPMCSA-N 16,16-dimethylprostaglandin E2 Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O QAOBBBBDJSWHMU-WMBBNPMCSA-N 0.000 description 4
- 241000282560 Macaca mulatta Species 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- WMLGLMGSFIXSGO-KTXJXPLISA-N 9-Deoxy-9-methylene-16,16-dimethyl -PGE2 Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=C)[C@@H]1C\C=C/CCCC(O)=O WMLGLMGSFIXSGO-KTXJXPLISA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000001343 mnemonic effect Effects 0.000 description 3
- 210000000754 myometrium Anatomy 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/682,848 US4060534A (en) | 1976-01-23 | 1976-05-04 | 9-Deoxy-9-methylene-PGF compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2719901A1 DE2719901A1 (de) | 1977-11-24 |
| DE2719901C2 true DE2719901C2 (de) | 1986-09-18 |
Family
ID=24741434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2719901A Expired DE2719901C2 (de) | 1976-05-04 | 1977-05-04 | 9-Desoxy-9-methylen-16,16-dimethyl-prostaglandinderivat |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US4119666A (Direct) |
| JP (1) | JPS609711B2 (Direct) |
| AU (1) | AU512684B2 (Direct) |
| BE (1) | BE854271A (Direct) |
| CH (2) | CH636855A5 (Direct) |
| DE (1) | DE2719901C2 (Direct) |
| FR (1) | FR2392003A1 (Direct) |
| GB (1) | GB1554047A (Direct) |
| HK (1) | HK9485A (Direct) |
| NL (1) | NL7704841A (Direct) |
| ZA (1) | ZA772255B (Direct) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191707A (en) * | 1977-04-11 | 1980-03-04 | The Upjohn Company | 2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds |
| US4317941A (en) * | 1978-04-05 | 1982-03-02 | The Upjohn Company | 2-Decarboxy-2-hydroxymethyl-trans-2,3-didehydro-9-deoxy-9-methylene-PGF compounds |
| US4165436A (en) * | 1978-04-05 | 1979-08-21 | The Upjohn Company | Trans-2,3-didehydro-9-deoxy-9-methylene-PGF compounds |
| US4188332A (en) * | 1978-04-05 | 1980-02-12 | The Upjohn Company | Trans-2,3-didehydro-9-deoxy-9-methylene-PGF,1,11- or 1,15-lactones |
| US4230629A (en) * | 1978-09-08 | 1980-10-28 | The Upjohn Company | 16-Phenoxy-9-deoxy-9-methylene-PGF compounds |
| US4260825A (en) * | 1979-04-02 | 1981-04-07 | The Upjohn Company | 2-Decarboxy-2-aminomethyl-19-keto-PG compounds |
| US4289785A (en) * | 1980-08-06 | 1981-09-15 | The Upjohn Company | Method and compositions involving prostaglandins |
| KR101045935B1 (ko) * | 2009-03-11 | 2011-07-01 | 연성정밀화학(주) | 프로스타글란딘 유도체의 제조방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US691157A (en) * | 1900-07-07 | 1902-01-14 | Hoechst Ag | Trimethyl hexahydroöxybenzylanilin and process of making same. |
| US2520015A (en) * | 1948-01-05 | 1950-08-22 | Lilly Co Eli | Acid addition salts of 1-cyclopentyl-2-methyl-amino propane compounds and vasoconstrictor compositions thereof |
| US2736746A (en) * | 1954-09-08 | 1956-02-28 | Hoffmann La Roche | Diamine compounds |
| US2805266A (en) * | 1955-03-07 | 1957-09-03 | Ziegler Karl | Process for preparing azulenes |
| US3046280A (en) * | 1955-11-24 | 1962-07-24 | Philips Corp | Primary, secondary and tertiary amines having a spasmolytic effect and method of producing these compounds |
| US3920643A (en) * | 1966-08-09 | 1975-11-18 | George E Just | Intermediates for producing prostaglandins |
| CH553207A (fr) * | 1972-03-30 | 1974-08-30 | Firmenich & Cie | Procede pour la preparation de derives azotes. |
| US3931299A (en) * | 1974-09-13 | 1976-01-06 | American Home Products Corporation | 9β-Formyl prostaglandin derivatives |
| US4021467A (en) * | 1975-03-10 | 1977-05-03 | The Upjohn Company | 9-Deoxy-9α-hydroxymethyl-PGF2 analogs |
| US4045449A (en) * | 1975-06-23 | 1977-08-30 | The Upjohn Company | PG-type 1,15-lactones |
-
1977
- 1977-04-13 ZA ZA00772255A patent/ZA772255B/xx unknown
- 1977-04-18 AU AU24340/77A patent/AU512684B2/en not_active Expired
- 1977-05-03 FR FR7713427A patent/FR2392003A1/fr active Granted
- 1977-05-03 GB GB18405/77A patent/GB1554047A/en not_active Expired
- 1977-05-03 NL NL7704841A patent/NL7704841A/xx not_active Application Discontinuation
- 1977-05-04 BE BE177281A patent/BE854271A/xx not_active IP Right Cessation
- 1977-05-04 JP JP52050861A patent/JPS609711B2/ja not_active Expired
- 1977-05-04 CH CH558477A patent/CH636855A5/de not_active IP Right Cessation
- 1977-05-04 DE DE2719901A patent/DE2719901C2/de not_active Expired
- 1977-09-12 US US05/832,243 patent/US4119666A/en not_active Expired - Lifetime
- 1977-09-12 US US05/832,241 patent/US4103097A/en not_active Expired - Lifetime
- 1977-09-12 US US05/832,247 patent/US4103098A/en not_active Expired - Lifetime
- 1977-09-12 US US05/832,330 patent/US4104476A/en not_active Expired - Lifetime
- 1977-09-12 US US05/832,766 patent/US4144253A/en not_active Expired - Lifetime
- 1977-09-12 US US05/832,242 patent/US4119649A/en not_active Expired - Lifetime
-
1982
- 1982-04-23 CH CH249482A patent/CH642063A5/de not_active IP Right Cessation
-
1985
- 1985-01-31 HK HK94/85A patent/HK9485A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52133954A (en) | 1977-11-09 |
| US4103097A (en) | 1978-07-25 |
| BE854271A (fr) | 1977-11-04 |
| AU512684B2 (en) | 1980-10-23 |
| US4104476A (en) | 1978-08-01 |
| FR2392003B1 (Direct) | 1980-02-29 |
| US4144253A (en) | 1979-03-13 |
| HK9485A (en) | 1985-02-08 |
| ZA772255B (en) | 1978-11-29 |
| AU2434077A (en) | 1978-10-26 |
| GB1554047A (en) | 1979-10-17 |
| NL7704841A (nl) | 1977-11-08 |
| CH636855A5 (de) | 1983-06-30 |
| US4103098A (en) | 1978-07-25 |
| DE2719901A1 (de) | 1977-11-24 |
| FR2392003A1 (fr) | 1978-12-22 |
| CH642063A5 (de) | 1984-03-30 |
| US4119649A (en) | 1978-10-10 |
| US4119666A (en) | 1978-10-10 |
| JPS609711B2 (ja) | 1985-03-12 |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |